piperine profile

piperine : A N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

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Flora	Rank	Flora Definition	Family	Family Definition
Piper	genus	A plant genus of the family PIPERACEAE that includes species used for spicy and stimulating qualities.[MeSH]	Piperaceae	A family of flowering plants in the order Piperales best known for the black pepper widely used in SPICES, and for KAVA and Betel used for neuroactive properties.[MeSH]

ID Source	ID
PubMed CID	638024
CHEMBL ID	43185
CHEBI ID	28821
CHEBI ID	93043
SCHEMBL ID	94058
SCHEMBL ID	94059
MeSH ID	M0053196

Synonym
BIDD:ER0675
LS-14576
smr000112278
MLS002153830
bdbm50148573
CHEBI:28821 ,
1-[(2e,4e)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine
1-[(2e,4e)-5-(1,3-benzodioxol-5-yl)-2,4-pentadienoyl]piperidine
(e,e)-1-piperoylpiperidine
(2e,4e)-5-(1,3-benzodioxol-5-yl)-1-(1-piperidyl)penta-2,4-dien-1-one
piperidine, 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-, (e,e)-
(e,e) 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine
1-piperoylpiperidine
nsc-21727
piperidine, (e,e)-
piperin
nsc21727 ,
piperidine,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-, (e,e)-
7780-20-3
SDCCGMLS-0066693.P001
piperine (aliphatic)
fema no. 2909
piperidine, 1-piperoyl-, (e,e)-
1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine, (e,e)-
piperidine, 1-((2e,4e)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-
einecs 202-348-0
piperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-, (e,e)-
1,3-benzodioxol-5-yl-1-oxo-2,4-pentadienyl-piperine
bioperine
nsc 21727
1-piperoylpiperidine, (e,e)-
piperoylpiperidine
ccris 5572
PRESTWICK_398
cas-94-62-2
PRESTWICK3_000474
IDI1_000954
BSPBIO_002515
SPECTRUM5_001507
BSPBIO_000608
piperidine, 1-(5-(3,4-methylenedioxyphenyl)-1-oxo-2,4-pentadienyl)-
1-(5-(3,4-methylenedioxyphenyl)-1-oxo-2,4-pentadienyl)piperidine
nsc 242267
ai3-01439
piperidine, 1-[(2e,4e)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-
inchi=1/c17h19no3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12h,1,4-5,10-11,13h2/b6-2+,7-3
1-[(2e,4e)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]piperidine
n-[(e,e)-piperoyl]piperidine
1-piperoyl-piperidine
94-62-2
C03882
piperine
SR-01000638580-1
piperine, >=97%, fg
piperine, >=97%
PRESTWICK2_000474
NCGC00094872-03
NCGC00094872-01
NCGC00094872-02
SPECTRUM1500873
BPBIO1_000670
NCGC00094872-04
NCGC00094872-05
gtpl2489
((1-5-(1,3)-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine
(2e,4e)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one
(1-(5-(1,3)-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine
P-6920
N-EE-PIPEROYL-PIPERIDINE ,
n-(e,e)-piperoyl-piperidine
MLS002473213
HMS2092M22
AC-11746
AG-205/01792022
CHEMBL43185 ,
HMS502P16
AKOS003369047
1-piperylpiperidine
1-[5-(1,3-benzodioxol-5-yl)-2,4-pentadienoyl]piperidine
P0460
HMS1569O10
HMS1921M12
NCGC00094872-06
HMS2096O10
dtxcid701805
NCGC00256392-01
tox21_302746
dtxsid3021805 ,
ST079380
tox21_201990
NCGC00259539-01
nsc757803
nsc-757803
pharmakon1600-01500873
ai 3-01439
piperidine, 1-piperoyl-
HMS2270M18
CCG-39991
unii-u71xl721qk
piperine [usp]
2,4-pentadien-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2e,4e)-
u71xl721qk ,
STL377909
(2e,4e)-5-(1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
piperine [mi]
piperine [fhfi]
piperine [who-dd]
piperine [usp-rs]
(e,e)-1-(5-(1,3-benzodioxol-5-yl)-2,4-pentadienoyl)piperidine
(2e,4e)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
piperine [inci]
piperine (constituent of black pepper) [dsc]
S2344
SCHEMBL94058
SCHEMBL94059
BBL027541
1-[(2e,4e)-5-(1,3-benzodioxol-5-yl)-2,4-pentadienoyl]piperidine #
1,3-benzodioxol-5-yl-1-oxo-2,4-pentadienyl-piperidine
AB00052185_08
mfcd00005839
(2e,4e)-5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
CS-6155
HY-N0144
piperine, analytical standard
SR-01000638580-2
SR-01000638580-5
sr-01000638580
SR-01000638580-6
CHEBI:93043
piperine, united states pharmacopeia (usp) reference standard
piperine, european pharmacopoeia (ep) reference standard
SBI-0051621.P002
NCGC00094872-09
fema 2909
1-piperoyl-(e,e)-piperidine
SW196642-2
DB12582
BCP18901
Q414501
Q27164772
5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-1-penta-2,4-dienone
Z104476830
piperine (1-piperoylpiperidine)
piperine,(s)
(2e,4e)-5-(benzo[d][1,3]dioxol-5-yl)-1-
(piperidin-1-yl)penta-2,4-dien-1-one
147030-08-8
AS-17442
bioperine;1-piperoylpiperidine
BRD-K59522102-001-08-8
5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
AMY40672
1-trans,trans-piperinoyl-piperidine
STARBLD0008505
CS-0368434
5-(1,3-dioxaindan-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
EN300-20100
(2e,4e)-5-(1,3-dioxaindan-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
EN300-7392817
AKOS040750229
piperine (constituent of black pepper)
1-((2e,4e)-5-(1,3-benzodioxol-5-yl)-2,4-pentadienoyl)piperidine
1-((2e,4e)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl)piperidine
piperine (usp-rs)
1-((2e,4e)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine
piperine (usp)
n-((e,e)-piperoyl)piperidine
piperine1537

Excerpt	Reference	Relevance
"Piperine is an alkaloid from the source plant of both black and white pepper grains, Piper nigrum."	( Inhibition of monoamine oxidase by derivatives of piperine, an alkaloid from the pepper plant Piper nigrum, for possible use in Parkinson's disease. Al-Baghdadi, OB; Geldenhuys, WJ; Prater, NI; Van der Schyf, CJ, 2012)	1.35
"Piperine (PIP) is an alkaloid found primarily in Piper longum, and this natural compound has been shown to exert effects on proliferation and survival against various types of cancer. "	( Piperine for treating breast cancer: A review of molecular mechanisms, combination with anticancer drugs, and nanosystems. Chorilli, M; Quijia, CR, 2022)	3.61
"Piperine is an alkaloid extracted from the seed of Piper spp., which has demonstrated a larvicidal effect against Ae. "	( Polymer-based nanostructures loaded with piperine as a platform to improve the larvicidal activity against Aedes aegypti. da Silva da Costa, FA; da Silva, OS; de Lemos, AB; de Moraes, FM; de Oliveira, JG; Fernandes, M; Gonçalves, DZ; Kanis, LA; Magnago, RF; Morisso, FDP; Pilz-Júnior, HL; Prophiro, JS; Variza, PF; Zepon, KM, 2022)	2.43
"Piperine (PIP) is a herbal drug with well-known anticancer activity against different types of cancer including hepatocellular carcinoma. "	( Pectin coated nanostructured lipid carriers for targeted piperine delivery to hepatocellular carcinoma. Abdallah, OY; El-Ganainy, SO; Elnaggar, YSR; Gowayed, MA; Shehata, EMM; Sheta, E, 2022)	2.41
"Piperine is a fascinating substance since it can be used as a biomarker in combination with other bioactive compounds or their analogues, as well as therapeutic molecules used for the healing of a variety of diseases. "	( Synergistic Effect of Piperine and its Derivatives: A Comprehensive Review. Chopra, B; Dhingra, AK; Saini, N, 2023)	2.67
"Piperine (PIP) is a major phytoconstituent in black pepper which is responsible for various pharmacological actions such as anti-inflammatory, antioxidant, and antitumor activity. "	( Piperine Attenuates Cigarette Smoke-Induced Oxidative Stress, Lung Inflammation, and Epithelial-Mesenchymal Transition by Modulating the SIRT1/Nrf2 Axis. Durugkar, S; Gokhale, S; Jain, S; Jala, A; Naidu, VGM; Panda, SR; Saha, P; Shantanu, PA; Sharma, P, 2022)	3.61
"Piperine is an alkaloid mostly found in the fruits of several species of the Piper genus, and its anti-inflammatory potential is already known. "	( Piperine-loaded nanoparticles incorporated into hyaluronic acid/sodium alginate-based membranes for the treatment of inflammatory skin diseases. Carvalho, SG; Chiavacci, LA; Chorilli, M; Dos Santos, KP; Meneguin, AB; Politi, FAS; Rodero, CF; Sorrechia, R, 2023)	3.8
"Piperine is a principal constituent of piper species frequently used as antitumor and anti-inflammatory natural compound."	( Piperine suppresses inflammatory fibroblast-like synoviocytes derived from rheumatoid arthritis patients Via NF-κB inhibition. Baito, QN; Jaafar, HM; Mohammad, TAM, )	2.3
"Piperine is a natural compound found in black pepper that has been traditionally used for various therapeutic purposes. "	( Significant Advancement in Various Synthetic Strategies and Pharmacotherapy of Piperine Derivatives: A Review. Ahsan, MJ; Arya, A; Joshi, S; Khurana, N; Kumar, R; Mazumder, A; Rana, K; Shabana, K; Tyagi, S; Yar, MS, 2023)	2.58
"Piperine is a chief alkaloid compound of natural black pepper exhibits excellent anti-convulsant efficiency in the anti-epileptic treatment."	( Rational design of ultra-small photoluminescent copper nano-dots loaded PLGA micro-vessels for targeted co-delivery of natural piperine molecules for the treatment for epilepsy. Ding, SW; Nie, XD; Yang, L; Zhang, DT; Zhang, WG; Zhu, D, 2020)	1.49
"Piperine is an alkaloid naturally found in black pepper with a myriad of pharmacological attributes. "	( The effect of piperine on oral absorption of cannabidiol following acute vs. chronic administration. Domb, AJ; Hoffman, A; Izgelov, D, 2020)	2.36
"Piperine (PIP) is a naturally occurring pungent nitrogenous substance present in the fruits of peppers."	( Piperine synergistically enhances the effect of temozolomide against temozolomide-resistant human glioma cell lines. Jeong, S; Jung, S; Oh, JW; Park, GS; Shin, J, 2020)	2.72
"Piperine is a key bioactive alkaloid found in plants of piperaceae family. "	( Propitious Profile of Peppery Piperine. Aggarwal, G; Bakshi, H; Dhingra, GA; Nagpal, M; Singh, M, 2021)	2.35
"Piperine is a fascinating molecule of natural origin with several modes of its action, not only possesses its own therapeutic activity but also enhances the therapeutic efficacy of other synthetic and natural drug molecules. "	( Propitious Profile of Peppery Piperine. Aggarwal, G; Bakshi, H; Dhingra, GA; Nagpal, M; Singh, M, 2021)	2.35
"Piperine (PIP) is an alkaloid which is potent as a therapeutic agent. "	( Degree of crosslinking in β-cyclodextrin-based nanosponges and their effect on piperine encapsulation. González, S; Guineo-Alvarado, J; Hermosilla, J; Lim, LT; Medina, C; Quilaqueo, M; Rolleri, A; Rubilar, M, 2021)	2.29
"Piperine (PIP) is an alkaloid present in several species of piper, mainly Piper nigrum Linn. "	( Piperine: Chemical, biological and nanotechnological applications. Araujo, VH; Chorilli, M; Quijia, CR, 2021)	3.51
"Piperine is an alkaloid that has extensive pharmacological activity and impacts other active substances bioavailability due to inhibition of CYP450 enzymes, stimulation of amino acid transporters and "	( Combinations of Piperine with Hydroxypropyl-β-Cyclodextrin as a Multifunctional System. Cielecka-Piontek, J; Jenczyk, J; Kobus-Cisowska, J; Kozak, M; Lewandowska, K; Płazińska, A; Płaziński, W; Rosiak, N; Stasiłowicz, A; Szulc, P; Tykarska, E, 2021)	2.41
"Piperine (PPN) is a water-insoluble bioactive compound used for different diseases."	( Formulation of Piperine-Chitosan-Coated Liposomes: Characterization and In Vitro Cytotoxic Evaluation. Alanazi, S; Almutairy, BK; Alruwaili, NK; Alshehri, S; Altamimi, MA; Gilani, SJ; Hussain, A; Imam, SS; Qamar, W; Zafar, A, 2021)	1.7
"Piperine is a major constituent of Piper nigrum L. "	( Characterization of piperine metabolites in rats by ultra-high-performance liquid chromatography with electrospray ionization quadruple time-of-flight tandem mass spectrometry. Gao, T; Han, H; Lu, L; Xue, H; Zhang, T, 2017)	2.22
"Piperine is a nitrogenous pungent substance exhibiting multifunctional pharmacological properties. "	( Piperine Triggers Apoptosis of Human Oral Squamous Carcinoma Through Cell Cycle Arrest and Mitochondrial Oxidative Stress. Afzal, M; Ahamad, MS; Arshad, M; Jafri, A; Siddiqui, S, 2017)	3.34
"Piperine is an alkaloid responsible for the pungency of black pepper and long pepper. "	( Piperine induces osteoblast differentiation through AMPK-dependent Runx2 expression. Jang, WG; Kim, DY; Kim, EJ, 2018)	3.37
"Piperine (E,E-) is a naturally occurring pungent and spicy constituent of black pepperand is also used as an added flavoring ingredient to foods and beverages. "	( Absence of adverse effects following administration of piperine in the diet of Sprague-Dawley rats for 90 days. Aubanel, M; Bastaki, M; Bauter, M; Cachet, T; Demyttenaere, J; Diop, MM; Harman, CL; Hayashi, SM; Krammer, G; Li, X; Llewellyn, C; Mendes, O; Renskers, KJ; Schnabel, J; Smith, BPC; Taylor, SV, 2018)	2.17
"Piperine (PIP) is an alkaloid characterized by memory-enhancing properties but challenging oral delivery obstacles."	( Oral Brain-Targeted Microemulsion for Enhanced Piperine Delivery in Alzheimer's Disease Therapy: In Vitro Appraisal, In Vivo Activity, and Nanotoxicity. Abdallah, OY; Abdelmonsif, DA; Elnaggar, YSR; Etman, SM, 2018)	1.46
"Piperine is an attractive therapeutic alkaloid from black pepper that exhibits a broad spectrum of pharmacological properties over various pathological disorders including cancer. "	( Potential of piperine in modulation of voltage-gated K+ current and its influences on cell cycle arrest and apoptosis in human prostate cancer cells. Ba, Y; Malhotra, A, 2018)	2.29
"Piperine (PIP) is a natural alkaloid isolated from "	( Characteristics, Biological Properties and Analytical Methods of Piperine: A Review. Chorilli, M; Quijia, CR, 2020)	2.24
"Piperine is a major pungent alkaloid present in black pepper (Piper nigrum L). "	( Antitumor and Apoptosis-inducing Effects of Piperine on Human Melanoma Cells. Che, JH; Cho, SD; Choi, CS; Choo, GS; Jung, JY; Kim, BS; Kim, HJ; Kim, SH; Kim, SK; Nam, JS; Park, BK; Park, YS; Woo, JS; Yoo, ES, 2019)	2.22
"Piperine is an attractive therapeutic alkaloid from black pepper that exhibits a broad spectrum of pharmacological properties over various pathological disorders including cancer. "	( Piperine blocks voltage gated K George, K; Malathi, R; Thomas, NS, 2019)	3.4
"Piperine is a bioactive component of black pepper, Piper nigrum Linn, commonly used for daily consumption and in traditional medicine. "	( Antitumor efficacy of piperine in the treatment of human HER2-overexpressing breast cancer cells. Choi, JH; Do, MT; Jeong, HG; Jeong, TC; Khanal, T; Kim, HG; Park, BH; Tran, TP, 2013)	2.15
"Piperine is a spice principle, and its protective role against oxidative damage and lipid peroxidation has been reported. "	( Effects of piperine in experimental intestinal ischemia reperfusion model in rats. Akcan, A; Akyıldız, HY; Akyüz, M; Karabacak, A; Sözüer, E, 2013)	2.22
"Piperine is an important active component of the Chinese herb Large leaf moss. "	( Piperine effectively protects primary cultured atrial myocytes from oxidative damage in the infant rabbit model. Guan, Y; Liu, P; Liu, Y; Ma, Y; Shan, Z; Tian, M; Wang, Y; Wang, Z, 2014)	3.29
"Piperine is a secondary metabolite of black pepper. "	( Derivatives form better lipoxygenase inhibitors than piperine: in vitro and in silico study. Dileep, KV; Haridas, M; Prasanth, S; Sabu, A; Sadasivan, C; Sharanya, CS; Tomy, MJ, 2015)	2.11
"Piperine is a simple alkaloid isolated from the seeds of Piper nigrum. "	( Piperine: bioactivities and structural modifications. Lv, M; Qu, H; Xu, H, 2015)	3.3
"Piperine (PA) is a potential cholesterol lowering agent."	( Piperine prevents cholesterol gallstones formation in mice. Chen, NH; Chu, SF; Han, N; Hu, JF; Li, JW; Li, YT; Liu, H; Song, XY; Tang, J; Xu, S; Zhang, DM, 2015)	2.58
"Piperine is a major alkaloid component of black pepper (Piper nigrum Linn), which is a widely consumed spice. "	( Piperine from black pepper inhibits activation-induced proliferation and effector function of T lymphocytes. Doucette, CD; Hoskin, DW; Liwski, RS; Rodgers, G, 2015)	3.3
"Piperine is a potential agonist of PXR and an inducer of PXR, which may induce CYP3A4 gene expression at the mRNA and protein levels. "	( The protective effect of piperine on dextran sulfate sodium induced inflammatory bowel disease and its relation with pregnane X receptor activation. Chen, Z; Gao, Y; Hu, D; Liang, Q; Ma, Z; Tan, H; Tang, X; Wang, Y; Xiao, C; You, Q; Zhang, X, 2015)	2.16
"Piperine (PIP) is a phytopharmaceutical with reported neuroprotective potential in Alzheimer's disease (AD). "	( Intranasal Piperine-Loaded Chitosan Nanoparticles as Brain-Targeted Therapy in Alzheimer's Disease: Optimization, Biological Efficacy, and Potential Toxicity. Abdallah, OY; Abdelmonsif, DA; Elnaggar, YS; Etman, SM, 2015)	2.25
"Piperine is an exact of the active phenolic component from Black pepper. "	( Piperine mediates LPS induced inflammatory and catabolic effects in rat intervertebral disc. Hu, Y; Li, K; Li, Y; Xu, B; Zhao, J, 2015)	3.3
"Piperine (PIP) is a natural alkaloid with memory enhancing potentials."	( Novel piperine-loaded Tween-integrated monoolein cubosomes as brain-targeted oral nanomedicine in Alzheimer's disease: pharmaceutical, biological, and toxicological studies. Abdallah, OY; Abdelmonsif, DA; Elnaggar, YS; Etman, SM, 2015)	1.62
"Piperine is a simple and pungent alkaloid found in the seeds of black pepper (Piper nigrum). "	( Lessons from black pepper: piperine and derivatives thereof. Borges, F; Chavarria, D; Magalhães e Silva, D; Remião, F; Silva, T, 2016)	2.17
"Piperine (PIP) is a Chinese medicine with anti-inflammatory and antioxidant effects."	( Piperine induces autophagy by enhancing protein phosphotase 2A activity in a rotenone-induced Parkinson's disease model. Chen, M; Duan, C; Gao, G; Liu, J; Lu, L; Wang, X; Wang, Y; Wu, X; Yang, H, 2016)	2.6
"Piperine is an alkaloid present in black pepper (Piper nigrum), one of the most widely used spices, in long pepper (Piper longum), and other Piper species fruits belonging to the family of Piperaceae."	( Piperine and Its Role in Chronic Diseases. Derosa, G; Maffioli, P; Sahebkar, A, )	2.3
"Piperine is a major component of black pepper, Piper nigrum Linn, used widely in traditional medicine. "	( Suppression of phorbol-12-myristate-13-acetate-induced tumor cell invasion by piperine via the inhibition of PKCα/ERK1/2-dependent matrix metalloproteinase-9 expression. Choi, JH; Chung, YC; Han, EH; Hwang, YP; Jeong, HG; Kim, HG; Yun, HJ, 2011)	2.04
"Piperine is a major alkaloid of black pepper (Piper nigrum Linn.) and long pepper (P. "	( Involvement of serotonergic system in the antidepressant-like effect of piperine. Che, CT; Ip, SP; Mao, QQ; Xian, YF, 2011)	2.04
"Piperine is a phenolic component of black pepper (Piper nigrum) and long pepper (Piper longum), fruits used in traditional Asian medicine. "	( Piperine ameliorates the severity of cerulein-induced acute pancreatitis by inhibiting the activation of mitogen activated protein kinases. Bae, GS; Hwang, SY; Jeong, J; Kim, BJ; Kim, MS; Kim, TH; Koo, BS; Lee, HY; Lee, SH; Park, KC; Park, SJ; Shin, YK; Song, HJ, 2011)	3.25
"Piperine is a potent monoaminooxidase inhibitor and stimulates the synthesis of serotonin."	( Piperine protects epilepsy associated depression: a study on role of monoamines. Nayak, S; Pal, A; Sahu, PK; Swain, T, 2011)	2.53
"Piperine is a major component of black (Piper nigrum Linn) and long (Piper longum Linn) peppers, and is widely used as a traditional food and medicine. "	( Piperine inhibits PMA-induced cyclooxygenase-2 expression through downregulating NF-κB, C/EBP and AP-1 signaling pathways in murine macrophages. Choi, JH; Chung, YC; Han, EH; Jang, WS; Jeong, HG; Khanal, T; Kim, HG; Park, BH; Tran, TP, 2012)	3.26
"Piperine is a pure, pungent alkaloid constituent of black and long peppers (piper nigrum and piper longum), which is a most common spice used throughout the world."	( Oral supplementation of piperine leads to altered phase II enzymes and reduced DNA damage and DNA-protein cross links in Benzo(a)pyrene induced experimental lung carcinogenesis. Banu, SM; Sakthisekaran, D; Selvendiran, K, 2005)	1.36
"Piperine is a major component of black (Piper nigrum Linn) and long pepper (Piper longum Linn) used widely in various systems of traditional medicine. "	( Chemopreventive effect of piperine on mitochondrial TCA cycle and phase-I and glutathione-metabolizing enzymes in benzo(a)pyrene induced lung carcinogenesis in Swiss albino mice. Padmavathi, R; Sakthisekaran, D; Selvendiran, K; Singh, JP; Thirunavukkarasu, C, 2005)	2.07
"Piperine is a pure, pungent alkaloid constituent of black and long peppers (Piper nigrum and Piper longum), that acts as an antioxidant and anticancer agent by its numerous macromolecules associated with them."	( In vivo effect of piperine on serum and tissue glycoprotein levels in benzo(a)pyrene induced lung carcinogenesis in Swiss albino mice. Prince Vijeya Singh, J; Sakthisekaran, D; Selvendiran, K, 2006)	1.39
"Piperine is a major component of black pepper, Piper nigrum Linn, used widely in traditional medicine. "	( Piperine protects cisplatin-induced apoptosis via heme oxygenase-1 induction in auditory cells. Choi, BM; Chung, HT; Hong, SJ; Kim, BR; Kim, SM; Li, G; Park, R; Park, TK, 2007)	3.23
"Piperine is a major pungent substance and active component of black pepper (Piper nigrum Linn.) and long pepper (Piper longum Linn.). "	( Antimutagenic effects of piperine on cyclophosphamide-induced chromosome aberrations in rat bone marrow cells. Himakoun, L; Soontornchai, S; Temcharoen, P; Wongpa, S, )	1.88
"Piperine (CAS 94-62-2) is a constituent of various spices and is used as a common food additive all over the world. "	( Assessment of genotoxic effect of piperine using Salmonella typhimurium and somatic and somatic and germ cells of Swiss albino mice. Dhuley, J; Ghaskadbi, S; Joshi, SS; Karekar, VR; Mujumdar, AM; Shinde, SL, 1996)	2.02
"Piperine is an inhibitor of various hepatic and other enzymes involved in the biotransformation of drugs. "	( Comparative anti-nociceptive, anti-inflammatory and toxicity profile of nimesulide vs nimesulide and piperine combination. Bansal, P; Bhardwaj, RK; Gupta, SK; Velpandian, T, 2000)	1.97
"Piperine (CAS 94-62-2) is a constituent of various spices which are used as common food additives all over the world. "	( Reproductive toxicity of piperine in Swiss albino mice. Daware, MB; Ghaskadbi, S; Mujumdar, AM, 2000)	2.05
"Piperine (1) is an alkaloidal constituent of black and long peppers recently established as a bioavailability enhancer of drugs and other substances."	( Antidiarrhoeal activity of piperine in mice. Bajad, S; Bedi, KL; Johri, RK; Singla, AK, 2001)	1.33

Excerpt	Reference	Relevance
"Piperine has been shown to have a wide range of activity, including MAO inhibitory activity."	( Inhibition of monoamine oxidase by derivatives of piperine, an alkaloid from the pepper plant Piper nigrum, for possible use in Parkinson's disease. Al-Baghdadi, OB; Geldenhuys, WJ; Prater, NI; Van der Schyf, CJ, 2012)	1.35
"Piperine has been associated with neuroprotective effects and monoamine oxidase (MAO) inhibition, thus being an attractive scaffold to develop new antiparkinsonian agents. "	( Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies. Borges, F; Chavarria, D; Fernandes, C; Gil-Martins, E; Oliveira, PJ; Remião, F; Silva, C; Silva, R; Silva, T; Silva, V; Soares, P, 2020)	2.25
"Piperine has remarkable potential to modulate the functional activity of metabolic enzymes and drug transporters, and thus there has been a great interest in the therapeutic application of this widely used spice as alternative medicine and bioavailability enhancer."	( A Unifying Perspective in Blunting the Limited Oral Bioavailability of Curcumin: A Succinct Look. Alqahtani, A; Alqahtani, T; Balakumar, P; Lakshmiraj, RS; Rupeshkumar, M; Singh, G; Sundram, K; Thangathirupathi, A, 2022)	1.44
"Piperine has been indicated as a bioavailability enhancer of turmeric and consequently of its biological effects."	( Turmeric supplementation with piperine is more effective than turmeric alone in attenuating oxidative stress and inflammation in hemodialysis patients: A randomized, double-blind clinical trial. Braga, CC; Carlos da Cunha, L; Costa, NA; de Souza Freitas, ATV; Freitas E Silva-Santana, NC; Peixoto, MDRG; Pereira Martins, TF; Rodrigues, HCN; Silva, MAC, 2022)	1.73
"Piperine (PIP) has been verified to drive certain cancer cell death and increases chemosensitivity of DOX."	( Piperine improves the sensitivity of osteosarcoma cells to doxorubicin by inducing apoptosis and inhibiting the PI3K/AKT/GSK-3β pathway. Liu, J; Qi, Y; Wang, W; Yao, L, 2023)	3.07
"Piperine has the ability to improve the bioavailability of many compounds when co-administered."	( Amorphous System of Hesperetin and Piperine-Improvement of Apparent Solubility, Permeability, and Biological Activities. Cielecka-Piontek, J; Miklaszewski, A; Pietrzak, R; Wdowiak, K, 2023)	1.91
"Piperine (PIP) has been proven to be a promising efflux pump inhibitor in some bacteria."	( Effect of piperine on the inhibitory potential of MexAB-OprM efflux pump and imipenem resistance in carbapenem-resistant Pseudomonas aeruginosa. Fei, B; Guo, M; Li, D; Li, Y; Liu, X; Liu, Y; Ren, Y; You, X; Zhu, R, 2023)	2.03
"Piperine has been reported to have anti-inflammatory and anti-allergic pharmacological activities."	( The anti-anaphylactoid effects of Piperine through regulating MAS-related G protein-coupled receptor X2 activation. Che, D; Gao, J; Hu, S; Jiang, W; Liu, R; Ma, R; Qiao, C; Wang, J; Zhang, T, 2020)	1.56
"Piperine (Pip) has been widely studied for its multiple activities such as antidepressant, anti-epileptic, and so forth. "	( Piperine fast disintegrating tablets comprising sustained-release matrix pellets with enhanced bioavailability: formulation, Adu-Frimpong, M; Deng, W; Gu, Z; Xu, X; Yu, J; Zhou, G; Zhu, Y, 2020)	3.44
"Piperine has been reported to possess effective chemopreventive activity."	( Piperine as a Potential Anti-cancer Agent: A Review on Preclinical Studies. Jafari, S; Manayi, A; Nabavi, SM; Setzer, WN, 2018)	2.64
"Piperine has been shown to have antioxidant activity and a cognitive-enhancing effect following long-term oral administration. "	( Piperine restores streptozotocin-induced cognitive impairments: Insights into oxidative balance in cerebrospinal fluid and hippocampus. Ashrafpour, M; Azizi, MG; Esmaeili, MR; Gol, M; Hosseinzadeh, S; Kazemi, S; Khalili-Fomeshi, M; Moghadamnia, AA, 2018)	3.37
"Piperine has various pharmacological effects and can modulate the functional activity of metabolic enzymes and drug transporters. "	( Piperine-mediated drug interactions and formulation strategy for piperine: recent advances and future perspectives. Back, SY; Han, HK; Kim, HY; Lee, SH, 2018)	3.37
"Piperine has been found to increase bioavailability of several drugs including Amoxicillin, Cefotaxime, Theophylline and Propranolol."	( A Randomized, Controlled, Phase III Clinical Trial to Evaluate the Efficacy and Tolerability of Risorine with Conventional Rifampicin in the Treatment of Newly Diagnosed Pulmonary Tuberculosis Patients. Jagannath, K; Patel, A; Patel, M; Patel, N; Vora, A, 2017)	1.18
"Piperine has been determined safe under conditions of intended use as a flavoring substance by regulatory and scientific expert bodies."	( Absence of adverse effects following administration of piperine in the diet of Sprague-Dawley rats for 90 days. Aubanel, M; Bastaki, M; Bauter, M; Cachet, T; Demyttenaere, J; Diop, MM; Harman, CL; Hayashi, SM; Krammer, G; Li, X; Llewellyn, C; Mendes, O; Renskers, KJ; Schnabel, J; Smith, BPC; Taylor, SV, 2018)	1.45
"Piperine has been widely used as a bioenhancer. "	( Bioanalytical method development and its application to pharmacokinetics studies on Simvastatin in the presence of piperine and two of its synthetic derivatives. Auti, P; Gabhe, S; Mahadik, K, 2019)	2.17
"Piperine has been reported to have broad bioactive properties ranging from antimicrobial, antidepressant, anti-inflammatory, antioxidative to anticancer activities."	( Piperine production by endophytic fungus Colletotrichum gloeosporioides isolated from Piper nigrum. Chithra, S; Jasim, B; Jyothis, M; Radhakrishnan, EK; Sachidanandan, P, 2014)	2.57
"Piperine has been shown to have anti-inflammatory properties. "	( Piperine inhibits type II phosphatidylinositol 4-kinases: a key component in phosphoinositides turnover. Bojjireddy, N; Sinha, RK; Subrahmanyam, G, 2014)	3.29
"Piperine has been reported to have protective effect on brain."	( Ameliorating effect of piperine on behavioral abnormalities and oxidative markers in sodium valproate induced autism in BALB/C mice. Kameshwari, JS; Pragnya, B; Veeresh, B, 2014)	1.43
"Piperine has been shown to have anti-oxidant, anti-depressant, anti-tumor, and anti-inflammatory activities."	( The inhibitory effect of piperine from Fructus piperis extract on the degranulation of RBL-2H3 cells. Cao, J; Chen, Q; Han, S; Huang, J; Wang, S; Zhang, T, 2014)	1.43
"Piperine (PIP) has been reported to exhibit anti-inflammatory, anti-histaminic, and immunomodulatory activities; however, its antiallergic profile has not been studied."	( Antiallergic effect of piperine on ovalbumin-induced allergic rhinitis in mice. Aswar, M; Aswar, U; Chepurwar, S; Shintre, S, 2015)	1.45
"Piperine has antispasmodic activities, but its anti-secretory effect is not known."	( Inhibition of intestinal chloride secretion by piperine as a cellular basis for the anti-secretory effect of black peppers. Chatsudthipong, V; Kumpun, S; Muanprasat, C; Pongkorpsakol, P; Wongkrasant, P, 2015)	1.4
"Piperine has many pharmacological effects and several health benefits, especially against chronic diseases, such as reduction of insulin-resistance, anti-inflammatory effects, and improvement of hepatic steatosis."	( Piperine and Its Role in Chronic Diseases. Derosa, G; Maffioli, P; Sahebkar, A, )	2.3
"Piperine (PIP) has been reported to enhance the bioavailability of curcumin, but the underlying mechanism remains poorly understood."	( Selective reduction in the expression of UGTs and SULTs, a novel mechanism by which piperine enhances the bioavailability of curcumin in rat. Cai, D; Chen, Y; Chen, Z; Gan, H; Huang, D; Huang, X; Sun, D; Yao, N; Zeng, Q; Zeng, X; Zhang, C; Zhao, Z; Zhong, G; Zhuo, J, 2017)	1.4
"Piperine (PIP) has been found to inhibit P-glycoprotein (P-gp) function in rats, suggesting that it may have the potential to modulate P-gp-mediated drug efflux in humans. "	( The influence of piperine on the pharmacokinetics of fexofenadine, a P-glycoprotein substrate, in healthy volunteers. Bedada, SK; Boga, PK, 2017)	2.24
"Piperine has several well-documented anti-inflammatory properties; however, little is known regarding its effect on humoral immunity. "	( Piperine, a Pungent Alkaloid from Black Pepper, Inhibits B Lymphocyte Activation and Effector Functions. Doucette, CD; Hoskin, DW; Liwski, RS; Soutar, DA, 2017)	3.34
"Piperine has the protective effect on neuroblastoma cells and increased proliferation of hippocampus neural progenitor cells."	( [Antidepressant-like effects of piperine and its neuroprotective mechanism]. Hu, Y; Liao, H; Lin, H; Liu, P; Wang, D, 2009)	1.36
"Piperine has been identified as the main compound in the extract."	( Determination of cytotoxic compounds of Thai traditional medicine called Benjakul using HPLC. Itharat, A; Sakpakdeejaroen, I, 2010)	1.08
"Piperine has been shown to modulate the immune response, but the mechanism underlying this modulation remains unknown."	( Piperine inhibits lipopolysaccharide-induced maturation of bone-marrow-derived dendritic cells through inhibition of ERK and JNK activation. Bae, GS; Cho, JH; Choi, SB; Hong, SH; Jo, IJ; Jung, WS; Kim, JJ; Koo, BS; Lee, CH; Park, KC; Park, SJ; Shin, YK; Song, HJ, 2012)	2.54
"Piperine has been demonstrated in in vitro studies to protect against oxidative damage by inhibiting or quenching free radicals and reactive oxygen species."	( Black pepper and its pungent principle-piperine: a review of diverse physiological effects. Srinivasan, K, 2007)	1.33

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"Piperine inhibit Candida albicans growth (planktonic and biofilm) significantly in our study. "	( Oxidative stress induced by piperine leads to apoptosis in Candida albicans. Jadhav, V; Karuppayil, SM; Kazi, R; Kharat, K; Patil, R; Shelar, A; Thakre, A; Zore, G, 2021)	2.36
"Piperine displays numerous pharmacological effects such as antiproliferative, antitumor, antiangiogenesis, antioxidant, antidiabetic, anti-obesity, cardioprotective, antimicrobial, antiaging, and immunomodulatory effects in various in vitro and in vivo experimental trials."	( Piperine: A review of its biological effects. Gondal, TA; Haq, IU; Imran, M; Mubarak, MS; Nadeem, M; Tufail, T, 2021)	2.79
"Piperine displays significant immunomodulating, antioxidant, chemopreventive and anticancer activity; these effects have been shown to be dose-dependent and tissue-specific."	( Piperine: Old Spice and New Nutraceutical? Ackova, DG; Atalay, M; Cvetkovski, A; Ruskovska, T; Smilkov, K; Vidovic, B, 2019)	2.68
"Piperine could activate transient receptor potential cation channel subfamily V member 1 (TRPV1) receptor, and the rapid activation of whole-cell currents is antagonized by the competitive TRPV1 antagonist capsazepine."	( Piperine exerts anti-seizure effects via the TRPV1 receptor in mice. Chen, CR; Chen, CY; Li, W; Qu, KP, 2013)	2.55
"Piperine may enhance TRAIL-based therapeutics for TNBC."	( Piperine enhances the efficacy of TRAIL-based therapy for triple-negative breast cancer cells. Abdelhamed, S; Awale, S; Ogura, K; Refaat, A; Saiki, I; Yagita, H; Yokoyama, S, 2014)	3.29
"Piperine displays significantly protective effects on inflammation, alveolar bone loss, bone microstructures and collagen fiber degradation in experimental periodontitis. "	( Piperine inhibit inflammation, alveolar bone loss and collagen fibers breakdown in a rat periodontitis model. Dong, Y; Huihui, Z; Li, C, 2015)	3.3
"Piperine can increase curcumin's bioavailability, thereby enhancing the effect of curcumin."	( Combination of curcumin and piperine prevents formation of gallstones in C57BL6 mice fed on lithogenic diet: whether NPC1L1/SREBP2 participates in this process? Li, M; Li, Y; Tian, Y; Wu, S, 2015)	1.43
"Piperine-induced increase of mTORC1 activity in resident peritoneal macrophages (pMΦs) is correlated with enhanced production of IL-6 and TNF-α upon LPS stimulation."	( Piperine metabolically regulates peritoneal resident macrophages to potentiate their functions against bacterial infection. He, XH; Hou, XF; Huang, MY; Lin, QR; Ouyang, DY; Pan, H; Shi, ZJ; Xu, LH; Zha, QB; Zhao, GX, 2015)	2.58
"Piperine could inhibit the nitrite production by in vitro activated macrophages (116.25 microM) to the normal level (15.67 microM) at concentration of 5 microg/mL."	( Effect of piperine on the inhibition of nitric oxide (NO) and TNF-alpha production. Kuttan, G; Pradeep, CR, 2003)	1.44
"Piperine is known to enhance the bioavailability of curcumin, as a substrate of P-gp by at least 2000%."	( A plausible explanation for enhanced bioavailability of P-gp substrates in presence of piperine: simulation for next generation of P-gp inhibitors. Godbole, MM; Misra, K; Singh, DV, 2013)	1.33
"Piperine appeared to increase EGCG bioavailability by inhibiting glucuronidation and gastrointestinal transit."	( Piperine enhances the bioavailability of the tea polyphenol (-)-epigallocatechin-3-gallate in mice. Hong, J; Kim, DH; Lambert, JD; Mishin, VM; Yang, CS, 2004)	2.49
"Piperine could inhibit the matrix metalloproteinase production which was demonstrated by zymographic analysis."	( Piperine is a potent inhibitor of nuclear factor-kappaB (NF-kappaB), c-Fos, CREB, ATF-2 and proinflammatory cytokine gene expression in B16F-10 melanoma cells. Kuttan, G; Pradeep, CR, 2004)	2.49
"Piperine displays antipyretic, analgesic, insecticidal and anti-inflammatory activities. "	( Piperine inhibits TNF-alpha induced adhesion of neutrophils to endothelial monolayer through suppression of NF-kappaB and IkappaB kinase activation. Ghosh, B; Kumar, S; Rembhotkar, GW; Roshan, R; Sharma, A; Singhal, V, 2007)	3.23
"Piperine at lower concentrations (< 50 microM) did not affect the RCR and ADP:O ratios, state 4 and 3 respirations supported by site-specific substrates, viz."	( Effects of piperine on enzyme activities and bioenergetic functions in isolated rat liver mitochondria and hepatocytes. Jamwal, DS; Singh, J, 1993)	1.4
"Piperine showed a lower hepatoprotective potency than silymarin."	( Evaluation of the liver protective potential of piperine, an active principle of black and long peppers. Kapil, A; Koul, IB, 1993)	1.26
"Piperine was found to inhibit state 3 and DNP-stimulated respiration by mitochondria respiring with glutamate plus malate or succinate as substrates."	( Effects of piperine on bioenergetic functions of isolated rat liver mitochondria. Chudapongse, P; Dhumma-Upakorn, P; Janthasoot, W; Reanmongkol, W; Wattanatorn, W, 1988)	1.39

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"Piperine treatment significantly inhibited histological damage in the pancreas, increased the pancreatic acinar cell survival, reduced collagen deposition and reduced pro‑inflammatory cytokines and chemokines."	( Piperine ameliorates the severity of fibrosis via inhibition of TGF‑β/SMAD signaling in a mouse model of chronic pancreatitis. Bae, GS; Choi, JW; Jo, IJ; Kim, DG; Kim, MJ; Lee, SK; Park, SJ; Shin, JY; Song, HJ; Zhou, Z, 2019)	2.68
"Piperine treatment significantly reduced the gene expression level of TNF-α, IL1-β, NF-κB, and glial activation in the injured area; however, the mRNA level of IL-10, Foxp3, BDNF and MBP were significantly increased."	( Piperine ameliorated memory impairment and myelin damage in lysolecethin induced hippocampal demyelination. Dehghan, S; Elahdadi Salmani, M; Javan, M; Nazari, A; Pourabdolhossein, F; Roshanbakhsh, H, 2020)	2.72
"Piperine pretreatment significantly prevented these changes in ISO treated group."	( The protective effect of piperine against isoproterenol-induced inflammation in experimental models of myocardial toxicity. Aliev, G; Beeraka, NM; Chubarev, VN; Dhivya, V; Gavryushova, LV; Huang, CY; Mikhaleva, LM; Minyaeva, NN; Tarasov, VV; Viswanadha, VP, 2020)	1.58
"Piperine and MMC co-treatment resulted in a dose-dependent suppression of the cell proliferation."	( Piperine (PP) enhanced mitomycin-C (MMC) therapy of human cervical cancer through suppressing Bcl-2 signaling pathway via inactivating STAT3/NF-κB. Cui, LD; Han, SZ; Liu, HX; Xu, Y; Yang, LQ, 2017)	2.62
"Piperine treatment also disrupted androgen receptor (AR) expression in LNCaP prostate cancer cells."	( Piperine, a Bioactive Component of Pepper Spice Exerts Therapeutic Effects on Androgen Dependent and Androgen Independent Prostate Cancer Cells. Bartik, MM; Chen, A; Dakshinamoorthy, G; Johnson, GL; Kalyanasundaram, R; Munirathinam, G; Samykutty, A; Shetty, AV; Webb, B; Zheng, G, 2013)	2.55
"Piperine treatment resulted in a dose-dependent inhibition of the proliferation of these cell lines."	( Piperine inhibits the proliferation of human prostate cancer cells via induction of cell cycle arrest and autophagy. He, XH; Liu, KP; Ouyang, DY; Pan, H; Wang, Y; Xu, LH; Zeng, LH, 2013)	2.55
"Piperine treatment also significantly decreased immobility time in the forced swim test in naive mice."	( Brain-derived neurotrophic factor signalling mediates the antidepressant-like effect of piperine in chronically stressed mice. Huang, Z; Ip, SP; Mao, QQ; Xian, YF; Zhong, XM, 2014)	1.35
"Piperine treatment inhibited the growth of SK MEL 28 and B16 F0 cells in a dose and time-dependent manner."	( Piperine causes G1 phase cell cycle arrest and apoptosis in melanoma cells through checkpoint kinase-1 activation. Fofaria, NM; Kim, SH; Srivastava, SK, 2014)	2.57
"Piperine-treated HT-29 cells showed loss of mitochondrial membrane integrity and cleavage of poly (ADP-ribose) polymerase-1, as well as caspase activation and reduced apoptosis in the presence of the pan-caspase inhibitor zVAD-FMK."	( Piperine, an alkaloid from black pepper, inhibits growth of human colon cancer cells via G1 arrest and apoptosis triggered by endoplasmic reticulum stress. Doucette, CD; Hoskin, DW; Power Coombs, MR; Walsh, M; Yaffe, PB, 2015)	2.58
"Piperine pre-treatment decreased the levels of serum markers, lipid peroxidation and PCC with increased antioxidant status in the heart tissues of ISO administered rats."	( Piperine modulates isoproterenol induced myocardial ischemia through antioxidant and anti-dyslipidemic effect in male Wistar rats. Chirayil, HT; Dhivya, V; Huang, CY; Padma, VV; Priya, LB; Sathiskumar, S, 2017)	2.62
"Piperine-treated groups had suppressed eosinophil infiltration, allergic airway inflammation and airway hyperresponsiveness, and these occurred by suppression of the production of interleukin-4, interleukin-5, immunoglobulin E and histamine. "	( Piperine inhibits eosinophil infiltration and airway hyperresponsiveness by suppressing T cell activity and Th2 cytokine production in the ovalbumin-induced asthma model. Kim, SH; Lee, YC, 2009)	3.24
"Piperine treatment also significantly potentiated the number of head-twitches of mice induced by 5-HTP (a metabolic precursor to 5-HT)."	( Involvement of serotonergic system in the antidepressant-like effect of piperine. Che, CT; Ip, SP; Mao, QQ; Xian, YF, 2011)	1.32
"Piperine (1 μM) co-treatment also significantly decreased intracellular reactive oxygen species level, and enhanced superoxide dismutase activity and total glutathione level in corticosterone-treated PC12 cells."	( Protective effects of piperine against corticosterone-induced neurotoxicity in PC12 cells. Che, CT; Huang, Z; Ip, SP; Mao, QQ; Xian, YF, 2012)	1.41
"The piperine-treated animals even survived the experiment (90 days)."	( Effect of piperine on the inhibition of lung metastasis induced B16F-10 melanoma cells in mice. Kuttan, G; Pradeep, CR, 2002)	1.2
"Piperine treatment significantly reduced the above proinflammatory cytokines."	( Piperine is a potent inhibitor of nuclear factor-kappaB (NF-kappaB), c-Fos, CREB, ATF-2 and proinflammatory cytokine gene expression in B16F-10 melanoma cells. Kuttan, G; Pradeep, CR, 2004)	2.49
"Piperine treatment revealed a differential effect on the cytotoxicity of MPP(+) and had its maximum inhibitory effect at 1 microM."	( Piperine inhibition of 1-methyl-4-phenylpyridinium-induced mitochondrial dysfunction and cell death in PC12 cells. Han, ES; Kim, YK; Lee, CS, 2006)	2.5
"Piperine pretreatment potentiated the hepatotoxicity of CCl4 in a dose-dependent manner."	( Potentiation of carbon tetrachloride hepatotoxicity by piperine. Kingkaeohoi, S; Piyachaturawat, P; Toskulkao, C, 1995)	1.26
"Piperine treatment with carcinogens resulted in inhibition of thiobarbituric reactive substances."	( Piperine modulation of carcinogen induced oxidative stress in intestinal mucosa. Bedi, KL; Khajuria, A; Thusu, N; Zutshi, U, 1998)	2.46
"Piperine treatment depleted the total lipid content which was mainly due to the diminution of the total phospholipid concentration."	( Effects of piperine on the lipid composition and enzymes of the pyruvate-malate cycle in the testis of the rat in vivo. Aruldhas, MM; Arunakaran, J; Govindarajulu, P; Malini, T, 1999)	1.41
"Piperine treatment of normal rats enhanced hepatic GSSG concentration by 100% and decreased renal GSH concentration by 35% and renal glutathione reductase activity by 25% when compared to normal controls."	( Effects of piperine on antioxidant pathways in tissues from normal and streptozotocin-induced diabetic rats. Rauscher, FM; Sanders, RA; Watkins, JB, 2000)	1.42
"Piperine-treated rat liver microsomes demonstrated a tendency to enhance [3H]AFB1 binding to calf thymus DNA in vivo."	( Piperine, a plant alkaloid of the piper species, enhances the bioavailability of aflatoxin B1 in rat tissues. Allameh, A; Biswas, G; Raj, HG; Saxena, M; Singh, J; Srivastava, N, 1992)	2.45
"Piperine treatment in rats, treated chronically with phenobarbitone, significantly potentiated pentobarbitone sleeping time, as compared to the controls."	( Effect of piperine on pentobarbitone induced hypnosis in rats. Deshmukh, VK; Dhuley, JN; Mujumdar, AM; Naik, SR; Raman, PH; Thorat, SL, 1990)	1.4
"Pretreatment with piperine suppressed the activation of phosphorylated p38, JNK, and AP-1 as well as the levels of COX-2/PGE"	( Antioxidant and anti-inflammatory effects of piperine on UV-B-irradiated human HaCaT keratinocyte cells. Jaisin, Y; Malaniyom, K; Natewong, S; Ratanachamnong, P; Watthammawut, A; Wongsawatkul, O, 2020)	1.14
"Treatment with Piperine markedly inhibited poly(ADP-ribose) polymerase activation, pro-apoptotic Bax levels and elevation of Bcl-2 levels."	( Anti-apoptotic and anti-inflammatory effect of Piperine on 6-OHDA induced Parkinson's rat model. Ahmad, A; Ishrat, T; Islam, F; Khan, A; Khan, MM; Safhi, MM; Shrivastava, P; Tabassum, R; Vaibhav, K, 2013)	0.99
"Treatment with piperine (6.25-25 microM) for 72 h reversed the CORT-induced reduction of BDNF mRNA expression in cultured hippocampal neurons."	( Antidepressant like effects of piperine in chronic mild stress treated mice and its possible mechanisms. Li, S; Li, W; Matsumoto, K; Tang, Y; Wang, C; Wang, M, 2007)	0.97
"Pretreatment with piperine for 2 hr had no significant effect (P > 0.05)."	( Modulatory effect of piperine on benzo[a]pyrene cytotoxicity and DNA adduct formation in V-79 lung fibroblast cells. Chang, JP; Chu, CY; Wang, CJ, 1994)	0.93
"Pretreatment with piperine or oxyphenylbutazone reduced the liver lipid peroxidation, acid phosphatase and oedema induced by carrageenin."	( Inhibition of lipid peroxidation by piperine during experimental inflammation in rats. Dhuley, JN; Mujumdar, AM; Naik, SR; Raman, PH, 1993)	0.88
"Treatment with piperine reversed the diabetic effects on GSSG concentration in brain, on renal glutathione peroxidase and superoxide dismutase activities, and on cardiac glutathione reductase activity and lipid peroxidation."	( Effects of piperine on antioxidant pathways in tissues from normal and streptozotocin-induced diabetic rats. Rauscher, FM; Sanders, RA; Watkins, JB, 2000)	1.04
"Pretreatment with piperine prolonged hexobarbital sleeping time and zoxazolamine paralysis time in mice at half the dose of SKF-525A."	( Biochemical basis of enhanced drug bioavailability by piperine: evidence that piperine is a potent inhibitor of drug metabolism. Atal, CK; Dubey, RK; Singh, J, 1985)	0.84

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"Piperine is acutely toxic to mice, rats and hamsters."	( Acute and subacute toxicity of piperine in mice, rats and hamsters. Glinsukon, T; Piyachaturawat, P; Toskulkao, C, 1983)	1.99
" Piperine itself was not toxic to the cells up to a concentration of almost 100 microM."	( Piperine, a major ingredient of black and long peppers, protects against AFB1-induced cytotoxicity and micronuclei formation in H4IIEC3 rat hepatoma cells. Reen, RK; Singh, J; Wiebel, FJ, 1994)	2.64
" Piperine at 60 microM completely counteracted cytotoxicity and formation of MN by 10 microM AFB1 and reduced the toxic effects of 20 microM AFB1 by > 50%."	( Piperine inhibits aflatoxin B1-induced cytotoxicity and genotoxicity in V79 Chinese hamster cells genetically engineered to express rat cytochrome P4502B1. Reen, RK; Singh, J; Wiebel, FJ, 1997)	2.65
" Results from the present study suggest a better therapeutic index for the nimesulide-piperine combination indicating that this combination would further reduce the frequency of adverse effects associated with nimesulide alone."	( Comparative anti-nociceptive, anti-inflammatory and toxicity profile of nimesulide vs nimesulide and piperine combination. Bansal, P; Bhardwaj, RK; Gupta, SK; Velpandian, T, 2000)	0.75
" The present study investigates the molecular etiology of haloperidol neurotoxicity and the role of curcumin, a well-known anti-oxidant, in ameliorating these adverse effects."	( Protective effect of curcumin and its combination with piperine (bioavailability enhancer) against haloperidol-associated neurotoxicity: cellular and neurochemical evidence. Bishnoi, M; Chopra, K; Kulkarni, SK; Rongzhu, L, 2011)	0.62
" The spleen cells appear more susceptible to the adverse effects of DLM than thymus cells."	( Mechanism of deltamethrin induced thymic and splenic toxicity in mice and its protection by piperine and curcumin: in vivo study. Kumar, A; Sasmal, D; Sharma, N, 2018)	0.7
" Higher percentages of adverse events were detected in groups 2 (31."	( Efficacy and safety of resveratrol, an oral hemoglobin F-augmenting agent, in patients with beta-thalassemia intermedia. Bordbar, M; Eshghi, P; Haghpanah, S; Hoormand, M; Karimi, M; Zarei, T; Zekavat, O, 2018)	0.48
" Piperine has been determined safe under conditions of intended use as a flavoring substance by regulatory and scientific expert bodies."	( Absence of adverse effects following administration of piperine in the diet of Sprague-Dawley rats for 90 days. Aubanel, M; Bastaki, M; Bauter, M; Cachet, T; Demyttenaere, J; Diop, MM; Harman, CL; Hayashi, SM; Krammer, G; Li, X; Llewellyn, C; Mendes, O; Renskers, KJ; Schnabel, J; Smith, BPC; Taylor, SV, 2018)	1.64
" This study employs bioactive surfactants in the common safe doses to improve PIP targeting to the brain."	( Oral Brain-Targeted Microemulsion for Enhanced Piperine Delivery in Alzheimer's Disease Therapy: In Vitro Appraisal, In Vivo Activity, and Nanotoxicity. Abdallah, OY; Abdelmonsif, DA; Elnaggar, YSR; Etman, SM, 2018)	0.74

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" An earlier tmax and a higher Cmax and AUC were observed in the subjects who received piperine and propranolol."	( Effect of piperine on bioavailability and pharmacokinetics of propranolol and theophylline in healthy volunteers. Bano, G; Bedi, KL; Johri, RK; Raina, RK; Sharma, SC; Zutshi, U, 1991)	0.91
" A pharmacokinetic study was performed in rabbits and tissue distribution studies were carried out in rats."	( Pharmacokinetics and tissue distribution of piperine in animals after i.v. bolus administration. Mada, SR; Sunkara, G; Vobalaboina, V, 2001)	0.57
" A preliminary pharmacokinetic study was carried out in mice by administering phenytoin (10 mg) orally, with or without piperine (0."	( Piperine in food: interference in the pharmacokinetics of phenytoin. Bhardwaj, RK; Gupta, SK; Jaiswal, J; Jasuja, R; Velpandian, T, )	1.78
" The improved bioavailability is reflected in various pharmacokinetic parameters viz."	( Effect of co-administration of piperine on pharmacokinetics of beta-lactam antibiotics in rats. Dhuley, JN; Hiwale, AR; Naik, SR, 2002)	0.6
" The mean plasma drug concentrations at different time points and the pharmacokinetic parameters before and after piperine administration were compared by Student's t-test."	( Effect of piperine on the steady-state pharmacokinetics of phenytoin in patients with epilepsy. Hota, D; Kharbanda, P; Pandhi, P; Pattanaik, S; Prabhakar, S, 2006)	0.95
" Blood samples were collected from 1 to 144 hours post-dose for pharmacokinetic analysis."	( Influence of piperine on the pharmacokinetics of nevirapine under fasting conditions: a randomised, crossover, placebo-controlled study. Kasibhatta, R; Naidu, MU, 2007)	0.71
"The purpose of this study was to estimate the pharmacokinetic parameters and tissue distribution of positively charged stearylamine (LN-P-SA) and pegylated lipid nanospheres (LN-P-PEG) of piperine in BALB/c mice."	( Pharmacokinetics and tissue distribution of piperine lipid nanospheres. Veerareddy, PR; Vobalaboina, V, 2008)	0.8
" The pharmacokinetic parameters were compared by Students t-test."	( Pharmacokinetic interaction of single dose of piperine with steady-state carbamazepine in epilepsy patients. Hota, D; Kharbanda, P; Pandhi, P; Pattanaik, S; Prabhakar, S, 2009)	0.61
" The aim of this study was to determine whether a commercially available curcuminoid/piperine extract alters the pharmacokinetic disposition of probe drugs for these enzymes in human volunteers."	( Effect of a herbal extract containing curcumin and piperine on midazolam, flurbiprofen and paracetamol (acetaminophen) pharmacokinetics in healthy volunteers. Badmaev, V; Court, MH; Greenblatt, DJ; Hanley, MJ; Harmatz, JS; Hazarika, S; Majeed, M; Masse, G; Volak, LP, 2013)	0.87
" In normal and streptozotocin induced diabetic rats the combination of glimepiride with piperine increased all the pharmacokinetic parameters, such as Cmax, AUC0-n, AUCtotal, t1/2, and MRT, and decreased the clearance, Vd, markedly as compared with the control group."	( Effect of piperine on the pharmacokinetics and pharmacodynamics of glimepiride in normal and streptozotocin-induced diabetic rats. Rani, TS; Sujatha, S; Veeresham, C, 2012)	1
"The purpose of this study was to investigate the potential pharmacokinetic interactions with natural products (such as piperine (PIP), gallic acid (GA) and cinnamic acid (CA)) and rosuvastatin (RSV) (a specific breast cancer resistance protein, BCRP substrate) in rats."	( Effects of piperine, cinnamic acid and gallic acid on rosuvastatin pharmacokinetics in rats. Basu, S; Jana, S; Patel, H; Patel, VB, 2013)	0.99
"Only one kind of synthesized alkaloid, piperlonguminine, was used to understand the interference of the other alkaloids in pharmacokinetic study using HPLC/UV in rat plasma after oral administration."	( LC analysis and pharmacokinetic study of synthetic piperlonguminine in rat plasma after oral administration. Baigude, H; Borjihan, G; Sarnaizul, E, 2013)	0.39
" Then, the pharmacokinetic profiles of linarin in rats after oral administration of linarin (50 mg/kg) alone and in combination with piperine (20 mg/kg) were determined using a validated LC-MS/MS method."	( Effects of piperine on the intestinal permeability and pharmacokinetics of linarin in rats. Di, X; Feng, X; Liu, Y; Wang, X, 2014)	1
"05) increase in the maximum plasma concentration (Cmax), the mean area under the plasma concentration-time curve (AUC), and the elimination half-life (t1/2) of domperidone as compared to those obtained for domperidone alone."	( Effect of piperine, a major component of black pepper, on the pharmacokinetics of domperidone in rats. Alhumayyd, MS; Almotrefi, AA; Bukhari, IA, 2014)	0.8
" The pharmacokinetic profiles of emodin after oral administration of emodin (20mg/kg) alone and in combination with piperine (20mg/kg) to rats were investigated via a validated LC/MS/MS method."	( Effect of piperine on the bioavailability and pharmacokinetics of emodin in rats. Di, X; Liu, Y; Wang, X, 2015)	1.03
" The pharmacokinetic profile of DTX was exceptionally improved by the conjugation, in general, and coadministration with piperine, in specific vis-à-vis plain drug."	( Conjugation of Docetaxel with Multiwalled Carbon Nanotubes and Codelivery with Piperine: Implications on Pharmacokinetic Profile and Anticancer Activity. Arora, S; Bhushan, S; Guru, SK; Katare, OP; Kiran, C; Kumar, D; Kumar, M; Kumar, P; Raza, K; Sharma, G, 2016)	0.87
" The method was validated and successfully applied to everted sac and pharmacokinetic studies in rats."	( HPLC Estimation, Ex vivo Everted Sac Permeability and In Vivo Pharmacokinetic Studies of Darunavir. Sangave, PC; Suvarna, VM, 2018)	0.48
" However, there is limited pharmacokinetic information on this compound, especially its distribution in neuronal tissue and its route of excretion."	( Comparative pharmacokinetics of oxyresveratrol alone and in combination with piperine as a bioenhancer in rats. Anukunwithaya, T; Junsaeng, D; Khemawoot, P; Likhitwitayawuid, K; Songvut, P; Sritularak, B, 2019)	0.74
"The addition of piperine could enhance some of the pharmacokinetic properties of oxyresveratrol via both intravenous and oral administration."	( Comparative pharmacokinetics of oxyresveratrol alone and in combination with piperine as a bioenhancer in rats. Anukunwithaya, T; Junsaeng, D; Khemawoot, P; Likhitwitayawuid, K; Songvut, P; Sritularak, B, 2019)	1.09
" The pharmacokinetic (PK) interactions studies on co-administration of ATR (8."	( Pharmacokinetics and Pharmacodynamic Herb-Drug Interaction of Piperine with Atorvastatin in Rats. Choudhary, DC; Nagrik, SS; Raje, A; Thomas, AB, 2021)	0.86
" In this study, the pharmacokinetic profiles and metabolomic changes generated by the bioactive triterpenoids of Centell-S alone, and in combination with the bioenhancers piperine and curcumin, were investigated in beagle dogs."	( Bioenhancing effects of piperine and curcumin on triterpenoid pharmacokinetics and neurodegenerative metabolomes from Centella asiatica extract in beagle dogs. Boonyarattanasoonthorn, T; Hamlin, R; Khemawoot, P; Kijtawornrat, A; Kongratanapasert, T; Maiuthed, A, 2022)	1.22

Excerpt	Reference	Relevance
" These effects were also observed in vivo, where the combination with piplartine but not piperine with 5-FU led to a higher tumor growth inhibition."	( In vitro and in vivo antitumor effect of 5-FU combined with piplartine and piperine. Alves, AP; Bezerra, DP; Costa-Lotufo, LV; de Alencar, NM; de Castro, FO; de Moraes, MO; Elmiro, FJ; Lima, MA; Lima, MW; Mesquita, RO; Pessoa, C; Silveira, ER, 2008)	0.8
" The in vivo pharmacokinetics revealed that curcumin entrapped nanoparticles demonstrate at least 9-fold increase in oral bioavailability when compared to curcumin administered with piperine as absorption enhancer."	( Nanoparticle encapsulation improves oral bioavailability of curcumin by at least 9-fold when compared to curcumin administered with piperine as absorption enhancer. Ankola, DD; Beniwal, V; Kumar, MN; Shaikh, J; Singh, D, 2009)	0.75
" (Amaranthaceae) root alone and in combination with piperine in treating ulcerative colitis (UC) in mice."	( Amaranthus roxburghianus root extract in combination with piperine as a potential treatment of ulcerative colitis in mice. Bhawar, SB; Ingale, JM; Nirmal, SA; Pattan, SR, 2013)	0.88
" The present study examined the synergistic effect of low doses of FA combined with subthreshold dose of piperine, a bioavailability enhancer, on depression-like behaviors in mice, and investigated the possible mechanism."	( Synergistic antidepressant-like effect of ferulic acid in combination with piperine: involvement of monoaminergic system. Chen, J; Chen, L; Chen, R; Huang, W; Li, G; Pan, J; Reed, M; Ruan, L; Wang, R; Xie, X; Xu, Y; Yan, Q; Zhang, M, 2015)	0.86
" Although curcumin caused already significant effects, the combination with piperine completely suppressed the osteoclastogenesis by decreasing the TRAP activity and inhibiting the expression of the specific osteoclast markers TRAP, cathepsin K, and calcitonin receptor."	( Curcumin in Combination with Piperine Suppresses Osteoclastogenesis In Vitro. Geurtsen, W; Leyhausen, G; Martins, CA; Volk, J, 2015)	0.94
"We demonstrated that curcumin combined with piperine suppressed the osteoclastogenesis in vitro without causing cytotoxic effects in periodontal ligament cells."	( Curcumin in Combination with Piperine Suppresses Osteoclastogenesis In Vitro. Geurtsen, W; Leyhausen, G; Martins, CA; Volk, J, 2015)	0.97
" Nevertheless, the effect of such drug combination usage on the in vivo exposure of PIP has not been investigated due to lack of assay for the simultaneous determination of PIP and other drugs such as DOX."	( Non-linear pharmacokinetics of piperine and its herb-drug interactions with docetaxel in Sprague-Dawley rats. Chow, MSS; Lam, CWK; Li, C; Ren, T; Wang, Q; Zhang, Y; Zuo, Z, 2016)	0.72
" Curcumin (CMN) in combination with bioenhancer piperine (PP) in 6-hydroxydopamine-induced Parkinsonian rats was used to investigate the antioxidant, neuromodulatory and neuroprotective mechanisms."	( Neuroprotective potential of curcumin in combination with piperine against 6-hydroxy dopamine induced motor deficit and neurochemical alterations in rats. Kumar, P; Singh, S, 2017)	0.95
" Quercetin (QC) in combination with piperine (bioenhancer) acts as potential antioxidant, anti-inflammatory and neuroprotective against 6-OHDA rat model of PD."	( Piperine in combination with quercetin halt 6-OHDA induced neurodegeneration in experimental rats: Biochemical and neurochemical evidences. Kumar, P; Singh, S, 2018)	2.2
" For the first time, this study was aimed to evaluate the effect of topical piperine combined with narrowband ultraviolet B (NB-UVB) on vitiligo treatment."	( The effect of topical piperine combined with narrowband UVB on vitiligo treatment: A clinical trial study. Abadi, A; Hoormand, M; Shafiee, A; Shahidi-Dadras, M, 2018)	1.03
" The results of the systematic review showed that piperine has promising anti-TB activity, mainly when combined with antimicrobials, and plays an important role as an EP inhibitor."	( Promising Antituberculosis Activity of Piperine Combined with Antimicrobials: A Systematic Review. Almeida, AL; Barros, ILE; Caleffi-Ferracioli, KR; Campanerut-Sá, PAZ; Canezin, PH; Cardoso, RF; Hegeto, LA; Nakamura de Vasconcelos, SS; Perez de Souza, J; Scodro, RBL; Siqueira, VLD; Teixeira, JJV, )	0.65
" The aim of this study was to investigate the pharmacokinetic profiles of oxyresveratrol alone and in combination with piperine as a bioenhancer in rats."	( Comparative pharmacokinetics of oxyresveratrol alone and in combination with piperine as a bioenhancer in rats. Anukunwithaya, T; Junsaeng, D; Khemawoot, P; Likhitwitayawuid, K; Songvut, P; Sritularak, B, 2019)	0.95
"Male Wistar rats were administered with oxyresveratrol 10 mg/kg, oxyresveratrol 10 mg/kg plus piperine 1 mg/kg via intravenous or oxyresveratrol 100 mg/kg, oxyresveratrol 100 mg/kg plus piperine 10 mg/kg via oral gavage."	( Comparative pharmacokinetics of oxyresveratrol alone and in combination with piperine as a bioenhancer in rats. Anukunwithaya, T; Junsaeng, D; Khemawoot, P; Likhitwitayawuid, K; Songvut, P; Sritularak, B, 2019)	0.96
"The combination with piperine had shown a significantly higher maximum concentration in plasma approximately 1500 μg/L within 1-2 h after oral dosing, and could increase oral bioavailability of oxyresveratrol approximately 2-fold."	( Comparative pharmacokinetics of oxyresveratrol alone and in combination with piperine as a bioenhancer in rats. Anukunwithaya, T; Junsaeng, D; Khemawoot, P; Likhitwitayawuid, K; Songvut, P; Sritularak, B, 2019)	1.06
" This study was carried out to investigate the effect of piperine and quercetin alone or in combination with marbofloxacin on CYP3A37 and MDR1 mRNA expression levels in liver and intestine of broiler chicken."	( Effect of piperine and quercetin alone or in combination with marbofloxacin on CYP3A37 and MDR1 mRNA expression levels in broiler chickens. Mathapati, BS; Modi, CM; Patel, HB; Patel, UD, 2019)	1.16
" Therefore, the present study was designed to evaluate the neuroprotective effect of quercetin in combination with piperine against rotenone- and iron supplement-induced model of PD."	( Neuroprotective Effect of Quercetin in Combination with Piperine Against Rotenone- and Iron Supplement-Induced Parkinson's Disease in Experimental Rats. Raj, K; Sharma, S; Singh, S, 2020)	1.01
" After incubation for 2 h, the samples were pretreated and analyzed using liquid chromatography combined with diode-array detection and high-resolution mass spectrometry (LC/DAD-HRMS)."	( Identification of the metabolites of piperine via hepatocyte incubation and liquid chromatography combined with diode-array detection and high-resolution mass spectrometry. Li, M; Li, Y; Tang, J; Wang, Z; Wen, M, 2020)	0.83

Excerpt	Reference	Relevance
"The effect of piperine on the bioavailability and pharmacokinetics of propranolol and theophylline has been examined in a crossover study."	( Effect of piperine on bioavailability and pharmacokinetics of propranolol and theophylline in healthy volunteers. Bano, G; Bedi, KL; Johri, RK; Raina, RK; Sharma, SC; Zutshi, U, 1991)	1.04
" The results suggest that these acrids have the capacity to increase the bioavailability of certain drugs."	( Scientific evidence on the role of Ayurvedic herbals on bioavailability of drugs. Atal, CK; Rao, PG; Zutshi, U, 1981)	0.26
" It is shown to enhance the bioavailability of various structurally and therapeutically diverse drugs."	( Permeability characteristics of piperine on oral absorption--an active alkaloid from peppers and a bioavailability enhancer. Bedi, KL; Khajuria, A; Zutshi, U, 1998)	0.58
" cannot be utilised because of poor bioavailability due to its rapid metabolism in the liver and intestinal wall."	( Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers. Joseph, T; Joy, D; Majeed, M; Rajendran, R; Shoba, G; Srinivas, PS, 1998)	0.67
" Preliminary pharmacokinetic studies conducted by us suggested the increased bioavailability of nimesulide co-administered with piperine."	( Comparative anti-nociceptive, anti-inflammatory and toxicity profile of nimesulide vs nimesulide and piperine combination. Bansal, P; Bhardwaj, RK; Gupta, SK; Velpandian, T, 2000)	0.73
" Thus few novel analogues as CYP inactivators have been synthesized which may have important consequences in pharmacokinetics and bioavailability of drugs."	( Structure-activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities. Dhar, KL; Jamwal, DS; Koul, JL; Koul, S; Reen, RK; Singh, J; Singh, K; Taneja, SC, 2000)	0.58
" Piperine (1) is an alkaloidal constituent of black and long peppers recently established as a bioavailability enhancer of drugs and other substances."	( Antidiarrhoeal activity of piperine in mice. Bajad, S; Bedi, KL; Johri, RK; Singla, AK, 2001)	1.52
"Piperine, a major alkaloid of black and long peppers has been reported to act as bioavailability enhancer of several drugs by inhibiting drug metabolising enzymes and/or by increasing oral absorption."	( Simple high-performance liquid chromatography method for the simultaneous determination of ketoconazole and piperine in rat plasma and hepatocyte culture. Bajad, S; Bedi, KL; Johri, RK; Singh, J; Singh, K, 2002)	1.97
" enhanced bioavailability of beta lactam antibiotics, amoxycillin trihydrate and cefotaxime sodium significantly in rats."	( Effect of co-administration of piperine on pharmacokinetics of beta-lactam antibiotics in rats. Dhuley, JN; Hiwale, AR; Naik, SR, 2002)	0.6
"Potential of piperine, an active alkaloid of black and long peppers, to increase the bioavailability of drugs in humans is of great clinical significance owing to its omnipresence in food."	( Characterization of a new rat urinary metabolite of piperine by LC/NMR/MS studies. Bajad, S; Bedi, KL; Coumar, M; Khajuria, R; Suri, OP, 2003)	0.94
" Previously, we reported the bioavailability of EGCG in rats (1."	( Piperine enhances the bioavailability of the tea polyphenol (-)-epigallocatechin-3-gallate in mice. Hong, J; Kim, DH; Lambert, JD; Mishin, VM; Yang, CS, 2004)	1.77
" These additives increased intestinal permeability (P(app)) and absorption rate constant (K(a)) up to two and fourfold, respectively."	( In situ and in vivo efficacy of peroral absorption enhancers in rats and correlation to in vitro mechanistic studies. Chawla, HP; Panchagnula, R; Sharma, P; Varma, MV, )	0.13
"Piperine, the active principle of Piper longum, Piper nigrum and Zingiber officinalis, has been reported to enhance the oral bioavailability of phenytoin in human volunteers."	( Effect of piperine on the steady-state pharmacokinetics of phenytoin in patients with epilepsy. Hota, D; Kharbanda, P; Pandhi, P; Pattanaik, S; Prabhakar, S, 2006)	2.18
" There are indications that piperine inhibits, rather than stimulates, drug metabolism in most cases, thus increasing the bioavailability and effect of some drugs."	( Influence of piperine on the pharmacokinetics of nevirapine under fasting conditions: a randomised, crossover, placebo-controlled study. Kasibhatta, R; Naidu, MU, 2007)	1
"This pilot study provided evidence for enhanced bioavailability of nevirapine when administered with piperine."	( Influence of piperine on the pharmacokinetics of nevirapine under fasting conditions: a randomised, crossover, placebo-controlled study. Kasibhatta, R; Naidu, MU, 2007)	0.92
" Piperine has been documented to enhance the bioavailability of a number of therapeutic drugs as well as phytochemicals by this very property."	( Black pepper and its pungent principle-piperine: a review of diverse physiological effects. Srinivasan, K, 2007)	1.52
"The present study was designed to investigate the involvement of monoaminergic system(s) in the antidepressant activity of curcumin and the effect of piperine, a bioavailability enhancer, on the bioavailability and biological effects of curcumin."	( Antidepressant activity of curcumin: involvement of serotonin and dopamine system. Bhutani, MK; Bishnoi, M; Kulkarni, SK, 2008)	0.55
" Piperine could significantly enhance the oral bioavailability of carbamazepine, possibly by decreasing the elimination and/or by increasing its absorption."	( Pharmacokinetic interaction of single dose of piperine with steady-state carbamazepine in epilepsy patients. Hota, D; Kharbanda, P; Pandhi, P; Pattanaik, S; Prabhakar, S, 2009)	1.52
" The in vivo pharmacokinetics revealed that curcumin entrapped nanoparticles demonstrate at least 9-fold increase in oral bioavailability when compared to curcumin administered with piperine as absorption enhancer."	( Nanoparticle encapsulation improves oral bioavailability of curcumin by at least 9-fold when compared to curcumin administered with piperine as absorption enhancer. Ankola, DD; Beniwal, V; Kumar, MN; Shaikh, J; Singh, D, 2009)	0.75
" Scanning electronic microscopy of the intestinal villi in these spice treatments revealed alterations in the ultrastructure, especially an increase in microvilli length and perimeter which would mean a beneficial increase in the absorptive surface of the small intestine, providing for an increased bioavailability of micronutrients."	( Beneficial influence of dietary spices on the ultrastructure and fluidity of the intestinal brush border in rats. Prakash, UN; Srinivasan, K, 2010)	0.36
" The bioavailability of fexofenadine was increased by approximately 2-folds via the concomitant use of piperine."	( Effect of piperine, a major component of black pepper, on the intestinal absorption of fexofenadine and its implication on food-drug interaction. Han, HK; Jin, MJ, 2010)	0.98
" Piperine (20 mg/kg orally) was administered along with curcumin to enhance the bioavailability of the latter up to 20-fold more."	( Antioxidant potential of curcumin against oxidative insult induced by pentylenetetrazol in epileptic rats. Jyothy, A; Munshi, A; Nehru, B; Sharma, V, 2010)	1.27
" Enhanced bioavailability of curcumin was evidenced when the same was orally administered concomitant with piperine."	( Tissue distribution & elimination of capsaicin, piperine & curcumin following oral intake in rats. Srinivasan, K; Suresh, D, 2010)	0.83
"Considerable difference exists in the bioavailability of the three test compounds."	( Tissue distribution & elimination of capsaicin, piperine & curcumin following oral intake in rats. Srinivasan, K; Suresh, D, 2010)	0.62
" A liquid chromatography-tandem mass spectrometry method was applied to determine the oral bioavailability of ethyl piperate."	( Contribution of carboxylesterase in hamster to the intestinal first-pass loss and low bioavailability of ethyl piperate, an effective lipid-lowering drug candidate. Bao, N; Borjihan, G; Hu, M; Jia, J; Li, S; Lu, Y; Ma, Y; Wang, Y; Yang, D; Yu, C, 2011)	0.37
"There is currently a need for a better understanding of the mechanisms of food-drug interaction as well as the clinical implication to maximize the effectiveness and applicability of black pepper or its active component, piperine, as a bioavailability enhancer in the clinical arena."	( The effects of black pepper on the intestinal absorption and hepatic metabolism of drugs. Han, HK, 2011)	0.55
" The information provided is used to assess the clinical significance of black pepper and piperine and optimize their effectiveness as a bioavailability enhancer."	( The effects of black pepper on the intestinal absorption and hepatic metabolism of drugs. Han, HK, 2011)	0.59
" Furthermore, the effective formulation strategy for the optimization of the pharmacokinetic characteristics of dietary components is crucial to improve their in vivo performance and ultimately maximize their effectiveness as a bioavailability enhancer."	( The effects of black pepper on the intestinal absorption and hepatic metabolism of drugs. Han, HK, 2011)	0.37
" However, the poor in vivo bioavailability of resveratrol due to its rapid metabolism is being considered as a major obstacle in translating its effects in humans."	( Enhancing the bioavailability of resveratrol by combining it with piperine. Ahmad, N; Bailey, HH; Johnson, JJ; Mukhtar, H; Nihal, M; Scarlett, CO; Siddiqui, IA, 2011)	0.61
"Our study demonstrated that piperine significantly improves the in vivo bioavailability of resveratrol."	( Enhancing the bioavailability of resveratrol by combining it with piperine. Ahmad, N; Bailey, HH; Johnson, JJ; Mukhtar, H; Nihal, M; Scarlett, CO; Siddiqui, IA, 2011)	0.9
" By inhibiting the metabolism of drugs, piperine improves the bioavailability of drugs."	( Influence of piperine on ibuprofen induced antinociception and its pharmacokinetics. Durga, KD; Mullangi, R; Padmavathi, Y; Reddy, BM; Venkatesh, S, 2011)	1.01
"9 mg/kg body weight) or the combination of the both - piperine was used in this combination to enhance the bioavailability of EGCG."	( Green tea polyphenol epigallocatechin-3-gallate shows therapeutic antioxidative effects in a murine model of colitis. Brückner, M; Domschke, W; Kucharzik, T; Lügering, A; Westphal, S, 2012)	0.63
" These results were discussed considering that curcumin may not be well absorbed and it did not reach a level high enough in vivo to overcome the severe hypercholesterolemia and oxidative stress produced by the PC-rich diet."	( Effect of curcumin on LDL oxidation in vitro, and lipid peroxidation and antioxidant enzymes in cholesterol fed rabbits. Kummerow, FA; Mahfouz, MM; Zhou, Q, 2011)	0.37
" By inhibiting the metabolism of drugs, piperine improves the bioavailability of drugs."	( Effect of piperine on antihyperglycemic activity and pharmacokinetic profile of nateglinide. Bommineni, MR; Mullangi, R; Nadipelli, M; Sama, V; Yenumula, P, 2012)	1.05
" Piperine is known to enhance the bioavailability of curcumin, as a substrate of P-gp by at least 2000%."	( A plausible explanation for enhanced bioavailability of P-gp substrates in presence of piperine: simulation for next generation of P-gp inhibitors. Godbole, MM; Misra, K; Singh, DV, 2013)	1.52
"This study investigated the effect of piperine on the gene expression of P-glycoprotein (P-gp) as well as pregnane-X-receptor (PXR) activity and also its implication on the bioavailability of diltiazem, a P-gp substrate."	( Repeated dosing of piperine induced gene expression of P-glycoprotein via stimulated pregnane-X-receptor activity and altered pharmacokinetics of diltiazem in rats. Han, HK; Kang, KW; Qiang, F, 2012)	0.98
" Recent advancement in bioavailability enhancement of drugs by compounds of herbal origin has produced a revolutionary shift in the way of therapeutics."	( A comprehensive review on pharmacotherapeutics of herbal bioenhancers. Awale, MM; Chauhan, BN; Dudhatra, GB; Kamani, DR; Kumar, A; Modi, CM; Mody, SK; Patel, HB, 2012)	0.38
" The results clearly suggest that piperine enhanced the bioavailability of curcumin and potentiated its protective effects against CUS induced cognitive impairment and associated oxidative damage in mice."	( Piperine potentiates the protective effects of curcumin against chronic unpredictable stress-induced cognitive impairment and oxidative damage in mice. Kumar, A; Rinwa, P, 2012)	2.1
" The results revealed that a combination of glimepiride with piperine led to the enhancement of the bioavailability of glimepiride by inhibiting the CYP2C9 enzyme, which suggested that piperine might be beneficial as an adjuvant to glimepiride in a proper dose, in diabetic patients."	( Effect of piperine on the pharmacokinetics and pharmacodynamics of glimepiride in normal and streptozotocin-induced diabetic rats. Rani, TS; Sujatha, S; Veeresham, C, 2012)	1.02
"In view of the wide-spread deficiency of iron and zinc in populations dependent on plant foods, it is desirable to improve the bioavailability of the same."	( Enhanced intestinal uptake of iron, zinc and calcium in rats fed pungent spice principles--piperine, capsaicin and ginger (Zingiber officinale). Prakash, UN; Srinivasan, K, 2013)	0.61
"In this study, we used cubic nanoparticles containing piperine to improve the oral bioavailability of PPD and to enhance its absorption and inhibit its metabolism."	( Enhanced oral absorption of 20(S)-protopanaxadiol by self-assembled liquid crystalline nanoparticles containing piperine: in vitro and in vivo studies. Cheng, XD; Jia, XB; Jin, X; Li, SL; Sun, E; Tan, XB; You, M; Zhang, ZH, 2013)	0.85
"The increased bioavailability of PPD-cubosome loaded with piperine is due to an increase in absorption and inhibition of metabolism of PPD by cubic nanoparticles containing piperine rather than because of improved release of PPD."	( Enhanced oral absorption of 20(S)-protopanaxadiol by self-assembled liquid crystalline nanoparticles containing piperine: in vitro and in vivo studies. Cheng, XD; Jia, XB; Jin, X; Li, SL; Sun, E; Tan, XB; You, M; Zhang, ZH, 2013)	0.85
"To prepare curcumin-piperine (Cu-Pi) nanoparticles by various methods and to study the effect of various manufacturing parameters on Cu-Pi nanoparticles and to identify a suitable method for the preparation of Cu-Pi nanoparticles to overcome oral bioavailability and cancer cell targeting limitations in the treatment of cancer."	( Preparation and characterization of curcumin-piperine dual drug loaded nanoparticles. Kathiresan, K; Krishnan, K; Manavalan, R; Moorthi, C, 2012)	0.96
" This dual nanoparticulate drug delivery system appears to be promising to overcome oral bioavailability and cancer cell targeting limitations in the treatment of cancer."	( Preparation and characterization of curcumin-piperine dual drug loaded nanoparticles. Kathiresan, K; Krishnan, K; Manavalan, R; Moorthi, C, 2012)	0.64
" However, in addition to its culinary uses, pepper has important medicinal and preservative properties, and, more recently, piperine has been shown to have fundamental effects on p-glycoprotein and many enzyme systems, leading to biotransformative effects including chemoprevention, detoxification, and enhancement of the absorption and bioavailability of herbal and conventional drugs."	( Piper nigrum and piperine: an update. Goswami, TK; Meghwal, M, 2013)	0.94
" The dichotomous effects of PIP on induction of CYP3A4 and MDR1 expression observed here and inhibition of their activity reported elsewhere challenges the potential use of PIP as a bioavailability enhancer and suggests that caution should be taken in PIP consumption during drug treatment in patients, particularly those who favor daily pepper spice or rely on certain pepper remedies."	( Piperine activates human pregnane X receptor to induce the expression of cytochrome P450 3A4 and multidrug resistance protein 1. Chai, SC; Chen, T; Lin, W; Ong, SS; Schuetz, EG; Wang, YM; Wu, J, 2013)	1.83
" Bioflavonoids like quercetin are reported to have poor bioavailability and limited therapeutic potential against stress induced neurological disorders."	( Quercetin along with piperine prevents cognitive dysfunction, oxidative stress and neuro-inflammation associated with mouse model of chronic unpredictable stress. Kumar, A; Rinwa, P, 2017)	0.77
" The present study investigated the synergistic antidepressant-like effect of trans-resveratrol and piperine, a bioavailability enhancer, in mice and explored the possible mechanism."	( Piperine potentiates the antidepressant-like effect of trans-resveratrol: involvement of monoaminergic system. Chen, Z; Huang, W; Li, G; Lin, M; Pan, J; Wang, Q; Wu, F; Wu, S; Xie, X; Xu, Y; Yan, Q; Yu, X, 2013)	2.05
" The controlled dual release of curcumin and piperine from the G/SF microspheres would prolong their half-life, provide the optimal concentrations for therapeutic effects at a target site, and improve the bioavailability of curcumin."	( The development of injectable gelatin/silk fibroin microspheres for the dual delivery of curcumin and piperine. Damrongsakkul, S; Kanokpanont, S; Ratanavaraporn, J, 2014)	0.88
" Interestingly, piperine also plays a vital role in increasing the bioavailability of many drugs which again is a promising property."	( Piperine production by endophytic fungus Colletotrichum gloeosporioides isolated from Piper nigrum. Chithra, S; Jasim, B; Jyothis, M; Radhakrishnan, EK; Sachidanandan, P, 2014)	2.19
"In this study, curcumin was designed into the nanoformulation called cubosome with piperine in order to improve oral bioavailability and tissue distribution of curcumin."	( Preparation, characterisation and evaluation of curcumin with piperine-loaded cubosome nanoparticles. Fu, JW; Huang, DE; Shi, ZQ; Sun, DM; Tu, YS; Yao, N; Zhang, JJ, 2014)	0.87
" The pharmacokinetic test revealed that the cubosome could improve the oral bioavailability significantly compared to the suspension of curcumin with piperine and be mainly absorbed by the spleen."	( Preparation, characterisation and evaluation of curcumin with piperine-loaded cubosome nanoparticles. Fu, JW; Huang, DE; Shi, ZQ; Sun, DM; Tu, YS; Yao, N; Zhang, JJ, 2014)	0.84
" In vivo pharmacokinetics study and in situ single-pass intestinal perfusion were performed to investigate the effects of SEDDS on the bioavailability and intestinal absorption of piperine."	( Enhanced oral bioavailability of piperine by self-emulsifying drug delivery systems: in vitro, in vivo and in situ intestinal permeability studies. Cui, C; Ji, H; Li, X; Liu, H; Qin, M; Shao, B; Tang, J; Wang, Z; Wu, L, 2015)	0.89
"Although linarin possesses diverse pharmacological activities, its poor oral bioavailability has been a concern for further development."	( Effects of piperine on the intestinal permeability and pharmacokinetics of linarin in rats. Di, X; Feng, X; Liu, Y; Wang, X, 2014)	0.79
" This lack of cognitive effects may be due to low bioavailability and, in turn, reduced bioefficacy of resveratrol in vivo."	( Effects of resveratrol alone or in combination with piperine on cerebral blood flow parameters and cognitive performance in human subjects: a randomised, double-blind, placebo-controlled, cross-over investigation. Dew, TP; Haskell, CF; Kennedy, DO; Reay, JL; Wightman, EL; Williamson, G, 2014)	0.65
"The current review emphasizes on the herbal bioenhancers which themselves do not possess inherent pharmacological activity of their own but when co-administered with Active Pharmaceutical Ingredients (API), enhances their bioavailability and efficacy."	( Role of herbal bioactives as a potential bioavailability enhancer for Active Pharmaceutical Ingredients. Alexander, A; Kumari, L; Qureshi, A; Saraf, S; Sharma, M; Vaishnav, P, 2014)	0.4
" The present study aimed to investigate the efficacy of short-term supplementation with curcuminoids (co-administered with piperine to enhance the bioavailability of curcuminoids) in alleviating systemic oxidative stress and clinical symptoms, and improvement of health-related quality of life (HRQoL) in subjects suffering from chronic pulmonary complications due to SM exposure who are receiving standard respiratory treatments."	( Effects of Curcuminoids-Piperine Combination on Systemic Oxidative Stress, Clinical Symptoms and Quality of Life in Subjects with Chronic Pulmonary Complications Due to Sulfur Mustard: A Randomized Controlled Trial. Ghanei, M; Hajhashemi, A; Panahi, Y; Sahebkar, A, 2016)	0.95
"Knowing that curcumin has low bioavailability when administered orally, and that piperine has bioenhancer activity by inhibition of hepatic and intestinal biotransformation processes, the aim of this study was to investigate the antidiabetic and antioxidant activities of curcumin (90 mg/kg) and piperine (20 or 40 mg/kg), alone or co-administered, incorporated in yoghurt, in streptozotocin (STZ)-diabetic rats."	( Piperine, a natural bioenhancer, nullifies the antidiabetic and antioxidant activities of curcumin in streptozotocin-diabetic rats. Arcaro, CA; Assis, RP; Baviera, AM; Brunetti, IL; Costa, PI; Gutierres, VO; Moreira, TF, 2014)	2.07
" Piperine, one of the main constituents of black pepper, is known to increase the bioavailability of curcuminoids in mouse and human studies when consumed with turmeric."	( Turmeric and black pepper spices decrease lipid peroxidation in meat patties during cooking. Heber, D; Henning, SM; Huang, J; Lee, RP; Li, Z; Zerlin, A; Zhang, Y, 2015)	1.33
"An early prediction of solubility in physiological media (PBS, SGF and SIF) is useful to predict qualitatively bioavailability and absorption of lead candidates."	( Thermodynamic equilibrium solubility measurements in simulated fluids by 96-well plate method in early drug discovery. Bharate, SS; Vishwakarma, RA, 2015)	0.42
" The results show that Cur-PIP-SMEDDS can increase the solubility and stability of curcumin significantly, in the expectation of enhancing the bioavailability of it."	( [Optimization and characterization of curcumin-piperine dual drug loaded self-microemulsifying drug delivery system by simplex lattice design]. Dai, JD; Jiang, QL; Li, QP; Zhai, WW, 2014)	0.66
"P-glycoprotein (P-gp) efflux is the major cause of multidrug resistance (MDR) in tumors when using anticancer drugs, moreover, poor bioavailability of few drugs is also due to P-gp efflux in the gut."	( Co-delivery of rapamycin- and piperine-loaded polymeric nanoparticles for breast cancer treatment. Domb, AJ; Katiyar, SS; Khan, W; Muntimadugu, E; Rafeeqi, TA, 2016)	0.72
"Emodin (1,3,8-trihydroxy-6-methylanthraquinone) has been widely used as a traditional medicine and was shown to possess a multitude of health-promoting properties in pre-clinical studies, but its bioavailability was low due to the extensive glucuronidation in liver and intestine, hindering the development of emodin as a feasible chemopreventive agent."	( Effect of piperine on the bioavailability and pharmacokinetics of emodin in rats. Di, X; Liu, Y; Wang, X, 2015)	0.82
" The present study examined the synergistic effect of low doses of FA combined with subthreshold dose of piperine, a bioavailability enhancer, on depression-like behaviors in mice, and investigated the possible mechanism."	( Synergistic antidepressant-like effect of ferulic acid in combination with piperine: involvement of monoaminergic system. Chen, J; Chen, L; Chen, R; Huang, W; Li, G; Pan, J; Reed, M; Ruan, L; Wang, R; Xie, X; Xu, Y; Yan, Q; Zhang, M, 2015)	0.86
" Piperine, an alkaloid present in black pepper, seems to enhance the bioavailability and activity of curcumin."	( Curcumin in Combination with Piperine Suppresses Osteoclastogenesis In Vitro. Geurtsen, W; Leyhausen, G; Martins, CA; Volk, J, 2015)	1.62
" Phyllanthin along with piperine (a nutraceutical bioenhancer) was formulated as a mixed micellar lipid formulation (MMLF) in the present study and investigated to resolve the low bioavailability and enhance hepatoprotective effects on oral administration."	( Antioxidant and hepatoprotective effects of mixed micellar lipid formulation of phyllanthin and piperine in carbon tetrachloride-induced liver injury in rodents. Mishra, SH; Nagar, PA; Rajpara, A; Sethiya, NK; Shah, P, 2015)	0.94
" It has been proved that curcumin is poorly absorbed while piperine is a bioavailability-enhancer."	( Combination of curcumin and piperine prevents formation of gallstones in C57BL6 mice fed on lithogenic diet: whether NPC1L1/SREBP2 participates in this process? Li, M; Li, Y; Tian, Y; Wu, S, 2015)	0.95
" It also enhances the bioavailability of phytochemicals and drugs."	( Energetics, Thermodynamics, and Molecular Recognition of Piperine with DNA. Haridas, M; Haris, P; Mary, V; Sudarsanakumar, C, 2015)	0.66
" In present study, we assessed the effects of trans-resveratrol used in combination with piperine, commonly known as a bioavailability enhancer, on chronic unpredictable mild stress-induced depressive-like behaviors and relevant molecular targets."	( Piperine potentiates the effects of trans-resveratrol on stress-induced depressive-like behavior: involvement of monoaminergic system and cAMP-dependent pathway. An, Y; Lin, M; Pan, J; Wang, G; Wu, F; Xu, X; Xu, Y; Yu, Y; Zhang, C, 2016)	2.1
"We combine quantum chemical and molecular docking techniques to provide new insights into how piperine molecule in various forms of pepper enhances bioavailability of a number of drugs including curcumin in turmeric for which it increases its bioavailability by a 20-fold."	( Quantum Chemical and Docking Insights into Bioavailability Enhancement of Curcumin by Piperine in Pepper. Balasubramanian, K; Das, S; Patil, VM, 2016)	0.88
"These results demonstrated that increasing the bioavailability of piperine may be achieved as demonstrated by findings in this study."	( Hot melt extrusion as an approach to improve solubility, permeability and oral absorption of a psychoactive natural product, piperine. Alshehri, S; Alsheteli, A; Alsulays, B; Ashour, EA; Feng, X; Gryczke, A; Kolter, K; Langley, N; Majumdar, S; Repka, MA, 2016)	0.88
" Besides, the reported pharmacokinetics of PIP varied a lot without appropriate bioavailability determined from the same dose."	( Non-linear pharmacokinetics of piperine and its herb-drug interactions with docetaxel in Sprague-Dawley rats. Chow, MSS; Lam, CWK; Li, C; Ren, T; Wang, Q; Zhang, Y; Zuo, Z, 2016)	0.72
" Hence, in order to enhance the bioavailability of curcumin, we combined it with the bioavailability enhancers like piperine and quercetin."	( Influence of piperine and quercetin on antidiabetic potential of curcumin. Chintamaneni, M; Invally, M; Kaur, G, 2016)	1.01
" The present study involves formulation of curcumin and piperine coloaded glyceryl monooleate (GMO) nanoparticles coated with various surfactants with a view to enhance the bioavailability of curcumin and penetration of both drugs to the brain tissue crossing the BBB and to enhance the anti-parkinsonism effect of both drugs in a single platform."	( Delivery of Dual Drug Loaded Lipid Based Nanoparticles across the Blood-Brain Barrier Impart Enhanced Neuroprotection in a Rotenone Induced Mouse Model of Parkinson's Disease. Das, M; Kundu, P; Sahoo, SK; Tripathy, K, 2016)	0.68
"Curcumin (CUR) is known to exert numerous health-promoting effects in pharmacological studies, but its low bioavailability hinders the development of curcumin as a feasible therapeutic agent."	( Selective reduction in the expression of UGTs and SULTs, a novel mechanism by which piperine enhances the bioavailability of curcumin in rat. Cai, D; Chen, Y; Chen, Z; Gan, H; Huang, D; Huang, X; Sun, D; Yao, N; Zeng, Q; Zeng, X; Zhang, C; Zhao, Z; Zhong, G; Zhuo, J, 2017)	0.68
"The results suggest that altered pharmacokinetics and enhanced bioavailability of FEX might be attributed to PIP-mediated inhibition of P-gp drug efflux."	( The influence of piperine on the pharmacokinetics of fexofenadine, a P-glycoprotein substrate, in healthy volunteers. Bedada, SK; Boga, PK, 2017)	0.79
"Curcumin is a well-established cardioprotective phytoconstituent, but the poor bioavailability associated with it is always a matter of therapeutic challenge."	( Cardioprotective effect of curcumin and piperine combination against cyclophosphamide-induced cardiotoxicity. Bhattacharjee, A; Chakraborty, M; Kamath, JV, )	0.4
" The oral bioavailability of domperidone is very low due to its rapid first pass metabolism in the intestine and liver."	( Enhanced Oral Bioavailability of Domperidone with Piperine in Male Wistar Rats: Involvement of CYP3A1 and P-gp Inhibition. Athukuri, BL; Neerati, P, 2017)	0.71
" The oral pharmacokinetics of domperidone was evaluated by conducting oral bioavailability study in rats."	( Enhanced Oral Bioavailability of Domperidone with Piperine in Male Wistar Rats: Involvement of CYP3A1 and P-gp Inhibition. Athukuri, BL; Neerati, P, 2017)	0.71
"Piperine enhanced the oral bioavailability of domperidone by inhibiting CYP3A1 and P-gp in rats."	( Enhanced Oral Bioavailability of Domperidone with Piperine in Male Wistar Rats: Involvement of CYP3A1 and P-gp Inhibition. Athukuri, BL; Neerati, P, 2017)	2.15
"We previously reported that piperine, an active alkaloidal principal of black and long peppers, enhances drug bioavailability by inhibiting drug metabolism."	( Piperine Decreases Binding of Drugs to Human Plasma and Increases Uptake by Brain Microvascular Endothelial Cells. Dubey, RK; Imthurn, B; Leeners, B; Merki-Feld, GS; Rosselli, M, 2017)	2.19
" Consequently, there is a great interest in the application of piperine as an alternative medicine or bioavailability enhancer."	( Piperine-mediated drug interactions and formulation strategy for piperine: recent advances and future perspectives. Back, SY; Han, HK; Kim, HY; Lee, SH, 2018)	2.16
" Rifampicin, which is very effective against Mycobacterium tuberculosis, in both the phases of treatment, has certain concerns, which includes, decreased bioavailability with chronic use and hepatotoxicity."	( A Randomized, Controlled, Phase III Clinical Trial to Evaluate the Efficacy and Tolerability of Risorine with Conventional Rifampicin in the Treatment of Newly Diagnosed Pulmonary Tuberculosis Patients. Jagannath, K; Patel, A; Patel, M; Patel, N; Vora, A, 2017)	0.46
" However, the oral bioavailability of Rh2 is low, with P-glycoprotein (P-gp) and CYP3A4 being reported to be the main factors."	( Enhancement of oral bioavailability and immune response of Ginsenoside Rh2 by co-administration with piperine. Jiang, XH; Jin, ZH; Liu, H; Qiu, W; Wang, L, 2018)	0.7
" Raloxifene's oral bioavailability was determined in a series of pharmacokinetic experiments using the freely moving rat model."	( The Effect of Piperine Pro-Nano Lipospheres on Direct Intestinal Phase II Metabolism: The Raloxifene Paradigm of Enhanced Oral Bioavailability. Aldouby Bier, G; Cherniakov, I; Domb, AJ; Hoffman, A; Izgelov, D, 2018)	0.84
" Piperine is also known to increase the bioavailability of dietary components, including curcumin."	( Piperine potentiates curcumin-mediated repression of mTORC1 signaling in human intestinal epithelial cells: implications for the inhibition of protein synthesis and TNFα signaling. Hage, DS; He, B; Kaur, H; Moreau, R; Rodriguez, E; Zhang, C, 2018)	2.83
"Although silybin serves as a well-known hepatoprotective agent with prominent anti-inflammatory, anti-oxidant and anti-fibrotic activities, its low bioavailability limits its application in the treatment of chronic liver diseases."	( Piperine enhances the bioavailability of silybin via inhibition of efflux transporters BCRP and MRP2. Bi, X; Liu, Z; Qu, B; Xie, Y; Yuan, Z; Zhou, H, 2019)	1.96
"We hypothesized that inhibiting efflux transporter(s) and/or glucuronidation by piperine might enhance the bioavailability and efficacy of silybin."	( Piperine enhances the bioavailability of silybin via inhibition of efflux transporters BCRP and MRP2. Bi, X; Liu, Z; Qu, B; Xie, Y; Yuan, Z; Zhou, H, 2019)	2.18
" This review also highlights the importance of the nanoformulation of such bioactive phytochemicals that could enhance their bioavailability by providing an efficient targeted delivery system with a reduced systemic dose while resulting in a more efficient dosing at the target site."	( Combating breast cancer using combination therapy with 3 phytochemicals: Piperine, sulforaphane, and thymoquinone. Aumeeruddy, MZ; Mahomoodally, MF, 2019)	0.75
" Curcumin is a dietary phytochemical with hepatoprotective activities, though its low bioavailability is considered as a major challenge for clinical applications."	( Curcuminoids plus piperine improve nonalcoholic fatty liver disease: A clinical trial. Ahamdi, N; Ganjali, S; Majeed, M; Panahi, Y; Sahebkar, A; Valizadegan, G, 2019)	0.85
" Thus, the present study aimed to formulate piperine into a more solubilized form to enhance its oral bioavailability and facilitate its development as a potential anti-epileptic treatment."	( Piperine-loaded nanoparticles with enhanced dissolution and oral bioavailability for epilepsy control. Cheng, Y; Ho, NJ; Hu, M; Leung, SSY; Ren, T; Shek, TL; Xiao, M; Zhang, C; Zuo, Z, 2019)	2.22
" These results suggest that MST may be effective in enhancing the bioavailability of ginkgolide A in GBE."	( Mixing Ginkgo biloba Extract with Sesame Extract and Turmeric Oil Increases Bioavailability of Ginkgolide A in Mice Brain. Ayaki, I; Iwamoto, K; Kawamoto, H; Matsumura, S; Moriyama, T; Takeshita, F; Zaima, N, 2019)	0.51
"The combination with piperine had shown a significantly higher maximum concentration in plasma approximately 1500 μg/L within 1-2 h after oral dosing, and could increase oral bioavailability of oxyresveratrol approximately 2-fold."	( Comparative pharmacokinetics of oxyresveratrol alone and in combination with piperine as a bioenhancer in rats. Anukunwithaya, T; Junsaeng, D; Khemawoot, P; Likhitwitayawuid, K; Songvut, P; Sritularak, B, 2019)	1.06
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."	( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)	0.51
" Naturally available phyto chemicals like piperine and quercetin as well as some floroquinolones are known to inhibit MDR1 and CYP3A37 activity and increases bioavailability of co-administered drugs."	( Effect of piperine and quercetin alone or in combination with marbofloxacin on CYP3A37 and MDR1 mRNA expression levels in broiler chickens. Mathapati, BS; Modi, CM; Patel, HB; Patel, UD, 2019)	1.18
" However, the poor water solubility coupled with low bioavailability may inevitably hinder the application of Pip in the clinical setting."	( Piperine fast disintegrating tablets comprising sustained-release matrix pellets with enhanced bioavailability: formulation, Adu-Frimpong, M; Deng, W; Gu, Z; Xu, X; Yu, J; Zhou, G; Zhu, Y, 2020)	2
"It is feasible to deliver a cytotoxic concentration of piperine to TNBC cells via NPs with the potential for improved bioavailability and solubility in biological fluids."	( Delivery of Apoptosis-inducing Piperine to Triple-negative Breast Cancer Cells Hoskin, DW; Rad, JG, 2020)	1.09
" However, low bioavailability and severe nephrotoxicity are among the major shortcomings of AmB-based therapy."	( Efficient antileishmanial activity of amphotericin B and piperine entrapped in enteric coated guar gum nanoparticles. Goyal, N; Gupta, KC; Karthik, R; Pant, AB; Ray, L; Singh, SP; Srivastava, V, 2021)	0.87
"5-fold increase in oral bioavailability of CBD compared to control group without piperine."	( The effect of piperine on oral absorption of cannabidiol following acute vs. chronic administration. Domb, AJ; Hoffman, A; Izgelov, D, 2020)	1.15
" Unfortunately, this novel compound has poor aqueous solubility and bioavailability that limit its pharmaceutical effects."	( Preparation of curcumin-poly (allyl amine) hydrochloride based nanocapsules: Piperine in nanocapsules accelerates encapsulation and release of curcumin and effectiveness against colon cancer cells. Baydoun, E; Borjac, J; Moubarak, A; Patra, D; Slika, L, 2020)	0.79
" The results also conclude that addressing the bioavailability of resveratrol using it in combination with piperine does not prove more efficacious in preventing lupus-associated pathologies than resveratrol alone."	( Prophylactic effect of resveratrol and piperine on pristane-induced murine model of lupus-like disease. Bhatnagar, A; Pannu, N, 2020)	1.04
" The combination of paclitaxel (PTX) and piperine (PIP) may improve the bioavailability of paclitaxel for cancer therapy."	( EGFR Targeted Paclitaxel and Piperine Co-loaded Liposomes for the Treatment of Triple Negative Breast Cancer. Agrawal, N; Burande, AS; Jha, A; Mahto, SK; Mehata, AK; Muthu, MS; Poddar, S; Shaik, A; Viswanadh, MK, 2020)	1.12
" Our prior murine modeling research observed enhanced resveratrol bioavailability with piperine co-administration."	( A randomized, double-blind, dose-ranging, pilot trial of piperine with resveratrol on the effects on serum levels of resveratrol. Ahmad, N; Bailey, HH; Havinghurst, T; Johnson, JJ; Kim, K; Lozar, T; Scarlett, CO; Wollmer, BW, 2021)	1.09
" The present article provides a comprehensive review of PIP research in the last years concerning its chemical properties, synthesis, absorption, metabolism, bioavailability and toxicity."	( Piperine: Chemical, biological and nanotechnological applications. Araujo, VH; Chorilli, M; Quijia, CR, 2021)	2.06
" Curcumin and piperine (1-piperoylpiperidine) interact to each other and form a π-π intermolecular complex which enhance the bioavailability of curcumin by inhibition of glucuronidation of curcumin in liver."	( Therapeutic Approach against 2019-nCoV by Inhibition of ACE-2 Receptor. Kumar, D; Kumar, G; Singh, NP, 2021)	0.98
"The modulatory effects of piperine on drug metabolizing enzymes play an important role in the control of pharmacokinetic and the bioavailability properties of the administered drugs."	( The functional effects of piperine and piperine plus donepezil on hippocampal synaptic plasticity impairment in rat model of Alzheimer's disease. Ashrafpoor, M; Esfahani, DE; Nazifi, M; Oryan, S, 2021)	1.22
" This method has been used to quantitate these compounds in samples such as human intestinal epithelial cell lysates and mouse plasma or GI tissues in research aimed at examining the bioavailability of curcumin in the presence of piperine."	( Analysis of curcumin and piperine in biological samples by reversed-phase liquid chromatography with multi-wavelength detection. Bi, C; Hage, DS; Juritsch, AF; Kaur, H; Li, Z; Moreau, R; Rodriguez, EL; Woolfork, AG; Zhang, C, 2021)	1.11
" However, its low bioavailability and long term exposure related cardiovascular side effects, limit its clinical application."	( Piperine and Celecoxib synergistically inhibit colon cancer cell proliferation via modulating Wnt/β-catenin signaling pathway. Chaturvedi, S; Dewangan, J; Divakar, A; Kumar, S; Mishra, S; Rath, SK; Srivastava, S; Wahajuddin, M, 2021)	2.06
"The effect of PIP on the oral bioavailability of CXB in mice was investigated using HPLC analysis."	( Piperine and Celecoxib synergistically inhibit colon cancer cell proliferation via modulating Wnt/β-catenin signaling pathway. Chaturvedi, S; Dewangan, J; Divakar, A; Kumar, S; Mishra, S; Rath, SK; Srivastava, S; Wahajuddin, M, 2021)	2.06
"PIP as a bioenhancer increased the oral bioavailability of CXB (129%)."	( Piperine and Celecoxib synergistically inhibit colon cancer cell proliferation via modulating Wnt/β-catenin signaling pathway. Chaturvedi, S; Dewangan, J; Divakar, A; Kumar, S; Mishra, S; Rath, SK; Srivastava, S; Wahajuddin, M, 2021)	2.06
"The markedly low oral bioavailability of domperidone (anti-emetic drug) is associated with rapid first-pass metabolism in the intestine and liver."	( Piperine phytosomes for bioavailability enhancement of domperidone. Ghori, MU; Hussain, T; Irfan, M; Islam, N; Khan, IU; Mushtaq, M; Shahzad, Y; Yousaf, AM, 2022)	2.16
" In this work, the bioavailability and biological activities of piperine were presented and discussed."	( A review on the bioavailability, bio-efficacies and novel delivery systems for piperine. Cao, Y; Ho, CT; Huang, Q; Lu, M; Song, M; Xiao, J; Zhang, W; Zheng, Q, 2021)	1.09
" In the present review, the chemistry and bioavailability of PIP, its molecular targets in BC, and nanotechnological strategies are discussed."	( Piperine for treating breast cancer: A review of molecular mechanisms, combination with anticancer drugs, and nanosystems. Chorilli, M; Quijia, CR, 2022)	2.16
" The effect of spices on carotenoids' bioavailability is validated with active spice principles."	( Turmeric, red pepper, and black pepper affect carotenoids solubilized micelles properties and bioaccessibility: Capsaicin/piperine improves and curcumin inhibits carotenoids uptake and transport in Caco-2 cells. Ambedkar, R; Baskaran, V; Hanumanthappa, M; Lakshminarayana, R; Perumal, MK; Shilpa, S; Shwetha, HJ, 2021)	0.83
"The findings indicated that the combination of PIP and UA is an effective strategy in enhancing the bioavailability and hepatoprotective potential of UA."	( Synergistic effect of ursolic acid and piperine in CCl Biswas, S; Haldar, PK; Kar, A; Mukherjee, PK; Sharma, N, 2021)	0.89
" The novel combination of ATZ and PIP was proposed to enhance the bioavailability of both the compounds."	( Simultaneous Method Development and Validation of Anastrozole Along with Piperine: Degradation Studies and Degradants Characterization Using LC-QTOF-ESI-MS Along with In-silico ADMET Predictions. Alexander, A; Gajbhiye, R; Kumar, P; Mehta, P; Murty, US; Pawar, SD; Ravichandiran, V; Sarmah, B; Susanna, KJ, 2022)	0.95
" However, its extensive first-pass metabolism, short-life life, and low oral bioavailability confined its medical application."	( Calcium Ion-Sodium Alginate-Piperine-Based Microspheres: Evidence of Enhanced Encapsulation Efficiency, Bio-Adhesion, Controlled Delivery, and Oral Bioavailability of Isoniazid. Jain, SP; Pandharinath, RR; Pethe, AM; Pingale, PL; Telange, DR, 2022)	1.02
" In spite of its well-documented efficacies against numerous disease conditions, the limited systemic bioavailability of curcumin is a continuing concern."	( A Unifying Perspective in Blunting the Limited Oral Bioavailability of Curcumin: A Succinct Look. Alqahtani, A; Alqahtani, T; Balakumar, P; Lakshmiraj, RS; Rupeshkumar, M; Singh, G; Sundram, K; Thangathirupathi, A, 2022)	0.72
"In light of current challenges, the major concern pertaining to poor systemic bioavailability of curcumin, its improvement, especially in combination with piperine, and the necessity of additional research in this setting are together described in this review."	( A Unifying Perspective in Blunting the Limited Oral Bioavailability of Curcumin: A Succinct Look. Alqahtani, A; Alqahtani, T; Balakumar, P; Lakshmiraj, RS; Rupeshkumar, M; Singh, G; Sundram, K; Thangathirupathi, A, 2022)	0.92
"Intravenous route of drug administration has maximum bioavailability, which shows 100% of the drug reaches blood circulation, whereas the oral administration of drugs, are readily undergoing pre-systemic metabolism, which means the poor bioavailability of the drug and limited amount of drug reaches the target site."	( A Recent Review on Bio-availability Enhancement of Poorly Water-soluble Drugs by using Bioenhancer and Nanoparticulate Drug Delivery System. Kumar, A; Kumar, D; Kumar, M; Kumar, S; Mandal, UK, 2022)	0.72
"Bioenhancers are substances having medicinal entities which enhance the bioavailability and efficacy of the active constituents of drugs."	( A Recent Review on Bio-availability Enhancement of Poorly Water-soluble Drugs by using Bioenhancer and Nanoparticulate Drug Delivery System. Kumar, A; Kumar, D; Kumar, M; Kumar, S; Mandal, UK, 2022)	0.72
"Bioenhancers are crucial to amplifying the bioavailability of many synthetic drugs."	( A Recent Review on Bio-availability Enhancement of Poorly Water-soluble Drugs by using Bioenhancer and Nanoparticulate Drug Delivery System. Kumar, A; Kumar, D; Kumar, M; Kumar, S; Mandal, UK, 2022)	0.72
" Herein, the amorphous solid dispersions (SD) of lumefantrine (LUMF) containing piperine (PIP), a P-gp and CYP3A4 inhibitor, were formulated with Soluplus (Sol), Klucel (Klu) and Lutrol F68 (Lut), polymeric carriers, to improve solubility and bioavailability of LUMF following oral administration."	( Lumefantrine solid dispersions with piperine for the enhancement of solubility, bioavailability and anti-parasite activity. Aji, A; Deshmukh, PR; Ghule, BV; Inamdar, NN; Jane, K; Khade, RR; Kotagale, NR; Pendharkar, VV; Takale, NR, 2022)	1.22
" Piperine has been indicated as a bioavailability enhancer of turmeric and consequently of its biological effects."	( Turmeric supplementation with piperine is more effective than turmeric alone in attenuating oxidative stress and inflammation in hemodialysis patients: A randomized, double-blind clinical trial. Braga, CC; Carlos da Cunha, L; Costa, NA; de Souza Freitas, ATV; Freitas E Silva-Santana, NC; Peixoto, MDRG; Pereira Martins, TF; Rodrigues, HCN; Silva, MAC, 2022)	1.92
" However, poor oral bioavailability and permeability of curcumin are a major challenge for formulation scientists."	( Formulation and Development of Curcumin-Piperine-Loaded S-SNEDDS for the Treatment of Alzheimer's Disease. Ahmad, S; Hafeez, A, 2023)	1.18
" Co-administration of curcumin along with piperine could potentially improve the bioavailability of curcumin."	( Curcumin-piperine co-supplementation and human health: A comprehensive review of preclinical and clinical studies. Bagherniya, M; Heidari, H; Jamialahmadi, T; Majeed, M; Sahebkar, A; Sathyapalan, T, 2023)	1.59
" This review also emphasizes the significance of the co-delivery vehicles-based nanoparticles of such bioactive phytochemicals that could improve their bioavailability and reduce their systemic dose."	( Co-administration of curcumin with other phytochemicals improves anticancer activity by regulating multiple molecular targets. Asoodeh, A; Ghobadi, N, 2023)	0.91
" Piperine has the ability to improve the bioavailability of many compounds when co-administered."	( Amorphous System of Hesperetin and Piperine-Improvement of Apparent Solubility, Permeability, and Biological Activities. Cielecka-Piontek, J; Miklaszewski, A; Pietrzak, R; Wdowiak, K, 2023)	2.1
" The poor bioavailability of curcumin can be improved with the concomitant administration of piperine, with no severe adverse effects on glycemia reported so far in the literature."	( Overview of Curcumin and Piperine Effects on Glucose Metabolism: The Case of an Insulinoma Patient's Loss of Consciousness. Ciniglio Appiani, G; De Gennaro Colonna, V; Garzia, E; La Vecchia, C; Marfia, G; Moroncini, G; Panzeri, E; Servida, S; Tomaino, L; Vigna, L, 2023)	1.43
"Poor bioavailability hampers the use of curcumin and piperine as biologically active agents."	( Hot-Melt Extrusion as an Effective Technique for Obtaining an Amorphous System of Curcumin and Piperine with Improved Properties Essential for Their Better Biological Activities. Cielecka-Piontek, J; Pietrzak, R; Tykarska, E; Wdowiak, K, 2023)	1.38
" It possesses lower bioavailability due to poor solubility, lesser permeability and first pass metabolism effect."	( Aeri, V; Kohli, K; Kumari, A; Ralli, T; Saifi, Z, 2023)	0.91
" In summary, the nanopiperine showed potent neuroprotective and antidepressant activity, and stability relating to the elevated level of hippocampal BDNF level and as compared to pure piperine, the nanopiperine showed better oral bioavailability and stability."	( Nanoemulsion-based piperine to enhance bioavailability for the treatment of LPS-induced depression-like behaviour in mice. Basavaraju, SM; Kinattingal, N; Krishna, KL; Mehdi, S; Mudhol, S; Peddha, MS; Ud Din Wani, S, 2023)	1.56
"As a plant-derived drug, piperine possesses therapeutic efficacy for many diseases, but its inherent low solubility and bioavailability have greatly limited its clinical use."	( Enhanced anticancer activity of piperine: Structural optimization and chitosan-based microgels with boosted drug delivery. Li, H; Wang, J; Wang, X, 2023)	1.5
" In order to increase the bioavailability and therapeutic effectiveness of piperine and its analogs, researchers have been looking at various extraction methods and synthesis approaches."	( Significant Advancement in Various Synthetic Strategies and Pharmacotherapy of Piperine Derivatives: A Review. Ahsan, MJ; Arya, A; Joshi, S; Khurana, N; Kumar, R; Mazumder, A; Rana, K; Shabana, K; Tyagi, S; Yar, MS, 2023)	1.37

Excerpt	Relevance	Reference
" The dose-response relationship and possible tachyphylaxis were tested for each chemical."	( Activation of neurons in rat trigeminal subnucleus caudalis by different irritant chemicals applied to oral or ocular mucosa. Carstens, E; Handwerker, HO; Kuenzler, N, 1998)	0.3
" Further in-depth studies in a large number of patients receiving different dosage regimens are required to confirm these results and further our understanding of a possible clinical advantage arising from the bioenhancement capabilities of piperine in the treatment of HIV infection."	( Influence of piperine on the pharmacokinetics of nevirapine under fasting conditions: a randomised, crossover, placebo-controlled study. Kasibhatta, R; Naidu, MU, 2007)	0.89
" The results showed that piperine at all dosage range used in this study possessed anti-depression like activity and cognitive enhancing effect at all treatment duration."	( Piperine, the potential functional food for mood and cognitive disorders. Chonpathompikunlert, P; Muchimapura, S; Priprem, A; Tankamnerdthai, O; Wattanathorn, J, 2008)	2.09
"Simple and rapid stability-indicating HPLC methods were developed for the individual analysis of aconitine (ACN) and piperine (PIN) in Mahamrutynjaya rasa, an herbal dosage form containing Aconitum ferox, Piper nigrum, and Piper longum in combination."	( Stability-indicating reversed-phase liquid chromatographic methods for the determination of aconitine and piperine in a polyherbal formulation. Pathak, A; Rai, P; Rajput, SJ, )	0.55
" The results showed that piperine at all dosage range used in this study significantly improved memory impairment and neurodegeneration in hippocampus."	( Piperine, the main alkaloid of Thai black pepper, protects against neurodegeneration and cognitive impairment in animal model of cognitive deficit like condition of Alzheimer's disease. Chonpathompikunlert, P; Muchimapura, S; Wattanathorn, J, 2010)	2.11
", dose, dosing regimen, genetic variation and species)."	( The effects of black pepper on the intestinal absorption and hepatic metabolism of drugs. Han, HK, 2011)	0.37
" Sigmoidal dose-response curves were plotted and IC(50) values were estimated."	( In vitro and in situ evaluation of herb-drug interactions during intestinal metabolism and absorption of baicalein. Fong, YK; Li, CR; Lin, G; Wang, S; Wo, SK; Zhang, L; Zhou, L; Zuo, Z, 2012)	0.38
" The present study illustrated the potential of nanoemulsion dosage form in improving biopharmaceutic performance of piperine and guggul sterone."	( Development and validation of HPLC method for simultaneous estimation of piperine and guggulsterones in compound Unani formulation (tablets) and a nanoreservoir system. Ahmad, S; Ali, I; Arif Zaidi, SM; Baboota, S; Kamal, YT; Mohammed Musthaba, S; Parveen, R; Siddiqui, KM; Singh, M, 2012)	0.82
"The present study was aimed to characterize the anticonvulsant effects of piperine in combination with well established antiepileptic drug (AED) phenytoin, in the mouse maximal electroshock (MES)-induced seizure model by using the type I isobolographic analysis for non-parallel dose-response relationship curves (DRRCs)."	( Combination therapy of piperine and phenytoin in maximal electroshock induced seizures in mice: isobolographic and biochemical analysis. Khanam, R; Pillai, KK; Saraogi, P; Vohora, D, 2013)	0.93
" In an attempt to find the mechanism by which piperine enhances the bioavailability of curcumin, the dosage ratio (CUR: PIP) and pre-treatment with piperine were hypothesized as key factors for improving the bioavailability in this combination."	( Selective reduction in the expression of UGTs and SULTs, a novel mechanism by which piperine enhances the bioavailability of curcumin in rat. Cai, D; Chen, Y; Chen, Z; Gan, H; Huang, D; Huang, X; Sun, D; Yao, N; Zeng, Q; Zeng, X; Zhang, C; Zhao, Z; Zhong, G; Zhuo, J, 2017)	0.94
" Given that piperine inhibits or stimulates the activity of metabolic enzymes and transporters depending on the treatment conditions, the clinical significance of piperine-drug interactions should be assessed by varying the dose, dosing frequency, and the duration of treatment."	( Piperine-mediated drug interactions and formulation strategy for piperine: recent advances and future perspectives. Back, SY; Han, HK; Kim, HY; Lee, SH, 2018)	2.3
"The low permeability of anti-malarial drugs must be borne in mind during development of effective dosage regimens of new drugs."	( Absorptive and Secretory Transport of Selected Artemisinin Derivatives Across Caco-2 Cell Monolayers. Gouws, C; Hamman, J; Haynes, RK; Heyns, J; Willers, C; Wong, HN, 2018)	0.48
" This review also highlights the importance of the nanoformulation of such bioactive phytochemicals that could enhance their bioavailability by providing an efficient targeted delivery system with a reduced systemic dose while resulting in a more efficient dosing at the target site."	( Combating breast cancer using combination therapy with 3 phytochemicals: Piperine, sulforaphane, and thymoquinone. Aumeeruddy, MZ; Mahomoodally, MF, 2019)	0.75
"5 ml of pristane and after 2 months they were orally dosed with resveratrol combinations for 4 months."	( Combinatorial therapeutic effect of resveratrol and piperine on murine model of systemic lupus erythematosus. Bhatnagar, A; Pannu, N, 2020)	0.81
" Combination dosage forms of various API incorporating piperine as a bio-enhancer can be a potential area of thrust for upcoming drug design and development."	( Propitious Profile of Peppery Piperine. Aggarwal, G; Bakshi, H; Dhingra, GA; Nagpal, M; Singh, M, 2021)	1.16

Product Category	Products
Other	1
Vitamins & Supplements	2
Herbs, Botanicals & Homeopathy	3
Pet Supplies	1

Product	Brand	Category	Compounds Matched from Ingredients	Date Retrieved
Cymbiotika Allergy Defense Alpha-Glycosyl Isoquercitrin -- 60 Capsules	Cymbiotika	Vitamins & Supplements	Isoquercitrin, Bioperine, Quercetin	2024-11-29 10:47:42
Emerald Labs UC-II® Joint Formula -- 60 Vegetable Capsules	Emerald Labs	Vitamins & Supplements	Bioperine	2024-11-29 10:47:42
Futurebiotics Cholesterol Balance® -- 90 Vegetarian Capsules	Futurebiotics	Herbs, Botanicals & Homeopathy	Campesterol, BioPerine	2024-11-29 10:47:42
Futurebiotics GlucoActive® -- 60 Vegetarian Capsules	Futurebiotics	Herbs, Botanicals & Homeopathy	Chromium, BioPerine, Vanadium	2024-11-29 10:47:42
Kuli Kuli Moringa Turmeric Super Gummies Lemon -- 60 Gummies	Kuli Kuli	Herbs, Botanicals & Homeopathy	citric acid, citric acid, Piperine	2024-11-29 10:47:42
Zesty Paws Senior Advanced Mobility Glucosamine Hip & Joint Supplement for Dogs Chicken -- 90 Soft Chews	Zesty Paws	Pet Supplies	citric acid, Vitamin C, citric acid, Vitamin E, methylsulfonylmethane, vitamin E, Glucosamine, powdered cellulose, Bio Perine	2024-11-29 10:47:42

Role	Description
NF-kappaB inhibitor	An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
food component	A physiological role played by any substance that is distributed in foodstuffs. It includes materials derived from plants or animals, such as vitamins or minerals, as well as environmental contaminants.
human blood serum metabolite	Any metabolite (endogenous or exogenous) found in human blood serum samples.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
benzodioxoles
N-acylpiperidine
piperidine alkaloid
tertiary carboxamide	A carboxamide resulting from the formal condensation of a carboxylic acid with a secondary amine; formula RC(=O)NHR(1)R(2).
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
piperine biosynthesis	0	5

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, Beta-lactamase	Escherichia coli K-12	Potency	44.6684	0.0447	17.8581	100.0000	AID485294
Chain A, HADH2 protein	Homo sapiens (human)	Potency	39.8107	0.0251	20.2376	39.8107	AID893
Chain B, HADH2 protein	Homo sapiens (human)	Potency	39.8107	0.0251	20.2376	39.8107	AID893
Chain A, 2-oxoglutarate Oxygenase	Homo sapiens (human)	Potency	31.6228	0.1778	14.3909	39.8107	AID2147
Luciferase	Photinus pyralis (common eastern firefly)	Potency	6.6185	0.0072	15.7588	89.3584	AID1224835; AID588342
acid sphingomyelinase	Homo sapiens (human)	Potency	31.6228	14.1254	24.0613	39.8107	AID504937
BRCA1	Homo sapiens (human)	Potency	8.9125	0.8913	7.7225	25.1189	AID624202
pregnane X receptor	Rattus norvegicus (Norway rat)	Potency	7.0795	0.0251	27.9203	501.1870	AID651751
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	5.0150	0.0060	38.0041	19,952.5996	AID1159521; AID1159523
ATAD5 protein, partial	Homo sapiens (human)	Potency	10.9479	0.0041	10.8903	31.5287	AID504466; AID504467
TDP1 protein	Homo sapiens (human)	Potency	29.0929	0.0008	11.3822	44.6684	AID686978; AID686979
GLI family zinc finger 3	Homo sapiens (human)	Potency	2.2886	0.0007	14.5928	83.7951	AID1259368; AID1259369; AID1259392
AR protein	Homo sapiens (human)	Potency	12.5825	0.0002	21.2231	8,912.5098	AID1259243; AID1259247; AID1259381; AID743035; AID743040; AID743042; AID743054
thioredoxin glutathione reductase	Schistosoma mansoni	Potency	39.8107	0.1000	22.9075	100.0000	AID485364
aldehyde dehydrogenase 1 family, member A1	Homo sapiens (human)	Potency	39.8107	0.0112	12.4002	100.0000	AID1030
estrogen receptor 2 (ER beta)	Homo sapiens (human)	Potency	61.2549	0.0006	57.9133	22,387.1992	AID1259378
nuclear receptor subfamily 1, group I, member 3	Homo sapiens (human)	Potency	4.7270	0.0010	22.6508	76.6163	AID1224838; AID1224839; AID1224893
progesterone receptor	Homo sapiens (human)	Potency	57.8620	0.0004	17.9460	75.1148	AID1346795
cytochrome P450 family 3 subfamily A polypeptide 4	Homo sapiens (human)	Potency	11.9877	0.0123	7.9835	43.2770	AID1645841
glucocorticoid receptor [Homo sapiens]	Homo sapiens (human)	Potency	44.6684	0.0002	14.3764	60.0339	AID588532
retinoic acid nuclear receptor alpha variant 1	Homo sapiens (human)	Potency	3.0975	0.0030	41.6115	22,387.1992	AID1159552; AID1159553; AID1159555
retinoid X nuclear receptor alpha	Homo sapiens (human)	Potency	31.8010	0.0008	17.5051	59.3239	AID1159527; AID1159531; AID588544
estrogen-related nuclear receptor alpha	Homo sapiens (human)	Potency	10.0437	0.0015	30.6073	15,848.9004	AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403
farnesoid X nuclear receptor	Homo sapiens (human)	Potency	49.8081	0.3758	27.4851	61.6524	AID588526; AID743217
pregnane X nuclear receptor	Homo sapiens (human)	Potency	16.6491	0.0054	28.0263	1,258.9301	AID1346982; AID720659
estrogen nuclear receptor alpha	Homo sapiens (human)	Potency	6.6918	0.0002	29.3054	16,493.5996	AID1259244; AID1259248; AID1259383; AID743069; AID743079; AID743080; AID743091
G	Vesicular stomatitis virus	Potency	10.6840	0.0123	8.9648	39.8107	AID1645842
cytochrome P450 2D6	Homo sapiens (human)	Potency	37.9083	0.0010	8.3798	61.1304	AID1645840
peroxisome proliferator-activated receptor delta	Homo sapiens (human)	Potency	6.9327	0.0010	24.5048	61.6448	AID743215
peroxisome proliferator activated receptor gamma	Homo sapiens (human)	Potency	48.8311	0.0010	19.4141	70.9645	AID588536; AID588537; AID743191
aryl hydrocarbon receptor	Homo sapiens (human)	Potency	4.1740	0.0007	23.0674	1,258.9301	AID651777; AID743085; AID743122
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a	Homo sapiens (human)	Potency	1.3521	0.0017	23.8393	78.1014	AID743083
thyroid stimulating hormone receptor	Homo sapiens (human)	Potency	77.1154	0.0016	28.0151	77.1139	AID1259385
Histone H2A.x	Cricetulus griseus (Chinese hamster)	Potency	101.4926	0.0391	47.5451	146.8240	AID1224845
NPC intracellular cholesterol transporter 1 precursor	Homo sapiens (human)	Potency	2.5119	0.0126	2.4518	25.0177	AID485313
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1	Homo sapiens (human)	Potency	15.8489	0.0018	15.6638	39.8107	AID894
nuclear factor erythroid 2-related factor 2 isoform 2	Homo sapiens (human)	Potency	20.5962	0.0041	9.9848	25.9290	AID504444
thyroid hormone receptor beta isoform 2	Rattus norvegicus (Norway rat)	Potency	62.2781	0.0003	23.4451	159.6830	AID743065; AID743067
histone deacetylase 9 isoform 3	Homo sapiens (human)	Potency	9.3852	0.0376	17.0823	61.1927	AID1259364; AID1259388
mitogen-activated protein kinase 1	Homo sapiens (human)	Potency	39.8107	0.0398	16.7842	39.8107	AID995
ras-related protein Rab-9A	Homo sapiens (human)	Potency	2.5119	0.0002	2.6215	31.4954	AID485297
nuclear factor erythroid 2-related factor 2 isoform 1	Homo sapiens (human)	Potency	28.2019	0.0006	27.2152	1,122.0200	AID720636; AID743202; AID743219
DNA polymerase iota isoform a (long)	Homo sapiens (human)	Potency	89.1251	0.0501	27.0736	89.1251	AID588590
urokinase-type plasminogen activator precursor	Mus musculus (house mouse)	Potency	10.0000	0.1585	5.2879	12.5893	AID540303
plasminogen precursor	Mus musculus (house mouse)	Potency	10.0000	0.1585	5.2879	12.5893	AID540303
urokinase plasminogen activator surface receptor precursor	Mus musculus (house mouse)	Potency	10.0000	0.1585	5.2879	12.5893	AID540303
nuclear receptor ROR-gamma isoform 1	Mus musculus (house mouse)	Potency	5.6234	0.0079	8.2332	1,122.0200	AID2546
survival motor neuron protein isoform d	Homo sapiens (human)	Potency	14.1254	0.1259	12.2344	35.4813	AID1458
cytochrome P450 3A4 isoform 1	Homo sapiens (human)	Potency	12.5893	0.0316	10.2792	39.8107	AID884; AID885
Gamma-aminobutyric acid receptor subunit pi	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Voltage-dependent calcium channel gamma-2 subunit	Mus musculus (house mouse)	Potency	1.3477	0.0015	57.7890	15,848.9004	AID1259244
Interferon beta	Homo sapiens (human)	Potency	10.6840	0.0033	9.1582	39.8107	AID1645842
HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)	Potency	10.6840	0.0123	8.9648	39.8107	AID1645842
Cellular tumor antigen p53	Homo sapiens (human)	Potency	68.7291	0.0023	19.5956	74.0614	AID651631
Gamma-aminobutyric acid receptor subunit beta-1	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit delta	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit gamma-2	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Glutamate receptor 2	Rattus norvegicus (Norway rat)	Potency	1.3477	0.0015	51.7393	15,848.9004	AID1259244
Gamma-aminobutyric acid receptor subunit alpha-5	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-3	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit gamma-1	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-2	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-4	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit gamma-3	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-6	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-1	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit beta-3	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit beta-2	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
GABA theta subunit	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Inositol hexakisphosphate kinase 1	Homo sapiens (human)	Potency	10.6840	0.0123	8.9648	39.8107	AID1645842
ATPase family AAA domain-containing protein 5	Homo sapiens (human)	Potency	11.8237	0.0119	17.9420	71.5630	AID651632; AID720516
Ataxin-2	Homo sapiens (human)	Potency	12.2891	0.0119	12.2221	68.7989	AID651632
Gamma-aminobutyric acid receptor subunit epsilon	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
cytochrome P450 2C9, partial	Homo sapiens (human)	Potency	10.6840	0.0123	8.9648	39.8107	AID1645842
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Carbonic anhydrase 1	Homo sapiens (human)	IC50 (µMol)	31,000.0000	0.0058	2.1410	7.9000	AID1803035
Carbonic anhydrase 2	Homo sapiens (human)	IC50 (µMol)	31,000.0000	0.0002	1.1060	8.3000	AID1803035
ATP-dependent translocase ABCB1	Homo sapiens (human)	IC50 (µMol)	44.8000	0.0002	2.3185	10.0000	AID679605; AID680071
Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)	IC50 (µMol)	54.0000	0.0001	1.6847	9.3200	AID1603728
Amine oxidase [flavin-containing] A	Homo sapiens (human)	IC50 (µMol)	58.9800	0.0000	2.3789	9.7700	AID718839
Amine oxidase [flavin-containing] B	Homo sapiens (human)	IC50 (µMol)	0.7665	0.0000	1.8914	9.5700	AID1519691; AID718838
Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)	IC50 (µMol)	0.8800	0.0005	0.7427	10.0000	AID1872620
Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)	Ki	0.7100	0.0120	0.5037	2.7000	AID1872619
Amine oxidase [flavin-containing] B	Mus musculus (house mouse)	Ki	3.1900	0.1000	2.3790	6.0000	AID453498
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)	EC50 (µMol)	29.1000	0.0011	2.0009	10.0000	AID1155357; AID1891770
Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)	EC50 (µMol)	29.1000	0.0014	1.9578	10.0000	AID1155357; AID1891770
Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)	EC50 (µMol)	29.1000	0.0014	1.7768	10.0000	AID1155357; AID1891770
Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)	EC50 (µMol)	3.1623	0.0005	1.0674	6.3096	AID478379
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)	Activity	10.0000	0.0100	3.5198	10.0000	AID500214
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
one-carbon metabolic process	Carbonic anhydrase 1	Homo sapiens (human)
morphogenesis of an epithelium	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of synaptic transmission, GABAergic	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of cellular pH reduction	Carbonic anhydrase 2	Homo sapiens (human)
angiotensin-activated signaling pathway	Carbonic anhydrase 2	Homo sapiens (human)
regulation of monoatomic anion transport	Carbonic anhydrase 2	Homo sapiens (human)
secretion	Carbonic anhydrase 2	Homo sapiens (human)
regulation of intracellular pH	Carbonic anhydrase 2	Homo sapiens (human)
neuron cellular homeostasis	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of dipeptide transmembrane transport	Carbonic anhydrase 2	Homo sapiens (human)
regulation of chloride transport	Carbonic anhydrase 2	Homo sapiens (human)
carbon dioxide transport	Carbonic anhydrase 2	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 2	Homo sapiens (human)
cell surface receptor signaling pathway via JAK-STAT	Interferon beta	Homo sapiens (human)
response to exogenous dsRNA	Interferon beta	Homo sapiens (human)
B cell activation involved in immune response	Interferon beta	Homo sapiens (human)
cell surface receptor signaling pathway	Interferon beta	Homo sapiens (human)
cell surface receptor signaling pathway via JAK-STAT	Interferon beta	Homo sapiens (human)
response to virus	Interferon beta	Homo sapiens (human)
positive regulation of autophagy	Interferon beta	Homo sapiens (human)
cytokine-mediated signaling pathway	Interferon beta	Homo sapiens (human)
natural killer cell activation	Interferon beta	Homo sapiens (human)
positive regulation of peptidyl-serine phosphorylation of STAT protein	Interferon beta	Homo sapiens (human)
cellular response to interferon-beta	Interferon beta	Homo sapiens (human)
B cell proliferation	Interferon beta	Homo sapiens (human)
negative regulation of viral genome replication	Interferon beta	Homo sapiens (human)
innate immune response	Interferon beta	Homo sapiens (human)
positive regulation of innate immune response	Interferon beta	Homo sapiens (human)
regulation of MHC class I biosynthetic process	Interferon beta	Homo sapiens (human)
negative regulation of T cell differentiation	Interferon beta	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Interferon beta	Homo sapiens (human)
defense response to virus	Interferon beta	Homo sapiens (human)
type I interferon-mediated signaling pathway	Interferon beta	Homo sapiens (human)
neuron cellular homeostasis	Interferon beta	Homo sapiens (human)
cellular response to exogenous dsRNA	Interferon beta	Homo sapiens (human)
cellular response to virus	Interferon beta	Homo sapiens (human)
negative regulation of Lewy body formation	Interferon beta	Homo sapiens (human)
negative regulation of T-helper 2 cell cytokine production	Interferon beta	Homo sapiens (human)
positive regulation of apoptotic signaling pathway	Interferon beta	Homo sapiens (human)
response to exogenous dsRNA	Interferon beta	Homo sapiens (human)
B cell differentiation	Interferon beta	Homo sapiens (human)
natural killer cell activation involved in immune response	Interferon beta	Homo sapiens (human)
adaptive immune response	Interferon beta	Homo sapiens (human)
T cell activation involved in immune response	Interferon beta	Homo sapiens (human)
humoral immune response	Interferon beta	Homo sapiens (human)
positive regulation of T cell mediated cytotoxicity	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
adaptive immune response	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
antigen processing and presentation of endogenous peptide antigen via MHC class I via ER pathway, TAP-independent	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
regulation of T cell anergy	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
defense response	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
immune response	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
detection of bacterium	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
regulation of interleukin-12 production	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
regulation of interleukin-6 production	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
protection from natural killer cell mediated cytotoxicity	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
innate immune response	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
regulation of dendritic cell differentiation	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
antigen processing and presentation of endogenous peptide antigen via MHC class Ib	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
negative regulation of cell population proliferation	Cellular tumor antigen p53	Homo sapiens (human)
regulation of cell cycle	Cellular tumor antigen p53	Homo sapiens (human)
regulation of cell cycle G2/M phase transition	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response	Cellular tumor antigen p53	Homo sapiens (human)
ER overload response	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to glucose starvation	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
regulation of apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of miRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
mitophagy	Cellular tumor antigen p53	Homo sapiens (human)
in utero embryonic development	Cellular tumor antigen p53	Homo sapiens (human)
somitogenesis	Cellular tumor antigen p53	Homo sapiens (human)
release of cytochrome c from mitochondria	Cellular tumor antigen p53	Homo sapiens (human)
hematopoietic progenitor cell differentiation	Cellular tumor antigen p53	Homo sapiens (human)
T cell proliferation involved in immune response	Cellular tumor antigen p53	Homo sapiens (human)
B cell lineage commitment	Cellular tumor antigen p53	Homo sapiens (human)
T cell lineage commitment	Cellular tumor antigen p53	Homo sapiens (human)
response to ischemia	Cellular tumor antigen p53	Homo sapiens (human)
nucleotide-excision repair	Cellular tumor antigen p53	Homo sapiens (human)
double-strand break repair	Cellular tumor antigen p53	Homo sapiens (human)
regulation of DNA-templated transcription	Cellular tumor antigen p53	Homo sapiens (human)
regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
protein import into nucleus	Cellular tumor antigen p53	Homo sapiens (human)
autophagy	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator resulting in cell cycle arrest	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator resulting in transcription of p21 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
transforming growth factor beta receptor signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
Ras protein signal transduction	Cellular tumor antigen p53	Homo sapiens (human)
gastrulation	Cellular tumor antigen p53	Homo sapiens (human)
neuroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of neuroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
protein localization	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of DNA replication	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of cell population proliferation	Cellular tumor antigen p53	Homo sapiens (human)
determination of adult lifespan	Cellular tumor antigen p53	Homo sapiens (human)
mRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
rRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
response to salt stress	Cellular tumor antigen p53	Homo sapiens (human)
response to inorganic substance	Cellular tumor antigen p53	Homo sapiens (human)
response to X-ray	Cellular tumor antigen p53	Homo sapiens (human)
response to gamma radiation	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of gene expression	Cellular tumor antigen p53	Homo sapiens (human)
cardiac muscle cell apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of cardiac muscle cell apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
glial cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
viral process	Cellular tumor antigen p53	Homo sapiens (human)
glucose catabolic process to lactate via pyruvate	Cellular tumor antigen p53	Homo sapiens (human)
cerebellum development	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of cell growth	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
mitotic G1 DNA damage checkpoint signaling	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of telomere maintenance via telomerase	Cellular tumor antigen p53	Homo sapiens (human)
T cell differentiation in thymus	Cellular tumor antigen p53	Homo sapiens (human)
tumor necrosis factor-mediated signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
regulation of tissue remodeling	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to UV	Cellular tumor antigen p53	Homo sapiens (human)
multicellular organism growth	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of mitochondrial membrane permeability	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to glucose starvation	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
entrainment of circadian clock by photoperiod	Cellular tumor antigen p53	Homo sapiens (human)
mitochondrial DNA repair	Cellular tumor antigen p53	Homo sapiens (human)
regulation of DNA damage response, signal transduction by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of neuron apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
transcription initiation-coupled chromatin remodeling	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of proteolysis	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of DNA-templated transcription	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of DNA-templated transcription	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of RNA polymerase II transcription preinitiation complex assembly	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
response to antibiotic	Cellular tumor antigen p53	Homo sapiens (human)
fibroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of fibroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
circadian behavior	Cellular tumor antigen p53	Homo sapiens (human)
bone marrow development	Cellular tumor antigen p53	Homo sapiens (human)
embryonic organ development	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylation	Cellular tumor antigen p53	Homo sapiens (human)
protein stabilization	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of helicase activity	Cellular tumor antigen p53	Homo sapiens (human)
protein tetramerization	Cellular tumor antigen p53	Homo sapiens (human)
chromosome organization	Cellular tumor antigen p53	Homo sapiens (human)
neuron apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
regulation of cell cycle	Cellular tumor antigen p53	Homo sapiens (human)
hematopoietic stem cell differentiation	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of glial cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
type II interferon-mediated signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
cardiac septum morphogenesis	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of programmed necrotic cell death	Cellular tumor antigen p53	Homo sapiens (human)
protein-containing complex assembly	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to endoplasmic reticulum stress	Cellular tumor antigen p53	Homo sapiens (human)
thymocyte apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of thymocyte apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
necroptotic process	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to hypoxia	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to xenobiotic stimulus	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to ionizing radiation	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to gamma radiation	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to UV-C	Cellular tumor antigen p53	Homo sapiens (human)
stem cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
signal transduction by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
reactive oxygen species metabolic process	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to actinomycin D	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of release of cytochrome c from mitochondria	Cellular tumor antigen p53	Homo sapiens (human)
cellular senescence	Cellular tumor antigen p53	Homo sapiens (human)
replicative senescence	Cellular tumor antigen p53	Homo sapiens (human)
oxidative stress-induced premature senescence	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
oligodendrocyte apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of execution phase of apoptosis	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of mitophagy	Cellular tumor antigen p53	Homo sapiens (human)
regulation of mitochondrial membrane permeability involved in apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
regulation of intrinsic apoptotic signaling pathway by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of miRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of G1 to G0 transition	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of miRNA processing	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of glucose catabolic process to lactate via pyruvate	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of pentose-phosphate shunt	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to hypoxia	Cellular tumor antigen p53	Homo sapiens (human)
regulation of fibroblast apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of reactive oxygen species metabolic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of reactive oxygen species metabolic process	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of stem cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of cellular senescence	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of intrinsic apoptotic signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
G2/M transition of mitotic cell cycle	ATP-dependent translocase ABCB1	Homo sapiens (human)
xenobiotic metabolic process	ATP-dependent translocase ABCB1	Homo sapiens (human)
response to xenobiotic stimulus	ATP-dependent translocase ABCB1	Homo sapiens (human)
phospholipid translocation	ATP-dependent translocase ABCB1	Homo sapiens (human)
terpenoid transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
regulation of response to osmotic stress	ATP-dependent translocase ABCB1	Homo sapiens (human)
transmembrane transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
transepithelial transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
stem cell proliferation	ATP-dependent translocase ABCB1	Homo sapiens (human)
ceramide translocation	ATP-dependent translocase ABCB1	Homo sapiens (human)
export across plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
transport across blood-brain barrier	ATP-dependent translocase ABCB1	Homo sapiens (human)
positive regulation of anion channel activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
carboxylic acid transmembrane transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
xenobiotic detoxification by transmembrane export across the plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
xenobiotic transport across blood-brain barrier	ATP-dependent translocase ABCB1	Homo sapiens (human)
regulation of chloride transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
negative regulation of endothelial cell proliferation	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukocyte chemotaxis involved in inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukocyte migration involved in inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukotriene production involved in inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukotriene metabolic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
humoral immune response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of angiogenesis	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukotriene biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
lipoxygenase pathway	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
positive regulation of bone mineralization	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
dendritic cell migration	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
glucose homeostasis	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
long-chain fatty acid biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of fat cell differentiation	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of insulin secretion	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of vascular wound healing	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of wound healing	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of inflammatory response to wounding	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of cytokine production involved in inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of cellular response to oxidative stress	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukotriene A4 biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of reactive oxygen species biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of response to endoplasmic reticulum stress	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of sprouting angiogenesis	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
positive regulation of leukocyte adhesion to arterial endothelial cell	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
lipoxin biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
arachidonic acid metabolic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
lipid oxidation	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
gamma-aminobutyric acid signaling pathway	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
synaptic transmission, GABAergic	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
chloride transmembrane transport	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
inhibitory synapse assembly	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
regulation of postsynaptic membrane potential	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
gamma-aminobutyric acid signaling pathway	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
post-embryonic development	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
adult behavior	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
synaptic transmission, GABAergic	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
cellular response to histamine	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
chloride transmembrane transport	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
inhibitory synapse assembly	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
regulation of postsynaptic membrane potential	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
biogenic amine metabolic process	Amine oxidase [flavin-containing] A	Homo sapiens (human)
positive regulation of signal transduction	Amine oxidase [flavin-containing] A	Homo sapiens (human)
dopamine catabolic process	Amine oxidase [flavin-containing] A	Homo sapiens (human)
response to xenobiotic stimulus	Amine oxidase [flavin-containing] B	Homo sapiens (human)
response to toxic substance	Amine oxidase [flavin-containing] B	Homo sapiens (human)
response to aluminum ion	Amine oxidase [flavin-containing] B	Homo sapiens (human)
response to selenium ion	Amine oxidase [flavin-containing] B	Homo sapiens (human)
negative regulation of serotonin secretion	Amine oxidase [flavin-containing] B	Homo sapiens (human)
phenylethylamine catabolic process	Amine oxidase [flavin-containing] B	Homo sapiens (human)
substantia nigra development	Amine oxidase [flavin-containing] B	Homo sapiens (human)
response to lipopolysaccharide	Amine oxidase [flavin-containing] B	Homo sapiens (human)
dopamine catabolic process	Amine oxidase [flavin-containing] B	Homo sapiens (human)
response to ethanol	Amine oxidase [flavin-containing] B	Homo sapiens (human)
positive regulation of dopamine metabolic process	Amine oxidase [flavin-containing] B	Homo sapiens (human)
hydrogen peroxide biosynthetic process	Amine oxidase [flavin-containing] B	Homo sapiens (human)
response to corticosterone	Amine oxidase [flavin-containing] B	Homo sapiens (human)
gamma-aminobutyric acid signaling pathway	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
chemical synaptic transmission	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
synaptic transmission, GABAergic	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
regulation of postsynaptic membrane potential	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
inner ear receptor cell development	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
innervation	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
cellular response to histamine	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
cochlea development	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
chloride transmembrane transport	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
inhibitory synapse assembly	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
regulation of membrane potential	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
UDP biosynthetic process	Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)
'de novo' UMP biosynthetic process	Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)
pyrimidine ribonucleotide biosynthetic process	Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)
'de novo' pyrimidine nucleobase biosynthetic process	Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)
thermoception	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
fever generation	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
microglial cell activation	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
diet induced thermogenesis	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
peptide secretion	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
negative regulation of systemic arterial blood pressure	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
lipid metabolic process	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cell surface receptor signaling pathway	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
positive regulation of cytosolic calcium ion concentration	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
chemosensory behavior	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
negative regulation of heart rate	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
negative regulation of mitochondrial membrane potential	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
glutamate secretion	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
calcium-mediated signaling	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cellular response to heat	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
positive regulation of apoptotic process	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
response to peptide hormone	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
positive regulation of nitric oxide biosynthetic process	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
behavioral response to pain	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
sensory perception of mechanical stimulus	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
detection of temperature stimulus involved in thermoception	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
detection of temperature stimulus involved in sensory perception of pain	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of pain	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
protein homotetramerization	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
excitatory postsynaptic potential	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
smooth muscle contraction involved in micturition	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
calcium ion transmembrane transport	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cellular response to alkaloid	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cellular response to ATP	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cellular response to tumor necrosis factor	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cellular response to acidic pH	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cellular response to temperature stimulus	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
negative regulation of establishment of blood-brain barrier	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
calcium ion import across plasma membrane	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
response to capsazepine	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cellular response to nerve growth factor stimulus	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
inositol phosphate metabolic process	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
phosphatidylinositol phosphate biosynthetic process	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
negative regulation of cold-induced thermogenesis	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
inositol phosphate biosynthetic process	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
cell population proliferation	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
positive regulation of B cell proliferation	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
nuclear DNA replication	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
signal transduction in response to DNA damage	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediator	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
isotype switching	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
positive regulation of DNA replication	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
positive regulation of isotype switching to IgG isotypes	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
DNA clamp unloading	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
regulation of mitotic cell cycle phase transition	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediator	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
positive regulation of cell cycle G2/M phase transition	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
negative regulation of receptor internalization	Ataxin-2	Homo sapiens (human)
regulation of translation	Ataxin-2	Homo sapiens (human)
RNA metabolic process	Ataxin-2	Homo sapiens (human)
P-body assembly	Ataxin-2	Homo sapiens (human)
stress granule assembly	Ataxin-2	Homo sapiens (human)
RNA transport	Ataxin-2	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
arylesterase activity	Carbonic anhydrase 1	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 1	Homo sapiens (human)
protein binding	Carbonic anhydrase 1	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 1	Homo sapiens (human)
hydro-lyase activity	Carbonic anhydrase 1	Homo sapiens (human)
cyanamide hydratase activity	Carbonic anhydrase 1	Homo sapiens (human)
arylesterase activity	Carbonic anhydrase 2	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 2	Homo sapiens (human)
protein binding	Carbonic anhydrase 2	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 2	Homo sapiens (human)
cyanamide hydratase activity	Carbonic anhydrase 2	Homo sapiens (human)
cytokine activity	Interferon beta	Homo sapiens (human)
cytokine receptor binding	Interferon beta	Homo sapiens (human)
type I interferon receptor binding	Interferon beta	Homo sapiens (human)
protein binding	Interferon beta	Homo sapiens (human)
chloramphenicol O-acetyltransferase activity	Interferon beta	Homo sapiens (human)
TAP binding	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
signaling receptor binding	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
protein binding	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
peptide antigen binding	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
TAP binding	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
protein-folding chaperone binding	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
transcription cis-regulatory region binding	Cellular tumor antigen p53	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specific	Cellular tumor antigen p53	Homo sapiens (human)
cis-regulatory region sequence-specific DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
core promoter sequence-specific DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
TFIID-class transcription factor complex binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specific	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specific	Cellular tumor antigen p53	Homo sapiens (human)
protease binding	Cellular tumor antigen p53	Homo sapiens (human)
p53 binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
chromatin binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription factor activity	Cellular tumor antigen p53	Homo sapiens (human)
mRNA 3'-UTR binding	Cellular tumor antigen p53	Homo sapiens (human)
copper ion binding	Cellular tumor antigen p53	Homo sapiens (human)
protein binding	Cellular tumor antigen p53	Homo sapiens (human)
zinc ion binding	Cellular tumor antigen p53	Homo sapiens (human)
enzyme binding	Cellular tumor antigen p53	Homo sapiens (human)
receptor tyrosine kinase binding	Cellular tumor antigen p53	Homo sapiens (human)
ubiquitin protein ligase binding	Cellular tumor antigen p53	Homo sapiens (human)
histone deacetylase regulator activity	Cellular tumor antigen p53	Homo sapiens (human)
ATP-dependent DNA/DNA annealing activity	Cellular tumor antigen p53	Homo sapiens (human)
identical protein binding	Cellular tumor antigen p53	Homo sapiens (human)
histone deacetylase binding	Cellular tumor antigen p53	Homo sapiens (human)
protein heterodimerization activity	Cellular tumor antigen p53	Homo sapiens (human)
protein-folding chaperone binding	Cellular tumor antigen p53	Homo sapiens (human)
protein phosphatase 2A binding	Cellular tumor antigen p53	Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor binding	Cellular tumor antigen p53	Homo sapiens (human)
14-3-3 protein binding	Cellular tumor antigen p53	Homo sapiens (human)
MDM2/MDM4 family protein binding	Cellular tumor antigen p53	Homo sapiens (human)
disordered domain specific binding	Cellular tumor antigen p53	Homo sapiens (human)
general transcription initiation factor binding	Cellular tumor antigen p53	Homo sapiens (human)
molecular function activator activity	Cellular tumor antigen p53	Homo sapiens (human)
promoter-specific chromatin binding	Cellular tumor antigen p53	Homo sapiens (human)
protein binding	ATP-dependent translocase ABCB1	Homo sapiens (human)
ATP binding	ATP-dependent translocase ABCB1	Homo sapiens (human)
ABC-type xenobiotic transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
efflux transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
ATP hydrolysis activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
ubiquitin protein ligase binding	ATP-dependent translocase ABCB1	Homo sapiens (human)
ATPase-coupled transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
xenobiotic transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
carboxylic acid transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
phosphatidylcholine floppase activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
phosphatidylethanolamine flippase activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
ceramide floppase activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
floppase activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
arachidonate 5-lipoxygenase activity	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
arachidonate 12(S)-lipoxygenase activity	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
iron ion binding	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
protein binding	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
hydrolase activity	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
arachidonate 8(S)-lipoxygenase activity	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
GABA receptor activity	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
GABA-gated chloride ion channel activity	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
GABA-A receptor activity	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
GABA-gated chloride ion channel activity	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potential	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
chloride channel activity	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
benzodiazepine receptor activity	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
GABA-A receptor activity	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
GABA-gated chloride ion channel activity	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
GABA-A receptor activity	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
chloride channel activity	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
protein binding	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
GABA-gated chloride ion channel activity	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potential	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
GABA-A receptor activity	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
chloride channel activity	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
neurotransmitter receptor activity	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
benzodiazepine receptor activity	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
protein binding	Amine oxidase [flavin-containing] A	Homo sapiens (human)
primary amine oxidase activity	Amine oxidase [flavin-containing] A	Homo sapiens (human)
aliphatic amine oxidase activity	Amine oxidase [flavin-containing] A	Homo sapiens (human)
monoamine oxidase activity	Amine oxidase [flavin-containing] A	Homo sapiens (human)
flavin adenine dinucleotide binding	Amine oxidase [flavin-containing] A	Homo sapiens (human)
protein binding	Amine oxidase [flavin-containing] B	Homo sapiens (human)
primary amine oxidase activity	Amine oxidase [flavin-containing] B	Homo sapiens (human)
electron transfer activity	Amine oxidase [flavin-containing] B	Homo sapiens (human)
identical protein binding	Amine oxidase [flavin-containing] B	Homo sapiens (human)
aliphatic amine oxidase activity	Amine oxidase [flavin-containing] B	Homo sapiens (human)
monoamine oxidase activity	Amine oxidase [flavin-containing] B	Homo sapiens (human)
flavin adenine dinucleotide binding	Amine oxidase [flavin-containing] B	Homo sapiens (human)
GABA receptor activity	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
GABA-gated chloride ion channel activity	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
GABA-A receptor activity	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
chloride channel activity	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potential	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
neurotransmitter receptor activity	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
chloride channel activity	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
dihydroorotase activity	Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)
protein binding	Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)
dihydroorotate dehydrogenase (quinone) activity	Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)
dihydroorotate dehydrogenase activity	Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)
transmembrane signaling receptor activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
extracellular ligand-gated monoatomic ion channel activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
voltage-gated calcium channel activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
calcium channel activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
protein binding	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
calmodulin binding	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
ATP binding	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
intracellularly gated calcium channel activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
chloride channel regulator activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
phosphatidylinositol binding	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
identical protein binding	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
metal ion binding	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
phosphoprotein binding	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
temperature-gated ion channel activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
inositol-1,3,4,5,6-pentakisphosphate kinase activity	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
inositol hexakisphosphate kinase activity	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
inositol heptakisphosphate kinase activity	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
inositol hexakisphosphate 5-kinase activity	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
protein binding	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
ATP binding	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
inositol hexakisphosphate 1-kinase activity	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
inositol hexakisphosphate 3-kinase activity	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
inositol 5-diphosphate pentakisphosphate 5-kinase activity	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
inositol diphosphate tetrakisphosphate kinase activity	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
protein binding	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
ATP binding	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
ATP hydrolysis activity	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
DNA clamp unloader activity	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
DNA binding	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
RNA binding	Ataxin-2	Homo sapiens (human)
epidermal growth factor receptor binding	Ataxin-2	Homo sapiens (human)
protein binding	Ataxin-2	Homo sapiens (human)
mRNA binding	Ataxin-2	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
cytosol	Carbonic anhydrase 1	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 1	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 2	Homo sapiens (human)
cytosol	Carbonic anhydrase 2	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 2	Homo sapiens (human)
myelin sheath	Carbonic anhydrase 2	Homo sapiens (human)
apical part of cell	Carbonic anhydrase 2	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 2	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 2	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 2	Homo sapiens (human)
apical part of cell	Carbonic anhydrase 2	Homo sapiens (human)
extracellular space	Interferon beta	Homo sapiens (human)
extracellular region	Interferon beta	Homo sapiens (human)
Golgi membrane	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
endoplasmic reticulum	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
Golgi apparatus	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
plasma membrane	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
cell surface	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
ER to Golgi transport vesicle membrane	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
membrane	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
secretory granule membrane	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
phagocytic vesicle membrane	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
early endosome membrane	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
recycling endosome membrane	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
extracellular exosome	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
lumenal side of endoplasmic reticulum membrane	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
MHC class I protein complex	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
extracellular space	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
external side of plasma membrane	HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)
nuclear body	Cellular tumor antigen p53	Homo sapiens (human)
nucleus	Cellular tumor antigen p53	Homo sapiens (human)
nucleoplasm	Cellular tumor antigen p53	Homo sapiens (human)
replication fork	Cellular tumor antigen p53	Homo sapiens (human)
nucleolus	Cellular tumor antigen p53	Homo sapiens (human)
cytoplasm	Cellular tumor antigen p53	Homo sapiens (human)
mitochondrion	Cellular tumor antigen p53	Homo sapiens (human)
mitochondrial matrix	Cellular tumor antigen p53	Homo sapiens (human)
endoplasmic reticulum	Cellular tumor antigen p53	Homo sapiens (human)
centrosome	Cellular tumor antigen p53	Homo sapiens (human)
cytosol	Cellular tumor antigen p53	Homo sapiens (human)
nuclear matrix	Cellular tumor antigen p53	Homo sapiens (human)
PML body	Cellular tumor antigen p53	Homo sapiens (human)
transcription repressor complex	Cellular tumor antigen p53	Homo sapiens (human)
site of double-strand break	Cellular tumor antigen p53	Homo sapiens (human)
germ cell nucleus	Cellular tumor antigen p53	Homo sapiens (human)
chromatin	Cellular tumor antigen p53	Homo sapiens (human)
transcription regulator complex	Cellular tumor antigen p53	Homo sapiens (human)
protein-containing complex	Cellular tumor antigen p53	Homo sapiens (human)
cytoplasm	ATP-dependent translocase ABCB1	Homo sapiens (human)
plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
cell surface	ATP-dependent translocase ABCB1	Homo sapiens (human)
membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
apical plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
extracellular exosome	ATP-dependent translocase ABCB1	Homo sapiens (human)
external side of apical plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
extracellular region	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
extracellular space	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear envelope	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear envelope lumen	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nucleoplasm	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
cytosol	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear matrix	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear membrane	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
secretory granule lumen	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
perinuclear region of cytoplasm	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
ficolin-1-rich granule lumen	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear envelope	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
plasma membrane	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
cytoplasmic vesicle membrane	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
GABA-ergic synapse	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
postsynaptic specialization membrane	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
GABA-A receptor complex	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
chloride channel complex	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
GABA receptor complex	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
dendrite membrane	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
postsynapse	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
synapse	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
neuron projection	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
plasma membrane	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
transmembrane transporter complex	Gamma-aminobutyric acid receptor subunit alpha-1	Homo sapiens (human)
plasma membrane	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
axon	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
cytoplasmic vesicle membrane	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
dendrite membrane	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
GABA-ergic synapse	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
postsynaptic specialization membrane	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
GABA-A receptor complex	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
chloride channel complex	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
neuron projection	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
dendrite membrane	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
synapse	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
plasma membrane	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
transmembrane transporter complex	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
postsynapse	Gamma-aminobutyric acid receptor subunit gamma-2	Homo sapiens (human)
plasma membrane	Gamma-aminobutyric acid receptor subunit gamma-2	Rattus norvegicus (Norway rat)
plasma membrane	Glutamate receptor 2	Rattus norvegicus (Norway rat)
mitochondrion	Amine oxidase [flavin-containing] A	Homo sapiens (human)
mitochondrial outer membrane	Amine oxidase [flavin-containing] A	Homo sapiens (human)
cytosol	Amine oxidase [flavin-containing] A	Homo sapiens (human)
mitochondrion	Amine oxidase [flavin-containing] A	Homo sapiens (human)
mitochondrion	Amine oxidase [flavin-containing] B	Homo sapiens (human)
mitochondrial envelope	Amine oxidase [flavin-containing] B	Homo sapiens (human)
mitochondrial outer membrane	Amine oxidase [flavin-containing] B	Homo sapiens (human)
dendrite	Amine oxidase [flavin-containing] B	Homo sapiens (human)
neuronal cell body	Amine oxidase [flavin-containing] B	Homo sapiens (human)
mitochondrion	Amine oxidase [flavin-containing] B	Homo sapiens (human)
plasma membrane	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
cytoplasmic vesicle membrane	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
extracellular exosome	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
GABA-ergic synapse	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
postsynaptic specialization membrane	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
GABA-A receptor complex	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
chloride channel complex	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
plasma membrane	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
synapse	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
neuron projection	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
transmembrane transporter complex	Gamma-aminobutyric acid receptor subunit beta-2	Homo sapiens (human)
plasma membrane	Gamma-aminobutyric acid receptor subunit alpha-1	Rattus norvegicus (Norway rat)
plasma membrane	Gamma-aminobutyric acid receptor subunit beta-2	Rattus norvegicus (Norway rat)
nucleoplasm	Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)
mitochondrion	Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)
mitochondrial inner membrane	Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)
cytosol	Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)
mitochondrial inner membrane	Dihydroorotate dehydrogenase (quinone), mitochondrial	Homo sapiens (human)
plasma membrane	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
external side of plasma membrane	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
membrane	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
dendritic spine membrane	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
neuronal cell body	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
postsynaptic membrane	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
plasma membrane	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
fibrillar center	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
nucleoplasm	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
cytosol	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
nucleus	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
cytoplasm	Inositol hexakisphosphate kinase 1	Homo sapiens (human)
Elg1 RFC-like complex	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
nucleus	ATPase family AAA domain-containing protein 5	Homo sapiens (human)
cytoplasm	Ataxin-2	Homo sapiens (human)
Golgi apparatus	Ataxin-2	Homo sapiens (human)
trans-Golgi network	Ataxin-2	Homo sapiens (human)
cytosol	Ataxin-2	Homo sapiens (human)
cytoplasmic stress granule	Ataxin-2	Homo sapiens (human)
membrane	Ataxin-2	Homo sapiens (human)
perinuclear region of cytoplasm	Ataxin-2	Homo sapiens (human)
ribonucleoprotein complex	Ataxin-2	Homo sapiens (human)
cytoplasmic stress granule	Ataxin-2	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (328)

Assay ID	Title	Year	Journal	Article
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1347083	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810	Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347082	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID504812	Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1677561	Cytotoxicity against human HGC-27 cells assessed as reduction in cell viability after 72 hrs by MTT assay
AID1761599	Toxicity in high fat diet-induced ICR mouse model of hyperlipidemia assessed as change in stomach weight at 25 mg/kg, ig administered once daily for 8 weeks by H and E staining based microscopic analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID316625	Inhibition of D-galactosamine/TNFalpha-induced cell death in ddY mouse hepatocytes assessed as cell viability at 10 uM after 20 hrs by MTT assay	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID1761611	Hypolipidemic activity in human HepG2 cells assessed as reduction in FFA-induced intracellular fat deposition at 50 to 100 uM after 24 hrs by Oil Red O staining based assay	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1677557	Cytotoxicity against human HepG2 cells assessed as reduction in cell viability after 72 hrs by MTT assay
AID465674	Activation of rat GABA alpha-1-beta-2-gamma-2 receptor expressed in xenopus oocytes assessed as potentiation of GABA-induced chloride current at 300 uM after 90 secs by two microplate electrode voltage clamp assay relative to control in presence of flumaz	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	HPLC-based activity profiling: discovery of piperine as a positive GABA(A) receptor modulator targeting a benzodiazepine-independent binding site.
AID316622	Inhibition of D-galactosamine/LPS-induced TNFalpha level in ddY mouse serum at 5 mg/kg, po by ELISA	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID453498	Inhibition of mouse brain MAOB	2010	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 20, Issue:2	Proposed structural basis of interaction of piperine and related compounds with monoamine oxidases.
AID1459823	Inhibition of IL-1beta-induced NFkappaB activation in human OA chondrocytes at 100 ug/ml after 24 hrs by luciferase reporter gene assay relative to control	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis of coumaperine derivatives: Their NF-κB inhibitory effect, inhibition of cell migration and their cytotoxic activity.
AID1761601	Hypolipidemic activity in human HepG2 cells assessed as reduction in FFA-induced TG accumulation after 24 hrs	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1761624	Effect on ABCA1 mRNA expression level in high-fat diet fed mouse small intestine at 25 mg/kg, po by qRT-PCR analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1199424	Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of LPS-induced TNFalpha level at 20 uM after 24 hrs by ELISA relative to untreated control	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Design, synthesis and biological evaluation of piperic acid triazolyl derivatives as potent anti-inflammatory agents.
AID1761583	Hypolipidemic activity in high fat diet-induced ICR mouse hyperlipidemic model assessed as reduction in plasma TG level at 25 mg/kg, ig administered once daily for 8 weeks	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1411730	Inhibition of recombinant human CYP1A1 expressed in baker's yeast-derived microsomes (Sacchrosomes) at 10 uM using 7-ethoxyresorufin substrate by EROD assay relative to control	2018	MedChemComm, Feb-01, Volume: 9, Issue:2	Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy
AID316626	Inhibition of D-galactosamine/TNFalpha-induced cell death in ddY mouse hepatocytes assessed as cell viability at 30 uM after 20 hrs by MTT assay	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID1677559	Cytotoxicity against human BEL-7402/5-FU cells assessed as reduction in cell viability after 72 hrs by MTT assay
AID1199423	Antiinflammatory activity in rat assessed as inhibition of carrageenan-induced paw volume at 20 mg/kg, po administered 1 hr prior to carrageenan challenge measured after 5 hrs relative to vehicle-treated control	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Design, synthesis and biological evaluation of piperic acid triazolyl derivatives as potent anti-inflammatory agents.
AID458989	Cytoprotective activity in mouse L929 cells assessed as inhibition of TNF-alpha-induced cytotoxicity at 10 ug/mL after 44 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Mar-01, Volume: 18, Issue:5	Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa.
AID1555441	Antifungal activity against Candida albicans by serial dilution method	2019	European journal of medicinal chemistry, Aug-15, Volume: 176	Phytochemical and pharmacological attributes of piperine: A bioactive ingredient of black pepper.
AID1506733	Antiproliferative activity in human HeLa cells assessed as reduction in cell number incubated for 48 hrs by SRB assay	2017	MedChemComm, Feb-01, Volume: 8, Issue:2	Synthesis and biological evaluation of (-)-kunstleramide and its derivatives.
AID453034	Hepatoprotective activity in ddY mouse assessed as inhibition of D-galactosamine/LPS-induced liver injury by measuring serum aspartate aminotransferase activity at 2.5 mg/kg, po dosed 1 hr before D-GalN/LPS challenge relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID404403	Antidiabetic activity in mouse 3T3L1 cells assessed as enhancement of triglyceride accumulation at 1 uM	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID1761603	Hypolipidemic activity in normal diet fed ICR mouse assessed as reduction in TC level in liver at 25 mg/kg, ig administered once daily for 8 weeks by H and E staining based microscopic analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID316629	Inhibition of D-galactosamine-induced cell death in ddY mouse hepatocytes assessed as cell viability at 30 uM after 44 hrs by MTT assay	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID1637509	Antibacterial activity against Staphylococcus aureus 1199B overexpressing NorA efflux pump measured after 24 hrs by broth checkerboard method	2016	Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17	Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus.
AID1519680	Cytotoxicity against human SH-SY5Y cells assessed as lysosomal activity by measuring neutral red uptake at 10 to 50 uM incubated for 24 hrs followed by incubation with neutral red solution for 2 hrs by microplate reader analysis (Rvb = >85%)	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID977602	Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	2013	Molecular pharmacology, Jun, Volume: 83, Issue:6	Structure-based identification of OATP1B1/3 inhibitors.
AID718839	Inhibition of MAO-A assessed as inhibition of kyneuramine conversion to 4-hydroxyquinoline after 20 mins by fluorescence assay	2012	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 22, Issue:23	Inhibition of monoamine oxidase by derivatives of piperine, an alkaloid from the pepper plant Piper nigrum, for possible use in Parkinson's disease.
AID1761625	Effect on ABCG5 mRNA expression level in high-fat diet fed mouse small intestine at 25 mg/kg, po by qRT-PCR analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1761594	Toxicity in high fat diet-induced ICR mouse model of hyperlipidemia assessed as change in liver weight at 25 mg/kg, ig administered once daily for 8 weeks by H and E staining based microscopic analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID697853	Inhibition of horse BChE at 2 mg/ml by Ellman's method	2012	Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22	Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID1761608	Effect on ABCA1 protein expression level in high-fat diet fed mouse liver at 25 mg/kg/day by Western blotting analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1761620	Effect on ABCA1 protein expression level in high-fat diet fed mouse small intestine at 25 mg/kg, po by Western blotting analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID977599	Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	2013	Molecular pharmacology, Jun, Volume: 83, Issue:6	Structure-based identification of OATP1B1/3 inhibitors.
AID453025	Hepatoprotective activity in ddY mouse peritoneal macrophages assessed as inhibition of LPS-induced nitric oxide production at 30 uM after 20 hrs by Griess method relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID1761582	Hypolipidemic activity in high fat diet-induced ICR mouse hyperlipidemic model assessed as reduction in plasma TC level at 25 mg/kg, ig administered once daily for 8 weeks	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID510382	Inhibition of Staphylococcus aureus 1199B norA efflux pump by spectrophotometry	2010	European journal of medicinal chemistry, Sep, Volume: 45, Issue:9	Substituted dihydronaphthalenes as efflux pump inhibitors of Staphylococcus aureus.
AID1761623	Upregulation of mRNA protein expression in high-fat diet fed mouse small intestine assessed as fold increase at 25 mg/kg, po by qRT-PCR analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID465673	Activation of rat GABA alpha-1-beta-2-gamma-2 receptor expressed in xenopus oocytes assessed as potentiation of chloride current at 100 uM after 90 secs by two microplate electrode voltage clamp assay	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	HPLC-based activity profiling: discovery of piperine as a positive GABA(A) receptor modulator targeting a benzodiazepine-independent binding site.
AID1459803	Inhibition of NF-kappaB in human L428 cells at 50 ug/ml after 2 hrs by luciferase reporter gene assay relative to control	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis of coumaperine derivatives: Their NF-κB inhibitory effect, inhibition of cell migration and their cytotoxic activity.
AID1637504	Inhibition of NorA efflux pump overexpressed in Staphylococcus aureus 1199B assessed as fold reduction in ethidium bromide MIC at 12.5 ug/ml measured at every 3 mins interval for 30 mins by fluorescence analysis	2016	Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17	Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus.
AID1761588	Hypolipidemic activity in normal diet fed ICR mouse assessed as alteration in plasma TC level at 25 mg/kg, ig administered once daily for 8 weeks	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID316620	Inhibition of D-galactosamine/TNFalpha-induced cell death in ddY mouse hepatocytes at 10 uM after 20 hrs by MTT assay	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID213667	In vitro growth inhibition of amastigotes of Trypanosoma cruzi	2004	Bioorganic & medicinal chemistry letters, Jul-05, Volume: 14, Issue:13	Toxic effects of natural piperine and its derivatives on epimastigotes and amastigotes of Trypanosoma cruzi.
AID1238291	Leishmanicidal activity against promastigote form of Leishmania amazonensis WHOM/BR/75/Josefa assessed as inhibition of parasite growth after 48 hrs by Neubauer's chamber method	2015	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16	Synthesis and biological evaluation of novel piperidine-benzodioxole derivatives designed as potential leishmanicidal drug candidates.
AID1199422	Antiinflammatory activity in rat assessed as inhibition of carrageenan-induced paw volume at 20 mg/kg, po administered 1 hr prior to carrageenan challenge measured after 3 hrs relative to vehicle-treated control	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Design, synthesis and biological evaluation of piperic acid triazolyl derivatives as potent anti-inflammatory agents.
AID1493117	Potentiation of berberin induced antibacterial activity against Staphylococcus aureus SA1199 assessed as berberin IC50 at 200 uM (Rvb = 132.2 +/- 1.1 microM)	2018	Journal of natural products, 03-23, Volume: 81, Issue:3	Biochemometrics to Identify Synergists and Additives from Botanical Medicines: A Case Study with Hydrastis canadensis (Goldenseal).
AID1761597	Toxicity in high fat diet-induced ICR mouse model of hyperlipidemia assessed as change in kidney weight at 25 mg/kg, ig administered once daily for 8 weeks by H and E staining based microscopic analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1193495	Thermodynamic equilibrium solubility, log S of the compound in simulated intestinal fluid at pH 6.8 at RT after 4 hrs by 96 well plate method	2015	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7	Thermodynamic equilibrium solubility measurements in simulated fluids by 96-well plate method in early drug discovery.
AID316631	Inhibition of TNF-alpha-induced cell death in ddY mouse L929 cells assessed as cell viability at 10 uM after 20 hrs by MTT assay	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID1519676	Retention time of compound at pH 7.4 by LC-UV analysis	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID1506735	Antiproliferative activity in human IMR32 cells assessed as reduction in cell number incubated for 48 hrs by SRB assay	2017	MedChemComm, Feb-01, Volume: 8, Issue:2	Synthesis and biological evaluation of (-)-kunstleramide and its derivatives.
AID453024	Hepatoprotective activity in ddY mouse peritoneal macrophages assessed as inhibition of LPS-induced nitric oxide production at 10 uM after 20 hrs by Griess method relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID478380	Agonist activity at human TRPV1 expressed in HEK293 cells assessed as increase in intracellular calcium levels by fluorimetric assay without tetracycline-stimulation	2010	Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9	In vitro TRPV1 activity of piperine derived amides.
AID453495	Inhibition of MAOA in rat brain mitochondria	2010	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 20, Issue:2	Proposed structural basis of interaction of piperine and related compounds with monoamine oxidases.
AID1289008	Drug absorption rate constant in healthy adult human subjects after consumption of 44 mg equivalent of piperine in form of pepper in soup (melahu rasam) by HPLC method
AID478381	Agonist activity at human TRPV1 expressed in tetracycline-stimulated HEK293 cells assessed as increase in intracellular calcium levels by fluorimetric assay relative to control	2010	Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9	In vitro TRPV1 activity of piperine derived amides.
AID1519674	Chromatographic hydrophobicity index of compound at 250 uM at pH 7.4 by HPLC analysis	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID1506732	Antiproliferative activity in human A549 cells assessed as reduction in cell number incubated for 48 hrs by SRB assay	2017	MedChemComm, Feb-01, Volume: 8, Issue:2	Synthesis and biological evaluation of (-)-kunstleramide and its derivatives.
AID718838	Inhibition of MAO-B assessed as inhibition of kyneuramine conversion to 4-hydroxyquinoline after 20 mins by fluorescence assay	2012	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 22, Issue:23	Inhibition of monoamine oxidase by derivatives of piperine, an alkaloid from the pepper plant Piper nigrum, for possible use in Parkinson's disease.
AID1761626	Effect on SR-B1 mRNA expression level in high-fat diet fed mouse small intestine at 25 mg/kg, po by qRT-PCR analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1459799	Inhibition of NF-kappaB in human L428 cells at 10 ug/ml after 2 hrs by luciferase reporter gene assay relative to control	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis of coumaperine derivatives: Their NF-κB inhibitory effect, inhibition of cell migration and their cytotoxic activity.
AID1761593	Toxicity in high fat diet-induced ICR mouse model of hyperlipidemia assessed as change in hepatic morphology at 25 mg/kg, ig administered once daily for 8 weeks by H and E staining based microscopic analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1761595	Toxicity in high fat diet-induced ICR mouse model of hyperlipidemia assessed as change in heart weight at 25 mg/kg, ig administered once daily for 8 weeks by H and E staining based microscopic analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1519697	Induction of P-gp in human Caco2 cells assessed as decrease in Rho123 intracellular accumulation by measuring increase in ratio between fluorescence intensity of Zos-inhibited Rho123 accumulation and fluorescence intensity of non-inhibited Rho123 accumula	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID1199421	Antiinflammatory activity in rat assessed as inhibition of carrageenan-induced paw volume at 20 mg/kg, po administered 1 hr prior to carrageenan challenge measured after 5 hrs (Rvb = 1.70 +/- 0.020 ml)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Design, synthesis and biological evaluation of piperic acid triazolyl derivatives as potent anti-inflammatory agents.
AID1761591	Hypolipidemic activity in normal diet fed ICR mouse assessed as alteration in plasma LDL-C level at 25 mg/kg, ig administered once daily for 8 weeks	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID316617	Inhibition of D-galactosamine/LPS-induced liver injury in ddY mouse assessed as serum GPT level at 10 mg/kg, po	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID1761622	Effect on NPC1L1 protein expression level in high-fat diet fed mouse small intestine at 25 mg/kg, po by Western blotting analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1761615	Effect on ABCA1 mRNA expression level in high-fat diet fed mouse liver at 25 mg/kg/day by qRT-PCR analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID323760	Cytotoxicity against mouse macrophages after 72 hrs	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Novel 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine as trypanocidal agents: chemical and biological studies.
AID1288980	Cmax in Swiss albino mouse serum at 0.3 mg, po by HPLC method
AID657237	Inhibition of MAO-A in Sprague-Dawley rat brain homogenate using kynuramine as substrate preincubated for 10 mins measured by fluorimetric assay	2012	Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9	Synthesis and inhibitory effect of piperine derivates on monoamine oxidase.
AID316612	Inhibition of D-galactosamine/LPS-induced liver injury in ddY mouse assessed as serum GOT level at 2.5 mg/kg, po	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID1761613	Effect on NPC1L1 protein expression level in high-fat diet fed mouse liver at 25 mg/kg/day by Western blotting analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID453026	Hepatoprotective activity in ddY mouse peritoneal macrophages assessed as inhibition of LPS-induced nitric oxide production at 100 uM after 20 hrs by Griess method relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID453497	Inhibition of mouse brain MAOA	2010	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 20, Issue:2	Proposed structural basis of interaction of piperine and related compounds with monoamine oxidases.
AID718835	Binding affinity to bovine serum albumin at 8.9 uM by fluorescence assay	2012	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 22, Issue:23	Inhibition of monoamine oxidase by derivatives of piperine, an alkaloid from the pepper plant Piper nigrum, for possible use in Parkinson's disease.
AID1459800	Inhibition of NF-kappaB in human L428 cells at 20 ug/ml after 2 hrs by luciferase reporter gene assay relative to control	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis of coumaperine derivatives: Their NF-κB inhibitory effect, inhibition of cell migration and their cytotoxic activity.
AID1199420	Antiinflammatory activity in rat assessed as inhibition of carrageenan-induced paw volume at 20 mg/kg, po administered 1 hr prior to carrageenan challenge measured after 3 hrs (Rvb = 1.68 +/- 0.029 ml)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Design, synthesis and biological evaluation of piperic acid triazolyl derivatives as potent anti-inflammatory agents.
AID1193496	Thermodynamic equilibrium solubility, log S of the compound in water at RT after 24 hrs by shake-flask method	2015	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7	Thermodynamic equilibrium solubility measurements in simulated fluids by 96-well plate method in early drug discovery.
AID436581	Inhibition of NorA efflux pump in Staphylococcus aureus 1199B assessed as potentiation of ciprofloxacin-induced antimicrobial activity after 24 hrs by broth checkerboard method	2009	European journal of medicinal chemistry, Oct, Volume: 44, Issue:10	Quantitative structure activity relationship (QSAR) of piperine analogs for bacterial NorA efflux pump inhibitors.
AID679605	TP_TRANSPORTER: inhibition of Digoxin transepithelial transport (basal to apical) (Digoxin: 5 uM) in Caco-2 cells	2002	The Journal of pharmacology and experimental therapeutics, Aug, Volume: 302, Issue:2	Piperine, a major constituent of black pepper, inhibits human P-glycoprotein and CYP3A4.
AID1761600	Hypolipidemic activity in high fat diet-induced ICR mouse hyperlipidemic model assessed as reduction in TG level in liver at 25 mg/kg, ig administered once daily for 8 weeks by H and E staining based microscopic analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1872619	Binding affinity to N-terminal 6His-tagged recombinant human DHODH expressed in Escherichia coli strain BL21 (DE3) by isothermal titration calorimetry analysis	2022	European journal of medicinal chemistry, Mar-15, Volume: 232	Recent advances of human dihydroorotate dehydrogenase inhibitors for cancer therapy: Current development and future perspectives.
AID1555420	Antibacterial activity against Escherichia coli assessed as diameter of zone of inhibition at 100 mg/disc by disc diffusion method	2019	European journal of medicinal chemistry, Aug-15, Volume: 176	Phytochemical and pharmacological attributes of piperine: A bioactive ingredient of black pepper.
AID1872620	Inhibition of N-terminal 6His-tagged recombinant human DHODH expressed in Escherichia coli strain BL21 (DE3) using dihydroorotate as substrate and CoQ6 as co-substrate incubated for 10 mins by DCIP dye based analysis	2022	European journal of medicinal chemistry, Mar-15, Volume: 232	Recent advances of human dihydroorotate dehydrogenase inhibitors for cancer therapy: Current development and future perspectives.
AID316614	Inhibition of D-galactosamine/LPS-induced liver injury in ddY mouse assessed as serum GOT level at 10 mg/kg, po	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID323759	Antiparasitic activity against Trypanosoma cruzi Y amastigotes	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Novel 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine as trypanocidal agents: chemical and biological studies.
AID1377551	Inhibition of P-gp in human MCF7/DOX cells assessed as potentiation of doxorubicin-induced cytotoxicity by measuring fold reduction in doxorubicin IC50 at 5 uM	2017	European journal of medicinal chemistry, Sep-29, Volume: 138	Natural alkaloids as P-gp inhibitors for multidrug resistance reversal in cancer.
AID1761621	Effect on ABCG5 protein expression level in high-fat diet fed mouse small intestine at 25 mg/kg, po by Western blotting analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID453040	Hepatoprotective activity in ddY mouse assessed as inhibition of D-galactosamine/LPS-induced increase in serum TNFalpha level at 5 mg/kg, po dosed 1 hr before D-GalN/LPS challenge relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID1155357	Modulation of GABAA alpha1beta2gamma2S receptor (unknown origin) expressed in Xenopus laevis oocytes assessed as potentiation of GABA-induced chloride ion current at holding potential -70 mV by two-microelectrode voltage clamp assay	2014	Journal of medicinal chemistry, Jul-10, Volume: 57, Issue:13	Efficient modulation of γ-aminobutyric acid type A receptors by piperine derivatives.
AID1555439	Antibacterial activity against Proteus vulgaris by serial dilution method	2019	European journal of medicinal chemistry, Aug-15, Volume: 176	Phytochemical and pharmacological attributes of piperine: A bioactive ingredient of black pepper.
AID500214	Agonist activity at TRPV1	2005	Nature chemical biology, Jul, Volume: 1, Issue:2	Sensing with TRP channels.
AID1491116	Toxicity in 7-days post fertilized zebra fish larvae after 1.5 to 24 hrs by microscopic analysis	2017	Journal of natural products, 05-26, Volume: 80, Issue:5	HPLC-Based Activity Profiling for GABA
AID404405	Antidiabetic activity in mouse 3T3L1 cells assessed as enhancement of triglyceride accumulation at 10 uM	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID343385	Inhibition of Trypanosoma cruzi recombinant trypanothione reductase at 85 uM	2008	Bioorganic & medicinal chemistry, Jul-15, Volume: 16, Issue:14	The use of natural product scaffolds as leads in the search for trypanothione reductase inhibitors.
AID453029	Cytoprotective activity in mouse L929 cells assessed as inhibition of TNF-alpha-induced cytotoxicity at 3 uM by MTT assay relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID453041	Hepatoprotective activity in ddY mouse assessed as inhibition of D-galactosamine/LPS-induced increase in serum TNFalpha level at 10 mg/kg, po dosed 1 hr before D-GalN/LPS challenge relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID740216	Cytotoxicity against human HepG2(2.2.15) cells	2013	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 23, Issue:7	Anti-HBV active constituents from Piper longum.
AID1506734	Antiproliferative activity in human MCF7 cells assessed as reduction in cell number incubated for 48 hrs by SRB assay	2017	MedChemComm, Feb-01, Volume: 8, Issue:2	Synthesis and biological evaluation of (-)-kunstleramide and its derivatives.
AID1637508	Inhibition of NorA efflux pump overexpressed in Staphylococcus aureus 1199B assessed as fold reduction in ciprofloxacin MIC at 12.5 ug/ml measured after 24 hrs by broth checkerboard method	2016	Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17	Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus.
AID465676	Activation of rat GABA alpha-1-beta-2-gamma-2 receptor expressed in xenopus oocytes assessed as potentiation of GABA-induced chloride current at 1 uM after 90 secs by two microplate electrode voltage clamp assay	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	HPLC-based activity profiling: discovery of piperine as a positive GABA(A) receptor modulator targeting a benzodiazepine-independent binding site.
AID657239	Selectivity ratio of IC50 for Sprague-Dawley rat MAO-B to IC50 for Sprague-Dawley rat MAO-A	2012	Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9	Synthesis and inhibitory effect of piperine derivates on monoamine oxidase.
AID1761596	Toxicity in high fat diet-induced ICR mouse model of hyperlipidemia assessed as change in lung weight at 25 mg/kg, ig administered once daily for 8 weeks by H and E staining based microscopic analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1637503	Antibacterial activity against wild-type Staphylococcus aureus 1199 expressing NorA efflux pump measured at every 3 mins interval for 30 mins by fluorescence analysis	2016	Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17	Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus.
AID1105350	Insecticidal activity against Aedes aegypti assessed as lethal compound dose per mosquito measured after 24 hr post topical application	2010	Toxins, 08, Volume: 2, Issue:8	Natural toxins for use in pest management.
AID1519691	Inhibition of human microsomal MAO-B expressed in baculovirus infected BTI-TN-5B1-4 cells assessed as reduction in 4-hydroxyquinoline formation using kynuramine as substrate preincubated with substrate for 10 mins followed by enzyme addition by spectropho	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID740212	Selectivity index, ratio of CC50 for human HepG2(2.2.15) cells to IC50 for Hepatitis B virus-infected human HepG2(2.2.15) cells assessed as inhibition of HBeAg secretion	2013	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 23, Issue:7	Anti-HBV active constituents from Piper longum.
AID1603728	Inhibition of human PMNL 5-LOX using arachidonic acid as substrate after 5 mins by HPLC method	2019	Bioorganic & medicinal chemistry, 09-01, Volume: 27, Issue:17	5-Lipoxygenase as a drug target: A review on trends in inhibitors structural design, SAR and mechanism based approach.
AID1555425	Antifungal activity against Candida albicans assessed as diameter of zone of inhibition at 100 mg/disc by disc diffusion method	2019	European journal of medicinal chemistry, Aug-15, Volume: 176	Phytochemical and pharmacological attributes of piperine: A bioactive ingredient of black pepper.
AID1193500	Thermodynamic equilibrium solubility, log S of the compound	2015	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7	Thermodynamic equilibrium solubility measurements in simulated fluids by 96-well plate method in early drug discovery.
AID1459822	Inhibition of LPS-induced NFkappaB activation in mouse RAW264.7 cells at 100 ug/ml after 24 hrs by luciferase reporter gene assay relative to control	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis of coumaperine derivatives: Their NF-κB inhibitory effect, inhibition of cell migration and their cytotoxic activity.
AID453031	Cytoprotective activity in mouse L929 cells assessed as inhibition of TNF-alpha-induced cytotoxicity at 30 uM by MTT assay relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID1555436	Antibacterial activity against Escherichia coli by serial dilution method	2019	European journal of medicinal chemistry, Aug-15, Volume: 176	Phytochemical and pharmacological attributes of piperine: A bioactive ingredient of black pepper.
AID1491117	Anticonvulsant activity in 7-days post fertilized zebra fish larvae assessed as reduction in pentylenetetrazol-induced locomotor activity by measuring total distance traveled by larvae pretreated for 3 hrs followed by pentylenetetrazol addition measured a	2017	Journal of natural products, 05-26, Volume: 80, Issue:5	HPLC-Based Activity Profiling for GABA
AID453012	Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine-induced cytotoxicity at 3 uM after 44 hrs by MTT assay relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID1761589	Hypolipidemic activity in normal diet fed ICR mouse assessed as alteration in plasma TG level at 25 mg/kg, ig administered once daily for 8 weeks	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID697852	Inhibition of electric eel AChE at 2 mg/ml by Ellman's method	2012	Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22	Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID478379	Agonist activity at human TRPV1 expressed in tetracycline-stimulated HEK293 cells assessed as increase in intracellular calcium levels by fluorimetric assay	2010	Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9	In vitro TRPV1 activity of piperine derived amides.
AID1891770	Positive allosteric modulation of GABAA alpha1beta2gamma2 receptor (unknown origin) stably expressed in CHO cells assessed as activation of GABA-induced response in presence of GABA by FLIPR assay	2022	Journal of natural products, 05-27, Volume: 85, Issue:5	Clerodane Diterpenes from
AID1761592	Hypolipidemic activity in high fat diet-induced ICR mouse hyperlipidemic model assessed as reduction in fat accumulation in liver at 25 mg/kg, ig administered once daily for 8 weeks by H and E staining based microscopic analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1519677	Inhibition of P-gp in human Caco2 cells assessed as decrease in Rho123 efflux by measuring decrease in ratio between fluorescence intensity of Zos-inhibited Rho123 accumulation and fluorescence intensity of non-inhibited Rho123 accumulation at 10 uM using	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID453030	Cytoprotective activity in mouse L929 cells assessed as inhibition of TNF-alpha-induced cytotoxicity at 10 uM by MTT assay relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID1199428	Ulcerogenic effect in Albino Wistar rat assessed as damage in gastric mucosa at 60 mg, po after 5 hrs	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Design, synthesis and biological evaluation of piperic acid triazolyl derivatives as potent anti-inflammatory agents.
AID1289007	AUC (0 to infinity) in healthy adult human subjects after consumption of 44 mg equivalent of piperine in form of pepper in soup (melahu rasam) by HPLC method
AID453014	Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine-induced cytotoxicity at 30 uM after 44 hrs by MTT assay relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID1555422	Antibacterial activity against Klebsiella pneumoniae assessed as diameter of zone of inhibition at 100 mg/disc by disc diffusion method	2019	European journal of medicinal chemistry, Aug-15, Volume: 176	Phytochemical and pharmacological attributes of piperine: A bioactive ingredient of black pepper.
AID1637507	Inhibition of NorA efflux pump overexpressed in Staphylococcus aureus 1199B assessed as concentration required for four-fold reduction in ciprofloxacin MIC measured after 24 hrs by broth checkerboard method relative to control	2016	Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17	Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus.
AID1761609	Hypolipidemic activity in human HepG2 cells assessed as reduction in FFA-induced lipid accumulation incubated for 24 hrs by Oil Red O staining based assay	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID494524	Cytotoxicity against human PBMC at IC50 concentration after 48 hrs by MTT assay	2010	European journal of medicinal chemistry, Aug, Volume: 45, Issue:8	Synthesis and antileishmanial activity of piperoyl-amino acid conjugates.
AID1555437	Antibacterial activity against Staphylococcus aureus by serial dilution method	2019	European journal of medicinal chemistry, Aug-15, Volume: 176	Phytochemical and pharmacological attributes of piperine: A bioactive ingredient of black pepper.
AID510387	Inhibition of Staphylococcus aureus 1199 norA efflux pump assessed as potentiation of ciprofloxacin MIC by spectrophotometry	2010	European journal of medicinal chemistry, Sep, Volume: 45, Issue:9	Substituted dihydronaphthalenes as efflux pump inhibitors of Staphylococcus aureus.
AID453042	Hepatoprotective activity in ddY mouse assessed as inhibition of D-galactosamine/LPS-induced increase in serum TNFalpha level at 20 mg/kg, po dosed 1 hr before D-GalN/LPS challenge relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID718837	Permeability of the compound by PAMPA	2012	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 22, Issue:23	Inhibition of monoamine oxidase by derivatives of piperine, an alkaloid from the pepper plant Piper nigrum, for possible use in Parkinson's disease.
AID316615	Inhibition of D-galactosamine/LPS-induced liver injury in ddY mouse assessed as serum GPT level at 2.5 mg/kg, po	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID1761604	Effect on ABCG5 protein expression level in high-fat diet fed mouse liver at 25 mg/kg/day by Western blotting analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID389756	Inhibition of NorA efflux pump in Staphylococcus aureus 1199 assessed as fold reduction of ciprofloxacin MIC at 50 ug/ml	2008	Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22	Piperine analogs as potent Staphylococcus aureus NorA efflux pump inhibitors.
AID316628	Inhibition of D-galactosamine-induced cell death in ddY mouse hepatocytes assessed as cell viability at 10 uM after 44 hrs by MTT assay	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID1555438	Antibacterial activity against Klebsiella pneumoniae by serial dilution method	2019	European journal of medicinal chemistry, Aug-15, Volume: 176	Phytochemical and pharmacological attributes of piperine: A bioactive ingredient of black pepper.
AID316627	Inhibition of D-galactosamine/TNFalpha-induced cell death in ddY mouse hepatocytes assessed as cell viability at 100 uM after 20 hrs by MTT assay	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID1677558	Cytotoxicity against human Bel-7402 cells assessed as reduction in cell viability after 72 hrs by MTT assay
AID1761617	Effect on NPC1 mRNA expression level in high-fat diet fed mouse liver at 25 mg/kg/day by qRT-PCR analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID436579	Inhibition of NorA efflux pump in Staphylococcus aureus 1199B assessed as accumulation of ethidium bromide after 24 hrs by broth checkerboard method	2009	European journal of medicinal chemistry, Oct, Volume: 44, Issue:10	Quantitative structure activity relationship (QSAR) of piperine analogs for bacterial NorA efflux pump inhibitors.
AID1459801	Inhibition of NF-kappaB in human L428 cells at 30 ug/ml after 2 hrs by luciferase reporter gene assay relative to control	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis of coumaperine derivatives: Their NF-κB inhibitory effect, inhibition of cell migration and their cytotoxic activity.
AID510384	Inhibition of Staphylococcus aureus 1199B norA efflux pump assessed as potentiation of ciprofloxacin MIC by spectrophotometry	2010	European journal of medicinal chemistry, Sep, Volume: 45, Issue:9	Substituted dihydronaphthalenes as efflux pump inhibitors of Staphylococcus aureus.
AID1459804	Inhibition of NF-kappaB in human L428 cells after 2 hrs by luciferase reporter gene assay	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis of coumaperine derivatives: Their NF-κB inhibitory effect, inhibition of cell migration and their cytotoxic activity.
AID1761619	Upregulation of ABCG8 mRNA expression in high-fat diet fed mouse liver at 25 mg/kg/day by qRT-PCR analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID316623	Inhibition of D-galactosamine/LPS-induced TNFalpha level in ddY mouse serum at 10 mg/kg, po by ELISA	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID316613	Inhibition of D-galactosamine/LPS-induced liver injury in ddY mouse assessed as serum GOT level at 5 mg/kg, po	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID453019	Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine/TNFalpha-induced cytotoxicity at 10 uM after 20 hrs by MTT assay relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID458991	Cytoprotective activity in mouse L929 cells assessed as inhibition of TNF-alpha-induced cytotoxicity at 100 ug/mL after 44 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Mar-01, Volume: 18, Issue:5	Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa.
AID453036	Hepatoprotective activity in ddY mouse assessed as inhibition of D-galactosamine/LPS-induced liver injury by measuring serum aspartate aminotransferase activity at 10 mg/kg, po dosed 1 hr before D-GalN/LPS challenge relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID453035	Hepatoprotective activity in ddY mouse assessed as inhibition of D-galactosamine/LPS-induced liver injury by measuring serum aspartate aminotransferase activity at 5 mg/kg, po dosed 1 hr before D-GalN/LPS challenge relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID465672	Activation of rat GABA alpha-1-beta-2-gamma-2 receptor expressed in xenopus oocytes assessed as potentiation of GABA-induced chloride current after 90 secs by two microplate electrode voltage clamp assay	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	HPLC-based activity profiling: discovery of piperine as a positive GABA(A) receptor modulator targeting a benzodiazepine-independent binding site.
AID1289004	Cmax in healthy adult human subjects after consumption of 44 mg equivalent of piperine in form of pepper in soup (melahu rasam) by HPLC method
AID1761587	Hypolipidemic activity in high fat diet-induced ICR mouse hyperlipidemic model assessed as increase in plasma HDL-C level at 25 mg/kg, ig administered once daily for 8 weeks	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1555440	Antibacterial activity against Pseudomonas aeruginosa by serial dilution method	2019	European journal of medicinal chemistry, Aug-15, Volume: 176	Phytochemical and pharmacological attributes of piperine: A bioactive ingredient of black pepper.
AID436580	Inhibition of NorA efflux pump in Staphylococcus aureus 1199B assessed as reduction of ciprofloxacin MIC after 24 hrs by broth checkerboard method	2009	European journal of medicinal chemistry, Oct, Volume: 44, Issue:10	Quantitative structure activity relationship (QSAR) of piperine analogs for bacterial NorA efflux pump inhibitors.
AID213669	In vitro growth inhibition of epimastigotes of Trypanosoma cruzi	2004	Bioorganic & medicinal chemistry letters, Jul-05, Volume: 14, Issue:13	Toxic effects of natural piperine and its derivatives on epimastigotes and amastigotes of Trypanosoma cruzi.
AID1866565	Inhibition of MAPK/ERK signalling pathway in human A2058 cells harbouring BRAF V600E and PTEN deletion mutant coexpressing ERK-KTR fused mScarlett fluorophore at 1.56 to 200 uM incubated for 2 hrs by high-content screening microscopic analysis	2022	Journal of natural products, 04-22, Volume: 85, Issue:4	High-Content Screening Pipeline for Natural Products Targeting Oncogenic Signaling in Melanoma.
AID1459802	Inhibition of NF-kappaB in human L428 cells at 40 ug/ml after 2 hrs by luciferase reporter gene assay relative to control	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis of coumaperine derivatives: Their NF-κB inhibitory effect, inhibition of cell migration and their cytotoxic activity.
AID736709	Potentiation of NGF-induced neurite outgrowth in rat PC12 cells at 0.1 to 10 uM after 4 days using methylene blue staining by phase-contrast microscopy	2013	Journal of natural products, Apr-26, Volume: 76, Issue:4	Evaluation of constituents of Piper retrofractum fruits on neurotrophic activity.
AID1761610	Upregulation of SR-B1 protein expression level in high-fat diet fed mouse liver at 25 mg/kg/day by Western blotting analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1193497	Thermodynamic equilibrium solubility, log S of the compound PBS at pH 7.4 at RT after 24 hrs by shake-flask method	2015	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7	Thermodynamic equilibrium solubility measurements in simulated fluids by 96-well plate method in early drug discovery.
AID1761605	Hypolipidemic activity in normal diet fed ICR mouse assessed as reduction in TG level in liver at 25 mg/kg, ig administered once daily for 8 weeks by H and E staining based microscopic analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1519690	Selectivity index, ratio of IC50 for human microsomal MAO-A expressed in baculovirus infected BTN-TN-5B1-4 cells to IC50 for human microsomal MAO-B expressed in baculovirus infected BTN-TN-5B1-4 cells using kynuramine as substrate	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID323757	Antiparasitic activity against Trypanosoma cruzi Y epimastigote	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Novel 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine as trypanocidal agents: chemical and biological studies.
AID1193493	Thermodynamic equilibrium solubility, log S of the compound in PBS at pH 7.4 at RT after 4 hrs by 96 well plate method	2015	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7	Thermodynamic equilibrium solubility measurements in simulated fluids by 96-well plate method in early drug discovery.
AID1761612	Effect on ABCG8 protein expression level in high-fat diet fed mouse liver at 25 mg/kg/day by Western blotting analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID453015	Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine-induced cytotoxicity at 100 uM after 44 hrs by MTT assay relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID740214	Selectivity index, ratio of CC50 for human HepG2(2.2.15) cells to IC50 for Hepatitis B virus-infected human HepG2(2.2.15) cells assessed as inhibition of HBsAg secretion	2013	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 23, Issue:7	Anti-HBV active constituents from Piper longum.
AID1761590	Hypolipidemic activity in normal diet fed ICR mouse assessed as alteration in plasma HDL-C level at 25 mg/kg, ig administered once daily for 8 weeks	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1761598	Toxicity in high fat diet-induced ICR mouse model of hyperlipidemia assessed as change in spleen weight at 25 mg/kg, ig administered once daily for 8 weeks by H and E staining based microscopic analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID478384	Displacement of [3H]resiniferatoxin from human TRPV1	2010	Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9	In vitro TRPV1 activity of piperine derived amides.
AID453023	Hepatoprotective activity in ddY mouse peritoneal macrophages assessed as inhibition of LPS-induced nitric oxide production at 3 uM after 20 hrs by Griess method relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID1555423	Antibacterial activity against Proteus vulgaris assessed as diameter of zone of inhibition at 100 mg/disc by disc diffusion method	2019	European journal of medicinal chemistry, Aug-15, Volume: 176	Phytochemical and pharmacological attributes of piperine: A bioactive ingredient of black pepper.
AID1761627	Effect on NPC1 mRNA expression level in high-fat diet fed mouse small intestine at 25 mg/kg, po by qRT-PCR analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1761614	Effect on ABCG1 mRNA expression level in high-fat diet fed mouse liver at 25 mg/kg/day by qRT-PCR analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID494523	Antileishmanial activity against Leishmania donovani promastigotes after 48 hrs by MTT assay	2010	European journal of medicinal chemistry, Aug, Volume: 45, Issue:8	Synthesis and antileishmanial activity of piperoyl-amino acid conjugates.
AID657238	Inhibition of MAO-B in Sprague-Dawley rat brain homogenate using kynuramine as substrate preincubated for 10 mins measured by fluorimetric assay	2012	Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9	Synthesis and inhibitory effect of piperine derivates on monoamine oxidase.
AID406532	Inhibition of NorA efflux pump in Staphylococcus aureus 1199B assessed as fold reduction of ciprofloxacin MIC at 50 ug/ml	2008	Bioorganic & medicinal chemistry, Jul-01, Volume: 16, Issue:13	Citral derived amides as potent bacterial NorA efflux pump inhibitors.
AID465670	Activation of rat GABA alpha-1-beta-2-gamma-2 receptor expressed in xenopus oocytes assessed as potentiation of GABA-induced chloride current at 100 uM after 90 secs by two microplate electrode voltage clamp assay	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	HPLC-based activity profiling: discovery of piperine as a positive GABA(A) receptor modulator targeting a benzodiazepine-independent binding site.
AID1155350	Modulation of GABAA alpha1beta2gamma2S receptor (unknown origin) expressed in Xenopus laevis oocytes assessed as modulation of GABA-induced maximal chloride ion current at holding potential -70 mV by two-microelectrode voltage clamp assay relative to GABA	2014	Journal of medicinal chemistry, Jul-10, Volume: 57, Issue:13	Efficient modulation of γ-aminobutyric acid type A receptors by piperine derivatives.
AID453020	Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine/TNFalpha-induced cytotoxicity at 30 uM after 20 hrs by MTT assay relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID1555421	Antibacterial activity against Staphylococcus aureus assessed as diameter of zone of inhibition at 100 mg/disc by disc diffusion method	2019	European journal of medicinal chemistry, Aug-15, Volume: 176	Phytochemical and pharmacological attributes of piperine: A bioactive ingredient of black pepper.
AID1761602	Hypolipidemic activity in high fat diet-induced ICR mouse hyperlipidemic model assessed as reduction in TC level in liver at 25 mg/kg, ig administered once daily for 8 weeks by H and E staining based microscopic analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID453021	Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine/TNFalpha-induced cytotoxicity after 20 hrs by MTT assay relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID740213	Antiviral activity against Hepatitis B virus-infected human HepG2(2.2.15) cells assessed as inhibition of HBeAg secretion	2013	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 23, Issue:7	Anti-HBV active constituents from Piper longum.
AID494522	Antileishmanial activity against Leishmania donovani amastigotes after 48 hrs by MTT assay	2010	European journal of medicinal chemistry, Aug, Volume: 45, Issue:8	Synthesis and antileishmanial activity of piperoyl-amino acid conjugates.
AID1637502	Inhibition of NorA efflux pump in Staphylococcus aureus 1199 assessed as concentration required for four-fold reduction in ethidium bromide MIC measured at every 3 mins interval for 30 mins by fluorescence analysis	2016	Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17	Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus.
AID1193498	Thermodynamic equilibrium solubility, log S of the compound simulated gastric fluid at pH 1.2 at RT after 24 hrs by shake-flask method	2015	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7	Thermodynamic equilibrium solubility measurements in simulated fluids by 96-well plate method in early drug discovery.
AID494525	Cytotoxicity against human PBMC at 2 times IC50 concentration after 48 hrs by MTT assay	2010	European journal of medicinal chemistry, Aug, Volume: 45, Issue:8	Synthesis and antileishmanial activity of piperoyl-amino acid conjugates.
AID680071	TP_TRANSPORTER: inhibition of Cyclosporin A transepithelial transport (basal to apical) (Cyclosporin A: 1 uM) in Caco-2 cells	2002	The Journal of pharmacology and experimental therapeutics, Aug, Volume: 302, Issue:2	Piperine, a major constituent of black pepper, inhibits human P-glycoprotein and CYP3A4.
AID453032	Cytoprotective activity in mouse L929 cells assessed as inhibition of TNF-alpha-induced cytotoxicity at 100 uM by MTT assay relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID316621	Inhibition of D-galactosamine/TNFalpha-induced cell death in ddY mouse hepatocytes at 30 uM after 20 hrs by MTT assay	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID740215	Antiviral activity against Hepatitis B virus-infected human HepG2(2.2.15) cells assessed as inhibition of HBsAg secretion	2013	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 23, Issue:7	Anti-HBV active constituents from Piper longum.
AID1637506	Antibacterial activity against Staphylococcus aureus 1199B overexpressing NorA efflux pump measured at every 3 mins interval for 30 mins by fluorescence analysis	2016	Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17	Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus.
AID465675	Displacement of [3H]-flumazenil from GABAA receptor	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	HPLC-based activity profiling: discovery of piperine as a positive GABA(A) receptor modulator targeting a benzodiazepine-independent binding site.
AID1761607	Effect on ABCG1 protein expression level in high-fat diet fed mouse liver at 25 mg/kg/day by Western blotting analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1519681	Cytotoxicity against human SH-SY5Y cells assessed as cellular metabolic activity by measuring resazurin reduction at 10 to 50 uM incubated for 24 hrs followed by incubation with resazurin for 2 hrs by fluorescence based assay (Rvb = >85%)	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID316632	Inhibition of TNF-alpha-induced cell death in ddY mouse L929 cells assessed as cell viability at 30 uM after 20 hrs by MTT assay	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID404404	Antidiabetic activity in mouse 3T3L1 cells assessed as enhancement of triglyceride accumulation at 3 uM	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID1761629	Toxicity in high fat diet-induced mouse model of hyperlipidemia assessed as change in food intake at 25 mg/kg, ig administered once daily for 8 weeks	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1193494	Thermodynamic equilibrium solubility, log S of the compound in simulated gastric fluid at pH 1.2 at RT after 4 hrs by 96 well plate method	2015	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7	Thermodynamic equilibrium solubility measurements in simulated fluids by 96-well plate method in early drug discovery.
AID1288981	Tmax in Swiss albino mouse serum at 0.3 mg, po by HPLC method
AID1738629	Neuroprotective activity against H2O2-induced cytotoxicity in rat PC-12 cells assessed as cell viability at 12.5 uM pretreated for 24 hrs followed by H2O2 challenge and measured after 24 hrs by MTT assay (Rvb = 52.81 +/- 6%)	2020	European journal of medicinal chemistry, Aug-01, Volume: 199	Identification and optimization of piperine analogues as neuroprotective agents for the treatment of Parkinson's disease via the activation of Nrf2/keap1 pathway.
AID1761584	Upregulation of ABCG8 protein expression in high-fat diet fed mouse small intestine at 25 mg/kg, po by Western blotting analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID453039	Hepatoprotective activity in ddY mouse assessed as inhibition of D-galactosamine/LPS-induced liver injury by measuring serum alanine aminotransferase activity at 10 mg/kg, po dosed 1 hr before D-GalN/LPS challenge relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID316630	Inhibition of D-galactosamine-induced cell death in ddY mouse hepatocytes assessed as cell viability at 100 uM after 44 hrs by MTT assay	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID404406	Antidiabetic activity in mouse 3T3L1 cells assessed as enhancement of triglyceride accumulation at 30 uM	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID1761586	Hypolipidemic activity in high fat diet-induced ICR mouse hyperlipidemic model assessed as reduction in plasma LDL-C level at 25 mg/kg, ig administered once daily for 8 weeks	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID453038	Hepatoprotective activity in ddY mouse assessed as inhibition of D-galactosamine/LPS-induced liver injury by measuring serum alanine aminotransferase activity at 5 mg/kg, po dosed 1 hr before D-GalN/LPS challenge relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID1377592	Inhibition of P-gp in human MCF7/DOX cells assessed as potentiation of mitoxantrone-induced cytotoxicity by measuring fold reduction in mitoxantrone IC50 at 50 uM after 48 hrs by MTT assay	2017	European journal of medicinal chemistry, Sep-29, Volume: 138	Natural alkaloids as P-gp inhibitors for multidrug resistance reversal in cancer.
AID1761628	Toxicity in high fat diet-induced mouse model of hyperlipidemia assessed as change in body weight at 25 mg/kg, ig administered once daily for 8 weeks	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1289009	Drug elimination rate constant in healthy adult human subjects after consumption of 44 mg equivalent of piperine in form of pepper in soup (melahu rasam) by HPLC method
AID1761585	Effect on SR-B1 protein expression level in high-fat diet fed mouse small intestine at 25 mg/kg, po by Western blotting analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID316633	Inhibition of TNF-alpha-induced cell death in ddY mouse L929 cells assessed as cell viability at 100 uM after 20 hrs by MTT assay	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID1289005	Tmax in healthy adult human subjects after consumption of 44 mg equivalent of piperine in form of pepper in soup (melahu rasam) by HPLC method
AID453037	Hepatoprotective activity in ddY mouse assessed as inhibition of D-galactosamine/LPS-induced liver injury by measuring serum alanine aminotransferase activity at 2.5 mg/kg, po dosed 1 hr before D-GalN/LPS challenge relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID1555424	Antibacterial activity against Pseudomonas aeruginosa assessed as diameter of zone of inhibition at 100 mg/disc by disc diffusion method	2019	European journal of medicinal chemistry, Aug-15, Volume: 176	Phytochemical and pharmacological attributes of piperine: A bioactive ingredient of black pepper.
AID1761618	Effect on ABCG5 mRNA expression level in high-fat diet fed mouse liver at 25 mg/kg/day by qRT-PCR analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID1677560	Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability after 72 hrs by MTT assay
AID453018	Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine/TNFalpha-induced cytotoxicity at 3 uM after 20 hrs by MTT assay relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID1761616	Effect on SR-B1 mRNA expression level in high-fat diet fed mouse liver at 25 mg/kg/day by qRT-PCR analysis	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID453033	Cytoprotective activity in mouse L929 cells assessed as inhibition of TNF-alpha-induced cytotoxicity by MTT assay relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID1493113	Potentiation of berberin induced antibacterial activity against Staphylococcus aureus SA1199 assessed as berberin MIC at 200 uM (Rvb = 238 microM)	2018	Journal of natural products, 03-23, Volume: 81, Issue:3	Biochemometrics to Identify Synergists and Additives from Botanical Medicines: A Case Study with Hydrastis canadensis (Goldenseal).
AID1193492	Thermodynamic equilibrium solubility, log S of the compound in water at RT after 4 hrs by 96 well plate method	2015	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7	Thermodynamic equilibrium solubility measurements in simulated fluids by 96-well plate method in early drug discovery.
AID406534	Inhibition of NorA efflux pump in Staphylococcus aureus 1199 assessed as fold reduction of ciprofloxacin MIC at 50 ug/ml	2008	Bioorganic & medicinal chemistry, Jul-01, Volume: 16, Issue:13	Citral derived amides as potent bacterial NorA efflux pump inhibitors.
AID453013	Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine-induced cytotoxicity at 10 uM after 44 hrs by MTT assay relative to untreated control	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID316619	Inhibition of D-galactosamine/TNFalpha-induced cell death in ddY mouse hepatocytes at 3 uM after 20 hrs by MTT assay	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID1377591	Inhibition of P-gp in human A549/DDP cells assessed as potentiation of doxorubicin-induced cytotoxicity	2017	European journal of medicinal chemistry, Sep-29, Volume: 138	Natural alkaloids as P-gp inhibitors for multidrug resistance reversal in cancer.
AID496817	Antimicrobial activity against Trypanosoma cruzi	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID316616	Inhibition of D-galactosamine/LPS-induced liver injury in ddY mouse assessed as serum GPT level at 5 mg/kg, po	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID1519693	Inhibition of human microsomal MAO-A expressed in baculovirus infected BTI-TN-5B1-4 cells assessed as reduction in 4-hydroxyquinoline formation at 10 uM using kynuramine as substrate preincubated with substrate for 10 mins followed by enzyme inhibition by	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID465671	Activation of rat GABA alpha-1-beta-2-gamma-2 receptor expressed in xenopus oocytes assessed as potentiation of GABA-induced chloride current at 300 uM after 90 secs by two microplate electrode voltage clamp assay	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	HPLC-based activity profiling: discovery of piperine as a positive GABA(A) receptor modulator targeting a benzodiazepine-independent binding site.
AID1637505	Inhibition of NorA efflux pump overexpressed in Staphylococcus aureus 1199B assessed as concentration required for four-fold reduction in ethidium bromide MIC measured at every 3 mins interval for 30 mins by fluorescence analysis	2016	Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17	Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus.
AID1289006	AUC (0 to 12.5 hrs) in healthy adult human subjects after consumption of 44 mg equivalent of piperine in form of pepper in soup (melahu rasam) by HPLC method
AID453496	Inhibition of MAOB in rat brain mitochondria	2010	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 20, Issue:2	Proposed structural basis of interaction of piperine and related compounds with monoamine oxidases.
AID458990	Cytoprotective activity in mouse L929 cells assessed as inhibition of TNF-alpha-induced cytotoxicity at 30 ug/mL after 44 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Mar-01, Volume: 18, Issue:5	Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa.
AID458988	Cytoprotective activity in mouse L929 cells assessed as inhibition of TNF-alpha-induced cytotoxicity at 3 ug/mL after 44 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Mar-01, Volume: 18, Issue:5	Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa.
AID1866568	Inhibition of PI3K/AKT signalling pathway in patient-derived MM121224 cells harboring BRAF V600E/NRAS Q61K mutant coexpressing mutated forkhead box protein 1 allele fused mNeonGreen fluorophore at 200 uM incubated for 2 hrs	2022	Journal of natural products, 04-22, Volume: 85, Issue:4	High-Content Screening Pipeline for Natural Products Targeting Oncogenic Signaling in Melanoma.
AID1614266	Inhibition of recombinant human 5-LOX expressed in Escherichia coli at 20 uM using arachidonic acid as substrate by UV-vis spectrophotometric method relative to control	2019	Bioorganic & medicinal chemistry, 02-15, Volume: 27, Issue:4	Design, synthesis and identification of novel coumaperine derivatives for inhibition of human 5-LOX: Antioxidant, pseudoperoxidase and docking studies.
AID389747	Inhibition of NorA efflux pump in Staphylococcus aureus 1199B assessed as fold reduction of ciprofloxacin MIC at 50 ug/ml	2008	Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22	Piperine analogs as potent Staphylococcus aureus NorA efflux pump inhibitors.
AID1193499	Thermodynamic equilibrium solubility, log S of the compound simulated intestinal fluid at pH 6.8 at RT after 24 hrs by shake-flask method	2015	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7	Thermodynamic equilibrium solubility measurements in simulated fluids by 96-well plate method in early drug discovery.
AID1637510	Inhibition of NorA efflux pump in Staphylococcus aureus 1199 assessed as fold reduction in ethidium bromide MIC at 12.5 mg/ml measured at every 3 mins interval for 30 mins by fluorescence analysis	2016	Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17	Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus.
AID316624	Inhibition of D-galactosamine/LPS-induced TNFalpha level in ddY mouse serum at 20 mg/kg, po by ELISA	2008	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6	Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID1519675	Chromatographic hydrophobicity index, log D of compound at 250 uM at pH 7.4 by HPLC analysis	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID1761606	Cytotoxicity against human HepG2 cells assessed as reduction in cell viability at 1 to 100 uM after 24 hrs by CCK8 assay	2021	Journal of natural products, 02-26, Volume: 84, Issue:2	Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters.
AID465677	Activation of rat GABA alpha-1-beta-2-gamma-2 receptor expressed in xenopus oocytes assessed as potentiation of GABA-induced chloride current at 100 uM after 90 secs by two microplate electrode voltage clamp assay in presence of 1 uM Diazepam	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	HPLC-based activity profiling: discovery of piperine as a positive GABA(A) receptor modulator targeting a benzodiazepine-independent binding site.
AID1347377	DH5-alpha competent E. coli microbial cell viability qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347354	UWB1.289-WTBRCA1 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347380	qHTS for Antimalaria activity screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347388	qHTS for Activators of p53 Stress Response Pathway screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347356	HPAF-II 24hr Apoptosis Induction qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347359	HEK293 24hr Apoptosis Induction qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347374	qHTS for Hypoxia signaling pathway (HIF-1) antagonists against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347365	SDT Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347352	COV-362 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347368	G06 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347369	MCF7 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347362	Diaphorse counterscreen qHTS: Assay Interference Panel against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347373	qHTS for Constitutive Androstane Receptor (CAR) Agonist screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347389	qHTS assay for small molecule disruptors of mitochondrial membrane potential screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347371	J3T Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347361	HEK293 12hr Apoptosis Induction qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347379	qHTS for Inflammasome Signaling Inhibitors: IL-1-beta AlphaLISA screen against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347348	OV-SAHO Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347366	KB-3-1 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347393	qHTS for inhibitors of ER calcium dysfunction: SERCaMP assay screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347350	SW1088 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347347	UWB1.289 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347391	qHTS for activators of Nrf2/ARE signaling pathway screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347390	Secretion counterscreen for inhibitors of the SERCaMP assay screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347376	10-beta competent E. coli microbial cell viability qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347396	qHTS for inhibitors of Wild type Zika virus screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347400	Viability qHTS for inhibitors of the SERCaMP assay screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347360	HPAF-II 18hr Apoptosis Induction qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347372	qHTS for Constitutive Androstane Receptor (CAR) Antagonist screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347345	OV-KATE Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347349	Panc-1005 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347346	HPAF-II Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347392	qHTS for activators of dead-cell proteases activity screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347401	Redox Reaction Profiling qHTS: Assay Interference Panel against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347160	Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347353	A2780 Cisplatin Sensitive Ovarian Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347351	U-118MG Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347394	Vero-766 cells viability qHTS against the NCATS CANVASS Library: Counterscreen for Zika virus inhibition assay	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347364	KB-8-5-11 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347378	qHTS for H2AX Agonists against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347402	qHTS for inhibitors of Rabies Virus screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347387	Cytotoxicity qHTS for assessment of Hepg2 cells membrane integrity screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347358	HPAF-II 12hr Apoptosis Induction qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347355	HEK-293 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347370	qHTS for ATAD5 Antagonist screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347357	HEK293 18hr Apoptosis Induction qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347363	Firefly luciferase counterscreen qHTS: Assay Interference Panel against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347375	qHTS for Hypoxia signaling pathway (HIF-1) agonists against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347381	Inflammasome Signaling qHTS Counterscreen: IL-1-beta AlphaLISA counterscreen against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347367	qHTS for ATAD5 Agonist screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1803035	Enzyme Inhibition Assay from Article 10.3109/14756366.2011.578393: \\Carbonic anhydrase I and II inhibition with natural products: caffeine and piperine.\\	2012	Journal of enzyme inhibition and medicinal chemistry, Feb, Volume: 27, Issue:1	Carbonic anhydrase I and II inhibition with natural products: caffeine and piperine.
AID1296008	Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening	2020	SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1	Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986	P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987	P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159	Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1159607	Screen for inhibitors of RMI FANCM (MM2) intereaction	2016	Journal of biomolecular screening, Jul, Volume: 21, Issue:6	A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1159550	Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening	2015	Nature cell biology, Nov, Volume: 17, Issue:11	6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
AID540299	A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis	2010	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21	Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519	A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities	2011	Antiviral research, Sep, Volume: 91, Issue:3	High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID1347411	qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Mechanism Interrogation Plate v5.0 (MIPE) Libary	2020	ACS chemical biology, 07-17, Volume: 15, Issue:7	High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1346617	Human TRPV1 (Transient Receptor Potential channels)	2005	British journal of pharmacology, Mar, Volume: 144, Issue:6	Effects of piperine, the pungent component of black pepper, at the human vanilloid receptor (TRPV1).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	30 (3.35)	18.7374
1990's	53 (5.92)	18.2507
2000's	131 (14.64)	29.6817
2010's	429 (47.93)	24.3611
2020's	252 (28.16)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	39 (4.23%)	5.53%
Reviews	54 (5.85%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	830 (89.92%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (12)

Trial Overview

Trial	Phase	Enrollment	Study Type	Start Date	Status
Effect of Natural Agonists of TRPV1 in the Treatment of Functional Oropharyngeal Dysphagia in Neurological Diseases and the Elderly: Piperine [NCT01383694]	Phase 1/Phase 2	40 participants (Actual)	Interventional	2011-06-30	Completed
Effects of Curcumin Supplementation in Inflammation, Oxidative Stress and Intestinal Microbiota in Patients With Chronic Kidney Disease [NCT03475017]		30 participants (Actual)	Interventional	2018-02-22	Completed
A Phase 2, Double-blind, Randomized Study to Compare the Effect of Curcumin Versus Placebo on Inflammatory Cytokines, Symptoms and Disease Parameters in Clonal Cytopenia of Undetermined Significance (CCUS), Low-Risk Myelodysplastic Syndrome (LR-MDS), and [NCT06063486]	Phase 2	30 participants (Anticipated)	Interventional	2023-11-20	Not yet recruiting
A Randomized, Double-Blind Pilot Trial of Resveratrol With or Without Piperine to Enhance Plasma Levels of Resveratrol [NCT01324089]		24 participants (Actual)	Interventional	2011-03-31	Completed
Phase 1 Pilot Study of Curcumin and Piperine to Derive a Safe, Optimal Biologic Dose for Ureteral Stent-Induced Symptoms in Cancer Patients [NCT02598726]	Phase 1	9 participants (Actual)	Interventional	2016-03-01	Active, not recruiting
Biomechanical, Neurophysiological and Clinical Effects of 6-month Stimulation Using TRPV1 and TRPA1 Agonists in Older Patients With Oropharyngeal Dysphagia [NCT05958173]		150 participants (Anticipated)	Interventional	2023-09-01	Not yet recruiting
Evaluation of Curcumin Supplementation on p53 Levels and Apoptosis in Tumor Cells From Patients With Locally Advanced Cervical Cancer [NCT06080841]		30 participants (Anticipated)	Interventional	2023-04-19	Recruiting
Subacute Effect of Pharmacological Sensory Stimulation of the Oropharynx by Agonists of TRP Receptors in Swallowing Neurophysiology in the Elderly With Oropharyngeal Dysphagia. [NCT04741620]		150 participants (Actual)	Interventional	2019-01-17	Completed
Efficacy of Curcumin and Piperine in Patients on Active Surveillance for Either Monoclonal Gammopathy of Unknown Significance (MGUS), Low-risk Smoldering Multiple Myeloma (SMM) or Early Stage Prostate Cancer: A Pilot Study [NCT04731844]	Phase 2	40 participants (Anticipated)	Interventional	2021-12-14	Recruiting
Bioequivalence Assessment of Oral Administration Vs. Oral Spray of a Cannabinoid Combination (Δ9 -Tetrahydrocannabinol (THC) and Cannabidiol (CBD) In 1:1 Ratio) [NCT01893424]	Phase 1	12 participants (Actual)	Interventional	2013-08-31	Completed
Treatment of Acute Post-stroke Oropharyngeal Dysphagia With Paired Stimulation Through Peripheral TRVP1 Agonists and Non-invasive Brain Stimulation [NCT05735626]		60 participants (Anticipated)	Interventional	2021-07-01	Recruiting
The Combination of Vitamin D and Curcumin Piperine Attenuates the Disease Activity and Pro-Inflammatory Cytokines Levels in Systemic Lupus Erythematosus Patients [NCT05430087]	Phase 2	45 participants (Actual)	Interventional	2020-03-01	Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	8.03	4	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
5-hydroxytryptophan 5-Hydroxytryptophan: The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.. 5-hydroxytryptophan : A tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5.	2.06	1	0	hydroxytryptophan	human metabolite; neurotransmitter
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	7.97	4	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	2.03	1	0	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
quinacrine Quinacrine: An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years. It has also been used as an anthelmintic and in the treatment of giardiasis and malignant effusions. It is used in cell biological experiments as an inhibitor of phospholipase A2.. quinacrine : A member of the class of acridines that is acridine substituted by a chloro group at position 6, a methoxy group at position 2 and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9.	2.05	1	0	acridines; aromatic ether; organochlorine compound; tertiary amino compound	antimalarial; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	7.25	1	0	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
benzyl alcohol Benzyl Alcohol: A colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with LIDOCAINE injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutic aid, and in perfumery and flavoring.. hydroxytoluene : Any member of the class of toluenes carrying one or more hydroxy substituents.. benzyl alcohol : An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.. aromatic alcohol : Any alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.. aromatic primary alcohol : Any primary alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.	1.98	1	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
bis(4-nitrophenyl)phosphate bis(4-nitrophenyl)phosphate: RN given refers to parent cpd	2.06	1	0	aryl phosphate
carbamates [no description available]	2.41	1	0	amino-acid anion
aminooxyacetic acid Aminooxyacetic Acid: A compound that inhibits aminobutyrate aminotransferase activity in vivo, thereby raising the level of gamma-aminobutyric acid in tissues.. (aminooxy)acetic acid : A member of the class of hydroxylamines that is acetic acid substituted at postion 2 by an aminooxy group. It is a compound which inhibits aminobutyrate aminotransferase activity in vivo, resulting in increased levels of gamma-aminobutyric acid in tissues.	2.05	1	0	amino acid; hydroxylamines; monocarboxylic acid	anticonvulsant; EC 2.6.1.19 (4-aminobutyrate--2-oxoglutarate transaminase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; nootropic agent
carnitine [no description available]	4.43	2	2	amino-acid betaine	human metabolite; mouse metabolite
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	3.71	2	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
choline [no description available]	3.57	2	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	3.77	2	1	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.11	1	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	2.03	1	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
cuminaldehyde cuminaldehyde : A member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities.	2.31	1	0	benzaldehydes	insecticide; plant metabolite; volatile oil component
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	3.75	9	0	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
4-aminophenol 4-aminophenol: RN given refers to parent cpd. 4-aminophenol : An amino phenol (one of the three possible isomers) which has the single amino substituent located para to the phenolic -OH group.	2.07	1	0	aminophenol	allergen; metabolite
guaiacol Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.	4.48	5	1	guaiacols	disinfectant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; expectorant; plant metabolite
aminocaproic acid Aminocaproic Acid: An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties.. 6-aminohexanoic acid : An epsilon-amino acid comprising hexanoic acid carrying an amino substituent at position C-6. Used to control postoperative bleeding, and to treat overdose effects of the thrombolytic agents streptokinase and tissue plasminogen activator.	2.05	1	0	amino acid zwitterion; epsilon-amino acid; omega-amino fatty acid	antifibrinolytic drug; hematologic agent; metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.79	3	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	2.06	1	0	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	3.47	1	1	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
histamine [no description available]	3.14	5	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
indole [no description available]	2.25	1	0	indole; polycyclic heteroarene	Escherichia coli metabolite
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	2.52	2	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
thioctic acid Thioctic Acid: An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.	2.05	1	0	dithiolanes; heterocyclic fatty acid; thia fatty acid	fundamental metabolite; geroprotector
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	2.91	3	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
melatonin [no description available]	2.52	2	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
n-acetylserotonin N-acetylserotonin : An N-acylserotonin resulting from the formal condensation of the primary amino group of serotonin with the carboxy group of acetic acid.	2.17	1	0	acetamides; N-acylserotonin; phenols	antioxidant; human metabolite; mouse metabolite; tropomyosin-related kinase B receptor agonist
naringenin [no description available]	2.17	1	0	4'-hydroxyflavanones; trihydroxyflavanone
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.37	2	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitric acid Nitric Acid: Nitric acid (HNO3). A colorless liquid that is used in the manufacture of inorganic and organic nitrates and nitro compounds for fertilizers, dye intermediates, explosives, and many different organic chemicals. Continued exposure to vapor may cause chronic bronchitis; chemical pneumonitis may occur. (From Merck Index, 11th ed). nitric acid : A nitrogen oxoacid of formula HNO3 in which the nitrogen atom is bonded to a hydroxy group and by equivalent bonds to the remaining two oxygen atoms.	6.94	1	0	nitrogen oxoacid	protic solvent; reagent
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	3.23	5	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
phenethylamine phenethylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7016. 2-phenylethylamine : A phenylethylamine having the phenyl substituent at the 2-position.	2.17	1	0	alkaloid; aralkylamine; phenylethylamine	Escherichia coli metabolite; human metabolite; mouse metabolite
pyrazinamide pyrazinecarboxamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of pyrazinoic acid (pyrazine-2-carboxylic acid) with ammonia. A prodrug for pyrazinoic acid, pyrazinecarboxamide is used as part of multidrug regimens for the treatment of tuberculosis.	2.52	2	0	monocarboxylic acid amide; N-acylammonia; pyrazines	antitubercular agent; prodrug
quinolinic acid Quinolinic Acid: A metabolite of tryptophan with a possible role in neurodegenerative disorders. Elevated CSF levels of quinolinic acid are correlated with the severity of neuropsychological deficits in patients who have AIDS.. pyridinedicarboxylic acid : Any member of the class of pyridines carrying two carboxy groups.. quinolinic acid : A pyridinedicarboxylic acid that is pyridine substituted by carboxy groups at positions 2 and 3. It is a metabolite of tryptophan.	7.13	1	0	pyridinedicarboxylic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; NMDA receptor agonist
tryptamine [no description available]	2.17	1	0	aminoalkylindole; aralkylamino compound; indole alkaloid; tryptamines	human metabolite; mouse metabolite; plant metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	2.06	1	0	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	7.78	3	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
epibatidine [no description available]	2.07	1	0	alkaloid
8-hydroxy-2-(di-n-propylamino)tetralin 8-Hydroxy-2-(di-n-propylamino)tetralin: A serotonin 1A-receptor agonist that is used experimentally to test the effects of serotonin.. 8-OH-DPAT : A tetralin substituted at positions 1 and 7 by hydroxy and dipropylamino groups respectively	2.06	1	0	phenols; tertiary amino compound; tetralins	serotonergic antagonist
ibotenic acid Ibotenic Acid: A neurotoxic isoxazole (similar to KAINIC ACID and MUSCIMOL) found in AMANITA mushrooms. It causes motor depression, ataxia, and changes in mood, perceptions and feelings, and is a potent excitatory amino acid agonist.	7.25	1	0	non-proteinogenic alpha-amino acid	neurotoxin
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	5.31	3	0	p-menthane monoterpenoid; secondary alcohol	volatile oil component
5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate [no description available]	2.17	1	0	catechin
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	3	1	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine: A dopaminergic neurotoxic compound which produces irreversible clinical, chemical, and pathological alterations that mimic those found in Parkinson disease.. 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine : A tetrahydropyridine that is 1,2,3,6-tetrahydropyridine substituted by a methyl group at position 1 and a phenyl group at position 4.	7.11	1	0	methylpyridines; phenylpyridine; tetrahydropyridine	neurotoxin
2,4-dinitrophenol 2,4-Dinitrophenol: A toxic dye, chemically related to trinitrophenol (picric acid), used in biochemical studies of oxidative processes where it uncouples oxidative phosphorylation. It is also used as a metabolic stimulant. (Stedman, 26th ed). dinitrophenol : Members of the class of nitrophenol carrying two nitro substituents.. 2,4-dinitrophenol : A dinitrophenol having the nitro groups at the 2- and 4-positions.	1.97	1	0	dinitrophenol	allergen; antiseptic drug; bacterial xenobiotic metabolite; geroprotector; oxidative phosphorylation inhibitor
2-aminoethoxydiphenyl borate 2-aminoethoxydiphenyl borate: is a novel membrane-penetrable modulator and transient receptor potential channel blocker; structure in first source; do not confuse with 2-APB cpd. 2-aminoethoxydiphenylborane : An organoboron compound that is diphenylborane in which the borane hydrogen is replaced by a 2-aminoethoxy group.	3.12	1	0	organoboron compound; primary amino compound	calcium channel blocker; IP3 receptor antagonist; potassium channel opener
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	1.99	1	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
3-nitropropionic acid 3-nitropropionic acid: succinate dehydrogenase inactivator; biosynthesized by FABACEAE plants from ASPARAGINE. 3-nitropropanoic acid : A C-nitro compound that is propanoic acid in which one of the methyl hydrogens has been replaced by a nitro group.	2.11	1	0	C-nitro compound	antimycobacterial drug; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor; mycotoxin; neurotoxin
4-aminopyridine [no description available]	2.21	1	0	aminopyridine; aromatic amine	avicide; orphan drug; potassium channel blocker
phenytoin [no description available]	4.22	5	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
hydroxyindoleacetic acid (5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.	2.52	2	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
5-methoxytryptamine 5-Methoxytryptamine: Serotonin derivative proposed as potentiator for hypnotics and sedatives.. 5-methoxytryptamine : A member of the class of tryptamines that is the methyl ether derivative of serotonin.	2.17	1	0	aromatic ether; primary amino compound; tryptamines	5-hydroxytryptamine 2A receptor agonist; 5-hydroxytryptamine 2B receptor agonist; 5-hydroxytryptamine 2C receptor agonist; antioxidant; cardioprotective agent; human metabolite; mouse metabolite; neuroprotective agent; radiation protective agent; serotonergic agonist
7,8-dihydroxyflavone 7,8-dihydroxyflavone : A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A naturally occurring flavonoid produced by several plants, including the weed Tridax procumbens (coalbuttons or tridax daisy) and the tree Godmania aesculifolia, In animal models, it has shown efficacy against several diseases of the nervous system, including Alzheimer's, Parkinson's, and Huntington's.	2.17	1	0	dihydroxyflavone	antidepressant; antineoplastic agent; antioxidant; plant metabolite; tropomyosin-related kinase B receptor agonist
4',7-dihydroxyflavanone [no description available]	2.17	1	0	4'-hydroxyflavanones; dihydroxyflavanone; polyphenol	Brassica napus metabolite; fungal xenobiotic metabolite
7-nitroindazole 7-nitroindazole: an inhibitor of nitric oxide synthase; exhibits anti-nociceptive activity without increasing blood pressure	2.1	1	0
acebutolol Acebutolol: A cardioselective beta-1 adrenergic antagonist with little effect on the bronchial receptors. The drug has stabilizing and quinidine-like effects on cardiac rhythm, as well as weak inherent sympathomimetic action.. acebutolol : An ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol.	2.05	1	0	aromatic amide; ethanolamines; ether; monocarboxylic acid amide; propanolamine; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympathomimetic agent
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	5.92	8	1	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
acetazolamide Acetazolamide: One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)	2.47	2	0	monocarboxylic acid amide; sulfonamide; thiadiazoles	anticonvulsant; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
acetohydroxamic acid acetohydroxamic acid: urease inhibitor. oxime : Compounds of structure R2C=NOH derived from condensation of aldehydes or ketones with hydroxylamine. Oximes from aldehydes may be called aldoximes; those from ketones may be called ketoximes.. N-hydroxyacetimidic acid : A carbohydroximic acid consisting of acetimidic acid having a hydroxy group attached to the imide nitrogen.. acetohydroxamic acid : A member of the class of acetohydroxamic acids that is acetamide in which one of the amino hydrogens has been replaced by a hydroxy group.	2.05	1	0	acetohydroxamic acids; carbohydroximic acid	algal metabolite; EC 3.5.1.5 (urease) inhibitor
albendazole [no description available]	2.11	1	0	aryl sulfide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	anthelminthic drug; microtubule-destabilising agent; tubulin modulator
albuterol Albuterol: A short-acting beta-2 adrenergic agonist that is primarily used as a bronchodilator agent to treat ASTHMA. Albuterol is prepared as a racemic mixture of R(-) and S(+) stereoisomers. The stereospecific preparation of R(-) isomer of albuterol is referred to as levalbuterol.. albuterol : A member of the class of phenylethanolamines that is 4-(2-amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol having a tert-butyl group attached to the nirogen atom. It acts as a beta-adrenergic agonist used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).	2.05	1	0	phenols; phenylethanolamines; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; environmental contaminant; xenobiotic
alendronate alendronic acid : A 1,1-bis(phosphonic acid) that is methanebis(phosphonic acid) in which the two methylene hydrogens are replaced by hydroxy and 3-aminopropyl groups.	2.05	1	0	1,1-bis(phosphonic acid); primary amino compound	bone density conservation agent; EC 2.5.1.1 (dimethylallyltranstransferase) inhibitor
alprazolam Alprazolam: A triazolobenzodiazepine compound with antianxiety and sedative-hypnotic actions, that is efficacious in the treatment of PANIC DISORDERS, with or without AGORAPHOBIA, and in generalized ANXIETY DISORDERS. (From AMA Drug Evaluations Annual, 1994, p238). alprazolam : A member of the class of triazolobenzodiazepines that is 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine carrying methyl, phenyl and chloro substituents at positions 1, 6 and 8 respectively. Alprazolam is only found in individuals that have taken this drug.	2.05	1	0	organochlorine compound; triazolobenzodiazepine	anticonvulsant; anxiolytic drug; GABA agonist; muscle relaxant; sedative; xenobiotic
aminoglutethimide Aminoglutethimide: An aromatase inhibitor that is used in the treatment of advanced BREAST CANCER.. aminoglutethimide : A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.	2.05	1	0	dicarboximide; piperidones; substituted aniline	adrenergic agent; anticonvulsant; antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
pimagedine pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.	2.1	1	0	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor
theophylline [no description available]	9.08	4	0	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent
amiodarone Amiodarone: An antianginal and class III antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting POTASSIUM CHANNELS and VOLTAGE-GATED SODIUM CHANNELS. There is a resulting decrease in heart rate and in vascular resistance.. amiodarone : A member of the class of 1-benzofurans that is 1-benzofuran substituted by a butyl group at position 2 and a 4-[2-(diethylamino)ethoxy]-3,5-diiodobenzoyl group at position 3. It is a cardiovascular drug used for the treatment of cardiac dysrhythmias.	2.05	1	0	1-benzofurans; aromatic ketone; organoiodine compound; tertiary amino compound	cardiovascular drug
amitriptyline Amitriptyline: Tricyclic antidepressant with anticholinergic and sedative properties. It appears to prevent the re-uptake of norepinephrine and serotonin at nerve terminals, thus potentiating the action of these neurotransmitters. Amitriptyline also appears to antagonize cholinergic and alpha-1 adrenergic responses to bioactive amines.. amitriptyline : An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(dimethylamino)propylidene group at position 5.	2.05	1	0	carbotricyclic compound; tertiary amine	adrenergic uptake inhibitor; antidepressant; environmental contaminant; tropomyosin-related kinase B receptor agonist; xenobiotic
amlodipine Amlodipine: A long-acting dihydropyridine calcium channel blocker. It is effective in the treatment of ANGINA PECTORIS and HYPERTENSION.. amlodipine : A fully substituted dialkyl 1,4-dihydropyridine-3,5-dicarboxylate derivative, which is used for the treatment of hypertension, chronic stable angina and confirmed or suspected vasospastic angina.	2.05	1	0	dihydropyridine; ethyl ester; methyl ester; monochlorobenzenes; primary amino compound	antihypertensive agent; calcium channel blocker; vasodilator agent
anastrozole [no description available]	7.59	2	0	nitrile; triazoles	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
aprindine Aprindine: A class Ib anti-arrhythmia agent used to manage ventricular and supraventricular arrhythmias.	2.05	1	0	indanes
aristolochic acid i aristolochic acid I: phospholipase A inhibitor. aristolochic acid A : An aristolochic acid that is phenanthrene-1-carboxylic acid that is substituted by a methylenedioxy group at the 3,4 positions, by a methoxy group at position 8, and by a nitro group at position 10. It is the most abundant of the aristolochic acids and is found in almost all Aristolochia (birthworts or pipevines) species. It has been tried in a number of treatments for inflammatory disorders, mainly in Chinese and folk medicine. However, there is concern over their use as aristolochic acid is both carcinogenic and nephrotoxic.	2.07	1	0	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	2.75	3	0	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
atenolol Atenolol: A cardioselective beta-1 adrenergic blocker possessing properties and potency similar to PROPRANOLOL, but without a negative inotropic effect.. atenolol : An ethanolamine compound having a (4-carbamoylmethylphenoxy)methyl group at the 1-position and an N-isopropyl substituent.	2.05	1	0	ethanolamines; monocarboxylic acid amide; propanolamine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; sympatholytic agent; xenobiotic
aurintricarboxylic acid Aurintricarboxylic Acid: A dye which inhibits protein biosynthesis at the initial stages. The ammonium salt (aluminon) is a reagent for the colorimetric estimation of aluminum in water, foods, and tissues.. aurintricarboxylic acid : A member of the class of quinomethanes that is 3-methylidene-6-oxocyclohexa-1,4-diene-1-carboxylic acid in which the methylidene hydrogens are replaced by 4-carboxy-3-hydroxyphenyl groups. The trisodium salt is the biological stain 'chrome violet CG' while the triammonium salt is 'aluminon'.	1.99	1	0	monohydroxybenzoic acid; quinomethanes; tricarboxylic acid	fluorochrome; histological dye; insulin-like growth factor receptor 1 antagonist
azathioprine Azathioprine: An immunosuppressive agent used in combination with cyclophosphamide and hydroxychloroquine in the treatment of rheumatoid arthritis. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance has been listed as a known carcinogen. (Merck Index, 11th ed). azathioprine : A thiopurine that is 6-mercaptopurine in which the mercapto hydrogen is replaced by a 1-methyl-4-nitroimidazol-5-yl group. It is a prodrug for mercaptopurine and is used as an immunosuppressant, prescribed for the treatment of inflammatory conditions and after organ transplantation and also for treatment of Crohn's didease and MS.	2.05	1	0	aryl sulfide; C-nitro compound; imidazoles; thiopurine	antimetabolite; antineoplastic agent; carcinogenic agent; DNA synthesis inhibitor; hepatotoxic agent; immunosuppressive agent; prodrug
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	3.97	13	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
bepridil Bepridil: A long-acting calcium-blocking agent with significant anti-anginal activity. The drug produces significant coronary vasodilation and modest peripheral effects. It has antihypertensive and selective anti-arrhythmia activities and acts as a calmodulin antagonist.. bepridil : A tertiary amine in which the substituents on nitrogen are benzyl, phenyl and 3-(2-methylpropoxy)-2-(pyrrolidin-1-yl)propyl.	2.05	1	0	pyrrolidines; tertiary amine	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
berberine [no description available]	7.93	3	0	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
5-methoxypsoralen 5-Methoxypsoralen: A linear furanocoumarin that has phototoxic and anti-inflammatory properties, with effects similar to METHOXSALEN. It is used in PUVA THERAPY for the treatment of PSORIASIS.. 5-methoxypsoralen : A 5-methoxyfurocoumarin that is psoralen substituted by a methoxy group at position 5.	2.52	2	0	5-methoxyfurocoumarin; organic heterotricyclic compound; psoralens	hepatoprotective agent; plant metabolite
bisoprolol Bisoprolol: A cardioselective beta-1 adrenergic blocker. It is effective in the management of HYPERTENSION and ANGINA PECTORIS.	2.05	1	0	secondary alcohol; secondary amine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
bretylium bretylium: RN given refers to parent cpd. bretylium : A quaternary ammonium cation having 2-bromobenzyl, ethyl and two methyl groups attached to the nitrogen. It blocks noradrenaline release from the peripheral sympathetic nervous system, and is used in emergency medicine, cardiology, and other specialties for the acute management of ventricular tachycardia and ventricular fibrillation.	2.05	1	0	quaternary ammonium ion	adrenergic antagonist; anti-arrhythmia drug; antihypertensive agent
bromhexine Bromhexine: A mucolytic agent used in the treatment of respiratory disorders associated with viscid or excessive mucus. (From Martindale, The Extra Pharmacopoeia, 30th ed, p744). bromhexine : A substituted aniline that is 2,4-dibromoaniline which is substituted at position 6 by a [cyclohexyl(methyl)amino]methyl group. It is used (as the monohydrochloride salt) as a mucolytic for the treatment of respiratory disorders associated with productive cough (i.e. a cough characterised by the production of sputum).	2.05	1	0	organobromine compound; substituted aniline; tertiary amino compound	mucolytic
bumetanide [no description available]	2.41	2	0	amino acid; benzoic acids; sulfonamide	diuretic; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor
caffeine [no description available]	7.53	2	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	4.9	10	0	aromatic ether; nitrile; polyether; tertiary amino compound
carbamazepine Carbamazepine: A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.. carbamazepine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.	5	8	1	dibenzoazepine; ureas	analgesic; anticonvulsant; antimanic drug; drug allergen; EC 3.5.1.98 (histone deacetylase) inhibitor; environmental contaminant; glutamate transporter activator; mitogen; non-narcotic analgesic; sodium channel blocker; xenobiotic
carmustine Carmustine: A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed). carmustine : A member of the class of N-nitrosoureas that is 1,3-bis(2-chloroethyl)urea in which one of the nitrogens is substituted by a nitroso group.	2.05	1	0	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent
carteolol Carteolol: A beta-adrenergic antagonist used as an anti-arrhythmia agent, an anti-angina agent, an antihypertensive agent, and an antiglaucoma agent.	2.05	1	0	quinolone; secondary alcohol	anti-arrhythmia drug; antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
carbonyl cyanide m-chlorophenyl hydrazone Carbonyl Cyanide m-Chlorophenyl Hydrazone: A proton ionophore. It is commonly used as an uncoupling agent and inhibitor of photosynthesis because of its effects on mitochondrial and chloroplast membranes.. CCCP : A member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death.	2.17	1	0	hydrazone; monochlorobenzenes; nitrile	antibacterial agent; geroprotector; ionophore
celecoxib [no description available]	7.69	2	0	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
cetirizine Cetirizine: A potent second-generation histamine H1 antagonist that is effective in the treatment of allergic rhinitis, chronic urticaria, and pollen-induced asthma. Unlike many traditional antihistamines, it does not cause drowsiness or anticholinergic side effects.. cetirizine : A member of the class of piperazines that is piperazine in which the hydrogens attached to nitrogen are replaced by a (4-chlorophenyl)(phenyl)methyl and a 2-(carboxymethoxy)ethyl group respectively.	2.11	1	0	ether; monocarboxylic acid; monochlorobenzenes; piperazines	anti-allergic agent; environmental contaminant; H1-receptor antagonist; xenobiotic
cetyltrimethylammonium ion Cetrimonium: Cetyltrimethylammonium compound whose salts and derivatives are used primarily as topical antiseptics.. cetyltrimethylammonium ion : A quaternary ammonium ion in which the substituents on nitrogen are one hexadecyl and three methyl groups.	2.53	2	0	quaternary ammonium ion
chelerythrine chelerythrine : A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae.	2.11	1	0	benzophenanthridine alkaloid; organic cation	antibacterial agent; antineoplastic agent; EC 2.7.11.13 (protein kinase C) inhibitor
chlordiazepoxide Chlordiazepoxide: An anxiolytic benzodiazepine derivative with anticonvulsant, sedative, and amnesic properties. It has also been used in the symptomatic treatment of alcohol withdrawal.. chlordiazepoxide : A benzodiazepine that is 3H-1,4-benzodiazepine 4-oxide substituted by a chloro group at position 7, a phenyl group at position 5 and a methylamino group at position 2.	2.05	1	0	benzodiazepine
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	2.05	1	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	2.45	2	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
chlorpropamide Chlorpropamide: A sulfonylurea hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. (From Martindale, The Extra Pharmacopoeia, 30th ed, p277). chlorpropamide : An N-sulfonylurea that is urea in which a hydrogen attached to one of the nitrogens is substituted by 4-chlorobenzenesulfonyl group and a hydrogen attached to the other nitrogen is substituted by propyl group. Chlorpropamide is a hypoglycaemic agent used in the treatment of type 2 (non-insulin-dependent) diabetes mellitus not responding to dietary modification.	2.05	1	0	monochlorobenzenes; N-sulfonylurea	hypoglycemic agent; insulin secretagogue
chlorthalidone Chlorthalidone: A benzenesulfonamide-phthalimidine that tautomerizes to a BENZOPHENONES form. It is considered a thiazide-like diuretic.	2.05	1	0	isoindoles; monochlorobenzenes; sulfonamide
chlorzoxazone Chlorzoxazone: A centrally acting central muscle relaxant with sedative properties. It is claimed to inhibit muscle spasm by exerting an effect primarily at the level of the spinal cord and subcortical areas of the brain. (From Martindale, The Extra Pharmacopoea, 30th ed, p1202). chlorzoxazone : A member of the class of 1,3-benzoxazoles that is 1,3-benzoxazol-2-ol in which the hydrogen atom at position 5 is substituted by chlorine. A centrally acting muscle relaxant with sedative properties, it is used for the symptomatic treatment of painful muscle spasm.	2.11	1	0	1,3-benzoxazoles; heteroaryl hydroxy compound; organochlorine compound	muscle relaxant; sedative
cimetidine Cimetidine: A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.. cimetidine : A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach.	2.05	1	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
aricine [no description available]	2.04	1	0	cinchona alkaloid
eucalyptol [no description available]	3.12	1	0
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	8.43	7	0	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic
citalopram Citalopram: A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from TARDIVE DYSKINESIA in preference to tricyclic antidepressants, which aggravate dyskinesia.. citalopram : A racemate comprising equimolar amounts of (R)-citalopram and its enantiomer, escitalopram. It is used as an antidepressant, although only escitalopram is active.. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile : A nitrile that is 1,3-dihydro-2-benzofuran-5-carbonitrile in which one of the hydrogens at position 1 is replaced by a p-fluorophenyl group, while the other is replaced by a 3-(dimethylamino)propyl group.	2.05	1	0	2-benzofurans; cyclic ether; nitrile; organofluorine compound; tertiary amino compound
clenbuterol Clenbuterol: A substituted phenylaminoethanol that has beta-2 adrenomimetic properties at very low doses. It is used as a bronchodilator in asthma.. clenbuterol : A substituted aniline that is 2,6-dichloroaniline in which the hydrogen at position 4 has been replaced by a 2-(tert-butylamino)-1-hydroxyethyl group.	2.05	1	0	amino alcohol; dichlorobenzene; ethanolamines; primary arylamine; secondary amino compound; substituted aniline	beta-adrenergic agonist; bronchodilator agent; sympathomimetic agent
clioquinol Clioquinol: A potentially neurotoxic 8-hydroxyquinoline derivative long used as a topical anti-infective, intestinal antiamebic, and vaginal trichomonacide. The oral preparation has been shown to cause subacute myelo-optic neuropathy and has been banned worldwide.. 5-chloro-7-iodoquinolin-8-ol : A monohydroxyquinoline that is quinolin-8-ol in which the hydrogens at positions 5 and 7 are replaced by chlorine and iodine, respectively. It has antibacterial and atifungal properties, and is used in creams for the treatment of skin infections. It has also been investigated as a chelator of copper and zinc ions for the possible treatment of Alzheimer's disease.	2.05	1	0	monohydroxyquinoline; organochlorine compound; organoiodine compound	antibacterial agent; antifungal agent; antimicrobial agent; antineoplastic agent; antiprotozoal drug; chelator; copper chelator
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	2.05	1	0	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist
clomipramine Clomipramine: A tricyclic antidepressant similar to IMIPRAMINE that selectively inhibits the uptake of serotonin in the brain. It is readily absorbed from the gastrointestinal tract and demethylated in the liver to form its primary active metabolite, desmethylclomipramine.. clomipramine : A dibenzoazepine that is 10,11-dihydro-5H-dibenzo[b,f]azepine which is substituted by chlorine at position 3 and in which the hydrogen attached to the nitrogen is replaced by a 3-(dimethylamino)propyl group. One of the more sedating tricyclic antidepressants, it is used as the hydrochloride salt for the treatment of depression as well as obsessive-compulsive disorder and phobias.	2.45	2	0	dibenzoazepine	anticoronaviral agent; antidepressant; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; serotonergic antagonist; serotonergic drug; serotonin uptake inhibitor
clonidine Clonidine: An imidazoline sympatholytic agent that stimulates ALPHA-2 ADRENERGIC RECEPTORS and central IMIDAZOLINE RECEPTORS. It is commonly used in the management of HYPERTENSION.. clonidine (amino form) : A clonidine that is 4,5-dihydro-1H-imidazol-2-amine in which one of the amino hydrogens is replaced by a 2,6-dichlorophenyl group.	2.05	1	0	clonidine; imidazoline
chlorazepate clorazepic acid : A 1,4-benzodiazepinone in which the oxo group is at position 2, and which is substituted at positions 3, 5, and 7 by carboxy, phenyl and chloro groups, respectively.	2.05	1	0	1,4-benzodiazepinone	anticonvulsant; anxiolytic drug; GABA modulator; prodrug
clotrimazole [no description available]	2.11	1	0	conazole antifungal drug; imidazole antifungal drug; imidazoles; monochlorobenzenes	antiinfective agent; environmental contaminant; xenobiotic
cypermethrin cypermethrin : A carboxylic ester resulting from the formal condensation between 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid and the alcoholic hydroxy group of hydroxy(3-phenoxyphenyl)acetonitrile.. zeta-cypermethrin : A diastereoisomeric mixture comprising the isomeric pair (1R)-cis-(alphaS)- and (1S)-trans-(alphaR)-cypermethrin together with the isomeric pair (1S)-cis-(alphaS)- and (1S)-trans-(alphaS)-cypermethrin where the ratio between the isomeric pairs lies in the range 45:55 to 55:45.	7.6	1	0	aromatic ether; cyclopropanecarboxylate ester; nitrile; organochlorine compound	agrochemical; molluscicide; pyrethroid ester acaricide; pyrethroid ester insecticide
dapsone [no description available]	2.05	1	0	substituted aniline; sulfone	anti-inflammatory drug; antiinfective agent; antimalarial; leprostatic drug
debrisoquin Debrisoquin: An adrenergic neuron-blocking drug similar in effects to GUANETHIDINE. It is also noteworthy in being a substrate for a polymorphic cytochrome P-450 enzyme. Persons with certain isoforms of this enzyme are unable to properly metabolize this and many other clinically important drugs. They are commonly referred to as having a debrisoquin 4-hydroxylase polymorphism.	2.05	1	0	carboxamidine; isoquinolines	adrenergic agent; antihypertensive agent; human metabolite; sympatholytic agent
2,3-dimethoxy-5-methyl-6-decyl-1,4-benzoquinone 2,3-dimethoxy-5-methyl-6-decyl-1,4-benzoquinone: ubiquinol analog. 6-decylubiquinone : A member of the class of 1,4-benzoquinones that is 2,3-dimethoxybenzoquinone which has been substituted at positions 5 and 6 by decyl and methyl groups.	2.07	1	0	1,4-benzoquinones	cofactor
desipramine Desipramine: A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.. desipramine : A dibenzoazepine consisting of 10,11-dihydro-5H-dibenzo[b,f]azepine substituted on nitrogen with a 3-(methylamino)propyl group.	2.05	1	0	dibenzoazepine; secondary amino compound	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; cholinergic antagonist; drug allergen; EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; serotonin uptake inhibitor
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	4.31	5	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
diazoxide Diazoxide: A benzothiadiazine derivative that is a peripheral vasodilator used for hypertensive emergencies. It lacks diuretic effect, apparently because it lacks a sulfonamide group.. diazoxide : A benzothiadiazine that is the S,S-dioxide of 2H-1,2,4-benzothiadiazine which is substituted at position 3 by a methyl group and at position 7 by chlorine. A peripheral vasodilator, it increases the concentration of glucose in the plasma and inhibits the secretion of insulin by the beta- cells of the pancreas. It is used orally in the management of intractable hypoglycaemia and intravenously in the management of hypertensive emergencies.	2.05	1	0	benzothiadiazine; organochlorine compound; sulfone	antihypertensive agent; beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; diuretic; K-ATP channel agonist; sodium channel blocker; sympathomimetic agent; vasodilator agent
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	2.05	1	0	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
3,4-dihydroxybenzohydroxamic acid [no description available]	2.05	1	0	benzoic acids
diflunisal Diflunisal: A salicylate derivative and anti-inflammatory analgesic with actions and side effects similar to those of ASPIRIN.. diflunisal : An organofluorine compound comprising salicylic acid having a 2,4-difluorophenyl group at the 5-position.	2.05	1	0	monohydroxybenzoic acid; organofluorine compound	non-narcotic analgesic; non-steroidal anti-inflammatory drug
3,3'-diindolylmethane 3,3'-diindolylmethane: anti-inflammatory from edible cruciferous vegetables; a cytochrome P-450 antagonist	2.07	1	0	indoles	antineoplastic agent; P450 inhibitor
dilazep Dilazep: Coronary vasodilator with some antiarrhythmic activity.. dilazep : A member of the class of diazepanes that is 1,4-diazepane substituted by 3-[(3,4,5-trimethoxybenzoyl)oxy]propyl groups at positions 1 and 4. It is a potent adenosine uptake inhibitor that exhibits antiplatelet, antianginal and vasodilator properties.	1.98	1	0	benzoate ester; diazepane; diester; methoxybenzenes	cardioprotective agent; platelet aggregation inhibitor; vasodilator agent
dimercaprol Dimercaprol: An anti-gas warfare agent that is effective against Lewisite (dichloro(2-chlorovinyl)arsine) and formerly known as British Anti-Lewisite or BAL. It acts as a chelating agent and is used in the treatment of arsenic, gold, and other heavy metal poisoning.. dimercaprol : A dithiol that is propane-1,2-dithiol in which one of the methyl hydrogens is replaced by a hydroxy group. a chelating agent originally developed during World War II as an experimental antidote against the arsenic-based poison gas Lewisite, it has been used clinically since 1949 for the treatment of poisoning by arsenic, mercury and gold. It can also be used for treatment of poisoning by antimony, bismuth and possibly thallium, and (with sodium calcium edetate) in cases of acute leaad poisoning. Administration is by (painful) intramuscular injection of a suspension of dimercaprol in peanut oil, typically every 4 hours for 2-10 days depending on the toxicity. In the past, dimercaprol was also used for the treatment of Wilson's disease, a severely debilitating genetic disorder in which the body tends to retain copper, with resultant liver and brain injury.	2.05	1	0	dithiol; primary alcohol	chelator
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	2.1	1	0	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent
domperidone Domperidone: A specific blocker of dopamine receptors. It speeds gastrointestinal peristalsis, causes prolactin release, and is used as antiemetic and tool in the study of dopaminergic mechanisms.. domperidone : 1-[3-(Piperidin-1-yl)propyl]-1,3-dihydro-2H-benzimidazol-2-one in which the 4-position of the piperidine ring is substituted by a 5-chloro-1,3-dihydro-2H-benzimidazol-2-on-1-yl group. A dopamine antagonist, it is used as an antiemetic for the short-term treatment of nausea and vomiting, and to control gastrointestinal effects of dopaminergic drugs given in the management of parkinsonism. The free base is used in oral suspensions, while the maleate salt is used in tablet preparations.	3.04	4	0	benzimidazoles; heteroarylpiperidine	antiemetic; dopaminergic antagonist
donepezil Donepezil: An indan and piperidine derivative that acts as a selective and reversible inhibitor of ACETYLCHOLINESTERASE. Donepezil is highly selective for the central nervous system and is used in the management of mild to moderate DEMENTIA in ALZHEIMER DISEASE.. donepezil : A racemate comprising equimolar amounts of (R)- and (S)-donepezil. A centrally acting reversible acetylcholinesterase inhibitor, its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine.. 2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxyindan-1-one : A member of the class of indanones that is 5,6-dimethoxyindan-1-one which is substituted at position 2 by an (N-benzylpiperidin-4-yl)methyl group.	7.52	2	0	aromatic ether; indanones; piperidines; racemate	EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; nootropic agent
ellipticine ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.	2.07	1	0	indole alkaloid; organic heterotetracyclic compound; organonitrogen heterocyclic compound; polycyclic heteroarene	antineoplastic agent; plant metabolite
embelin embelin: from Embelia fruit (Myrsinaceae). embelin : A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, antineoplastic and inhibitory activity towards hepatitis C protease.	2.49	2	0	dihydroxy-1,4-benzoquinones	antimicrobial agent; antineoplastic agent; hepatitis C protease inhibitor; plant metabolite
emodin Emodin: Purgative anthraquinone found in several plants, especially RHAMNUS PURSHIANA. It was formerly used as a laxative, but is now used mainly as a tool in toxicity studies.. emodin : A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs.	7.82	3	0	trihydroxyanthraquinone	antineoplastic agent; laxative; plant metabolite; tyrosine kinase inhibitor
erythrosine Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.	2.17	1	0
ethacrynic acid Ethacrynic Acid: A compound that inhibits symport of sodium, potassium, and chloride primarily in the ascending limb of Henle, but also in the proximal and distal tubules. This pharmacological action results in excretion of these ions, increased urinary output, and reduction in extracellular fluid. This compound has been classified as a loop or high ceiling diuretic.. etacrynic acid : An aromatic ether that is phenoxyacetic acid in which the phenyl ring is substituted by chlorines at positions 2 and 3, and by a 2-methylidenebutanoyl group at position 4. It is a loop diuretic used to treat high blood pressure resulting from diseases such as congestive heart failure, liver failure, and kidney failure. It is also a glutathione S-transferase (EC 2.5.1.18) inhibitor.	2.05	1	0	aromatic ether; aromatic ketone; dichlorobenzene; monocarboxylic acid	EC 2.5.1.18 (glutathione transferase) inhibitor; ion transport inhibitor; loop diuretic
ethosuximide Ethosuximide: An anticonvulsant especially useful in the treatment of absence seizures unaccompanied by other types of seizures.. ethosuximide : A dicarboximide that is pyrrolidine-2,5-dione in which the hydrogens at position 3 are substituted by one methyl and one ethyl group. An antiepileptic, it is used in the treatment of absence seizures and may be used for myoclonic seizures, but is ineffective against tonic-clonic seizures.	2.05	1	0	dicarboximide; pyrrolidinone	anticonvulsant; geroprotector; T-type calcium channel blocker
ethyl loflazepate ethyl loflazepate: structure given in first source	2.05	1	0	organic molecular entity
felodipine Felodipine: A dihydropyridine calcium antagonist with positive inotropic effects. It lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels.. felodipine : The mixed (methyl, ethyl) diester of 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid. A calcium-channel blocker, it lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels. It is used in the management of hypertension and angina pectoris.	2.05	1	0	dichlorobenzene; dihydropyridine; ethyl ester; methyl ester	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
berotek Fenoterol: A synthetic adrenergic beta-2 agonist that is used as a bronchodilator and tocolytic.. fenoterol : A member of the class resorcinols that is 5-(1-hydroxyethyl)benzene-1,3-diol in which one of the methyl hydrogens is replaced by a 1-(4-hydroxyphenyl)propan-2-amino group. A beta2-adrenergic agonist, it is used (as the hydrobromide salt) as a bronchodilator in the management of reversible airway obstruction.	2.05	1	0	resorcinols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; sympathomimetic agent; tocolytic agent
fentanyl Fentanyl: A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078). fentanyl : A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.	2.05	1	0	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
fexofenadine fexofenadine: a second generation antihistamine; metabolite of the antihistaminic drug terfenadine; structure in first source; RN refers to HCl. fexofenadine : A piperidine-based anti-histamine compound.	2.49	2	0	piperidines; tertiary amine	anti-allergic agent; H1-receptor antagonist
flecainide Flecainide: A potent anti-arrhythmia agent, effective in a wide range of ventricular and atrial ARRHYTHMIAS and TACHYCARDIAS.. flecainide : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid with the primary amino group of piperidin-2-ylmethylamine. An antiarrhythmic agent used (in the form of its acetate salt) to prevent and treat tachyarrhythmia (abnormal fast rhythm of the heart).	2.05	1	0	aromatic ether; monocarboxylic acid amide; organofluorine compound; piperidines	anti-arrhythmia drug
fluconazole Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.	2.58	2	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
fluphenazine [no description available]	2.05	1	0	N-alkylpiperazine; organofluorine compound; phenothiazines	anticoronaviral agent; dopaminergic antagonist; phenothiazine antipsychotic drug
flumazenil Flumazenil: A potent benzodiazepine receptor antagonist. Since it reverses the sedative and other actions of benzodiazepines, it has been suggested as an antidote to benzodiazepine overdoses.. flumazenil : An organic heterotricyclic compound that is 5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted at positions 3, 5, 6, and 8 by ethoxycarbonyl, methyl, oxo, and fluoro groups, respectively. It is used as an antidote to benzodiazepine overdose.	2.47	2	0	ethyl ester; imidazobenzodiazepine; organofluorine compound	antidote to benzodiazepine poisoning; GABA antagonist
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	2.04	1	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
fluoxetine Fluoxetine: The first highly specific serotonin uptake inhibitor. It is used as an antidepressant and often has a more acceptable side-effects profile than traditional antidepressants.. fluoxetine : A racemate comprising equimolar amounts of (R)- and (S)-fluoxetine. A selective serotonin reuptake inhibitor (SSRI), it is used (generally as the hydrochloride salt) for the treatment of depression (and the depressive phase of bipolar disorder), bullimia nervosa, and obsessive-compulsive disorder.. N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine : An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group.	2.75	3	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
flurbiprofen Flurbiprofen: An anti-inflammatory analgesic and antipyretic of the phenylalkynoic acid series. It has been shown to reduce bone resorption in periodontal disease by inhibiting CARBONIC ANHYDRASE.. flurbiprofen : A monocarboxylic acid that is a 2-fluoro-[1,1'-biphenyl-4-yl] moiety linked to C-2 of propionic acid. A non-steroidal anti-inflammatory, analgesic and antipyretic, it is used as a pre-operative anti-miotic as well as orally for arthritis or dental pain.	9.78	2	1	fluorobiphenyl; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
flutamide Flutamide: An antiandrogen with about the same potency as cyproterone in rodent and canine species.	2.05	1	0	(trifluoromethyl)benzenes; monocarboxylic acid amide	androgen antagonist; antineoplastic agent
furosemide Furosemide: A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.. furosemide : A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.	2.41	2	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	7.11	1	0
glimepiride glimepiride: structure given in first source	7.07	1	0	sulfonamide
glutethimide Glutethimide: A hypnotic and sedative. Its use has been largely superseded by other drugs.	2.05	1	0	piperidines
gossypol Gossypol: A dimeric sesquiterpene found in cottonseed (GOSSYPIUM). The (-) isomer is active as a male contraceptive (CONTRACEPTIVE AGENTS, MALE) whereas toxic symptoms are associated with the (+) isomer.	2.07	1	0
guanethidine Guanethidine: An antihypertensive agent that acts by inhibiting selectively transmission in post-ganglionic adrenergic nerves. It is believed to act mainly by preventing the release of norepinephrine at nerve endings and causes depletion of norepinephrine in peripheral sympathetic nerve terminals as well as in tissues.. guanethidine : A member of the class of guanidines in which one of the hydrogens of the amino group has been replaced by a 2-azocan-1-ylethyl group.. guanethidine sulfate : A organic sulfate salt composed of two molecules of guanethidine and one of sulfuric acid.	2.05	1	0	azocanes; guanidines	adrenergic antagonist; antihypertensive agent; sympatholytic agent
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	7.06	1	0	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
harmaline Harmaline: A beta-carboline alkaloid isolated from seeds of PEGANUM.. harmaline : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7 and has been reduced across the 3,4 bond.	2.49	2	0	harmala alkaloid	oneirogen
miltefosine miltefosine: hexadecyl phosphocholine derivative of cisplatin; did not substantially activate HIV long terminal repeat; less toxic than cisplatin. miltefosine : A phospholipid that is the hexadecyl monoester of phosphocholine.	2.05	1	0	phosphocholines; phospholipid	anti-inflammatory agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antiprotozoal drug; apoptosis inducer; immunomodulator; protein kinase inhibitor
hexamethonium Hexamethonium: A nicotinic cholinergic antagonist often referred to as the prototypical ganglionic blocker. It is poorly absorbed from the gastrointestinal tract and does not cross the blood-brain barrier. It has been used for a variety of therapeutic purposes including hypertension but, like the other ganglionic blockers, it has been replaced by more specific drugs for most purposes, although it is widely used a research tool.	2	1	0	quaternary ammonium salt
hexobarbital Hexobarbital: A barbiturate that is effective as a hypnotic and sedative.. hexobarbital : A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups.	1.96	1	0	barbiturates
ethidium Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.	8.32	6	0	phenanthridines	fluorochrome; intercalator
hydrochlorothiazide Hydrochlorothiazide: A thiazide diuretic often considered the prototypical member of this class. It reduces the reabsorption of electrolytes from the renal tubules. This results in increased excretion of water and electrolytes, including sodium, potassium, chloride, and magnesium. It is used in the treatment of several disorders including edema, hypertension, diabetes insipidus, and hypoparathyroidism.. hydrochlorothiazide : A benzothiadiazine that is 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide substituted by a chloro group at position 6 and a sulfonamide at 7. It is diuretic used for the treatment of hypertension and congestive heart failure.	2.05	1	0	benzothiadiazine; organochlorine compound; sulfonamide	antihypertensive agent; diuretic; environmental contaminant; xenobiotic
hydroxyurea [no description available]	2.05	1	0	one-carbon compound; ureas	antimetabolite; antimitotic; antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; genotoxin; immunomodulator; radical scavenger; teratogenic agent
hydroxyzine Hydroxyzine: A histamine H1 receptor antagonist that is effective in the treatment of chronic urticaria, dermatitis, and histamine-mediated pruritus. Unlike its major metabolite CETIRIZINE, it does cause drowsiness. It is also effective as an antiemetic, for relief of anxiety and tension, and as a sedative.. hydroxyzine : A N-alkylpiperazine that is piperzine in which the nitrogens atoms are substituted by 2-(2-hydroxyethoxy)ethyl and (4-chlorophenyl)(phenyl)methyl groups respectively.	2.05	1	0	hydroxyether; monochlorobenzenes; N-alkylpiperazine	anticoronaviral agent; antipruritic drug; anxiolytic drug; dermatologic drug; H1-receptor antagonist
hypericin [no description available]	2.07	1	0
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	7.77	3	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
phenelzine Phenelzine: One of the MONOAMINE OXIDASE INHIBITORS used to treat DEPRESSION; PHOBIC DISORDERS; and PANIC.	2.05	1	0	primary amine
lidocaine Lidocaine: A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of PROCAINE but its duration of action is shorter than that of BUPIVACAINE or PRILOCAINE.. lidocaine : The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.	2.05	1	0	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic
idebenone [no description available]	2.21	1	0	1,4-benzoquinones; primary alcohol	antioxidant; ferroptosis inhibitor
imipramine Imipramine: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.. imipramine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.	2.05	1	0	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
amrinone Amrinone: A positive inotropic cardiotonic (CARDIOTONIC AGENTS) with vasodilator properties, phosphodiesterase 3 inhibitory activity, and the ability to stimulate calcium ion influx into the cardiac cell.. amrinone : A 3,4'-bipyridine substituted at positions 5 and 6 by an amino group and a keto function respectively. A pyridine phosphodiesterase 3 inhibitor, it is a drug that may improve the prognosis in patients with congestive heart failure.	2.05	1	0	bipyridines	EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
incadronate [no description available]	2.05	1	0	1,1-bis(phosphonic acid)
indapamide Indapamide: A benzamide-sulfonamide-indole derived DIURETIC that functions by inhibiting SODIUM CHLORIDE SYMPORTERS.. indapamide : A sulfonamide formed by condensation of the carboxylic group of 4-chloro-3-sulfamoylbenzoic acid with the amino group of 2-methyl-2,3-dihydro-1H-indol-1-amine.	2.05	1	0	indoles; organochlorine compound; sulfonamide	antihypertensive agent; diuretic
indole-3-carbinol indole-3-carbinol: occurs in edible cruciferous vegetables. indole-3-methanol : An indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity.	3.59	2	0	indolyl alcohol	antineoplastic agent; plant metabolite
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	3.32	6	0	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
avapro Irbesartan: A spiro compound, biphenyl and tetrazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION, and in the treatment of kidney disease.. irbesartan : A biphenylyltetrazole that is an angiotensin II receptor antagonist used mainly for the treatment of hypertension.	2.41	1	0	azaspiro compound; biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
isoniazid Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).	9.57	5	1	carbohydrazide	antitubercular agent; drug allergen
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	2.98	4	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
staurosporine aglycone staurosporine aglycone: metabolite from culture broth of Nocardiopsis sp.; a neurotrophin antag; inhibits BDNF TrkB receptor	2.1	1	0
nsc 664704 kenpaullone: inhibits CDK1/cyclin B; structure in first source. kenpaullone : An indolobenzazepine that is paullone in which the hydrogen at position 9 is replaced by a bromo substituent. It is an ATP-competitive inhibitor of cyclin-dependent kinases (CDKs) and glycogen synthase kinase 3beta (GSK3beta).	2.47	2	0	indolobenzazepine; lactam; organobromine compound	cardioprotective agent; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor; EC 2.7.11.26 (tau-protein kinase) inhibitor; geroprotector
ketamine Ketamine: A cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE) and may interact with sigma receptors.. ketamine : A member of the class of cyclohexanones in which one of the hydrogens at position 2 is substituted by a 2-chlorophenyl group, while the other is substituted by a methylamino group.	2.05	1	0	cyclohexanones; monochlorobenzenes; secondary amino compound	analgesic; environmental contaminant; intravenous anaesthetic; neurotoxin; NMDA receptor antagonist; xenobiotic
ketanserin Ketanserin: A selective serotonin receptor antagonist with weak adrenergic receptor blocking properties. The drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation. It is well tolerated and is particularly effective in older patients.. ketanserin : A member of the class of quinazolines that is quinazoline-2,4(1H,3H)-dione which is substituted at position 3 by a 2-[4-(p-fluorobenzoyl)piperidin-1-yl]ethyl group.	2.05	1	0	aromatic ketone; organofluorine compound; piperidines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; cardiovascular drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
ketoconazole 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.	7.43	2	0	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
ketoprofen Ketoprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.. ketoprofen : An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2.	7.53	2	0	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
ketotifen Ketotifen: A cycloheptathiophene blocker of histamine H1 receptors and release of inflammatory mediators. It has been proposed for the treatment of asthma, rhinitis, skin allergies, and anaphylaxis.. ketotifen : An organic heterotricyclic compound that is 4,9-dihydro-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one which is substituted at position 4 by a 1-methylpiperidin-4-ylidene group. A blocker of histamine H1 receptors with a stabilising action on mast cells, it is used (usually as its hydrogen fumarate salt) for the treatment of asthma, where it may take several weeks to exert its full effect.	2.05	1	0	cyclic ketone; olefinic compound; organic heterotricyclic compound; organosulfur heterocyclic compound; piperidines; tertiary amino compound	anti-asthmatic drug; H1-receptor antagonist
khellin Khellin: A vasodilator that also has bronchodilatory action. It has been employed in the treatment of angina pectoris, in the treatment of asthma, and in conjunction with ultraviolet light A, has been tried in the treatment of vitiligo. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1024). khellin : A furanochrome in which the basic tricyclic skeleton is substituted at positions 4 and 9 with methoxy groups and at position 7 with a methyl group. A major constituent of the plant Ammi visnaga it is a herbal folk medicine used for various illnesses, its main effect being as a vasodilator.	2.8	3	0	furanochromone; organic heterotricyclic compound; oxacycle	anti-asthmatic agent; bronchodilator agent; cardiovascular drug; vasodilator agent
kinetin Kinetin: A furanyl adenine found in PLANTS and FUNGI. It has plant growth regulation effects.. cytokinin : A phytohormone that promote cell division, or cytokinesis, in plant roots and shoots.. kinetin : A member of the class of 6-aminopurines that is adenine carrying a (furan-2-ylmethyl) substituent at the exocyclic amino group.	2.07	1	0	6-aminopurines; furans	cytokinin; geroprotector
labetalol Labetalol: A salicylamide derivative that is a non-cardioselective blocker of BETA-ADRENERGIC RECEPTORS and ALPHA-1 ADRENERGIC RECEPTORS.. labetalol : A diastereoisomeric mixture of approximately equal amounts of all four possible stereoisomers ((R,S)-labetolol, (S,R)-labetolol, (S,S)-labetalol and (R,R)-labetalol). It is an adrenergic antagonist used to treat high blood pressure.. 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide : A member of the class of benzamides that is benzamide substituted by a hydroxy group at position 2 and by a 1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl group at position 5.	2.05	1	0	benzamides; benzenes; phenols; primary carboxamide; salicylamides; secondary alcohol; secondary amino compound
lansoprazole Lansoprazole: A 2,2,2-trifluoroethoxypyridyl derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS. Lansoprazole is a racemic mixture of (R)- and (S)-isomers.	2.05	1	0	benzimidazoles; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor
beta-lapachone beta-lapachone: antineoplastic inhibitor of reverse transcriptase, DNA topoisomerase, and DNA polymerase. beta-lapachone : A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities.	2.07	1	0	benzochromenone; orthoquinones	anti-inflammatory agent; antineoplastic agent; plant metabolite
lavendustin a lavendustin A: from Streptomyces griseolavendus; structure given in first source	2.07	1	0	aromatic amine
lavendustin b [no description available]	2.07	1	0
lofepramine Lofepramine: A psychotropic IMIPRAMINE derivative that acts as a tricyclic antidepressant and possesses few anticholinergic properties. It is metabolized to DESIPRAMINE.	2.05	1	0	aromatic ketone; dibenzoazepine; monochlorobenzenes; tertiary amino compound	antidepressant
lomustine [no description available]	2.05	1	0	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent
loratadine Loratadine: A second-generation histamine H1 receptor antagonist used in the treatment of allergic rhinitis and urticaria. Unlike most classical antihistamines (HISTAMINE H1 ANTAGONISTS) it lacks central nervous system depressing effects such as drowsiness.. loratadine : A benzocycloheptapyridine that is 6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine substituted by a chloro group at position 8 and a 1-(ethoxycarbonyl)piperidin-4-ylidene group at position 11. It is a H1-receptor antagonist commonly employed in the treatment of allergic disorders.	2.11	1	0	benzocycloheptapyridine; ethyl ester; N-acylpiperidine; organochlorine compound; tertiary carboxamide	anti-allergic agent; cholinergic antagonist; geroprotector; H1-receptor antagonist
lorazepam Lorazepam: A benzodiazepine used as an anti-anxiety agent with few side effects. It also has hypnotic, anticonvulsant, and considerable sedative properties and has been proposed as a preanesthetic agent.	2.05	1	0	benzodiazepine
2-(4-morpholinyl)-8-phenyl-4h-1-benzopyran-4-one 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one: specific inhibitor of phosphatidylinositol 3-kinase; structure in first source	2.52	2	0	chromones; morpholines; organochlorine compound	autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector
maprotiline Maprotiline: A bridged-ring tetracyclic antidepressant that is both mechanistically and functionally similar to the tricyclic antidepressants, including side effects associated with its use.	2.05	1	0	anthracenes
mazindol Mazindol: Tricyclic anorexigenic agent unrelated to and less toxic than AMPHETAMINE, but with some similar side effects. It inhibits uptake of catecholamines and blocks the binding of cocaine to the dopamine uptake transporter.	2.05	1	0	organic molecular entity
mechlorethamine nitrogen mustard : Compounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.	2.05	1	0	nitrogen mustard; organochlorine compound	alkylating agent
mefloquine hydrochloride [2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol : An organofluorine compound that consists of quinoline bearing trifluoromethyl substituents at positions 2 and 8 as well as a (2-piperidinyl)hydroxymethyl substituent at position 4.	2.05	1	0	organofluorine compound; piperidines; quinolines; secondary alcohol
memantine [no description available]	2.52	2	0	adamantanes; primary aliphatic amine	antidepressant; antiparkinson drug; dopaminergic agent; neuroprotective agent; NMDA receptor antagonist
vitamin k 3 Vitamin K 3: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.	2.07	1	0	1,4-naphthoquinones; vitamin K	angiogenesis inhibitor; antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human urinary metabolite; nutraceutical
mephenytoin Mephenytoin: An anticonvulsant effective in tonic-clonic epilepsy (EPILEPSY, TONIC-CLONIC). It may cause blood dyscrasias.. mephenytoin : An imidazolidine-2,4-dione (hydantoin) in which the imidazolidine nucleus carries a methyl group at N-3 and has ethyl and phenyl substituents at C-5. An anticonvulsant, it is no longer available in the USA or the UK but is still studied largely because of its interesting hydroxylation polymorphism.	2.05	1	0	imidazolidine-2,4-dione	anticonvulsant
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	2.53	2	0	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
methiothepin Methiothepin: A serotonin receptor antagonist in the CENTRAL NERVOUS SYSTEM used as an antipsychotic.. methiothepin : A dibenzothiepine that is 10,11-dihydrodibenzo[b,f]thiepine bearing additional methylthio and 4-methylpiperazin-1-yl substituents at positions 8 and 10 respectively. Potent 5-HT2 antagonist, also active as 5-HT1 antagonist. Differentiates 5-HT1D sub-types. Also displays affinity for rodent 5-HT5B, 5-HT5A, 5-HT7 and 5-HT6 receptors (pK1 values are 6.6, 7.0, 8.4 and 8.7 respectively).	2.06	1	0	aryl sulfide; dibenzothiepine; N-alkylpiperazine; tertiary amino compound	antipsychotic agent; dopaminergic antagonist; geroprotector; serotonergic antagonist
methoxyamine methoxyamine: analytical reagent for aldehydes and ketones; strong irritant, can probably produce methemoglobinemia; RN given refers to parent cpd; structure	2.05	1	0	organooxygen compound
methoxsalen Methoxsalen: A naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA ADDUCTS in the presence of ultraviolet A irradiation.. methoxsalen : A member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis.	2.52	2	0	aromatic ether; psoralens	antineoplastic agent; cross-linking reagent; dermatologic drug; photosensitizing agent; plant metabolite
methoxyflurane Methoxyflurane: An inhalation anesthetic. Currently, methoxyflurane is rarely used for surgical, obstetric, or dental anesthesia. If so employed, it should be administered with NITROUS OXIDE to achieve a relatively light level of anesthesia, and a neuromuscular blocking agent given concurrently to obtain the desired degree of muscular relaxation. (From AMA Drug Evaluations Annual, 1994, p180). methoxyflurane : An ether in which the two groups attached to the central oxygen atom are methyl and 2,2-dichloro-1,1-difluoroethyl.	2.05	1	0	ether; organochlorine compound; organofluorine compound	hepatotoxic agent; inhalation anaesthetic; nephrotoxic agent; non-narcotic analgesic
methylphenidate Methylphenidate: A central nervous system stimulant used most commonly in the treatment of ATTENTION DEFICIT DISORDER in children and for NARCOLEPSY. Its mechanisms appear to be similar to those of DEXTROAMPHETAMINE. The d-isomer of this drug is referred to as DEXMETHYLPHENIDATE HYDROCHLORIDE.. methylphenidate : A racemate comprising equimolar amounts of the two threo isomers of methyl phenyl(piperidin-2-yl)acetate. A central stimulant and indirect-acting sympathomimetic, is used (generally as the hydrochloride salt) in the treatment of hyperactivity disorders in children and for the treatment of narcolepsy.. methyl phenyl(piperidin-2-yl)acetate : A amino acid ester that is methyl phenylacetate in which one of the hydrogens alpha to the carbonyl group is replaced by a piperidin-2-yl group.	2.05	1	0	beta-amino acid ester; methyl ester; piperidines
metoclopramide Metoclopramide: A dopamine D2 antagonist that is used as an antiemetic.. metoclopramide : A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine.	2.05	1	0	benzamides; monochlorobenzenes; substituted aniline; tertiary amino compound	antiemetic; dopaminergic antagonist; environmental contaminant; gastrointestinal drug; xenobiotic
metronidazole Metronidazole: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS.. metronidazole : A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.	2.05	1	0	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
mexiletine Mexiletine: Antiarrhythmic agent pharmacologically similar to LIDOCAINE. It may have some anticonvulsant properties.. mexiletine : An aromatic ether which is 2,6-dimethylphenyl ether of 2-aminopropan-1-ol.	2.05	1	0	aromatic ether; primary amino compound	anti-arrhythmia drug
mianserin Mianserin: A tetracyclic compound with antidepressant effects. It may cause drowsiness and hematological problems. Its mechanism of therapeutic action is not well understood, although it apparently blocks alpha-adrenergic, histamine H1, and some types of serotonin receptors.. mianserin : A dibenzoazepine (specifically 1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine) methyl-substituted on N-2. Closely related to (and now mostly superseded by) the tetracyclic antidepressant mirtazapinean, it is an atypical antidepressant used in the treatment of depression throughout Europe and elsewhere.	2.05	1	0	dibenzoazepine	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; H1-receptor antagonist; histamine agonist; sedative; serotonergic antagonist
midazolam Midazolam: A short-acting hypnotic-sedative drug with anxiolytic and amnestic properties. It is used in dentistry, cardiac surgery, endoscopic procedures, as preanesthetic medication, and as an adjunct to local anesthesia. The short duration and cardiorespiratory stability makes it useful in poor-risk, elderly, and cardiac patients. It is water-soluble at pH less than 4 and lipid-soluble at physiological pH.. midazolam : An imidazobenzodiazepine that is 4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted by a methyl, 2-fluorophenyl and chloro groups at positions 1, 6 and 8, respectively.	9.39	1	1	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative
minoxidil Minoxidil: A potent direct-acting peripheral vasodilator (VASODILATOR AGENTS) that reduces peripheral resistance and produces a fall in BLOOD PRESSURE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p371). minoxidil : A pyrimidine N-oxide that is pyrimidine-2,4-diamine 3-oxide substituted by a piperidin-1-yl group at position 6.	3.92	2	1	dialkylarylamine; tertiary amino compound
myristicin myristicin: asaricin is an isomer; structure; a methylene dioxy version of elemicin;	2.07	1	0	organic molecular entity	metabolite
clorgyline Clorgyline: An antidepressive agent and monoamine oxidase inhibitor related to PARGYLINE.. clorgyline : An aromatic ether that is the 2,4-dichlorophenyl ether of 3-aminopropan-1-ol in which the nitrogen is substituted by a methyl group and a prop-1-yn-3-yl group. A monoamine oxidase inhibitor, it was formerly used as an antidepressant.	2.8	3	0	aromatic ether; dichlorobenzene; terminal acetylenic compound; tertiary amino compound	antidepressant; EC 1.4.3.4 (monoamine oxidase) inhibitor
nabumetone Nabumetone: A butanone non-steroidal anti-inflammatory drug and cyclooxygenase-2 (COX2) inhibitor that is used in the management of pain associated with OSTEOARTHRITIS and RHEUMATOID ARTHRITIS.. nabumetone : A methyl ketone that is 2-butanone in which one of the methyl hydrogens at position 4 is replaced by a 6-methoxy-2-naphthyl group. A prodrug that is converted to the active metabolite, 6-methoxy-2-naphthylacetic acid, following oral administration. It is shown to have a slightly lower risk of gastrointestinal side effects than most other non-steroidal anti-inflammatory drugs.	2.05	1	0	methoxynaphthalene; methyl ketone	cyclooxygenase 2 inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
nalidixic acid [no description available]	2.07	1	0	1,8-naphthyridine derivative; monocarboxylic acid; quinolone antibiotic	antibacterial drug; antimicrobial agent; DNA synthesis inhibitor
neostigmine Neostigmine: A cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike PHYSOSTIGMINE, does not cross the blood-brain barrier.. neostigmine : A quaternary ammonium ion comprising an anilinium ion core having three methyl substituents on the aniline nitrogen, and a 3-[(dimethylcarbamoyl)oxy] substituent at position 3. It is a parasympathomimetic which acts as a reversible acetylcholinesterase inhibitor.	7.53	2	0	quaternary ammonium ion	antidote to curare poisoning; EC 3.1.1.7 (acetylcholinesterase) inhibitor
nevirapine Nevirapine: A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.. nevirapine : A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.	8.42	1	1	cyclopropanes; dipyridodiazepine	antiviral drug; HIV-1 reverse transcriptase inhibitor
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2.78	3	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
nimesulide nimesulide: structure. nimesulide : An aromatic ether having phenyl and 2-methylsulfonamido-5-nitrophenyl as the two aryl groups.	7	1	0	aromatic ether; C-nitro compound; sulfonamide	cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
nimodipine Nimodipine: A calcium channel blockader with preferential cerebrovascular activity. It has marked cerebrovascular dilating effects and lowers blood pressure.. nimodipine : A dihydropyridine that is 1,4-dihydropyridine which is substituted by methyl groups at positions 2 and 6, a (2-methoxyethoxy)carbonyl group at position 3, a m-nitrophenyl group at position 4, and an isopropoxycarbonyl group at position 5. An L-type calcium channel blocker, it acts particularly on cerebral circulation, and is used both orally and intravenously for the prevention and treatment of subarachnoid hemorrhage from ruptured intracranial aneurysm.	2.5	2	0	2-methoxyethyl ester; C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; isopropyl ester	antihypertensive agent; calcium channel blocker; cardiovascular drug; vasodilator agent
nitrendipine Nitrendipine: A calcium channel blocker with marked vasodilator action. It is an effective antihypertensive agent and differs from other calcium channel blockers in that it does not reduce glomerular filtration rate and is mildly natriuretic, rather than sodium retentive.. nitrendipine : A dihydropyridine that is 1,4-dihydropyridine substituted by methyl groups at positions 2 and 6, a 3-nitrophenyl group at position 4, a ethoxycarbonyl group at position 3 and a methoxycarbonyl group at position 5. It is a calcium-channel blocker used in the treatment of hypertension.	2.05	1	0	C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; ethyl ester; methyl ester	antihypertensive agent; calcium channel blocker; geroprotector; vasodilator agent
nitroglycerin Nitroglycerin: A volatile vasodilator which relieves ANGINA PECTORIS by stimulating GUANYLATE CYCLASE and lowering cytosolic calcium. It is also sometimes used for TOCOLYSIS and explosives.. nitroglycerol : A nitrate ester that is glycerol in which nitro group(s) replace the hydrogen(s) attached to one or more of the hydroxy groups.. nitroglycerin : A nitroglycerol that is glycerol in which the hydrogen atoms of all three hydroxy groups are replaced by nitro groups. It acts as a prodrug, releasing nitric oxide to open blood vessels and so alleviate heart pain.	2.41	2	0	nitroglycerol	explosive; muscle relaxant; nitric oxide donor; prodrug; tocolytic agent; vasodilator agent; xenobiotic
nomifensine Nomifensine: An isoquinoline derivative that prevents dopamine reuptake into synaptosomes. The maleate was formerly used in the treatment of depression. It was withdrawn worldwide in 1986 due to the risk of acute hemolytic anemia with intravascular hemolysis resulting from its use. In some cases, renal failure also developed. (From Martindale, The Extra Pharmacopoeia, 30th ed, p266). nomifensine : An N-methylated tetrahydroisoquinoline carrying phenyl and amino substituents at positions C-4 and C-8, respectively.	2.05	1	0	isoquinolines	dopamine uptake inhibitor
norfloxacin Norfloxacin: A synthetic fluoroquinolone (FLUOROQUINOLONES) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA GYRASE.. norfloxacin : A quinolinemonocarboxylic acid with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase.	2.05	1	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug; DNA synthesis inhibitor; environmental contaminant; xenobiotic
nortriptyline Nortriptyline: A metabolite of AMITRIPTYLINE that is also used as an antidepressive agent. Nortriptyline is used in major depression, dysthymia, and atypical depressions.. nortriptyline : An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(methylamino)propylidene group at position 5. It is an active metabolite of amitriptyline.	7.48	2	0	organic tricyclic compound; secondary amine	adrenergic uptake inhibitor; analgesic; antidepressant; antineoplastic agent; apoptosis inducer; drug metabolite
6,7-dimethoxy-3-(4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-isobenzofuran-1-one [no description available]	2.07	1	0	isoquinolines
octopamine Octopamine: An alpha-adrenergic sympathomimetic amine, biosynthesized from tyramine in the CNS and platelets and also in invertebrate nervous systems. It is used to treat hypotension and as a cardiotonic. The natural D(-) form is more potent than the L(+) form in producing cardiovascular adrenergic responses. It is also a neurotransmitter in some invertebrates.. octopamine : A member of the class of phenylethanolamines that is phenol which is substituted at the para- position by a 2-amino-1-hydroxyethyl group. A biogenic phenylethanolamine which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates.	2.17	1	0	phenylethanolamines; tyramines	neurotransmitter
olomoucine olomoucine: inhibits protein P34CDC2. olomoucine : A 9H-purine that is substituted by a (2-hydroxyethyl)nitrilo, benzylnitrilo and a methyl group at positions 2,6 and 9, respectively. It is a cyclin-dependent kinase inhibitor.	2.05	1	0	2,6-diaminopurines; ethanolamines	EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
omeprazole Omeprazole: A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.. omeprazole : A racemate comprising equimolar amounts of (R)- and (S)-omeprazole.. 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.	8.01	4	0	aromatic ether; benzimidazoles; pyridines; sulfoxide
oxatomide oxatomide: structure; an anti-allergic & an anti-asthmatic. oxatomide : A member of the class of benzimidazoles that is 1,3-dihydro-2H-benzimidazol-2-one substituted by a 3-[4-(diphenylmethyl)piperazin-1-yl]propyl group at position 1. It is an anti-allergic drug.	2.05	1	0	benzimidazoles; diarylmethane; N-alkylpiperazine	anti-allergic agent; anti-inflammatory agent; geroprotector; H1-receptor antagonist; serotonergic antagonist
oxazepam Oxazepam: A benzodiazepine used in the treatment of anxiety, alcohol withdrawal, and insomnia.. oxazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a hydroxy group at position 3 and phenyl group at position 5.	2.05	1	0	1,4-benzodiazepinone; organochlorine compound	anxiolytic drug; environmental contaminant; xenobiotic
oxidopamine Oxidopamine: A neurotransmitter analogue that depletes noradrenergic stores in nerve endings and induces a reduction of dopamine levels in the brain. Its mechanism of action is related to the production of cytolytic free-radicals.. oxidopamine : A benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease).	2.82	3	0	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin
oxprenolol Oxprenolol: A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety.	2.05	1	0	aromatic ether
oxyphenbutazone Oxyphenbutazone: A non-steroidal anti-inflammatory drug. Oxyphenbutazone eyedrops have been used abroad in the management of postoperative ocular inflammation, superficial eye injuries, and episcleritis. (From AMA, Drug Evaluations Annual, 1994, p2000) It had been used by mouth in rheumatic disorders such as ankylosing spondylitis, osteoarthritis, and rheumatoid arthritis but such use is no longer considered justified owing to the risk of severe hematological adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p27). oxyphenbutazone : A metabolite of phenylbutazone obtained by hydroxylation at position 4 of one of the phenyl rings. Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following association with blood dyscrasis and Stevens-Johnson syndrome.	2.05	1	0	phenols; pyrazolidines	antimicrobial agent; antineoplastic agent; antipyretic; drug metabolite; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic metabolite
aminosalicylic acid Aminosalicylic Acid: An antitubercular agent often administered in association with ISONIAZID. The sodium salt of the drug is better tolerated than the free acid.. 4-aminosalicylic acid : An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.	2.05	1	0	aminobenzoic acid; phenols	antitubercular agent
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	1.98	1	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
fenclonine Fenclonine: A selective and irreversible inhibitor of tryptophan hydroxylase, a rate-limiting enzyme in the biosynthesis of serotonin (5-HYDROXYTRYPTAMINE). Fenclonine acts pharmacologically to deplete endogenous levels of serotonin.	2.06	1	0	phenylalanine derivative
4-(2'-methoxyphenyl)-1-(2'-(n-(2''-pyridinyl)-4-iodobenzamido)ethyl)piperazine 4-(2'-methoxyphenyl)-1-(2'-(N-(2''-pyridinyl)-4-iodobenzamido)ethyl)piperazine: a 5-HT(1A) ligand; structure in first source	2.06	1	0
pamidronate [no description available]	2.05	1	0	phosphonoacetic acid
pantoprazole Pantoprazole: 2-pyridinylmethylsulfinylbenzimidazole proton pump inhibitor that is used in the treatment of GASTROESOPHAGEAL REFLUX and PEPTIC ULCER.. pantoprazole : A member of the class of benzimidazoles that is 1H-benzimidazole substituted by a difluoromethoxy group at position 5 and a [(3,4-dimethoxypyridin-2-yl)methyl]sulfinyl group at position 2.	2.05	1	0	aromatic ether; benzimidazoles; organofluorine compound; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; environmental contaminant; xenobiotic
papaverine Papaverine: An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels.. papaverine : A benzylisoquinoline alkaloid that is isoquinoline substituted by methoxy groups at positions 6 and 7 and a 3,4-dimethoxybenzyl group at position 1. It has been isolated from Papaver somniferum.	2.05	1	0	benzylisoquinoline alkaloid; dimethoxybenzene; isoquinolines	antispasmodic drug; vasodilator agent
patulin Patulin: 4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one. A mycotoxin produced by several species of Aspergillus and Penicillium. It is found in unfermented apple and grape juice and field crops. It has antibiotic properties and has been shown to be carcinogenic and mutagenic and causes chromosome damage in biological systems.. patulin : A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.	2.07	1	0	furopyran; gamma-lactone; lactol	antimicrobial agent; Aspergillus metabolite; carcinogenic agent; mutagen; mycotoxin; Penicillium metabolite
pd 98059 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one: inhibits MAP kinase kinase (MEK) activity, p42 MAPK and p44 MAPK; structure in first source. 2-(2-amino-3-methoxyphenyl)chromen-4-one : A member of the class of monomethoxyflavones that is 3'-methoxyflavone bearing an additional amino substituent at position 2'.	2.03	1	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
pentamidine Pentamidine: Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.. pentamidine : A diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease.	2.45	2	0	aromatic ether; carboxamidine; diether	anti-inflammatory agent; antifungal agent; calmodulin antagonist; chemokine receptor 5 antagonist; EC 2.3.1.48 (histone acetyltransferase) inhibitor; NMDA receptor antagonist; S100 calcium-binding protein B inhibitor; trypanocidal drug; xenobiotic
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	1.97	1	0	barbiturates	GABAA receptor agonist
perphenazine Perphenazine: An antipsychotic phenothiazine derivative with actions and uses similar to those of CHLORPROMAZINE.. perphenazine : A phenothiazine derivative in which the phenothiazine tricycle carries a chloro substituent at the 2-position and a 3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl group at N-10.	2.05	1	0	N-(2-hydroxyethyl)piperazine; N-alkylpiperazine; organochlorine compound; phenothiazines	antiemetic; dopaminergic antagonist; phenothiazine antipsychotic drug
phenacetin Saridon: contains phenacetin, caffeine, propyphenazone & pyrithyldione	2.05	1	0	acetamides; aromatic ether	cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug
phenindione Phenindione: An indandione that has been used as an anticoagulant. Phenindione has actions similar to WARFARIN, but it is now rarely employed because of its higher incidence of severe adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p234)	2.05	1	0	aromatic ketone; beta-diketone	anticoagulant
phentermine Phentermine: A central nervous system stimulant and sympathomimetic with actions and uses similar to those of DEXTROAMPHETAMINE. It has been used most frequently in the treatment of obesity.	2.05	1	0	primary amine	adrenergic agent; appetite depressant; central nervous system drug; central nervous system stimulant; dopaminergic agent; sympathomimetic agent
phenylbutazone Phenylbutazone: A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.. phenylbutazone : A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.	2.05	1	0	pyrazolidines	antirheumatic drug; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
phloretin [no description available]	2.07	1	0	dihydrochalcones	antineoplastic agent; plant metabolite
primaquine Primaquine: An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404). primaquine : An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.	2.05	1	0	aminoquinoline; aromatic ether; N-substituted diamine	antimalarial
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	1.96	1	0	diarylmethane
procainamide Procainamide: A class Ia antiarrhythmic drug that is structurally-related to PROCAINE.. procainamide : A benzamide that is 4-aminobenzamide substituted on the amide N by a 2-(diethylamino)ethyl group. It is a pharmaceutical antiarrhythmic agent used for the medical treatment of cardiac arrhythmias.	2.05	1	0	benzamides	anti-arrhythmia drug; platelet aggregation inhibitor; sodium channel blocker
procaine Procaine: A local anesthetic of the ester type that has a slow onset and a short duration of action. It is mainly used for infiltration anesthesia, peripheral nerve block, and spinal block. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1016).. procaine : A benzoate ester, formally the result of esterification of 4-aminobenzoic acid with 2-diethylaminoethanol but formed experimentally by reaction of ethyl 4-aminobenzoate with 2-diethylaminoethanol.	2.05	1	0	benzoate ester; substituted aniline; tertiary amino compound	central nervous system depressant; drug allergen; local anaesthetic; peripheral nervous system drug
procarbazine Procarbazine: An antineoplastic agent used primarily in combination with mechlorethamine, vincristine, and prednisone (the MOPP protocol) in the treatment of Hodgkin's disease.. procarbazine : A benzamide obtained by formal condensation of the carboxy group of 4-[(2-methylhydrazino)methyl]benzoic acid with the amino group of isopropylamine. An antineoplastic chemotherapy drug used for treatment of Hodgkin's lymphoma. Metabolism yields azo-procarbazine and hydrogen peroxide, which results in the breaking of DNA strands.	2.05	1	0	benzamides; hydrazines	antineoplastic agent
promethazine Promethazine: A phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals.. promethazine : A tertiary amine that is a substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropan-2-amine moiety.	2.05	1	0	phenothiazines; tertiary amine	anti-allergic agent; anticoronaviral agent; antiemetic; antipruritic drug; H1-receptor antagonist; local anaesthetic; sedative
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	7.71	3	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
pyrimethamine Maloprim: contains above 2 cpds	2.05	1	0	aminopyrimidine; monochlorobenzenes	antimalarial; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor
rabeprazole Rabeprazole: A 4-(3-methoxypropoxy)-3-methylpyridinyl derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.	2.05	1	0	benzimidazoles; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor
ranitidine [no description available]	2.05	1	0	aralkylamine
ropinirole [no description available]	2.25	1	0	indolones; tertiary amine	antidyskinesia agent; antiparkinson drug; central nervous system drug; dopamine agonist
safrole Safrole: A member of the BENZODIOXOLES that is a constituent of several VOLATILE OILS, notably SASSAFRAS oil. It is a precursor in the synthesis of the insecticide PIPERONYL BUTOXIDE and the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA).. safrole : A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sassafras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.	2.66	3	0	benzodioxoles	flavouring agent; insecticide; metabolite; plant metabolite
sanguinarine benzophenanthridine alkaloid : A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.	3.61	2	0	alkaloid antibiotic; benzophenanthridine alkaloid; botanical anti-fungal agent
risedronic acid Risedronic Acid: A pyridine and diphosphonic acid derivative that acts as a CALCIUM CHANNEL BLOCKER and inhibits BONE RESORPTION.	2.05	1	0	pyridines
streptonigrin [no description available]	2.07	1	0	pyridines; quinolone	antimicrobial agent; antineoplastic agent
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	10.86	4	0	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
temozolomide [no description available]	7.25	1	0	imidazotetrazine; monocarboxylic acid amide; triazene derivative	alkylating agent; antineoplastic agent; prodrug
terbutaline Terbutaline: A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic.. terbutaline : A member of the class of phenylethanolamines that is catechol substituted at position 5 by a 2-(tert-butylamino)-1-hydroxyethyl group.	2.05	1	0	phenylethanolamines; resorcinols	anti-asthmatic drug; beta-adrenergic agonist; bronchodilator agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; hypoglycemic agent; sympathomimetic agent; tocolytic agent
terfenadine Terfenadine: A selective histamine H1-receptor antagonist devoid of central nervous system depressant activity. The drug was used for ALLERGY but withdrawn due to causing LONG QT SYNDROME.	2.77	3	0	diarylmethane
tetrahydropapaverine tetrahydropapaverine: RN given refers to parent cpd. 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline : A benzylisoquinoline alkaloid that is norlaudanosoline in which the four phenolic hydrogens have been replaced by methyl groups.	2.07	1	0	aromatic ether; benzylisoquinoline alkaloid; benzyltetrahydroisoquinoline; polyether; secondary amino compound
theobromine Theobromine: 3,7-Dimethylxanthine. The principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than THEOPHYLLINE and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9). theobromine : A dimethylxanthine having the two methyl groups located at positions 3 and 7. A purine alkaloid derived from the cacao plant, it is found in chocolate, as well as in a number of other foods, and is a vasodilator, diuretic and heart stimulator.	2.07	1	0	dimethylxanthine	adenosine receptor antagonist; bronchodilator agent; food component; human blood serum metabolite; mouse metabolite; plant metabolite; vasodilator agent
thioridazine Thioridazine: A phenothiazine antipsychotic used in the management of PHYCOSES, including SCHIZOPHRENIA.. thioridazine : A phenothiazine derivative having a methylsulfanyl subsitituent at the 2-position and a (1-methylpiperidin-2-yl)ethyl] group at the N-10 position.	2.05	1	0	phenothiazines; piperidines	alpha-adrenergic antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; first generation antipsychotic; H1-receptor antagonist; serotonergic antagonist
ticlopidine Ticlopidine: An effective inhibitor of platelet aggregation commonly used in the placement of STENTS in CORONARY ARTERIES.. ticlopidine : A thienopyridine that is 4,5,6,7-tetrahydrothieno[3,2-c]pyridine in which the hydrogen attached to the nitrogen is replaced by an o-chlorobenzyl group.	2.05	1	0	monochlorobenzenes; thienopyridine	anticoagulant; fibrin modulating drug; hematologic agent; P2Y12 receptor antagonist; platelet aggregation inhibitor
tinidazole Tinidazole: A nitroimidazole alkylating agent that is used as an antitrichomonal agent against TRICHOMONAS VAGINALIS; ENTAMOEBA HISTOLYTICA; and GIARDIA LAMBLIA infections. It also acts as an antibacterial agent for the treatment of BACTERIAL VAGINOSIS and anaerobic bacterial infections.. tinidazole : 1H-imidazole substituted at C-1 by a (2-ethylsulfonyl)ethyl group, at C-2 by a methyl group and at C-5 by a nitro group. It is used as an antiprotozoal, antibacterial agent.	2.11	1	0	imidazoles	antiamoebic agent; antibacterial drug; antiparasitic agent; antiprotozoal drug
tolbutamide Tolbutamide: A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). tolbutamide : An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.	2.05	1	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
triamterene Triamterene: A pteridinetriamine compound that inhibits SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS.. triamterene : Pteridine substituted at positions 2, 4 and 7 with amino groups and at position 6 with a phenyl group. A sodium channel blocker, it is used as a diuretic in the treatment of hypertension and oedema.	2.05	1	0	pteridines	diuretic; sodium channel blocker
triazolam Triazolam: A short-acting benzodiazepine used in the treatment of insomnia. Some countries temporarily withdrew triazolam from the market because of concerns about adverse reactions, mostly psychological, associated with higher dose ranges. Its use at lower doses with appropriate care and labeling has been reaffirmed by the FDA and most other countries.	2.05	1	0	triazolobenzodiazepine	sedative
trifluoperazine [no description available]	2.05	1	0	N-alkylpiperazine; N-methylpiperazine; organofluorine compound; phenothiazines	antiemetic; calmodulin antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; phenothiazine antipsychotic drug
trimethadione Trimethadione: An anticonvulsant effective in absence seizures, but generally reserved for refractory cases because of its toxicity. (From AMA Drug Evaluations Annual, 1994, p378). trimethadione : An oxazolidinone that is 1,3-oxazolidine-2,4-dione substituted by methyl groups at positions 3, 5 and 5. It is an antiepileptic agent.	2.05	1	0	oxazolidinone	anticonvulsant; geroprotector
trimethoprim Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.	2.05	1	0	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
trioxsalen Trioxsalen: Pigmenting photosensitizing agent obtained from several plants, mainly Psoralea corylifolia. It is administered either topically or orally in conjunction with ultraviolet light in the treatment of vitiligo.. lactone : Any cyclic carboxylic ester containing a 1-oxacycloalkan-2-one structure, or an analogue having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.. antipsoriatic : A drug used to treat psoriasis.. trioxsalen : 7H-Furo[3,2-g]chromen-7-one in which positions 2, 5, and 9 are substituted by methyl groups. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered orally in conjunction with UV-A for phototherapy treatment of vitiligo. After photoactivation it creates interstrand cross-links in DNA, inhibiting DNA synthesis and cell division, and can lead to cell injury; recovery from the cell injury may be followed by increased melanisation of the epidermis.	2.07	1	0	psoralens	dermatologic drug; photosensitizing agent
troglitazone Troglitazone: A chroman and thiazolidinedione derivative that acts as a PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS (PPAR) agonist. It was formerly used in the treatment of TYPE 2 DIABETES MELLITUS, but has been withdrawn due to hepatotoxicity.	2.04	1	0	chromanes; thiazolidinone	anticoagulant; anticonvulsant; antineoplastic agent; antioxidant; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; hypoglycemic agent; platelet aggregation inhibitor; vasodilator agent
tyramine [no description available]	2.52	2	0	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
zopiclone zopiclone: S(+)-enantiomer of racemic zopiclone; azabicyclo(4.3.0)nonane; a nonbenzodiazepine; one of the so-called of Z drugs (zopiclone, eszopiclone, zolpidem, and zaleplon) for which there is some correlation with tumors; was term of zopiclone 2004-2007. zopiclone : A pyrrolo[3,4-b]pyrazine compound having a 4-methylpiperazine-1-carboxyl group at the 5-position, a 5-chloropyridin-2-yl group at the 6-position and an oxo-substituent at the 7-position.	2.05	1	0	monochloropyridine; pyrrolopyrazine	central nervous system depressant; sedative
mitomycin Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.	7.51	2	0	mitomycin	alkylating agent; antineoplastic agent
corticosterone [no description available]	3.17	5	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
reserpine Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.. reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.	9.78	9	0	alkaloid ester; methyl ester; yohimban alkaloid	adrenergic uptake inhibitor; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; first generation antipsychotic; plant metabolite; xenobiotic
alloxan Alloxan: Acidic compound formed by oxidation of URIC ACID. It is isolated as an efflorescent crystalline hydrate.. alloxan : A member of the class of pyrimidones, the structure of which is that of perhydropyrimidine substituted at C-2, -4, -5 and -6 by oxo groups.	2.07	1	0	pyrimidone	hyperglycemic agent; metabolite
piperonyl butoxide [no description available]	6.97	1	0	benzodioxoles	pesticide synergist
benzimidazole 1H-benzimidazole : The 1H-tautomer of benzimidazole.	2.25	1	0	benzimidazole; polycyclic heteroarene
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	2.01	1	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	2.03	1	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
paramethasone Paramethasone: A glucocorticoid with the general properties of corticosteroids. It has been used by mouth in the treatment of all conditions in which corticosteroid therapy is indicated except adrenal-deficiency states for which its lack of sodium-retaining properties makes it less suitable than HYDROCORTISONE with supplementary FLUDROCORTISONE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p737)	2.05	1	0	fluorinated steroid
pilocarpine hydrochloride pilocarpine hydrochloride : The hydrochloride salt of (+)-pilocarpine, a medication used to treat increased pressure inside the eye and dry mouth.	2.07	1	0	hydrochloride
pilocarpine Pilocarpine: A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.. (+)-pilocarpine : The (+)-enantiomer of pilocarpine.	7.48	2	0	pilocarpine	antiglaucoma drug
pentylenetetrazole Pentylenetetrazole: A pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive GAMMA-AMINOBUTYRIC ACID antagonist. Pentylenetetrazole has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility.. pentetrazol : An organic heterobicyclic compound that is 1H-tetrazole in which the hydrogens at positions 1 and 5 are replaced by a pentane-1,5-diyl group. A central and respiratory stimulant, it was formerly used for the treatment of cough and other respiratory tract disorders, cardiovascular disorders including hypotension, and pruritis.	3.21	5	0	organic heterobicyclic compound; organonitrogen heterocyclic compound
triiodothyronine Triiodothyronine: A T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.. 3,3',5-triiodo-L-thyronine : An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.	2.01	1	0	2-halophenol; amino acid zwitterion; iodophenol; iodothyronine	human metabolite; mouse metabolite; thyroid hormone
diethylnitrosamine Diethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties.. N-nitrosodiethylamine : A nitrosamine that is N-ethylethanamine substituted by a nitroso group at the N-atom.	2.11	1	0	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	2.75	3	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
cantharidin Cantharidin: A toxic compound, isolated from the Spanish fly or blistering beetle (Lytta (Cantharis) vesicatoria) and other insects. It is a potent and specific inhibitor of protein phosphatases 1 (PP1) and 2A (PP2A). This compound can produce severe skin inflammation, and is extremely toxic if ingested orally.. cantharidin : A monoterpenoid with an epoxy-bridged cyclic dicarboxylic anhydride structure secreted by many species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria. Natural toxin inhibitor of protein phosphatases 1 and 2A.	2.07	1	0	cyclic dicarboxylic anhydride; monoterpenoid	EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; herbicide
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	7.15	1	0	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.5	2	0	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	2.25	1	0	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
allyl isothiocyanate allyl isothiocyanate: used in the manufacture of flavors, war gases; medical use as a counterirritant; structure. allyl isothiocyanate : An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152degreeC, it is responsible for the pungent taste of mustard, horseradish, and wasabi.	9.37	6	0	alkenyl isothiocyanate; isothiocyanate	antimicrobial agent; antineoplastic agent; apoptosis inducer; lachrymator; metabolite
cetrimonium bromide cetyltrimethylammonium bromide : The organic bromide salt that is the bromide salt of cetyltrimethylammonium; one of the components of the topical antiseptic cetrimide.	2.05	1	0	organic bromide salt; quaternary ammonium salt	detergent; surfactant
physostigmine Physostigmine: A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.	2.07	1	0	carbamate ester; indole alkaloid	antidote to curare poisoning; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	2.96	4	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	2.72	3	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
apomorphine Apomorphine: A derivative of morphine that is a dopamine D2 agonist. It is a powerful emetic and has been used for that effect in acute poisoning. It has also been used in the diagnosis and treatment of parkinsonism, but its adverse effects limit its use.	2.08	1	0	aporphine alkaloid	alpha-adrenergic drug; antidyskinesia agent; antiparkinson drug; dopamine agonist; emetic; serotonergic drug
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.47	2	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
kanamycin a Kanamycin: Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.. kanamycin : Kanamycin is a naturally occurring antibiotic complex from Streptomyces kanamyceticus that consists of several components: kanamycin A, the major component (also usually designated as kanamycin), and kanamycins B, C, D and X the minor components.	2.07	1	0	kanamycins	bacterial metabolite
galactose galactopyranose : The pyranose form of galactose.	2.81	3	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
phenylephrine Phenylephrine: An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.. phenylephrine : A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.	2.6	1	0	phenols; phenylethanolamines; secondary amino compound	alpha-adrenergic agonist; cardiotonic drug; mydriatic agent; nasal decongestant; protective agent; sympathomimetic agent; vasoconstrictor agent
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	2.05	1	0	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
p-dimethylaminoazobenzene p-Dimethylaminoazobenzene: A reagent used mainly to induce experimental liver cancer. According to the Fourth Annual Report on Carcinogens (NTP 85-002, p. 89) published in 1985, this compound may reasonably be anticipated to be a carcinogen. (Merck, 11th ed)	1.99	1	0	azobenzenes
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	2	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
veratramine veratramine: structure. veratramine : A piperidine alkaloid comprising the 14,15,16,17-tetradehydro derivative of veratraman having two hydroxy groups at the 3- and 23-positions.	2.07	1	0	piperidine alkaloid
phlorhizin [no description available]	2.42	2	0	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	antioxidant; plant metabolite
papaverine hydrochloride [no description available]	2.07	1	0
n-methyltryptamine N-methyltryptamine: RN given refers to parent cpd	2.17	1	0	tryptamine alkaloid; tryptamines	metabolite
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	2.04	1	0	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
zoxazolamine Zoxazolamine: A uricosuric and muscle relaxant. Zoxazolamine acts centrally as a muscle relaxant, but the mechanism of its action is not understood.	1.96	1	0	benzoxazole
1,2-dipalmitoylphosphatidylcholine 1,2-Dipalmitoylphosphatidylcholine: Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.	2.13	1	0
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	2.07	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
colchicine (S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.	2.81	3	0	alkaloid; colchicine	anti-inflammatory agent; gout suppressant; mutagen
yohimbine hydrochloride [no description available]	2.07	1	0
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	2.43	2	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
ficusin Ficusin: A naturally occurring furocoumarin, found in PSORALEA. After photoactivation with UV radiation, it binds DNA via single and double-stranded cross-linking.. psoralen : The simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia.	2.17	1	0	psoralens	plant metabolite
fluocinolone acetonide Fluocinolone Acetonide: A glucocorticoid derivative used topically in the treatment of various skin disorders. It is usually employed as a cream, gel, lotion, or ointment. It has also been used topically in the treatment of inflammatory eye, ear, and nose disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732). fluocinolone acetonide : A fluorinated steroid that is flunisolide in which the hydrogen at position 9 is replaced by fluorine. A corticosteroid with glucocorticoid activity, it is used (both as the anhydrous form and as the dihydrate) in creams, gels and ointments for the treatment of various skin disorders.	2.05	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; cyclic ketal; fluorinated steroid; glucocorticoid; organic heteropentacyclic compound; primary alpha-hydroxy ketone	anti-inflammatory drug; antipruritic drug
gliotoxin Gliotoxin: A fungal toxin produced by various species of Trichoderma, Gladiocladium fimbriatum, Aspergillus fumigatus, and Penicillium. It is used as an immunosuppressive agent.. gliotoxin : A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi.	2.07	1	0	dipeptide; organic disulfide; organic heterotetracyclic compound; pyrazinoindole	antifungal agent; EC 2.5.1.58 (protein farnesyltransferase) inhibitor; immunosuppressive agent; mycotoxin; proteasome inhibitor
tubercidin Tubercidin: An antibiotic purine ribonucleoside that readily substitutes for adenosine in the biological system, but its incorporation into DNA and RNA has an inhibitory effect on the metabolism of these nucleic acids.. tubercidin : An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus.	2.07	1	0	antibiotic antifungal agent; N-glycosylpyrrolopyrimidine; ribonucleoside	antimetabolite; antineoplastic agent; bacterial metabolite
mannitol [no description available]	2.05	1	0	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
cytarabine [no description available]	2.05	1	0	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	1.99	1	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
veratridine [no description available]	2.07	1	0	steroid	sodium channel modulator
sulfobromophthalein sodium bromosulfophthalein sodium : An organic sodium salt that is the disodium salt of bromosulfophthalein.. bromosulfophthalein : An organosulfonic acid that consists of phthalide bearing four bromo substituents at positions 4, 5, 6 and 7 as well as two 4-hydroxy-3-sulfophenyl groups both located at position 1.	2.05	1	0	organic sodium salt	dye
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	2.41	1	0	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
threonine Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.	2.08	1	0	amino acid zwitterion; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid; threonine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	2.03	1	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
gibberellic acid gibberellic acid: RN given refers to (1alpha,2beta,4aalpha,4bbeta,10beta)-isomer; structure. gibberellin A3 : A C19-gibberellin that is a pentacyclic diterpenoid responsible for promoting growth and elongation of cells in plants. Initially identified in Gibberella fujikuroi,it differs from gibberellin A1 in the presence of a double bond between C-3 and C-4.	2.07	1	0	C19-gibberellin; gibberellin monocarboxylic acid; lactone; organic heteropentacyclic compound	mouse metabolite; plant metabolite
bisphenol a 4,4'-isopropylidene diphenol: stimulates proliferative responses and cytokine productions of murine spleen cells and thymus cells in vitro. bisphenol : By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom.. bisphenol A : A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.	2.31	1	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
visnagin visnagin: from Musineon divaricatum. visnagin : A furanochromone that is furo[3,2-g]chromen-5-one which is substituted at positions 4 and 7 by methoxy and methyl groups, respectively. Found in the toothpick-plant, Ammi visnaga.	2.07	1	0	aromatic ether; furanochromone; polyketide	anti-inflammatory agent; antihypertensive agent; EC 1.1.1.37 (malate dehydrogenase) inhibitor; phytotoxin; plant metabolite; vasodilator agent
methylprednisolone Methylprednisolone: A PREDNISOLONE derivative with similar anti-inflammatory action.. 6alpha-methylprednisolone : The 6alpha-stereoisomer of 6-methylprednisolone.	2.05	1	0	6-methylprednisolone; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antiemetic; environmental contaminant; neuroprotective agent; xenobiotic
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	3.23	5	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
skimmianine skimmianine: furanoquinoline alkaloid from Teclea (RUTACEAE)	2.07	1	0	alkaloid antibiotic; organic heterotricyclic compound; organonitrogen heterocyclic compound; oxacycle
syrosingopine syrosingopine: was heading 1963-94; SYRINGOPINE was see SYROSINGOPINE 1977-94; use RESERPINE to search SYROSINGOPINE 1966-94	2.07	1	0	yohimban alkaloid
gramine gramine : An aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3.	2.52	2	0	aminoalkylindole; indole alkaloid; tertiary amino compound	antibacterial agent; antiviral agent; plant metabolite; serotonergic antagonist
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	2.54	2	0	pyrrolidin-2-ones
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	2.49	2	0	monoterpenoid; phenols	volatile oil component
pseudoephedrine Pseudoephedrine: A phenethylamine that is an isomer of EPHEDRINE which has less central nervous system effects and usage is mainly for respiratory tract decongestion.. pseudoephedrine : A member of the class of the class of phenylethanolamines that is (1S)-2-(methylamino)-1-phenylethan-1-ol in which the pro-S hydrogen at position 2 is replaced by a methyl group.	2.05	1	0	phenylethanolamines; secondary alcohol; secondary amino compound	anti-asthmatic drug; bronchodilator agent; central nervous system drug; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
piperonylic acid piperonylic acid: RN given refers to parent cpd; structure. piperonylic acid : A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a carboxy group at position 5. It is a natural product isolated from several plant species. It is a selective mechanism-based inactivator of the trans-cinnamate 4-hydroxylase enzyme and exhibits antifungal and skin wound healing properties.	2.11	1	0	aromatic carboxylic acid; benzodioxoles; monocarboxylic acid	antifungal agent; EC 1.14.14.91 ( trans-cinnamate 4-monooxygenase) inhibitor; plant metabolite; vulnerary
acrolein [no description available]	4.92	7	0	enal	herbicide; human xenobiotic metabolite; toxin
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	2.25	1	0	pyrrole; secondary amine
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.15	1	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
piperidine [no description available]	2.5	2	0	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
carbitol carbitol: used as lubricating oil & in braking fluid, structure. diethylene glycol monoethyl ether : A primary alcohol that is ethanol substituted by a 2-ethoxyethoxy group at position 2.	2.25	1	0	diether; glycol ether; hydroxypolyether; primary alcohol	protic solvent
methylergonovine Methylergonovine: A homolog of ERGONOVINE containing one more CH2 group. (Merck Index, 11th ed)	2.07	1	0	ergoline alkaloid
phenformin Phenformin: A biguanide hypoglycemic agent with actions and uses similar to those of METFORMIN. Although it is generally considered to be associated with an unacceptably high incidence of lactic acidosis, often fatal, it is still available in some countries. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). phenformin : A member of the class of biguanides that is biguanide in which one of the terminal nitrogen atoms is substituted by a 2-phenylethyl group. It was used as an anti-diabetic drug but was later withdrawn from the market due to potential risk of lactic acidosis.	2.05	1	0	biguanides	antineoplastic agent; geroprotector; hypoglycemic agent
2,2'-methylenebis(4-methyl-6-tert-butylphenol) [no description available]	2.07	1	0	diarylmethane
piperonal piperonal: has been used as a pediculicide; structure. piperonal : An arenecarbaldehyde that is 1,3-benzodioxole substituted by a formyl substituent at position 5. It has been isolated from Piper nigrum.	8	4	0	arenecarbaldehyde; benzodioxoles	fragrance; insect repellent; plant metabolite
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	2.42	2	0	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
triethylamine [no description available]	2.25	1	0	tertiary amine
pyrazolanthrone pyrazolanthrone: JNK (c-Jun N-terminal kinase) inhibitor; structure in first source. anthra[1,9-cd]pyrazol-6(2H)-one : A member of the class of anthrapyrazoles that is anthra[1,9-cd]pyrazole substituted at position 6 by an oxo group. An inhibitor of c-Jun N-terminal kinase.	2.17	1	0	anthrapyrazole; aromatic ketone; cyclic ketone	antineoplastic agent; c-Jun N-terminal kinase inhibitor; geroprotector
meglumine Meglumine: 1-Deoxy-1-(methylamino)-D-glucitol. A derivative of sorbitol in which the hydroxyl group in position 1 is replaced by a methylamino group. Often used in conjunction with iodinated organic compounds as contrast medium.. N-methylglucamine : A hexosamine that is D-glucitol in which the hydroxy group at position 1 is substituted by the nitrogen of a methylamino group. A crystalline base, it is used in preparing salts of certain acids for use as diagnostic radiopaque media, while its antimonate is used as an antiprotozoal in the treatment of leishmaniasis.	7.17	1	0	hexosamine; secondary amino compound
indolebutyric acid indolebutyric acid: RN given refers to parent cpd. indole-3-butyric acid : A indol-3-yl carboxylic acid that is butanoic acid carrying a 1H-indol-3-yl substituent at position 1.	2.07	1	0	indol-3-yl carboxylic acid	auxin; plant hormone; plant metabolite
shikimic acid Shikimic Acid: A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.. shikimic acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms.	2.07	1	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
sterogenol hexadecylpyridinium bromide: structure in first source. cetylpyridinium bromide : A pyridinium salt that has N-hexadecylpyridinium as the cation and bromide as the anion.	2.05	1	0	bromide salt; pyridinium salt	antiseptic drug; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; surfactant
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2.03	1	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
yohimbine Yohimbine: A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION.. yohimbine : An indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina.	2.46	2	0	methyl 17-hydroxy-20xi-yohimban-16-carboxylate	alpha-adrenergic antagonist; dopamine receptor D2 antagonist; serotonergic antagonist
cycloguanil cycloguanil: the active metabolite of proguanil; antifolate drug; structure in first source. cycloguanil : A triazine in which a 1,6-dihydro-1,3,5-triazine ring is substituted at N-1 by a 4-chlorophenyl group, at C-2 and -4 by amino groups and at C-6 by gem-dimethyl groups. A dihydrofolate reductase inhibitor, it is a metabolite of the antimalarial drug proguanil.	2.05	1	0	triazines	antifolate; antiinfective agent; antimalarial; antiparasitic agent; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	14.23	12	2	catechin	antioxidant; plant metabolite
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	1.96	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	2.1	1	0	indazole
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	2.17	1	0	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	2.03	1	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
1,2,4-triazole 1,2,4-triazole: RN given refers to 1H-1,2,4-triazole	7.08	1	0	1,2,4-triazole
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	2.48	2	0	diazine; pyrazines	Daphnia magna metabolite
nitroblue tetrazolium Nitroblue Tetrazolium: Colorless to yellow dye that is reducible to blue or black formazan crystals by certain cells; formerly used to distinguish between nonbacterial and bacterial diseases, the latter causing neutrophils to reduce the dye; used to confirm diagnosis of chronic granulomatous disease.	2.02	1	0	organic cation
hydrazine diamine : Any polyamine that contains two amino groups.	2.49	2	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
monocrotaline Monocrotaline: A pyrrolizidine alkaloid and a toxic plant constituent that poisons livestock and humans through the ingestion of contaminated grains and other foods. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature. Significant attenuation of the cardiopulmonary changes are noted after oral magnesium treatment.	2.07	1	0	pyrrolizidine alkaloid
methyl-4-tyramine methyl-4-tyramine: found in barley malt; RN given refers to parent cpd; structure given in first source	2.17	1	0	tyramines	mouse metabolite
betamethasone Betamethasone: A glucocorticoid given orally, parenterally, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. Its lack of mineralocorticoid properties makes betamethasone particularly suitable for treating cerebral edema and congenital adrenal hyperplasia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p724)	2.05	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-asthmatic agent; anti-inflammatory drug; immunosuppressive agent
fluorobenzenes Fluorobenzenes: Derivatives of BENZENE that contain FLUORINE.. monofluorobenzene : The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.. fluorobenzenes : Any fluoroarene that is a benzene or a substituted benzene carrying at least one fluoro group.	2.08	1	0	monofluorobenzenes	NMR chemical shift reference compound
jervine jervine: teratogen from Veratrum grandiflorum; RN given refers to parent cpd(3beta,23beta)-isomer; structure	2.07	1	0	piperidines
dextropropoxyphene Dextropropoxyphene: A narcotic analgesic structurally related to METHADONE. Only the dextro-isomer has an analgesic effect; the levo-isomer appears to exert an antitussive effect.. propoxyphene : A racemate of the (1R,2R)- and (1S,2R)- diastereoisomers.. dextropropoxyphene : The (1S,2R)-(+)-diastereoisomer of propoxyphene.	2.05	1	0	1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propanoate	mu-opioid receptor agonist; opioid analgesic
glycyrrhetinic acid [no description available]	2.49	2	0	cyclic terpene ketone; hydroxy monocarboxylic acid; pentacyclic triterpenoid	immunomodulator; plant metabolite
naphthazarin naphthazarin: fish toxin; isolated for first time from the walnut onigurmi, Juglans mandshurica maxim var. Sieboldiana Makino; structure. naphthazarin : A naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 5 and 8 are replaced by hydroxy groups.	2.17	1	0	hydroxy-1,4-naphthoquinone	acaricide; antibacterial agent; antineoplastic agent; apoptosis inducer; geroprotector; plant metabolite
boldine [no description available]	2.07	1	0	aporphine alkaloid
indirubin [no description available]	2.07	1	0
plumbagin plumbagin: a superoxide anion generator. plumbagin : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.	3.18	5	0	hydroxy-1,4-naphthoquinone; phenols	anticoagulant; antineoplastic agent; immunological adjuvant; metabolite
cepharanthine cepharanthine: isoquinoline alkaloid from tubers of STEPHANIA; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation. cepharanthine : A bisbenzylisoquinoline alkaloid from tubers of Stephania; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation.	7.77	3	0	bisbenzylisoquinoline alkaloid; isoquinolines
aloe emodin aloe emodin: structure distinct from emodin; this does not mean emodin from aloe. Aloe emodin : A dihydroxyanthraquinone that is chrysazin carrying a hydroxymethyl group at position 3. It has been isolated from plant species of the genus Aloe.	2.07	1	0	aromatic primary alcohol; dihydroxyanthraquinone	antineoplastic agent; plant metabolite
imperatorin imperatorin: tumor necrosis factor antagonist; furanocoumarin from West African medicinal plant Clausena anisata; structure in Negwer, 5th ed, #3005. imperatorin : A member of the class of psoralens that is psoralen substituted by a prenyloxy group at position 8. Isolated from Angelica dahurica and Angelica koreana, it acts as a acetylcholinesterase inhibitor.	2.17	1	0	psoralens	EC 3.1.1.7 (acetylcholinesterase) inhibitor; metabolite
emetine Emetine: The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae. It is used as an amebicide in many different preparations and may cause serious cardiac, hepatic, or renal damage and violent diarrhea and vomiting. Emetine inhibits protein synthesis in EUKARYOTIC CELLS but not PROKARYOTIC CELLS.. emetine : A pyridoisoquinoline comprising emetam having methoxy substituents at the 6'-, 7'-, 10- and 11-positions. It is an antiprotozoal agent and emetic. It inhibits SARS-CoV2, Zika and Ebola virus replication and displays antimalarial, antineoplastic and antiamoebic properties.	2.48	2	0	isoquinoline alkaloid; pyridoisoquinoline	antiamoebic agent; anticoronaviral agent; antiinfective agent; antimalarial; antineoplastic agent; antiprotozoal drug; antiviral agent; autophagy inhibitor; emetic; expectorant; plant metabolite; protein synthesis inhibitor
osthol osthol: from Cnidium monnieri and Angelica pubescens (both Apiaceae); structure given in first source	2.52	2	0	botanical anti-fungal agent; coumarins	metabolite
cytisine [no description available]	2.07	1	0	alkaloid; bridged compound; lactam; organic heterotricyclic compound; secondary amino compound	nicotinic acetylcholine receptor agonist; phytotoxin; plant metabolite
bicuculline Bicuculline: An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.. bicuculline : A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.	2.07	1	0	benzylisoquinoline alkaloid; isoquinoline alkaloid; isoquinolines	agrochemical; central nervous system stimulant; GABA-gated chloride channel antagonist; GABAA receptor antagonist; neurotoxin
kainic acid Kainic Acid: (2S-(2 alpha,3 beta,4 beta))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid. Ascaricide obtained from the red alga Digenea simplex. It is a potent excitatory amino acid agonist at some types of excitatory amino acid receptors and has been used to discriminate among receptor types. Like many excitatory amino acid agonists it can cause neurotoxicity and has been used experimentally for that purpose.	7.93	4	0	dicarboxylic acid; L-proline derivative; non-proteinogenic L-alpha-amino acid; pyrrolidinecarboxylic acid	antinematodal drug; excitatory amino acid agonist
thymoquinone thymoquinone: constituent of cedarwood; can cause dermatitis; structure. thymoquinone : A member of the class of 1,4-benzoquinones that is 1,4-bezoquinone in which the hydrogens at positions 2 and 5 are replaced by methyl and isopropyl groups, respectively. It is a natural compound isolated from Nigella sativa which has demonstrated promising chemotherapeutic activity.	4.69	4	0	1,4-benzoquinones	adjuvant; anti-inflammatory agent; antidepressant; antineoplastic agent; antioxidant; cardioprotective agent; plant metabolite
benzohydroxamic acid [no description available]	2.05	1	0
carvacrol carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).	7.03	1	0	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	2.06	1	0
mustard gas Mustard Gas: Severe irritant and vesicant of skin, eyes, and lungs. It may cause blindness and lethal lung edema and was formerly used as a war gas. The substance has been proposed as a cytostatic and for treatment of psoriasis. It has been listed as a known carcinogen in the Fourth Annual Report on Carcinogens (NTP-85-002, 1985) (Merck, 11th ed).. bis(2-chloroethyl) sulfide : An ethyl sulfide that is diethyl sulfide in which a hydrogen from each of the terminal methyl groups is replaced by a chlorine. It is a powerful vesicant regulated under the Chemical Weapons Convention.	3.51	1	1	ethyl sulfide; organochlorine compound	alkylating agent; carcinogenic agent; vesicant
oleanolic acid [no description available]	7.57	2	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	2.07	1	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
hesperidin Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	7.52	2	0	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
medroxyprogesterone [no description available]	2.05	1	0	17alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(4) steroid; tertiary alpha-hydroxy ketone	contraceptive drug; progestin; synthetic oral contraceptive
dihydrotestosterone Dihydrotestosterone: A potent androgenic metabolite of TESTOSTERONE. It is produced by the action of the enzyme 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE.. 17beta-hydroxyandrostan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4-5 double bond has been reduced to a single bond with unspecified configuration at position 5.. 17beta-hydroxy-5alpha-androstan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5.	2.11	1	0	17beta-hydroxy steroid; 17beta-hydroxyandrostan-3-one; 3-oxo-5alpha-steroid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
angelicin angelicin: used as tranquillizer; sedative; or anticonvulsant; structure	2.17	1	0	furanocoumarin
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	2.07	1	0	C-nitro compound; imidazoles	antitubercular agent
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	6.69	19	3	dialdehyde	biomarker
paeonol paeonol: structure	7.54	2	0	methoxybenzenes; phenols	metabolite
n-methylphenethylamine N-methylphenethylamine: substrate for type A & B monoamine oxidase; RN given refers to parent cpd	2.17	1	0
allyl sulfide allyl sulfide: essence of garlic; inhibits CYP2E1	4.59	4	0	organic sulfide
megestrol acetate [no description available]	2.05	1	0	20-oxo steroid; 3-oxo-Delta(4) steroid; acetate ester; steroid ester	antineoplastic agent; appetite enhancer; contraceptive drug; progestin; synthetic oral contraceptive
alpha-naphthoflavone alpha-naphthoflavone: inhibits P4501A1 and P4501A2; stimulates some activities of P4503A4. alpha-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14).	2.17	1	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist; aryl hydrocarbon receptor antagonist; EC 1.14.14.14 (aromatase) inhibitor
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	3.02	4	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
Berberine chloride (TN) [no description available]	2.8	3	0	organic molecular entity
erythromycin Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.	3.61	2	0	cyclic ketone; erythromycin
2-piperidone 2-piperidone: structure given in first source. piperidin-2-one : A delta-lactam that is piperidine which is substituted by an oxo group at position 2.	2.73	3	0	delta-lactam; piperidones	EC 1.2.1.88 (L-glutamate gamma-semialdehyde dehydrogenase) inhibitor
methylnitrosourea Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.	2.13	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
ethambutol Ethambutol: An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863). ethambutol : An ethylenediamine derivative that is ethane-1,2-diamine in which one hydrogen attached to each of the nitrogens is sutstituted by a 1-hydroxybutan-2-yl group (S,S-configuration). It is a bacteriostatic antimycobacterial drug, effective against Mycobacterium tuberculosis and some other mycobacteria. It is used (as the dihydrochloride salt) in combination with other antituberculous drugs in the treatment of pulmonary and extrapulmonary tuberculosis; resistant strains of M. tuberculosis are readily produced if ethambutol is used alone.	2.13	1	0	ethanolamines; ethylenediamine derivative	antitubercular agent; environmental contaminant; xenobiotic
vancomycin Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.	2.17	1	0	glycopeptide	antibacterial drug; antimicrobial agent; bacterial metabolite
glycyrrhizic acid glycyrrhizinic acid : A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.	8.99	3	0	enone; glucosiduronic acid; pentacyclic triterpenoid; tricarboxylic acid; triterpenoid saponin	EC 3.4.21.5 (thrombin) inhibitor; plant metabolite
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	4.24	6	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
lysergol lysergol: structure given in first source; RN given refers to (8beta)-isomer. lysergol : An alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi and in the morning glory family of plants. Its structure is that of ergoline with a methyl group at N-6 and a beta-hydroxymethyl substituent at C-8.	3.19	1	0	ergoline alkaloid
vincamine Vincamine: A major alkaloid of Vinca minor L., Apocynaceae. It has been used therapeutically as a vasodilator and antihypertensive agent, particularly in cerebrovascular disorders.	2.07	1	0	alkaloid ester; hemiaminal; methyl ester; organic heteropentacyclic compound; vinca alkaloid	antihypertensive agent; metabolite; vasodilator agent
stearylamine stearylamine: RN given refers to parent cpd. octadecan-1-amine : An 18-carbon primary aliphatic amine.	2.04	1	0	primary aliphatic amine	film-forming compound
paraquat Paraquat: A poisonous dipyridilium compound used as contact herbicide. Contact with concentrated solutions causes irritation of the skin, cracking and shedding of the nails, and delayed healing of cuts and wounds.. paraquat : An organic cation that consists of 4,4'-bipyridine bearing two N-methyl substituents loctated at the 1- and 1'-positions.	7.25	1	0	organic cation	geroprotector; herbicide
pristane pristane: structure. pristane : A norterpene that is an acyclic saturated hydrocarbon derived from phytane by loss of its C-16 terminal methyl group.	7.66	2	0	long-chain alkane; norterpene	biomarker; immunological adjuvant
2-tert-butylhydroquinone 2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent. 2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.	2.25	1	0	hydroquinones	food antioxidant
dronabinol Dronabinol: A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound.. Delta(9)-tetrahydrocannabinol : A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.	6.18	3	1	benzochromene; diterpenoid; phytocannabinoid; polyketide	cannabinoid receptor agonist; epitope; hallucinogen; metabolite; non-narcotic analgesic
diallyl trisulfide [no description available]	3.21	1	0	organic trisulfide	anti-inflammatory agent; antilipemic drug; antineoplastic agent; antioxidant; antiprotozoal drug; apoptosis inducer; estrogen receptor antagonist; insecticide; platelet aggregation inhibitor; vasodilator agent
glaucine glaucine: RN given refers to (+-)-isomer	3.25	1	0	aporphine alkaloid; organic heterotetracyclic compound; polyether; tertiary amino compound	antibacterial agent; antineoplastic agent; antitussive; muscle relaxant; NF-kappaB inhibitor; plant metabolite; platelet aggregation inhibitor; rat metabolite
muscarine [no description available]	2.07	1	0
thioflavin t thioflavin T: RN given refers to chloride; structure. thioflavine T : An organic chloride salt having 2-[4-(dimethylamino)phenyl]-3,6-dimethyl-1,3-benzothiazol-3-ium as the counterion. It is widely used to visualise and quantify the presence of amyloids, both in vitro and in vivo.	2.31	1	0	organic chloride salt	fluorochrome; geroprotector; histological dye
sulfadoxine Sulfadoxine: A long acting sulfonamide that is used, usually in combination with other drugs, for respiratory, urinary tract, and malarial infections.. sulfadoxine : A sulfonamide consisting of pyrimidine having methoxy substituents at the 5- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position. In combination with the antiprotozoal pyrimethamine (CHEBI:8673) it is used as an antimalarial.	2.05	1	0	pyrimidines; sulfonamide	antibacterial drug; antimalarial
uridine diphosphate glucuronic acid Uridine Diphosphate Glucuronic Acid: A nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP iduronic acid, which donates iduronic acid to polysaccharides. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones.. UDP-alpha-D-glucuronic acid : A UDP-sugar having alpha-D-glucuronic acid as the sugar component.	1.96	1	0	UDP-D-glucuronic acid	Escherichia coli metabolite; human metabolite; mouse metabolite
acetophenazine acetophenazine: major descriptor (73-85); minor descriptor (64-72); on-line search PHENOTHIAZINES (64-85); Index Medicus search PHENOTHIAZINES (64-72); ACETOPHENAZINE (73-85); RN given refers to parent cpd. acetophenazine : A member of the class of phenothiazines that is 10H-phenothiazine substituted by a 3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl group at the nitogen atom and an acetyl group at position 2.	2.05	1	0	N-(2-hydroxyethyl)piperazine; N-alkylpiperazine; phenothiazines	phenothiazine antipsychotic drug
dicloxacillin Dicloxacillin: One of the PENICILLINS which is resistant to PENICILLINASE.. dicloxacillin : A penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]formyl group.	2.17	1	0	dichlorobenzene; penicillin	antibacterial drug
mannose mannopyranose : The pyranose form of mannose.	7	1	0	D-aldohexose; D-mannose; mannopyranose	metabolite
ecdysone [no description available]	2.07	1	0	14alpha-hydroxy steroid; 22-hydroxy steroid; 25-hydroxy steroid; 2beta-hydroxy steroid; 3beta-sterol; 6-oxo steroid; ecdysteroid	prohormone
tranylcypromine Tranylcypromine: A propylamine formed from the cyclization of the side chain of amphetamine. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in panic and phobic disorders. (From AMA Drug Evaluations Annual, 1994, p311). tranylcypromine : A racemate comprising equal amounts of (1R,2S)- and (1S,2R)-2-phenylcyclopropan-1-amine. An irreversible monoamine oxidase inhibitor that is used as an antidepressant (INN tranylcypromine).. (1R,2S)-tranylcypromine : A 2-phenylcyclopropan-1-amine that is the (1R,2S)-enantiomer of tranylcypromine.	2.04	1	0	2-phenylcyclopropan-1-amine
streptomycin [no description available]	3.65	2	0	antibiotic antifungal drug; antibiotic fungicide; streptomycins	antibacterial drug; antifungal agrochemical; antimicrobial agent; antimicrobial drug; bacterial metabolite; protein synthesis inhibitor
beclomethasone [no description available]	2.05	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; chlorinated steroid; corticosteroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-asthmatic drug; anti-inflammatory drug
tabersonine [no description available]	2.17	1	0	alkaloid ester; methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound	antineoplastic agent; metabolite
pyrodifenium bromide pyrodifenium bromide: was heading 1976-94 (see under PYRROLIDINES 1976-90); PRIFINIUM BROMIDE was see PYRODIFENIUM BROMIDE 1976-94: use PYRROLIDINES to search PYRODIFENIUM BROMIDE 1976-94; quaternary ammonium anticholinergic agent more specific for the gastrointestinal tract than atropine	2.05	1	0	organic molecular entity
ochratoxin b ochratoxin B: structure given in first source. ochratoxin B : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid. Ochratoxin B differs from the more naturally abundant ochratoxin A in the absence of the dihydroisocoumarin chlorine atom. It has cytotoxic effects on kidney and liver cells in vitro but only minor effects in vivo, due to its rapid metabolism and excretion. It inhibits cell proliferation of human liver HepG2 cells at doses as low as 1 mug/ ml but lacks the genotoxic activity of ochratoxin A, even at higher concentrations.	2.03	1	0	isochromanes; monocarboxylic acid; N-acyl-L-phenylalanine; phenylalanine derivative	Aspergillus metabolite; calcium channel blocker; mycotoxin; Penicillium metabolite
limonene Limonene: A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA).. limonene : A monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively.	1.98	1	0	cycloalkene; p-menthadiene	human metabolite
n-deacetyl-n-formylcolchicine N-deacetyl-N-formylcolchicine: structure given in first source	2.07	1	0	cyclic ketone
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	7.46	2	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	7.49	2	0	cadmium molecular entity; zinc group element atom
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	7.25	1	0	copper group element atom; elemental gold
aluminum chloride Aluminum Chloride: A compound with the chemical formula AlCl3; the anhydrous salt is used as a catalyst in organic chemical synthesis, and hydrated salts are used topically as antiperspirants, and for the management of HYPERHYDROSIS.	2.31	1	0	aluminium coordination entity	Lewis acid
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	3.8	3	0	D-galactosamine; primary amino compound	toxin
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.07	1	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
phosphine phosphane : The simplest phosphine, consisting of a single phosphorus atom with three hydrogens attached.. phosphine : Phosphane (PH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RPH2, R2PH, R3P (R =/= H) are called primary, secondary and tertiary phosphines, respectively. A specific phosphine is preferably named as a substituted phosphane.	2.02	1	0	mononuclear parent hydride; phosphanes; phosphine	carcinogenic agent; fumigant insecticide
tricalcium phosphate tricalcium phosphate: a form of tricalcium phosphate used as bioceramic bone replacement material; see also records for alpha-tricalcium phosphate, beta-tricalcium phosphate, calcium phosphate; apatitic tricalcium phosphate Ca9(HPO4)(PO4)5(OH) is the calcium orthophosphate leading to beta tricalcium phosphate Ca3(PO4)2 (b-TCP). calcium phosphate : A calcium salt composed of calcium and phosphate/diphosphate ions; present in milk and used for the mineralisation of calcified tissues.	2.6	1	0	calcium phosphate
nitrous acid Nitrous Acid: Nitrous acid (HNO2). A weak acid that exists only in solution. It can form water-soluble nitrites and stable esters. (From Merck Index, 11th ed)	1.98	1	0	nitrogen oxoacid
cadmium chloride Cadmium Chloride: A cadmium halide in the form of colorless crystals, soluble in water, methanol, and ethanol. It is used in photography, in dyeing, and calico printing, and as a solution to precipitate sulfides. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). cadmium dichloride : A cadmium coordination entity in which cadmium(2+) and Cl(-) ions are present in the ratio 2:1. Although considered to be ionic, it has considerable covalent character to its bonding.	2.44	2	0	cadmium coordination entity
amopyroquine amopyroquine: RN given refers to parent cpd; structure	2.05	1	0
3-hydroxybenzo(a)pyrene 3-hydroxybenzo(a)pyrene: RN given refers to unlabeled parent cpd	1.96	1	0	ortho- and peri-fused polycyclic arene
benzo(a)pyrene 7,8-dihydrodiol benzo(a)pyrene 7,8-dihydrodiol: RN given refers to cpd without isomeric designation	1.99	1	0	pyrenes
beryllium nitrate [no description available]	2.04	1	0
xipamide Xipamide: A sulfamoylbenzamide analog of CLOPAMIDE. It is diuretic and saluretic with antihypertensive activity. It is bound to PLASMA PROTEINS, thus has a delayed onset and prolonged action.	2.05	1	0	benzamides
selegiline Selegiline: A selective, irreversible inhibitor of Type B monoamine oxidase that is used for the treatment of newly diagnosed patients with PARKINSON DISEASE, and for the treatment of depressive disorders. The compound without isomeric designation is Deprenyl.	2.78	3	0	selegiline; terminal acetylenic compound	geroprotector
levamisole Levamisole: An antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. (From Smith and Reynard, Textbook of Pharmacology, 1991, p435-6). levamisole : A 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole that has S configuration. It is used (generally as the monohydrochloride salt) to treat parasitic worm infections in pigs, sheep and cattle and was formerly used in humans as an adjuvant to chemotherapy for the treatment of various cancers. It is also widely used as an adulterant to coccaine.	2.05	1	0	6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole	antinematodal drug; antirheumatic drug; EC 3.1.3.1 (alkaline phosphatase) inhibitor; immunological adjuvant; immunomodulator
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.76	3	0	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
ornidazole Ornidazole: A nitroimidazole antiprotozoal agent used in ameba and trichomonas infections. It is partially plasma-bound and also has radiation-sensitizing action.. ornidazole : A C-nitro compound that is 5-nitroimidazole in which the hydrogens at positions 1 and 2 are replaced by 3-chloro-2-hydroxypropyl and methyl groups, respectively. It is used in the treatment of susceptible protozoal infections and for the treatment of anaerobic bacterial infections.	2.05	1	0	C-nitro compound; imidazoles; organochlorine compound; secondary alcohol	antiamoebic agent; antibacterial drug; antiinfective agent; antiprotozoal drug; antitrichomonal drug; epitope
danazol Danazol: A synthetic steroid with antigonadotropic and anti-estrogenic activities that acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties. Danazol has been used in the treatment of endometriosis and some benign breast disorders.	2.05	1	0	17beta-hydroxy steroid; terminal acetylenic compound	anti-estrogen; estrogen antagonist; geroprotector
2-bromoergocryptine mesylate [no description available]	2.07	1	0	methanesulfonate salt	antiparkinson drug
bromocriptine Bromocriptine: A semisynthetic ergotamine alkaloid that is a dopamine D2 agonist. It suppresses prolactin secretion.	2.05	1	0	indole alkaloid	antidyskinesia agent; antiparkinson drug; dopamine agonist; hormone antagonist
zingerone zingerone: pungent principle of ginger; structure. zingerone : A methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.	4.64	6	1	methyl ketone; monomethoxybenzene; phenols	anti-inflammatory agent; antiemetic; antioxidant; flavouring agent; fragrance; plant metabolite; radiation protective agent
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.47	2	0	benzenes; phenyl acetates
triamcinolone Triamcinolone: A glucocorticoid given, as the free alcohol or in esterified form, orally, intramuscularly, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. (From Martindale, The Extra Pharmacopoeia, 30th ed, p739). triamcinolone : A C21-steroid hormone that is 1,4-pregnadiene-3,20-dione carrying four hydroxy substituents at positions 11beta, 16alpha, 17alpha and 21 as well as a fluoro substituent at position 9. Used in the form of its 16,17-acetonide to treat various skin infections.	2.05	1	0	11beta-hydroxy steroid; 16alpha-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-allergic agent; anti-inflammatory drug
benzonidazole benzonidazole: used in treatment of Chagas' disease. benznidazole : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2-nitroimidazol-1-yl)acetic acid with the aromatic amino group of benzylamine. Used for treatment of Chagas disease.	2.73	3	0	C-nitro compound; imidazoles; monocarboxylic acid amide	antiprotozoal drug
halazepam halazepam: structure	2.05	1	0	organic molecular entity
transferrin Transferrin: An iron-binding beta1-globulin that is synthesized in the LIVER and secreted into the blood. It plays a central role in the transport of IRON throughout the circulation. A variety of transferrin isoforms exist in humans, including some that are considered markers for specific disease states.	7.31	1	0
alkenes [no description available]	2.77	3	0
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.8	3	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
dexchlorpheniramine dexchlorpheniramine: RN given refers to parent cpd(S)-isomer	2.05	1	0	chlorphenamine
adenylyl imidodiphosphate Adenylyl Imidodiphosphate: 5'-Adenylic acid, monoanhydride with imidodiphosphoric acid. An analog of ATP, in which the oxygen atom bridging the beta to the gamma phosphate is replaced by a nitrogen atom. It is a potent competitive inhibitor of soluble and membrane-bound mitochondrial ATPase and also inhibits ATP-dependent reactions of oxidative phosphorylation.	2.08	1	0	adenosine 5'-phosphate
oxypeucadanin, (s)-(-)-isomer [no description available]	2.17	1	0	epoxide; furanocoumarin; lactone	plant metabolite
amoxicillin Amoxicillin: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.. amoxicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group.	2.01	1	0	penicillin allergen; penicillin	antibacterial drug
timolol (S)-timolol (anhydrous) : The (S)-(-) (more active) enantiomer of timolol. A beta-adrenergic antagonist, both the hemihydrate and the maleate salt are used in the mangement of glaucoma, hypertension, angina pectoris and myocardial infarction, and for the prevention of migraine.	2.05	1	0	timolol	anti-arrhythmia drug; antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist
amineptin amineptin: used in treatment of neuroses with psychoasthenic, anxio-phobic & depressive manifestations; synonym S 1694 refers to HCl; structure. amineptine : A carbocyclic fatty acid that is 5-aminoheptanoic acid in which one of the hydrogens attached to the nitrogen is replaced by a 10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl group. A tricyclic antidepressant, it was never approved in the US and was withdrawn from the French market in 1999 due to concerns over abuse, dependence and severe acne.	2.05	1	0	amino acid; carbocyclic fatty acid; carbotricyclic compound; secondary amino compound	antidepressant; dopamine uptake inhibitor
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	3.12	4	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
etoposide [no description available]	7.75	3	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
substance p [no description available]	2.9	4	0	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
halofantrine halofantrine: used in treatment of mild to moderate acute malaria	2.05	1	0	phenanthrenes
phorbol 12,13-dibutyrate Phorbol 12,13-Dibutyrate: A phorbol ester found in CROTON OIL which, in addition to being a potent skin tumor promoter, is also an effective activator of calcium-activated, phospholipid-dependent protein kinase (protein kinase C). Due to its activation of this enzyme, phorbol 12,13-dibutyrate profoundly affects many different biological systems.	2.07	1	0	butyrate ester; phorbol ester; tertiary alpha-hydroxy ketone
cephradine Cephradine: A semi-synthetic cephalosporin antibiotic.. cephradine : A first-generation cephalosporin antibiotic with a methyl substituent at position 3, and a (2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetamido substituent at position 7, of the cephem skeleton.	2.07	1	0	beta-lactam antibiotic allergen; cephalosporin	antibacterial drug
hydroxymaprotilin hydroxymaprotilin: RN given refers to cpd without isomeric designation	2.05	1	0
methyldopa Methyldopa: An alpha-2 adrenergic agonist that has both central and peripheral nervous system effects. Its primary clinical use is as an antihypertensive agent.. alpha-methyl-L-dopa : A derivative of L-tyrosine having a methyl group at the alpha-position and an additional hydroxy group at the 3-position on the phenyl ring.	2.05	1	0	L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	alpha-adrenergic agonist; antihypertensive agent; hapten; peripheral nervous system drug; sympatholytic agent
tocainide Tocainide: An antiarrhythmic agent which exerts a potential- and frequency-dependent block of SODIUM CHANNELS.. tocainide : A monocarboxylic acid amide in which 2,6-dimethylphenylaniline and isobutyric acid have combined to form the amide bond; used as a local anaesthetic.	2.05	1	0	monocarboxylic acid amide	anti-arrhythmia drug; local anaesthetic; sodium channel blocker
sq-11725 Nadolol: A non-selective beta-adrenergic antagonist with a long half-life, used in cardiovascular disease to treat arrhythmias, angina pectoris, and hypertension. Nadolol is also used for MIGRAINE DISORDERS and for tremor.. nadolol : Nadolol is a diastereoisomeric mixture consisting of equimolar amounts of the four possible 2,3-cis-isomers of 5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol.	2.05	1	0
diltiazem Diltiazem: A benzothiazepine derivative with vasodilating action due to its antagonism of the actions of CALCIUM ion on membrane functions.. diltiazem : A 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate in which both stereocentres have S configuration. A calcium-channel blocker and vasodilator, it is used as the hydrochloride in the management of angina pectoris and hypertension.	7.47	2	0	5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate	antihypertensive agent; calcium channel blocker; vasodilator agent
1-methyl-4-phenylpyridinium 1-Methyl-4-phenylpyridinium: An active neurotoxic metabolite of 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE. The compound reduces dopamine levels, inhibits the biosynthesis of catecholamines, depletes cardiac norepinephrine and inactivates tyrosine hydroxylase. These and other toxic effects lead to cessation of oxidative phosphorylation, ATP depletion, and cell death. The compound, which is related to PARAQUAT, has also been used as an herbicide.. N-methyl-4-phenylpyridinium : A pyridinium ion that is N-methylpyridinium having a phenyl substituent at the 4-position.	7.03	1	0	pyridinium ion	apoptosis inducer; herbicide; human xenobiotic metabolite; neurotoxin
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	3.13	5	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
permethrin hemoglobin Atlanta-Coventry: Leu replaced by Pro at beta75 and Leu deleted at beta141	2.01	1	0	cyclopropanecarboxylate ester; cyclopropanes	agrochemical; ectoparasiticide; pyrethroid ester acaricide; pyrethroid ester insecticide; scabicide
pinazepam pinazepam: structure	2.05	1	0	benzodiazepine
quisqualic acid Quisqualic Acid: An agonist at two subsets of excitatory amino acid receptors, ionotropic receptors that directly control membrane channels and metabotropic receptors that indirectly mediate calcium mobilization from intracellular stores. The compound is obtained from the seeds and fruit of Quisqualis chinensis.	2.07	1	0	non-proteinogenic alpha-amino acid
decamethrin decamethrin: pyrethroid insecticide; RN given refers to cpd without isomeric designation; structure	2.82	3	0	aromatic ether; cyclopropanecarboxylate ester; nitrile; organobromine compound	agrochemical; antifeedant; calcium channel agonist; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; pyrethroid ester insecticide
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	1.99	1	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
butibufen butibufen: RN given refers to parent cpd	2.05	1	0	monoterpenoid
enkephalin, methionine Enkephalin, Methionine: One of the endogenous pentapeptides with morphine-like activity. It differs from LEU-ENKEPHALIN by the amino acid METHIONINE in position 5. Its first four amino acid sequence is identical to the tetrapeptide sequence at the N-terminal of BETA-ENDORPHIN.	1.96	1	0
paroxetine Paroxetine: A serotonin uptake inhibitor that is effective in the treatment of depression.. paroxetine : A benzodioxole that consists of piperidine bearing 1,3-benzodioxol-5-yloxy)methyl and 4-fluorophenyl substituents at positions 3 and 4 respectively; the (3S,4R)-diastereomer. Highly potent and selective 5-HT uptake inhibitor that binds with high affinity to the serotonin transporter (Ki = 0.05 nM). Ki values are 1.1, 350 and 1100 nM for inhibition of [3H]-5-HT, [3H]-l-NA and [3H]-DA uptake respectively. Displays minimal affinity for alpha1-, alpha2- or beta-adrenoceptors, 5-HT2A, 5-HT1A, D2 or H1 receptors at concentrations below 1000 nM, however displays weak affinity for muscarinic ACh receptors (Ki = 42 nM). Antidepressant and anxiolytic in vivo.	2.05	1	0	aromatic ether; benzodioxoles; organofluorine compound; piperidines	antidepressant; anxiolytic drug; hepatotoxic agent; P450 inhibitor; serotonin uptake inhibitor
captopril Captopril: A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.. captopril : A L-proline derivative in which L-proline is substituted on nitrogen with a (2S)-2-methyl-3-sulfanylpropanoyl group. It is used as an anti-hypertensive ACE inhibitor drug.	2.05	1	0	alkanethiol; L-proline derivative; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
staurosporine [no description available]	3.59	2	0	indolocarbazole alkaloid; organic heterooctacyclic compound	apoptosis inducer; bacterial metabolite; EC 2.7.11.13 (protein kinase C) inhibitor; geroprotector
ethylcholine aziridinium ethylcholine aziridinium: causes passive avoidance deficits	2.05	1	0
colforsin Colforsin: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant COLEUS FORSKOHLII. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.	2.07	1	0	acetate ester; cyclic ketone; labdane diterpenoid; organic heterotricyclic compound; tertiary alpha-hydroxy ketone; triol	adenylate cyclase agonist; anti-HIV agent; antihypertensive agent; plant metabolite; platelet aggregation inhibitor; protein kinase A agonist
cefadroxil anhydrous Cefadroxil: Long-acting, broad-spectrum, water-soluble, CEPHALEXIN derivative.. cefadroxil : A cephalosporin bearing methyl and (2R)-2-amino-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton.	2.01	1	0	cephalosporin	antibacterial drug
alfentanil Alfentanil: A short-acting opioid anesthetic and analgesic derivative of FENTANYL. It produces an early peak analgesic effect and fast recovery of consciousness. Alfentanil is effective as an anesthetic during surgery, for supplementation of analgesia during surgical procedures, and as an analgesic for critically ill patients.. alfentanil : A member of the class of piperidines that is piperidine having a 2-(4-ethyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl)ethyl group at the 1-position as well as N-phenylpropanamido- and methoxymethyl groups at the 4-position.	2.05	1	0	monocarboxylic acid amide; piperidines	central nervous system depressant; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic; peripheral nervous system drug
swainsonine Swainsonine: An indolizidine alkaloid from the plant Swainsona canescens that is a potent alpha-mannosidase inhibitor. Swainsonine also exhibits antimetastatic, antiproliferative, and immunomodulatory activity.. swainsonine : An indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8.	2.07	1	0	indolizidine alkaloid	antineoplastic agent; EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase) inhibitor; immunological adjuvant; plant metabolite
lovastatin Lovastatin: A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.. lovastatin : A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom).	2.41	1	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	anticholesteremic drug; antineoplastic agent; Aspergillus metabolite; prodrug
rimcazole rimcazole: RN given refers to (cis)-isomer; structure given in first source	2.04	1	0	carbazoles
piritrexim piritrexim: RN given refers to parent cpd; structure given in first source	2.05	1	0
castanospermine castanospermine: indolizidine alkaloid from seeds of Australian legume, Castanospermum australe. castanospermine : A tetrahydroxyindolizidine alkaloid that consists of octahydroindolizine having four hydroxy substituents located at positions 1, 6, 7 and 8 (the 1S,6S,7R,8R,8aR-diastereomer).	2.07	1	0	indolizidine alkaloid	anti-HIV-1 agent; anti-inflammatory agent; EC 3.2.1.* (glycosidase) inhibitor; metabolite
simvastatin Simvastatin: A derivative of LOVASTATIN and potent competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It may also interfere with steroid hormone production. Due to the induction of hepatic LDL RECEPTORS, it increases breakdown of LDL CHOLESTEROL.. simvastatin : A member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug.	3.02	4	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; statin (semi-synthetic)	EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; ferroptosis inducer; geroprotector; prodrug
bambuterol bambuterol: selective inhibitor of butyrylcholinesterase & acetylcholinesterase. bambuterol : A carbamate ester that is terbutaline in which both of the phenolic hydroxy groups have been protected as the corresponding N,N-dimethylcarbamates. A long acting beta-adrenoceptor agonist used in the treatment of asthma, it is a prodrug for terbutaline.	2.05	1	0	carbamate ester; phenylethanolamines	anti-asthmatic drug; beta-adrenergic agonist; bronchodilator agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; prodrug; sympathomimetic agent; tocolytic agent
raloxifene hydrochloride Raloxifene Hydrochloride: A second generation selective estrogen receptor modulator (SERM) used to prevent osteoporosis in postmenopausal women. It has estrogen agonist effects on bone and cholesterol metabolism but behaves as a complete estrogen antagonist on mammary gland and uterine tissue.. raloxifene hydrochloride : A hydrochloride salt resulting from the reaction of equimolar amounts of raloxifene and hydrogen chloride.	2.17	1	0	hydrochloride	bone density conservation agent; estrogen antagonist; estrogen receptor modulator
salmeterol xinafoate Salmeterol Xinafoate: A selective ADRENERGIC BETA-2 RECEPTOR agonist that functions as a BRONCHODILATOR when administered by inhalation. It is used to manage the symptoms of ASTHMA and CHRONIC OBSTRUCTIVE PULMONARY DISEASE.	2.05	1	0	naphthoic acid
imiquimod Imiquimod: A topically-applied aminoquinoline immune modulator that induces interferon production. It is used in the treatment of external genital and perianal warts, superficial CARCINOMA, BASAL CELL; and ACTINIC KERATOSIS.. imiquimod : An imidazoquinoline fused [4,5-c] carrying isobutyl and amino substituents at N-1 and C-4 respectively. A prescription medication, it acts as an immune response modifier and is used to treat genital warts, superficial basal cell carcinoma, and actinic keratosis.	2.6	1	0	imidazoquinoline	antineoplastic agent; interferon inducer
zileuton [no description available]	2.21	1	0	1-benzothiophenes; ureas	anti-asthmatic drug; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; ferroptosis inhibitor; leukotriene antagonist; non-steroidal anti-inflammatory drug
marbofloxacin [no description available]	7.21	1	0	quinolines
atorvastatin [no description available]	7.72	2	0	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic
lamivudine [no description available]	2.08	1	0	monothioacetal; nucleoside analogue; oxacycle; primary alcohol	allergen; anti-HBV agent; antiviral drug; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor; HIV-1 reverse transcriptase inhibitor; prodrug
valsartan Valsartan: A tetrazole derivative and ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKER that is used to treat HYPERTENSION.. valsartan : A monocarboxylic acid amide consisting of L-valine in which the amino hydrogens have been replaced by a pentanoyl and a [2'-(1H-tetrazol-5-yl)biphenyl]-4-yl]methyl group. It exhibits antihypertensive activity.	2.11	1	0	biphenylyltetrazole; monocarboxylic acid amide; monocarboxylic acid	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
ibandronic acid Ibandronic Acid: Aminobisphosphonate that is a potent inhibitor of BONE RESORPTION. It is used in the treatment of HYPERCALCEMIA associated with malignancy, for the prevention of fracture and bone complications in patients with breast cancer and bone metastases, and for the treatment and prevention of POSTMENOPAUSAL OSTEOPOROSIS.	2.05	1	0
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.43	2	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
metaldehyde metaldehyde: polymer of acetaldehyde. metaldehyde : A member of the class of tetroxocanes that is 1,3,5,7-tetroxocane which carries four methyl groups at positions 2,4,6 and 8. It is a potent molluscicide and the active ingredient in most slug pellets used for crop protection.	3.15	1	0	tetroxocane	fuel; molluscicide
benzylaminopurine benzylaminopurine: a plant growth regulator. N-benzyladenine : A member of the class of 6-aminopurines that is adenine in which one of the hydrogens of the amino group is replaced by a benzyl group.	2.17	1	0	6-aminopurines	cytokinin; plant metabolite
daunorubicin hydrochloride [no description available]	2.07	1	0	anthracycline
trovafloxacin trovafloxacin: a trifluoronaphthyridone derivative of 7-(3-azabicyclo(3.1.0)hexyl)naphthyridone; has antineoplastic activity. trovafloxacin : A 1,8-naphthyridine derivative that is 4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid bearing additional 2,4-difluorophenyl, fluoro and 6-amino-3-azabicyclo[3.1.0]hex-3-yl substituents at positions 1, 6 and 7 respectively. A broad-spectrum antibiotic that was withdrawn from the market due to risk of liver failure.	2.05	1	0
terfenadine [no description available]	2.11	1	0	diarylmethane
methionine methyl ester [no description available]	2.05	1	0
mevastatin mevastatin: antifungal metabolite from Penicillium brevicopactum; potent inhibitory activity to sterol synthesis; structure. mevastatin : A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals.	2.07	1	0	2-pyranones; carboxylic ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	antifungal agent; apoptosis inducer; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; fungal metabolite; Penicillium metabolite
ursolic acid [no description available]	2.47	2	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
propamidine propamidine: structure given in first source. propamidine : A polyether that is the bis(4-guanidinophenyl) ether of propane-1,3-diol. Used (as its isethionate salt) for the treatment of minor eye or eyelid infections, such as conjunctivitis and blepharitis.	2.05	1	0	aromatic ether; guanidines; polyether	antimicrobial agent; antiseptic drug
meglumine antimoniate Meglumine Antimoniate: ANTIMONY salt of meglumine that is used in the treatment of LEISHMANIASIS.	7.17	1	0
norharman norharman: RN given refers to parent cpd. beta-carboline : The parent compound of the beta-carbolines, a tricyclic structure comprising an indole ring system ortho- fused to C-3 and C-4 of a pyridine ring.	2.46	2	0	beta-carbolines; mancude organic heterotricyclic parent	fungal metabolite; marine metabolite
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	2.03	1	0	organic bromide salt	colorimetric reagent; dye
betulinic acid [no description available]	2.52	2	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-HIV agent; anti-inflammatory agent; antimalarial; antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; plant metabolite
allicin [no description available]	3.12	1	0	botanical anti-fungal agent; sulfoxide	antibacterial agent
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	14.23	12	2	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
salvin salvin: a biocyclic diterpenoid; from sage and rosemary (Lamiaceae)	3.85	3	0	abietane diterpenoid; carbotricyclic compound; catechols; monocarboxylic acid	angiogenesis modulating agent; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; food preservative; HIV protease inhibitor; plant metabolite
1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose pentagalloylglucose: pentahydroxy gallic acid ester of glucose; a phytogenic antineoplastic agent and antibacterial agent. 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose : A galloyl-beta-D-glucose compound having five galloyl groups in the 1-, 2-, 3-, 4- and 6-positions.	2.17	1	0	gallate ester; galloyl beta-D-glucose	anti-inflammatory agent; antineoplastic agent; geroprotector; hepatoprotective agent; plant metabolite; radiation protective agent; radical scavenger
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	2	1	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
baccatin iii [no description available]	2.07	1	0	acetate ester; benzoate ester; tetracyclic diterpenoid	plant metabolite
4-nitrobenzylthioinosine 4-nitrobenzylthioinosine: inhibitor of nucleoside transport; acts on ENT1	1.98	1	0	purine nucleoside
taleranol taleranol: a metabolite of ZEARALENONE which is a non-steroidal estrogenic lactone used as an anabolic compound in animal feed; a stereoisomer of ZERANOL (alpha-zearalanol)	2.07	1	0	macrolide
narasin [no description available]	2.07	1	0	diterpene glycoside
sinefungin [no description available]	2.05	1	0	adenosines; non-proteinogenic alpha-amino acid	antifungal agent; antimicrobial agent
quassin quassin: article discusses quassinoid principle; structure	2.07	1	0	triterpenoid
tomatidine tomatidine: RN given refers to (3beta,5alpha,22beta,25S)-isomer; structure. tomatidine : A 3beta-hydroxy steroid resulting from the substitution of the 3beta-hydrogen of tomatidane by a hydroxy group.	2.07	1	0	3beta-hydroxy steroid; azaspiro compound; oxaspiro compound
aloxistatin aloxistatin: a membrane-permeable cysteine protease inhibitor. aloxistatin : An L-leucine derivative that is the amide obtained by formal condensation of the carboxy group of (2S,3S)-3-(ethoxycarbonyl)oxirane-2-carboxylic acid with the amino group of N-(3-methylbutyl)-L-leucinamide.	2.07	1	0	epoxide; ethyl ester; L-leucine derivative; monocarboxylic acid amide	anticoronaviral agent; cathepsin B inhibitor
droxicam droxicam: structure given in first source. droxicam : An organic heterotricyclic compound that is 2H,5H-[1,3]oxazino[5,6-c][1,2]benzothiazine-2,4(3H)-dione 6,6-dioxide substituted at positions 3 and 5 by pyridin-2-yl and methyl groups respectively. A prodrug of piroxicam, it is used for the relief of pain and inflammation in musculoskeletal disorders such as rheumatoid arthritis and osteoarthritis.	2.05	1	0	organic heterotricyclic compound; pyridines	cyclooxygenase 1 inhibitor; hepatotoxic agent; non-narcotic analgesic; non-steroidal anti-inflammatory drug; platelet aggregation inhibitor; prodrug
rutecarpine rutacarpine: from Evodia rutaecarpa; an ingredient in zhuyu hewei zhitong capsules	2.07	1	0	beta-carbolines
etofibrate etofibrate: analog of clofibrate with nicotinic acid substituted on the 2-carbon of the ethyl ester group; structure; RN given refers to parent cpd	2.05	1	0	monocarboxylic acid
anpirtoline anpirtoline: structure given in first source	2.06	1	0	aryl sulfide
telmisartan Telmisartan: A biphenyl compound and benzimidazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION.. telmisartan : A member of the class of benzimidazoles used widely in the treatment of hypertension.	2.11	1	0	benzimidazoles; biphenyls; carboxybiphenyl	angiotensin receptor antagonist; antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; environmental contaminant; xenobiotic
bergenin bergenin: RN refers to (2R-(2alpha,3beta,4alpha,4aalpha,10bbeta))-isomer; structure	2.07	1	0	trihydroxybenzoic acid	metabolite
valerophenone [no description available]	2.25	1	0	aromatic ketone	plant metabolite; volatile oil component
dexfenfluramine Dexfenfluramine: The S-isomer of FENFLURAMINE. It is a serotonin agonist and is used as an anorectic. Unlike fenfluramine, it does not possess any catecholamine agonist activity.. (S)-fenfluramine : The S-enantiomer of fenfluramine. It stimulates the release of serotonin and selectively inhibits its reuptake, but unlike fenfluramine it does not possess catecholamine agonist activity. It was formerly given by mouth as the hydrochloride in the treatment of obesity, but, like fenfluramine, was withdrawn wolrdwide following reports of valvular heart defects.	2.05	1	0	fenfluramine	appetite depressant; serotonergic agonist; serotonin uptake inhibitor
synthalin a synthalin A: RN given refers to parent cpd; structure. synthalin : A hydrochloride resulting from the reaction of decamethylenediguanidine with 2 mol eq. of hydrogen chloride.. synthalin A : A member of the class of guanidines that is decane having guanidino groups at the 1- and 10-positions.	2.05	1	0	guanidines	hepatotoxic agent; hypoglycemic agent; nephrotoxin
1,7-phenanthroline [no description available]	2.05	1	0	phenanthroline
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	7.08	1	0	1,2,3-triazole
pinocembrin pinocembrin : A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea.	2.07	1	0	(2S)-flavan-4-one; dihydroxyflavanone	antineoplastic agent; antioxidant; metabolite; neuroprotective agent; vasodilator agent
isopimpinellin isopimpinellin: from Ruta graveolens & Heracleum lanatum; structure	2.17	1	0	psoralens
ibopamine ibopamine: structure given in UD 31;67a & in 2nd source	2.05	1	0	benzoate ester; phenols
zoledronic acid Zoledronic Acid: An imidobisphosphonate inhibitor of BONE RESORPTION that is used for the treatment of malignancy-related HYPERCALCEMIA; OSTEITIS DEFORMANS; and OSTEOPOROSIS.. zoledronic acid : An imidazole compound having a 2,2-bis(phosphono)-2-hydroxyethane-1-yl substituent at the 1-position.	2.05	1	0	1,1-bis(phosphonic acid); imidazoles	bone density conservation agent
pirlindole pirlindole: RN given refers to parent cpd; synonym pyrazidol refers to mono-HCl; structure in Negwer, 5th ed, #2812	2.05	1	0	carbazoles
artemisinin (+)-artemisinin : A sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.	2.04	1	0	organic peroxide; sesquiterpene lactone	antimalarial; plant metabolite
artemether Artemether: An artemisinin derivative that is used in the treatment of MALARIA.. artemether : An artemisinin derivative that is artemisinin in which the lactone has been converted to the corresponding lactol methyl ether. It is used in combination with lumefantrine as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.	2.05	1	0	artemisinin derivative; cyclic acetal; organic peroxide; semisynthetic derivative; sesquiterpenoid	antimalarial
isoscopoletin isoscopoletin : A hydroxycoumarin that is esculetin in which the hydroxy group at position 7 is replaced by a methoxy group. It is the major primary metabolite of scoparone.	2.07	1	0	aromatic ether; hydroxycoumarin	plant metabolite
tyrosine methyl ester tyrosine methyl ester: RN given refers to (L)-isomer. methyl L-tyrosinate : An L-tyrosyl ester that is the methyl ester of L-tyrosine.	2.05	1	0	L-tyrosyl ester; methyl ester
vinburnine [no description available]	2.07	1	0	alkaloid
6-amino-1-hydroxyhexane-1,1-diphosphonate 6-amino-1-hydroxyhexane-1,1-diphosphonate: used for therapy of Paget's disease of bone & malignant hypercalcaemia	2.05	1	0	1,1-bis(phosphonic acid)
tocophersolan tocophersolan: RN given refers to parent cpd	2.25	1	0	tocol
rexigen clobenzorex: RN given refers to (+)-isomer; structure	2.05	1	0
aceclofenac [no description available]	2.48	2	0	amino acid; carboxylic ester; dichlorobenzene; monocarboxylic acid; secondary amino compound	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
clociguanil clociguanil: RN given refers to parent cpd; structure	2.05	1	0
tebuquine [no description available]	2.05	1	0
epicatechin (-)-epicatechin : A catechin with (2R,3R)-configuration.	2.07	1	0	catechin; polyphenol	antioxidant
hesperetin [no description available]	7.57	2	0	3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone	antineoplastic agent; antioxidant; plant metabolite
magnolol [no description available]	4.18	4	0	biphenyls
honokiol [no description available]	2.07	1	0	biphenyls
sesamin (+)-sesamin : A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR stereoisomer). Isolated from Cinnamomum camphora, it exhibits cytotoxic activity.	2.03	1	0	benzodioxoles; furofuran; lignan	antineoplastic agent; neuroprotective agent; plant metabolite
chelerythrine chloride [no description available]	2.07	1	0
betulin betulin: isolated from various white birch bark (BETULA). betulin : A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.	2.07	1	0	diol; pentacyclic triterpenoid	analgesic; anti-inflammatory agent; antineoplastic agent; antiviral agent; metabolite
tetrahydroalstonine tetrahydroalstonine : A heteropentacyclic compound that is (20alpha)-16,17-didehydro-18-oxayohimban which is substituted at position 16 by a methoxycarbonyl group and at position 19 by a methyl group. It is a metabolite found in several plant species.	2.07	1	0	methyl ester; organic heteropentacyclic compound; yohimban alkaloid	plant metabolite
hernandezine hernandezine: from Thalictrum glandulosissimum; structure given in first source; RN given refers to (1beta)-isomer; RN for cpd without isomeric designation not avail 3/91	2.07	1	0	bisbenzylisoquinoline alkaloid; isoquinolines
picropodophyllin picropodophyllin: isolated from American May apple (Podophyllum); inhibits IGF-I autophosphorylation without interfering with tyrosine kinase activity. picropodophyllotoxin : An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing 3,4,5-trimethoxyphenyl and hydroxy substituents.	2.07	1	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antineoplastic agent; insulin-like growth factor receptor 1 antagonist; plant metabolite; tyrosine kinase inhibitor
vexibinol vexibinol: flavanol from Sophora; structure in first source; RN given refers to (S-(R,S))-isomer. sophoraflavanone G : A tetrahydroxyflavanone having a structure of naringenin bearing an additional hydroxyl substituent at position 2' as well as a (2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl (lavandulyl) substituent at position 8'.	2.15	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; tetrahydroxyflavanone	antimalarial; antimicrobial agent; antioxidant; plant metabolite
tetrandrine tetrandrine: a bisbenzylisoquinoline that exhibits antifibrogenic activity	2.07	1	0	bisbenzylisoquinoline alkaloid; isoquinolines
dehydrocostus lactone dehydrocostus lactone : An organic heterotricyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-bis(methylene)decahydoazulen-5-yl group and in which the hydroxy group and the carboxy group have undergone formal condensation to afford the corresponding gamma-lactone.	2.07	1	0	gamma-lactone; guaiane sesquiterpenoid; organic heterotricyclic compound; sesquiterpene lactone	antimycobacterial drug; antineoplastic agent; apoptosis inducer; cyclooxygenase 2 inhibitor; metabolite; trypanocidal drug
madecassic acid [no description available]	2.07	1	0	monocarboxylic acid; pentacyclic triterpenoid; tetrol	antioxidant; plant metabolite
panaxadiol panaxadiol: a protopanaxadiol with the side chain cyclized into a pyran which is an artifact of acidic hydrolysis; RN refers to (3 beta,12 beta,20R)-isomer	2.07	1	0	triterpenoid saponin
tryptanthrine tryptanthrine: minor constituent of traditional Chinese medicine qing dai	3.61	2	0	alkaloid antibiotic; organic heterotetracyclic compound; organonitrogen heterocyclic compound
homoeriodictyol homoeriodictyol: structure in first source. homoeriodictyol : A trihydroxyflavanone that consists of 3'-methoxyflavanone in which the three hydroxy substituents are located at positions 4', 5, and 7.	2.07	1	0	3'-methoxyflavanones; 4'-hydroxyflavanones; monomethoxyflavanone; trihydroxyflavanone	flavouring agent; metabolite
maslinic acid (2Alpha,3beta)-2,3-dihydroxyolean-12-en-28-oic acid: from Luehea divaricata and Agrimonia eupatoria	2.17	1	0	dihydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory agent; antineoplastic agent; antioxidant; plant metabolite
atovaquone Atovaquone: A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols.. atovaquone : A naphthoquinone compound having a 4-(4-chlorophenyl)cyclohexyl group at the 2-position and a hydroxy substituent at the 3-position.	2.05	1	0	hydroxy-1,2-naphthoquinone
4-hydroxyindole hydroxyindoles : Any member of the class of indoles carrying at least one hydroxy group.	2.07	1	0	hydroxyindoles; phenols
methyl tryptophan, (l-trp)-isomer [no description available]	2.05	1	0
cryptolepine cryptolepine: fused indole-quinoline; structure in first source; from CRYPTOLEPIS sanguinolenta. cryptolepine : An organic heterotetracyclic compound that is 5H-indolo[3,2-b]quinoline in which the hydrogen at position N-5 is replaced by a methyl group.	2.05	1	0	indole alkaloid; organic heterotetracyclic compound; organonitrogen heterocyclic compound	anti-inflammatory agent; antimalarial; antineoplastic agent; cysteine protease inhibitor; plant metabolite
eriocitrin eriocitrin: structure in first source. eriocitrin : A disaccharide derivative that consists of eriodictyol substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.07	1	0	3'-hydroxyflavanones; 4'-hydroxyflavanones; disaccharide derivative; flavanone glycoside; rutinoside; trihydroxyflavanone	antioxidant
clarithromycin Clarithromycin: A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit PROTEIN SYNTHESIS in BACTERIA by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.. clarithromycin : The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment of peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.	2.11	1	0	macrolide antibiotic	antibacterial drug; environmental contaminant; protein synthesis inhibitor; xenobiotic
7,8-dihydromethysticin [no description available]	2.07	1	0	2-pyranones; aromatic ether
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	7.71	3	0	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
cinchonine [no description available]	2.47	2	0	(8xi)-cinchonan-9-ol; cinchona alkaloid	metabolite
aucubin [no description available]	2.07	1	0	organic molecular entity	metabolite
lupinine lupinine: RN given refers to parent cpd(1R-trans)-isomer; structure	2.07	1	0	quinolizidine alkaloid
matrine [no description available]	3.61	2	0	alkaloid
friedelin 3-friedelanone: from the stem bark of Irvingia gabonensis; structure in first source. friedelin : A pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork.	2.07	1	0	cyclic terpene ketone; pentacyclic triterpenoid	anti-inflammatory drug; antipyretic; non-narcotic analgesic; plant metabolite
catalpol [no description available]	2.07	1	0	organic molecular entity	metabolite
quinine hydrochloride [no description available]	2.07	1	0
deacetyldiltiazem deacetyldiltiazem: metabolite of diltiazem; RN given refers to (cis-(+-))-isomer	2.07	1	0	benzothiazepine
sarsasapogenin [no description available]	2.07	1	0	sapogenin
iodosobenzene iodosobenzene: oxygen donor	2.05	1	0
n-hexadecyl-n,n-dimethyl-3-ammonio-1-propanesulfonate [no description available]	2.05	1	0
corynanthine Corynanthine: A stereoisomer of yohimbine.	2.07	1	0	yohimban alkaloid
brexanolone brexanolone: a mixture of allopregnanolone and sulfobutylether‐beta‐cyclodextrin for treatment of postpartum depression. brexanolone : A 3-hydroxy-5alpha-pregnan-20-one in which the hydroxy group at position 3 has alpha-configuration. It is a metabolite of the sex hormone progesterone and used for the treatment of postpartum depression in women.	3.51	1	0	3-hydroxy-5alpha-pregnan-20-one	antidepressant; GABA modulator; human metabolite; intravenous anaesthetic; sedative
prunin protein, prunus prunin protein, Prunus: a legumin-like type of globulin; structure given in first source. naringenin 7-O-beta-D-glucoside : A flavanone 7-O-beta-D-glucoside that is (S)-naringenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.07	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; flavanone 7-O-beta-D-glucoside; monosaccharide derivative	antibacterial agent; antilipemic drug; hypoglycemic agent; metabolite
podocarpic acid podocarpic acid: structure. podocarpic acid : An abietane diterpenoid lacking the isopropyl substituent with an aromatic C-ring and a hydroxy group at the 12-position.	2.07	1	0	abietane diterpenoid
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	2.1	1	0
dehydroabietic acid dehydroabietic acid: major aquatic toxicant in effluent of pulp and paper mills. dehydroabietic acid : An abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group.. dehydroabietate : A monocarboxylic acid anion that is the conjugate base of dehydroabietic acid, obtained by deprotonation of the carboxy group.	2.15	1	0	abietane diterpenoid; carbotricyclic compound; monocarboxylic acid	allergen; metabolite
harmol hydrochloride [no description available]	2.07	1	0
5-Methoxyflavone 5-methoxyflavone: DNA polymerase-beta inhibitor and neuroprotective agent against beta-amyloid toxicity; structure in first source	2.07	1	0	ether; flavonoids
desethylchloroquine desethylchloroquine: metabolite of chloroquine	2.05	1	0	aminoquinoline
10-hydroxycamptothecin [no description available]	2.07	1	0	pyranoindolizinoquinoline
phellopterin phellopterin: a naturally occurring furanocoumarin found in roots of Angelica dahurica; structure in first source	2.17	1	0	psoralens
quindoline quindoline: a fused indole-quinoline alkaloid from CRYPTOLEPIS sanguinolenta; structure	2.17	1	0
n-(2-carboxyphenyl)phenoxyacetamide N-(2-carboxyphenyl)phenoxyacetamide: structure	3.51	1	0
nimbolide nimbolide: isolated from Nigerian medicinal plant Azadirachta indica; RN given refers to 4alpha,5alpha,6alpha,7alpha,15beta,17alpha-isomer; structure given in first source	7.6	1	0
wr 159412 [no description available]	2.05	1	0
corydaline [no description available]	2.07	1	0	isoquinoline alkaloid; isoquinolines
demissidine [no description available]	2.07	1	0	alkaloid; organic heteropolycyclic compound; steroid
cinchonidine cinchonidine: has antimalarial activity; diastereoisomer of cinchonine with distinct physiochemical properties; RN given refers to parent cpd(8alpha,9R)-isomer. cinchonidine : 8-epi-Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (R configuration). A diasteroisomer of cinchonine, it occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis.	2.47	2	0	(8xi)-cinchonan-9-ol; cinchona alkaloid	metabolite
benzyloxyamine benzyloxyamine: RN given refers to parent cpd	2.05	1	0
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	7.02	1	0	cobalt group element atom; metal allergen	micronutrient
imipenem, anhydrous Imipenem: Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with CILASTATIN, a renal dipeptidase inhibitor.. imipenem : A broad-spectrum, intravenous beta-lactam antibiotic of the carbapenem subgroup.	2.6	1	0	beta-lactam antibiotic allergen; carbapenems; zwitterion	antibacterial drug
sr141716 [no description available]	2	1	0	amidopiperidine; carbohydrazide; dichlorobenzene; monochlorobenzenes; pyrazoles	anti-obesity agent; appetite depressant; CB1 receptor antagonist
propidium iodide [no description available]	2.07	1	0	organic iodide salt
indoxacarb indoxacarb: oxadiazine insecticide; structure in first source. insecticide : Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	3.15	1	0	methyl ester; organochlorine insecticide	voltage-gated sodium channel blocker
pyronaridine [no description available]	2.05	1	0	aminoquinoline
tryptoline tryptoline: neurotoxic factor that may be involved in development of Parkinson's disease; enzymatic prep from human brain converts tryptamine to tryptoline; RN given refers to parent cpd; structure	2.52	2	0	beta-carbolines
procyanidin Proanthocyanidins: Dimers and oligomers of flavan-3-ol units (CATECHIN analogs) linked mainly through C4 to C8 bonds to leucoanthocyanidins. They are structurally similar to ANTHOCYANINS but are the result of a different fork in biosynthetic pathways.	3.21	1	0	proanthocyanidin
deguelin deguelin: a natural product from Mundulea sericea; RN refers to (7aS-cis)-isomer; structure given in first source. deguelin : A rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers.	2.07	1	0	aromatic ether; diether; organic heteropentacyclic compound; rotenones	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; mitochondrial NADH:ubiquinone reductase inhibitor; plant metabolite
catechin (+)-catechin monohydrate : The monohydrate of (+)-catechin.	2.07	1	0	hydrate	geroprotector
daidzin daidzin: a potent, selective, and reversible inhibitor of human mitochondrial aldehyde dehydrogenase. daidzein 7-O-beta-D-glucoside : A glycosyloxyisoflavone that is daidzein attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It is used in the treatment of alcohol dependency (antidipsotropic).	2.07	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; monosaccharide derivative	plant metabolite
cafestol [no description available]	2.07	1	0	diterpenoid; furans; organic heteropentacyclic compound; primary alcohol; tertiary alcohol	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; hypoglycemic agent; plant metabolite
parthenolide [no description available]	2.07	1	0	germacranolide
sphondin sphondin: from Heracleum laciniatum; cause of phototoxicity in patient with vitiligo	2.17	1	0	furanocoumarin
ecteinascidin 743 [no description available]	3.25	1	0	acetate ester; azaspiro compound; bridged compound; hemiaminal; isoquinoline alkaloid; lactone; organic heteropolycyclic compound; organic sulfide; oxaspiro compound; polyphenol; tertiary amino compound	alkylating agent; angiogenesis modulating agent; anti-inflammatory agent; antineoplastic agent; marine metabolite
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	2.1	1	0
anserine Anserine: A dipeptide containing BETA-ALANINE.. anserine : A dipeptide comprising of beta-alanine and 3-methyl-L-histidine units.	2.41	1	0	beta-alanine derivative; dipeptide; zwitterion	animal metabolite; mouse metabolite
homoorientin homoorientin: isolated from Swertia japonica; structure given in first source	2.07	1	0	flavone C-glycoside; tetrahydroxyflavone	antineoplastic agent; radical scavenger
thromboxanes thromboxane : A class of oxygenated oxane derivatives, originally derived from prostaglandin precursors in platelets, that stimulate aggregation of platelets and constriction of blood vessels.	2.05	1	0
pumiliotoxin c pumiliotoxin C: isolated from skin of Dendrobates pumilio (frog); see also records for pumiliotoxin A, pumiliotoxin B & pumiliotoxins	2.17	1	0
ginkgolide a [no description available]	2.21	1	0	diterpene lactone
tafenoquine tafenoquine : A racemate comprising equimolar amounts of (R)- and (S)-tafenoquine.. N(4)-{2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl}pentane-1,4-diamine : An aminoquinoline that is 8-aminoquinoline which is substituted by methoxy groups at positions 2 and 6, a methyl group at position 4, and a m-(trifluoromethyl)phenoxy group at position 5, and in which the amino substituent at position 8 is itself substituted by a 5-aminopentan-2-yl group.	2.05	1	0	(trifluoromethyl)benzenes; aminoquinoline; aromatic ether; primary amino compound; secondary amino compound
asiatic acid [no description available]	2.55	2	0	monocarboxylic acid; pentacyclic triterpenoid; triol	angiogenesis modulating agent; metabolite
ginsenoside rh2 ginsenoside Rh2: from leaves of Panax ginseng C; structure given in first source. (20S)-ginsenoside Rh2 : A ginsenoside found in Panax species that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-S positions, in which the hydroxy group at position 3 has been converted to the corresponding beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position.	7.17	1	0	12beta-hydroxy steroid; 20-hydroxy steroid; beta-D-glucoside; ginsenoside; tetracyclic triterpenoid	antineoplastic agent; apoptosis inducer; bone density conservation agent; cardioprotective agent; hepatoprotective agent; plant metabolite
angustmycin a angustmycin A: structure; from Streptomyces hygroscopicus; inhibits GMP synthesis	2.07	1	0	6-aminopurines
razadyne Razadyne: Name of the FDA approved preparation from J&J.	2.07	1	0
desethylamodiaquine desethylamodiaquine: metabolite of amodiaquine	2.05	1	0
diazaquinomycin a diazaquinomycin A: structure given in first source	2.17	1	0	quinolone
phytosphingosine phytosphingosine: differ with an additional hydroxyl at C-4 & no double bond between C-4 & C-5	2.07	1	0	amino alcohol; sphingoid; triol	mouse metabolite; Saccharomyces cerevisiae metabolite
butyryl-coenzyme a [no description available]	2.06	1	0	butanoyl-CoAs	Escherichia coli metabolite; mouse metabolite
tetradecanoylphorbol acetate [no description available]	2.07	1	0
n,n-dideethylchloroquine [no description available]	2.05	1	0
celastrol [no description available]	2.5	2	0	monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory drug; antineoplastic agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Hsp90 inhibitor; metabolite
4'-demethylepipodophyllotoxin 4'-demethylepipodophyllotoxin: structure in first source. 4'-demethylepipodophyllotoxin : An organic heterotetracyclic compound that is the 9- epimer of 4'-demethylpodophyllotoxin.	2.07	1	0	furonaphthodioxole; organic heterotetracyclic compound; phenols	antineoplastic agent
n-(n-(3-carboxyoxirane-2-carbonyl)leucyl)isoamylamine N-(N-(3-carboxyoxirane-2-carbonyl)leucyl)isoamylamine: inhibits calcium-activated neutral protease; see also record for E-64; RN given refers to (2-S-(2alpha,3beta)(R*)-isomer)	2.07	1	0	leucine derivative
methyl 4-mercaptobutyrimidate methyl 4-mercaptobutyrimidate: used as a cross-linking agent to study ribosomal proteins, by making disulfide linkages; RN given refers to parent cpd; structure	2.13	1	0	organonitrogen compound; oxoacid derivative
e 64 E 64: cysteine protease inhibitor of microbial origin, which inhibits cathepsin B (EC 3.4.22.1) and cathepsin L (EC 3.4.22.-)	2.07	1	0	dicarboxylic acid monoamide; epoxy monocarboxylic acid; guanidines; L-leucine derivative; zwitterion	antimalarial; antiparasitic agent; protease inhibitor
fraxinellone fraxinellone: structure given in first source; RN given for (3R-cis)-isomer	2.17	1	0	2-benzofurans
glabridin [no description available]	2.17	1	0	hydroxyisoflavans	antiplasmodial drug
3,6-diamino-9-(4-(methylsulfonyl)aminophenyl)aminoacridine [no description available]	2.05	1	0
cgp 361a isamoltane: structure given in first source	2.06	1	0
ne 58051 NE 58051: inhibits tumor cell adhesion to extracellular matrices; structure in first source	2.05	1	0
safinamide safinamide: short-acting inhibitor of MOA-B; FCE 26743 is (S)-isomer, FCE 28073 is (R)-isomer; structure in first source	2.25	1	0	amino acid amide
6-bromo-3-(bromomethyl)-7-methyl-2,3,7-trichloro-1-octene 6-bromo-3-(bromomethyl)-7-methyl-2,3,7-trichloro-1-octene: structure given in first source	2.17	1	0	monoterpenoid; organobromine compound; organochlorine compound	algal metabolite; antineoplastic agent; marine metabolite
3,5-bis(trifluoromethyl)benzyl n-acetyltryptophan 3,5-bis(trifluoromethyl)benzyl N-acetyltryptophan: structure given in first source; substance P and neurokinin receptor antagonist	2.03	1	0
5'-(sulfonylbenzoyl)adenosine 5'-(sulfonylbenzoyl)adenosine: covalently binds to platelet membrane	3.25	1	0
wr 242511 WR 242511: RN given refers to parent cpd	2.05	1	0
sinensetin sinensetin: isolated from citrus fruit; exhibit antiadhesive action on platelets. sinensetin : A pentamethoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 3' and 4' respectively.	2.07	1	0	pentamethoxyflavone	plant metabolite
harmalol hydrochloride [no description available]	2.07	1	0
1-(1,3-benzodioxol-5-yl)-3-(1-piperidinyl)-1-propanone [no description available]	2.07	1	0	benzodioxoles
docetaxel [no description available]	2.11	1	0	hydrate; secondary alpha-hydroxy ketone	antineoplastic agent
docetaxel anhydrous Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.	3.04	4	0	secondary alpha-hydroxy ketone; tetracyclic diterpenoid	antimalarial; antineoplastic agent; photosensitizing agent
3,3,5,5-tetramethyl-1-pyrroline n-oxide [no description available]	1.99	1	0
5-hydroxy-3',4',6,7-tetramethoxyflavone 5-hydroxy-3',4',6,7-tetramethoxyflavone: isolated from Artemisia argyi	2.17	1	0
hyoscyamine Hyoscyamine: The 3(S)-endo isomer of atropine.. (S)-atropine : An atropine with a 2S-configuration.	2.07	1	0	tropane alkaloid
schizandrin a schizandrin A: the major lignan, 2-9%, of Schisandra plant; has hepatoprotective, antioxidant, and antineoplastic activities	2.48	2	0
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	2.05	1	0	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	2	1	0	oxygen hydride; oxygen radical; reactive oxygen species
pseudonicotine pseudonicotine: structure. (R)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has R-configuration.	2.17	1	0	3-(1-methylpyrrolidin-2-yl)pyridine
schizandrin b (+)-schisandrin B : An organic heterotetracyclic compound that is found in Fructus Schisandrae and Schisandra chinensis.	2.07	1	0	aromatic ether; cyclic acetal; organic heterotetracyclic compound; oxacycle; tannin	anti-asthmatic agent; anti-inflammatory agent; antilipemic drug; antioxidant; apoptosis inhibitor; hepatoprotective agent; nephroprotective agent; neuroprotective agent; plant metabolite
camphora camphora: a component of Guanxingao, a kind of traditional Chinese rubber electuary medicine which is able to either cure or guard against coronary heart disease and angina pectoris. (R)-camphor : The (R)- enantiomer of camphor.	3.12	1	0	camphor
rhodioloside [no description available]	2.05	1	0	glycoside
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	2.05	1	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
cryptotanshinone cryptotanshinone: from Salvia miltiorrhiza	2.07	1	0	abietane diterpenoid	anticoronaviral agent
cyc 202 seliciclib : 2,6-Diaminopurine carrying benzylamino, (2R)-1-hydroxybutan-2-yl and isopropyl substituents at C-6, C-2-N and N-9 respectively. It is an experimental drug candidate in the family of pharmacological cyclin-dependent kinase (CDK) inhibitors.	2.05	1	0	2,6-diaminopurines	antiviral drug; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
isosakuranetin isosakuranetin: structure in first source. 4'-methoxy-5,7-dihydroxyflavanone : A dihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5 and 7 and a methoxy group at position 4' (the 2S stereoisomer).	2.07	1	0	(2S)-flavan-4-one; 4'-methoxyflavanones; dihydroxyflavanone; monomethoxyflavanone	plant metabolite
deferrioxamine e deferrioxamine E: may act as siderophore in Streptomyces. desferrioxamine E : A cyclic hydroxamic acid siderophore that is produced by several bacterial species and exhibits antitumour activity.	2.17	1	0	cyclic desferrioxamine; cyclic hydroxamic acid; macrocycle	antineoplastic agent; bacterial metabolite; marine metabolite; siderophore
ag 3-5 icilin: a cooling compound that activates TRPM8	3.12	1	0	C-nitro compound
isovitexin [no description available]	2.07	1	0	C-glycosyl compound; trihydroxyflavone	EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
sclareol sclareol: structure given in first source. sclareol : A labdane diterpenoid that is labd-14-ene substituted by hydroxy groups at positions 8 and 13. It has been isolated from Salvia sclarea.	2.07	1	0	labdane diterpenoid	antifungal agent; antimicrobial agent; apoptosis inducer; fragrance; plant metabolite
tanshinone ii a tashinone IIA: a cardiovascular agent with antineoplastic activity; isolated from Salvia miltiorrhiza; structure in first source	2.07	1	0	abietane diterpenoid
4'-hydroxyflavanone 4'-hydroxyflavanone: structure in first source. 4'-hydroxyflavanones : Any hydroxyflavanone having a hydroxy substituent located at position 4'.	2.17	1	0	4'-hydroxyflavanones; monohydroxyflavanone
leucodin leucodin: structure in first source	2.07	1	0	sesquiterpene lactone
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	2.15	1	0	amino acid zwitterion; angiotensin II	human metabolite
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	3.15	5	0
sb 203580 [no description available]	2.54	2	0	imidazoles; monofluorobenzenes; pyridines; sulfoxide	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector; Hsp90 inhibitor; neuroprotective agent
limonin [no description available]	3.59	2	0	epoxide; furans; hexacyclic triterpenoid; lactone; limonoid; organic heterohexacyclic compound	inhibitor; metabolite; volatile oil component
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	3.25	6	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
deflazacort deflazacort: structure	2.05	1	0	corticosteroid hormone
maduramicin maduramicin: isolated from Actinomadura rubra	2.07	1	0
chelidonine chelidonine: benzophenanthridine derived from scoulerine from Chelidonium majus; RN given refers to parent cpd (chelidonine, (5bR-(5balpha,6beta,12alpha))-isomer)	2.07	1	0	alkaloid antibiotic; alkaloid fundamental parent; benzophenanthridine alkaloid
olpadronic acid [no description available]	2.05	1	0
troleandomycin Troleandomycin: A macrolide antibiotic that is similar to ERYTHROMYCIN.. troleandomycin : A semi-synthetic macrolide antibiotic obtained by acetylation of the three free hydroxy groups of oleandomycin. Troleandomycin is only found in individuals that have taken the drug.	2.07	1	0	acetate ester; epoxide; macrolide antibiotic; monosaccharide derivative; polyketide; semisynthetic derivative	EC 1.14.13.97 (taurochenodeoxycholate 6alpha-hydroxylase) inhibitor; xenobiotic
darunavir Darunavir: An HIV PROTEASE INHIBITOR that is used in the treatment of AIDS and HIV INFECTIONS. Due to the emergence of ANTIVIRAL DRUG RESISTANCE when used alone, it is administered in combination with other ANTI-HIV AGENTS.. darunavir : An N,N-disubstituted benzenesulfonamide bearing an unsubstituted amino group at the 4-position, used for the treatment of HIV infection. A second-generation HIV protease inhibitor, darunavir was designed to form robust interactions with the protease enzyme from many strains of HIV, including those from treatment-experienced patients with multiple resistance mutations to other protease inhibitors.	2.17	1	0	carbamate ester; furofuran; sulfonamide	antiviral drug; HIV protease inhibitor
sorafenib [no description available]	7.6	1	0	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; phenylureas; pyridinecarboxamide	angiogenesis inhibitor; anticoronaviral agent; antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; ferroptosis inducer; tyrosine kinase inhibitor
santonin Santonin: Anthelmintic isolated from the dried unexpanded flower heads of Artemisia maritima and other species of Artemisia found principally in Russian and Chinese Turkestan and the Southern Ural region. (From Merck, 11th ed.)	2.07	1	0	botanical anti-fungal agent; santonin	plant metabolite
sandaracopimaric acid sandaracopimaric acid: a terpenoid from Sagittaria sanittifolia L.. sandaracopimaric acid : A pimarane diterpenoid that is (1S,4aS,4bS,7R,10aS)-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene carrying a carboxy group at position 1 and a vinyl group at position 7. It is a natural product found in several plant species.	2.15	1	0	monocarboxylic acid; pimarane diterpenoid; tricyclic diterpenoid	plant metabolite
sitosterol, (3beta)-isomer Sobatum: tradename; active fraction of Solanum trilobatum; reduces side-effects of radiation-induced toxicity. sitosterol : A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3.	2.07	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C29-steroid; phytosterols; stigmastane sterol	anticholesteremic drug; antioxidant; mouse metabolite; plant metabolite; sterol methyltransferase inhibitor
aspidospermine aspidospermine: an indole fused to a qunoline; isolated from Aspidosperma tree; structure given in first source. aspidospermine : An indole alkaloid having the structure of aspirospermidine methoxylated at C-17 and acetylated at N-1.	2.04	1	0	indole alkaloid
vincristine sulfate [no description available]	2.07	1	0	organic sulfate salt	antineoplastic agent; geroprotector
anisomycin Anisomycin: An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.. (-)-anisomycin : An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.	2.43	2	0	monohydroxypyrrolidine; organonitrogen heterocyclic antibiotic	anticoronaviral agent; antimicrobial agent; antineoplastic agent; antiparasitic agent; bacterial metabolite; DNA synthesis inhibitor; protein synthesis inhibitor
estramustine Estramustine: A nitrogen mustard linked to estradiol, usually as phosphate; used to treat prostatic neoplasms; also has radiation protective properties.. estramustine : A carbamate ester obtained by the formal condensation of the hydroxy group of 17beta-estradiol with the carboxy group of bis(2-chloroethyl)carbamic acid.	2.05	1	0	17beta-hydroxy steroid; carbamate ester; organochlorine compound	alkylating agent; antineoplastic agent; radiation protective agent
lupeol [no description available]	2.5	2	0	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory drug; plant metabolite
metribolone Metribolone: A synthetic non-aromatizable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.. 17beta-hydroxy-17-methylestra-4,9,11-trien-3-one : A synthetic non-aromatisable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.	2.11	1	0	17beta-hydroxy steroid; 3-oxo steroid; anabolic androgenic steroid	androgen
acetylstrophanthidin acetylstrophanthidin: structure. acetylstrophanthidin : An acetate ester that is strophanidin acetylated at the 3beta-hydroxy group.	2.07	1	0	acetate ester	anti-arrhythmia drug
withaferin a withaferin A: an antiestrogen and phytogenic antineoplastic agent isolated from leaves of Withania somnifera Dun.; structure. withaferin A : A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity.	4.07	2	1	27-hydroxy steroid; 4-hydroxy steroid; delta-lactone; enone; epoxy steroid; ergostanoid; primary alcohol; secondary alcohol; withanolide	antineoplastic agent; apoptosis inducer
noscapine Noscapine: A naturally occurring opium alkaloid that is a centrally acting antitussive agent.. (-)-noscapine : A benzylisoquinoline alkaloid that is 1,2,3,4-tetrahydroisoquinoline which is substituted by a 4,5-dimethoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl group at position 1, a methylenedioxy group at positions 6-7 and a methoxy group at position 8. Obtained from plants of the Papaveraceae family, it lacks significant painkilling properties and is primarily used for its antitussive (cough-suppressing) effects.	7.31	1	0	aromatic ether; benzylisoquinoline alkaloid; cyclic acetal; isobenzofuranone; organic heterobicyclic compound; organic heterotricyclic compound; tertiary amino compound	antineoplastic agent; antitussive; apoptosis inducer; plant metabolite
Harringtonine harringtonin: alkaloid C from Caphalotaxus fortunei	2.07	1	0	alkaloid
homoharringtonine Homoharringtonine: Semisynthetic derivative of harringtonine that acts as a protein synthesis inhibitor and induces APOPTOSIS in tumor cells. It is used in the treatment of MYELOID LEUKEMIA, CHRONIC.. omacetaxine mepesuccinate : A cephalotaxine-derived alkaloid ester obtained from Cephalotaxus harringtonia; used for the treatment of chronic or accelerated phase chronic myeloid leukaemia.	2.11	1	0	alkaloid ester; enol ether; organic heteropentacyclic compound; tertiary alcohol	anticoronaviral agent; antineoplastic agent; apoptosis inducer; protein synthesis inhibitor
acivicin [no description available]	2.07	1	0	isoxazoles; non-proteinogenic L-alpha-amino acid; organochlorine compound	antileishmanial agent; antimetabolite; antimicrobial agent; antineoplastic agent; EC 2.3.2.2 (gamma-glutamyltransferase) inhibitor; glutamine antagonist; metabolite
ketopinic acid ketopinic acid: structure in first source	2.07	1	0
wortmannin [no description available]	2.07	1	0	acetate ester; cyclic ketone; delta-lactone; organic heteropentacyclic compound	anticoronaviral agent; antineoplastic agent; autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector; Penicillium metabolite; radiosensitizing agent
2-oxindole 2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.	2.25	1	0	gamma-lactam; indolinone
withanolides Withanolides: Ergostane derivatives of 28 carbons with oxygens at C1, C22, and C26 positions and the side chain cyclized. They are found in WITHANIA plant genus and have cytotoxic and other effects.	3.99	1	1
gitoxigenin gitoxigenin: structure	2.07	1	0	14beta-hydroxy steroid; 16beta-hydroxy steroid; 3beta-hydroxy steroid
graveoline graveoline: structure in first source	2.07	1	0	quinolines
3-(2-Methylpropanoyloxy)-8-(2-methylbutanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene [no description available]	3.51	1	0	benzoate ester; phenols
4-oxy-6-(4-oxybezoyloxy)dauc-8,9-en 4-oxy-6-(4-oxybezoyloxy)dauc-8,9-en: RN given for (3R-(3alpha,3abeta,4beta,8aalpha))-isomer; a natural benzyl ester of a carotyl type azulene sesquiterpenoid; structure in first source	2.07	1	0
phyllanthin [no description available]	7.11	1	0	lignan
neocryptolepine neocryptolepine: isolated from the roots of the African plant Cryptolepis sanguinolenta; structure in first source	2.05	1	0
calcein am calcein AM: a non-fluorescent compound cleaved to a fluorescent compound by non-specific intracellular esterases. calcein am : An organic heteropentacyclic compound that is calcein in which all four carboxy group hydrogens have been substituted by (acetyloxy)methoxy groups and the hyrodgens of the two hydroxy groups have been substituted by acetyl groups. It is a a non-fluorescent probe cleaved to a fluorescent probe by non-specific intracellular esterases.	2.17	1	0	2-benzofurans; acetate ester; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; xanthene dye	fluorochrome
crinine crinine: structure in first source	2.17	1	0	alkaloid
1-hydroxypentane-1,1-bisphosphonate [no description available]	2.05	1	0
cimadronate cimadronate: increases serum 1,25-dihydroxyvitamin D in rats via stimulating renal 1-hydroxylase activity; structure given in first source	2.05	1	0
1,1-hydroxyoctanodiphosphonate [no description available]	2.05	1	0
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	3.38	2	0
n-acetylneuraminic acid N-Acetylneuraminic Acid: An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518). N-acetylneuraminic acid : An N-acylneuraminic acid where the N-acyl group is specified as acetyl.	2.42	2	0	N-acetylneuraminic acids	antioxidant; bacterial metabolite; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; human metabolite; mouse metabolite
elastin [no description available]	2.05	1	0	oligopeptide
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	2.52	2	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
oxytocin Oxytocin: A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION.. oxytocin : A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour.	2.05	1	0	heterodetic cyclic peptide; peptide hormone	oxytocic; vasodilator agent
theanine theanine: RN given refers to (L)-isomer; precursor of ethylamine; found in green tea. N(5)-ethyl-L-glutamine : A N(5)-alkylglutamine where the alkyl group is ethyl. It has been isolated from green tea.	3.17	1	0	amino acid zwitterion; N(5)-alkyl-L-glutamine	geroprotector; neuroprotective agent; plant metabolite
ouabain Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.	2.41	2	0	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
puromycin [no description available]	2.07	1	0	puromycins	antiinfective agent; antimicrobial agent; antineoplastic agent; EC 3.4.11.14 (cytosol alanyl aminopeptidase) inhibitor; EC 3.4.14.2 (dipeptidyl-peptidase II) inhibitor; nucleoside antibiotic; protein synthesis inhibitor
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	2.07	1	0	taxifolin	metabolite
mimosine L-mimosine : An L-alpha-amino acid that is propionic acid substituted by an amino group at position 2 and a 3-hydroxy-4-oxopyridin-1(4H)-yl group at position 3 (the 2S-stereoisomer). It a non-protein plant amino acid isolated from Mimosa pudica.	2.07	1	0	4-pyridones; amino acid zwitterion; non-proteinogenic L-alpha-amino acid	EC 1.14.18.1 (tyrosinase) inhibitor; plant metabolite
eriodictyol eriodictyol: structure. eriodictyol : A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' respectively.	2.54	2	0	3'-hydroxyflavanones; tetrahydroxyflavanone
arbutin hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.	2.07	1	0	beta-D-glucoside; monosaccharide derivative	Escherichia coli metabolite; plant metabolite
strychnine Strychnine: An alkaloid found in the seeds of STRYCHNOS NUX-VOMICA. It is a competitive antagonist at glycine receptors and thus a convulsant. It has been used as an analeptic, in the treatment of nonketotic hyperglycinemia and sleep apnea, and as a rat poison.. strychnine : A monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position.	2.58	2	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
quinidine Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.	3.87	3	0	cinchona alkaloid	alpha-adrenergic antagonist; anti-arrhythmia drug; antimalarial; drug allergen; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; muscarinic antagonist; P450 inhibitor; potassium channel blocker; sodium channel blocker
conessine conessine : A steroid alkaloid that is con-5-enine substituted by a N,N-dimethylamino group at position 3. It has been isolated from the plant species of the family Apocynaceae.	2.46	2	0	steroid alkaloid; tertiary amino compound	antibacterial agent; antimalarial; H3-receptor antagonist; plant metabolite
griseofulvin Griseofulvin: An antifungal agent used in the treatment of TINEA infections.. griseofulvin : An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.	2.07	1	0	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite
digitoxin Digitoxin: A cardiac glycoside sometimes used in place of DIGOXIN. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665). digitoxin : A cardenolide glycoside in which the 3beta-hydroxy group of digitoxigenin carries a 2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl trisaccharide chain.	2.47	2	0	cardenolide glycoside	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
hyperforin hyperforin: a prenylated acylphloroglucinol derivative; antibiotic component of novoimanine; psychoactive agent in St. John's wort; Russian; structure;. hyperforin : A cyclic terpene ketone that is a prenylated carbobicyclic acylphloroglucinol derivative produced by St. John's Wort, Hypericum perforatum.	2.07	1	0
canaline canaline: structure	2.05	1	0	amino acid zwitterion; non-proteinogenic L-alpha-amino acid	antimetabolite; antineoplastic agent; phytogenic insecticide; plant metabolite
deltaline [no description available]	2.07	1	0	acetate ester; cyclic acetal; diterpene alkaloid; organic polycyclic compound; tertiary alcohol; tertiary amino compound
columbin columbin: from Tinospora Cordifolia Miers & Calumbae Radix (the root of Jateorhiza columba MIERS, Menispermacea) ; structure given in first source	7.6	1	0	organic heterotricyclic compound; organooxygen compound
ingenol [no description available]	2.07	1	0	cyclic terpene ketone; tetracyclic diterpenoid
micheliolide micheliolide: has antineoplastic activity; structure in first source	2.17	1	0	sesquiterpene lactone
picrotin picrotin: the less toxic component of PICROTOXIN lacking GABA activity. picrotin : An organic heteropentacyclic compound that is picrotoxinin in which the olefinic double bond has undergone addition of water to give the corresponding tertiary alcohol. It is the less toxic component of picrotoxin, lacking GABA activity.	2.07	1	0	diol; epoxide; gamma-lactone; organic heteropentacyclic compound; picrotoxane sesquiterpenoid; tertiary alcohol	plant metabolite
picrotoxinin [no description available]	2.07	1	0	epoxide; gamma-lactone; organic heteropentacyclic compound; picrotoxane sesquiterpenoid; tertiary alcohol	GABA antagonist; plant metabolite; serotonergic antagonist
naringin [no description available]	3.59	2	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
isonaringin isonaringin: structure in first source. narirutin : A disaccharide derivative that is (S)-naringenin substituted by a 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.07	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; rutinoside	anti-inflammatory agent; antioxidant; metabolite
ochratoxin a ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.	2.46	2	0	isochromanes; monocarboxylic acid amide; N-acyl-L-phenylalanine; organochlorine compound; phenylalanine derivative	Aspergillus metabolite; calcium channel blocker; carcinogenic agent; mycotoxin; nephrotoxin; Penicillium metabolite; teratogenic agent
gingerol gingerol: an active ingredient in GINGER along with SHOGAOL. a nonvolatile methoxy phenyl decanone. gingerol : A beta-hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4-hydroxy-3-methoxyphenyl moiety at position 1; believed to inhibit adipogenesis. It is a constituent of fresh ginger.	4.96	6	0	beta-hydroxy ketone; guaiacols	antineoplastic agent; plant metabolite
securinine securinine: a quinolizine pseudoalkaloid (not from amino acid) from Securinega suffurutiosa or Securinini nitras	2.07	1	0	indolizines
Dubinidine [no description available]	2.07	1	0	organic heterotricyclic compound; organonitrogen heterocyclic compound; oxacycle
cyclopamine [no description available]	2.07	1	0	piperidines	glioma-associated oncogene inhibitor
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	3.2	5	0
pancracine pancracine: structure in first source	2.17	1	0	isoquinoline alkaloid fundamental parent; isoquinoline alkaloid
doxorubicin hydrochloride [no description available]	2.07	1	0	anthracycline
vinpocetine vinpocetine: whole issue of Arzneim Forsch (23 articles) discuss this drug; Arzneim Forsch 26(10a);1976; RN given refers to parent cpd with unspecified isomeric designation	2.07	1	0	alkaloid	geroprotector
dihydroergocristine monomesylate dihydroergocristine mesylate : The methanesulfonic acid salt of dihydroergocristine. It has been used as the for the symptomatic treatment of mental deterioration associated with cerebrovascular insufficiency and in peripheral vascular disease. It is also a component of ergoloid mesylate (codergocrine mesilate), a mixture of ergot alkaloid derivatives that is used as a vasodilator and has shown mild benefits in the treatment of vascular dementia.	2.07	1	0	methanesulfonate salt	alpha-adrenergic antagonist; geroprotector; vasodilator agent
fluticasone propionate fluticasone propionate : A trifluorinated corticosteroid that consists of 6alpha,9-difluoro-11beta,17alpha-dihydroxy-17beta-{[(fluoromethyl)sulfanyl]carbonyl}-16-methyl-3-oxoandrosta-1,4-diene bearing a propionyl substituent at position 17; has anti-inflammatory, anti-asthmatic and anti-allergic activity.	2.11	1	0	11beta-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; corticosteroid; fluorinated steroid; propanoate ester; steroid ester; thioester	adrenergic agent; anti-allergic agent; anti-asthmatic drug; anti-inflammatory drug; bronchodilator agent; dermatologic drug
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.31	1	0	cyclodextrin
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2.55	2	0	cinnamic acid	plant metabolite
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	2.07	1	0	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	2.47	2	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	11	21	4	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
retinol Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).	3.17	1	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	7.8	3	0	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
pectins Pectins: High molecular weight polysaccharides present in the cell walls of all plants. Pectins cement cell walls together. They are used as emulsifiers and stabilizers in the food industry. They have been tried for a variety of therapeutic uses including as antidiarrheals, where they are now generally considered ineffective, and in the treatment of hypercholesterolemia.. alpha-D-galacturonic acid : The alpha-anomer of D-galacturonic acid.	2.9	2	0	D-galactopyranuronic acid
thapsigargin Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.	2.07	1	0	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
mycophenolic acid Mycophenolic Acid: Compound derived from Penicillium stoloniferum and related species. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase (IMP DEHYDROGENASE). Mycophenolic acid exerts selective effects on the immune system in which it prevents the proliferation of T-CELLS, LYMPHOCYTES, and the formation of antibodies from B-CELLS. It may also inhibit recruitment of LEUKOCYTES to sites of INFLAMMATION.. mycophenolate : A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of mycophenolic acid.. mycophenolic acid : A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mofetil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.	2.07	1	0	2-benzofurans; gamma-lactone; monocarboxylic acid; phenols	anticoronaviral agent; antimicrobial agent; antineoplastic agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; environmental contaminant; immunosuppressive agent; mycotoxin; Penicillium metabolite; xenobiotic
mupirocin Mupirocin: A topically used antibiotic from a strain of Pseudomonas fluorescens. It has shown excellent activity against gram-positive staphylococci and streptococci. The antibiotic is used primarily for the treatment of primary and secondary skin disorders, nasal infections, and wound healing.. mupirocin : An alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections.	2.06	1	0	alpha,beta-unsaturated carboxylic ester; epoxide; monocarboxylic acid; oxanes; secondary alcohol; triol	antibacterial drug; bacterial metabolite; protein synthesis inhibitor
lycopene [no description available]	4.08	1	0	acyclic carotene	antioxidant; plant metabolite
6-bromoindirubin-3'-oxime 6-bromoindirubin-3'-oxime: structure in first source. 6-bromoindirubin-3'-oxime : A member of the class of biindoles that is indirubin substituted at position 6 by a bromo group and in which the keto group at position 3' has undergone condensation with hydroxylamine to form the corresponding oxime.	3.31	1	0
alitretinoin Alitretinoin: A retinoid that is used for the treatment of chronic hand ECZEMA unresponsive to topical CORTICOSTEROIDS. It is also used to treat cutaneous lesions associated with AIDS-related KAPOSI SARCOMA.	2.07	1	0	retinoic acid	antineoplastic agent; keratolytic drug; metabolite; retinoid X receptor agonist
L-cycloserine L-cycloserine : A 4-amino-1,2-oxazolidin-3-one that has S configuration. An antibiotic isolated from Erwinia uredovora.	2.07	1	0	4-amino-1,2-oxazolidin-3-one	anti-HIV agent; anticonvulsant; EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor
12-deoxyphorbol 13-acetate [no description available]	2.07	1	0	phorbol ester	metabolite
purvalanol a 6-((3-chloro)anilino)-2-(isopropyl-2-hydroxyethylamino)-9-isopropylpurine: purvalanol A is the (1R)-isomer;	2.05	1	0	purvalanol
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	2.07	1	0	actinomycin	mutagen
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	2.63	2	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
aphidicolin Aphidicolin: An antiviral antibiotic produced by Cephalosporium aphidicola and other fungi. It inhibits the growth of eukaryotic cells and certain animal viruses by selectively inhibiting the cellular replication of DNA polymerase II or the viral-induced DNA polymerases. The drug may be useful for controlling excessive cell proliferation in patients with cancer, psoriasis or other dermatitis with little or no adverse effect upon non-multiplying cells.. aphidicolin : A tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication.	2.07	1	0	tetracyclic diterpenoid	antimicrobial agent; antimitotic; antineoplastic agent; antiviral drug; apoptosis inducer; Aspergillus metabolite; DNA synthesis inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; fungal metabolite
melphalan Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.	2.05	1	0	L-phenylalanine derivative; nitrogen mustard; non-proteinogenic L-alpha-amino acid; organochlorine compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
(+)-usnic acid [no description available]	2.07	1	0	usnic acid
beta, beta-dimethylacrylshikonin, (+)-isomer [no description available]	2.07	1	0	hydroxy-1,4-naphthoquinone
shikonin shikonin: a naphthazarin; has antineoplastic and angiogenesis inhibiting activities	2.07	1	0	hydroxy-1,4-naphthoquinone
vulgarone b vulgarone B: sesquiterpene ketone antifungal constituent in the steam-distilled fraction of Artemisia douglasiana; structure in first source	3.15	1	0
Tetrahydropiperine [no description available]	3.3	6	0	benzodioxoles
carbenoxolone [no description available]	2.05	1	0
piperyline piperyline: amide alkaloid isolated from P. nigrum. piperyline : A N-acylpyrrolidine that is pyrollidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum.	3.63	2	0	benzodioxoles; N-acylpyrrolidine; pyrrolidine alkaloid; tertiary carboxamide	antifungal agent; apoptosis inducer; plant metabolite
rhapontin rhapontin: constituent of rhubarb rhizome	2.07	1	0	rhaponticin	angiogenesis inhibitor; anti-allergic agent; anti-inflammatory agent; antilipemic drug; antineoplastic agent; apoptosis inducer; EC 2.3.1.85 (fatty acid synthase) inhibitor; hypoglycemic agent; neuroprotective agent; plant metabolite
cinnamaldehyde 3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.	11.73	9	0	3-phenylprop-2-enal; cinnamaldehydes	antifungal agent; EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor; flavouring agent; hypoglycemic agent; plant metabolite; sensitiser; vasodilator agent
glycosides [no description available]	2.47	2	0
chalcone trans-chalcone : The trans-isomer of chalcone.	2.06	1	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
piplartine piplartine: Antineoplastic Agent, Phytogenic; alkaloid from Piper; structure in first source	5.95	18	0	cinnamamides; dicarboximide
citral citral: Xref geranial: geraniol is also available; Xref neral: nerol is also available; vitamin A antagonist; oxygenated monoterpene; inhibits cytosolic dehydrogenases; structure. citral : An enal that consists of octa-2,6-dienal bearing methyl substituents at positions 3 and 7. A mixture of the two geometric isomers geranial and neral, it is the major constituent (75-85%) of oil of lemon grass, the volatile oil of Cymbopogon citratus, or of C. flexuosus. It also occurs in oils of verbena, lemon, and orange.	4.21	2	0	enal; monoterpenoid; polyprenal	plant metabolite; volatile oil component
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	9.67	13	3	stilbene
antofine antofine: structure in first source. (-)-antofine : An organic heteropentacyclic compound that is (13aR)-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline substituted at positions 2, 3 and 6 by methoxy groups. It is an alkaloid produced by relatives of the milkweed family and exhibits antiviral, anti-inflammatory, antiadipogenic and antitumorigenic activities.	3.25	1	0	alkaloid antibiotic; alkaloid; aromatic ether; organic heteropentacyclic compound	angiogenesis inhibitor; anti-inflammatory agent; antimicrobial agent; antineoplastic agent; antiviral agent; phytotoxin; plant metabolite
trichodermamide b trichodermamide B: from cultures of the marine-derived fungus Trichoderma virens; structure in first source	2.17	1	0
xanthohumol xanthohumol: from hop plant, Humulus lupulus. xanthohumol : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells.	2.06	1	0	aromatic ether; chalcones; polyphenol	anti-HIV-1 agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor; metabolite
ilepcimide ilepcimide: structure given in first source; RN given refers to compound with no isomeric designation	3.33	6	0	benzodioxoles
rauwolscine Rauwolscine: A stereoisomer of yohimbine.	2.07	1	0	methyl 17-hydroxy-20xi-yohimban-16-carboxylate
discodermolide [no description available]	3.25	1	0	diterpenoid
cannabidiol Cannabidiol: Compound isolated from Cannabis sativa extract.. cannabidiol : An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4.	10.17	3	1	olefinic compound; phytocannabinoid; resorcinols	antimicrobial agent; plant metabolite
gw9662 2-chloro-5-nitrobenzanilide: pretreatment of peroxisome proliferator activated receptors with GW9662 results in the irreversible loss of ligand binding	2.15	1	0	benzamides
amygdalin (R)-amygdalin : An amygdalin in which the stereocentre on the cyanohydrin function has R-configuration.	2.07	1	0	amygdalin	antineoplastic agent; apoptosis inducer; plant metabolite
hydrastine, (r-(r,s))-isomer [no description available]	2.07	1	0	isoquinolines
tiamulin tiamulin: 81723 HFU and tiamutin are for fumarate salt; prevents senescence in ascomycete; pleuromutilin derivative; RN given refers to ((3aS-(3aalpha,4beta,5alpha,6alpha,8beta,9alpha,9abeta,10S*))-isomer. tiamulin : A carbotricyclic compound that is pleuromutilin in which the hydroxyacetate group is replaced by a 2-{[2-(diethylamino)ethyl]sulfanyl}acetate group. An antibacterial drug, tiamulin is used in veterinary medicine (generally as its hydrogen fumarate salt) for the treatment of swine dysentery caused by Serpulina hyodysenteriae.	3.25	1	0	carbotricyclic compound; carboxylic ester; cyclic ketone; organic sulfide; secondary alcohol; semisynthetic derivative; tertiary amino compound; tetracyclic diterpenoid	antibacterial drug
leuprolide Leuprolide: A potent synthetic long-acting agonist of GONADOTROPIN-RELEASING HORMONE that regulates the synthesis and release of pituitary gonadotropins, LUTEINIZING HORMONE and FOLLICLE STIMULATING HORMONE.. leuprolide : An oligopeptide comprising pyroglutamyl, histidyl, tryptophyl, seryl, tyrosyl, D-leucyl, leucyl, arginyl, and N-ethylprolinamide residues joined in sequence. It is a synthetic nonapeptide analogue of gonadotropin-releasing hormone, and is used as a subcutaneous hydrogel implant (particularly as the acetate salt) for the treatment of prostate cancer and for the suppression of gonadal sex hormone production in children with central precocious puberty.	2.05	1	0	oligopeptide	anti-estrogen; antineoplastic agent; gonadotropin releasing hormone agonist
octotropine methylbromide octotropine methylbromide: minor descriptor (65-86); on line & INDEX MEDICUS search TROPANES (69-86); RN given refers to endo-isomer. anisotropine methylbromide : A quaternary ammonium salt resulting from the reaction of the amino group of anisotropine with methyl bromide.	2.05	1	0
propylthiouracil Propylthiouracil: A thiourea antithyroid agent. Propythiouracil inhibits the synthesis of thyroxine and inhibits the peripheral conversion of throxine to tri-iodothyronine. It is used in the treatment of hyperthyroidism. (From Martindale, The Extra Pharmacopeoia, 30th ed, p534). 6-propyl-2-thiouracil : A pyrimidinethione consisting of uracil in which the 2-oxo group is substituted by a thio group and the hydrogen at position 6 is substituted by a propyl group.	2.01	1	0	pyrimidinethione	antidote to paracetamol poisoning; antimetabolite; antioxidant; antithyroid drug; carcinogenic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor; hormone antagonist
ipratropium bromide anhydrous [no description available]	2.05	1	0
sesquiterpenes [no description available]	3.06	4	0
vasicine vasicine: RN given refers to (R)-isomer	2.39	2	0
sb 366791 N-(3-methoxyphenyl)-4-chlorocinnamanilide: a TRPV1 antagonist; structure in first source	2.45	2	0
3,3',4,5'-tetrahydroxystilbene 3,3',4,5'-tetrahydroxystilbene: demethyl derivative of isorhapontigenin; structure in first source; a Syk kinase inhibitor; found in heartwood of FABACEAE; inhibitor of photosynthesis in spinach chloroplasts; may be inhibitor of plant growth; RN given refers to (E)-isomer. piceatannol : A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.	2.07	1	0	catechols; polyphenol; resorcinols; stilbenol	antineoplastic agent; apoptosis inducer; geroprotector; hypoglycemic agent; plant metabolite; protein kinase inhibitor; tyrosine kinase inhibitor
thioinosine Thioinosine: Sulfhydryl analog of INOSINE that inhibits nucleoside transport across erythrocyte plasma membranes, and has immunosuppressive properties. It has been used similarly to MERCAPTOPURINE in the treatment of leukemia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p503)	1.98	1	0
(e)-3-(4-t-butylphenyl)-n-(2,3-dihydrobenzo(b)(1,4)dioxin-6-yl)acrylamide 3-(4-t-butylphenyl)-N-(2,3-dihydrobenzo(b)(1,4)dioxin-6-yl)acrylamide: a vanilloid receptor 1 antagonist and antihyperalgesic agent; structure in first source	2.05	1	0
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.07	1	0	caffeic acid	geroprotector; mouse metabolite
pongamol pongamol: from Pongamia pinnata fruits; structure in first source	2.17	1	0
methyl caffeate methyl caffeate: from plant Gaillardia pulchella. methyl caffeate : An alkyl caffeate ester formed by the formal condensation of caffeic acid with methyl alcohol.	2.02	1	0	alkyl caffeate ester; methyl ester
phenylalanine methyl ester phenylalanine methyl ester: RN given refers to (L)-isomer. methyl L-phenylalaninate : An alpha-amino acid ester that is the methyl ester of L-phenylalanine.	2.05	1	0	alpha-amino acid ester; L-phenylalanine derivative
cotinine Cotinine: The N-glucuronide conjugate of cotinine is a major urinary metabolite of NICOTINE. It thus serves as a biomarker of exposure to tobacco SMOKING. It has CNS stimulating properties.. (-)-cotinine : An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum.	2.07	1	0	N-alkylpyrrolidine; pyridines; pyrrolidin-2-ones; pyrrolidine alkaloid	antidepressant; biomarker; human xenobiotic metabolite; plant metabolite
heliotrine [no description available]	2.07	1	0	pyrrolizines
sclareolide [no description available]	2.07	1	0	naphthofuran
flunarizine Flunarizine: Flunarizine is a selective calcium entry blocker with calmodulin binding properties and histamine H1 blocking activity. It is effective in the prophylaxis of migraine, occlusive peripheral vascular disease, vertigo of central and peripheral origin, and as an adjuvant in the therapy of epilepsy.	2.05	1	0	diarylmethane
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	16.1	126	21	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
hypocrellin b hypocrellin B: photosensitive pigments isolated from Hypocrella bambusae Sacc; structure given in first source	2.07	1	0
hc 030031 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)-N-(4-isopropylphenyl)acetamide: a TRPA1 channel blocker	2.11	1	0
snap 37889 [no description available]	2.05	1	0
sulindac Sulindac: A sulfinylindene derivative prodrug whose sulfinyl moiety is converted in vivo to an active NSAID analgesic. Specifically, the prodrug is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This helps to maintain constant blood levels with reduced gastrointestinal side effects.. sulindac : A monocarboxylic acid that is 1-benzylidene-1H-indene which is substituted at positions 2, 3, and 5 by methyl, carboxymethyl, and fluorine respectively, and in which the phenyl group of the benzylidene moiety is substituted at the para position by a methylsulfinyl group. It is a prodrug for the corresponding sulfide, a non-steroidal anti-inflammatory drug, used particularly in the treatment of acute and chronic inflammatory conditions.	2.05	1	0	monocarboxylic acid; organofluorine compound; sulfoxide	analgesic; antineoplastic agent; antipyretic; apoptosis inducer; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug; tocolytic agent
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	11.92	68	4	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
aurapten aurapten: RN refers to (E)-isomer; structure given in first source. auraptene : A member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group. Ii is isolated from several edible fruits and vegetables and exhibits a variety of therapeutic properties.	2.07	1	0	coumarins; monoterpenoid	antihypertensive agent; antineoplastic agent; antioxidant; apoptosis inducer; dopaminergic agent; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; gamma-secretase modulator; gastrointestinal drug; hepatoprotective agent; matrix metalloproteinase inhibitor; neuroprotective agent; plant metabolite; PPARalpha agonist; vulnerary
caryophyllene oxide caryophyllene oxide: has butyrylcholinesterase inhibitory activity; structure in first source. epoxide : Any cyclic ether in which the oxygen atom forms part of a 3-membered ring.	2.11	1	0	epoxide	metabolite
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	2.55	2	0	cinnamate ester; tannin	food component; plant metabolite
tempo TEMPO: structure. TEMPO : A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.	2.31	1	0	aminoxyls; piperidines	catalyst; ferroptosis inhibitor; radical scavenger
digoxin Digoxin: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666). digoxin : A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.	2.72	3	0	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
capsazepine capsazepine: modified capsaicin molecule; a capsaicin receptor antagonist. capsazepine : A benzazepine that is 2,3,4,5-tetrahydro-1H-2-benzazepine which is substituted by hydroxy groups at positions 7 and 8 and on the nitrogen atom by a 2-(p-chlorophenyl)ethylaminothiocarbonyl group. A synthetic analogue of capsaicin, it was the first reported capsaicin receptor antagonist.	8.53	8	0	benzazepine; catechols; monochlorobenzenes; thioureas	capsaicin receptor antagonist
fumonisin b2 fumonisin B2: produced by Fusarium moniliforme MRC 826; structure given in first source; has cancer-promoting ability. fumonisin B2 : A fumonisin that is (2S,3S,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,14,15-triol in which the hydroxy groups at positions 14 and 15 have each been esterified by condensation with the 1-carboxy group of 3-carboxyglutaric acid (giving a 3-carboxyglutarate ester group with R configuration in each case).	2.07	1	0	diester; diol; fumonisin; primary amino compound	Aspergillus metabolite; carcinogenic agent
tamoxifen [no description available]	7.82	3	0	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
nadp [no description available]	7.13	1	0
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.31	1	0
ethionamide Ethionamide: A second-line antitubercular agent that inhibits mycolic acid synthesis.. ethionamide : A thiocarboxamide that is pyridine-4-carbothioamide substituted by an ethyl group at position 2. A prodrug that undergoes metabolic activation by conversion to the corresponding S-oxide.	2.05	1	0	pyridines; thiocarboxamide	antilipemic drug; antitubercular agent; fatty acid synthesis inhibitor; leprostatic drug; prodrug
artemotil artemotil: structure given in first source; RN given refers to cpd without isomeric designation	2.05	1	0	artemisinin derivative
lincomycin Lincomycin: An antibiotic produced by Streptomyces lincolnensis var. lincolnensis. It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.. lincomycin : A carbohydrate-containing antibiotic produced by the actinomyces Streptomyces lincolnensis.	2.07	1	0	carbohydrate-containing antibiotic; L-proline derivative; monocarboxylic acid amide; pyrrolidinecarboxamide; S-glycosyl compound	antimicrobial agent; bacterial metabolite
valinomycin Valinomycin: A cyclododecadepsipeptide ionophore antibiotic produced by Streptomyces fulvissimus and related to the enniatins. It is composed of 3 moles each of L-valine, D-alpha-hydroxyisovaleric acid, D-valine, and L-lactic acid linked alternately to form a 36-membered ring. (From Merck Index, 11th ed) Valinomycin is a potassium selective ionophore and is commonly used as a tool in biochemical studies.. valinomycin : A twelve-membered cyclodepsipeptide composed of three repeating D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl units joined in sequence. An antibiotic found in several Streptomyces strains.	2.07	1	0	cyclodepsipeptide; macrocycle	antimicrobial agent; antiviral agent; bacterial metabolite; potassium ionophore
helvolic acid helvolic acid: structure. helvolic acid : A steroid C-21 acid having a 29-nordammarane skeleton substituted with an acetoxy group at C-16 and oxo groups at C-3 and -7, with double bonds at C-1, -17(20) and -24.	2.17	1	0	3-oxo-Delta(1) steroid; acetate ester; monocarboxylic acid; steroid acid	antibacterial agent; fungal metabolite; mycotoxin
gestodene Gestodene: synthetic steroid with progestational activity; RN given refers to (17alpha)-isomer	2.05	1	0	steroid	estrogen
glucametacin glucametacin: indomethacin analog; structure	2.05	1	0
orlistat Orlistat: A lactone derivative of LEUCINE that acts as a pancreatic lipase inhibitor to limit the absorption of dietary fat; it is used in the management of obesity.. orlistat : A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.	2.07	1	0	beta-lactone; carboxylic ester; formamides; L-leucine derivative	anti-obesity agent; bacterial metabolite; EC 2.3.1.85 (fatty acid synthase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor
quinine [no description available]	2.68	3	0	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
mitragynine [no description available]	2.17	1	0	monoterpenoid indole alkaloid
12-deoxyphorbolphenylacetate-20-acetate [no description available]	2.07	1	0
brassinin [no description available]	2.07	1	0	dithiocarbamic ester; indole phytoalexin
chaetomellic acid a chaetomellic acid A: structure given in first source; an inhibitor of farnesyl-protein transferase	2.07	1	0
paynantheine paynantheine: structure in first source	2.17	1	0
hirsutine [no description available]	2.07	1	0
3-deoxyvasicine, hydrochloride [no description available]	2.07	1	0
rasagiline [no description available]	2.25	1	0	indanes; secondary amine; terminal acetylenic compound	EC 1.4.3.4 (monoamine oxidase) inhibitor; neuroprotective agent
emetine dihydrochloride emetine dihydrochloride : The dihydrochloride salt of emetine.. emetine dihydrochloride hydrate : A hydrate that is the monohydrate of the dihydrochloride salt of emetine.	2.07	1	0	hydrochloride	anticoronaviral agent; antimalarial; antineoplastic agent; antiprotozoal drug; antiviral agent; autophagy inhibitor; emetic; protein synthesis inhibitor
2,3,4-tri-o-acetylarabinopyranosyl isothiocyanate 2,3,4-tri-O-acetylarabinopyranosyl isothiocyanate: RN given refers to (alpha-D)-isomer	2.41	1	0
chimonanthine chimonanthine: structure in first source. chimonanthine : A ring assembly that is 2,2',3,3',8,8',8a,8a'-octahydro-1H,1'H-3a,3a'-bipyrrolo[2,3-b]indole substituted by methyl groups at positions 1 and 1'.	2.17	1	0	chimonanthine
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.8	3	0
salinomycin salinomycin: from Streptomyces albus; RN given refers to parent cpd; structure	2.07	1	0	polyketide; spiroketal	animal growth promotant; potassium ionophore
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	2.17	1	0
silybin [no description available]	2.75	3	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	3.17	5	0
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.77	3	0
rhodamine 123 Rhodamine 123: A fluorescent probe with low toxicity which is a potent substrate for ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 and the bacterial multidrug efflux transporter. It is used to assess mitochondrial bioenergetics in living cells and to measure the efflux activity of ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 in both normal and malignant cells. (Leukemia 1997;11(7):1124-30). rhodamine 123(1+) : A cationic fluorescent dye derived from 9-phenylxanthene.	2.17	1	0	organic cation; xanthene dye	fluorochrome
3-deoxyisoochracinic acid 3-deoxyisoochracinic acid: structure in first source	2.17	1	0
alsterpaullone alsterpaullone: structure in first source. alsterpaullone : An organic heterotetracyclic compound that is 1,3-dihydro-2H-1-benzazepin-2-one which shares its 4-5 bond with the 3-2 bond of 5-nitro-1H-indole.	2.05	1	0	C-nitro compound; caprolactams; organic heterotetracyclic compound	anti-HIV-1 agent; antineoplastic agent; apoptosis inducer; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor; EC 2.7.11.26 (tau-protein kinase) inhibitor
diclofenac sodium Diclofenac Sodium: The sodium form of DICLOFENAC. It is used for its analgesic and anti-inflammatory properties.. diclofenac sodium : The sodium salt of diclofenac.	2.11	1	0	organic sodium salt
5,6-dehydrokawain 5,6-dehydrokawain: from Alpinia speciosa rhizoma; RN given for cpd without isomeric designation; structure given in first source	2.07	1	0	2-pyranones; aromatic ether
9,10-dihydrolysergol 9,10-dihydrolysergol: RN given refers to cpd without isomeric designation	2.07	1	0
geranylgeranic acid geranylgeranic acid: RN given refers to cpd without isomeric designation. (2E,6E,10E)-geranylgeranic acid : A diterpenoid obtained by formal oxidation of the CH2OH group of (E,E,E)-geranylgeraniol to the corresponding carboxylic acid.	2.07	1	0	alpha,beta-unsaturated monocarboxylic acid; diterpenoid; methyl-branched fatty acid; trienoic fatty acid
quercetin [no description available]	6.68	20	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
bilirubin [no description available]	2.41	1	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	3.18	5	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	2.07	1	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
biochanin a [no description available]	2.07	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	antineoplastic agent; EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
formononetin [no description available]	2.07	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	phytoestrogen; plant metabolite
prostaglandin b1 prostaglandin Bx: phospholipase A2 inhibitor; polymeric derivative of diketo-PGB1; mean MW 2,200. prostaglandin B1 : A member of the class of prostaglandins B that is prosta-8(12),13-dien-1-oic acid carrying oxo and hydroxy substituents at positions 9 and 15 respectively (the 13E,15S-stereoisomer).	2.07	1	0	prostaglandins B	human metabolite
sterigmatocystin [no description available]	2.07	1	0	sterigmatocystins	metabolite
vitexin [no description available]	2.52	2	0	C-glycosyl compound; trihydroxyflavone	antineoplastic agent; EC 3.2.1.20 (alpha-glucosidase) inhibitor; plant metabolite; platelet aggregation inhibitor
acacetin 5,7-dihydroxy-4'-methoxyflavone : A monomethoxyflavone that is the 4'-methyl ether derivative of apigenin.	2.07	1	0	dihydroxyflavone; monomethoxyflavone	anticonvulsant; plant metabolite
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	8.02	4	0	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	2.07	1	0	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist
quercitrin [no description available]	2.07	1	0	alpha-L-rhamnoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	antileishmanial agent; antioxidant; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; plant metabolite
scopoletin [no description available]	2.52	2	0	hydroxycoumarin	plant growth regulator; plant metabolite
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	3.21	1	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
hymecromone Hymecromone: A coumarin derivative possessing properties as a spasmolytic, choleretic and light-protective agent. It is also used in ANALYTICAL CHEMISTRY TECHNIQUES for the determination of NITRIC ACID.	2.07	1	0	hydroxycoumarin	antineoplastic agent; hyaluronic acid synthesis inhibitor
luteolin-7-glucoside luteolin-7-glucoside: has both antiasthmatic and antineoplastic activities; has 3C protease inhibitory activity; isolated from Ligustrum lucidum. luteolin 7-O-beta-D-glucoside : A glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.17	1	0	beta-D-glucoside; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antioxidant; plant metabolite
alprostadil [no description available]	2.47	2	0	prostaglandins E	anticoagulant; human metabolite; platelet aggregation inhibitor; vasodilator agent
stigmasterol stigmasta-5,22-dien-3-ol: isolated from freeze-dried powder of Blackberries (Rubus ursinus L.) which showed an activity on inhibition of chemocarcinogen. stigmasterol : A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions.	2.15	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols; stigmastane sterol	plant metabolite
cholecalciferol Cholecalciferol: Derivative of 7-dehydroxycholesterol formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. It differs from ERGOCALCIFEROL in having a single bond between C22 and C23 and lacking a methyl group at C24.. calciol : A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone.	4.52	2	0	D3 vitamins; hydroxy seco-steroid; seco-cholestane; secondary alcohol; steroid hormone	geroprotector; human metabolite
quercetin 3-o-glucopyranoside quercetin 3-O-glucopyranoside: structure in first source. quercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells	2.07	1	0	beta-D-glucoside; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; antipruritic drug; bone density conservation agent; geroprotector; histamine antagonist; osteogenesis regulator; plant metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	7.84	3	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	2.52	2	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
senecionine senecionine: RN given refers to parent cpd; structure. senecionine : A pyrrolizidine alkaloid isolated from the plant species of the genus Senecio.	2.07	1	0	lactone; pyrrolizidine alkaloid; tertiary alcohol	plant metabolite
harmine Harmine: Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920's.. harmine : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7.	2.77	3	0	harmala alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; metabolite
genistein [no description available]	4.38	3	0	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	8.2	5	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
pulmicort Budesonide: A glucocorticoid used in the management of ASTHMA, the treatment of various skin disorders, and allergic RHINITIS.. budesonide : A glucocorticoid steroid having a highly oxygenated pregna-1,4-diene structure. It is used mainly in the treatment of asthma and non-infectious rhinitis and for treatment and prevention of nasal polyposis.	2.11	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; cyclic acetal; glucocorticoid; primary alpha-hydroxy ketone	anti-inflammatory drug; bronchodilator agent; drug allergen
montelukast montelukast: a leukotriene D4 receptor antagonist	2.11	1	0	aliphatic sulfide; monocarboxylic acid; quinolines	anti-arrhythmia drug; anti-asthmatic drug; leukotriene antagonist
butein [no description available]	2.07	1	0	chalcones; polyphenol	antineoplastic agent; antioxidant; EC 1.1.1.21 (aldehyde reductase) inhibitor; geroprotector; hypoglycemic agent; plant metabolite; radiosensitizing agent; tyrosine kinase inhibitor
gardenia yellow gardenia yellow: extract of gardenia fruit; RN given refers to cpd with unknown MF. crocin-1 : A diester that is crocetin in which both of the carboxy groups have been converted to their gentiobiosyl esters. It is one of the water-soluble yellow-red pigments of saffron and is used as a spice for flavouring and colouring food. Note that in India, the term 'Crocin' is also used by GlaxoSmithKline as a brand-name for paracetamol.	2.11	1	0	diester; disaccharide derivative; diterpenoid	antioxidant; food colouring; histological dye; plant metabolite
fucoxanthin fucoxanthin: RN given refers to (3S,3'S,5R,5'R,6S,6'R)-isomer. fucoxanthin : An epoxycarotenol that is found in brown seaweed and which exhibits anti-cancer, anti-diabetic, anti-oxidative and neuroprotective properties.	3.21	1	0
isobavachalcone isobavachalcone: RN given for (E)-isomer; structure in first source. isobavachalcone : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4' and a prenyl group at position 3'.	3.51	1	0	chalcones; polyphenol	antibacterial agent; metabolite; platelet aggregation inhibitor
sulfuretin sulfuretin: the chalcone C ring closes into a 5 instead of the more typical 6 membered ring leaving a phenyl methane at the 2 position instead of the typical phenyl	2.07	1	0	1-benzofurans
genistin genistin: glycoside of soy bean isoflavone, gentistein	2.07	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside
chartreusin chartreusin: structure	2.07	1	0	benzochromenone; glycoside
harman harman: a beta-carboline; RN given refers to parent cpd; structure. harman : An indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A.	2.04	1	0	harmala alkaloid; indole alkaloid fundamental parent; indole alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
usambarensine usambarensine: structure given in first source	2.05	1	0	harmala alkaloid
methysticin [no description available]	2.07	1	0	2-pyranones; aromatic ether
yangonin yangonin: structure in first source	2.07	1	0	2-pyranones; aromatic ether
zearalenone Zearalenone: (S-(E))-3,4,5,6,8,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione. One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.. zearalenone : A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.	2.07	1	0	macrolide; resorcinols	fungal metabolite; mycoestrogen
apigenin dimethylether apigenin dimethylether: a dimethoxy analog of apigenin from roots of Rhus undulata and possibly other plants. apigenin 7,4'-dimethyl ether : A dimethoxyflavone that is the 7,4'-dimethyl ether derivative of apigenin.	2.04	1	0	dimethoxyflavone; monohydroxyflavone	plant metabolite
baicalein [no description available]	2.79	3	0	trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 4.1.1.17 (ornithine decarboxylase) inhibitor; ferroptosis inhibitor; geroprotector; hormone antagonist; plant metabolite; prostaglandin antagonist; radical scavenger
chrysin chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.	2.52	2	0	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
datiscetin datiscetin : A tetrahydroxyflavone that is 7-hydroxyflavonol bearing two additional hydroxy substituents at positions 2' and 5.	2.07	1	0	7-hydroxyflavonol; tetrahydroxyflavone
diosmetin [no description available]	2.07	1	0	3'-hydroxyflavonoid; monomethoxyflavone; trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; bone density conservation agent; cardioprotective agent; plant metabolite; tropomyosin-related kinase B receptor agonist; vasodilator agent
diosmin [no description available]	2.07	1	0	dihydroxyflavanone; disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; rutinoside	anti-inflammatory agent; antioxidant
fisetin [no description available]	2.52	2	0	3'-hydroxyflavonoid; 7-hydroxyflavonol; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; metabolite; plant metabolite
galangin 5,7-dihydroxyflavonol: antimicrobial from the twigs of Populus nigra x Populus deltoides; structure in first source. galangin : A 7-hydroxyflavonol with additional hydroxy groups at positions 3 and 5 respectively; a growth inhibitor of breast tumor cells.	2.07	1	0	7-hydroxyflavonol; trihydroxyflavone	antimicrobial agent; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; plant metabolite
hispidulin hispidulin : A monomethoxyflavone that is scutellarein methylated at position 6.	2.17	1	0	monomethoxyflavone; trihydroxyflavone	anti-inflammatory agent; anticonvulsant; antineoplastic agent; antioxidant; apoptosis inducer; plant metabolite
mangiferin shamimin: isolated from the leaves of Bombax ceiba; structure in first source	2.11	1	0	C-glycosyl compound; xanthones	anti-inflammatory agent; antioxidant; hypoglycemic agent; plant metabolite
3-methylquercetin isorhamnetin : A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.	2.07	1	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	anticoagulant; EC 1.14.18.1 (tyrosinase) inhibitor; metabolite
morin morin: a light yellowish pigment found in the wood of old fustic (Chlorophora tinctoria). morin : A pentahydroxyflavone that is 7-hydroxyflavonol bearing three additional hydroxy substituents at positions 2' 4' and 5.	2.07	1	0	7-hydroxyflavonol; pentahydroxyflavone	angiogenesis modulating agent; anti-inflammatory agent; antibacterial agent; antihypertensive agent; antineoplastic agent; antioxidant; EC 5.99.1.2 (DNA topoisomerase) inhibitor; hepatoprotective agent; metabolite; neuroprotective agent
myricetin [no description available]	2.07	1	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
rhamnetin rhamnetin: aglycone of xanthorhamnin; from Rhamnus. rhamnetin : A monomethoxyflavone that is quercetin methylated at position 7.	2.07	1	0	monomethoxyflavone; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; metabolite
robinetin robinetin: structure given in first source. robinetin : A pentahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 7, 3, 4' and 5'.	2.07	1	0	7-hydroxyflavonol; pentahydroxyflavone	plant metabolite
tamarixetin tamarixetin: isolated from Costsus spicatus. tamarixetin : A monomethoxyflavone that is quercetin methylated at position O-4'. Isolated from Cyperus teneriffae.	2.07	1	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	antioxidant; metabolite
wogonin wogonin: structure in first source. wogonin : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-8.	2.52	2	0	dihydroxyflavone; monomethoxyflavone	angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite
coumestrol Coumestrol: A daidzein derivative occurring naturally in forage crops which has some estrogenic activity.. coumestrol : A member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9.	2.07	1	0	coumestans; delta-lactone; polyphenol	anti-inflammatory agent; antioxidant; plant metabolite
daidzein [no description available]	2.07	1	0	7-hydroxyisoflavones	antineoplastic agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; phytoestrogen; plant metabolite
trans-2,3',4,5'-tetrahydroxystilbene trans-2,3',4,5'-tetrahydroxystilbene: hydroxystilbene oxyresveratrol	2.61	2	0	stilbenoid
pterostilbene [no description available]	2.21	1	0	diether; methoxybenzenes; stilbenol	anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; hypoglycemic agent; neuroprotective agent; neurotransmitter; plant metabolite; radical scavenger
cynarine cynarine: active principle of the artichoke; functions primarily as a cholagogue and choleretic and also as antilipemic agent	2.05	1	0	alkyl caffeate ester; quinic acid	plant metabolite
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	2.46	2	0	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
rosmarinic acid rosmarinic acid: RN given refers to parent cpd; promote OT project. (R)-rosmarinic acid : A stereoisomer of rosmarinic acid having (R)-configuration.. rosmarinic acid : The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.	2.07	1	0	rosmarinic acid	geroprotector; plant metabolite
shogaol shogaol: from ginger, ZINGIBER OFFICINALE; less mutagenic than GINGEROL; structure given in first source	2.1	1	0	enone; monomethoxybenzene; phenols
acteoside acteoside: a protein kinase C inhibitor with hepatoprotective, anti-asthmatic, and analgesic activities; a phenylethanoid glycoside related to isoacteoside; from leaves of Lippia multiflora (Verbenaceae). acteoside : A glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid.	2.05	1	0	catechols; cinnamate ester; disaccharide derivative; glycoside; polyphenol	anti-inflammatory agent; antibacterial agent; antileishmanial agent; neuroprotective agent; plant metabolite
wedelolactone wedelolactone: antihepatotoxic coumestan from Eclipta prostrata and Wedelia calendulacea (both Asteraceae); structure given in first source. wedelolactone : A member of the class of coumestans that is coumestan with hydroxy substituents as positions 1, 8 and 9 and a methoxy substituent at position 3.	2.07	1	0	aromatic ether; coumestans; delta-lactone; polyphenol	antineoplastic agent; apoptosis inducer; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; hepatoprotective agent; metabolite
rottlerin rottlerin: an angiogenesis inhibitor; an inhibitor of protein kinase Cdelta (PKCdelta) and calmodulin kinase III; RN refers to (E)-isomer; do not confuse this chalcone with an anthraquinone that is also called rottlerin (RN 481-72-1);. rottlerin : A chromenol that is 2,2-dimethyl-2H-chromene substituted by hydroxy groups at positions 5 and 7, a 3-acetyl-2,4,6-trihydroxy-5-methylbenzyl group at position 6 and a (1E)-3-oxo-1-phenylprop-1-en-3-yl group at position 8. A potassium channel opener, it is isolated from Mallotus philippensis.	2.07	1	0	aromatic ketone; benzenetriol; chromenol; enone; methyl ketone	anti-allergic agent; antihypertensive agent; antineoplastic agent; apoptosis inducer; K-ATP channel agonist; metabolite
ellagic acid [no description available]	2.07	1	0	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
7-hydroxyflavone 7-hydroxyflavone : A hydroxyflavonoid in which the flavone nucleus is substituted at position 7 by a hydroxy group.	2.07	1	0	hydroxyflavonoid
prostaglandin a1 [no description available]	2.07	1	0	prostaglandins A
anandamide anandamide : An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.	3.52	2	0	endocannabinoid; N-acylethanolamine 20:4	human blood serum metabolite; neurotransmitter; vasodilator agent
cerulenin Cerulenin: An epoxydodecadienamide isolated from several species, including ACREMONIUM, Acrocylindrum, and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.. cerulenin : An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.	2.07	1	0	epoxide; monocarboxylic acid amide	antifungal agent; antiinfective agent; antilipemic drug; antimetabolite; antimicrobial agent; fatty acid synthesis inhibitor
rhoifolin rhoifolin: from many plants. apigenin 7-O-neohesperidoside : An apigenin derivative having an alpha-(1->2)-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety attached to the 7-hydroxy group.	2.07	1	0	dihydroxyflavone; glycosyloxyflavone; neohesperidoside	metabolite
vitexin rhamnoside 2''-O-rhamnopyranosylvitexin: has both analgesic and anti-inflammatory activities; isolated from Alternanthera maritima; structure in first source. vitexin 2''-O-alpha-L-rhamnoside : A derivative of vitexin having an alpha-L-rhamnosyl residue attached at the 2''-position of the glucitol moiety.	2.07	1	0	C-glycosyl compound; disaccharide derivative; trihydroxyflavone	plant metabolite
domoic acid domoic acid: kainic acid analog, heterocyclic amino acid from seaweed; RN given refers to parent cpd; structure. domoic acid : An L-proline derivative that is L-proline substituted by a carboxymethyl group at position 3 and a 6-carboxyhepta-2,4-dien-2-yl group at position 4. It is produced by the diatomic algal Pseudo-nitzschia. It is an analogue of kainic acid and a neurotoxin which causes amnesic shellfish poisoning (ASP).	2.07	1	0	L-proline derivative; non-proteinogenic L-alpha-amino acid; pyrrolidinecarboxylic acid; tricarboxylic acid	algal metabolite; hapten; marine metabolite; neuromuscular agent; neurotoxin
isotretinoin Isotretinoin: A topical dermatologic agent that is used in the treatment of ACNE VULGARIS and several other skin diseases. The drug has teratogenic and other adverse effects.. isotretinoin : A retinoic acid that is all-trans-retinoic acid in which the double bond which is alpha,beta- to the carboxy group is isomerised to Z configuration. A synthetic retinoid, it is used for the treatment of severe cases of acne and other skin diseases.	2.07	1	0	retinoic acid	antineoplastic agent; keratolytic drug; teratogenic agent
triprolidine Triprolidine: Histamine H1 antagonist used in allergic rhinitis; ASTHMA; and URTICARIA. It is a component of COUGH and COLD medicines. It may cause drowsiness.. triprolidine : An N-alkylpyrrolidine that is acrivastine in which the pyridine ring is lacking the propenoic acid substituent. It is a sedating antihistamine that is used (generally as the monohydrochloride monohydrate) for the relief of the symptoms of uticaria, rhinitis, and various pruritic skin disorders.	2.05	1	0	N-alkylpyrrolidine; olefinic compound; pyridines	H1-receptor antagonist
terbinafine hydrochloride terbinafine hydrochloride : A hydrochloride obtained by reaction of terbinafine with one molar equivalent of hydrogen chloride.	2.11	1	0	allylamine antifungal drug; hydrochloride	EC 1.14.13.132 (squalene monooxygenase) inhibitor; P450 inhibitor
1-monooleoyl-rac-glycerol Peceol: lipid excipient containing readily dispersible mixture of mono- & diglycerides of oleic acid. 1-oleoylglycerol : A 1-monoglyceride where the acyl group is oleoyl.. monooleoylglycerol : A monoglyceride in which the acyl group is oleoyl with the position of acylation unspecified.	2.11	1	0	1-acylglycerol 18:1; monooleoylglycerol	plant metabolite
codeine [no description available]	2.05	1	0	morphinane alkaloid; organic heteropentacyclic compound	antitussive; drug allergen; environmental contaminant; opioid analgesic; opioid receptor agonist; prodrug; xenobiotic
cyclosporine ramihyphin A: one of the metabolites produced by Fusarium sp. S-435; RN given refers to cpd with unknown MF	2.07	1	0	homodetic cyclic peptide	anti-asthmatic drug; anticoronaviral agent; antifungal agent; antirheumatic drug; carcinogenic agent; dermatologic drug; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; geroprotector; immunosuppressive agent; metabolite
natamycin [no description available]	2.07	1	0	antibiotic antifungal drug; dicarboxylic acid monoester; epoxide; macrolide antibiotic; monosaccharide derivative; polyene antibiotic	antifungal agrochemical; antimicrobial food preservative; apoptosis inducer; bacterial metabolite; ophthalmology drug
dihydrocodeine dihydrocodeine: RN refers to parent cpd(5alpha,6alpha)-isomer	2.05	1	0	morphinane alkaloid
ly 163892 loracarbef: 1-carbacephem antibiotic; has a broad spectrum of antimicrobial activity; structure given in first source; carbacephems differ from cephalosporins in the substitution of a sulfur atom in the dihydrothiazine ring with a methylene group to form a tetrahydropyridine ring. loracarbef : A synthetic "carba" analogue of cefaclor, with carbon replacing sulfur at position 1. Used to treat a wide range of infections caused by both gram-positive and gram-negative bacteria.	2.05	1	0	carbacephem; zwitterion	antibacterial drug; antimicrobial agent
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	2.96	4	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
sirolimus Sirolimus: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.. sirolimus : A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.	2.5	2	0	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
brefeldin a [no description available]	2.07	1	0	macrolide antibiotic	Penicillium metabolite
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	2.05	1	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
olvanil [no description available]	8.84	3	0	methoxybenzenes; phenols
lacidipine [no description available]	2.05	1	0	cinnamate ester; tert-butyl ester
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	2.25	1	0	1-O-acyl-sn-glycero-3-phosphocholine
cytochalasin b Cytochalasin B: A cytotoxic member of the CYTOCHALASINS.. cytochalasin B : An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.	2.52	2	0	cytochalasin; lactam; lactone; organic heterotricyclic compound	actin polymerisation inhibitor; metabolite; mycotoxin; platelet aggregation inhibitor
nateglinide Nateglinide: A phenylalanine and cyclohexane derivative that acts as a hypoglycemic agent by stimulating the release of insulin from the pancreas. It is used in the treatment of TYPE 2 DIABETES.. nateglinide : An N-acyl-D-phenylalanine resulting from the formal condensation of the amino group of D-phenylalanine with the carboxy group of trans-4-isopropylcyclohexanecarboxylic acid. An orally-administered, rapidly-absorbed, short-acting insulinotropic agent, it is used for the treatment of type 2 diabetes mellitus.	7.07	1	0	phenylalanine derivative
sq 29548 SQ 29548: SQ-26538 is the ((1S-1alpha,2beta(5Z),3beta(1E,3R*),4alpha))-isomer; thromboxane A2 antagonist; thromboxane receptor antagonist	2.03	1	0
vinorelbine [no description available]	2.47	2	0	acetate ester; methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; ring assembly; vinca alkaloid	antineoplastic agent; photosensitizing agent
bisdemethoxycurcumin curcumin III: structure in first source. bisdemethoxycurcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups.	2.49	2	0	beta-diketone; diarylheptanoid; enone; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; metabolite
kaempferol 3-o-rhamnoside kaempferol 3-O-rhamnoside: from apple (Malus domestica) leaves; structure in first source. afzelin : A glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage.	2.17	1	0	glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	anti-inflammatory agent; antibacterial agent; plant metabolite
linarin linarin: flavone glycoside isolated from leaves of Linaria japonica MIQ	7.1	1	0
pellitorine pellitorine: consists of piper sylvaticum Roxb.; structure	9.67	8	0	fatty amide	metabolite
andrographolide [no description available]	7.57	2	0	carbobicyclic compound; gamma-lactone; labdane diterpenoid; primary alcohol; secondary alcohol	anti-HIV agent; anti-inflammatory drug; antineoplastic agent; metabolite
isorhamnetin 3-o-glucoside isorhamnetin 3-O-glucoside: from the flowers of Persea gratissima; structure in first source. isorhamnetin 3-O-beta-D-glucopyranoside : A glycosyloxyflavone that is isorhamnetin substituted at position 3 by a beta-D-glucosyl residue.	2.07	1	0	beta-D-glucoside; glycosyloxyflavone; monomethoxyflavone; monosaccharide derivative; trihydroxyflavone	metabolite
kukoamine a kukoamine A: inhibits Crithidia fasciculata trypanothione reductase; structure given in first source	2.04	1	0	amine
licochalcone a licochalcone A: has both anti-inflammatory and antineoplastic activities; structure given in first source; isolated from root of Glycyrrhiza inflata; RN given refers to (E)-isomer	2.05	1	0	chalcones
5,7-dihydroxy-6-methoxy-2-phenylchromen-4-one 5,7-dihydroxy-6-methoxy-2-phenylchromen-4-one: isolated from the Chinese herb Scutellariae radix. oroxylin A : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-6.	2.17	1	0	dihydroxyflavone; monomethoxyflavone	antineoplastic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor
Piperanine [no description available]	3.14	5	0	benzodioxoles
piperlonguminine piperlonguminine: from Piper longum; structure in first source	3.55	8	0	benzodioxoles
caryophyllene caryophyllene: RN given refers to cpd without isomeric designation; structure given in first source	2.11	1	0
fosbretabulin [no description available]	2.15	1	0	stilbenoid
stilbamidine stilbamidine: RN given refers to parent cpd	2.05	1	0
6,7-dihydroxyflavone 6,7-dihydroxyflavone: intensifies effect of antibiotics on Staphylococcus aureus; structure in first source	2.07	1	0
15-hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic acid 15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic Acid: A stable prostaglandin endoperoxide analog which serves as a thromboxane mimetic. Its actions include mimicking the hydro-osmotic effect of VASOPRESSIN and activation of TYPE C PHOSPHOLIPASES. (From J Pharmacol Exp Ther 1983;224(1): 108-117; Biochem J 1984;222(1):103-110)	2.03	1	0
flavokawain a flavokawain A: from kava extract, induces apoptosis in bladder cancer cells; structure in first source	2.07	1	0	chalcones
flavokawain b flavokawain B: from Piper methysticum Forst (Kava Kava) roots; structure in first source. flavokawain B : A member of the class of chalcones that consists of trans-chalcone substituted by hydroxy group at positions 2' and methoxy groups at positions 4' and 6'. Isolated from Piper methysticum and Piper rusbyi, it exhibits antileishmanial, anti-inflammatory and antineoplastic activities.	2.07	1	0	chalcones; dimethoxybenzene; phenols	anti-inflammatory agent; antileishmanial agent; antineoplastic agent; apoptosis inducer; metabolite
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	7.41	1	0	boron group element atom; elemental aluminium; metal atom
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	7.25	1	0	metalloid atom; pnictogen	micronutrient
lisinopril Lisinopril: One of the ANGIOTENSIN-CONVERTING ENZYME INHIBITORS (ACE inhibitors), orally active, that has been used in the treatment of hypertension and congestive heart failure.	2.41	1	0	dipeptide	EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
glyceryl behenate 1-behenoylglycerol : A fatty acid ester resulting from the formal condensation of the hydroxy group at position-1 of glycerol with the carboxy group of docosanoic acid.	2.31	1	0	1-monoglyceride; fatty acid ester	antineoplastic agent; plant metabolite
kavain [no description available]	2.07	1	0	racemate	glycine receptor antagonist
piperic acid piperinic acid: from Piper longum; structure in first source. (E,E)-piperic acid : A monocarboxylic acid that is (E)-penta-2,4-dienoic acid substituted by a 1,3-benzodioxol-5-yl group at position 5. It has been isolated from black pepper (Piper nigrum).	3.79	10	0	alpha,beta-unsaturated monocarboxylic acid; benzodioxoles	plant metabolite
Pipercide [no description available]	2.73	3	0	benzodioxoles
abscisic acid, (+,-)-isomer 2-cis-abscisic acid : A member of the class of abscisic acids in which the double bond betweeen positions 2 and 3 has cis- (natural) geometry.	2.07	1	0	abscisic acids	abscisic acid receptor agonist
veratrine Veratrine: A voltage-gated sodium channel activator.	2.07	1	0	alkaloid
radicinin radicinin: mold metabolite from plant pathogen Stemphylium radicinum; RN given refers to (2S-(2alpha,3beta,7E))-isomer; structure	2.17	1	0	aromatic ketone
vinblastine sulfate [no description available]	2.07	1	0
calycanthine calycanthine: the principal alkaloid of the plant family Calycanthaceae; RN given refers to (4bS)-(4balpha,5alpha,10balpha,11alpha)-isomer. calycanthine : The principal alkaloid of the plant family Calycanthaceae.	2.17	1	0	aminal; calycanthaceous alkaloid; organonitrogen heterocyclic compound
catharanthine [no description available]	2.07	1	0	alkaloid ester; bridged compound; methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound; tertiary amino compound
cytochalasin e cytochalasin E: structure	2.07	1	0	cytochalasan alkaloid	metabolite
cytochalasin d [no description available]	2.07	1	0
sinomenine sinomenine: isolated from root of Sinomenium acutum; antirheumatic, antineuralgic	3.59	2	0	morphinane alkaloid
ecdysterone Ecdysterone: A steroid hormone that regulates the processes of MOLTING or ecdysis in insects. Ecdysterone is the 20-hydroxylated ECDYSONE.. 20-hydroxyecdysone : An ecdysteroid that is ecdysone substituted by a hydroxy group at position 20.	2.07	1	0	14alpha-hydroxy steroid; 20-hydroxy steroid; 22-hydroxy steroid; 25-hydroxy steroid; 2beta-hydroxy steroid; 3beta-sterol; ecdysteroid; phytoecdysteroid	animal metabolite; plant metabolite
beryllium Beryllium: An element with the atomic symbol Be, atomic number 4, and atomic weight 9.01218. Short exposure to this element can lead to a type of poisoning known as BERYLLIOSIS.. beryllium atom : Alkaline earth metal atom with atomic number 4.	2.73	3	0	alkaline earth metal atom; elemental beryllium; metal allergen	adjuvant; carcinogenic agent; epitope
bleomycin [no description available]	2.07	1	0	bleomycin	antineoplastic agent; metabolite
boron Boron: A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY.	2.6	1	0	boron group element atom; metalloid atom; nonmetal atom	micronutrient
lavandulol lavandulol: defensive pheromone of the red-lined carrion beetle and additive in perfumes; structure in first source. lavandulol : A monoterpenoid alcohol that is hepta-1-5-diene which is substituted at positions 2 and 6 by methyl groups and at position 3 by a hydroxymethyl group. It is commonly found in lavender oil.	2.08	1	0	lavandulol
bakuchiol bakuchiol: chief component of Psoralea corylifolia Linn; structure	2.07	1	0
demethoxycurcumin demethoxycurcumin: corresponds to curcumin with one methoxy group replaced by hydrogen; isolated from rhizomes of Curcuma longa. demethoxycurcumin : A beta-diketone that is curcumin in which one of the methoxy groups is replaced by hydrogen. It is found in Curcuma zedoaria and Etlingera elatior.	2.11	1	0	beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antineoplastic agent; metabolite
zerumbone zerumbone: RN given for (E,E,E)-isomer; structure in first source. zerumbone : A sesquiterpenoid and cyclic ketone that is (1E,4E,8E)-alpha-humulene which is substituted by an oxo group at the carbon atom attached to two double bonds. It is obtained by steam distillation from a type of edible ginger, Zingiber zerumbet Smith, grown particularly in southeast Asia.	2.07	1	0	cyclic ketone; sesquiterpenoid	anti-inflammatory agent; glioma-associated oncogene inhibitor; plant metabolite
solanesol solanesol : A nonaprenol that is hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-ol substituted by 9 methyl groups at positions 3, 7, 11, 15, 19, 23, 27, 31 and 35 (the all-trans0stereoisomer).	2.07	1	0	nonaprenol; primary alcohol	plant metabolite
xanthoepocin Xanthoepocin: an antibiotic from Penicillium simplicissimum IFO5762; structure in first source	2.17	1	0
pregabalin Pregabalin: A gamma-aminobutyric acid (GABA) derivative that functions as a CALCIUM CHANNEL BLOCKER and is used as an ANTICONVULSANT as well as an ANTI-ANXIETY AGENT. It is also used as an ANALGESIC in the treatment of NEUROPATHIC PAIN and FIBROMYALGIA.. pregabalin : A gamma-amino acid that is gamma-aminobutyric acid (GABA) carrying an isobutyl substitutent at the beta-position (the S-enantiomer). Binds with high affinity to the alpha2-delta site (an auxiliary subunit of voltage-gated calcium channels) in central nervous system tissues.	7.6	1	0	gamma-amino acid	anticonvulsant; calcium channel blocker
oleoyl-coenzyme a oleoyl-coenzyme A: RN given refers to (Z)-isomer	2.06	1	0	octadecenoyl-CoA	Escherichia coli metabolite; mouse metabolite
(1S,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[oxo-(3,4,5-trimethoxyphenyl)methoxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid methyl ester [no description available]	2.07	1	0	yohimban alkaloid
resiniferatoxin resiniferatoxin: phorbol related diterpene ester; potent agonist of vanilloid TRPV1 receptors. resiniferatoxin : A heteropentacyclic compound found in Euphorbia poissonii with molecular formula C37H40O9. It is an agonist of the transient receptor potential cation channel subfamily V member 1 (TrpV1).	3.26	6	0	carboxylic ester; diterpenoid; enone; monomethoxybenzene; organic heteropentacyclic compound; ortho ester; phenols; tertiary alpha-hydroxy ketone	analgesic; neurotoxin; plant metabolite; TRPV1 agonist
n-caproylsphingosine N-(hexanoyl)sphing-4-enine : An N-acylsphingosine consisting of sphing-4-enine bearing a hexanoyl group on nitrogen.	2.07	1	0	N-acylsphingosine
cefotaxime Cefotaxime: Semisynthetic broad-spectrum cephalosporin.. cefotaxime : A cephalosporin compound having acetoxymethyl and [2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups.	2.01	1	0	1,3-thiazoles; cephalosporin; oxime O-ether	antibacterial drug; drug allergen
proguanil Proguanil: A biguanide compound which metabolizes in the body to form cycloguanil, an anti-malaria agent.. proguanil : A biguanide compound which has isopropyl and p-chlorophenyl substituents on the terminal N atoms. A prophylactic antimalarial drug, it works by inhibiting the enzyme dihydrofolate reductase, which is involved in the reproduction of the malaria parasites Plasmodium falciparum and P. vivax within the red blood cells.	2.05	1	0	biguanides; monochlorobenzenes	antimalarial; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor
monorden monorden: inhibits HSP90 Heat-Shock Proteins, DNA topoisomerase VI and human Topoisomerase II	2.07	1	0	cyclic ketone; enone; epoxide; macrolide antibiotic; monochlorobenzenes; phenols	antifungal agent; metabolite; tyrosine kinase inhibitor
ginkgolide b [no description available]	2.07	1	0
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	7.66	3	0	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
homatropine hydrobromide, (endo-(+-)-isomer) [no description available]	2.07	1	0
hydrocotarnine hydrobromide [no description available]	2.07	1	0
salsolinol hydrobromide [no description available]	2.07	1	0
lasalocid sodium lasalocid sodium : The sodium salt of lasalocid. It is a veterinary ionophore antibiotic used for prevention and treatment of coccidiosis in poultry.	2.07	1	0	benzoates; organic sodium salt	coccidiostat; ionophore
sclerotiorin sclerotiorin: isolated from monoverticillate Penicillia; RN given for (R-(R,S-(E,E)))-isomer; structure in first source	2.07	1	0	azaphilone
himbacine himbacine: muscarine receptor antagonist; RN given refers to (3S-(3alpha,3aalpha,4beta(1E,2(2R,6S)),4abeta,8aalpha,9aalpha))-isomer; structure given in first source. himbacine : A piperidine alkaloid that is decahydronaphtho[2,3-c]furan-1(3H)-one substituted by a methyl group at position 3 and a 2-[(2R,6S)-1,6-dimethylpiperidin-2-yl]ethenyl group at position 4. It has been isolated from the bark of Australian magnolias.	2.07	1	0	gamma-lactone; organic heterotricyclic compound; piperidine alkaloid	muscarinic antagonist
ebelactone b ebelactone B: esterase inhibitor; structure given in first source; see also ebelactone A	2.07	1	0
lumefantrine Lumefantrine: A fluorene derivative that is used in combination with ARTEMETHER for the treatment of MALARIA (see ARTEMETHER-LUMEFANTRINE DRUG COMBINATION).. lumefantrine : A member of the class of fluorenes that is 9-(p-chlorobenzylidene)-9H-fluorene which is substitutec by chlorine at positions 2 and 7, and by a 2-(dibutylamino)-1-hydroxyethyl group at position 4. An antimalarial drug used in combination with artemether for the treatment of multi-drug resistant strains of falciparum malaria.	7.41	1	0	fluorenes; monochlorobenzenes; secondary alcohol; tertiary amine	antimalarial
3-o-methylbutein 3-O-methylbutein: RN given refers to (E)-isomer; structure given in first source	2.07	1	0	chalcones
thermozymocidin thermozymocidin: a serine palmitoyltransferase inhibitor; FTY720 is an analog	2.07	1	0	alpha-amino fatty acid; hydroxy monocarboxylic acid; non-proteinogenic alpha-amino acid; sphingoid	antifungal agent; antimicrobial agent; antineoplastic agent; apoptosis inducer; EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor; fungal metabolite; immunosuppressive agent
herboxidiene herboxidiene: structure in first source; isolated from Streptomyces chromofuscus; a potent and selective herbicide (e.g. inactive against wheat); up-regulates the gene expression of LDL receptor	2.17	1	0
pregna-4,17-diene-3,16-dione pregna-4,17-diene-3,16-dione: steroid from guggulu extract; RN & N1 from C1 Form index; RN given refers to cpd without isomeric designation; structure in first source; antagonist of farnesoid X receptor	2.07	1	0	3-hydroxy steroid	androgen
dehydropipernonaline dehydropipernonaline: coronary vasodilator from Piper longum L; structure given in first source	2.45	2	0	benzodioxoles
sanshool sanshool: isolated from the stem bark of Zanthoxylum liebmannianum; RN given for (E,E,Z,E)-isomer; structure in first source	2.08	1	0	fatty amide
valerenic acid valerenic acid: a saturated oplopanone type indene from Valeriana officinalis. valerenic acid : A monocarboxylic acid that is 2-methylprop-2-enoic acid which is substituted at position 3 by a 3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl group. A bicyclic sesquiterpenoid constituent of the essential oil of the Valerian plant.	4.01	3	0	carbobicyclic compound; monocarboxylic acid; sesquiterpenoid	GABA modulator; plant metabolite; sedative; volatile oil component
marein marein: hypoglycemic from Coreopsis tinctoria; structure in first source	2.07	1	0	flavonoids; glycoside
guineensine guineensine: an Acyl-CoA: cholesterol acyltransferase inhibitor, from the fruits of Piper longum; structure in first sourc	3.15	5	0	benzodioxoles
(2E,4E)-N-isobutyl-2,4-dodecadienamide [no description available]	2.73	3	0	fatty amide	metabolite
hydroxysafflor yellow a hydroxysafflor yellow A: from Carthamus tinctorius; structure given in first source. hydroxysafflor yellow A : A C-glycosyl compound that is 3,4,5-trihydroxycyclohexa-2,5-dien-1-one which is substituted by beta-D-glucosyl groups at positions 2 and 4, and by a p-hydroxycinnamoyl group at position 6. It is the main bioactive compound of a traditional Chinese medicine obtained from safflower (Carthamus tinctorius).	2.06	1	0
arvanil arvanil: structure in first source	2.05	1	0	methoxybenzenes; phenols
(1Ar,7aS,10aS,10bS)-1a,5-dimethyl-8-methylidene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one [no description available]	2.17	1	0	germacranolide
isoacteoside isoacteoside: a phenylethanoid glycoside isolated from Indian paintbrush (Verbenaceae) Castilleja linariaefolia; also in other plants; structure given in first source	2.05	1	0	hydroxycinnamic acid
nifuroxime 5-nitro-2-furaldehyde oxime: structure in first source	2.05	1	0
panduratin a panduratin A: isolated from Kaempferia pandurata; structure in first source	2.17	1	0	diarylheptanoid	metabolite
1-methyl-d-lysergic acid butanolamide [no description available]	2.05	1	0	ergot alkaloid; monocarboxylic acid amide	serotonergic antagonist; sympatholytic agent; vasoconstrictor agent
hydroxyachillin hydroxyachillin: isolated from Tanacetum microphyllum; structure given in first source	2.07	1	0	gamma-lactone
nifurtimox Nifurtimox: A nitrofuran thiazine that has been used against TRYPANOSOMIASIS.	2.05	1	0	nitrofuran antibiotic
butylscopolammonium bromide Butylscopolammonium Bromide: Antimuscarinic quaternary ammonium derivative of scopolamine used to treat cramps in gastrointestinal, urinary, uterine, and biliary tracts, and to facilitate radiologic visualization of the gastrointestinal tract.	2.76	3	0
morphinans Morphinans: Compounds based on a partially saturated iminoethanophenanthrene, which can be described as ethylimino-bridged benzo-decahydronaphthalenes. They include some of the OPIOIDS found in PAPAVER that are used as ANALGESICS.	3.19	1	0	isoquinoline alkaloid fundamental parent; morphinane alkaloid
ergoline Ergolines: A series of structurally-related alkaloids that contain the ergoline backbone structure.. ergoline : An indole alkaloid whose structural skeleton is found in many naturally occurring and synthetic ergolines which are known to bind to neurotransmitter receptors, such as dopamine, noradrenaline and serotonin receptors and function as unselective agonists or antagonists at these receptors.	3.19	1	0	diamine; ergoline alkaloid; indole alkaloid fundamental parent; indole alkaloid; organic heterotetracyclic compound
roxithromycin (E)-roxithromycin : A major geometrical isomer of roxithromycin.	2.48	2	0	roxithromycin	environmental contaminant; xenobiotic
fumagillin [no description available]	2.49	2	0	antibiotic antifungal drug; carboxylic ester; dicarboxylic acid monoester; meroterpenoid; organooxygen heterocyclic antibiotic; spiro-epoxide	angiogenesis inhibitor; antibacterial drug; antimicrobial agent; antiprotozoal drug; fungal metabolite; methionine aminopeptidase 2 inhibitor
artesunate artesunic acid: RN given for (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,(2aR*))-isomer; succinic ester of artemether	2.47	2	0	artemisinin derivative; cyclic acetal; dicarboxylic acid monoester; hemisuccinate; semisynthetic derivative; sesquiterpenoid	antimalarial; antineoplastic agent; ferroptosis inducer
(3S,6S,9S,12R)-3-[(2S)-Butan-2-yl]-6-[(1-methoxyindol-3-yl)methyl]-9-(6-oxooctyl)-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone [no description available]	2.17	1	0	oligopeptide
anisodamine [no description available]	2.07	1	0
13-epi-sclareol 13-epi-sclareol: an unusual labdane diterpene from the roots of Coleus forskohlii with cell growth inhibitory action in breast and uterine cancers in vitro; structure in first source	2.17	1	0
bufalin bufalin: cardiotonic; powerful anesthetic & one of the active constituents of the Chinese drug ch'an su(senso); in Japan prepared from skin of Bufo bufo garfarizans; RN given refers to (3beta,5beta)-isomer. bufalin : A 14beta-hydroxy steroid that is bufan-20,22-dienolide having hydroxy substituents at the 5beta- and 14beta-positions. It has been isolated from the skin of the toad Bufo bufo.	2.07	1	0	14beta-hydroxy steroid; 3beta-hydroxy steroid	animal metabolite; anti-inflammatory agent; antineoplastic agent; cardiotonic drug
alpha-solanine [no description available]	2.07	1	0	glycoalkaloid; organic heterohexacyclic compound; steroid saponin; trisaccharide derivative	antineoplastic agent; apoptosis inducer; phytotoxin; plant metabolite
chlorproguanil chlorproguanil: dichloro-derivative of chloroguanide; RN given refers to parent cpd; structure	2.05	1	0	dichlorobenzene
vidofludimus vidofludimus: a dihydroorotate dehydrogenase inhibitor; structure in first source	3.51	1	0
sincalide Sincalide: An octapeptide hormone present in the intestine and brain. When secreted from the gastric mucosa, it stimulates the release of bile from the gallbladder and digestive enzymes from the pancreas.	2.41	1	0	oligopeptide
apigenin-7-o-rutinoside [no description available]	2.07	1	0
gambogic acid gambogic acid: RN given refers to (1R-(1alpha,1(Z),3abeta,5alpha,11beta,14aS*))-isomer	2.07	1	0	pyranoxanthones	metabolite
flag peptide FLAG peptide: engineered as a tag for immunoaffinity purification of genetically-engineered proteins; amino acid sequence given in first source; a polar octapeptide. FLAG peptide : An eight amino acid peptide consisting of L-aspartic acid, L-tyrosine, L-lysine, four L-aspartic acid residues, and L-lysine joined in sequence by peptide linkages. It is widely used as a fusion tag for the purification and detection of a wide variety of recombinant proteins.	2.06	1	0	peptide
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	3.21	5	0	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
bn 52020 [no description available]	2.07	1	0
n1-phenyl-3,5-dinitro-n4,n4-di-n-propylsulfanilamide N1-phenyl-3,5-dinitro-N4,N4-di-n-propylsulfanilamide: a potent, selective antimitotic agent against kinetoplastid parasites; structure in first source	2.05	1	0
n-(4-tert-butylphenyl)-4-(3-chloropyridin-2-yl)tetrahydropyrazine-1(2h)-carboxamide N-(4-tert-butylphenyl)-4-(3-chloropyridin-2-yl)tetrahydropyrazine-1(2H)-carboxamide: a vanilloid receptor 1 antagonist and analgesic; structure in first source	2.48	2	0	piperazines; pyridines
pipernonaline pipernonaline: derived from long pepper, Piper longum; structure in first source	4.26	5	0	benzodioxoles
coumaperine coumaperine: from Piper nigrum (white pepper); structure in first source	2.89	3	0	N-acylpiperidine
artenimol artenimol: derivative of antimalarial drug artemisinin (quinghaosu)	2.05	1	0
carmine carminic acid : A tetrahydroxyanthraquinone that is that is 1,3,4,6-tetrahydroxy-9,10-anthraquinone substituted by a methyl group at position 8, a carboxy group at position 7 and a 1,5-anhydro-D-glucitol moiety at position 2 via a C-glycosidic linkage. It is a natural dye isolated from several insects such as Dactylopius coccus.	2.07	1	0	C-glycosyl compound; monocarboxylic acid; tetrahydroxyanthraquinone	animal metabolite; histological dye
4-phenoxyphenoxyethyl thiocyanate 4-phenoxyphenoxyethyl thiocyanate: has antiparasitic activity; structure in first source	2.05	1	0
alpha-synuclein alpha-Synuclein: A synuclein that is a major component of LEWY BODIES and plays a role in SYNUCLEINOPATHIES, neurodegeneration and neuroprotection.	2.61	2	0
akuammicine akuammicine: from Strychnos sp;; structure in first source. akuammicine : A monoterpenoid indole alkaloid with formula C20H22N2O2, isolated from several plant species including Alstonia spatulata, Catharanthus roseus and Vinca major.	2.17	1	0	methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound; tertiary amino compound	plant metabolite
bavachinin bavachinin: do not confuse with bavachin	2.07	1	0	flavanones
hermitamide b hermitamide B: isolated from Lyngbya majuscula; structure in first source	2.17	1	0
trans-delta-tocotrienoloic acid tocotrienoloic acid: from leaves of Tovomitopsis psychotriifolia; structure given in first source	2.17	1	0	tocotrienol
nodulisporic acid a nodulisporic acid A: a novel indole diterpene insecticide; structure in first source	2.17	1	0
retrofractamide a retrofractamide A: structure in first source	2.96	4	0	benzodioxoles
grayanotoxin iii grayanotoxin III: from leaves of Leucothoe grayana (Ericaceae); RN refers to (3beta,6beta,14R)-isomer; structure given in first source	2.07	1	0
cambogin isogarcinol: has immunosuppresant activity; isolated from Garcinia mangostana; structure in first source	2.11	1	0
acetyl-11-ketoboswellic acid acetyl-11-ketoboswellic acid: a 5-lipoxygenase inhibitor; structure given in first source	2.6	1	0	triterpenoid
Dihydrotanshinone I dihydrotanshinone I: extracted from Radix Salviae	2.07	1	0	abietane diterpenoid	anticoronaviral agent
10-isobutyryloxy-8,9-epoxythymol isobutyrate 10-isobutyryloxy-8,9-epoxythymol isobutyrate: structure in first source	3.51	1	0	benzoate ester; phenols
scopadulcic acid b scopadulcic acid B: isolated from Scorparia dulcis	2.17	1	0
gliocladin c gliocladin C: structure in first source	2.17	1	0
losartan potassium Erythropoietin: Glycoprotein hormone, secreted chiefly by the KIDNEY in the adult and the LIVER in the FETUS, that acts on erythroid stem cells of the BONE MARROW to stimulate proliferation and differentiation.	2.17	1	0
zincophorin zincophorin: 25 carbon polypropionate from Streptomyces griseus; griseochelin and M 144255 are the same monocarboxylic acid ionophore	2.17	1	0	pyrans	bacterial metabolite; ionophore
streptazolin streptazolin: from culture of Streptomyces sp.; structure in first source	2.17	1	0
chatancin chatancin: structure in first source	2.17	1	0
diflucortolone Diflucortolone: A topical glucocorticoid used in various DERMATOSES. It is absorbed through the skin, bound to plasma albumin, and may cause adrenal suppression. It is also administered as the valerate.	2.05	1	0	21-hydroxy steroid
calcimycin Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.	2.46	2	0	benzoxazole
cinobufagin cinobufagin: isolated from Chinese medicinal preparation ch'an su; derived from toad venom	2.07	1	0	steroid lactone
morelloflavone morelloflavone: also inhibits cruzain; RN given for (2S-trans)-isomer; structure in first source. (+)-morelloflavone : A biflavonoid found in Rheedia edulis and Garcinia livingstonei.	2.17	1	0	biflavonoid; hydroxyflavanone; hydroxyflavone	plant metabolite
cinnamosmolide cinnamosmolide: isolated from several species of Canellaceae family; structure in first source	2.17	1	0
atropine sulfate [no description available]	2.07	1	0
cannogenin thevetoside cannogenin thevetoside: from Thevetia neriifolia; minor descriptor (75-84); on-line & Index Medicus search CARDENOLIDES (77-84), CARDANOLIDES (75-76); RN given refers to (3beta,5beta)-isomer	2.07	1	0	cardenolide glycoside
4,5-dihydropiperlonguminine 4,5-dihydropiperlonguminine: in insecticide isolated from Piper tuberculatum; structure in first source	2.45	2	0	benzodioxoles
eriodictyol 7-O-beta-D-glucopyranoside [no description available]	2.07	1	0	beta-D-glucoside; flavanone glycoside; monosaccharide derivative; trihydroxyflavanone	plant metabolite; radical scavenger
15-deoxygoyazensolide 15-deoxygoyazensolide: an NSAID with schistossomicidal and trypanosomicidal activities; structure in first source	2.17	1	0
deoxoartemisinin deoxoartemisinin: structure given in first source	2.05	1	0
hypocrellin a hypocrellin A: isolated from fungus Hypocrella bambusae sacc	2.07	1	0
lyoniside lyoniside: see also eleutherosides & syringin for eleutheroside B: 118-34-3; RN given refers to (3beta)-isomer	2.02	1	0
mitragynine speciogynine: structure in first source	2.17	1	0
amodiaquine hydrochloride [no description available]	2.05	1	0
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.78	3	0
cholecystokinin Cholecystokinin: A peptide, of about 33 amino acids, secreted by the upper INTESTINAL MUCOSA and also found in the central nervous system. It causes gallbladder contraction, release of pancreatic exocrine (or digestive) enzymes, and affects other gastrointestinal functions. Cholecystokinin may be the mediator of satiety.	1.96	1	0
ceruletide Ceruletide: A specific decapeptide obtained from the skin of Hila caerulea, an Australian amphibian. Caerulein is similar in action and composition to CHOLECYSTOKININ. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle. It is used in paralytic ileus and as diagnostic aid in pancreatic malfunction.. ceruletide : A decapeptide comprising 5-oxoprolyl, glutamyl, aspartyl, O-sulfotyrosyl, threonyl, glycyl, tryptopyl, methionyl, aspartyl and phenylalaninamide residues in sequence. Found in the skins of certain Australian amphibians, it is an analogue of the gastrointestinal peptide hormone cholecystokinin and stimulates gastric, biliary, and pancreatic secretion. It is used in cases of paralysis of the intestine (paralytic ileus) and as a diagnostic aid in pancreatic malfunction.	2.06	1	0	oligopeptide	diagnostic agent; gastrointestinal drug
galantide galantide: consists of 20-amino acid residues, 12 AA from the N-terminal of galanin and the C-terminal part of Substance P; blocks the galanin-mediated inhibition of glucose-induced insulin secretion; amino acid sequence given in first source	2.05	1	0
glucagon-like peptide 1 Glucagon-Like Peptide 1: A peptide of 36 or 37 amino acids that is derived from PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. GLP-1(1-37 or 1-36) is further N-terminally truncated resulting in GLP-1(7-37) or GLP-1-(7-36) which can be amidated. These GLP-1 peptides are known to enhance glucose-dependent INSULIN release, suppress GLUCAGON release and gastric emptying, lower BLOOD GLUCOSE, and reduce food intake.	3.95	2	1
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	7.6	1	0	glycoside
adenosine kinase Adenosine Kinase: An enzyme that catalyzes the formation of ADP plus AMP from adenosine plus ATP. It can serve as a salvage mechanism for returning adenosine to nucleic acids. EC 2.7.1.20.	2.17	1	0
valproate sodium Epilim: oral sodium valproate used as antidepressive agent. sodium valproate : The sodium salt of valproic acid.. valproate : A branched-chain saturated fatty acid anion that is the conjugate base of valproic acid.	2.05	1	0	organic sodium salt	geroprotector
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	2.41	1	0
dihydrorobinetin dihydrorobinetin: structure in first source	2.07	1	0
sapogenins Sapogenins: The aglucon moiety of a saponin molecule. It may be triterpenoid or steroid, usually spirostan, in nature.	2.08	1	0
spongia-13(16),14-dien-19-oic acid spongia-13(16),14-dien-19-oic acid : A tetracyclic diterpenoid that is 3b,4,5,5a,6,7,8,9,9a,9b,10,11-dodecahydrophenanthro[1,2-c]furan substituted by methyl groups at positions 3b, 6 and 9 and a carboxy group at position 6. Isolated from Spongia, it exhibits inhibitory activity against androgen receptor.	2.17	1	0	cyclic ether; monocarboxylic acid; tetracyclic diterpenoid	androgen antagonist; metabolite
roquefortine [no description available]	2.17	1	0	pyrroloindole
3-(3,4-dihydroxyphenyl)lactate 3-(3,4-dihydroxyphenyl)lactate : A hydroxy monocarboxylic acid anion that is the conjugate base of 3-(3,4-dihydroxyphenyl)lactic acid; major species at pH 7.3.	2.17	1	0	hydroxy monocarboxylic acid anion
chitosan [no description available]	3.44	6	0
monensin [no description available]	2.07	1	0
sodium glutamate Sodium Glutamate: One of the FLAVORING AGENTS used to impart a meat-like flavor.. monosodium glutamate : An organic sodium salt that is the monosodium salt of glutamic acid.	7.25	1	0	monosodium glutamate	flavouring agent
cortisol succinate, sodium salt hydrocortisone hemisuccinate: RN given refers to (11beta)-isomer; Synonyms Solu-Cortef & sopolcort H refer to Na salt	2.66	2	0	organic molecular entity
marinopyrrole a marinopyrrole A: antibiotic from a marine Streptomyces sp.; structure in first source. (-)-marinopyrrole A : A member of the class of pyrroles that is 1'H-1,3'-bipyrrole substituted by four chloro groups at positions 4, 4', 5 and 5' and two 2-hydroxybenzoyl moieties at positions 2 and 2'. It is isolated from Streptomyces sp.CNQ-418 and exhibits cytotoxic and antibacterial activities.	2.17	1	0	aromatic ketone; organochlorine compound; phenols; pyrroles	antibacterial agent; antimicrobial agent; antineoplastic agent; bacterial metabolite; marine metabolite
picrotoxin Picrotoxin: A noncompetitive antagonist at GABA-A receptors and thus a convulsant. Picrotoxin blocks the GAMMA-AMINOBUTYRIC ACID-activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially the barbiturates.. picrotoxin : A mixture consisting of equimolar amounts of picrotoxinin and picrotin found in the climbing plant Anamirta cocculus.	2.08	1	0
madecassoside [no description available]	2.41	1	0	carboxylic ester; pentacyclic triterpenoid; trisaccharide derivative; triterpenoid saponin	anti-inflammatory agent; antioxidant; antirheumatic drug; plant metabolite; vulnerary
colletoic acid colletoic acid: an 11beta-hydroxysteroid dehydrogenase type 1 inhibitor from Colletotrichum gloeosporioides; structure in first source	2.17	1	0
mannans [no description available]	2.31	1	0
bms-790052 daclatasvir: an HCV NS5A inhibitor. daclatasvir : A member of the class of biphenyls that is a potent inhibitor of nonstructural protein 5A and is used (as its hydrochloride salt) for treatment of hepatitis C.	2.41	1	0	biphenyls; carbamate ester; carboxamide; imidazoles; valine derivative	antiviral drug; nonstructural protein 5A inhibitor
Retrofractamide C [no description available]	2.73	3	0	benzodioxoles
ipomoeassin f ipomoeassin F: a cytotoxic macrocyclic glycoresin from the leaves of Ipomoea squamosa from the Suriname rainforest	2.17	1	0
elafin Elafin: A secretory proteinase inhibitory protein that was initially purified from human SKIN. It is found in a variety mucosal secretions and is present at high levels in SPUTUM. Elafin may play a role in the innate immunity (IMMUNITY, INNATE) response of the LUNG.	2.31	1	0
piperidines Piperidines: A family of hexahydropyridines.	20.04	788	32
6,8-dihydroxy-2,2,4,4-tetramethyl-7-(3-methylbutanoyl)-9-(2-methylpropyl)-9h-xanthene-1,3-dione [no description available]	2.17	1	0	xanthenes
7-hydroxymitragynine 7-hydroxymitragynine: an orally active opioid analgesic from the Thai medicinal herb Mitragyna speciosa; structure in first source	2.17	1	0	alkaloid
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.49	2	0
dorrigocin b dorrigocin B: isolated from the fermentation broth & mycelium of Streptomyces platensis; structure given in first source	2.17	1	0
dorrigocin a dorrigocin A: isolated from the fermentation broth & mycelium of Streptomyces platensis; structure given in first source	2.17	1	0
butyrolactone i butyrolactone I: selective inhibitor of cdk2 & cdc2 kinase; structure given in first source	2.05	1	0	butenolide
tatanan a tatanan A: from the rhizomes of Acorus tatarinowii Schott; structure in first source	2.17	1	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	3.6	8	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
tetracycline Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.	2.05	1	0
oxytetracycline, anhydrous Oxytetracycline: A TETRACYCLINE analog isolated from the actinomycete STREPTOMYCES RIMOSUS and used in a wide variety of clinical conditions.. oxytetracycline : A tetracycline used for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae.	2.05	1	0
minocycline Minocycline: A TETRACYCLINE analog, having a 7-dimethylamino and lacking the 5 methyl and hydroxyl groups, which is effective against tetracycline-resistant STAPHYLOCOCCUS infections.. minocycline : A tetracycline analogue having a dimethylamino group at position 7 and lacking the methyl and hydroxy groups at position 5.	2.47	2	0
dicumarol Dicumarol: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.	2.07	1	0	hydroxycoumarin	anticoagulant; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; Hsp90 inhibitor; vitamin K antagonist
piroxicam [no description available]	2.05	1	0	benzothiazine; monocarboxylic acid amide; pyridines	analgesic; antirheumatic drug; cyclooxygenase 1 inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
mobic Meloxicam: A benzothiazine and thiazole derivative that acts as a NSAID and cyclooxygenase-2 (COX-2) inhibitor. It is used in the treatment of RHEUMATOID ARTHRITIS; OSTEOARTHRITIS; and ANKYLOSING SPONDYLITIS.. meloxicam : A benzothiazine that is piroxicam in which the pyridin-2-yl group is replaced by a 5-methyl-1,3-thiazol-2-yl group. A non-steroidal anti-inflammatory drug and selective inhibitor of COX-2, it is used particularly for the management of rheumatoid arthritis.	2.11	1	0	1,3-thiazoles; benzothiazine; monocarboxylic acid amide	analgesic; antirheumatic drug; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
mobiflex tenoxicam : A thienothiazine-derived monocarboxylic acid amide obtained by formal condensation of the carboxy group of 4-hydroxy-2-methylthieno[2,3-e][1,2]thiazine-3-carboxylic acid 1,1-dioxide with the amino group of 2-aminopyridine. Used for the treatment of pain and inflammation in osteoarthritis and rheumatoid arthritis. It is also indicated for short term treatment of acute musculoskeletal disorders including strains, sprains and other soft-tissue injuries.	2.05	1	0	heteroaryl hydroxy compound; monocarboxylic acid amide; pyridines; thienothiazine	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.21	1	0	benzenes; hydroxycoumarin; methyl ketone
citrinin Citrinin: Antibiotic and mycotoxin from Aspergillus niveus and Penicillium citrinum.	2.46	2	0
rolitetracycline Rolitetracycline: A pyrrolidinylmethyl TETRACYCLINE.. rolitetracycline : A derivative of tetracycline in which the amide function is substituted with a pyrrolidinomethyl group.	2.05	1	0
vulpinic acid vulpinic acid: RN given refers to cpd without isomeric designation; structure given in first source; vulpinic acid refers to (E)-isomer	2.07	1	0	butenolide
ilicicolin h ilicicolin H: structure in first source. ilicicolin H : An aromatic ketone in which the ketone carbonyl group is attached to a (1R,2R,4aS,7S,8aR)-4,7-dimethyl-1-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl group and a 4-hydroxy-5-(4-hydroxyphenyl)-2-oxo-1,2-dihydropyridin-3-yl group. Isolated from the from the "imperfect" fungus Cylindrocladium iliciola strain MFC-870.	2.17	1	0	aromatic ketone; carbobicyclic compound; ilicicolin; monohydroxypyridine; octahydronaphthalenes; phenols; pyridone	antimicrobial agent; mitochondrial respiratory-chain inhibitor
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	2.9	3	0
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	7.25	1	0	ketal
pyrethrins [no description available]	3.08	4	0
ajmaline [no description available]	2.46	2	0
stemofoline stemofoline: RN given for (2S-(2alpha,3beta,4beta,5alpha,5abeta,6beta,8abeta,9S*))-isomer; structure in first source	3.25	1	0
tatanan b tatanan B: from the rhizomes of Acorus tatarinowii Schott; structure in first source	2.17	1	0
colistin sulfate [no description available]	2.11	1	0
gracilioether f gracilioether F: structure in first source	2.17	1	0
cryptocaryol a cryptocaryol A: from Cryptocarya spp.; structure in first source. cryptocaryol A : A member of the class of 2-pyranones that is 5,6-dihydro-2H-pyran-2-one substituted by a 2,4,6,8,10-pentahydroxypentacosyl group at position 6. It has been isolated from Cryptocarya species.	2.17	1	0	2-pyranones; pentol	plant metabolite
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	2.54	2	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.06	1	0
tetrahydroamentoflavone tetrahydroamentoflavone: isolated from Semecarpus anacardium; structure in first source	2.17	1	0
glutamyl-valyl-glycine [no description available]	7.41	1	0	peptide
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	2.01	1	0
silybin Silybin: The major active component of silymarin flavonoids extracted from seeds of the MILK THISTLE, Silybum marianum; it is used in the treatment of HEPATITIS; LIVER CIRRHOSIS; and CHEMICAL AND DRUG INDUCED LIVER INJURY, and has antineoplastic activity; silybins A and B are diastereomers.	7.21	1	0
myelin oligodendrocyte glycoprotein (35-55) [no description available]	2.25	1	0
digitonin Digitonin: A glycoside obtained from Digitalis purpurea; the aglycone is digitogenin which is bound to five sugars. Digitonin solubilizes lipids, especially in membranes and is used as a tool in cellular biochemistry, and reagent for precipitating cholesterol. It has no cardiac effects.. digitonin : A spirostanyl glycoside that is digitogenin in which the 3-hydroxy group is substituted by a beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranosyl group. It is a steroidal saponin isolated from the foxglove plant, Digitalis purpurea. It is used extensively as a mild non-ionic detergent for extracting proteins from membranes for structure and function studies.	2.11	1	0
protopanaxadiol protopanaxadiol: triterpenoid sapogenin of ginsenosides from leaves of Panax ginseng; has antineoplastic activity; acid hydrolysis results in panaxadiol. protopanaxadiol : A tetracyclic triterpenoid sapogenin (isolated from ginseng) that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 positions and in which a double bond has been introduced at the 24-25 position.	7.08	1	0
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	2.31	1	0
kutkin kutkin: alcoholic extract of the root and rrhizome of Picrorhiza kurrooa; has heptatoprotective activity; contains picroside I, kutkoside, and a small amount of other minor glycosides of P. kurrooa	2.04	1	0
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	2.13	1	0	2-aminopurines; oxopurine	antimetabolite; antiviral drug
deoxyguanosine [no description available]	2.06	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	2.05	1	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	10.16	10	1	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor
clozapine Clozapine: A tricylic dibenzodiazepine, classified as an atypical antipsychotic agent. It binds several types of central nervous system receptors, and displays a unique pharmacological profile. Clozapine is a serotonin antagonist, with strong binding to 5-HT 2A/2C receptor subtype. It also displays strong affinity to several dopaminergic receptors, but shows only weak antagonism at the dopamine D2 receptor, a receptor commonly thought to modulate neuroleptic activity. Agranulocytosis is a major adverse effect associated with administration of this agent.. clozapine : A benzodiazepine that is 5H-dibenzo[b,e][1,4]diazepine substituted by a chloro group at position 8 and a 4-methylpiperazin-1-yl group at position 11. It is a second generation antipsychotic used in the treatment of psychiatric disorders like schizophrenia.	2.05	1	0	benzodiazepine; N-arylpiperazine; N-methylpiperazine; organochlorine compound	adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; GABA antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; xenobiotic
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.05	1	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
thiolactomycin thiolactomycin: from actinomycetes; structure given in first source	2.05	1	0
3,4,5-trihydroxybenzamidoxime 3,4,5-trihydroxybenzamidoxime: structure given in first source	2.05	1	0	benzenetriol
nataxazole nataxazole: has antineoplastic activity; isolated from Streptomyces; structure in first source	2.17	1	0
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	2.06	1	0	guanosines	biomarker
aplysinopsin aplysinopsin: antineoplastic tryptophan deriv from Verongia spengetii (marine sponge); structure	2.11	1	0
alpha-cyclopiazonic acid [no description available]	2.07	1	0	alpha-cyclopiazonic acids
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	2.01	1	0
leptin Leptin: A 16-kDa peptide hormone secreted from WHITE ADIPOCYTES. Leptin serves as a feedback signal from fat cells to the CENTRAL NERVOUS SYSTEM in regulation of food intake, energy balance, and fat storage.	4.54	2	2

Condition	Indicated	Relationship Strength	Studies	Trials
Cancer of Colon [description not available]	0	3.19	5	0
Colonic Neoplasms Tumors or cancer of the COLON.	0	3.19	5	0
Adverse Drug Event [description not available]	0	3.36	2	0
American Trypanosomiasis [description not available]	0	2.43	2	0
Chagas Disease Infection with the protozoan parasite TRYPANOSOMA CRUZI, a form of TRYPANOSOMIASIS endemic in Central and South America. It is named after the Brazilian physician Carlos Chagas, who discovered the parasite. Infection by the parasite (positive serologic result only) is distinguished from the clinical manifestations that develop years later, such as destruction of PARASYMPATHETIC GANGLIA; CHAGAS CARDIOMYOPATHY; and dysfunction of the ESOPHAGUS or COLON.	0	2.43	2	0
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	0	3.36	2	0
Liver Dysfunction [description not available]	0	2.04	1	0
Liver Diseases Pathological processes of the LIVER.	0	2.04	1	0
Acute Liver Injury, Drug-Induced [description not available]	0	4.7	9	0
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	0	4.7	9	0
Parasite Infections [description not available]	0	2.05	1	0
Leishmania Infection [description not available]	0	2.46	2	0
Leishmaniasis A disease caused by any of a number of species of protozoa in the genus LEISHMANIA. There are four major clinical types of this infection: cutaneous (Old and New World) (LEISHMANIASIS, CUTANEOUS), diffuse cutaneous (LEISHMANIASIS, DIFFUSE CUTANEOUS), mucocutaneous (LEISHMANIASIS, MUCOCUTANEOUS), and visceral (LEISHMANIASIS, VISCERAL).	0	2.46	2	0
Innate Inflammatory Response [description not available]	0	9.46	37	4
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	0	9.46	37	4
Encephalitis, Polio [description not available]	0	2.06	1	0
Poliomyelitis An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)	0	2.06	1	0
Idiopathic Parkinson Disease [description not available]	0	3.4	6	0
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	0	3.4	6	0
Gastric Ulcer [description not available]	0	4.02	12	0
Stomach Ulcer Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	0	4.02	12	0
Benign Neoplasms [description not available]	0	7.96	17	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	0	7.96	17	0
Anemia, Fanconi [description not available]	0	2.13	1	0
Fanconi Anemia Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)	0	2.13	1	0
Absence Seizure [description not available]	0	3.63	9	0
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	0	3.63	9	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	0	6.14	44	0
Congenital Zika Syndrome [description not available]	0	2.25	1	0
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	0	2.25	1	0
Esophageal Squamous Cell Carcinoma A carcinoma that originates usually from cells on the surface of the middle and lower third of the ESOPHAGUS. Tumor cells exhibit typical squamous morphology and form large polypoid lesions. Mutations in RNF6, LZTS1, TGFBR2, DEC1, and WWOX1 genes are associated with this cancer.	0	3.33	1	0
Cancer of Esophagus [description not available]	0	3.33	1	0
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	0	3.33	1	0
Malignant Melanoma [description not available]	0	3.5	2	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	0	8.5	2	0
Cancer of Stomach [description not available]	0	3.16	4	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	0	3.16	4	0
Breast Cancer [description not available]	0	5.67	16	0
Breast Neoplasms Tumors or cancer of the human BREAST.	0	5.67	16	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	0	5.08	8	1
Cancer of Lung [description not available]	0	3.74	10	0
Lung Neoplasms Tumors or cancer of the LUNG.	0	3.74	10	0
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	0	7.31	1	0
Cancer of Prostate [description not available]	0	3.63	8	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	0	3.63	8	0
Experimental Mammary Neoplasms [description not available]	0	2.83	3	0
Fatty Liver, Nonalcoholic [description not available]	0	6.14	5	5
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	0	6.14	5	5
Cardiovascular Stroke [description not available]	0	4.3	3	1
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	0	9.3	3	1
2019 Novel Coronavirus Disease [description not available]	0	7.49	7	2
Alopecia Cicatrisata [description not available]	0	3.8	1	1
Alopecia Circumscripta [description not available]	0	3.8	1	1
Alopecia Absence of hair from areas where it is normally present.	0	8.8	1	1
Alopecia Areata Loss of scalp and body hair involving microscopically inflammatory patchy areas.	0	8.8	1	1
Hepatocellular Carcinoma [description not available]	0	3.13	4	0
Cancer of Liver [description not available]	0	3.45	6	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	0	3.13	4	0
Liver Neoplasms Tumors or cancer of the LIVER.	0	3.45	6	0
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	0	7.41	1	0
Encephalopathy, Toxic [description not available]	0	2.86	3	0
Congenital Familial Lymphedema [description not available]	0	2.41	1	0
Lymphedema Edema due to obstruction of lymph vessels or disorders of the lymph nodes.	0	2.41	1	0
Apoplexy [description not available]	0	2.41	1	0
Acute Ischemic Stroke [description not available]	0	2.76	2	0
Acute Brain Injuries [description not available]	0	2.41	1	0
Anterior Choroidal Artery Infarction [description not available]	0	2.41	1	0
Ischemic Stroke Stroke due to BRAIN ISCHEMIA resulting in interruption or reduction of blood flow to a part of the brain. When obstruction is due to a BLOOD CLOT formed within in a cerebral blood vessel it is a thrombotic stroke. When obstruction is formed elsewhere and moved to block a cerebral blood vessel (see CEREBRAL EMBOLISM) it is referred to as embolic stroke. Wake-up stroke refers to ischemic stroke occurring during sleep while cryptogenic stroke refers to ischemic stroke of unknown origin.	0	2.76	2	0
Brain Injuries Acute and chronic (see also BRAIN INJURIES, CHRONIC) injuries to the brain, including the cerebral hemispheres, CEREBELLUM, and BRAIN STEM. Clinical manifestations depend on the nature of injury. Diffuse trauma to the brain is frequently associated with DIFFUSE AXONAL INJURY or COMA, POST-TRAUMATIC. Localized injuries may be associated with NEUROBEHAVIORAL MANIFESTATIONS; HEMIPARESIS, or other focal neurologic deficits.	0	2.41	1	0
Cerebral Infarction The formation of an area of NECROSIS in the CEREBRUM caused by an insufficiency of arterial or venous blood flow. Infarcts of the cerebrum are generally classified by hemisphere (i.e., left vs. right), lobe (e.g., frontal lobe infarction), arterial distribution (e.g., INFARCTION, ANTERIOR CEREBRAL ARTERY), and etiology (e.g., embolic infarction).	0	2.41	1	0
Stroke A group of pathological conditions characterized by sudden, non-convulsive loss of neurological function due to BRAIN ISCHEMIA or INTRACRANIAL HEMORRHAGES. Stroke is classified by the type of tissue NECROSIS, such as the anatomic location, vasculature involved, etiology, age of the affected individual, and hemorrhagic vs. non-hemorrhagic nature. (From Adams et al., Principles of Neurology, 6th ed, pp777-810)	0	7.41	1	0
Moniliasis, Oral [description not available]	0	2.41	1	0
Candidiasis, Oral Infection of the mucous membranes of the mouth by a fungus of the genus CANDIDA. (Dorland, 27th ed)	0	2.41	1	0
Cough A sudden, audible expulsion of air from the lungs through a partially closed glottis, preceded by inhalation. It is a protective response that serves to clear the trachea, bronchi, and/or lungs of irritants and secretions, or to prevent aspiration of foreign materials into the lungs.	0	3.8	1	1
Vitiligo A disorder consisting of areas of macular depigmentation, commonly on extensor aspects of extremities, on the face or neck, and in skin folds. Age of onset is often in young adulthood and the condition tends to progress gradually with lesions enlarging and extending until a quiescent state is reached.	0	9.3	3	1
Benign Neoplasms, Brain [description not available]	0	2.66	2	0
Astrocytoma, Grade IV [description not available]	0	3.16	3	0
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	0	2.66	2	0
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	0	3.16	3	0
Acute Edematous Pancreatitis [description not available]	0	2.54	2	0
Acute Disease Disease having a short and relatively severe course.	0	2.58	2	0
Pancreatitis INFLAMMATION of the PANCREAS. Pancreatitis is classified as acute unless there are computed tomographic or endoscopic retrograde cholangiopancreatographic findings of CHRONIC PANCREATITIS (International Symposium on Acute Pancreatitis, Atlanta, 1992). The two most common forms of acute pancreatitis are ALCOHOLIC PANCREATITIS and gallstone pancreatitis.	0	2.54	2	0
Injuries, Spinal Cord [description not available]	0	2.6	1	0
Spinal Cord Injuries Penetrating and non-penetrating injuries to the spinal cord resulting from traumatic external forces (e.g., WOUNDS, GUNSHOT; WHIPLASH INJURIES; etc.).	0	2.6	1	0
Dysphagia [description not available]	0	11.9	5	1
Deglutition Disorders Difficulty in SWALLOWING which may result from neuromuscular disorder or mechanical obstruction. Dysphagia is classified into two distinct types: oropharyngeal dysphagia due to malfunction of the PHARYNX and UPPER ESOPHAGEAL SPHINCTER; and esophageal dysphagia due to malfunction of the ESOPHAGUS.	1	8.9	5	1
Menstruation, Painful [description not available]	0	3.8	1	1
Premenstrual Tension A term used to describe the psychological aspects of PREMENSTRUAL SYNDROME, such as the indescribable tension, depression, hostility, and increased seizure activity in women with seizure disorder.	0	3.8	1	1
Dysmenorrhea Painful menstruation.	0	8.8	1	1
Premenstrual Syndrome A combination of distressing physical, psychologic, or behavioral changes that occur during the luteal phase of the menstrual cycle. Symptoms of PMS are diverse (such as pain, water-retention, anxiety, cravings, and depression) and they diminish markedly 2 or 3 days after the initiation of menses.	0	8.8	1	1
Kahler Disease [description not available]	0	2.41	1	0
Local Neoplasm Recurrence [description not available]	0	2.41	1	0
Multiple Myeloma A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.	0	7.41	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	0	3.94	12	0
Liver Steatosis [description not available]	0	3.04	4	0
Insulin Sensitivity [description not available]	0	4.96	7	1
Fatty Liver Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.	0	3.04	4	0
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	0	4.96	7	1
Acute Confusional Senile Dementia [description not available]	0	4.43	17	0
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	0	4.43	17	0
Alloxan Diabetes [description not available]	0	4.85	11	0
Vascular Diseases Pathological processes involving any of the BLOOD VESSELS in the cardiac or peripheral circulation. They include diseases of ARTERIES; VEINS; and rest of the vasculature system in the body.	0	3.52	4	0
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	0	3.33	4	0
Pneumonia Infection of the lung often accompanied by inflammation.	0	3.33	4	0
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	0	5.13	6	1
DNA Virus Infections Diseases caused by DNA VIRUSES.	0	3.52	4	0
Dermatitis Any inflammation of the skin.	0	3.01	2	0
Encephalopathy, Traumatic [description not available]	0	2.6	1	0
Brain Injuries, Traumatic A form of acquired brain injury which occurs when a sudden trauma causes damage to the brain.	0	2.6	1	0
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.	0	7.76	3	0
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	0	6.87	4	2
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	0	6.87	4	2
Chemo-Fog [description not available]	0	2.6	1	0
Bone Cancer [description not available]	0	2.96	3	0
Osteogenic Sarcoma [description not available]	0	3.18	4	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	0	2.96	3	0
Osteosarcoma A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)	0	3.18	4	0
Diabetes Mellitus, Adult-Onset [description not available]	0	7.74	7	3
Adenoma, beta-Cell [description not available]	0	3.52	1	0
Cancer of Pancreas [description not available]	0	3.52	1	0
Consciousness, Loss of [description not available]	0	3.52	1	0
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	0	7.74	7	3
Insulinoma A benign tumor of the PANCREATIC BETA CELLS. Insulinoma secretes excess INSULIN resulting in HYPOGLYCEMIA.	0	8.52	1	0
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	0	3.52	1	0
Hematologic Malignancies [description not available]	0	2.6	1	0
Leucocythaemia [description not available]	0	2.6	1	0
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	0	2.6	1	0
Hematologic Neoplasms Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.	0	2.6	1	0
Palmoplantaris Pustulosis [description not available]	0	2.6	1	0
Psoriasis A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.	0	2.6	1	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	0	3.6	8	0
Disease Resistance The capacity of an organism to defend itself against pathological processes or the agents of those processes. This most often involves innate immunity whereby the organism responds to pathogens in a generic way. The term disease resistance is used most frequently when referring to plants.	0	4.4	2	1
Anxiety Neuroses [description not available]	0	3.99	1	1
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	0	10.15	5	2
Anxiety Disorders Persistent and disabling ANXIETY.	0	3.99	1	1
Angiogenesis, Pathologic [description not available]	0	4	4	0
Chronic Pancreatitis [description not available]	0	7.21	1	0
Cirrhosis [description not available]	0	2.89	3	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	0	2.89	3	0
Pancreatitis, Chronic INFLAMMATION of the PANCREAS that is characterized by recurring or persistent ABDOMINAL PAIN with or without STEATORRHEA or DIABETES MELLITUS. It is characterized by the irregular destruction of the pancreatic parenchyma which may be focal, segmental, or diffuse.	0	2.21	1	0
Central Nervous System Disease [description not available]	0	3.12	1	0
Central Nervous System Diseases Diseases of any component of the brain (including the cerebral hemispheres, diencephalon, brain stem, and cerebellum) or the spinal cord.	0	3.12	1	0
Atherosclerotic Parkinsonism [description not available]	0	2.58	2	0
Parkinson Disease, Secondary Conditions which feature clinical manifestations resembling primary Parkinson disease that are caused by a known or suspected condition. Examples include parkinsonism caused by vascular injury, drugs, trauma, toxin exposure, neoplasms, infections and degenerative or hereditary conditions. Clinical features may include bradykinesia, rigidity, parkinsonian gait, and masked facies. In general, tremor is less prominent in secondary parkinsonism than in the primary form. (From Joynt, Clinical Neurology, 1998, Ch38, pp39-42)	0	2.58	2	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	0	5.79	7	1
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	0	7.81	3	0
Libman-Sacks Disease [description not available]	0	2.66	2	0
Lupus Erythematosus, Systemic A chronic, relapsing, inflammatory, and often febrile multisystemic disorder of connective tissue, characterized principally by involvement of the skin, joints, kidneys, and serosal membranes. It is of unknown etiology, but is thought to represent a failure of the regulatory mechanisms of the autoimmune system. The disease is marked by a wide range of system dysfunctions, an elevated erythrocyte sedimentation rate, and the formation of LE cells in the blood or bone marrow.	1	4.66	2	0
Cognitive Decline [description not available]	0	2.9	3	0
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	0	7.9	3	0
Anaphylactic Reaction [description not available]	0	2.25	1	0
Anaphylaxis An acute hypersensitivity reaction due to exposure to a previously encountered ANTIGEN. The reaction may include rapidly progressing URTICARIA, respiratory distress, vascular collapse, systemic SHOCK, and death.	0	2.25	1	0
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	0	3.07	4	0
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	0	3.07	4	0
Black Fever [description not available]	0	2.97	4	0
Leishmaniasis, Visceral A chronic disease caused by LEISHMANIA DONOVANI and transmitted by the bite of several sandflies of the genera Phlebotomus and Lutzomyia. It is commonly characterized by fever, chills, vomiting, anemia, hepatosplenomegaly, leukopenia, hypergammaglobulinemia, emaciation, and an earth-gray color of the skin. The disease is classified into three main types according to geographic distribution: Indian, Mediterranean (or infantile), and African.	0	2.97	4	0
Aura [description not available]	0	5.18	10	1
Epilepsy A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)	0	5.18	10	1
Neuralgia, Sciatic [description not available]	0	2.72	2	0
Sciatica A condition characterized by pain radiating from the back into the buttock and posterior/lateral aspects of the leg. Sciatica may be a manifestation of SCIATIC NEUROPATHY; RADICULOPATHY (involving the SPINAL NERVE ROOTS; L4, L5, S1, or S2, often associated with INTERVERTEBRAL DISK DISPLACEMENT); or lesions of the CAUDA EQUINA.	0	2.72	2	0
Invasiveness, Neoplasm [description not available]	0	3.96	4	0
Clinically Isolated CNS Demyelinating Syndrome [description not available]	0	2.25	1	0
Age-Related Memory Disorders [description not available]	0	2.93	3	0
Demyelinating Diseases Diseases characterized by loss or dysfunction of myelin in the central or peripheral nervous system.	0	2.25	1	0
Memory Disorders Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.	0	2.93	3	0
Allergic Encephalomyelitis [description not available]	0	7.69	2	0
Colorectal Cancer [description not available]	0	7.25	1	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	0	2.25	1	0
Cardiac Rupture, Traumatic [description not available]	0	2.55	2	0
Critical Illness A disease or state in which death is possible or imminent.	0	3.64	1	1
Candida Infection [description not available]	0	2.31	1	0
Candidiasis Infection with a fungus of the genus CANDIDA. It is usually a superficial infection of the moist areas of the body and is generally caused by CANDIDA ALBICANS. (Dorland, 27th ed)	0	2.31	1	0
Glial Cell Tumors [description not available]	0	2.25	1	0
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	0	7.25	1	0
Mastitis INFLAMMATION of the BREAST, or MAMMARY GLAND.	0	7.25	1	0
Cardiac Hypertrophy Enlargement of the HEART due to chamber HYPERTROPHY, an increase in wall thickness without an increase in the number of cells (MYOCYTES, CARDIAC). It is the result of increase in myocyte size, mitochondrial and myofibrillar mass, as well as changes in extracellular matrix.	0	2.25	1	0
Cardiomegaly Enlargement of the HEART, usually indicated by a cardiothoracic ratio above 0.50. Heart enlargement may involve the right, the left, or both HEART VENTRICLES or HEART ATRIA. Cardiomegaly is a nonspecific symptom seen in patients with chronic systolic heart failure (HEART FAILURE) or several forms of CARDIOMYOPATHIES.	0	2.25	1	0
Impaired Glucose Tolerance [description not available]	0	2.25	1	0
Glucose Intolerance A pathological state in which BLOOD GLUCOSE level is less than approximately 140 mg/100 ml of PLASMA at fasting, and above approximately 200 mg/100 ml plasma at 30-, 60-, or 90-minute during a GLUCOSE TOLERANCE TEST. This condition is seen frequently in DIABETES MELLITUS, but also occurs with other diseases and MALNUTRITION.	0	2.25	1	0
Chronic Illness [description not available]	0	5.9	8	1
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	0	5.9	8	1
Degenerative Diseases, Central Nervous System [description not available]	0	2.87	3	0
Neurodegenerative Diseases Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.	0	2.87	3	0
Injury, Myocardial Reperfusion [description not available]	0	2.31	1	0
Amentia [description not available]	0	2.69	2	0
Dementia An acquired organic mental disorder with loss of intellectual abilities of sufficient severity to interfere with social or occupational functioning. The dysfunction is multifaceted and involves memory, behavior, personality, judgment, attention, spatial relations, language, abstract thought, and other executive functions. The intellectual decline is usually progressive, and initially spares the level of consciousness.	0	7.69	2	0
Cancer of Nasopharynx [description not available]	0	2.31	1	0
Nasopharyngeal Neoplasms Tumors or cancer of the NASOPHARYNX.	0	2.31	1	0
Granulocytic Leukemia, Chronic [description not available]	0	2.31	1	0
Leukemia, Myelogenous, Chronic, BCR-ABL Positive Clonal hematopoetic disorder caused by an acquired genetic defect in PLURIPOTENT STEM CELLS. It starts in MYELOID CELLS of the bone marrow, invades the blood and then other organs. The condition progresses from a stable, more indolent, chronic phase (LEUKEMIA, MYELOID, CHRONIC PHASE) lasting up to 7 years, to an advanced phase composed of an accelerated phase (LEUKEMIA, MYELOID, ACCELERATED PHASE) and BLAST CRISIS.	0	2.31	1	0
Cancer of Ovary [description not available]	0	2.63	2	0
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	0	2.63	2	0
Eczema, Atopic [description not available]	0	2.41	1	0
Dermatitis, Atopic A chronic inflammatory genetically determined disease of the skin marked by increased ability to form reagin (IgE), with increased susceptibility to allergic rhinitis and asthma, and hereditary disposition to a lowered threshold for pruritus. It is manifested by lichenification, excoriation, and crusting, mainly on the flexural surfaces of the elbow and knee. In infants it is known as infantile eczema.	0	2.41	1	0
Disease, Pulmonary [description not available]	0	2.31	1	0
Lung Diseases Pathological processes involving any part of the LUNG.	0	2.31	1	0
Cerebral Ischemia [description not available]	0	7.66	2	0
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	0	2.66	2	0
Carcinoma, Squamous Cell of Head and Neck [description not available]	0	2.31	1	0
Cancer of Mouth [description not available]	0	2.81	3	0
Squamous Cell Carcinoma of Head and Neck The most common type of head and neck carcinoma that originates from cells on the surface of the NASAL CAVITY; MOUTH; PARANASAL SINUSES, SALIVARY GLANDS, and LARYNX. Mutations in TNFRSF10B, PTEN, and ING1 genes are associated with this cancer.	0	2.31	1	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	0	2.81	3	0
Disease Exacerbation [description not available]	0	3.57	2	0
Carcinoma, Epidermoid [description not available]	0	2.49	2	0
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	0	2.49	2	0
Metastase [description not available]	0	4.62	5	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	0	4.62	5	0
Dyslipidemia [description not available]	0	4.88	2	1
Dyslipidemias Abnormalities in the serum levels of LIPIDS, including overproduction or deficiency. Abnormal serum lipid profiles may include high total CHOLESTEROL, high TRIGLYCERIDES, low HIGH DENSITY LIPOPROTEIN CHOLESTEROL, and elevated LOW DENSITY LIPOPROTEIN CHOLESTEROL.	0	4.88	2	1
Infections, Staphylococcal [description not available]	0	2.51	2	0
Osteomyelitis INFLAMMATION of the bone as a result of infection. It may be caused by a variety of infectious agents, especially pyogenic (PUS - producing) BACTERIA.	0	2.17	1	0
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	0	2.51	2	0
Neuritis A general term indicating inflammation of a peripheral or cranial nerve. Clinical manifestation may include PAIN; PARESTHESIAS; PARESIS; or HYPESTHESIA.	0	2.17	1	0
Cancer of Cervix [description not available]	0	2.51	2	0
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	0	2.51	2	0
Pulmonary Consumption [description not available]	0	4.11	3	1
Tuberculosis, Pulmonary MYCOBACTERIUM infections of the lung.	0	4.11	3	1
Nerve Degeneration Loss of functional activity and trophic degeneration of nerve axons and their terminal arborizations following the destruction of their cells of origin or interruption of their continuity with these cells. The pathology is characteristic of neurodegenerative diseases. Often the process of nerve degeneration is studied in research on neuroanatomical localization and correlation of the neurophysiology of neural pathways.	0	2.5	2	0
Anemia, Cooley's [description not available]	0	3.56	1	1
beta-Thalassemia A disorder characterized by reduced synthesis of the beta chains of hemoglobin. There is retardation of hemoglobin A synthesis in the heterozygous form (thalassemia minor), which is asymptomatic, while in the homozygous form (thalassemia major, Cooley's anemia, Mediterranean anemia, erythroblastic anemia), which can result in severe complications and even death, hemoglobin A synthesis is absent.	0	3.56	1	1
Weight Gain Increase in BODY WEIGHT over existing weight.	0	2.48	2	0
Asthma, Bronchial [description not available]	0	2.49	2	0
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	0	2.49	2	0
Lichen Planus, Oral Oral lesions accompanying cutaneous lichen planus or often occurring alone. The buccal mucosa, lips, gingivae, floor of the mouth, and palate are usually affected (in a descending order of frequency). Typically, oral lesions consist of radiating white or gray, velvety, threadlike lines, arranged in a reticular pattern, at the intersection of which there may be minute, white, elevated dots or streaks (Wickham's striae). (Jablonski, Illustrated Dictionary of Dentistry)	0	3.12	1	0
Glomerulonephritis, Lupus [description not available]	0	2.17	1	0
Lupus Nephritis Glomerulonephritis associated with autoimmune disease SYSTEMIC LUPUS ERYTHEMATOSUS. Lupus nephritis is histologically classified into 6 classes: class I - normal glomeruli, class II - pure mesangial alterations, class III - focal segmental glomerulonephritis, class IV - diffuse glomerulonephritis, class V - diffuse membranous glomerulonephritis, and class VI - advanced sclerosing glomerulonephritis (The World Health Organization classification 1982).	0	7.17	1	0
Pericementitis [description not available]	0	3.47	2	0
Periodontitis Inflammation and loss of connective tissues supporting or surrounding the teeth. This may involve any part of the PERIODONTIUM. Periodontitis is currently classified by disease progression (CHRONIC PERIODONTITIS; AGGRESSIVE PERIODONTITIS) instead of age of onset. (From 1999 International Workshop for a Classification of Periodontal Diseases and Conditions, American Academy of Periodontology)	0	8.47	2	0
Injury, Ischemia-Reperfusion [description not available]	0	2.8	3	0
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	0	7.8	3	0
Cataract, Membranous [description not available]	0	2.21	1	0
Cataract Partial or complete opacity on or in the lens or capsule of one or both eyes, impairing vision or causing blindness. The many kinds of cataract are classified by their morphology (size, shape, location) or etiology (cause and time of occurrence). (Dorland, 27th ed)	0	7.21	1	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	0	4.23	6	0
Familial Nonmedullary Thyroid Cancer [description not available]	0	2.21	1	0
Cancer of Skin [description not available]	0	2.5	2	0
Skin Neoplasms Tumors or cancer of the SKIN.	0	2.5	2	0
Androgen-Independent Prostatic Cancer [description not available]	0	2.21	1	0
Prostatic Neoplasms, Castration-Resistant Tumors or cancer of the PROSTATE which can grow in the presence of low or residual amount of androgen hormones such as TESTOSTERONE.	0	2.21	1	0
Anasarca [description not available]	0	2.78	3	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	0	2.78	3	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	0	2.46	2	0
Colitis Gravis [description not available]	0	2.79	3	0
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	0	2.79	3	0
Hyperlipemia [description not available]	0	3.9	4	0
Hyperlipidemias Conditions with excess LIPIDS in the blood.	0	3.9	4	0
Arthritis, Degenerative [description not available]	0	2.08	1	0
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	0	7.08	1	0
Neurogenic Inflammation Inflammation caused by an injurious stimulus of peripheral neurons and resulting in release of neuropeptides which affect vascular permeability and help initiate proinflammatory and immune reactions at the site of injury.	0	2.15	1	0
Envenomation, Snakebite [description not available]	0	2.1	1	0
Abnormality, Torsion [description not available]	0	2.08	1	0
Ache [description not available]	0	7.92	4	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	1	4.92	4	0
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	0	2.49	2	0
Intestinal Diseases Pathological processes in any segment of the INTESTINE from DUODENUM to RECTUM.	0	2.1	1	0
Colitis, Mucous [description not available]	0	2.08	1	0
Irritable Bowel Syndrome A disorder with chronic or recurrent colonic symptoms without a clearcut etiology. This condition is characterized by chronic or recurrent ABDOMINAL PAIN, bloating, MUCUS in FECES, and an erratic disturbance of DEFECATION.	0	7.08	1	0
Autism [description not available]	0	7.1	1	0
Autistic Disorder A disorder beginning in childhood. It is marked by the presence of markedly abnormal or impaired development in social interaction and communication and a markedly restricted repertoire of activity and interest. Manifestations of the disorder vary greatly depending on the developmental level and chronological age of the individual. (DSM-V)	0	2.1	1	0
Koch's Disease [description not available]	0	2.1	1	0
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	0	7.1	1	0
Depression, Involutional Form of depression in those MIDDLE AGE with feelings of ANXIETY.	0	3.5	1	1
Depressive Disorder, Major Disorder in which five (or more) of the following symptoms have been present during the same 2-week period and represent a change from previous functioning; at least one of the symptoms is either (1) depressed mood or (2) loss of interest or pleasure. Symptoms include: depressed mood most of the day, nearly every daily; markedly diminished interest or pleasure in activities most of the day, nearly every day; significant weight loss when not dieting or weight gain; Insomnia or hypersomnia nearly every day; psychomotor agitation or retardation nearly every day; fatigue or loss of energy nearly every day; feelings of worthlessness or excessive or inappropriate guilt; diminished ability to think or concentrate, or indecisiveness, nearly every day; or recurrent thoughts of death, recurrent suicidal ideation without a specific plan, or a suicide attempt. (DSM-5)	0	3.5	1	1
Airflow Obstruction, Chronic [description not available]	0	3.51	1	1
Bronchiolitis Inflammation of the BRONCHIOLES.	0	3.51	1	1
Pulmonary Disease, Chronic Obstructive A disease of chronic diffuse irreversible airflow obstruction. Subcategories of COPD include CHRONIC BRONCHITIS and PULMONARY EMPHYSEMA.	0	3.51	1	1
Allergic Reaction [description not available]	0	2.1	1	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	0	2.1	1	0
Bowel Diseases, Inflammatory [description not available]	0	2.52	2	0
Inflammatory Bowel Diseases Chronic, non-specific inflammation of the GASTROINTESTINAL TRACT. Etiology may be genetic or environmental. This term includes CROHN DISEASE and ULCERATIVE COLITIS.	0	2.52	2	0
Carcinoma, Small Cell Lung [description not available]	0	2.1	1	0
Small Cell Lung Carcinoma A form of highly malignant lung cancer that is composed of small ovoid cells (SMALL CELL CARCINOMA).	0	2.1	1	0
Biliary Calculi [description not available]	0	2.52	2	0
Gallstones Solid crystalline precipitates in the BILIARY TRACT, usually formed in the GALLBLADDER, resulting in the condition of CHOLELITHIASIS. Gallstones, derived from the BILE, consist mainly of calcium, cholesterol, or bilirubin.	0	2.52	2	0
Osteoarthritis of Knee [description not available]	0	3.51	1	1
Osteoarthritis, Knee Noninflammatory degenerative disease of the knee joint consisting of three large categories: conditions that block normal synchronous movement, conditions that produce abnormal pathways of motion, and conditions that cause stress concentration resulting in changes to articular cartilage. (Crenshaw, Campbell's Operative Orthopaedics, 8th ed, p2019)	0	3.51	1	1
Alveolar Bone Atrophy [description not available]	0	2.11	1	0
Allergic Rhinitis [description not available]	0	7.11	1	0
Rhinitis, Allergic An inflammation of the NASAL MUCOSA triggered by ALLERGENS.	0	2.11	1	0
Infections, Helicobacter [description not available]	0	2.13	1	0
Gastritis Inflammation of the GASTRIC MUCOSA, a lesion observed in a number of unrelated disorders.	0	7.13	1	0
Helicobacter Infections Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.	0	2.13	1	0
Brain Disorders [description not available]	0	2.11	1	0
Brain Diseases Pathologic conditions affecting the BRAIN, which is composed of the intracranial components of the CENTRAL NERVOUS SYSTEM. This includes (but is not limited to) the CEREBRAL CORTEX; intracranial white matter; BASAL GANGLIA; THALAMUS; HYPOTHALAMUS; BRAIN STEM; and CEREBELLUM.	0	2.11	1	0
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	0	3.51	8	0
Autosomal Dominant Juvenile Parkinson Disease [description not available]	0	2.53	2	0
Parkinsonian Disorders A group of disorders which feature impaired motor control characterized by bradykinesia, MUSCLE RIGIDITY; TREMOR; and postural instability. Parkinsonian diseases are generally divided into primary parkinsonism (see PARKINSON DISEASE), secondary parkinsonism (see PARKINSON DISEASE, SECONDARY) and inherited forms. These conditions are associated with dysfunction of dopaminergic or closely related motor integration neuronal pathways in the BASAL GANGLIA.	0	2.53	2	0
Degenerative Disc Disease [description not available]	0	2.11	1	0
Intervertebral Disc Degeneration Degenerative changes in the INTERVERTEBRAL DISC due to aging or structural damage, especially to the vertebral end-plates.	0	2.11	1	0
Experimental Neoplasms [description not available]	0	2.11	1	0
Complication, Postoperative [description not available]	0	2.11	1	0
Root Resorption Resorption in which cementum or dentin is lost from the root of a tooth owing to cementoclastic or osteoclastic activity in conditions such as trauma of occlusion or neoplasms. (Dorland, 27th ed)	0	2.11	1	0
Avulsed Tooth [description not available]	0	2.11	1	0
Postoperative Complications Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery.	0	2.11	1	0
Chronic Lung Injury [description not available]	0	2.13	1	0
Lung Injury, Acute [description not available]	0	2.13	1	0
Edema, Pulmonary [description not available]	0	2.13	1	0
Pulmonary Edema Excessive accumulation of extravascular fluid in the lung, an indication of a serious underlying disease or disorder. Pulmonary edema prevents efficient PULMONARY GAS EXCHANGE in the PULMONARY ALVEOLI, and can be life-threatening.	0	2.13	1	0
Acute Lung Injury A condition of lung damage that is characterized by bilateral pulmonary infiltrates (PULMONARY EDEMA) rich in NEUTROPHILS, and in the absence of clinical HEART FAILURE. This can represent a spectrum of pulmonary lesions, endothelial and epithelial, due to numerous factors (physical, chemical, or biological).	0	7.13	1	0
E coli Infections [description not available]	0	2.11	1	0
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	0	2.11	1	0
Nervous System Disorders [description not available]	0	3.04	1	0
Nervous System Diseases Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.	0	3.04	1	0
Akinetic-Rigid Variant of Huntington Disease [description not available]	0	2.13	1	0
Huntington Disease A familial disorder inherited as an autosomal dominant trait and characterized by the onset of progressive CHOREA and DEMENTIA in the fourth or fifth decade of life. Common initial manifestations include paranoia; poor impulse control; DEPRESSION; HALLUCINATIONS; and DELUSIONS. Eventually intellectual impairment; loss of fine motor control; ATHETOSIS; and diffuse chorea involving axial and limb musculature develops, leading to a vegetative state within 10-15 years of disease onset. The juvenile variant has a more fulminant course including SEIZURES; ATAXIA; dementia; and chorea. (From Adams et al., Principles of Neurology, 6th ed, pp1060-4)	0	2.13	1	0
Infections, Plasmodium [description not available]	0	2.71	3	0
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	0	7.71	3	0
Diabetic Glomerulosclerosis [description not available]	0	2.13	1	0
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	0	2.13	1	0
Protein Aggregation, Pathological A biochemical phenomenon in which misfolded proteins aggregate either intra- or extracellularly. Triggered by factors such as MUTATION; POST-TRANSLATIONAL MODIFICATIONS, and environmental stress, it is generally associated with ALZHEIMER DISEASE; PARKINSON DISEASE; HUNTINGTON DISEASE; and TYPE 2 DIABETES MELLITUS.	0	2.13	1	0
Developmental Coordination Disorder [description not available]	0	2.15	1	0
Atherogenesis [description not available]	0	2.15	1	0
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	0	2.15	1	0
Heart Disease, Ischemic [description not available]	0	2.15	1	0
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	0	7.15	1	0
Graft-Versus-Host Disease [description not available]	0	2.15	1	0
Graft vs Host Disease The clinical entity characterized by anorexia, diarrhea, loss of hair, leukopenia, thrombocytopenia, growth retardation, and eventual death brought about by the GRAFT VS HOST REACTION.	0	2.15	1	0
Blood Pressure, High [description not available]	0	2.49	2	0
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	0	7.49	2	0
Adjuvant Arthritis [description not available]	0	2.77	3	0
Affective Disorders [description not available]	0	2.04	1	0
Mood Disorders Those disorders that have a disturbance in mood as their predominant feature.	0	2.04	1	0
Depression, Endogenous [description not available]	0	2.05	1	0
Depressive Disorder An affective disorder manifested by either a dysphoric mood or loss of interest or pleasure in usual activities. The mood disturbance is prominent and relatively persistent.	0	2.05	1	0
Bronchial Hyperreactivity Tendency of the smooth muscle of the tracheobronchial tree to contract more intensely in response to a given stimulus than it does in the response seen in normal individuals. This condition is present in virtually all symptomatic patients with asthma. The most prominent manifestation of this smooth muscle contraction is a decrease in airway caliber that can be readily measured in the pulmonary function laboratory.	0	2.05	1	0
Allodynia [description not available]	0	2.05	1	0
Cholera Infantum [description not available]	0	2.7	3	0
Gouty Arthritis [description not available]	0	7.06	1	0
Arthritis, Gouty Arthritis, especially of the great toe, as a result of gout. Acute gouty arthritis often is precipitated by trauma, infection, surgery, etc. The initial attacks are usually monoarticular but later attacks are often polyarticular. Acute and chronic gouty arthritis are associated with accumulation of MONOSODIUM URATE in and around affected joints.	0	2.06	1	0
Endotoxin Shock [description not available]	0	2.05	1	0
Shock, Septic Sepsis associated with HYPOTENSION or hypoperfusion despite adequate fluid resuscitation. Perfusion abnormalities may include but are not limited to LACTIC ACIDOSIS; OLIGURIA; or acute alteration in mental status.	0	2.05	1	0
Colonic Inertia Symptom characterized by the passage of stool once a week or less.	0	2.05	1	0
Constipation Infrequent or difficult evacuation of FECES. These symptoms are associated with a variety of causes, including low DIETARY FIBER intake, emotional or nervous disturbances, systemic and structural disorders, drug-induced aggravation, and infections.	0	2.05	1	0
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	0	2.06	1	0
Rodent Diseases Diseases of rodents of the order RODENTIA. This term includes diseases of Sciuridae (squirrels), Geomyidae (gophers), Heteromyidae (pouched mice), Castoridae (beavers), Cricetidae (rats and mice), Muridae (Old World rats and mice), Erethizontidae (porcupines), and Caviidae (guinea pigs).	0	2.06	1	0
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	0	7.06	1	0
Leishmaniasis, American [description not available]	0	2.06	1	0
Leishmaniasis, Cutaneous An endemic disease that is characterized by the development of single or multiple localized lesions on exposed areas of skin that typically ulcerate. The disease has been divided into Old and New World forms. Old World leishmaniasis is separated into three distinct types according to epidemiology and clinical manifestations and is caused by species of the L. tropica and L. aethiopica complexes as well as by species of the L. major genus. New World leishmaniasis, also called American leishmaniasis, occurs in South and Central America and is caused by species of the L. mexicana or L. braziliensis complexes.	0	2.06	1	0
Chromosome-Defective Micronuclei [description not available]	0	2.45	2	0
Anhedonia Inability to experience pleasure due to impairment or dysfunction of normal psychological and neurobiological mechanisms. It is a symptom of many PSYCHOTIC DISORDERS (e.g., DEPRESSIVE DISORDER, MAJOR; and SCHIZOPHRENIA).	0	2.06	1	0
Absence Status [description not available]	0	2.06	1	0
Status Epilepticus A prolonged seizure or seizures repeated frequently enough to prevent recovery between episodes occurring over a period of 20-30 minutes. The most common subtype is generalized tonic-clonic status epilepticus, a potentially fatal condition associated with neuronal injury and respiratory and metabolic dysfunction. Nonconvulsive forms include petit mal status and complex partial status, which may manifest as behavioral disturbances. Simple partial status epilepticus consists of persistent motor, sensory, or autonomic seizures that do not impair cognition (see also EPILEPSIA PARTIALIS CONTINUA). Subclinical status epilepticus generally refers to seizures occurring in an unresponsive or comatose individual in the absence of overt signs of seizure activity. (From N Engl J Med 1998 Apr 2;338(14):970-6; Neurologia 1997 Dec;12 Suppl 6:25-30)	0	2.06	1	0
Weight Reduction [description not available]	0	3.87	2	1
Weight Loss Decrease in existing BODY WEIGHT.	0	3.87	2	1
B16 Melanoma [description not available]	0	2.72	3	0
Cerebral Infarction, Middle Cerebral Artery [description not available]	0	2.07	1	0
Infarction, Middle Cerebral Artery NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.	0	2.07	1	0
Elevated Cholesterol [description not available]	0	2.06	1	0
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	0	2.06	1	0
Ectoparasitic Infestations Infestations by PARASITES which live on, or burrow into, the surface of their host's EPIDERMIS. Most ectoparasites are ARTHROPODS.	0	2.07	1	0
Adenocarcinoma, Basal Cell [description not available]	0	2.08	1	0
Cancer of Rectum [description not available]	0	2.08	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	0	2.08	1	0
Rectal Neoplasms Tumors or cancer of the RECTUM.	0	2.08	1	0
Overweight A status with BODY WEIGHT that is above certain standards. In the scale of BODY MASS INDEX, overweight is defined as having a BMI of 25.0-29.9 kg/m2. Overweight may or may not be due to increases in body fat (ADIPOSE TISSUE), hence overweight does not equal over fat.	0	3.47	1	1
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	0	2.02	1	0
Delayed Hypersensitivity [description not available]	0	2.02	1	0
Sarcoma 180 An experimental sarcoma of mice.	0	7.44	2	0
Bacterial Disease [description not available]	0	2.94	1	0
Bacterial Infections Infections by bacteria, general or unspecified.	0	2.94	1	0
Hepatorenal Syndrome Functional KIDNEY FAILURE in patients with liver disease, usually LIVER CIRRHOSIS or portal hypertension (HYPERTENSION, PORTAL), and in the absence of intrinsic renal disease or kidney abnormality. It is characterized by intense renal vasculature constriction, reduced renal blood flow, OLIGURIA, and sodium retention.	0	2.03	1	0
Leukocytopenia [description not available]	0	2.04	1	0
Leukopenia A decrease in the number of LEUKOCYTES in a blood sample below the normal range (LEUKOCYTE COUNT less than 4000).	0	2.04	1	0
Parasitemia The presence of parasites (especially malarial parasites) in the blood. (Dorland, 27th ed)	0	2.04	1	0
Bladder Diseases [description not available]	0	1.96	1	0
Adrenal Gland Diseases Pathological processes of the ADRENAL GLANDS.	0	1.96	1	0
Abortion, Tubal [description not available]	0	1.96	1	0
Fetal Death Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.	0	2.38	2	0
Pregnancy, Prolonged A term used to describe pregnancies that exceed the upper limit of a normal gestational period. In humans, a prolonged pregnancy is defined as one that extends beyond 42 weeks (294 days) after the first day of the last menstrual period (MENSTRUATION), or birth with gestational age of 41 weeks or more.	0	1.96	1	0
Abortion, Spontaneous Expulsion of the product of FERTILIZATION before completing the term of GESTATION and without deliberate interference.	0	1.96	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	0	1.96	1	0
Plasmodium falciparum Malaria [description not available]	0	1.98	1	0
Malaria, Falciparum Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.	0	1.98	1	0
Experimental Hepatoma [description not available]	0	2.39	2	0
Abscess, Amebic [description not available]	0	1.99	1	0
Amebiasis Infection with any of various amebae. It is an asymptomatic carrier state in most individuals, but diseases ranging from chronic, mild diarrhea to fulminant dysentery may occur.	0	1.99	1	0
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	0	2.01	1	0
Granulomas [description not available]	0	1.97	1	0
Granuloma A relatively small nodular inflammatory lesion containing grouped mononuclear phagocytes, caused by infectious and noninfectious agents.	0	1.97	1	0
Palsy [description not available]	0	1.96	1	0
Paralysis A general term most often used to describe severe or complete loss of muscle strength due to motor system disease from the level of the cerebral cortex to the muscle fiber. This term may also occasionally refer to a loss of sensory function. (From Adams et al., Principles of Neurology, 6th ed, p45)	0	1.96	1	0

piperine

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Research Demand Index: 50.84

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piperine

Description

Related Flora

Cross-References

Synonyms (168)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Occurs in Manufacturing (7 Product(s))

Product Categories

Products

Roles (4)

Drug Classes (4)

Pathways (1)

Protein Targets (87)

Potency Measurements

Inhibition Measurements

Activation Measurements

Other Measurements

Biological Processes (305)

Molecular Functions (101)

Ceullar Components (69)

Bioassays (328)

Research

Studies (895)

Market Indicators

Research Demand Index: 50.84

Study Types

Clinical Trials (12)

Trial Overview

Related Drugs (1,232)

Related Conditions (380)