naringin profile

ID Source	ID
PubMed CID	442428
CHEMBL ID	451532
CHEBI ID	28819
SCHEMBL ID	23432
MeSH ID	M0046707

Synonym
BIDD:ER0262
BRD-K02953697-002-03-3
KBIO1_000247
DIVK1C_000247
smr000059108
MLS000069459
naringenin-7-beta-neohesperidoside
5-hydroxy-2-(4-hydroxyphenyl)-7-(2-o-alpha-l-rhamnopyranosyl-beta-d-glucopyranosyloxy)-4-chromanon
4h-1-benzopyran-4-one, 7-((2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2s)-
ai3-19008
einecs 233-566-4
4',5,7-trihydroxyflavanone 7-rhamnoglucoside
7-(2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavone
4h-1-benzopyran-4-one, 7-((2-o-(6-deoxy-alpha-l-mannapyranosyl)-beta-d-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl), (s)-
PRESTWICK3_000467
ACON1_000139
BSPBIO_000574
naringenin-7-hesperidoside
aurantiin
7-[[2-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl]oxy]-5-hydroxy-2(s)-(4-hydroxyphenyl)-4h-1-benzopyran-4-one
(2s)-7-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
4'5-dioh-flavone-7-rhgluc
IDI1_000247
BPBIO1_000632
MEGXP0_001877
C09789
10236-47-2
naringenin 7-o-[alpha-l-rhamnosyl-(1->2)-beta-d-glucoside]
naringin ,
naringenin 7-o-neohesperidoside
naringenin 7-o-alpha-l-rhamnosyl-(1->2)-beta-d-glucoside
(2s)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2h-chromen-7-yl 2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranoside
CHEBI:28819 ,
PRESTWICK2_000467
NCGC00142617-01
PRESTWICK1_000467
SPBIO_002513
PRESTWICK0_000467
NINDS_000247
(2s)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2h-chromen-7-yl 2-o-(6-deoxy-alpha-l-mannopyranosyl)-betad-glucopyranoside
NCGC00142617-03
NCGC00142617-02
naringenin 7-o-(alpha-l-rhamnosyl-(1,2)-beta-d-glucoside)
bdbm50241582
chembl451532 ,
cid_442428
(s)-7-((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyl-tetrahydro-2h-pyran-2-yloxy)-tetrahydro-2h-pyran-2-yloxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
cid_25075
HMS500M09
(2s)-7-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
naringenin 7-rhamnoglucoside
A800566
4h-1-benzopyran-4-one,7-[[2-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-,(s)-
n7td9j649b ,
unii-n7td9j649b
(2s)-naringin
HMS2231M18
AKOS016034302
naringenine-7-rhamnosidoglucoside
4',5,7-trihydroxyflavanone-7-rhamnoglucoside
naringin extract
naringin [usp-rs]
naringenin-7-rhamnoglucoside
naringin [inci]
naringin [mi]
citrus naringinine [vandf]
7-((2-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one
aurantiin [who-dd]
S2329
(2s)-7-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
gtpl4738
CCG-208591
SCHEMBL23432
DFPMSGMNTNDNHN-ZPHOTFPESA-N
mfcd00148888
DTXSID6022478 ,
(2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one
HY-N0153
sr-01000736681
SR-01000736681-5
SR-01000736681-4
CS-5632
(s)-7-(((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)tetrahydro-2h-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
(2s)-7-[(2s,4s,5s,3r,6r)-3-((2s,6s,3r,4r,5r)-3,4,5-trihydroxy-6-methyl(2h-3,4, 5,6-tetrahydropyran-2-yloxy))-4,5-dihydroxy-6-(hydroxymethyl)(2h-3,4,5,6-tetra hydropyran-2-yloxy)]-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
(s)-7-((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)tetrahydro-2h-pyran-2-yloxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
Q418469
naringin (naringoside)
naringenin,(s)
AS-12929
BRD-K02953697-001-09-2
7-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
XN167836
ZWN ,
(2s)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2h-1-benzopyran-7-yl 2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranoside
naringenin glycoside
naringin (usp-rs)
naringenin 7-o-(alpha-l-rhamnosyl-(1->2)-beta-d-glucoside)
dtxcid302478

Excerpt	Reference	Relevance
"Naringin (NR) is a flavonoid with antineoplastic and anti-inflammatory effects."	( The antifibrotic effects of Kohan, L; Mohammadi, M; Mohammadi, S; Saeidi, M; Saghaeian Jazi, M, 2022)	1.44
"Naringin is a flavonoid with a polyphenolic structure which induces formation of reactive oxygen species (ROS). "	( Naringin generates three types of reactive oxygen species contributing differently to apoptosis-like death in Escherichia coli. Han, G; Lee, DG, 2022)	3.61
"Naringin (NG) is a natural flavanone glycoside, with different phytotherapeutic applications, and its possible protective effects against MTX-induced testicular tissue damage were investigated in this study."	( Beneficial role of naringin against methotrexate-induced injury to rat testes: biochemical and ultrastructural analyses. Abdel-Moneim, AM; Alfwuaires, M; Alzahrani, AM; Elsawy, H; Khalil, M, 2022)	1.77
"Naringin is a naturally occurring flavanone that promotes osteogenesis. "	( TAT&RGD Peptide-Modified Naringin-Loaded Lipid Nanoparticles Promote the Osteogenic Differentiation of Human Dental Pulp Stem Cells. Chen, X; Chu, XY; Gao, CY; He, X; Hu, HY; Yang, K; Zhang, DL; Zheng, CY, 2022)	2.47
"Naringin is a dietary flavonoid glycoside with broad bioactivities, and it has been found to undergo extensive microbial metabolism in human gut. "	( Microbial Metabolism of Naringin and the Impact on Antioxidant Capacity. He, Y; Peng, W; Su, W; Zeng, X; Zhang, J; Zheng, Y, 2022)	2.47
"Naringin is a dihydroflavone which was found in citrus fruits. "	( Exploration of the Protective Mechanism of Naringin in the Acetaminophen-Induced Hepatic Injury by Metabolomics. Cai, Y; Chen, B; Gu, W; Li, M; Lin, Z; Liu, W; Shen, Z; Wan, CC; Wang, G; Yan, T; Zhao, S; Zheng, G, 2022)	2.43
"Naringin is a flavonoid from citrus fruits, especially in grapefruit, which has anti-inflammatory, antioxidant, anti-apoptotic, and neuroprotective activities."	( Naringin enhances long-term potentiation and recovers learning and memory deficits of amyloid-beta induced Alzheimer's disease-like behavioral rat model. Cho, JM; Choi, GY; Ham, YK; Hwang, ES; Kim, HB; Kim, JH; Maeng, S; Mun, MK; Park, HS; Park, JH, 2023)	3.07
"Naringin (NA) is a flavonoid and it has been determined by studies that it has no toxic effect on tissues."	( Effects of naringin on oxidative stress, inflammation, some reproductive parameters, and apoptosis in acrylamide-induced testis toxicity in rat. Aksu, EH; Cinar, İ; Gelen, V; Sengul, E; Yildirim, S, 2023)	2.02
"Naringin (Nar) is a dihydroflavonoid compound, widely found in citrus fruit and used in Chinese herbal medicine. "	( Naringin Alleviates Glucose-Induced Aging by Reducing Fat Accumulation and Promoting Autophagy in Guo, P; Lin, G; Liu, L; Liu, N; Qu, Z; Wang, P; Yu, Z, 2023)	3.8
"Naringin (NAR) is a dihydroflavonoid with various biological activities and pharmacological effects, especially natural antioxidant activity. "	( Naringin regulates intestinal microorganisms and serum metabolites to promote spermatogenesis. Dong, PY; Klinger, FG; Li, L; Liang, SL; Liu, J; Shen, W; Zhang, SE; Zhang, XF, 2023)	3.8
"Naringin is a potent antioxidant and has neuroprotective action which can counteract the redox imbalance induced by sodium fluoride ingestion."	( Neuroprotective effect by naringin against fluorosis-induced neurodegeneration in adult Wistar rats. Cheruku, SP; Kumar, N; Kumar, S; Rao, V; Ravichandiran, V; Shenoy, S; Swamy, RS, 2023)	1.93
"Naringin is a nutritional flavanone glycoside that has been shown to be effective in the treatment of a few chronic disorders associated with ageing."	( Phytochemical Properties, Extraction, and Pharmacological Benefits of Naringin: A Review. Ayaz Mukarram, S; Dar, AH; Dash, KK; Harsányi, E; Kovács, B; Pandey, VK; Shams, R; Shilpa, VS, 2023)	1.87
"Naringin is a polymethoxylated flavonoid commonly found in citrus species and has therapeutic potential in intestinal disorders. "	( Protective Effect of Naringin on In Vitro Gut-Vascular Barrier Disruption of Intestinal Microvascular Endothelial Cells Induced by TNF-α. Bian, Y; Fan, Y; Liu, P; Liu, Z; Zhong, J, 2020)	2.32
"Naringin is a flavonoid widely known for its pharmacological properties, such as: anti-inflammatory and antioxidant ones, being an ally to avoid oxidative damage. "	( Toxicological evaluation of naringin-loaded nanocapsules in vitro and in vivo. Antunes Soares, FA; Boeck, CR; Budel, RG; da Silva, AF; da Silva, DA; da Silva, RS; Dalcin, AJF; Gomes, P; Lopes, LQS; Majolo, JH; Moreira, MP; Nazario, LR; Santos, RCV, 2020)	2.29
"Naringin, a flavonoid, is a major traditional Chinese medicine."	( Protective Effects of Naringin in Cerebral Infarction and Its Molecular Mechanism. Jiang, W; Wang, M; Wen, Y; Xu, D; Yang, J; Yuan, L; Zhou, H, 2020)	1.59
"Naringin is an abundant flavonoid found in citrus fruits with various pharmacological benefits such as antioxidant, anti-inflammatory, and antiapoptotic, activities."	( Protective effects of naringin against drugs and chemical toxins induced hepatotoxicity: A review. Karimi, G; Shirani, K; Shirani, M; Yousefsani, BS, 2020)	1.59
"Naringin is a promising anti-inflammatory drug against various disorders including ulcerative colitis. "	( Colon Targeting of Naringin for Enhanced Cytoprotection Against Indomethacin-Induced Colitis in Rabbits. Borg, TM; El Naggar, EE; El-Sheakh, AR; Hamed, MF; Mohamed, EA, 2020)	2.33
"Naringin is a promising anticancer bioflavonoid phytochemical, mainly extracted from citrus fruits. "	( Naringin induces endoplasmic reticulum stress-mediated apoptosis, inhibits β-catenin pathway and arrests cell cycle in cervical cancer cells. Chen, H; Chen, S; Hu, X; Lin, R; Shi, Q, 2020)	3.44
"Naringin (Nar) is a flavonoid derived from Citrus paradise, and has been shown to possess several pharmacological activities, including free-radical scavenging and antioxidant properties."	( Naringin alleviates methotrexate-induced liver injury in male albino rats and enhances its antitumor efficacy in HepG2 cells. Abdel-Moneim, AM; Alfwuaires, M; Algefare, AI; Elmenshawy, OM; Elsawy, H; Khalil, M; Sedky, A, 2020)	2.72
"Naringin (NAR) is a flavonoid enriched in several medicinal plants and fruits. "	( New Perspectives in the Pharmacological Potential of Naringin in Medicine. Rivoira, MA; Rodriguez, V; Talamoni, G; Tolosa de Talamoni, N, 2021)	2.31
"Naringin (NRG) is a natural, therapeutically active flavanone glycoside with anti-inflammatory, anti-apoptotic, and antioxidant."	( Protective effects of naringin on valproic acid-induced hepatotoxicity in rats. Ates, B; Colak, C; Gunata, M; Koroglu, OF; Parlakpinar, H; Tanriverdi, LH; Vardi, N; Yildiz, A, 2021)	1.66
"Naringin is a dihydroflavonoid abundantly existed in grapefruit and related citrus species. "	( Fertility and early embryonic development toxicity assessment of naringin in Sprague-Dawley rats. Chen, P; Li, P; Peng, W; Su, W; Wang, Y; Wu, H, 2021)	2.3
"Naringin is a flavonoid which has a therapeutic effect. "	( Naringin-generated ROS promotes mitochondria-mediated apoptosis in Candida albicans. Kim, H; Lee, DG, 2021)	3.51
"Naringin is a flavonoid compound, which can be used to treat or prevent various diseases, such as obesity, heart disease, diabetes, and metabolic syndrome. "	( Bioactivity of naringin and related mechanisms. Liu, S; Zhao, Y, 2021)	2.42
"Naringin is a bioflavonoid, very abundantly found in citrus species. "	( The beneficial role of Naringin- a citrus bioflavonoid, against oxidative stress-induced neurobehavioral disorders and cognitive dysfunction in rodents: A systematic review and meta-analysis. Moolemath, Y; Shylaja, H; Viswanatha, GL, 2017)	2.21
"Naringin (NR) is a flavanone glycoside extracted from grapefruits and citrus fruits. "	( Naringin attenuates thioacetamide-induced liver fibrosis in rats through modulation of the PI3K/Akt pathway. Eissa, LA; El-Karef, A; El-Mihi, KA; Elsherbiny, NM; Kenawy, HI, 2017)	3.34
"Naringin is a bio-flavonoid."	( Naringin Protects Against High Glucose-Induced Human Endothelial Cell Injury Via Antioxidation and CX3CL1 Downregulation. Gao, Y; Guo, J; Jiang, H; Li, G; Liang, S; Liu, H; Rao, S; Sheng, X; Tan, M; Wang, J; Xu, Y; Yu, Y; Zheng, C; Zhong, Q; Zhu, G, 2017)	2.62
"Naringin is a grapefruit-derived flavonoid with anti-diabetic, anti-dyslipidemia, anti-inflammatory and anti-oxidant activities."	( Naringin prevents HIV-1 protease inhibitors-induced metabolic complications in vivo. Nzuza, S; Owira, PMO; Zondi, S, 2017)	2.62
"Naringin (NG) is a natural flavanone glycoside that has pharmacological and therapeutic activities, such as anti-inflammation, anti-apoptotic, and antioxidant properties."	( Naringin protects against cyclophosphamide-induced hepatotoxicity and nephrotoxicity through modulation of oxidative stress, inflammation, apoptosis, autophagy, and DNA damage. Caglayan, C; Kandemir, FM; Kucukler, S; Temel, Y; Yildirim, S, 2018)	2.64
"Naringin is a naturally occurring flavanone with recognized neuroprotective, cardioprotective, anti-inflammatory, and antiosteoporotic properties. "	( Bioinstructive Naringin-Loaded Micelles for Guiding Stem Cell Osteodifferentiation. Gaspar, VM; Lavrador, P; Mano, JF, 2018)	2.28
"Naringin was found to be an effective antidiabetic agent which increased Insulin gene expression and insulin secretion by upregulating the PDX-1 gene and protein expression."	( Naringin (4',5,7-Trihydroxyflavanone 7-Rhamnoglucoside) Attenuates β-Cell Dysfunction in Diabetic Rats through Upregulation of PDX-1. Chandra Sekaran, SP; Jyothi, AK; Subramanian, M; Sundaramurthi, I; Thotakura, B, 2018)	3.37
"Naringin (NG) is a natural bioflavonoid that have been reported to have many medicinal and pharmacological properties."	( The effects of naringin on different cyclophosphamide-induced organ toxicities in rats: investigation of changes in some metabolic enzyme activities. Caglayan, C, 2019)	1.59
"Naringin palmitate is a modified product of naringin that is produced by an acylation reaction with palmitic acid, which is considered to be an effective substance for enhancing naringin lipophilicity."	( Investigation of the interaction of naringin palmitate with bovine serum albumin: spectroscopic analysis and molecular docking. Huang, J; Li, B; Li, L; Liang, Z; Su, J; Xu, Z; Zhang, X, 2013)	1.39
"Naringin is a major flavonoid found in grapefruit and an active compound extracted from a Chinese herbal medicine (Rhizoma Drynariae)."	( Naringin promotes osteoblast differentiation and effectively reverses ovariectomy-associated osteoporosis. Jiang, Y; Li, N; Wooley, PH; Xu, Z; Yang, SY, 2013)	2.55
"Naringin is a major flavonoid identified in grapefruit."	( Therapeutic potentials of naringin on polymethylmethacrylate induced osteoclastogenesis and osteolysis, in vitro and in vivo assessments. Li, N; Wooley, PH; Xu, Z; Yang, SY; Zhang, J, 2014)	1.42
"Naringin is a flavonoid showing variable pharmacological properties and is distributed ubiquitously in plant foods. "	( Six months chronic toxicological evaluation of naringin in Sprague-Dawley rats. Cen, X; Guan, X; Hu, C; Li, P; Peng, W; Su, W; Wang, S; Wang, Y, 2014)	2.1
"Naringin is a potent antioxidant, which can cross the blood brain barrier protecting brain tissue and modulating brain chemistry."	( Naringin ameliorates memory deficits in experimental paradigm of Alzheimer's disease by attenuating mitochondrial dysfunction. Chopra, K; Kuhad, A; Sachdeva, AK, 2014)	2.57
"Naringin is a bioflavonoid present in the grapefruit."	( Naringin ameliorates pentylenetetrazol-induced seizures and associated oxidative stress, inflammation, and cognitive impairment in rats: possible mechanisms of neuroprotection. Arya, DS; Bhatia, J; Chaudhry, U; Golechha, M; Saluja, D; Sarangal, V, 2014)	2.57
"Naringin (Nar) is a major and active flavanone glycoside derivative of several citrus species. "	( Naringin protects against anoxia/reoxygenation-induced apoptosis in H9c2 cells via the Nrf2 signaling pathway. Chen, RC; Sun, GB; Sun, XB; Wang, J; Zhang, HJ, 2015)	3.3
"Naringin is a flavonoid found in grapefruit and other citrus fruits that shows antioxidant activity. "	( Anti-genotoxic effect of naringin against bleomycin-induced genomic damage in human lymphocytes in vitro. Bilaloglu, R; Çinkilic, N; Teksoy, O; Yilmaz, D, 2016)	2.18
"Naringin is a dihydrotestosterone flavonoid compound that significantly inhibits bone loss, improves bone density, and enhances biomechanical anti‑compression performance. "	( Naringin promotes differentiation of bone marrow stem cells into osteoblasts by upregulating the expression levels of microRNA-20a and downregulating the expression levels of PPARγ. Fan, J; Fan, Q; Li, J, 2015)	3.3
"Naringin is a naturally existing compound in citrus fruits and has been elucidated to promote bone development and maintenance."	( Stimulation of Wnt/β-Catenin Signaling to Improve Bone Development by Naringin via Interacting with AMPK and Akt. Dong, J; Ma, W; Sun, B; Wang, B; Wang, D; Wang, F, 2015)	2.09
"Naringin is a natural dietary flavonoid compound. "	( Naringin, a natural dietary compound, prevents intestinal tumorigenesis in Apc (Min/+) mouse model. Cui, SX; Jiang, T; Li, C; Li, Y; Qu, XJ; Sun, SY; Wang, Y; Zhang, YS, 2016)	3.32
"Naringin is a potential chemopreventive agent for reducing the risk of colonic cancers."	( Naringin, a natural dietary compound, prevents intestinal tumorigenesis in Apc (Min/+) mouse model. Cui, SX; Jiang, T; Li, C; Li, Y; Qu, XJ; Sun, SY; Wang, Y; Zhang, YS, 2016)	2.6
"Naringin (Nar) is a flavonoid with a molecular mass of 580 Da."	( Sandwich enzyme-linked immunosorbent assay for naringin. Cheng, J; Kong, H; Qu, B; Qu, H; Shan, W; Wang, Q; Wang, X; Zhang, Y; Zhao, Y, 2016)	1.41
"Naringin is a bioflavonoid and has free radical scavenging and anti-inflammatory properties."	( Naringin protects ultraviolet B-induced skin damage by regulating p38 MAPK signal pathway. Dang, Y; Li, X; Ren, X; Shi, Y; Xu, M; Ye, X; Zhao, D, 2016)	3.32
"Naringin is a natural flavanone glycoside that is found in the Chinese herbal medicines and citrus fruits. "	( Therapeutic potential of naringin: an overview. Chen, R; Li, QY; Qi, QL; Wang, MT, 2016)	2.18
"Naringin is a promising candidate for further in vivo studies and clinical use. "	( Therapeutic potential of naringin: an overview. Chen, R; Li, QY; Qi, QL; Wang, MT, 2016)	2.18
"Naringin (Nar) is a bioflavonoid that has antioxidant activity and suppresses MMP-9 expression."	( Effects of naringin on physical fatigue and serum MMP-9 concentration in female rats. Allahtavakoli, M; Amirteimouri, M; Elshiekh, M; Hajizadeh, M; Moemenzadeh, M; Shamsizadeh, A; Zamanian, M, 2017)	1.57
"Naringin is a bioflavonoid that is rich in citrus plants and possesses enormous health benefits. "	( Structural characterization and bioavailability of ternary nanoparticles consisting of amylose, α-linoleic acid and β-lactoglobulin complexed with naringin. Feng, T; Liu, F; Wang, K; Xu, Z; Ye, R; Zhu, X; Zhuang, H, 2017)	2.1
"Naringin (Nar) is a flavonoid that has shown antigenotoxic effect against the chromosome damage induced by various compounds. "	( Effect of naringin on the DNA damage induced by daunorubicin in mouse hepatocytes and cardiocytes. Alvarez-González, I; Cariño-Cortés, R; Madrigal-Bujaidar, E; Martino-Roaro, L, 2010)	2.21
"Naringin is a bioflavonoid derivative and is predominantly found in Citrus paradisi Macf., Citrus sinensis (Linn.) Osbeck, Citrus unshiu Marc., Citrus reticulata Blanco cv. "	( Inhibition of TNF-α/IFN-γ induced RANTES expression in HaCaT cell by naringin. Liao, L; Ling, Z; Si-Si, W; Yun-Xia, Y, 2011)	2.05
"Naringin is a dietary flavonoid from citrus fruits with antioxidant and antiapoptotic activity. "	( Inhibition of Ca(2+) entry and suicidal erythrocyte death by naringin. Lang, F; Shaik, N; Zbidah, M, 2012)	2.06
"Naringin is a flavonoid available commonly in citrus fruits and is also a HMG-CoA reductase inhibitor. "	( Effect of naringin collagen graft on bone formation. Rabie, AB; Wong, RW, 2006)	2.18
"Naringin is a flavonoid that exists in many plants and traditional Chinese medicines. "	( A rapid LC/MS/MS quantitation assay for naringin and its two metabolites in rats plasma. Bai, Y; Fang, T; Ma, Y; Su, W; Wang, Y; Zhao, P, 2006)	2.04
"Naringin is a flavonoid that is commonly found in grapefruits. "	( The inhibitory effects of naringin on the growth of periodontal pathogens in vitro. Rabie, AB; Tsui, VW; Wong, RW, 2008)	2.09
"Naringin (Nar) is a flavonone found in high amount in grapefruit. "	( Inhibitory effect of naringin on the micronuclei induced by ifosfamide in mouse, and evaluation of its modulatory effect on the Cyp3a subfamily. Alvarez-González, I; Dorado, V; Espinosa-Aguirre, JJ; Madrigal-Bujaidar, E, 2001)	2.07

Excerpt	Reference	Relevance
"Naringin has an active principle called flavonoid that has been found to have medicinal properties, mostly because of its antioxidant and metal chelating properties."	( Naringin administration mitigates oxidative stress, anemia, and hypertension in lead acetate-induced cardio-renal dysfunction in cockerel chicks. Adedapo, AA; Adetona, MO; Ebirim, CG; Esan, O; Oguntibeju, OO; Oladele, OA; Omobowale, TO; Oyagbemi, AA; Yakubu, MA, 2023)	3.07
"The Naringin-BG hydrogel has an adequate swelling ratio that encourages the fusion of tissue formed with host tissue and enables the gradual release of Naringin bioavailabilities enhanced"	( Thermo-responsive injectable naringin-loaded hydrogel polymerised sodium alginate/bioglass delivery for articular cartilage. Li, L; Li, X; Lu, Y; Wang, Y; Zhao, F; Zhou, S, 2021)	1.39
"Naringin (Nar) has been reported to exert potential hepatoprotective effects against acetaminophen (APAP)-induced injury. "	( Naringin regulates mitochondrial dynamics to protect against acetaminophen-induced hepatotoxicity by activating the AMPK/Nrf2 signaling pathway in vitro. Bi, Y; Chen, Y; Duan, Z; Guo, W; Li, Z; Wu, Q; Yu, P, 2022)	3.61
"Naringin (Nr) has been identified to have antidepressant-like effects through repeated treatment. "	( Antidepressant-like effect of acute dose of Naringin involves suppression of NR1 and activation of protein kinase A/cyclic adenosine monophosphate response element-binding protein/brain-derived neurotrophic factor signaling in hippocampus. Mei, X; Wang, G; Yang, H; Zuo, W, 2023)	2.61
"Naringin has an active principle called flavonoid that has been found to have medicinal properties, mostly because of its antioxidant and metal chelating properties."	( Naringin administration mitigates oxidative stress, anemia, and hypertension in lead acetate-induced cardio-renal dysfunction in cockerel chicks. Adedapo, AA; Adetona, MO; Ebirim, CG; Esan, O; Oguntibeju, OO; Oladele, OA; Omobowale, TO; Oyagbemi, AA; Yakubu, MA, 2023)	3.07
"Naringin has been shown to have a variety of biological, medicinal, and pharmacological effects."	( Phytochemical Properties, Extraction, and Pharmacological Benefits of Naringin: A Review. Ayaz Mukarram, S; Dar, AH; Dash, KK; Harsányi, E; Kovács, B; Pandey, VK; Shams, R; Shilpa, VS, 2023)	1.87
"Naringin has been documented to possess multiple pharmacological activities. "	( Tissue distribution of naringin and derived metabolites in rats after a single oral administration. He, Y; Li, P; Rao, H; Su, W; Yao, H; Zeng, X; Zheng, Y, 2020)	2.31
"Naringin (NG) has been proved to have numerous notable biological effects, including anti-inflammatory effect, anti-cancer effect, and anti-ulcer effect, yet there are no clinical preparations of naringin due to its poor solubility and low dissolution rate after oral administration. "	( Naringin-loaded polymeric micelles as buccal tablets: formulation, characterization, Fan, H; Jin, Z; Lin, R; Liu, Y; Ma, J; Mo, F; Zhang, J; Zhang, P; Zhou, L, 2020)	3.44
"Naringin has anti-inflammatory effect in macrophages."	( Naringin inhibits titanium particles-induced up-regulation of TNF-α and IL-6 via the p38 MAPK pathway in fibroblasts from hip periprosthetic membrane. Liu, W; Qian, Y; Shan, H; Yang, C; Yu, X; Zeng, B; Zhang, X, 2021)	2.79
"The Naringin-BG hydrogel has an adequate swelling ratio that encourages the fusion of tissue formed with host tissue and enables the gradual release of Naringin bioavailabilities enhanced"	( Thermo-responsive injectable naringin-loaded hydrogel polymerised sodium alginate/bioglass delivery for articular cartilage. Li, L; Li, X; Lu, Y; Wang, Y; Zhao, F; Zhou, S, 2021)	1.39
"Naringin has been reported to exhibit a variety of biological effects."	( Naringin attenuates MLC phosphorylation and NF-κB activation to protect sepsis-induced intestinal injury via RhoA/ROCK pathway. Gao, M; Li, Z; Liu, Z; Wang, K; Xiao, X; Yang, B; Yang, M; Zhang, H, 2018)	2.64
"Naringin (Nar) has been reported to possess various biological activities and pharmacological properties."	( Naringin mitigates myocardial strain and the inflammatory response in sepsis-induced myocardial dysfunction through regulation of PI3K/AKT/NF-κB pathway. Cui, L; Qiao, W; Ren, WD; Sun, LJ; Wang, X; Xiao, YJ, 2019)	2.68
"Naringin has antioxidant properties that could improve redox-sensitive myocardial ischemia reperfusion (IR) injury. "	( Regulation of heat shock proteins 27 and 70, p-Akt/p-eNOS and MAPKs by Naringin Dampens myocardial injury and dysfunction in vivo after ischemia/reperfusion. Arya, DS; Bharti, S; Chauhan, SS; Kumari, S; Manchanda, M; Nag, TC; Rani, N; Ray, R, 2013)	2.07
"Naringin has been reported to possess a wild range of biological activities. "	( [Metabolism of naringin produced by intestinal bacteria]. Duan, JA; Guan, HL; Jiang, S; Qian, DW; Qian, YF; Ren, H; Shang, EX; Zhang, W, 2013)	2.19
"Naringin has been reported to possess diverse pharmacological properties, including anti-arthritic and anti-inflammatory activities. "	( Naringin attenuates the development of carrageenan-induced acute lung inflammation through inhibition of NF-κb, STAT3 and pro-inflammatory mediators and enhancement of IκBα and anti-inflammatory cytokines. Abd-Allah, AR; Abdel-Hamied, HE; Ahmad, SF; Ansari, MA; Ashour, AE; Attia, SM; Bakheet, SA; Korashy, HM; Zoheir, KM, 2015)	3.3
"Naringin has been shown to increase osteoblast proliferation by increasing the expression of BMP-2, inhibit osteoclast activity by reducing the expression of RANKL."	( [Research progress on Drynaria fortunei naringin on inflammation and bone activity]. Xiao, LB; Yin, FM; Zhang, Y, 2015)	1.41
"Naringin has been reported to posses biological functions which are beneficial to human cognitions, but its protective effects on HFD-induced cognitive deficits and underlying mechanisms have not been well characterized."	( Naringin Improves Neuronal Insulin Signaling, Brain Mitochondrial Function, and Cognitive Function in High-Fat Diet-Induced Obese Mice. Chen, J; Wang, D; Wang, Y; Wu, W; Yan, J; Zhu, X, 2015)	2.58
"Naringin has been reported to have an anti-atherosclerosis effect but the underlying mechanism is not fully understood. "	( The Anti-Atherosclerotic Effect of Naringin Is Associated with Reduced Expressions of Cell Adhesion Molecules and Chemokines through NF-κB Pathway. Bi, KW; Hsueh, TP; Huang, CC; Huang, ST; Pang, JH; Sheen, JM; Wu, HT, 2016)	2.15
"Naringin (Nar) has antioxidant and anti-inflammatory properties. "	( Naringin lauroyl ester inhibits lipopolysaccharide-induced activation of nuclear factor κB signaling in macrophages. Hattori, H; Ihara, H; Nakazawa, M; Sakamoto, T; Tsutsuki, H; Ueda, M, 2016)	3.32
"Naringin has various biological activities in LPS-induced sepsis."	( Naringin protects against lipopolysaccharide-induced cardiac injury in mice. Lan, PZ; Qiufang, L; Wenqi, H; Xianchu, L; Xiangcheng, R; Yang, D; Yi, L, 2016)	2.6
"Naringin has been reported as an effective anti-inflammatory compound. "	( Naringin attenuates acute lung injury in LPS-treated mice by inhibiting NF-κB pathway. Chen, JL; Li, PB; Liu, Y; Nie, YC; Su, WW; Wu, H, 2011)	3.25
"Naringin has been reported to act as an effective anti-inflammatory compound. "	( Naringin inhibits chemokine production in an LPS-induced RAW 264.7 macrophage cell line. Li, PB; Liu, Y; Su, WW; Wang, S, 2012)	3.26

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"Naringin promotes the proliferation and differentiation of BMSCs, and increases osteocalcin expression. "	( Naringin promotes osteoblast differentiation and effectively reverses ovariectomy-associated osteoporosis. Jiang, Y; Li, N; Wooley, PH; Xu, Z; Yang, SY, 2013)	3.28
"Naringin could inhibit osteoclast differentiation, bone absorption function and proliferation activity of osteoclasts, significantly down-regulate RANK, TRAP, MMP-9 and NFATc1 mRNA expressions in the osteoclast differentiation process, and up-regulate the C-fos mRNA expression."	( [Effect of naringin on osteoclast differentiation]. Li, FB; Li, YJ; Ma, JX; Ma, XL; Sun, XL; Zhang, Y; Zhao, B, 2015)	2.25
"Naringin could inhibit osteoclast differentiation, proliferation and bone absorption function. "	( [Effect of naringin on osteoclast differentiation]. Li, FB; Li, YJ; Ma, JX; Ma, XL; Sun, XL; Zhang, Y; Zhao, B, 2015)	2.25
"Naringin could increase the expression of Sema3A and the activation of Wnt/β-catenin signalling to prevent disuse osteoporosis induced by denervation."	( Naringin ameliorates bone loss induced by sciatic neurectomy and increases Semaphorin 3A expression in denervated bone. Li, F; Li, Y; Lv, J; Ma, J; Ma, X; Sun, L; Sun, X; Wang, J; Wang, Y; Xing, G; Zhao, Z, 2016)	2.6
"Naringin effectively promotes the proliferation of degenerative human NP cells and improves the recuperation of the cells from degeneration by increasing expression of aggrecan, BMP-2, and Sox6 while inhibiting the expression of TNF-α and MMP3. "	( Therapeutic effects of naringin on degenerative human nucleus pulposus cells for discogenic low back pain. Heggeness, M; Li, N; Whitaker, C; Xu, Z; Yang, SY, 2016)	2.19
"Naringin can suppress high glucose-induced vascular inflammation possibly by inhibiting ROS production and NF-kappaB activation in HUVECs."	( [Naringin inhibits monocyte adhesion to high glucose-induced human umbilical vein endothelial cells]. Rao, JJ; Wang, GF; Wu, SG; Wu, SY; Xiong, Y; Xu, W; Zhang, JJ; Zhang, JY, 2010)	2.71
"Naringin can inhibit the increased production of RANTES, which is partially via NF-κB-dependent signal pathway."	( Inhibition of TNF-α/IFN-γ induced RANTES expression in HaCaT cell by naringin. Liao, L; Ling, Z; Si-Si, W; Yun-Xia, Y, 2011)	2.05
"Naringin was found to inhibit RANKL-induced activation of NF-κB by suppressing RANKL-mediated IκB-α degradation."	( Naringin abrogates osteoclastogenesis and bone resorption via the inhibition of RANKL-induced NF-κB and ERK activation. Ang, ES; Chen, H; Liu, Q; Xu, J; Yang, X; Zheng, MH, 2011)	2.53

Excerpt	Reference	Relevance
"Naringin pretreatment significantly decreased the cytokine release and apoptosis of cardiomyocytes exposed to OGD/R. "	( Naringin attenuates acute myocardial ischemia-reperfusion injury via miR- 126/GSK-3β/β-catenin signaling pathway. Guo, X; Ji, Q; Ma, W; Wu, M, 2022)	3.61
"The naringin-treated group showed reduced body weight, biochemical parameters, and the mRNA expressions of protein degradation."	( Naringin Ameliorates Skeletal Muscle Atrophy and Improves Insulin Resistance in High-Fat-Diet-Induced Insulin Resistance in Obese Rats. Malakul, W; Phetrungnapha, A; Termkwancharoen, C; Tunsophon, S, 2022)	2.64
"And naringin treatment reduced apoptosis of nerve cells in rat hippocampus and the secretion of inflammatory factor such as TNF-alpha and IL-6."	( Protective Effects of Naringin in Cerebral Infarction and Its Molecular Mechanism. Jiang, W; Wang, M; Wen, Y; Xu, D; Yang, J; Yuan, L; Zhou, H, 2020)	1.35
"Naringin pretreatment significantly and concentration-dependently inhibited ox-LDL-induced cell injury and apoptosis."	( Naringin protects endothelial cells from apoptosis and inflammation by regulating the Hippo-YAP Pathway. Liu, H; Liu, M; Lu, C; Suo, R; Zhao, H, 2020)	2.72
"Naringin treated AGS cells showed up-regulating BH3 domain Bad, down-regulating Bcl-xL, and Bad phosphorylation and significant mitochondrial fluorescence intensity expression."	( Naringin Induces Lysosomal Permeabilization and Autophagy Cell Death in AGS Gastric Cancer Cells. Ha, SE; Kim, GS; Kim, SM; Lee, HJ; Lee, WS; Raha, S; Saralamma, VV; Yumnam, S, 2020)	2.72
"Naringin treatment resulted in a dose-dependent significant (p < 0.05) decrease in the levels of plasma cholesterol and triglyceride from 84.84 ± 1.62 to 55.59 ± 1.50 mg/dL and 123.03 ± 15.11 to 55.00 ± 0.86 mg/dL, respectively, at 200 mg/kg naringin."	( Naringin enhances reverse cholesterol transport in high fat/low streptozocin induced diabetic rats. Adelani, IB; Bankole, GE; Rotimi, OA; Rotimi, SO, 2018)	2.64
"Naringin-treated mice exhibited normalized structures of colorectal tissues."	( Natural dietary compound naringin prevents azoxymethane/dextran sodium sulfate-induced chronic colorectal inflammation and carcinogenesis in mice. Cui, SX; Qu, XJ; Wang, F; Zhang, YS, 2018)	1.51
"Naringin treatment reduced the oxidative stress in bone from DEX-treated IBD rats."	( Naringin protects against bone loss in steroid-treated inflammatory bowel disease in a rat model. Ge, X; Li, C; Li, G; Lv, F; Zhang, J, 2018)	2.64
"Naringin-treated diabetic rats showed significantly increased mRNA expression of Pdx-1 and Insulin genes, increased expression of transcription factor PDX-1, and higher serum insulin levels than the diabetic control animals."	( Naringin (4',5,7-Trihydroxyflavanone 7-Rhamnoglucoside) Attenuates β-Cell Dysfunction in Diabetic Rats through Upregulation of PDX-1. Chandra Sekaran, SP; Jyothi, AK; Subramanian, M; Sundaramurthi, I; Thotakura, B, 2018)	2.64
"Naringin pretreatment of cells significantly inhibited the activation of p65/NF-κB in a concentration-dependent manner."	( Naringin inhibits lipopolysaccharide-induced activation of microglia cells. Bai, J; Li, C; Li, S; Liu, H; Ma, L; Wu, G; Zhang, P, 2019)	2.68
"Naringin treatment also markedly decreased calcium release in the stimulated cell culture medium."	( Therapeutic potentials of naringin on polymethylmethacrylate induced osteoclastogenesis and osteolysis, in vitro and in vivo assessments. Li, N; Wooley, PH; Xu, Z; Yang, SY; Zhang, J, 2014)	1.42
"Naringin (100mg/kg) treatment along with gentamicin restored the mitochondrial function and increased the renal endogenous antioxidant status."	( Naringin ameliorates gentamicin-induced nephrotoxicity and associated mitochondrial dysfunction, apoptosis and inflammation in rats: possible mechanism of nephroprotection. Borkar, RM; Koneru, M; Kumar, JM; Kuncha, M; Sahu, BD; Shyam Sunder, R; Sistla, R; Srinivas, R; Tatireddy, S, 2014)	2.57
"Naringin treated with plasma exhibited antimicrobial activity against foodborne pathogens, especially Salmonella Typhimurium; an activity that was absent before plasma treatment."	( Effect of atmospheric pressure dielectric barrier discharge plasma on the biological activity of naringin. Choe, W; Jo, C; Kim, HJ; Kim, K; Kim, TH; Park, S; Yong, HI, 2014)	1.34
"Naringin treatment at 40 and 80 mg/kg resulted in significant (P<0.05) up-regulation of mRNA expression of growth factor (IFG-1, TGF-β and VEGF-c), Ang-1 and collagen-1 whereas mRNA expression of inflammatory mediators (TNF-α, IL-1β and IL-6) was down-regulated."	( Naringin, a flavanone glycoside, promotes angiogenesis and inhibits endothelial apoptosis through modulation of inflammatory and growth factor expression in diabetic foot ulcer in rats. Bodhankar, SL; Ghosh, P; Kandhare, AD, 2014)	2.57
"Naringin treatment enhances the antioxidant defense by increasing the activities of enzymatic antioxidants and the level of reduced glutathione."	( Neuroprotective efficacy of naringin on 3-nitropropionic acid-induced mitochondrial dysfunction through the modulation of Nrf2 signaling pathway in PC12 cells. Ganapasam, S; Kulasekaran, G, 2015)	1.43
"Naringin treatment of diabetic rats significantly reversed oxidative stress, lipid peroxidation, proteins oxidation, CH indices, and JNK protein activation compared with untreated diabetic animals."	( Naringin Mitigates Cardiac Hypertrophy by Reducing Oxidative Stress and Inactivating c-Jun Nuclear Kinase-1 Protein in Type I Diabetes. Adebiyi, AO; Adebiyi, OO; Owira, PM, 2016)	2.6
"Naringin treatment also markedly blocked the activation of p38 in response to UVB stimulation in the mouse skin."	( Naringin protects ultraviolet B-induced skin damage by regulating p38 MAPK signal pathway. Dang, Y; Li, X; Ren, X; Shi, Y; Xu, M; Ye, X; Zhao, D, 2016)	2.6
"Naringin treatment significantly ameliorated these changes in diabetic rats compared to the untreated diabetic controls."	( Naringin Reduces Hyperglycemia-Induced Cardiac Fibrosis by Relieving Oxidative Stress. Adebiyi, OA; Adebiyi, OO; Owira, PM, 2016)	2.6
"Naringin pretreatment significantly decreased (p < 0.05) serum creatinine, blood urea nitrogen, bilirubin, aspartate transaminase, alanine transaminase, lactate dehydrogenase, low-density lipoprotein, very low-density lipoprotein, cholesterol and triglycerides as compared with APAP control rats. "	( Ameliorative effect of naringin in acetaminophen-induced hepatic and renal toxicity in laboratory rats: role of FXR and KIM-1. Adil, M; Bodhankar, SL; Ghosh, P; Kandhare, AD; Raygude, KS; Venkata, S, 2016)	2.19
"Naringin treatment significantly improved Fasting Plasma Insulin (FPI), hepatic glycogen content, malondialdehyde, β-hydroxybutyrate, acetoacetate, bicarbonate, blood pH and anion gap but not Fasting Blood Glucose (FBG) compared to the STZ only-treated group."	( Grapefruit Derived Flavonoid Naringin Improves Ketoacidosis and Lipid Peroxidation in Type 1 Diabetes Rat Model. Cobongela, SZ; Driver, C; Miruka, DO; Murunga, AN; Nkomo, FS; Owira, PM, 2016)	1.45
"Naringin treatment induced the suppression of cell growth toward HeLa and A549 cells accompanied with an increase of apoptotic cells."	( NEU3 inhibitory effect of naringin suppresses cancer cell growth by attenuation of EGFR signaling through GM3 ganglioside accumulation. Chigwechokha, PK; Ikeda, A; Kajiya, N; Kamada, Y; Kibe, T; Kishida, M; Kishida, S; Komatsu, M; Oishi, K; Shiozaki, K; Yoshinaga, A, 2016)	1.46
"Naringin treatment resulted in significant inhibition of TNF-α, but elevated protein expressions of BMP-2, collagen II, and aggrecan."	( Therapeutic effects of naringin on degenerative human nucleus pulposus cells for discogenic low back pain. Heggeness, M; Li, N; Whitaker, C; Xu, Z; Yang, SY, 2016)	1.47
"Naringintreated HepG2 cells underwent apoptosis also in a concentration related manner, determined by annexin Vfluorescein isothiocyanate (FITC) and propidium iodide (PI) employing flow cytometry."	( Induction of Human Hepatocellular Carcinoma HepG2 Cell Apoptosis by Naringin. Banjerdpongchai, R; Khawon, P; Wudtiwai, B, 2016)	1.39
"Naringin treatment resulted in significant growth inhibition and G(1)-phase cell cycle arrest mediated by induction of p53-independent p21WAF1 expression; expression of cyclins and CDKs in VSMCs was also down-regulated."	( Naringin-induced p21WAF1-mediated G(1)-phase cell cycle arrest via activation of the Ras/Raf/ERK signaling pathway in vascular smooth muscle cells. Choi, WS; Kim, WJ; Lee, EJ; Moon, GS; Moon, SK, 2008)	2.51
"Naringin treatment significantly attenuated acetylcholine esterase activity in D-galactose treated mice."	( Naringin alleviates cognitive impairment, mitochondrial dysfunction and oxidative stress induced by D-galactose in mice. Dogra, S; Kumar, A; Prakash, A, 2010)	2.52
"Naringin treatment ameliorated the antioxidant status by increasing the activities of enzymic antioxidants and the levels of non-enzymatic antioxidants."	( Neuroprotective effect of naringin, a dietary flavonoid against 3-nitropropionic acid-induced neuronal apoptosis. Gopinath, K; Prakash, D; Sudhandiran, G, 2011)	1.39
"Naringin treatment may help to overcome the iron-induced toxic effects in vitro."	( Influence of naringin on ferric iron induced oxidative damage in vitro. Jagetia, GC; Kedlaya, R; Reddy, TK; Venkatesha, VA, 2004)	1.41
"Naringin pretreatment significantly altered the pharmacokinetic parameters of verapamil."	( Effect of naringin pretreatment on bioavailability of verapamil in rabbits. Choi, JS; Yeum, CH, 2006)	1.46
"Naringin treatment resulted in significant dose-dependent growth inhibition together with G(1)-phase cell-cycle arrest at a dose of 100 microM (the half maximal inhibitory concentration) in 5637 cells."	( Requirement for Ras/Raf/ERK pathway in naringin-induced G1-cell-cycle arrest via p21WAF1 expression. Kim, DI; Kim, WJ; Lee, SB; Lee, SJ; Moon, SK; Park, K, 2008)	1.34
"Naringin-treated rats showed a marked increase in hexosamine levels, but this increase was less in animals pretreated with indomethacin."	( Antiulcer effect of naringin on gastric lesions induced by ethanol in rats. Franco, JM; Marhuenda, E; Martín, MJ; Pérez-Guerrero, C, 1994)	1.33
"Naringin treatment inhibited hypercholesterolemia-induced intercellular adhesion molecule-1 (ICAM-1) expression on endothelial cells."	( Naringin has an antiatherogenic effect with the inhibition of intercellular adhesion molecule-1 in hypercholesterolemic rabbits. Bok, SH; Choe, SC; Jeong, TS; Kim, HS; Park, YB, 2001)	2.47
"Treatment with naringin corrected anemia, reduced oxidative stress, improved antioxidant system, reduced high blood pressure, and offered protection against lead acetate-induced cardio-renal dysfunction in cockerel chicks."	( Naringin administration mitigates oxidative stress, anemia, and hypertension in lead acetate-induced cardio-renal dysfunction in cockerel chicks. Adedapo, AA; Adetona, MO; Ebirim, CG; Esan, O; Oguntibeju, OO; Oladele, OA; Omobowale, TO; Oyagbemi, AA; Yakubu, MA, 2023)	2.69
"Treatment with naringin and/or naringenin reduced the abnormally high serum levels of total bilirubin, aspartate transaminase, alanine transaminase, alkaline phosphatase, lactate dehydrogenase, and gamma-glutamyl transferase in Taxol-treated rats."	( Naringin and naringenin counteract taxol-induced liver injury in Wistar rats via suppression of oxidative stress, apoptosis and inflammation. Abdel-Gabbar, M; Ahmed, NA; Ahmed, OM; El-Nahass, ES; Khaled, SS; Soliman, HA, 2023)	2.69
"Pretreatment with naringin significantly (p < 0.05) abolish CYCP-induced changes in the activities of serum and hepatic ALT, AST, GGT, ALP, and LDH."	( Naringin prevents cyclophosphamide-induced hepatotoxicity in rats by attenuating oxidative stress, fibrosis, and inflammation. Adeleye, OO; Akamo, AJ; Akinloye, DI; Amah, G; Cole, OE; Dosumu, OA; Eteng, OE; Obijeku, A; Rotimi, SO; Ugbaja, RN, 2021)	2.39
"Oral treatment of naringin at a doses of 20, 40 and 80 mg/kg body weight to diabetic rats for 30 days resulted in a significant reduction in the levels of plasma glucose, blood glycosylated hemoglobin and increase in the levels of plasma insulin and blood hemoglobin."	( Modulatory effects of naringin on hepatic key enzymes of carbohydrate metabolism in high-fat diet/low-dose streptozotocin-induced diabetes in rats. Chandramohan, R; Pari, L, 2017)	1.09
"Treatment with naringin markedly protected against the steroid‑induced decrease in serum osteocalcin levels, and the rate of osteonecrosis in a model of SANFH."	( Naringin protects against steroid‑induced avascular necrosis of the femoral head through upregulation of PPARγ and activation of the Notch signaling pathway. Chen, B; Chen, Y; Ding, W; Fang, G; Huang, D; Li, F; Li, Z; Sun, X; Xu, H, 2018)	2.26
"Treatment with naringin facilitated the EPC tube formation capacity and increased the levels of CXCL12, CXCR4 and pAkt (P < 0.05) relative to those in the control group."	( Naringin enhances endothelial progenitor cell (EPC) proliferation and tube formation capacity through the CXCL12/CXCR4/PI3K/Akt signaling pathway. Li, F; Lv, J; Ma, J; Ma, X; Sun, X; Zhao, Z, 2018)	2.26
"Pre-treatment with naringin produced the same results."	( Naringin ameliorates the high glucose-induced rat mesangial cell inflammatory reaction by modulating the NLRP3 Inflammasome. Chen, F; Ma, X; Wang, Q; Wei, G; Xu, J, 2018)	2.24
"Treatment with naringin (40 and 80 mg/kg) significantly and dose-dependently restored (p < 0.01 and p < 0.001) altered levels of kidney (serum creatinine, urine creatinine, BUN, uric acid, and creatinine clearance) and liver function test (AST and ALT) induced by sodium arsenite."	( Naringin ameliorates sodium arsenite-induced renal and hepatic toxicity in rats: decisive role of KIM-1, Caspase-3, TGF-β, and TNF-α. Adil, M; Bodhankar, SL; Kandhare, AD; Visnagri, A, 2015)	2.2
"Treatment with naringin (40 and 80 mg/kg, p.o.) significantly restored (p < 0.05) these altered myocardial functions. "	( Sodium arsenite-induced myocardial bruise in rats: Ameliorative effect of naringin via TGF-β/Smad and Nrf/HO pathways. Adil, M; Bodhankar, SL; Ghosh, P; Kandhare, AD, 2016)	1.02
"Treatment with naringin protected RIN-5F cells from PI-induced oxidative damage and apoptosis."	( Naringin protects against HIV-1 protease inhibitors-induced pancreatic β-cell dysfunction and apoptosis. Ndwandwe, DE; Nzuza, S; Owira, PMO, 2016)	2.22
"Treatment with naringin attenuated the alterations in the renal and urine markers, decreasing lipid peroxidation markers, increasing the antioxidant cascade and decreasing the nickel concentration in blood and kidney."	( Beneficial role of naringin, a flavanoid on nickel induced nephrotoxicity in rats. Amudha, K; Pari, L, 2011)	1.04
"Treatment with naringin ameliorated these biochemical markers dose-dependently."	( Evaluation of chromosomal instability in diabetic rats treated with naringin. A Bakheet, S; M Attia, S, 2011)	0.94
"Treatment with naringin ameliorated the reduced glutathione/oxidized glutathione ratio with concomitant decrease in the levels of hydroxyl radical, hydroperoxide and nitrite in 3-NP-induced rats."	( Naringin modulates oxidative stress and inflammation in 3-nitropropionic acid-induced neurodegeneration through the activation of nuclear factor-erythroid 2-related factor-2 signalling pathway. Gopinath, K; Sudhandiran, G, 2012)	2.16
"Pretreatment with naringin (10, 20, and 40 mg/kg) for a period of 56 days significantly decreased the levels of total, ester, and free cholesterol, TG, FFA in serum and heart and increased PL in heart."	( Preventive effect of naringin on lipids, lipoproteins and lipid metabolic enzymes in isoproterenol-induced myocardial infarction in Wistar rats. Rajadurai, M; Stanely Mainzen Prince, P, 2006)	0.98
"Pretreatment with naringin (10, 20 or 40mg/kg) daily for a period of 56 days positively altered the levels of cTnT, intensity of the bands of the LDH1 and LDH2-isoenzyme and the activities of cardiac marker enzymes, ECG-patterns and lysosomal hydrolases in ISO-induced rats."	( Preventive effect of naringin on cardiac markers, electrocardiographic patterns and lysosomal hydrolases in normal and isoproterenol-induced myocardial infarction in Wistar rats. Rajadurai, M; Stanely Mainzen Prince, P, 2007)	0.98
"Pretreatment with naringin for a period of 56 days exhibited a significant (P<0.05) effect and altered these biochemical parameters positively in ISO-induced rats."	( Preventive effect of naringin on isoproterenol-induced cardiotoxicity in Wistar rats: an in vivo and in vitro study. Prince, PS; Rajadurai, M, 2007)	0.98
"Treatment with naringin 3 h prior to lipopolysaccharide challenge resulted in complete protection from lipopolysaccharide lethality in D-galactosamine-sensitized mice."	( Suppression of lipopolysaccharide-induced tumor necrosis factor-release and liver injury in mice by naringin. Hasegawa, H; Kawaguchi, K; Kikuchi, S; Kumazawa, Y; Maruyama, H; Morita, H, 1999)	0.86

Excerpt	Reference	Relevance
" The toxic effect of nickel was also indicated by significantly decreased activities of enzymatic antioxidants like superoxide dismutase, catalase, glutathione peroxidase, glutathione-S-transferase, glutathione reductase and glucose-6-phosphate dehydrogenase and non-enzymatic antioxidants like reduced glutathione, total sulfhydryl groups, vitamin C and vitamin E levels were significantly decreased."	( Hepatoprotective role of naringin on nickel-induced toxicity in male Wistar rats. Amudha, K; Pari, L, 2011)	0.67
"A major problem with cancer chemotherapy is its severe toxic effects on non-target tissues."	( Heated naringin mitigate the genotoxicity effect of Mitomycin C in BALB/c mice through enhancing the antioxidant status. Chaaban, H; Chekir-Ghedira, L; Ghedira, K; Ghoul, M; Ioannou, I; Maatouk, M; Mokdad-Bzeouich, I; Mustapha, N, 2018)	0.94
" The flavonoids are gaining critical attention in the management of PD due to the toxic effects of the synthetic drugs."	( Naringin Exhibits Neuroprotection Against Rotenone-Induced Neurotoxicity in Experimental Rodents. Agrawal, N; Garabadu, D, 2020)	2
" Though several drug candidates have been developed in the management of AD, an alternative option is still required due to serious adverse effects of the former."	( Naringin Exhibits Mas Receptor-Mediated Neuroprotection Against Amyloid Beta-Induced Cognitive Deficits and Mitochondrial Toxicity in Rat Brain. Garabadu, D; Varshney, V, 2021)	2.06
" VPA has been reported to be associated with many adverse effects, including hepatotoxicity."	( Protective effects of naringin on valproic acid-induced hepatotoxicity in rats. Ates, B; Colak, C; Gunata, M; Koroglu, OF; Parlakpinar, H; Tanriverdi, LH; Vardi, N; Yildiz, A, 2021)	0.94
" Naringin (NA) is a flavonoid and it has been determined by studies that it has no toxic effect on tissues."	( Effects of naringin on oxidative stress, inflammation, some reproductive parameters, and apoptosis in acrylamide-induced testis toxicity in rat. Aksu, EH; Cinar, İ; Gelen, V; Sengul, E; Yildirim, S, 2023)	2.21
"5-fluorouracil (5-FU) is an efficacious fluoropyrimidine antimetabolite anticancer drug, however, its clinical utility is constrained due to side effect toxicity on delicate organs, including the heart."	( Naringin ameliorates 5-fluorouracil induced cardiotoxicity: An insight into its modulatory impact on oxidative stress, inflammatory and apoptotic parameters. Famurewa, AC; Gui, Y; Olatunji, OJ, 2023)	2.35

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" Pharmacokinetic parameters of camptothecin were assessed using a non-compartmental model."	( Effect of P-glycoprotein modulators on the pharmacokinetics of camptothecin using microdialysis. Lee, CH; Tsai, TH; Yeh, PH, 2001)	0.31
" The pharmacokinetic parameters were calculated by using WINNONLIN."	( Comparison of metabolic pharmacokinetics of naringin and naringenin in rabbits. Chao, PD; Chin, DH; Hou, YC; Hsiu, SL; Huang, TY, 2002)	0.58
" For both NF and NS, subjects who ingested grapefruit 1 h before drug administration exhibited a greater Cmax and AUC0-24 than did subjects in the control group."	( [Effect of grapefruit pulp on the pharmacokinetics of the dihydropyridine calcium antagonists nifedipine and nisoldipine]. Itou, K; Kariya, S; Kasuyama, K; Kawabata, S; Kotaki, H; Morikawa, A; Nishida, N; Ohtani, M; Seo, I; Uchino, K, 2002)	0.31
"The present study evaluated the pharmacokinetics of three different grapefruit flavanone forms in dog plasma and demonstrated their absorption after an oral intake of a grapefruit extract; pharmacokinetic parameters of these forms were also determined."	( Absorption and pharmacokinetics of grapefruit flavanones in beagles. Andrés-Lacueva, C; Escribano, E; Jáuregui, O; Lamuela-Raventós, RM; Mata-Bilbao, Mde L; Roura, E; Torre, C, 2007)	0.34
"SAP can significantly impact the absorption of DCQD components in rats and their pharmacokinetic parameters."	( Effect of severe acute pancreatitis on pharmacokinetics of Da-Cheng-Qi Decoction components. Chen, GY; Gong, HL; Huang, X; Liang, MZ; Tang, WF; Xia, Q; Xiang, J; Yu, Q, 2009)	0.35
" Safety and pharmacokinetic analyses were performed."	( Intestinal OATP1A2 inhibition as a potential mechanism for the effect of grapefruit juice on aliskiren pharmacokinetics in healthy subjects. Alexander, N; Dahlke, M; Hanna, I; Hariry, S; Jarugula, V; Rebello, S; Vapurcuyan, A; Zhao, S, 2012)	0.38
" The validated method was applied to a pharmacokinetic study in rats after oral administration of Si-Ni-San decoction."	( UPLC-MS/MS determination of paeoniflorin, naringin, naringenin and glycyrrhetinic acid in rat plasma and its application to a pharmacokinetic study after oral administration of Si-Ni-San decoction. Li, F; Liu, X; Liu, Z; Qiao, Y; Song, Y; Wen, J; Yang, J, 2012)	0.64
" The levels of aloe-emodin, rhein, emodin, chrysophanol, honokiol, magnolol, hesperidin, and naringin in rat serum were quantified using a liquid chromatography tandem mass spectrometry (LC-MS/MS) method for pharmacokinetic study."	( Effect of formula compatibility on the pharmacokinetics of components from Dachengqi Decoction [See Text] in rats. Chen, GY; Gong, HL; Huang, X; Tang, WF; Wang, J, 2012)	0.6
"The area under the curve (AUC), mean retention time (MRT), the peak concentration (C(max)) of aloe-emodin, rhein, emodin, and chrysophanol in the DCQD group were significantly different compared with the Dahuang group (P <0."	( Effect of formula compatibility on the pharmacokinetics of components from Dachengqi Decoction [See Text] in rats. Chen, GY; Gong, HL; Huang, X; Tang, WF; Wang, J, 2012)	0.38
"The compatibility in Chinese medicine could affect the drug's pharmacokinetics in DCQD, which proves that the prescription compatibility principle of Chinese medicine formulations has its own pharmacokinetic basis."	( Effect of formula compatibility on the pharmacokinetics of components from Dachengqi Decoction [See Text] in rats. Chen, GY; Gong, HL; Huang, X; Tang, WF; Wang, J, 2012)	0.38
"5, 1, 2, 3, and 4 h after drug administration were determined by liquid chromatography-tandem mass spectrometry (LC-MS/MS) method, and full set of pharmacokinetic data was analyzed with nonlinear mixed-effect modeling (NONMEM) software."	( Population pharmacokinetics of naringin in total flavonoids of Drynaria fortunei (Kunze) J. Sm. in Chinese women with primary osteoporosis. Duan, JL; Jiang, JJ; Li, JP; Wang, JN; Wei, X; Xie, YM; Xiong, X, 2012)	0.66
"The pharmacokinetic behaviors of naringin are altered with hyperlipidemia in Chinese women with primary osteoporosis."	( Population pharmacokinetics of naringin in total flavonoids of Drynaria fortunei (Kunze) J. Sm. in Chinese women with primary osteoporosis. Duan, JL; Jiang, JJ; Li, JP; Wang, JN; Wei, X; Xie, YM; Xiong, X, 2012)	0.95
" Here we determine the pharmacokinetic characteristics of the four most abundant compounds in DCQD using a rat model of severe acute pancreatitis."	( Pharmacokinetic and pharmacodynamic studies of four major phytochemical components of Da-Cheng-Qi decoction to treat acute pancreatitis. Chen, G; Gong, H; Tang, W; Wang, J; Xiang, J; Zhao, J, 2013)	0.39
"The pharmacokinetic differences of paeoniflorin, naringin, naringenin and glycyrrhetinic acid (GA) following oral administration of pure compounds, single herbs and Si-Ni-San (SNS) decoction to rats were studied."	( Comparative pharmacokinetic study of four major components after oral administration of pure compounds, herbs and Si-Ni-San to rats. Li, F; Wang, Y; Wen, J; Yang, L; Zhao, L; Zheng, W, 2014)	0.66
" The sensitive and selective method was applied to a pharmacokinetic study of icarrin, naringin and osthole in rats after oral administration of Gushudan capsule."	( Simultaneous determination of icariin, naringin and osthole in rat plasma by UPLC-MS/MS and its application for pharmacokinetic study after oral administration of Gushudan capsules. Deng, Y; Guo, X; Li, F; Li, N; Lu, Y; Xiong, Z; Zhao, L, 2015)	0.91
" The developed method was successfully applied to a pharmacokinetic study of ginsenoside Rb1, naringin, ginsenoside Rb2 and oridonin in rats after oral administration of a Weifuchun tablet."	( Simultaneous determination of ginsenoside Rb1, naringin, ginsenoside Rb2 and oridonin in rat plasma by LC-MS/MS and its application to a pharmacokinetic study after oral administration of Weifuchun tablet. Du, Y; Jin, Y; Ma, Y; Tian, T; Xu, H, 2015)	0.89
" The proposed method was successfully applied to the pharmacokinetic drug interaction study of rosuvastatin combined with naringin in rats."	( Simultaneous determination of rosuvastatin, naringin and naringenin in rat plasma by RRLC-MS/MS and its application to a pharmacokinetic drug interaction study. Bai, Y; Chen, T; Liu, H; Su, W; Yan, Z; Yao, H; Zeng, X; Zhang, W; Zheng, Y, 2018)	0.95
" However, the pharmacokinetic aspects of naringin and its therapeutic potentials in respiratory diseases have not been comprehensively reviewed."	( A Review on the Pharmacokinetic Properties of Naringin and Its Therapeutic Efficacies in Respiratory Diseases. Chai, L; Liu, B; Shi, R; Su, W; Yao, H; Zeng, X, 2020)	1.08

Excerpt	Reference	Relevance
"Grapefruit juice (GFJ) has been found to interact with several medications, increasing their oral bioavailability and the risk of toxicity."	( Variation of flavonoids and furanocoumarins in grapefruit juices: a potential source of variability in grapefruit juice-drug interaction studies. Butterweck, V; De Castro, WV; Derendorf, H; Mertens-Talcott, S; Rubner, A, 2006)	0.33
"The effects of the anticancer drug irinotecan combined with ethanolic extract of propolis (EEP), a water-soluble derivate of propolis (WSDP), quercetin and naringin on the growth of Ehrlich ascites tumor (EAT) and the life span of tumor-bearing Swiss albino mice were studied."	( Enhanced antitumor activity of irinotecan combined with propolis and its polyphenolic compounds on Ehrlich ascites tumor in mice. Basic, I; Benkovic, V; Bevanda, M; Brozovic, G; Dikic, D; Horvat Knezevic, A; Knezevic, F; Orsolic, N, 2007)	0.54
"The hepatic organic anion transporting polypeptides (OATPs) influence the pharmacokinetics of several drug classes and are involved in many clinical drug-drug interactions."	( Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. Artursson, P; Haglund, U; Karlgren, M; Kimoto, E; Lai, Y; Norinder, U; Vildhede, A; Wisniewski, JR, 2012)	0.38
"A flow-injection mass spectrometric metabolic fingerprinting method in combination with chemometrics was used to differentiate Aurantii Fructus Immaturus from its counterfeit Poniciri Trifoliatae Fructus Immaturus."	( Differentiation of Aurantii Fructus Immaturus from Poniciri Trifoliatae Fructus Immaturus using flow-injection mass spectrometric (FIMS) metabolic fingerprinting method combined with chemometrics. Chang, YS; Chen, P; Zhao, Y, 2015)	0.42
"Three different NAR concentrations (10, 100, and 1 000 μmol·L⁻¹) were applied, alone or combined with BMP-2(50 ng·mL⁻¹), to restore the osteoblastogenesis of pre-osteoblasts (MC3T3-E1 cell line)."	( [Effect of naringin combined with bone morphogenetic protein-2 on the proliferation and differentiation of MC3T3-E1 cells]. Gaoli, X; Guang, H; Lili, W; Qiutao, S; Yi, L; Zhiyuan, G, 2017)	0.84
"Stimulation by NAR alone and in combination with BMP-2 for 1 day and 4 days could promote cell proliferation, which peaked at a concentration of 100 μmol·L⁻¹ NAR combined with BMP-2 could promote cell proliferation significantly (P<0."	( [Effect of naringin combined with bone morphogenetic protein-2 on the proliferation and differentiation of MC3T3-E1 cells]. Gaoli, X; Guang, H; Lili, W; Qiutao, S; Yi, L; Zhiyuan, G, 2017)	0.84
" The proposed method was successfully applied to the pharmacokinetic drug interaction study of rosuvastatin combined with naringin in rats."	( Simultaneous determination of rosuvastatin, naringin and naringenin in rat plasma by RRLC-MS/MS and its application to a pharmacokinetic drug interaction study. Bai, Y; Chen, T; Liu, H; Su, W; Yan, Z; Yao, H; Zeng, X; Zhang, W; Zheng, Y, 2018)	0.95
"The present study aimed to develop a strategy involving quantitative analysis of multicomponents by single marker in combination with high-performance liquid chromatography fingerprint qualitative analysis for performing the quality control of Aurantii Fructus."	( Quantitative analysis of multicomponents by single marker combined with HPLC fingerprint qualitative analyses for comprehensive evaluation of Aurantii Fructus. Cai, X; Huang, D; Lei, Y; Lin, M; Luo, K; Sun, Z; Tan, S; Wang, Y; Xia, X; Yan, J; Zhang, Y, 2020)	0.56
" This study investigated the death of both colon cancer HT29 cells and healthy vascular smooth muscle TG-Ha-VSMC cells (VSMCs) induced by naringin combined with endoplasmic reticulum (ER) stress and NF-κB inhibition."	( Naringin Combined with NF-κB Inhibition and Endoplasmic Reticulum Stress Induces Apoptotic Cell Death via Oxidative Stress and the PERK/eIF2α/ATF4/CHOP Axis in HT29 Colon Cancer Cells. Albayrak, D; Bostancı, A; Doğan, A; Doğanlar, O; Doğanlar, ZB; Erdoğan, S; Meraklı, M; Turker, P, 2021)	2.27

Excerpt	Reference	Relevance
" Naringenin formation is thought to be the crucial step in determination of bioavailability of the compound, which undergoes rapid glucuronidation."	( The fate of naringin in humans: a key to grapefruit juice-drug interactions? Fuhr, U; Kummert, AL, 1995)	0.67
"The bioavailability of some dihydropyridine calcium antagonists can be markedly augmented by grapefruit juice and may involve the bioflavonoid naringin."	( Effect of grapefruit juice and naringin on nisoldipine pharmacokinetics. Arnold, JM; Bailey, DG; Munoz, C; Spence, JD; Strong, HA, 1993)	0.77
" The interaction could not be predicted from baseline pharmacokinetics with water and did not result in more consistent bioavailability among individuals."	( Grapefruit juice--felodipine interaction: mechanism, predictability, and effect of naringin. Arnold, JM; Bailey, DG; Munoz, C; Spence, JD, 1993)	0.51
" Cumulative urinary recovery indicated low bioavailability ( < 25%) of naringin and hesperidin."	( Flavanone absorption after naringin, hesperidin, and citrus administration. Ameer, B; Johnson, JV; Rouseff, RL; Weintraub, RA; Yost, RA, 1996)	0.82
"The bioavailability of dihydropyridine calcium channel blockers following oral administration was shown to be increased by concomitant intake of grapefruit juice for all drugs of this class tested up to now."	( Grapefruit juice increases oral nimodipine bioavailability. Blume, H; Fuhr, U; Huschka, C; Kuhlmann, J; Maier-Brüggemann, A; Mück, W; Rietbrock, S; Staib, AH; Unger, S; Zaigler, M, 1998)	0.3
" The variable effect with the particulate fraction may result from erratic bioavailability of unidentified primary active substances."	( Grapefruit juice-felodipine interaction: effect of naringin and 6',7'-dihydroxybergamottin in humans. Bailey, DG; Bend, JR; Freeman, DJ; Kreeft, JH; Munoz, C, 1998)	0.55
" On the other hand, an increase in the bioavailability of some medicaments have been observed when these are ingested together with grapefruit."	( Inhibitory effect of naringin on the micronuclei induced by ifosfamide in mouse, and evaluation of its modulatory effect on the Cyp3a subfamily. Alvarez-González, I; Dorado, V; Espinosa-Aguirre, JJ; Madrigal-Bujaidar, E, 2001)	0.63
" The results showed that the absolute bioavailability of oral naringenin was only 4%, whereas after taking the conjugated naringenin into account, it increased to 8%."	( Comparison of metabolic pharmacokinetics of naringin and naringenin in rabbits. Chao, PD; Chin, DH; Hou, YC; Hsiu, SL; Huang, TY, 2002)	0.58
"The aim of this study was to investigate the effect of naringin on the bioavailability and pharmacokinetics of paclitaxel after oral administration of paclitaxel or its prodrug coadministered with naringin to rats."	( Enhanced paclitaxel bioavailability after oral coadministration of paclitaxel prodrug with naringin to rats. Choi, JS; Shin, SC, 2005)	0.8
" Consequently, absolute and relative bioavailability values of diltiazem in the presence of naringin were significantly higher (p<0."	( Enhanced oral exposure of diltiazem by the concomitant use of naringin in rats. Choi, JS; Han, HK, 2005)	0.79
"Grapefruit juice (GFJ) has been found to interact with several medications, increasing their oral bioavailability and the risk of toxicity."	( Variation of flavonoids and furanocoumarins in grapefruit juices: a potential source of variability in grapefruit juice-drug interaction studies. Butterweck, V; De Castro, WV; Derendorf, H; Mertens-Talcott, S; Rubner, A, 2006)	0.33
" In conclusion, pretreatment of naringin enhanced the oral bioavailability of verapamil."	( Effect of naringin pretreatment on bioavailability of verapamil in rabbits. Choi, JS; Yeum, CH, 2006)	1.02
"We showed previously that grapefruit and orange juices inhibited human enteric organic anion-transporting polypeptide (OATP)1A2 in vitro and lowered oral fexofenadine bioavailability clinically."	( Naringin is a major and selective clinical inhibitor of organic anion-transporting polypeptide 1A2 (OATP1A2) in grapefruit juice. Bailey, DG; Dresser, GK; Kim, RB; Leake, BF, 2007)	1.78
" In conclusion, various beverages, especially teas, inhibit the function of SULT1A3, and therefore may have the potential to increase the bioavailability of orally administered substrates of SULT1A3, such as beta(2) agonists."	( Inhibitory effects of various beverages on human recombinant sulfotransferase isoforms SULT1A1 and SULT1A3. Hiratsuka, A; Nishimuta, H; Ogura, K; Ohtani, H; Sawada, Y; Tsujimoto, M, 2007)	0.34
"The aim of this study was to investigate the effect of naringin on the bioavailability and pharmacokinetics of tamoxifen and of its metabolite, 4-hydroxytamoxifen in rats."	( Enhanced tamoxifen bioavailability after oral administration of tamoxifen in rats pretreated with naringin. Choi, JS; Kang, KW, 2008)	0.81
" This system was used for fermentation of tomato pulp, with the aim of improving the bioavailability of flavonoids in processed tomato products."	( Characterization of Rhamnosidases from Lactobacillus plantarum and Lactobacillus acidophilus. Beekwilder, J; de Vos, R; Francke, C; Hall, RD; Janssen, P; Marcozzi, D; van Hylckama Vlieg, J; Vecchi, S, 2009)	0.35
"05) or kept unaltered the absorption rate constant (k(a) ) of SQV in function of the concentration of both compounds administered."	( In situ study of the effect of naringin, talinolol and protein-energy undernutrition on intestinal absorption of saquinavir in rats. Catalán-Latorre, A; Jiménez-Torres, NV; Merino, V; Merino-Sanjuán, M; Nácher, A, 2011)	0.66
"1 %) from citrus extract or with highly bioavailable curcumin from Curcuma longa extract (0."	( Effect of citrus polyphenol- and curcumin-supplemented diet on inflammatory state in obese cats. Freuchet, B; Jeusette, I; Le Bloc'h, J; Leray, V; Nguyen, P; Torre, C, 2011)	0.37
" In this manner, the flavonoids could contribute beneficial effects on the mechanisms of hypertension and thrombosis by increasing the bioavailability of NO."	( Preventive effects of hesperidin, glucosyl hesperidin and naringin on hypertension and cerebral thrombosis in stroke-prone spontaneously hypertensive rats. Giddings, JC; Ikemura, M; Sasaki, Y; Yamamoto, J, 2012)	0.62
" The mean of population parameters clearance (C1), central distribution volume (V), absorption rate constant (Ka1), inter-compartmental clearance (C2), peripheral distribution volume (V2) were set as parameters and estimated through base model, covariate model, and final model."	( Population pharmacokinetics of naringin in total flavonoids of Drynaria fortunei (Kunze) J. Sm. in Chinese women with primary osteoporosis. Duan, JL; Jiang, JJ; Li, JP; Wang, JN; Wei, X; Xie, YM; Xiong, X, 2012)	0.66
" The data also suggest that concomitant treatment with NAR can restore NO bioavailability through either its metal-chelating properties or its antioxidant activity."	( Erythrocyte nitric oxide synthase as a surrogate marker for mercury-induced vascular damage: the modulatory effects of naringin. Abo-Salem, OM; Attiaa, SM; Harisa, GI; Mariee, AD, 2014)	0.61
" Surprisingly, pharmacokinetic analysis revealed that naringin has low bioavailability (11%), implying that the prokinetic effect of naringin was largely due to the local activation of ghrelin receptor in the intestine rather than a systemic effect after absorption."	( Naringin exhibits in vivo prokinetic activity via activation of ghrelin receptor in gastrointestinal motility dysfunction rats. Jang, Y; Kim, TK; Shim, WS, 2013)	2.08
"7-folds increase in apparent bioavailability was noticed with freeze-dried solid dispersions with naringin as compared to free CAN suspension administered alone."	( Oral bioavailability and intestinal absorption of candesartan cilexetil: role of naringin as P-glycoprotein inhibitor. Gurunath, S; Nanjwade, BK; Patil, PA, 2015)	0.86
" Our results suggest that polyphenolic compounds might be potential structural bases and source to find and project nature-based, safe, orally bioavailable direct thrombin inhibitors."	( Thrombin inhibitory activity of some polyphenolic compounds. Bijak, M; Krotkiewski, H; Nowak, P; Pawlaczyk, I; Ponczek, M; Saluk, J; Wachowicz, B; Ziewiecki, R, 2014)	0.4
" These data suggest that NAR can restore NO bioavailability in a situation of Pb-induced cellular damage."	( Mitigation of lead-induced neurotoxicity by the naringin: erythrocytes as neurons substitute markers. Harisa, GI, 2014)	0.66
"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
"This study demonstrated that increased solubilization (favored by freeze-dried solid dispersion) and efflux pump inhibition (using naringin), the relative bioavailability of CDS can be increased, suggesting an alternative potential for improving oral bioavailability of CAN."	( Corroboration of naringin effects on the intestinal absorption and pharmacokinetic behavior of candesartan cilexetil solid dispersions using in-situ rat models. K Nanjwade, B; Patil, PA; Surampalli, G, 2015)	0.96
" A controlled, open, randomized, crossover study was performed in 10 healthy volunteers to investigate the effect of high-dose naringin on the bioavailability of talinolol, a substrate of intestinal organic anion-transporting polypeptide (OATP)-mediated uptake."	( High-dose short-term administration of naringin did not alter talinolol pharmacokinetics in humans. Langguth, P; Nguyen, MA; Staubach, P; Tamai, I, 2015)	0.89
" In conclusion, ternary nanoparticles are considered promising carriers to effectively improve the bioavailability of naringin."	( Structural characterization and bioavailability of ternary nanoparticles consisting of amylose, α-linoleic acid and β-lactoglobulin complexed with naringin. Feng, T; Liu, F; Wang, K; Xu, Z; Ye, R; Zhu, X; Zhuang, H, 2017)	0.86
" Yet, its low water solubility, limited permeability, and suboptimal bioavailability limited its use."	( Polymeric micelles for potentiated antiulcer and anticancer activities of naringin. Abu Hashim, II; Badria, FAE; El-Sheakh, AR; Hamed, MF; Mohamed, EA; Shaaban, AAA; Yusif, RM, 2018)	0.71
" The topic is discussed in light of recently developed biomaterial-based approaches that potentiate its bioavailability and bioactivity."	( Bioinspired bone therapies using naringin: applications and advances. Gaspar, VM; Lavrador, P; Mano, JF, 2018)	0.76
" The aim of this study was to develop solid dispersion (SD) and to improve the dissolution rate and oral bioavailability of NA."	( Preparation, characterization and in vitro and in vivo evaluation of a solid dispersion of Naringin. Chen, H; Duan, X; Jiang, Z; Lin, S; Liu, H; Qiang, Y; Wang, J; Xu, Y; Ye, X; Zhang, K, 2018)	0.7
" Reported pharmacokinetic studies revealed that oral bioavailability of naringin was low, in contrast to its significant pharmacological effects."	( Tissue distribution of naringin and derived metabolites in rats after a single oral administration. He, Y; Li, P; Rao, H; Su, W; Yao, H; Zeng, X; Zheng, Y, 2020)	1.1
" However, its oral bioavailability is low (8%) possibly due to cleavage at the upper gut."	( Colon Targeting of Naringin for Enhanced Cytoprotection Against Indomethacin-Induced Colitis in Rabbits. Borg, TM; El Naggar, EE; El-Sheakh, AR; Hamed, MF; Mohamed, EA, 2020)	0.89
"The number of studies related to the bioavailability and pharmacokinetics of NAR is limited."	( New Perspectives in the Pharmacological Potential of Naringin in Medicine. Rivoira, MA; Rodriguez, V; Talamoni, G; Tolosa de Talamoni, N, 2021)	0.87
" Since a scarce number of clinical studies have been performed, the NAR use requires more investigation in order to know better their safety, efficacy, delivery, and bioavailability in humans."	( New Perspectives in the Pharmacological Potential of Naringin in Medicine. Rivoira, MA; Rodriguez, V; Talamoni, G; Tolosa de Talamoni, N, 2021)	0.87
" To cope with the low bioavailability of naringin, a new bienzyme whole-cell system was developed for bioconversion of naringin into two lipophilic derivatives."	( One-pot biocatalytic synthesis and antioxidant activities of highly lipophilic naringin derivatives by using bi-functional whole-cells. Lai, X; Li, X; Nong, J; Xiao, X; Zhao, G; Zhao, Y, 2020)	1.05
"This study examined the effects of phase II metabolism and efflux transportation on the bioavailability of naringin, hesperidin, and their aglycones (naringenin and hesperetin) in rats."	( Involvement of phase II enzymes and efflux transporters in the metabolism and absorption of naringin, hesperidin and their aglycones in rats. Cao, X; Fang, X; Guo, A; Guo, X; Li, E, 2022)	1.15
"Naringin, one of the citrus flavonoids and known as a natural antioxidant, has limited bioavailability owing to its low stability and solubility."	( Efficient Production of Naringin Acetate with Different Acyl Donors via Enzymatic Transesterification by Lipases. Baek, Y; Kim, HU; Lee, S; Lee, SH; Lee, T; Oh, JM; Park, C; Park, SJ; Seo, SW; Son, J; Yoo, HY, 2022)	2.47
" However, the bitterness, low water-solubility, and low bioavailability of naringin are the main issues limiting its use in the pharmaceutical and nutraceutical industries."	( Enhancement of debitterness, water-solubility, and neuroprotective effects of naringin by transglucosylation. Cho, JY; Eom, S; Im, AE; Kim, D; Kim, H; Lee, JH; Nam, SH; Seong, HJ; Yang, KY, 2023)	1.37

Excerpt	Relevance	Reference
" Urine samples were collected up to 24 h after dosing and 7-hydroxycoumarin was quantified fluorimetrically in urine hydrolysates after HPLC separation to determine the excretion rates."	( The character of inhibition of the metabolism of 1,2-benzopyrone (coumarin) by grapefruit juice in human. Bourian, M; Legrum, W; Runkel, M; Tegtmeier, M, 1997)	0.3
" Oral dosing of naringin resulted in even higher ratio of AUC of naringenin conjugates to the total naringenin than that after oral naringenin."	( Comparison of metabolic pharmacokinetics of naringin and naringenin in rabbits. Chao, PD; Chin, DH; Hou, YC; Hsiu, SL; Huang, TY, 2002)	0.92
" Oral paclitaxel preparations which is more convenient than the IV dosage forms could be developed with a prodrug form with naringin."	( Enhanced paclitaxel bioavailability after oral coadministration of paclitaxel prodrug with naringin to rats. Choi, JS; Shin, SC, 2005)	0.76
" Based on these results, the verapamil dosage should be adjusted when given with naringin or a naringin-containing dietary supplement."	( Effect of naringin pretreatment on bioavailability of verapamil in rabbits. Choi, JS; Yeum, CH, 2006)	0.96
" The purpose of the current study was to identify changes in caffeine pharmacokinetics, resting energy expenditure (REE), oxygen consumption (VO(2)) and respiratory exchange ratio (RER) after an acute dosage of caffeine and naringin."	( Naringin does not alter caffeine pharmacokinetics, energy expenditure, or cardiovascular haemodynamics in humans following caffeine consumption. Agrawal, P; Ballard, TL; Halaweish, FT; Stevermer, CL; Vukovich, MD, 2006)	1.96
" With the bioconversion rate as the index, the effects of pH value, temperature, reaction time, dosage of enzyme and concentration of naringin-HP-beta-CD on conversion rate of naringenin were detected for the purpose of optimizing the preparation condition."	( [Preparation of naringenin by enzymolysis of naringin-HP-beta-CD]. Cui, L; Jia, X; Jiang, Y; Qian, Q; Sun, E; Zhang, Z, 2012)	0.84
" The blood samples were collected before dosing and subsequently at 10, 15, 20, 30, 45 min, 1, 2, 4, 8, and 12 h following gavage."	( Effect of formula compatibility on the pharmacokinetics of components from Dachengqi Decoction [See Text] in rats. Chen, GY; Gong, HL; Huang, X; Tang, WF; Wang, J, 2012)	0.38
" The medium dose (300 mg/kg) appeared to be the optimal dosage for delivering satisfactory therapeutic effects."	( Naringin promotes osteoblast differentiation and effectively reverses ovariectomy-associated osteoporosis. Jiang, Y; Li, N; Wooley, PH; Xu, Z; Yang, SY, 2013)	1.83
" The long-term tibia pin-implantation mouse model study suggested that daily oral gavage of naringin at 300 mg/kg dosage for 30 days significantly alleviated the periprosthetic bone resorption."	( Therapeutic potentials of naringin on polymethylmethacrylate induced osteoclastogenesis and osteolysis, in vitro and in vivo assessments. Li, N; Wooley, PH; Xu, Z; Yang, SY; Zhang, J, 2014)	0.92
" Moreover, it is contained in highly dosed nutraceuticals available on the market."	( High-dose short-term administration of naringin did not alter talinolol pharmacokinetics in humans. Langguth, P; Nguyen, MA; Staubach, P; Tamai, I, 2015)	0.69
" Naringin with concentration of 150 mg/kg appeared to be an optimal dosage to deliver the therapeutic effects."	( [Naringin reduced polymethylmethacrylate-induced osteolysis in the mouse air sacs model]. Li, NH; Xu, ZW, 2015)	2.24
" Furthermore, oral bioavailabilities of NA-PEG6000 (1:3) SD and NA-suspension with the same dosage were investigated in SD rats."	( Preparation, characterization and in vitro and in vivo evaluation of a solid dispersion of Naringin. Chen, H; Duan, X; Jiang, Z; Lin, S; Liu, H; Qiang, Y; Wang, J; Xu, Y; Ye, X; Zhang, K, 2018)	0.7
" That is, naringin or vitamin C in the fruit or food may increase the blood concentration of lovastatin; perhaps taking frequency or dosage of lovastatin may be reduced."	( Study on the interaction between lovastatin and three digestive enzymes and the effect of naringin and vitamin C on it by spectroscopy and docking methods. Liu, Y; Liu, Z; Meng, X; Nan, G; Song, N; Wang, Y; Yang, G; Yang, L; Zhang, L, 2020)	1.18
" The findings indicate that these agents commonly induced protective effects that are typically mediated via hormetic mechanisms leading to biphasic dose-response relationships."	( Naringin commonly acts via hormesis. Agathokleous, E; Calabrese, EJ; Calabrese, V; Dhawan, G; Hayes, AW; Kapoor, R; Manes, P; Pressman, P, 2023)	2.35

Product Category	Products
Professional Supplements	2
Vitamins & Supplements	1

Product	Brand	Category	Compounds Matched from Ingredients	Date Retrieved
Double Wood Supplements Citrus Bergamot Extract -- 1000 mg - 60 Capsules	Double Wood Supplements	Professional Supplements	Naringin, Neohesperidin	2024-11-29 10:47:42
InterPlexus Flavo Plex C™ -- 60 Capsules	InterPlexus	Professional Supplements	Vitamin C, Hesperidin Methyl Chalcone, Hesperidin, Naringin	2024-11-29 10:47:42
Twinlab OcuGuard® Plus -- 60 Veggie Caps	Twinlab	Vitamins & Supplements	N-Acetyl L-Cysteine, Vitamin C, Chromium, Vitamin E, eriocitrin, Vitamin E, Lutein, naringin, Quercetin Dihydrate, Vitamin A, Riboflavin, Rutin, Selenium, Taurine, Zeaxanthin	2024-11-29 10:47:42

Role	Description
metabolite	Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antineoplastic agent	A substance that inhibits or prevents the proliferation of neoplasms.
anti-inflammatory agent	Any compound that has anti-inflammatory effects.
[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
neohesperidoside	A glycoside containing alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl residue as the sugar unit.
disaccharide derivative	A carbohydrate derivative that is formally obtained from a disaccharide.
dihydroxyflavanone	Any hydroxyflavanone carrying two hydroxy substituents.
4'-hydroxyflavanones	Any hydroxyflavanone having a hydroxy substituent located at position 4'.
(2S)-flavan-4-one	Any flavanone in which the chiral centre at position 2 has S-configuration.
[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
naringenin glycoside biosynthesis	0	8

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
thioredoxin reductase	Rattus norvegicus (Norway rat)	Potency	79.4328	0.1000	20.8793	79.4328	AID588453
euchromatic histone-lysine N-methyltransferase 2	Homo sapiens (human)	Potency	44.6684	0.0355	20.9770	89.1251	AID504332
chromobox protein homolog 1	Homo sapiens (human)	Potency	56.2341	0.0060	26.1688	89.1251	AID540317
nuclear receptor ROR-gamma isoform 1	Mus musculus (house mouse)	Potency	0.7079	0.0079	8.2332	1,122.0200	AID2551
TAR DNA-binding protein 43	Homo sapiens (human)	Potency	0.7943	1.7783	16.2081	35.4813	AID652104
[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)
ubiquitin-conjugating enzyme E2 N	Homo sapiens (human)	IC50 (µMol)	7.6785	0.8730	10.7219	78.4000	AID493155; AID493182
bcl-2-related protein A1	Mus musculus (house mouse)	IC50 (µMol)	20.0000	0.4190	7.7563	35.1000	AID504689
Aromatase	Homo sapiens (human)	IC50 (µMol)	5.0000	0.0000	1.2904	10.0000	AID405559
Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)	IC50 (µMol)	75.9000	0.0005	3.4984	9.7600	AID1475098; AID379219
[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)
Heparanase	Homo sapiens (human)	Kd	1,000.0000	0.2400	0.2400	0.2400	AID738328
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
negative regulation of chronic inflammatory response	Aromatase	Homo sapiens (human)
steroid biosynthetic process	Aromatase	Homo sapiens (human)
estrogen biosynthetic process	Aromatase	Homo sapiens (human)
androgen catabolic process	Aromatase	Homo sapiens (human)
syncytium formation	Aromatase	Homo sapiens (human)
negative regulation of macrophage chemotaxis	Aromatase	Homo sapiens (human)
sterol metabolic process	Aromatase	Homo sapiens (human)
female genitalia development	Aromatase	Homo sapiens (human)
mammary gland development	Aromatase	Homo sapiens (human)
uterus development	Aromatase	Homo sapiens (human)
prostate gland growth	Aromatase	Homo sapiens (human)
testosterone biosynthetic process	Aromatase	Homo sapiens (human)
positive regulation of estradiol secretion	Aromatase	Homo sapiens (human)
female gonad development	Aromatase	Homo sapiens (human)
response to estradiol	Aromatase	Homo sapiens (human)
positive regulation of JUN kinase activity	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
protein dephosphorylation	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
insulin receptor signaling pathway	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
regulation of signal transduction	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of signal transduction	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
actin cytoskeleton organization	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
regulation of endocytosis	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of vascular endothelial growth factor receptor signaling pathway	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
endoplasmic reticulum unfolded protein response	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
regulation of intracellular protein transport	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
cellular response to unfolded protein	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
peptidyl-tyrosine dephosphorylation	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
platelet-derived growth factor receptor-beta signaling pathway	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
IRE1-mediated unfolded protein response	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
insulin receptor recycling	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of MAP kinase activity	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of insulin receptor signaling pathway	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
regulation of type I interferon-mediated signaling pathway	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
growth hormone receptor signaling pathway via JAK-STAT	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
positive regulation of protein tyrosine kinase activity	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascade	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
regulation of hepatocyte growth factor receptor signaling pathway	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathway	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
positive regulation of IRE1-mediated unfolded protein response	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of PERK-mediated unfolded protein response	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
peptidyl-tyrosine dephosphorylation involved in inactivation of protein kinase activity	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
positive regulation of receptor catabolic process	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
potassium ion transport	G protein-activated inward rectifier potassium channel 2	Homo sapiens (human)
regulation of monoatomic ion transmembrane transport	G protein-activated inward rectifier potassium channel 2	Homo sapiens (human)
potassium ion import across plasma membrane	G protein-activated inward rectifier potassium channel 2	Homo sapiens (human)
potassium ion transport	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
potassium ion transmembrane transport	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
regulation of heart rate by cardiac conduction	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
membrane repolarization during atrial cardiac muscle cell action potential	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
membrane repolarization during ventricular cardiac muscle cell action potential	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
ventricular cardiac muscle cell membrane repolarization	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
potassium ion import across plasma membrane	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
regulation of monoatomic ion transmembrane transport	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
potassium ion transport	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
response to electrical stimulus	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
potassium ion transmembrane transport	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
regulation of heart rate by cardiac conduction	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
membrane repolarization during atrial cardiac muscle cell action potential	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
membrane repolarization during ventricular cardiac muscle cell action potential	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
regulation of presynaptic membrane potential	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
ventricular cardiac muscle cell membrane repolarization	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
potassium ion import across plasma membrane	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
regulation of monoatomic ion transmembrane transport	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
negative regulation of protein phosphorylation	TAR DNA-binding protein 43	Homo sapiens (human)
mRNA processing	TAR DNA-binding protein 43	Homo sapiens (human)
RNA splicing	TAR DNA-binding protein 43	Homo sapiens (human)
negative regulation of gene expression	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of protein stability	TAR DNA-binding protein 43	Homo sapiens (human)
positive regulation of insulin secretion	TAR DNA-binding protein 43	Homo sapiens (human)
response to endoplasmic reticulum stress	TAR DNA-binding protein 43	Homo sapiens (human)
positive regulation of protein import into nucleus	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of circadian rhythm	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of apoptotic process	TAR DNA-binding protein 43	Homo sapiens (human)
negative regulation by host of viral transcription	TAR DNA-binding protein 43	Homo sapiens (human)
rhythmic process	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of cell cycle	TAR DNA-binding protein 43	Homo sapiens (human)
3'-UTR-mediated mRNA destabilization	TAR DNA-binding protein 43	Homo sapiens (human)
3'-UTR-mediated mRNA stabilization	TAR DNA-binding protein 43	Homo sapiens (human)
nuclear inner membrane organization	TAR DNA-binding protein 43	Homo sapiens (human)
amyloid fibril formation	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of gene expression	TAR DNA-binding protein 43	Homo sapiens (human)
proteoglycan metabolic process	Heparanase	Homo sapiens (human)
cell-matrix adhesion	Heparanase	Homo sapiens (human)
response to organic substance	Heparanase	Homo sapiens (human)
positive regulation of vascular endothelial growth factor production	Heparanase	Homo sapiens (human)
positive regulation of blood coagulation	Heparanase	Homo sapiens (human)
heparan sulfate proteoglycan catabolic process	Heparanase	Homo sapiens (human)
heparin metabolic process	Heparanase	Homo sapiens (human)
positive regulation of osteoblast proliferation	Heparanase	Homo sapiens (human)
regulation of hair follicle development	Heparanase	Homo sapiens (human)
positive regulation of hair follicle development	Heparanase	Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transduction	Heparanase	Homo sapiens (human)
establishment of endothelial barrier	Heparanase	Homo sapiens (human)
vascular wound healing	Heparanase	Homo sapiens (human)
protein transmembrane transport	Heparanase	Homo sapiens (human)
angiogenesis involved in wound healing	Heparanase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
iron ion binding	Aromatase	Homo sapiens (human)
steroid hydroxylase activity	Aromatase	Homo sapiens (human)
electron transfer activity	Aromatase	Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen	Aromatase	Homo sapiens (human)
oxygen binding	Aromatase	Homo sapiens (human)
heme binding	Aromatase	Homo sapiens (human)
aromatase activity	Aromatase	Homo sapiens (human)
RNA binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
protein tyrosine phosphatase activity	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
insulin receptor binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
protein binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
zinc ion binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
enzyme binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
protein kinase binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
receptor tyrosine kinase binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
cadherin binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
ephrin receptor binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
protein phosphatase 2A binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activity	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
protein binding	G protein-activated inward rectifier potassium channel 2	Homo sapiens (human)
G-protein activated inward rectifier potassium channel activity	G protein-activated inward rectifier potassium channel 2	Homo sapiens (human)
inward rectifier potassium channel activity	G protein-activated inward rectifier potassium channel 2	Homo sapiens (human)
inward rectifier potassium channel activity	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
protein binding	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
G-protein activated inward rectifier potassium channel activity	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
voltage-gated potassium channel activity involved in atrial cardiac muscle cell action potential repolarization	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
inward rectifier potassium channel activity	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
protein binding	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
G-protein activated inward rectifier potassium channel activity	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
voltage-gated potassium channel activity involved in atrial cardiac muscle cell action potential repolarization	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
voltage-gated monoatomic ion channel activity involved in regulation of presynaptic membrane potential	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	TAR DNA-binding protein 43	Homo sapiens (human)
DNA binding	TAR DNA-binding protein 43	Homo sapiens (human)
double-stranded DNA binding	TAR DNA-binding protein 43	Homo sapiens (human)
RNA binding	TAR DNA-binding protein 43	Homo sapiens (human)
mRNA 3'-UTR binding	TAR DNA-binding protein 43	Homo sapiens (human)
protein binding	TAR DNA-binding protein 43	Homo sapiens (human)
lipid binding	TAR DNA-binding protein 43	Homo sapiens (human)
identical protein binding	TAR DNA-binding protein 43	Homo sapiens (human)
pre-mRNA intronic binding	TAR DNA-binding protein 43	Homo sapiens (human)
molecular condensate scaffold activity	TAR DNA-binding protein 43	Homo sapiens (human)
beta-glucuronidase activity	Heparanase	Homo sapiens (human)
protein binding	Heparanase	Homo sapiens (human)
heparanase activity	Heparanase	Homo sapiens (human)
syndecan binding	Heparanase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
endoplasmic reticulum	Aromatase	Homo sapiens (human)
endoplasmic reticulum membrane	Aromatase	Homo sapiens (human)
membrane	Aromatase	Homo sapiens (human)
endoplasmic reticulum	Aromatase	Homo sapiens (human)
plasma membrane	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
cytoplasm	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
mitochondrial matrix	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
early endosome	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
endoplasmic reticulum	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
cytosol	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
mitochondrial crista	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
endosome lumen	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
sorting endosome	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
cytoplasmic side of endoplasmic reticulum membrane	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
protein-containing complex	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
endoplasmic reticulum	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
cytoplasm	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
early endosome	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
Golgi apparatus	G protein-activated inward rectifier potassium channel 2	Homo sapiens (human)
plasma membrane	G protein-activated inward rectifier potassium channel 2	Homo sapiens (human)
voltage-gated potassium channel complex	G protein-activated inward rectifier potassium channel 2	Homo sapiens (human)
plasma membrane	G protein-activated inward rectifier potassium channel 2	Homo sapiens (human)
plasma membrane	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
I(KACh) inward rectifier potassium channel complex	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
voltage-gated potassium channel complex	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
plasma membrane	G protein-activated inward rectifier potassium channel 4	Homo sapiens (human)
plasma membrane	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
external side of plasma membrane	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
T-tubule	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
presynaptic membrane	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
parallel fiber to Purkinje cell synapse	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
I(KACh) inward rectifier potassium channel complex	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
voltage-gated potassium channel complex	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
plasma membrane	G protein-activated inward rectifier potassium channel 1	Homo sapiens (human)
intracellular non-membrane-bounded organelle	TAR DNA-binding protein 43	Homo sapiens (human)
nucleus	TAR DNA-binding protein 43	Homo sapiens (human)
nucleoplasm	TAR DNA-binding protein 43	Homo sapiens (human)
perichromatin fibrils	TAR DNA-binding protein 43	Homo sapiens (human)
mitochondrion	TAR DNA-binding protein 43	Homo sapiens (human)
cytoplasmic stress granule	TAR DNA-binding protein 43	Homo sapiens (human)
nuclear speck	TAR DNA-binding protein 43	Homo sapiens (human)
interchromatin granule	TAR DNA-binding protein 43	Homo sapiens (human)
nucleoplasm	TAR DNA-binding protein 43	Homo sapiens (human)
chromatin	TAR DNA-binding protein 43	Homo sapiens (human)
extracellular region	Heparanase	Homo sapiens (human)
nucleus	Heparanase	Homo sapiens (human)
nucleoplasm	Heparanase	Homo sapiens (human)
lysosome	Heparanase	Homo sapiens (human)
lysosomal membrane	Heparanase	Homo sapiens (human)
specific granule lumen	Heparanase	Homo sapiens (human)
lysosomal lumen	Heparanase	Homo sapiens (human)
intracellular membrane-bounded organelle	Heparanase	Homo sapiens (human)
membrane raft	Heparanase	Homo sapiens (human)
extracellular space	Heparanase	Homo sapiens (human)
extracellular matrix	Heparanase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID1345149	Human OATP1A2 (SLCO family of organic anion transporting polypeptides)	2007	Clinical pharmacology and therapeutics, Apr, Volume: 81, Issue:4	Naringin is a major and selective clinical inhibitor of organic anion-transporting polypeptide 1A2 (OATP1A2) in grapefruit juice.
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.
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.
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.
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.
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.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID482771	Induction of osteogenesis in rat ROS 17/2.8 cells assessed as stimulation of cell proliferation at 1 nM	2010	Journal of medicinal chemistry, Jun-10, Volume: 53, Issue:11	Emerging targets in osteoporosis disease modification.
AID1744548	Inhibition of cytochrome c (unknown origin) assessed as reduction in cyt c-CL peroxidase activity at 10 uM up to 20 mins in presence of cardiolipin by Amplex red staining based fluorescence assay relative to control	2021	Bioorganic & medicinal chemistry, 03-01, Volume: 33	A role of flavonoids in cytochrome c-cardiolipin interactions.
AID699540	Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting	2012	Journal of medicinal chemistry, May-24, Volume: 55, Issue:10	Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions.
AID1466899	Anti-atherosclerosis activity in Sprague-Dawley rat thoracic aortic vascular ring endothelial injury model assessed as decrease in CRP level at 50 uM by ELISA	2017	Bioorganic & medicinal chemistry letters, 06-15, Volume: 27, Issue:12	Anti-atherosclerotic activities of flavonoids from the flowers of Helichrysum arenarium L. MOENCH through the pathway of anti-inflammation.
AID386549	Apparent permeability from basolateral to apical side in human Caco-2 cells assessed as drug recovery	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.
AID766859	Activation of recombinant human GIRK1/2 expressed in Xenopus oocytes by two-electrode voltage clamp method	2013	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 23, Issue:18	Discovery and SAR of a novel series of GIRK1/2 and GIRK1/4 activators.
AID334635	Toxicity in Salmonella Typhimurium T98 at 300 ug/plate after 72 hrs by Ames assay in presence of Ames S-9 fraction
AID1659751	Agonist activity at TRPA1 (unknown origin) at 1000 uM relative to AITC	2020	Bioorganic & medicinal chemistry letters, 06-01, Volume: 30, Issue:11	Identification of a new class of non-electrophilic TRPA1 agonists by a structure-based virtual screening approach.
AID681614	TP_TRANSPORTER: inhibition of Saquinavir transepithelial transport (basal to apical) in Caco-2 cells	1999	British journal of clinical pharmacology, Oct, Volume: 48, Issue:4	Inhibition of the CYP3A4-mediated metabolism and P-glycoprotein-mediated transport of the HIV-1 protease inhibitor saquinavir by grapefruit juice components.
AID1248399	Inhibition of alpha-amylase (unknown origin) relative to control	2015	Bioorganic & medicinal chemistry, Oct-15, Volume: 23, Issue:20	From carbohydrates to drug-like fragments: Rational development of novel α-amylase inhibitors.
AID456316	ABTS radical scavenging activity assessed as trolox equivalent antioxidant capacity	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids.
AID768928	Inhibition of human thrombin amidolytic activity using D-Phe-Pip-Arg-pNA as substrate at 0.1 to 1000 uM preincubated for 10 mins followed by substrate addition measured every 12 secs for 10 mins by spectrophotometric analysis	2014	Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, , Volume: 23	Thrombin inhibitory activity of some polyphenolic compounds.
AID1475099	Inhibition of alpha-glucosidase (unknown origin)	2017	Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11	Structure-related protein tyrosine phosphatase 1B inhibition by naringenin derivatives.
AID671761	Inhibition of SARS coronavirus nsP13 helicase activity expressed in Escherichia coli Rosetta assessed inhibition of DNA unwinding activity at 10 uM by FRET assay	2012	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12	Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13.
AID738328	Binding affinity to recombinant heparanase catalytic stie (unknown origin) expressed in Escherichia coli BL21 (DE3) by surface plasmon resonance assay	2013	Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7	Hit identification of novel heparanase inhibitors by structure- and ligand-based approaches.
AID334634	Toxicity in Salmonella Typhimurium T98 at 600 ug/plate after 72 hrs by Ames assay in presence of Ames S-9 fraction
AID738327	Binding affinity to recombinant heparanase catalytic stie (unknown origin) expressed in Escherichia coli BL21 (DE3) by NMR analysis	2013	Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7	Hit identification of novel heparanase inhibitors by structure- and ligand-based approaches.
AID671762	Inhibition of HCV NS3 helicase overexpressed in Escherichia coli BL21(DE3) assessed as inhibition of DNA unwinding activity at 10 uM by FRET assay	2012	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12	Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13.
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.
AID588986	Inhibitors of transporters of clinical importance in the absorption and disposition of drugs, OATP1A2	2010	Nature reviews. Drug discovery, Mar, Volume: 9, Issue:3	Membrane transporters in drug development.
AID1466897	Antiproliferative activity against rat A7r5 cells at 100 uM after 24 hrs by MTT assay	2017	Bioorganic & medicinal chemistry letters, 06-15, Volume: 27, Issue:12	Anti-atherosclerotic activities of flavonoids from the flowers of Helichrysum arenarium L. MOENCH through the pathway of anti-inflammation.
AID681339	TP_TRANSPORTER: inhibition of Estrone-3-sulfate uptake (Estrone-3-sulfate: 10nM) in OATP2B1-expressing HEK293 cells	2005	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 33, Issue:4	Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B.
AID1466895	Antiproliferative activity against rat A7r5 cells at 10 uM after 24 hrs by MTT assay	2017	Bioorganic & medicinal chemistry letters, 06-15, Volume: 27, Issue:12	Anti-atherosclerotic activities of flavonoids from the flowers of Helichrysum arenarium L. MOENCH through the pathway of anti-inflammation.
AID379054	Inhibition of TNFalpha expression in LPS-stimulated human monocytes treated 30 mins before LPS challenge measured after 14 hrs by ELISA	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Polymethoxylated flavones derived from citrus suppress tumor necrosis factor-alpha expression by human monocytes.
AID386541	Stability in hank's balanced salt solution at 15 uM after 20 mins	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.
AID1466909	Anti-atherosclerosis activity in Sprague-Dawley rat thoracic aortic vascular ring endothelial injury model assessed as appearance of smooth vascular endothelial surface after 13 days by hematoxylin and eosin staining based assay	2017	Bioorganic & medicinal chemistry letters, 06-15, Volume: 27, Issue:12	Anti-atherosclerotic activities of flavonoids from the flowers of Helichrysum arenarium L. MOENCH through the pathway of anti-inflammation.
AID386547	Apparent permeability from apical to basolateral side in human Caco-2 cells assessed as drug recovery	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.
AID1466904	Anti-atherosclerosis activity in Sprague-Dawley rat thoracic aortic vascular ring endothelial injury model assessed as decrease in JNK2 level at 50 uM by ELISA	2017	Bioorganic & medicinal chemistry letters, 06-15, Volume: 27, Issue:12	Anti-atherosclerotic activities of flavonoids from the flowers of Helichrysum arenarium L. MOENCH through the pathway of anti-inflammation.
AID334637	Antimutagenic activity in Salmonella Typhimurium T98 assessed as inhibition of 2-aminoanthracene-induced mutation at 600 ug/plate after 72 hrs in presence of Ames S-9 fraction
AID1744554	Octanol-water distribution coefficient, log D of the compound at pH 7.4 after 1 hr by UV-VIS spectroscopic analysis	2021	Bioorganic & medicinal chemistry, 03-01, Volume: 33	A role of flavonoids in cytochrome c-cardiolipin interactions.
AID1884986	Potentiation of tetracyclin-induced antibacterial activity against Pseudomonas aeruginosa MTCC 2488 biofilm at 410 ug/ml incubated for 24 hrs pretreated with compound followed by tetracyclin addition by congo red binding assay	2022	Journal of medicinal chemistry, 07-14, Volume: 65, Issue:13	Small Carbohydrate Derivatives as Potent Antibiofilm Agents.
AID1884983	Antibacterial activity Actinobacillus actinomycetemcomitans ATCC 700685 assessed as bacterial growth inhibition incubated for 24 hrs by broth dilution assay	2022	Journal of medicinal chemistry, 07-14, Volume: 65, Issue:13	Small Carbohydrate Derivatives as Potent Antibiofilm Agents.
AID386543	Stability in hank's balanced salt solution at 15 uM after 120 mins	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.
AID1475100	Anti-diabetic activity in insulin-resistant human HepG2 cells assessed as increase in insulin-stimulated 2-NBDG uptake pretreated for 24 hrs followed by 2-NBDG addition measured after 30 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11	Structure-related protein tyrosine phosphatase 1B inhibition by naringenin derivatives.
AID405559	Inhibition of aromatase	2008	Journal of natural products, Jun, Volume: 71, Issue:6	Selective inhibition of aromatase by a dihydroisocoumarin from Xyris pterygoblephara.
AID1744553	Permeability constant, logPe of compound incubated for 2 to 30 hrs by PAMPA assay	2021	Bioorganic & medicinal chemistry, 03-01, Volume: 33	A role of flavonoids in cytochrome c-cardiolipin interactions.
AID1191919	Antioxidant activity assessed as DPPH free radical scavenging activity using plasma treated compound	2015	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 25, Issue:6	Enhancement of antioxidant effects of naringin after atmospheric pressure dielectric barrier discharge plasma treatment.
AID1466898	Anti-atherosclerosis activity in Sprague-Dawley rat thoracic aortic vascular ring endothelial injury model assessed as reduction in vascular endothelial proliferation after 13 days by hematoxylin and eosin staining based assay	2017	Bioorganic & medicinal chemistry letters, 06-15, Volume: 27, Issue:12	Anti-atherosclerotic activities of flavonoids from the flowers of Helichrysum arenarium L. MOENCH through the pathway of anti-inflammation.
AID1884985	Potentiation of ciprofloxacin-induced antibacterial activity against Pseudomonas aeruginosa MTCC 2488 biofilm at 410 ug/ml incubated for 24 hrs pretreated with compound followed by ciprofloxacin addition by congo red binding assay	2022	Journal of medicinal chemistry, 07-14, Volume: 65, Issue:13	Small Carbohydrate Derivatives as Potent Antibiofilm Agents.
AID699539	Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting	2012	Journal of medicinal chemistry, May-24, Volume: 55, Issue:10	Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions.
AID624616	Specific activity of expressed human recombinant UGT2B15	2000	Annual review of pharmacology and toxicology, , Volume: 40	Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID1466908	Anti-atherosclerosis activity in Sprague-Dawley rat thoracic aortic vascular ring endothelial injury model assessed as decrease in p38 level at 25 to 50 uM by ELISA	2017	Bioorganic & medicinal chemistry letters, 06-15, Volume: 27, Issue:12	Anti-atherosclerotic activities of flavonoids from the flowers of Helichrysum arenarium L. MOENCH through the pathway of anti-inflammation.
AID1475102	Anti-diabetic activity in insulin-resistant human HepG2 cells assessed as increase in insulin-stimulated 2-NBDG uptake at 50 uM pretreated for 24 hrs followed by 2-NBDG addition measured after 30 mins by fluorescence assay relative to control	2017	Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11	Structure-related protein tyrosine phosphatase 1B inhibition by naringenin derivatives.
AID1466906	Anti-inflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS/IFN-induced NO production at 10 to 20 uM measured 48 hrs post LPS/IFN challenge by Griess assay	2017	Bioorganic & medicinal chemistry letters, 06-15, Volume: 27, Issue:12	Anti-atherosclerotic activities of flavonoids from the flowers of Helichrysum arenarium L. MOENCH through the pathway of anti-inflammation.
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.
AID1884984	Antibacterial activity Porphyromonas gingivalis ATCC 33277 assessed as bacterial growth inhibition incubated for 24 hrs by broth dilution assay	2022	Journal of medicinal chemistry, 07-14, Volume: 65, Issue:13	Small Carbohydrate Derivatives as Potent Antibiofilm Agents.
AID699541	Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting	2012	Journal of medicinal chemistry, May-24, Volume: 55, Issue:10	Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions.
AID1466896	Antiproliferative activity against rat A7r5 cells at 50 uM after 24 hrs by MTT assay	2017	Bioorganic & medicinal chemistry letters, 06-15, Volume: 27, Issue:12	Anti-atherosclerotic activities of flavonoids from the flowers of Helichrysum arenarium L. MOENCH through the pathway of anti-inflammation.
AID379055	Cytotoxicity against human monocytes assessed as depletion of cellular LDH activity	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Polymethoxylated flavones derived from citrus suppress tumor necrosis factor-alpha expression by human monocytes.
AID1191920	Antioxidant activity assessed as ONOO- scavenging activity using plasma treated compound	2015	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 25, Issue:6	Enhancement of antioxidant effects of naringin after atmospheric pressure dielectric barrier discharge plasma treatment.
AID624606	Specific activity of expressed human recombinant UGT1A1	2000	Annual review of pharmacology and toxicology, , Volume: 40	Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID386551	Apparent permeability across PAMPA membrane assessed as drug recovery	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.
AID681338	TP_TRANSPORTER: inhibition of glibenclamide uptake (glibenclamide: 10nM) in OATP2B1-expressing HEK293 cells	2005	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 33, Issue:4	Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B.
AID386542	Stability in hank's balanced salt solution at 15 uM after 60 mins	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.
AID399646	Antiinflammatory activity against rat assessed as inhibition of carrageenan-induced edema
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.
AID1884987	Antibacterial activity against Pseudomonas aeruginosa MTCC 2488 biofilm at 410 ug/ml incubated for 24 hrs by congo red binding assay	2022	Journal of medicinal chemistry, 07-14, Volume: 65, Issue:13	Small Carbohydrate Derivatives as Potent Antibiofilm Agents.
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.
AID456318	DPPH radical scavenging activity assessed as trolox equivalent antioxidant capacity	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids.
AID1744547	Inhibition of cytochrome c (unknown origin) assessed as reduction in cyt c-CL complex formation at 10 uM incubated for 15 mins in presence of cardiolipin by Trp-59 fluorescence assay relative to control	2021	Bioorganic & medicinal chemistry, 03-01, Volume: 33	A role of flavonoids in cytochrome c-cardiolipin interactions.
AID682235	TP_TRANSPORTER: inhibition of Fexofenadine uptake (Fexofenadine: 1? uM, Naringin: 5 uM) in Oatp3-expressing HeLa cells	2002	Clinical pharmacology and therapeutics, Jan, Volume: 71, Issue:1	Fruit juices inhibit organic anion transporting polypeptide-mediated drug uptake to decrease the oral availability of fexofenadine.
AID1466902	Anti-atherosclerosis activity in Sprague-Dawley rat thoracic aortic vascular ring endothelial injury model assessed as decrease in VEGF level at 50 uM by ELISA	2017	Bioorganic & medicinal chemistry letters, 06-15, Volume: 27, Issue:12	Anti-atherosclerotic activities of flavonoids from the flowers of Helichrysum arenarium L. MOENCH through the pathway of anti-inflammation.
AID403810	Octanol-water partition coefficient, log POW of the compound	2005	Journal of natural products, Sep, Volume: 68, Issue:9	Efficiency of foam fractionation for the enrichment of nonpolar compounds from aqueous extracts of plant materials.
AID379219	Inhibition of human recombinant PTP1B	2006	Journal of natural products, Nov, Volume: 69, Issue:11	Protein tyrosine phosphatase-1B inhibitory activity of isoprenylated flavonoids isolated from Erythrina mildbraedii.
AID766850	Activation of recombinant human GIRK1/4 expressed in Xenopus oocytes by two-electrode voltage clamp method	2013	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 23, Issue:18	Discovery and SAR of a novel series of GIRK1/2 and GIRK1/4 activators.
AID1744549	Inhibition of cytochrome c (unknown origin) assessed as reduction reduction of cyt c from its ferric state to ferrous state at 10 uM incubated for 20 mins in presence of cardiolipin by UV-vis Spectrophotometric assay relative to control	2021	Bioorganic & medicinal chemistry, 03-01, Volume: 33	A role of flavonoids in cytochrome c-cardiolipin interactions.
AID671764	Inhibition of HCV NS3 helicase ATP hydrolysis activity overexpressed in Escherichia coli BL21(DE3) assessed as inhibition of inorganic phosphate release by AM/MG-based colometric analysis in the presence of M13 ssDNA	2012	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12	Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13.
AID386544	Stability in hank's balanced salt solution at 15 uM after 180 mins	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.
AID386545	Stability in hank's balanced salt solution at 15 uM after 24 hrs	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.
AID738326	Binding affinity to recombinant heparanase catalytic stie (unknown origin) expressed in Escherichia coli BL21 (DE3) by saturation transfer difference analysis	2013	Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7	Hit identification of novel heparanase inhibitors by structure- and ligand-based approaches.
AID1475098	Inhibition of PTP1B (unknown origin) using pNPP as substrate pretreated for 10 mins followed by substrate addition measured after 20 mins by spectrophotometric method	2017	Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11	Structure-related protein tyrosine phosphatase 1B inhibition by naringenin derivatives.
AID624608	Specific activity of expressed human recombinant UGT1A4	2000	Annual review of pharmacology and toxicology, , Volume: 40	Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID762435	Activation of GIRK (unknown origin)	2013	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 23, Issue:16	Discovery of 'molecular switches' within a GIRK activator scaffold that afford selective GIRK inhibitors.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	13 (1.45)	18.7374
1990's	42 (4.67)	18.2507
2000's	175 (19.47)	29.6817
2010's	463 (51.50)	24.3611
2020's	206 (22.91)	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	25 (2.70%)	5.53%
Reviews	35 (3.78%)	6.00%
Case Studies	2 (0.22%)	4.05%
Observational	0 (0.00%)	0.25%
Other	863 (93.30%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
2,3-dihydroxybenzoic acid 2,3-dihydroxybenzoic acid: RN given refers to parent cpd. dihydroxybenzoic acid : Any member of the class of hydroxybenzoic acids carrying two phenolic hydroxy groups on the benzene ring and its derivatives.. 2,3-dihydroxybenzoic acid : A dihydroxybenzoic acid that is benzoic acid substituted by hydroxy groups at positions 2 and 3. It occurs naturally in Phyllanthus acidus and in the aquatic fern Salvinia molesta.	2.11	1	0	dihydroxybenzoic acid	human xenobiotic metabolite; plant metabolite
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	4.24	5	0	catechols; dihydroxybenzoic acid	antineoplastic agent; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; human xenobiotic metabolite; plant metabolite
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.	2.13	1	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
4-hydroxyphenylacetic acid 4-hydroxyphenylacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	2.1	1	0	monocarboxylic acid; phenols	fungal metabolite; human metabolite; mouse metabolite; plant metabolite
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	3.1	1	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
aminolevulinic acid Aminolevulinic Acid: A compound produced from succinyl-CoA and GLYCINE as an intermediate in heme synthesis. It is used as a PHOTOCHEMOTHERAPY for actinic KERATOSIS.. 5-aminolevulinic acid : The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp.	3.15	1	0	4-oxo monocarboxylic acid; amino acid zwitterion; delta-amino acid	antineoplastic agent; dermatologic drug; Escherichia coli metabolite; human metabolite; mouse metabolite; photosensitizing agent; plant metabolite; prodrug; Saccharomyces cerevisiae metabolite
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.	2.15	1	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
adenine [no description available]	2.48	2	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
beta-alanine [no description available]	1.98	1	0	amino acid zwitterion; beta-amino acid	agonist; fundamental metabolite; human metabolite; inhibitor; neurotransmitter
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.	3.52	2	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.	3.1	1	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
betaine glycine betaine : The amino acid betaine derived from glycine.	2.15	1	0	amino-acid betaine; glycine derivative	fundamental metabolite
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	2.05	1	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	3.1	1	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	2.41	2	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
carnitine [no description available]	2.07	1	0	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).	2.61	2	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
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.	2.51	2	0	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.	3.8	2	1	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.	2.13	1	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	2.7	3	0	coumarins	fluorescent dye; human metabolite; plant metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	3.51	2	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	4.66	8	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
octanoic acid octanoic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #1764. octanoic acid : A straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid.	3.1	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human 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.	3.53	2	0	aminophenol	allergen; metabolite
3-hydroxybutyric acid 3-Hydroxybutyric Acid: BUTYRIC ACID substituted in the beta or 3 position. It is one of the ketone bodies produced in the liver.. 3-hydroxybutyric acid : A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics.	2.15	1	0	(omega-1)-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; hydroxybutyric acid	human metabolite
bupropion Bupropion: A propiophenone-derived antidepressant and antismoking agent that inhibits the uptake of DOPAMINE.. bupropion : An aromatic ketone that is propiophenone carrying a tert-butylamino group at position 2 and a chloro substituent at position 3 on the phenyl ring.	2.07	1	0	aromatic ketone; monochlorobenzenes; secondary amino compound	antidepressant; environmental contaminant; xenobiotic
creatine [no description available]	2.15	1	0	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical
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.	3.02	4	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	7.55	2	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
glycine [no description available]	7.46	2	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	7.47	2	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
histamine [no description available]	2.05	1	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	2.25	1	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	3.1	1	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
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.	2.07	1	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	2.07	1	0	diatomic iodine	nutrient
kynurenine Kynurenine: A metabolite of the essential amino acid tryptophan metabolized via the tryptophan-kynurenine pathway.. kynurenine : A ketone that is alanine in which one of the methyl hydrogens is substituted by a 2-aminobenzoyl group.	2.1	1	0	aromatic ketone; non-proteinogenic alpha-amino acid; substituted aniline	human metabolite
lipoamide Lipozyme: lipase from Rhizomucor miehei immobilized on anion exchange resin	2.03	1	0	dithiolanes; monocarboxylic acid amide	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.1	1	0	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	4.65	8	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]	2.07	1	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	2.47	2	0	metal allergen; nickel group element atom	epitope; micronutrient
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.07	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
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)	4.86	7	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
n,n-dimethylaniline N,N-dimethylaniline: RN given refers to parent cpd; structure. dimethylaniline : A methylaniline carrying at least two methyl groups.. N,N-dimethylaniline : A tertiary amine that is aniline in which the amino hydrogens are replaced by two methyl groups.	3.1	1	0	dimethylaniline; tertiary amine
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	3.1	1	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
palmitic acid Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.	2.76	3	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor; plant metabolite
phenol [no description available]	3.53	2	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	2.25	1	0	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
pyrogallol benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.	3.1	1	0	benzenetriol; phenolic donor	plant metabolite
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.	7.17	1	0	pyridinedicarboxylic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; NMDA receptor agonist
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	2.15	1	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
taurine [no description available]	2.06	1	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
tryptophan [no description available]	3.1	1	0	alpha-amino acid; amino acid zwitterion; aminoalkylindole; aromatic amino acid; polar amino acid	Daphnia magna 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.	2.76	3	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.	7.5	2	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
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	3.77	3	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
catechin [no description available]	3.8	3	0	hydroxyflavan
epibatidine [no description available]	2.07	1	0	alkaloid
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	3.49	2	0	p-menthane monoterpenoid; secondary alcohol	volatile oil component
1,2-dimethylhydrazine 1,2-Dimethylhydrazine: A DNA alkylating agent that has been shown to be a potent carcinogen and is widely used to induce colon tumors in experimental animals.. 1,2-dimethylhydrazine : A member of the class of hydrazines that is hydrazine in which one of the hydrogens attached to each nitrogen is replaced by a methyl group. A powerful DNA alkylating agent and carcinogen, it is used to induce colon cancer in laboratory rats and mice.	2.1	1	0	hydrazines	alkylating agent; carcinogenic agent
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.	3.14	5	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
hoe 33342 BXI-72: structure in first source	2.07	1	0	bibenzimidazole; N-methylpiperazine	fluorochrome
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source. PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish.	2	1	0	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
2-aminofluorene [no description available]	3.1	1	0
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.	3.18	5	0	C-nitro compound	antimycobacterial drug; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor; mycotoxin; neurotoxin
homovanillic acid Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.	3.1	1	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
phenytoin [no description available]	7.52	2	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
6-hydroxymelatonin 6-hydroxymelatonin : A member of the class of tryptamines that is melatonin with a hydroxy group substituent at position 6.	3.1	1	0	acetamides; tryptamines	metabolite; mouse metabolite
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.	2.05	1	0	dihydroxyflavone	antidepressant; antineoplastic agent; antioxidant; plant metabolite; tropomyosin-related kinase B receptor agonist
oxyquinoline Oxyquinoline: An antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action. It is also used as a reagent and metal chelator, as a carrier for radio-indium for diagnostic purposes, and its halogenated derivatives are used in addition as topical anti-infective agents and oral antiamebics.. quinolin-8-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes.	3.1	1	0	monohydroxyquinoline	antibacterial agent; antifungal agrochemical; antiseptic drug; iron chelator
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.	4.5	6	0	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
alpha-cyano-4-hydroxycinnamate alpha-cyano-4-hydroxycinnamate: specific inhibitor of pyruvate transport in rat liver mitochondria & human erythrocytes; structure	2.1	1	0
am 251 AM 251: an analog of SR141716A; structure given in first source. AM-251 : A carbohydrazide obtained by formal condensation of the carboxy group of 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid with the amino group of 1-aminopiperidine. An antagonist at the CB1 cannabinoid receptor.	3.15	1	0	amidopiperidine; carbohydrazide; dichlorobenzene; organoiodine compound; pyrazoles	antidepressant; antineoplastic agent; apoptosis inducer; CB1 receptor antagonist
amantadine amant: an antiviral compound consisting of an adamantane derivative chemically linked to a water-solube polyanioic matrix; structure in first source	3.57	2	0	adamantanes; primary aliphatic amine	analgesic; antiparkinson drug; antiviral drug; dopaminergic agent; NMDA receptor antagonist; non-narcotic analgesic
p-aminohippuric acid p-Aminohippuric Acid: The glycine amide of 4-aminobenzoic acid. Its sodium salt is used as a diagnostic aid to measure effective renal plasma flow (ERPF) and excretory capacity.. p-aminohippurate : A hippurate that is the conjugate base of p-aminohippuric acid, arising from deprotonation of the carboxy group.. p-aminohippuric acid : An N-acylglycine that is the 4-amino derivative of hippuric acid; used as a diagnostic agent in the measurement of renal plasma flow.	3.57	2	0	N-acylglycine	Daphnia magna metabolite
theophylline [no description available]	3.81	2	1	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
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.	3.53	2	0	carbotricyclic compound; tertiary amine	adrenergic uptake inhibitor; antidepressant; environmental contaminant; tropomyosin-related kinase B receptor agonist; xenobiotic
amoxapine Amoxapine: The N-demethylated derivative of the antipsychotic agent LOXAPINE that works by blocking the reuptake of norepinephrine, serotonin, or both; it also blocks dopamine receptors. Amoxapine is used for the treatment of depression.. amoxapine : A dibenzooxazepine compound having a chloro substituent at the 2-position and a piperazin-1-yl group at the 11-position.	7.41	1	0	dibenzooxazepine	adrenergic uptake inhibitor; antidepressant; dopaminergic antagonist; geroprotector; serotonin uptake inhibitor
acetovanillone apocynin : An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.17	1	0	acetophenones; aromatic ketone; methyl ketone	antirheumatic drug; EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug; plant metabolite
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.	3.1	1	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
astemizole Astemizole: Antihistamine drug now withdrawn from the market in many countries because of rare but potentially fatal side effects.. astemizole : A piperidine compound having a 2-(4-methoxyphenyl)ethyl group at the 1-position and an N-[(4-fluorobenzyl)benzimidazol-2-yl]amino group at the 4-position.	2.48	2	0	benzimidazoles; piperidines	anti-allergic agent; anticoronaviral agent; H1-receptor antagonist
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.	2.07	1	0	ethanolamines; monocarboxylic acid amide; propanolamine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; sympatholytic agent; xenobiotic
benzbromarone Benzbromarone: Uricosuric that acts by increasing uric acid clearance. It is used in the treatment of gout.. benzbromarone : 1-Benzofuran substituted at C-2 and C-3 by an ethyl group and a 3,5-dibromo-4-hydroxybenzoyl group respectively. An inhibitor of CYP2C9, it is used as an anti-gout medication.	2.07	1	0	1-benzofurans; aromatic ketone	uricosuric drug
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.	1.99	1	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
berberine [no description available]	7.57	2	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.	4.32	4	1	5-methoxyfurocoumarin; organic heterotricyclic compound; psoralens	hepatoprotective agent; plant metabolite
beta-naphthoflavone beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.	3.1	1	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
bumetanide [no description available]	4.04	2	0	amino acid; benzoic acids; sulfonamide	diuretic; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor
buspirone Buspirone: An anxiolytic agent and serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the BENZODIAZAPINES, but it has an efficacy comparable to DIAZEPAM.. buspirone : An azaspiro compound that is 8-azaspiro[4.5]decane-7,9-dione substituted at the nitrogen atom by a 4-(piperazin-1-yl)butyl group which in turn is substituted by a pyrimidin-2-yl group at the N(4) position.	2.07	1	0	azaspiro compound; N-alkylpiperazine; N-arylpiperazine; organic heteropolycyclic compound; piperidones; pyrimidines	anxiolytic drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; sedative; serotonergic agonist
caffeine [no description available]	9.82	7	1	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.	4.64	8	0	aromatic ether; nitrile; polyether; tertiary amino compound
candesartan cilexetil candesartan cilexetil: a prodrug which is metabolized to an active form candesartan to exert its biological effects	2.81	3	0	biphenyls
candesartan candesartan: a nonpeptide angiotensin II receptor antagonist. candesartan : A benzimidazolecarboxylic acid that is 1H-benzimidazole-7-carboxylic acid substituted by an ethoxy group at position 2 and a ({2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl}methyl) group at position 1. It is a angiotensin receptor antagonist used for the treatment of hypertension.	2.07	1	0	benzimidazolecarboxylic acid; biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
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.	3.53	2	0	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
celecoxib [no description available]	8.9	3	0	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
celiprolol Celiprolol: A cardioselective beta-1 adrenergic antagonist that has intrinsic sympathomimetic activity. It is used in the management of ANGINA PECTORIS and HYPERTENSION.	2.08	1	0	aromatic ketone
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.	3.57	2	0	ether; monocarboxylic acid; monochlorobenzenes; piperazines	anti-allergic agent; environmental contaminant; H1-receptor antagonist; xenobiotic
chelerythrine chelerythrine : A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae.	2.07	1	0	benzophenanthridine alkaloid; organic cation	antibacterial agent; antineoplastic agent; EC 2.7.11.13 (protein kinase C) inhibitor
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.	2.07	1	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
chlorpheniramine Chlorpheniramine: A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than PROMETHAZINE.. chlorphenamine : A tertiary amino compound that is propylamine which is substituted at position 3 by a pyridin-2-yl group and a p-chlorophenyl group and in which the hydrogens attached to the nitrogen are replaced by methyl groups. A histamine H1 antagonist, it is used to relieve the symptoms of hay fever, rhinitis, urticaria, and asthma.	3.1	1	0	monochlorobenzenes; pyridines; tertiary amino compound	anti-allergic agent; antidepressant; antipruritic drug; H1-receptor antagonist; histamine antagonist; serotonin uptake inhibitor
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.	3.53	2	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
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.	2.07	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.	3.57	2	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
ciprofibrate [no description available]	3.1	1	0	cyclopropanes; monocarboxylic acid; organochlorine compound	antilipemic drug
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.	8.61	2	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
cisapride Cisapride: A substituted benzamide used for its prokinetic properties. It is used in the management of gastroesophageal reflux disease, functional dyspepsia, and other disorders associated with impaired gastrointestinal motility. (Martindale The Extra Pharmacopoeia, 31st ed). cisapride : The amide resulting from formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with cis-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-amine. It has been used (as its monohydrate or as its tartrate) for the treatment of gastro-oesophageal reflux disease and for non-ulcer dyspepsia, but its propensity to cause cardiac arrhythmias resulted in its complete withdrawal from many countries, including the U.K., and restrictions on its use elsewhere.	2.08	1	0	benzamides
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	3.1	1	0	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist
clofibric acid Clofibric Acid: An antilipemic agent that is the biologically active metabolite of CLOFIBRATE.. clofibric acid : A monocarboxylic acid that is isobutyric acid substituted at position 2 by a p-chlorophenoxy group. It is a metabolite of the drug clofibrate.	3.1	1	0	aromatic ether; monocarboxylic acid; monochlorobenzenes	anticholesteremic drug; antilipemic drug; antineoplastic agent; herbicide; marine xenobiotic metabolite; PPARalpha agonist
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.	1.98	1	0	clonidine; imidazoline
4-chloro-N-(2,6-dimethyl-1-piperidinyl)-3-sulfamoylbenzamide [no description available]	3.1	1	0	sulfonamide
clotrimazole [no description available]	2.07	1	0	conazole antifungal drug; imidazole antifungal drug; imidazoles; monochlorobenzenes	antiinfective agent; environmental contaminant; xenobiotic
4-cresol 4-cresol: RN given refers to parent cpd. p-cresol : A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals.	3.1	1	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
cyproheptadine Cyproheptadine: A serotonin antagonist and a histamine H1 blocker used as antipruritic, appetite stimulant, antiallergic, and for the post-gastrectomy dumping syndrome, etc.. cyproheptadine : The product resulting from the formal oxidative coupling of position 5 of 5H-dibenzo[a,d]cycloheptene with position 4 of 1-methylpiperidine resulting in the formation of a double bond between the two fragments. It is a sedating antihistamine with antimuscarinic and calcium-channel blocking actions. It is used (particularly as the hydrochloride sesquihydrate) for the relief of allergic conditions including rhinitis, conjunctivitis due to inhalant allergens and foods, urticaria and angioedema, and in pruritic skin disorders. Unlike other antihistamines, it is also a seratonin receptor antagonist, making it useful in conditions such as vascular headache and anorexia.	3.1	1	0	piperidines; tertiary amine	anti-allergic agent; antipruritic drug; gastrointestinal drug; H1-receptor antagonist; serotonergic antagonist
danthron danthron: structure. chrysazin : A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8.	3.1	1	0	dihydroxyanthraquinone	apoptosis inducer; plant metabolite
dapsone [no description available]	3.1	1	0	substituted aniline; sulfone	anti-inflammatory drug; antiinfective agent; antimalarial; leprostatic drug
decanoic acid decanoate : A fatty acid anion 10:0 that is the conjugate base of decanoic acid.. decanoic acid : A C10, straight-chain saturated fatty acid.	3.1	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; anti-inflammatory agent; antibacterial agent; human metabolite; plant metabolite; volatile oil component
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
deferiprone Deferiprone: A pyridone derivative and iron chelator that is used in the treatment of IRON OVERLOAD in patients with THALASSEMIA.. deferiprone : A member of the class of 4-pyridones that is pyridin-4(1H)-one substituted at positions 1 and 2 by methyl groups and at position 3 by a hydroxy group. A lipid-soluble iron-chelator used for treatment of thalassaemia.	2.05	1	0	4-pyridones	iron chelator; protective agent
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.	3.53	2	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.	2.07	1	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
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.	8.89	3	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
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.	3.1	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
diphenhydramine Diphenhydramine: A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects.. diphenhydramine : An ether that is the benzhydryl ether of 2-(dimethylamino)ethanol. It is a H1-receptor antagonist used as a antipruritic and antitussive drug.. antitussive : An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.	3.1	1	0	ether; tertiary amino compound	anti-allergic agent; antidyskinesia agent; antiemetic; antiparkinson drug; antipruritic drug; antitussive; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; oneirogen; sedative
dipyridamole Dipyridamole: A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752). dipyridamole : A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.	2.07	1	0	piperidines; pyrimidopyrimidine; tertiary amino compound; tetrol	adenosine phosphodiesterase inhibitor; EC 3.5.4.4 (adenosine deaminase) inhibitor; platelet aggregation inhibitor; vasodilator agent
disopyramide Disopyramide: A class I anti-arrhythmic agent (one that interferes directly with the depolarization of the cardiac membrane and thus serves as a membrane-stabilizing agent) with a depressant action on the heart similar to that of guanidine. It also possesses some anticholinergic and local anesthetic properties.. disopyramide : A monocarboxylic acid amide that is butanamide substituted by a diisopropylamino group at position 4, a phenyl group at position 2 and a pyridin-2-yl group at position 2. It is used as a anti-arrhythmia drug.	3.57	2	0	monocarboxylic acid amide; pyridines; tertiary amino compound	anti-arrhythmia drug
disulfiram [no description available]	2.07	1	0	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor
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.	9.32	5	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
doxazosin Doxazosin: A prazosin-related compound that is a selective alpha-1-adrenergic blocker.. doxazosin : A member of the class of quinazolines that is quinazoline substituted by an amino group at position 4, methoxy groups at positions 6 and 7 and a piperazin-1-yl group at position 2 which in turn is substituted by a 2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl group at position 4. An antihypertensive agent, it is used in the treatment of high blood pressure.	2.07	1	0	aromatic amine; benzodioxine; monocarboxylic acid amide; N-acylpiperazine; N-arylpiperazine; quinazolines	alpha-adrenergic antagonist; antihyperplasia drug; antihypertensive agent; antineoplastic agent; vasodilator agent
doxepin Doxepin: A dibenzoxepin tricyclic compound. It displays a range of pharmacological actions including maintaining adrenergic innervation. Its mechanism of action is not fully understood, but it appears to block reuptake of monoaminergic neurotransmitters into presynaptic terminals. It also possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors.. doxepin : A dibenzooxepine that is 6,11-dihydrodibenzo[b,e]oxepine substituted by a 3-(dimethylamino)propylidene group at position 11. It is used as an antidepressant drug.	3.1	1	0	dibenzooxepine; tertiary amino compound	antidepressant
doxylamine Doxylamine: Histamine H1 antagonist with pronounced sedative properties. It is used in allergies and as an antitussive, antiemetic, and hypnotic. Doxylamine has also been administered in veterinary applications and was formerly used in PARKINSONISM.	3.1	1	0	pyridines; tertiary amine	anti-allergic agent; antiemetic; antitussive; cholinergic antagonist; H1-receptor antagonist; histamine antagonist; sedative
dipropizine [no description available]	2.08	1	0	piperazines
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.	2.07	1	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.	4.07	4	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.	2.1	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.	3.1	1	0	aromatic ether; aromatic ketone; dichlorobenzene; monocarboxylic acid	EC 2.5.1.18 (glutathione transferase) inhibitor; ion transport inhibitor; loop diuretic
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.	6.5	5	3	dichlorobenzene; dihydropyridine; ethyl ester; methyl ester	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
fendiline Fendiline: Coronary vasodilator; inhibits calcium function in muscle cells in excitation-contraction coupling; proposed as antiarrhythmic and antianginal agents.	2.07	1	0	diarylmethane
fenofibrate Pharmavit: a polyvitamin product, comprising vitamins A, D2, B1, B2, B6, C, E, nicotinamide, & calcium pantothene; may be a promising agent for application to human populations exposed to carcinogenic and genetic hazards of ionizing radiation; RN from CHEMLINE	2.07	1	0	aromatic ether; chlorobenzophenone; isopropyl ester; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic
fenoprofen Fenoprofen: A propionic acid derivative that is used as a non-steroidal anti-inflammatory agent.. fenoprofen : A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 2 is substituted by a 3-phenoxyphenyl group. A non-steroidal anti-inflammatory drug, the dihydrate form of the calcium salt is used for the management of mild to moderate pain and for the relief of pain and inflammation associated with disorders such as arthritis. It is pharmacologically similar to aspirin, but causes less gastrointestinal bleeding.	3.1	1	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; non-narcotic analgesic; non-steroidal anti-inflammatory drug
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.	3.1	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.	2.07	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.	6.21	5	2	piperidines; tertiary amine	anti-allergic agent; H1-receptor antagonist
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.	2.07	1	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
fluphenazine [no description available]	3.1	1	0	N-alkylpiperazine; organofluorine compound; phenothiazines	anticoronaviral agent; dopaminergic antagonist; phenothiazine antipsychotic drug
fluorescite fluorescein (acid form) : A xanthene dye that is highly fluorescent and commonly used as a fluorescent tracer.	3.1	1	0	benzoic acids; cyclic ketone; hydroxy monocarboxylic acid; organic heterotricyclic compound; phenols; xanthene dye	fluorescent dye; radioopaque medium
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.	7.6	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.	2.07	1	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
flutamide Flutamide: An antiandrogen with about the same potency as cyproterone in rodent and canine species.	2.07	1	0	(trifluoromethyl)benzenes; monocarboxylic acid amide	androgen antagonist; antineoplastic agent
furafylline [no description available]	2.07	1	0	oxopurine
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.	4.34	3	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
gemfibrozil [no description available]	2.07	1	0	aromatic ether	antilipemic drug
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.	7.57	2	0
glipizide Glipizide: An oral hypoglycemic agent which is rapidly absorbed and completely metabolized.. glipizide : An N-sulfonylurea that is glyburide in which the (5-chloro-2-methoxybenzoyl group is replaced by a (5-methylpyrazin-2-yl)carbonyl group. An oral hypoglycemic agent, it is used in the treatment of type 2 diabetes mellitus.	2.07	1	0	aromatic amide; monocarboxylic acid amide; N-sulfonylurea; pyrazines	EC 2.7.1.33 (pantothenate kinase) inhibitor; hypoglycemic agent; insulin secretagogue
glutaral Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.	2.07	1	0	dialdehyde	cross-linking reagent; disinfectant; fixative
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	4.07	4	0	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
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
1-(5-isoquinolinesulfonyl)-2-methylpiperazine 1-(5-Isoquinolinesulfonyl)-2-Methylpiperazine: A specific protein kinase C inhibitor, which inhibits superoxide release from human neutrophils (PMN) stimulated with phorbol myristate acetate or synthetic diacylglycerol.. 1-(5-isoquinolinesulfonyl)-2-methylpiperazine : A member of the class of N-sulfonylpiperazines that is 2-methylpiperazine substituted at position 1 by a 5-isoquinolinesulfonyl group.	2.39	2	0	isoquinolines; N-sulfonylpiperazine	EC 2.7.11.13 (protein kinase C) inhibitor
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.	7.31	1	0	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
hydroxyurea [no description available]	2.06	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
hypericin [no description available]	2.07	1	0
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	3.82	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
ifosfamide [no description available]	7	1	0	ifosfamides	alkylating agent; antineoplastic agent; environmental contaminant; immunosuppressive agent; xenobiotic
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.	3.53	2	0	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
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.	2.07	1	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.	9.23	5	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
1-methyl-3-isobutylxanthine 1-Methyl-3-isobutylxanthine: A potent cyclic nucleotide phosphodiesterase inhibitor; due to this action, the compound increases cyclic AMP and cyclic GMP in tissue and thereby activates CYCLIC NUCLEOTIDE-REGULATED PROTEIN KINASES. 3-isobutyl-1-methylxanthine : An oxopurine that is xanthine which is substituted at positions 1 and 3 by methyl and isobutyl groups, respectively.	2.44	2	0	3-isobutyl-1-methylxanthine
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).	2.07	1	0	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.	3.43	7	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
isradipine Isradipine: A potent antagonist of CALCIUM CHANNELS that is highly selective for VASCULAR SMOOTH MUSCLE. It is effective in the treatment of chronic stable angina pectoris, hypertension, and congestive cardiac failure.	2.07	1	0	benzoxadiazole; dihydropyridine; isopropyl ester; methyl ester
itraconazole [no description available]	2.07	1	0	piperazines
staurosporine aglycone staurosporine aglycone: metabolite from culture broth of Nocardiopsis sp.; a neurotrophin antag; inhibits BDNF TrkB receptor	1.99	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).	2.07	1	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.	7.25	1	0	cyclohexanones; monochlorobenzenes; secondary amino compound	analgesic; environmental contaminant; intravenous anaesthetic; neurotoxin; NMDA receptor antagonist; xenobiotic
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.	2.48	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.	3.1	1	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.	3.1	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.	2.07	1	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.	3.53	2	0	benzamides; benzenes; phenols; primary carboxamide; salicylamides; secondary alcohol; secondary amino compound
lamotrigine [no description available]	3.53	2	0	1,2,4-triazines; dichlorobenzene; primary arylamine	anticonvulsant; antidepressant; antimanic drug; calcium channel blocker; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; excitatory amino acid antagonist; geroprotector; non-narcotic analgesic; xenobiotic
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.	2.07	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
lauric acid dodecanoic acid : A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.	3.1	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial 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
lomefloxacin lomefloxacin: structure given in first source. lomefloxacin : A fluoroquinolone antibiotic, used (generally as the hydrochloride salt) to treat bacterial infections including bronchitis and urinary tract infections. It is also used to prevent urinary tract infections prior to surgery.	7.04	1	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antimicrobial agent; antitubercular agent; photosensitizing agent
loperamide Loperamide: One of the long-acting synthetic ANTIDIARRHEALS; it is not significantly absorbed from the gut, and has no effect on the adrenergic system or central nervous system, but may antagonize histamine and interfere with acetylcholine release locally.. loperamide : A synthetic piperidine derivative, effective against diarrhoea resulting from gastroenteritis or inflammatory bowel disease.	3.57	2	0	monocarboxylic acid amide; monochlorobenzenes; piperidines; tertiary alcohol	anticoronaviral agent; antidiarrhoeal drug; mu-opioid receptor agonist
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.	2.07	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.	3.1	1	0	benzodiazepine
losartan Losartan: An antagonist of ANGIOTENSIN TYPE 1 RECEPTOR with antihypertensive activity due to the reduced pressor effect of ANGIOTENSIN II.. losartan : A biphenylyltetrazole where a 1,1'-biphenyl group is attached at the 5-position and has an additional trisubstituted imidazol-1-ylmethyl group at the 4'-position	3.1	1	0	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist
loxapine Loxapine: An antipsychotic agent used in SCHIZOPHRENIA.	3.1	1	0	dibenzooxazepine	antipsychotic agent; dopaminergic antagonist
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	2.17	1	0	chromones; morpholines; organochlorine compound	autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector
malathion Malathion: A wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes.. malathion : A racemate comprising equimolar amounts of (R) and (S)-malathion. It is a broad spectrum organophosphate proinsecticide used to control a wide range of pests including Coleoptera, Diptera, fruit flies, mosquitos and spider mites.. diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate : A diester that is diethyl succinate in which position 2 is substituted by a (dimethoxyphosphorothioyl)thio group.	7.31	1	0	diester; ethyl ester; organic thiophosphate
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
meperidine Meperidine: A narcotic analgesic that can be used for the relief of most types of moderate to severe pain, including postoperative pain and the pain of labor. Prolonged use may lead to dependence of the morphine type; withdrawal symptoms appear more rapidly than with morphine and are of shorter duration.. pethidine : A piperidinecarboxylate ester that is piperidine which is substituted by a methyl group at position 1 and by phenyl and ethoxycarbonyl groups at position 4. It is an analgesic which is used for the treatment of moderate to severe pain, including postoperative pain and labour pain.	3.1	1	0	ethyl ester; piperidinecarboxylate ester; tertiary amino compound	antispasmodic drug; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic
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.	2.07	1	0	imidazolidine-2,4-dione	anticonvulsant
mesalamine Mesalamine: An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed). mesalamine : A monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position.	3.1	1	0	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug
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.	4.1	4	0	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
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.	2.95	4	0	aromatic ether; psoralens	antineoplastic agent; cross-linking reagent; dermatologic drug; photosensitizing agent; plant metabolite
metoprolol Metoprolol: A selective adrenergic beta-1 blocking agent that is commonly used to treat ANGINA PECTORIS; HYPERTENSION; and CARDIAC ARRHYTHMIAS.. metoprolol : A propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a 4-(2-methoxyethyl)phenoxy group at position 1.	2.07	1	0	aromatic ether; propanolamine; secondary alcohol; secondary amino compound	antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; geroprotector; 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.	2.61	2	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.	3.1	1	0	aromatic ether; primary amino compound	anti-arrhythmia drug
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.	2.07	1	0	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative
mitoxantrone Mitoxantrone: An anthracenedione-derived antineoplastic agent.. mitoxantrone : A dihydroxyanthraquinone that is 1,4-dihydroxy-9,10-anthraquinone which is substituted by 6-hydroxy-1,4-diazahexyl groups at positions 5 and 8.	4.34	3	0	dihydroxyanthraquinone	analgesic; antineoplastic agent
moclobemide Moclobemide: A reversible inhibitor of monoamine oxidase type A; (RIMA); (see MONOAMINE OXIDASE INHIBITORS) that has antidepressive properties.. moclobemide : A member of the class of benzamides that is benzamide substituted by a chloro group at position 4 and a 2-(morpholin-4-yl)ethyl group at the nitrogen atom. It acts as a reversible monoamine oxidase inhibitor and is used in the treatment of depression.	2.07	1	0	benzamides; monochlorobenzenes; morpholines	antidepressant; environmental contaminant; xenobiotic
myristicin myristicin: asaricin is an isomer; structure; a methylene dioxy version of elemicin;	2.07	1	0	organic molecular entity	metabolite
nalidixic acid [no description available]	2.07	1	0	1,8-naphthyridine derivative; monocarboxylic acid; quinolone antibiotic	antibacterial drug; antimicrobial agent; DNA synthesis inhibitor
nefazodone nefazodone: may be useful as an opiate adjunct	2.07	1	0	aromatic ether; monochlorobenzenes; N-alkylpiperazine; N-arylpiperazine; triazoles	alpha-adrenergic antagonist; analgesic; antidepressant; serotonergic antagonist; serotonin uptake inhibitor
nicardipine Nicardipine: A potent calcium channel blockader with marked vasodilator action. It has antihypertensive properties and is effective in the treatment of angina and coronary spasms without showing cardiodepressant effects. It has also been used in the treatment of asthma and enhances the action of specific antineoplastic agents.. nicardipine : A racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension.. 2-[benzyl(methyl)amino]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate : A dihydropyridine that is 1,4-dihydropyridine substituted by a methyl, {2-[benzyl(methyl)amino]ethoxy}carbonyl, 3-nitrophenyl, methoxycarbonyl and methyl groups at positions 2, 3, 4, 5 and 6, respectively.	2.07	1	0	benzenes; C-nitro compound; diester; dihydropyridine; methyl ester; tertiary amino compound
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	3.8	3	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
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.	8.85	2	1	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
nisoldipine Nisoldipine: A dihydropyridine calcium channel antagonist that acts as a potent arterial vasodilator and antihypertensive agent. It is also effective in patients with cardiac failure and angina.. nisoldipine : A racemate consisting of equimolar amounts of (R)- and (S)-nisoldipine. A calcium channel blocker, it is used in the treatment of hypertension and angina pectoris.. methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate : A dihydropyridine that is 1,4-dihydropyridine which is substituted by methyl groups at positions 2 and 6, a methoxycarbonyl group at position 3, an o-nitrophenyl group at position 4, and an isobutoxycarbonyl group at position 5. The racemate, a calcium channel blocker, is used in the treatment of hypertension and angina pectoris.	8.78	2	1	C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; methyl ester
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.	3.08	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
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.	3.1	1	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
ofloxacin Ofloxacin: A synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA GYRASE, halting DNA REPLICATION.. 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid : An oxazinoquinoline that is 2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one substituted by methyl, carboxy, fluoro, and 4-methylpiperazin-1-yl groups at positions 3, 6, 9, and 10, respectively.. ofloxacin : A racemate comprising equimolar amounts of levofloxacin and dextrofloxacin. It is a synthetic fluoroquinolone antibacterial agent which inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.	2.07	1	0	3-oxo monocarboxylic acid; N-arylpiperazine; N-methylpiperazine; organofluorine compound; oxazinoquinoline
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.	2.07	1	0	aromatic ether; benzimidazoles; pyridines; sulfoxide
ondansetron Ondansetron: A competitive serotonin type 3 receptor antagonist. It is effective in the treatment of nausea and vomiting caused by cytotoxic chemotherapy drugs, including cisplatin, and has reported anxiolytic and neuroleptic properties.	2.07	1	0	carbazoles
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.	3.1	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).	2.13	1	0	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin
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.	3.1	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.	3.1	1	0	aminobenzoic acid; phenols	antitubercular agent
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.	2.07	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
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'.	2.72	3	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
phenacetin Saridon: contains phenacetin, caffeine, propyphenazone & pyrithyldione	2.07	1	0	acetamides; aromatic ether	cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug
pheniramine Pheniramine: One of the HISTAMINE H1 ANTAGONISTS with little sedative action. It is used in treatment of hay fever, rhinitis, allergic dermatoses, and pruritus.	3.1	1	0	pyridines; tertiary amino compound
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	3.53	2	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
phenolphthalein Phenolphthalein: An acid-base indicator which is colorless in acid solution, but turns pink to red as the solution becomes alkaline. It is used medicinally as a cathartic.	3.1	1	0	phenols
phenolsulfonphthalein Phenolsulfonphthalein: Red dye, pH indicator, and diagnostic aid for determination of renal function. It is used also for studies of the gastrointestinal and other systems.. phenol red : 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 4-hydroxyphenyl groups. A pH indicator changing colour from yellow below pH 6.8 to bright pink above pH 8.2, it is commonly used as an indicator in cell cultures and in home swimming pool test kits. It is also used in the (now infrequently performed) phenolsulfonphthalein (PSP) test for estimation of overall blood flow through the kidney.	3.1	1	0	2,1-benzoxathiole; arenesulfonate ester; phenols; sultone	acid-base indicator; diagnostic agent; two-colour indicator
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.	3.53	2	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]	2.47	2	0	dihydrochalcones	antineoplastic agent; plant metabolite
pilsicainide pilsicainide: structure given in first source. pilsicainide : A secondary carboxamide resulting from the formal condensation of the amino group of 2,6-dimethylaniline with the carboxy group of (tetrahydro-1H-pyrrolizin-7a(5H)-yl)acetic acid. It is a sodium channel blocker which is used as an antiarrhythmic drug for the management of atrial tachyarrhythmias in Japan.	3.57	2	0	organic heterobicyclic compound; secondary carboxamide	anti-arrhythmia drug; sodium channel blocker
pindolol Pindolol: A moderately lipophilic beta blocker (ADRENERGIC BETA-ANTAGONISTS). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638). pindolol : A member of the class of indols which is the 2-hydroxy-3-(isopropylamino)propyl ether derivative of 1H-indol-4-ol.	3.57	2	0	indoles; secondary amine	antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist; serotonergic antagonist; vasodilator agent
pioglitazone Pioglitazone: A thiazolidinedione and PPAR GAMMA agonist that is used in the treatment of TYPE 2 DIABETES MELLITUS.. pioglitazone : A member of the class of thiazolidenediones that is 1,3-thiazolidine-2,4-dione substituted by a benzyl group at position 5 which in turn is substituted by a 2-(5-ethylpyridin-2-yl)ethoxy group at position 4 of the phenyl ring. It exhibits hypoglycemic activity.	2.07	1	0	aromatic ether; pyridines; thiazolidinediones	antidepressant; cardioprotective agent; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; geroprotector; hypoglycemic agent; insulin-sensitizing drug; PPARgamma agonist; xenobiotic
ono 1078 pranlukast: SRS-A antagonist; leukotriene D4 receptor antagonist	2.21	1	0	chromones
prazosin Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.. prazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.	2.07	1	0	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
probenecid Probenecid: The prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy.. probenecid : A sulfonamide in which the nitrogen of 4-sulfamoylbenzoic acid is substituted with two propyl groups.	4.34	3	0	benzoic acids; sulfonamide	uricosuric drug
probucol Probucol: A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).. probucol : A dithioketal that is propane-2,2-dithiol in which the hydrogens attached to both sulfur atoms are replaced by 3,5-di-tert-butyl-4-hydroxyphenyl groups. An anticholesteremic drug with antioxidant and anti-inflammatory properties, it is used to treat high levels of cholesterol in blood.	7.01	1	0	dithioketal; polyphenol	anti-inflammatory drug; anticholesteremic drug; antilipemic drug; antioxidant; cardiovascular drug
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.	3.57	2	0	benzamides	anti-arrhythmia drug; platelet aggregation inhibitor; sodium channel blocker
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.	3.1	1	0	phenothiazines; tertiary amine	anti-allergic agent; anticoronaviral agent; antiemetic; antipruritic drug; H1-receptor antagonist; local anaesthetic; sedative
propidium Propidium: Quaternary ammonium analog of ethidium; an intercalating dye with a specific affinity to certain forms of DNA and, used as diiodide, to separate them in density gradients; also forms fluorescent complexes with cholinesterase which it inhibits.	1.99	1	0	phenanthridines; quaternary ammonium ion	fluorochrome; intercalator
propofol Propofol: An intravenous anesthetic agent which has the advantage of a very rapid onset after infusion or bolus injection plus a very short recovery period of a couple of minutes. (From Smith and Reynard, Textbook of Pharmacology, 1992, 1st ed, p206). Propofol has been used as ANTICONVULSANTS and ANTIEMETICS.. propofol : A phenol resulting from the formal substitution of the hydrogen at the 2 position of 1,3-diisopropylbenzene by a hydroxy group.	3.1	1	0	phenols	anticonvulsant; antiemetic; intravenous anaesthetic; radical scavenger; 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.	3.53	2	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
propyl gallate Propyl Gallate: Antioxidant for foods, fats, oils, ethers, emulsions, waxes, and transformer oils.	3.1	1	0	trihydroxybenzoic acid
pyrilamine Pyrilamine: A histamine H1 antagonist. It has mild hypnotic properties and some local anesthetic action and is used for allergies (including skin eruptions) both parenterally and locally. It is a common ingredient of cold remedies.. mepyramine : An ethylenediamine derivative that is ethylenediamine in which one of the amino nitrogens is substituted by two methyl groups and the remaining amino nitrogen is substituted by a 4-methoxybenzyl and a pyridin-2-yl group.	3.1	1	0	aromatic ether; ethylenediamine derivative	H1-receptor antagonist
1,2,5,8-tetrahydroxy anthraquinone 1,2,5,8-tetrahydroxy anthraquinone: structure in first source. quinalizarin : A tetrahydroxyanthraquinone having the four hydroxy groups at the 1-, 2-, 5- and 8-positions.	3.1	1	0	tetrahydroxyanthraquinone	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor
ranitidine [no description available]	3.15	1	0	aralkylamine
saccharin Saccharin: Flavoring agent and non-nutritive sweetener.. saccharin : A 1,2-benzisothiazole having a keto-group at the 3-position and two oxo substituents at the 1-position. It is used as an artificial sweetening agent.	3.86	2	1	1,2-benzisothiazole; N-sulfonylcarboxamide	environmental contaminant; sweetening agent; xenobiotic
salicylamide salamide: a major impurity of hydrochlorothiazide; structure in first source	3.1	1	0	phenols; salicylamides	antirheumatic drug; non-narcotic analgesic
sanguinarine benzophenanthridine alkaloid : A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.	2.48	2	0	alkaloid antibiotic; benzophenanthridine alkaloid; botanical anti-fungal agent
sb 202190 4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole: structure given in first source; inhibits p38 MAP kinase	2.06	1	0	imidazoles; organofluorine compound; phenols; pyridines	apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor
sodium fluoride [no description available]	2.6	1	0	fluoride salt	mutagen
sotalol Sotalol: An adrenergic beta-antagonist that is used in the treatment of life-threatening arrhythmias.. sotalol : A sulfonamide that is N-phenylmethanesulfonamide in which the phenyl group is substituted at position 4 by a 1-hydroxy-2-(isopropylamino)ethyl group. It has both beta-adrenoreceptor blocking (Vaughan Williams Class II) and cardiac action potential duration prolongation (Vaughan Williams Class III) antiarrhythmic properties. It is used (usually as the hydrochloride salt) for the management of ventricular and supraventricular arrhythmias.	2.07	1	0	ethanolamines; secondary alcohol; secondary amino compound; sulfonamide	anti-arrhythmia drug; beta-adrenergic antagonist; environmental contaminant; xenobiotic
imatinib [no description available]	3.15	1	0	aromatic amine; benzamides; N-methylpiperazine; pyridines; pyrimidines	antineoplastic agent; apoptosis inducer; tyrosine kinase inhibitor
streptonigrin [no description available]	2.07	1	0	pyridines; quinolone	antimicrobial agent; antineoplastic agent
sulfadimethoxine Sulfadimethoxine: A sulfanilamide that is used as an anti-infective agent.. sulfadimethoxine : A sulfonamide consisting of pyrimidine having methoxy substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.	3.1	1	0	aromatic ether; pyrimidines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; antimicrobial agent; drug allergen; environmental contaminant; xenobiotic
sulfaphenazole Sulfaphenazole: A sulfonilamide anti-infective agent.. sulfaphenazole : A sulfonamide that is sulfanilamide in which the sulfonamide nitrogen is substituted by a 1-phenyl-1H-pyrazol-5-yl group. It is a selective inhibitor of cytochrome P450 (CYP) 2C9 isozyme, and antibacterial agent.	2.07	1	0	primary amino compound; pyrazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial drug; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor; P450 inhibitor
sulfasalazine Sulfasalazine: A drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see MESALAMINE) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907). sulfasalazine : An azobenzene consisting of diphenyldiazene having a carboxy substituent at the 4-position, a hydroxy substituent at the 3-position and a 2-pyridylaminosulphonyl substituent at the 4'-position.	2.07	1	0
sulfathiazole Sulfathiazole: A sulfathiazole compound that is used as a short-acting anti-infective agent. It is no longer commonly used systemically due to its toxicity, but may still be applied topically in combination with other drugs for the treatment of vaginal and skin infections, and is still used in veterinary medicine.. sulfathiazole : A 1,3-thiazole compound having a 4-aminobenzenesulfonamido group at the 2-position.	3.1	1	0	1,3-thiazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; xenobiotic
sulfinpyrazone Sulfinpyrazone: A uricosuric drug that is used to reduce the serum urate levels in gout therapy. It lacks anti-inflammatory, analgesic, and diuretic properties.	3.1	1	0	pyrazolidines; sulfoxide	uricosuric drug
sulfobromophthalein Sulfobromophthalein: A phenolphthalein that is used as a diagnostic aid in hepatic function determination.	2.07	1	0	2-benzofurans; organobromine compound; organosulfonic acid; phenols	dye
suprofen Suprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic.. suprofen : An aromatic ketone that is thiophene substituted at C-2 by a 4-(1-carboxyethyl)benzoyl group.	3.1	1	0	aromatic ketone; monocarboxylic acid; thiophenes	antirheumatic drug; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
temazepam Temazepam: A benzodiazepine that acts as a GAMMA-AMINOBUTYRIC ACID modulator and anti-anxiety agent.	3.1	1	0	benzodiazepine
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.	6.19	5	2	diarylmethane
tetraethylammonium Tetraethylammonium: A potassium-selective ion channel blocker. (From J Gen Phys 1994;104(1):173-90)	3.57	2	0	quaternary ammonium ion
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.	2.46	2	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.	2.07	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
thiotepa Thiotepa: A very toxic alkylating antineoplastic agent also used as an insect sterilant. It causes skin, gastrointestinal, CNS, and bone marrow damage. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), thiotepa may reasonably be anticipated to be a carcinogen (Merck Index, 11th ed).	2.07	1	0	aziridines
thiram Thiram: A dithiocarbamate chemical, used commercially in the rubber processing industry and as a fungicide. In vivo studies indicate that it inactivates the enzyme GLUTATHIONE REDUCTASE. It has mutagenic activity and may induce chromosomal aberrations.. thiram : An organic disulfide that results from the formal oxidative dimerisation of N,N-dimethyldithiocarbamic acid. It is widely used as a fungicidal seed treatment.	7.25	1	0	organic disulfide	antibacterial drug; antifungal agrochemical; antiseptic drug
thonzylamine thonzylamine: major descriptor (72-84); file-maintained to PYRIMIDINES	3.1	1	0	methoxybenzenes
tiaprofenic acid tiaprofenic acid: RN given refers to parent cpd; structure. tiaprofenic acid : An aromatic ketone that is thiophene substituted at C-2 by benzoyl and at C-4 by a 1-carboxyethyl group.	3.1	1	0	aromatic ketone; monocarboxylic acid; thiophenes	drug allergen; non-steroidal anti-inflammatory drug
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.	2.48	2	0	monochlorobenzenes; thienopyridine	anticoagulant; fibrin modulating drug; hematologic agent; P2Y12 receptor antagonist; platelet aggregation inhibitor
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.	2.45	2	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
triacetin Triacetin: A triglyceride that is used as an antifungal agent.. triacetin : A triglyceride obtained by acetylation of the three hydroxy groups of glycerol. It has fungistatic properties (based on release of acetic acid) and has been used in the topical treatment of minor dermatophyte infections.	2.25	1	0	triglyceride	adjuvant; antifungal drug; food additive carrier; food emulsifier; food humectant; fuel additive; plant metabolite; solvent
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.	2.07	1	0	triazolobenzodiazepine	sedative
trientine Trientine: An ethylenediamine derivative used as stabilizer for EPOXY RESINS, as ampholyte for ISOELECTRIC FOCUSING and as chelating agent for copper in HEPATOLENTICULAR DEGENERATION.. TETA : An azamacrocyle in which four nitrogen atoms at positions 1, 4, 8 and 11 of a fouteen-membered ring are each substituted with a carboxymethyl group.. 2,2,2-tetramine : A polyazaalkane that is decane in which the carbon atoms at positions 1, 4, 7 and 10 are replaced by nitrogens.	2.31	1	0	polyazaalkane; tetramine	copper chelator
trifluoperazine [no description available]	3.1	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
triflupromazine Triflupromazine: A phenothiazine used as an antipsychotic agent and as an antiemetic.. triflupromazine : A member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position.	3.1	1	0	organofluorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; first generation antipsychotic
trigonelline trigonelline: in hydra among other organisms; RN given refers to hydroxide inner salt; structure. N-methylnicotinic acid : A pyridinium ion consisting of nicotinic acid having a methyl substituent on the pyridine nitrogen.. N-methylnicotinate : An iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group.	2.25	1	0	alkaloid; iminium betaine	food component; human urinary metabolite; plant metabolite
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.	2.07	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
tripelennamine Tripelennamine: A histamine H1 antagonist with low sedative action but frequent gastrointestinal irritation. It is used to treat ASTHMA; HAY FEVER; URTICARIA; and RHINITIS; and also in veterinary applications. Tripelennamine is administered by various routes, including topically.	3.1	1	0	aromatic amine
delavirdine Delavirdine: A potent, non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1.. delavirdine : The amide resulting from the formal condensation of 5-[(methylsulfonyl)amino]-1H-indole-2-carboxylic acid and 4-amino group of 1-[3-(isopropylamino)pyridin-2-yl]piperazine, delavirdine is a non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. Viral resistance emerges rapidly when delavirdine is used alone, so it is therefore used (as the methanesulfonic acid salt) with other antiretrovirals for combination therapy of HIV infection.	3.15	1	0	aminopyridine; indolecarboxamide; N-acylpiperazine; sulfonamide	antiviral drug; HIV-1 reverse transcriptase inhibitor
zomepirac zomepirac: RN given refers to parent cpd; structure	3.1	1	0	aromatic ketone; monocarboxylic acid; monochlorobenzenes; pyrroles	cardiovascular drug; non-steroidal anti-inflammatory drug
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.	7.52	2	0	mitomycin	alkylating agent; antineoplastic agent
corticosterone [no description available]	3.54	2	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
prednisolone Prednisolone: A glucocorticoid with the general properties of the corticosteroids. It is the drug of choice for all conditions in which routine systemic corticosteroid therapy is indicated, except adrenal deficiency states.. prednisolone : A glucocorticoid that is prednisone in which the oxo group at position 11 has been reduced to the corresponding beta-hydroxy group. It is a drug metabolite of prednisone.	2.46	2	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; drug metabolite; environmental contaminant; immunosuppressive agent; xenobiotic
estriol hormonin: estrogen replacement; each tablet contains 600 ug micronized 17beta-estradiol, 270 ug estriol and 1.4 mg estrone. chlorapatite : A phosphate mineral with the formula Ca5(PO4)3Cl.	3.1	1	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-hydroxy steroid	estrogen; human metabolite; human xenobiotic 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.	2.48	2	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
thymidine [no description available]	2.04	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
2-aminophenol [no description available]	3.1	1	0	aminophenol	bacterial metabolite
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	2.13	1	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
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.	3.84	3	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.	1.98	1	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
spironolactone Spironolactone: A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827). spironolactone : A steroid lactone that is 17alpha-pregn-4-ene-21,17-carbolactone substituted by an oxo group at position 3 and an alpha-acetylsulfanyl group at position 7.	2.07	1	0	3-oxo-Delta(4) steroid; oxaspiro compound; steroid lactone; thioester	aldosterone antagonist; antihypertensive agent; diuretic; environmental contaminant; xenobiotic
aldosterone [no description available]	3.53	2	0	11beta-hydroxy steroid; 18-oxo steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; mineralocorticoid; primary alpha-hydroxy ketone; steroid aldehyde	human metabolite; mouse metabolite
tetrahydrocortisol [no description available]	3.1	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3alpha-hydroxy steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone
prednisone Prednisone: A synthetic anti-inflammatory glucocorticoid derived from CORTISONE. It is biologically inert and converted to PREDNISOLONE in the liver.. prednisone : A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a beta-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid.	3.1	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; immunosuppressive agent; prodrug
tetrahydrocortisone [no description available]	3.1	1	0	21-hydroxy steroid
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	4.58	4	0	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
androsterone [no description available]	3.1	1	0	17-oxo steroid; 3alpha-hydroxy steroid; androstanoid; C19-steroid	androgen; anticonvulsant; human blood serum metabolite; human metabolite; human urinary metabolite; mouse metabolite; pheromone
etiocholanolone Etiocholanolone: The 5-beta-reduced isomer of ANDROSTERONE. Etiocholanolone is a major metabolite of TESTOSTERONE and ANDROSTENEDIONE in many mammalian species including humans. It is excreted in the URINE.. 3alpha-hydroxy-5beta-androstan-17-one : An androstanoid that is 5beta-androstane substituted by an alpha-hydroxy group at position 3 and an oxo group at position 17. It is a metabolite of testosterone in mammals.	3.1	1	0	17-oxo steroid; 3alpha-hydroxy steroid; androstanoid	human metabolite; mouse metabolite
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	3.1	1	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
hydroxyacetylaminofluorene Hydroxyacetylaminofluorene: A N-hydroxylated derivative of 2-ACETYLAMINOFLUORENE that has demonstrated carcinogenic action.	3.1	1	0	2-acetamidofluorenes
2-acetylaminofluorene 2-Acetylaminofluorene: A hepatic carcinogen whose mechanism of activation involves N-hydroxylation to the aryl hydroxamic acid followed by enzymatic sulfonation to sulfoxyfluorenylacetamide. It is used to study the carcinogenicity and mutagenicity of aromatic amines.	2	1	0	2-acetamidofluorenes	antimitotic; carcinogenic agent; epitope; mutagen
penicillin g Penicillin G: A penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on GAMMA-AMINOBUTYRIC ACID mediated synaptic transmission.. benzylpenicillin : A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido group.	2.07	1	0	penicillin allergen; penicillin	antibacterial drug; drug allergen; epitope
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
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.	2.83	3	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.	3.1	1	0	2-halophenol; amino acid zwitterion; iodophenol; iodothyronine	human metabolite; mouse metabolite; thyroid hormone
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.	2.63	2	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
benz(a)anthracene benz(a)anthracene: 4 fused rings of which one is angular in contrast to the linear NAPHTHACENES. tetraphene : An angular ortho-fused polycyclic arene consisting of four fused benzene rings.	3.1	1	0	ortho-fused polycyclic arene; tetraphenes
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	3.1	1	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	1.98	1	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
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.	2.25	1	0	alkenyl isothiocyanate; isothiocyanate	antimicrobial agent; antineoplastic agent; apoptosis inducer; lachrymator; metabolite
vincristine [no description available]	2.07	1	0	acetate ester; formamides; methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; tertiary alcohol; tertiary amino compound; vinca alkaloid	antineoplastic agent; drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
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.	3.41	6	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
ethinyl estradiol Ethinyl Estradiol: A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.. 17alpha-ethynylestradiol : A 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration.	3.1	1	0	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
uridine [no description available]	2.25	1	0	uridines	drug metabolite; 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.	2.5	2	0	kanamycins	bacterial metabolite
galactose galactopyranose : The pyranose form of galactose.	8.63	2	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	2.21	1	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
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]	3.66	9	0	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	antioxidant; plant metabolite
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	7.6	1	0	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
papaverine hydrochloride [no description available]	2.07	1	0
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	7.49	2	0	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
aniline [no description available]	3.1	1	0	anilines; primary arylamine
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.	2.17	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
desoxycorticosterone Desoxycorticosterone: A steroid metabolite that is the 11-deoxy derivative of CORTICOSTERONE and the 21-hydroxy derivative of PROGESTERONE	3.1	1	0	20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; mineralocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse 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.	7.98	4	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.	2.07	1	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
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
norethindrone Norethindrone: A synthetic progestational hormone with actions similar to those of PROGESTERONE but functioning as a more potent inhibitor of ovulation. It has weak estrogenic and androgenic properties. The hormone has been used in treating amenorrhea, functional uterine bleeding, endometriosis, and for CONTRACEPTION.. norethisterone : A 17beta-hydroxy steroid that is testosterone in which the hydrogen at position 17 is replaced by an ethynyl group and in which the methyl group attached to position 10 is replaced by hydrogen.	3.1	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound; tertiary alcohol	progestin; synthetic oral contraceptive
norethynodrel Norethynodrel: A synthetic progestational hormone with actions and uses similar to those of PROGESTERONE. It has been used in the treatment of functional uterine bleeding and ENDOMETRIOSIS. As a contraceptive (CONTRACEPTIVE AGENTS), it has usually been administered in combination with MESTRANOL.	3.1	1	0	oxo steroid
17-alpha-hydroxyprogesterone 17alpha-hydroxyprogesterone : A 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone.	3.1	1	0	17alpha-hydroxy-C21-steroid; 17alpha-hydroxy steroid; tertiary alpha-hydroxy ketone	human metabolite; metabolite; mouse metabolite; progestin
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
ampicillin Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.	3.1	1	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
cytarabine [no description available]	2.02	1	0	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
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.	3.57	2	0	organic sodium salt	dye
alizarin [no description available]	3.1	1	0	dihydroxyanthraquinone	chromophore; dye; plant 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.	2.11	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
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	2.5	2	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2.41	2	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	2.13	1	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
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
ethyl citrate ethyl citrate: structure	2.25	1	0	carbonyl compound
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	2.11	1	0
linalool linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.	3.1	1	0	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component
acrylamide [no description available]	7.6	1	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
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.	2.66	2	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
taurocholic acid Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	3.57	2	0	amino sulfonic acid; bile acid taurine conjugate	human metabolite
1,4-dihydroxyanthraquinone 1,4-dihydroxyanthraquinone: structure given in first source. quinizarin : A dihydroxyanthraquinone having the two hydroxy substituents at the 1- and 4-positions; formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxy groups	3.1	1	0	dihydroxyanthraquinone	dye
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
cyclizine Cyclizine: A histamine H1 antagonist given by mouth or parenterally for the control of postoperative and drug-induced vomiting and in motion sickness. (From Martindale, The Extra Pharmacopoeia, 30th ed, p935). cyclizine : An N-alkylpiperazine in which one nitrogen of the piperazine ring is substituted by a methyl group, while the other is substituted by a diphenylmethyl group.	3.1	1	0	N-alkylpiperazine	antiemetic; central nervous system depressant; cholinergic antagonist; H1-receptor antagonist; local anaesthetic
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.	7.53	2	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
2,6-dihydroxyanthraquinone 2,6-dihydroxyanthraquinone: structure given in first source. anthraflavic acid : A dihydroxyanthraquinone that is anthracene substituted by hydroxy groups at C-3 and C-7 and oxo groups at C-9 and C-10.	3.1	1	0	dihydroxyanthraquinone	antimutagen; plant metabolite
9,10-anthraquinone 9,10-anthraquinone : An anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.	3.1	1	0	anthraquinone
gramine gramine : An aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3.	2.07	1	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	2.25	1	0	pyrrolidin-2-ones
picryl chloride Picryl Chloride: A hapten that generates suppressor cells capable of down-regulating the efferent phase of trinitrophenol-specific contact hypersensitivity. (Arthritis Rheum 1991 Feb;34(2):180).. 1-chloro-2,4,6-trinitrobenzene : The C-nitro compound that is chlorobenzene with three nitro substituents in the 2-, 4- and 6-positions.	2.44	2	0	C-nitro compound; monochlorobenzenes	allergen; epitope; explosive; hapten
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.	8.52	2	0	monoterpenoid; phenols	volatile oil component
1-naphthol 1-naphthol: RN given refers to parent cpd. 1-naphthol : A naphthol carrying a hydroxy group at position 1.. hydroxynaphthalene : Any member of the class of naphthalenes that is naphthalene carrying one or more hydroxy groups.	3.1	1	0	naphthol	genotoxin; human xenobiotic metabolite
2-aminodiphenyl aminobiphenyl : Any member of the class of biphenyls in which the biphenyl skeleton is substituted by at least one amino group.	3.1	1	0
2-phenylphenol 2-phenylphenol: RN given refers to parent cpd; structure. biphenyl-2-ol : A member of the class of hydroxybiphenyls that is biphenyl substituted by a hydroxy group at position 2. It is generally used as a post-harvest fungicide for citrus fruits.	3.1	1	0	hydroxybiphenyls	antifungal agrochemical; environmental food contaminant
quinoline [no description available]	3.1	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
2-naphthylamine 2-Naphthylamine: A naphthalene derivative with carcinogenic action.. 2-naphthylamine : A naphthylamine carrying the amino group at position 2.	3.1	1	0	naphthylamine	carcinogenic agent
4-biphenylamine 4-biphenylamine: used in detection of sulfates, & as a carcinogen in cancer research; RN given refers to parent cpd; structure. biphenyl-4-amine : An aminobiphenyl that is biphenyl substituted by an amino group at position 4.	3.1	1	0	aminobiphenyl	carcinogenic agent
4-phenylphenol 4-phenylphenol: RN given refers to cpd without isomeric designation. biphenyl-4-ol : A member of the class of hydroxybiphenyls that is biphenyl carrying a hydroxy group at position 4.	3.1	1	0	hydroxybiphenyls
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.07	1	0	xanthene
benzidine benzidine: RN given refers to parent cpd. benzidine : A member of the class of biphenyls that is 1,1'-biphenyl in which the hydrogen at the para-position of each phenyl group has been replaced by an amino group.	3.1	1	0	biphenyls; substituted aniline	carcinogenic agent
4,4'-dihydroxybiphenyl biphenyl-4,4'-diol : A member of the class of hydroxybiphenyls that is biphenyl with hydroxy groups at positions 4 and 4'.	3.1	1	0	hydroxybiphenyls
synephrine [no description available]	5.95	9	1	ethanolamines; phenethylamine alkaloid; phenols	alpha-adrenergic agonist; plant metabolite
propylparaben Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)	3.1	1	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
butylphen butylphen: irritant; structure. 4-tert-butylphenol : A member of the class of phenols that is phenol substituted with a tert-butyl group at position 4.	3.1	1	0	phenols	allergen
methylparaben methylparaben: used as a preservative in cosmetics but potentiates UV-induced damage of skin; RN given refers to parent cpd. methylparaben : A 4-hydroxybenzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with methanol. It is the most frequently used antimicrobial preservative in cosmetics. It occurs naturally in several fruits, particularly in blueberries.	3.1	1	0	paraben	antifungal agent; antimicrobial food preservative; neuroprotective agent; plant metabolite
4-isopropylphenol [no description available]	3.1	1	0	phenols	flavouring agent
4-hydroxyacetophenone 4-hydroxyacetophenone: promotes secretion of bile & bile salts, which promotes griseofulvin absorption in the duodenum. 4'-hydroxyacetophenone : A monohydroxyacetophenone carrying a hydroxy substituent at position 4'.	3.1	1	0	monohydroxyacetophenone	fungal metabolite; mouse metabolite; plant metabolite
4-benzylphenol 4-benzylphenol: metabolite of diphenylmethane; RN given refers to parent cpd	3.1	1	0
xi-gamma-Undecalactone [no description available]	2.25	1	0	lactone
2-ethylhexanol [no description available]	3.56	2	0	primary alcohol	plant metabolite; volatile oil component
ethyl caprylate ethyl octanoate : A fatty acid ethyl ester resulting from the formal condensation of octanoic acid with ethanol.	2.25	1	0	fatty acid ethyl ester; octanoate ester	metabolite
ethyl laurate ethyl laurate : A fatty acid ethyl ester of lauric acid.	2.25	1	0	fatty acid ethyl ester	metabolite
acrolein [no description available]	7.58	2	0	enal	herbicide; human xenobiotic metabolite; toxin
glyoxal [no description available]	7.58	2	0	dialdehyde	agrochemical; allergen; pesticide; plant growth regulator
isopropyl acetate isopropyl acetate: cholesterol gallstone solvent	2.25	1	0
succinic anhydride [no description available]	2.31	1	0	cyclic dicarboxylic anhydride; tetrahydrofurandione
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.	2.07	1	0	pyrrole; secondary amine
ethyl decanoate ethyl decanoate : A fatty acid ethyl ester of decanoic acid.	2.25	1	0	decanoate ester; fatty acid ethyl ester	metabolite
methyl octanoate methyl octanoate : A fatty acid methyl ester resulting from the formal condensation of the carboxy group of octanoic acid with the hydroxy group of methanol.	2.25	1	0	fatty acid methyl ester; octanoate ester	metabolite
undecan-2-one undecan-2-one: Insect Repellents; 2-undecanone is the active ingredient of arthropod repellent BioUD; an efficacious alternative to deet. undecan-2-one : A dialkyl ketone with methyl and nonyl as the two alkyl groups.	2.25	1	0	dialkyl ketone; methyl ketone	plant metabolite; rodenticide
octyl acetate octyl acetate : The acetate ester of octan-1-ol.	2.25	1	0	acetate ester	plant metabolite
n-decyl alcohol n-decyl alcohol: RN given refers to parent cpd. decanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of ten carbon atoms.. decan-1-ol : A fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of ten carbon atoms.	2.25	1	0	decanol; primary alcohol	metabolite; pheromone; protic solvent
methyl palmitate [no description available]	2.25	1	0	fatty acid methyl ester	metabolite
undecan-1-ol undecan-1-ol : A primary alcohol that is undecane substituted by a hydroxy group at position 1.. undecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of eleven carbon atoms.	2.25	1	0	primary alcohol; undecanol	flavouring agent; plant metabolite
dodecanol Dodecanol: A saturated 12-carbon fatty alcohol obtained from coconut oil fatty acids. It has a floral odor and is used in detergents, lubricating oils, and pharmaceuticals. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). dodecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of twelve carbon atoms.. dodecan-1-ol : A primary alcohol that is dodecane in which a hydrogen from one of the methyl groups is replaced by a hydroxy group. It is registered for use in apple and pear orchards as a Lepidopteran pheromone/sex attractant, used to disrupt the mating behaviour of certain moths whose larvae destroy crops.	2.25	1	0	dodecanol; primary alcohol	bacterial metabolite; cosmetic; insect attractant; insecticide; pheromone; plant metabolite
eicosane icosane : A straight chain alkane composed of 20 carbon atoms. It has been isolated from the leaves of Agave attenuata.	7.6	1	0	long-chain alkane	plant metabolite
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.	2.07	1	0	biguanides	antineoplastic agent; geroprotector; hypoglycemic agent
2,2,2-trichloroethanol [no description available]	3.1	1	0	chloroethanol	mouse metabolite
anthrarufin 1,5-dihydroxyanthraquinone: used in ferric ion sensing as an inclusion complex with beta-cyclodextrin; structure in first source. anthrarufin : A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 5.	3.1	1	0	dihydroxyanthraquinone
2-ethylhexyl salicylate 2-ethylhexyl salicylate: structure given in first source	2.25	1	0	benzoate ester; phenols
2-toluic acid 2-toluic acid: RN given refers to parent cpd; structure. o-toluic acid : A methylbenzoic acid that is benzoic acid substituted by a methyl group at position 2.	3.1	1	0	methylbenzoic acid	xenobiotic metabolite
framycetin Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.	2.31	1	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
2,2'-methylenebis(4-methyl-6-tert-butylphenol) [no description available]	2.07	1	0	diarylmethane
ethyl-p-hydroxybenzoate ethyl-p-hydroxybenzoate: structure	3.1	1	0	ethyl ester; paraben	antifungal agent; antimicrobial food preservative; phytoestrogen; plant metabolite
3-tert-butyl-4-hydroxyanisole 3-tert-butyl-4-hydroxyanisole : An aromatic ether that is 4-methoxyphenol in which one of the hydrogens ortho- to the phenolic hydroxy group is replaced by a tert-butyl group.	3.1	1	0	aromatic ether; phenols	antioxidant; human xenobiotic metabolite
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.	2.48	2	0	anthrapyrazole; aromatic ketone; cyclic ketone	antineoplastic agent; c-Jun N-terminal kinase inhibitor; geroprotector
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
1-naphthylamine 1-Naphthylamine: A suspected industrial carcinogen (and listed as such by OSHA). Its N-hydroxy metabolite is strongly carcinogenic and mutagenic.. naphthylamine : A primary arylamine that is naphthalene substituted by an amino group at unspecified position.. 1-naphthylamine : A naphthylamine that is naphthalene substituted by an amino group at position 1.	3.1	1	0	naphthylamine	human xenobiotic metabolite
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	3.1	1	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
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.	3.53	2	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
nitrilotriacetic acid Nitrilotriacetic Acid: A derivative of acetic acid, N(CH2COOH)3. It is a complexing (sequestering) agent that forms stable complexes with Zn2+. (From Miall's Dictionary of Chemistry, 5th ed.)	2.46	2	0	NTA; tricarboxylic acid	carcinogenic agent; nephrotoxic agent
protocatechualdehyde protocatechualdehyde: found in wheat grains, wheat seedlings, & other plants; RN given refers to parent cpd; see also rancinamycins; structure	2.03	1	0	dihydroxybenzaldehyde
citronellol citronellol: alcohol form of citronellal; found in rose oil; RN given refers to parent cpd without isomeric designation; structure. citronellol : A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.. insect repellent : An insecticide that acts as a repellent to insects.	3.1	1	0	monoterpenoid	plant metabolite
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
hexanoic acid hexanoic acid : A C6, straight-chain saturated fatty acid.	3.1	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
pregnenolone [no description available]	3.1	1	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse 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.	1.98	1	0	methyl 17-hydroxy-20xi-yohimban-16-carboxylate	alpha-adrenergic antagonist; dopamine receptor D2 antagonist; serotonergic antagonist
diphenhydramine hydrochloride Antitussive Agents: Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.. diphenhydramine hydrochloride : The hydrochloride salt of diphenhydramine.	3.46	7	0	hydrochloride; organoammonium salt	anti-allergic agent; antiemetic; antiparkinson drug; antipruritic drug; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; sedative
ditiocarb Ditiocarb: A chelating agent that has been used to mobilize toxic metals from the tissues of humans and experimental animals. It is the main metabolite of DISULFIRAM.. diethyldithiocarbamic acid : A member of the class of dithiocarbamic acids that is diethylcarbamic acid in which both of the oxygens are replaced by sulfur.	3.1	1	0	dithiocarbamic acids	chelator; copper chelator
mequinol mequinol: depigmenting agent; RN given refers to parent cpd	3.1	1	0	methoxybenzenes; phenols	metabolite
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.	10.02	12	0	catechin	antioxidant; plant metabolite
phenetidine Phenetidine: Used in the manufacture of acetophenetidin.. 4-ethoxyaniline : An aromatic ether that is aniline in which the hydrogen at position 4 is replaced by an ethoxy group. It is a hydrolysis metabolite of phenacetin.	3.1	1	0	aromatic ether; primary amino compound; substituted aniline	drug metabolite
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	2.06	1	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
thiazoles [no description available]	2.44	2	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
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.	1.96	1	0	diazine; pyrazines	Daphnia magna metabolite
hydrazine diamine : Any polyamine that contains two amino groups.	2.44	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
aminoimidazole carboxamide Aminoimidazole Carboxamide: An imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. Compounded with orotic acid, it is used to treat liver diseases.. 5-aminoimidazole-4-carboxamide : An aminoimidazole in which the amino group is at C-5 with a carboxamido group at C-4.	2.71	3	0	aminoimidazole; monocarboxylic acid amide	mouse metabolite
perfluorobutyric acid perfluorobutyric acid: ion pairing reagent; RN given refers to parent cpd. perfluorobutyric acid : A monocarboxylic acid that is perfluorinated butyric acid.	2.03	1	0	fluoroalkanoic acid	chromatographic reagent; environmental contaminant; xenobiotic
4-hydroxyphenobarbital [no description available]	3.1	1	0	barbiturates
lithocholic acid Lithocholic Acid: A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic.. lithocholic acid : A monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.. lithocholate : A bile acid anion that is the conjugate base of lithocholic acid.	3.1	1	0	bile acid; C24-steroid; monohydroxy-5beta-cholanic acid	geroprotector; human metabolite; mouse metabolite
jervine jervine: teratogen from Veratrum grandiflorum; RN given refers to parent cpd(3beta,23beta)-isomer; structure	2.07	1	0	piperidines
glycyrrhetinic acid [no description available]	2.07	1	0	cyclic terpene ketone; hydroxy monocarboxylic acid; pentacyclic triterpenoid	immunomodulator; plant metabolite
chenodeoxycholic acid Chenodeoxycholic Acid: A bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.. chenodeoxycholic acid : A dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively.. chenodeoxycholate : Conjugate base of chenodeoxycholic acid; major species at pH 7.3.	3.1	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
glycocholic acid Glycocholic Acid: The glycine conjugate of CHOLIC ACID. It acts as a detergent to solubilize fats for absorption and is itself absorbed.. glycocholic acid : A bile acid glycine conjugate having cholic acid as the bile acid component.. glycocholate : A cholanic acid conjugate anion that is the conjugate base of glycocholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.07	1	0	bile acid glycine conjugate	human metabolite
boldine [no description available]	2.07	1	0	aporphine alkaloid
rhein [no description available]	3	4	0	dihydroxyanthraquinone
indirubin [no description available]	2.07	1	0
epitestosterone Epitestosterone: The 17-alpha isomer of TESTOSTERONE, derived from PREGNENOLONE via the delta5-steroid pathway, and via 5-androstene-3-beta,17-alpha-diol. Epitestosterone acts as an antiandrogen in various target tissues. The ratio between testosterone/epitestosterone is used to monitor anabolic drug abuse.. epitestosterone : An androstanoid that is the C-17 epimer of testosterone.	3.1	1	0	17alpha-hydroxy steroid; 3-oxo-Delta(4) steroid; androstanoid	androgen antagonist; human metabolite
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.	2.07	1	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.	2.07	1	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.	2.78	3	0	aromatic primary alcohol; dihydroxyanthraquinone	antineoplastic agent; plant metabolite
chrysophanic acid chrysophanic acid: RN given refers to parent cpd; structure in Merck, 9th ed, #2260. chrysophanol : A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity.	4.06	4	0	dihydroxyanthraquinone	anti-inflammatory agent; antiviral 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.	7.45	2	0	psoralens	EC 3.1.1.7 (acetylcholinesterase) inhibitor; metabolite
osthol osthol: from Cnidium monnieri and Angelica pubescens (both Apiaceae); structure given in first source	7.49	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
flavanone flavanone: RN given refers to cpd with unspecified isomeric designation; structure in first source. flavanone : The simplest member of the class of flavanones that consists of flavan bearing an oxo substituent at position 4.	3.16	5	0	flavanones
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.	7.78	3	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.	2.07	1	0	1,4-benzoquinones	adjuvant; anti-inflammatory agent; antidepressant; antineoplastic agent; antioxidant; cardioprotective agent; plant metabolite
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).	3.1	1	0	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
phloretic acid phloretic acid: structure. N-hydroxysuccinimide ester : An ester of N-hydroxysuccinimide.. phloretic acid : A hydroxy monocarboxylic acid consisting of propionic acid having a 4-hydroxyphenyl group at the 3-position.	2.11	1	0	hydroxy monocarboxylic acid	plant metabolite
thiazolidines Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.	2.08	1	0	thiazolidine
oleanolic acid [no description available]	3.31	6	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.	12.27	122	7	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
androstenediol Androstenediol: An intermediate in TESTOSTERONE biosynthesis, found in the TESTIS or the ADRENAL GLANDS. Androstenediol, derived from DEHYDROEPIANDROSTERONE by the reduction of the 17-keto group (17-HYDROXYSTEROID DEHYDROGENASES), is converted to TESTOSTERONE by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-HYDROXYSTEROID DEHYDROGENASES).. androst-5-ene-3beta,17beta-diol : A 3beta-hydroxy-Delta(5)-steroid that is 3beta-hydroxyandrost-5-ene carrying an additional hydroxy group at position 17beta.	3.1	1	0	17beta-hydroxy steroid; 3beta-hydroxy-Delta(5)-steroid	androgen; human metabolite; mouse metabolite; radiation protective agent
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.	3.1	1	0	17beta-hydroxy steroid; 17beta-hydroxyandrostan-3-one; 3-oxo-5alpha-steroid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
luminol Luminol: 5-Amino-2,3-dihydro-1,4-phthalazinedione. Substance that emits light on oxidation. It is used in chemical determinations.	2.74	3	0
flavone flavone: RN given refers to unlabeled cpd; structure given in first source. flavone : The simplest member of the class of flavones that consists of 4H-chromen-4-one bearing a phenyl substituent at position 2.	3.15	5	0	flavones	metabolite; nematicide
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	2.07	1	0	C-nitro compound; imidazoles	antitubercular agent
1,2,3,4-tetrahydro-1-naphthalenol 1,2,3,4-tetrahydro-1-naphthalenol: structure in first source	3.1	1	0
syringic acid syringic acid: RN given refers to parent cpd; structure in third source. syringic acid : A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid.	2.11	1	0	benzoic acids; dimethoxybenzene; phenols	plant metabolite
4-iodophenol [no description available]	3.1	1	0	iodophenol
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.	4.22	15	0	dialdehyde	biomarker
myristic acid Myristic Acid: A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). tetradecanoic acid : A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.. tetradecanoate : A long-chain fatty acid anion that is the conjugate base of myristic acid; major species at pH 7.3.	3.56	2	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite
paeonol paeonol: structure	2.04	1	0	methoxybenzenes; phenols	metabolite
4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol 4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol: structure in first source. 4-terpineol : A terpineol that is 1-menthene carrying a hydroxy substituent at position 4.	3.1	1	0	terpineol; tertiary alcohol	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiparasitic agent; apoptosis inducer; plant metabolite; volatile oil component
congo red Congo Red: An acid dye used in testing for hydrochloric acid in gastric contents. It is also used histologically to test for AMYLOIDOSIS.. Congo Red : An indicator dye that is blue-violet at pH 3.0 and red at pH 5.0.	2.25	1	0	bis(azo) compound
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	4.54	7	0	flavonols; monohydroxyflavone
6-hydroxyquinoline quinolin-6-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 6.	3.1	1	0	monohydroxyquinoline
3-hydroxybiphenyl 3-hydroxybiphenyl: structure given in first source. biphenyl-3-ol : A member of the class of hydroxybiphenyls that is phenol in which the hydrogen at position 3 has been replaced by a phenyl group.	3.1	1	0	hydroxybiphenyls
diphenylamine Diphenylamine: In humans it may be irritating to mucous membranes. Methemoglobinemia has been produced experimentally. In veterinary use, it is one of active ingredients in topical agents for prevention and treatment of screwworm infestation. An indicator in tests for nitrate poisoning.. diphenylamine : An aromatic amine containing two phenyl substituents. It has been used as a fungicide for the treatment of superficial scald in apples and pears, but is no longer approved for this purpose within the European Union.	3.1	1	0	aromatic amine; bridged diphenyl fungicide; secondary amino compound	antifungal agrochemical; antioxidant; carotogenesis inhibitor; EC 1.3.99.29 [phytoene desaturase (zeta-carotene-forming)] inhibitor; ferroptosis inhibitor; radical scavenger
2-tridecanone tridecan-2-one : A methyl ketone that is tridecane in which the methylene hydrogens at position 2 are replaced by an oxo group.	2.25	1	0	methyl ketone	flavouring agent; plant metabolite
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).	3.1	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.	2.1	1	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
4-ethylbenzoic acid [no description available]	2	1	0	benzoic acids
octacosane octacosane : A straight-chain alkane containing 28 carbon atoms.	7.6	1	0	long-chain alkane	plant metabolite
Berberine chloride (TN) [no description available]	3.57	2	0	organic molecular entity
glycochenodeoxycholic acid Glycochenodeoxycholic Acid: A bile salt formed in the liver from chenodeoxycholate and glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is a cholagogue and choleretic.. glycochenodeoxycholate : A N-acylglycinate that is the conjugate base of glycochenodeoxycholic acid.. glycochenodeoxycholic acid : A bile acid glycine conjugate having 3alpha,7alpha-dihydroxy-5beta-cholan-24-oyl as the bile acid component.	2.07	1	0	bile acid glycine conjugate	human metabolite
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.	2.07	1	0	cyclic ketone; erythromycin
4-propylphenol 4-propylphenol: structure given in first source	3.1	1	0	alkylbenzene
dehydroepiandrosterone sulfate Dehydroepiandrosterone Sulfate: The circulating form of a major C19 steroid produced primarily by the ADRENAL CORTEX. DHEA sulfate serves as a precursor for TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE.. dehydroepiandrosterone sulfate : A steroid sulfate that is the 3-sulfooxy derivative of dehydroepiandrosterone.	3.54	2	0	17-oxo steroid; steroid sulfate	EC 2.7.1.33 (pantothenate kinase) inhibitor; human metabolite; mouse metabolite
vinblastine [no description available]	3.57	2	0
hexafluoroisopropanol 1,1,1,3,3,3-hexafluoropropan-2-ol : An organofluorine compound formed by substitution of all the methyl protons in propan-2-ol by fluorine. It is a metabolite of inhalation anesthetic sevoflurane.	3.1	1	0	organofluorine compound; secondary alcohol	drug metabolite
1-methylpyridinium 1-methylpyridinium: RN given refers to parent cpd	3.57	2	0	methylpyridines
durapatite Durapatite: The mineral component of bones and teeth; it has been used therapeutically as a prosthetic aid and in the prevention and treatment of osteoporosis.. hydroxylapatite : A phosphate mineral with the formula Ca5(PO4)3(OH).	3.01	3	0
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	2.25	1	0	zinc molecular entity
glycyrrhizic acid glycyrrhizinic acid : A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.	9.68	8	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.	4.92	11	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
fenchol fenchol: RN given refers to cpd with unspecified isomeric designation	3.1	1	0
4-n-Butylphenol [no description available]	3.1	1	0	phenols
2-undecanol 2-undecanol: organic volatile isolated from nonpareil almonds, Prunus dulcis. undecan-2-ol : A secondary alcohol that is undecane substituted by a hydroxy group at position 2.	2.25	1	0	secondary alcohol; undecanol	animal metabolite; flavouring agent; pheromone; plant metabolite; volatile oil component
4-hydroxyazobenzene 4-hydroxyazobenzene: structure in first source	3.1	1	0
4-nitrothiophenolate 4-nitrothiophenolate: RN given refers to parent cpd	3.1	1	0
5 alpha-androstane-3 alpha,17 beta-diol 5alpha-androstane-3alpha,17beta-diol : The 5alpha-stereoisomer of androstane-3alpha,17beta-diol.	3.1	1	0	androstane-3alpha,17beta-diol	Daphnia magna metabolite; human metabolite
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.	7.08	1	0	organic cation	geroprotector; herbicide
amiloride Amiloride: A pyrazine compound inhibiting SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS. This inhibition creates a negative potential in the luminal membranes of principal cells, located in the distal convoluted tubule and collecting duct. Negative potential reduces secretion of potassium and hydrogen ions. Amiloride is used in conjunction with DIURETICS to spare POTASSIUM loss. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p705). amiloride : A member of the class of pyrazines resulting from the formal monoacylation of guanidine with the carboxy group of 3,5-diamino-6-chloropyrazine-2-carboxylic acid.	3.15	1	0	aromatic amine; guanidines; organochlorine compound; pyrazines	diuretic; sodium channel blocker
menthol (+-)-menthol : A racemate comprising equimolar amounts of (+)- and (-)-menthol. Both (+-)- and (-)-menthol are used to relieve symptoms of conditions such as bronchitis and sinusitis. When applied to the skin, menthol dilates the blood vessels, giving a sensation of coldness followed by an analgesic effect that relieves itching. It is therefore used in creams and ointments for the relief of pruritis and urticaria.. (-)-menthol : A p-menthan-3-ol which has (1R,2S,5R)-stereochemistry. It is the most common naturally occurring enantiomer.	3.1	1	0	p-menthan-3-ol	antipruritic drug; antispasmodic drug; antitussive
phenethyl isothiocyanate phenethyl isothiocyanate: a dietary liver aldehyde dehydrogenase inhibitor; promotes urinary bladder carcinoma. phenethyl isothiocyanate : An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.	2.07	1	0	isothiocyanate	antineoplastic agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; metabolite
muscarine [no description available]	2.07	1	0
acadesine [no description available]	2.01	1	0	1-ribosylimidazolecarboxamide; aminoimidazole; nucleoside analogue	antineoplastic agent; platelet aggregation inhibitor
hydroxyphenytoin hydroxyphenytoin: main metabolite of diphenylhydantoin; reduces Na(+) inhibition at high Na:K ratios; RN given refers to cpd without isomeric designation; structure. 4-hydroxyphenytoin : A imidazolidine-2,4-dione that consists of hydantoin bearing phenyl and 4-hydroxyphenyl substituents at position 5.	3.1	1	0	imidazolidine-2,4-dione; phenols	metabolite
stavudine Stavudine: A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.. stavudine : A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase	2.11	1	0	dihydrofuran; nucleoside analogue; organic molecular entity	antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
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
denatonium benzoate [no description available]	2.96	4	0
mono-(2-ethylhexyl)phthalate mono-(2-ethylhexyl)phthalate: RN given refers to parent cpd. mono(2-ethylhexyl) phthalate : The mono(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	3.1	1	0	phthalic acid monoester
1-naphthalenemethanol 1-naphthalenemethanol: structure given in first source. (1-naphthyl)methanol : A naphthylmethanol that is methanol in which one of the hydrogens of the methyl group is replaced by a naphthalen-1-yl group.	3.1	1	0	naphthylmethanol	mouse metabolite
trimetazidine Trimetazidine: A vasodilator used in angina of effort or ischemic heart disease.	3.17	4	0	aromatic amine
dexpropranolol [no description available]	3.1	1	0	propranolol
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.	7.58	2	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
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.17	1	0	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	7.6	1	0	elemental platinum; nickel group element atom; platinum group metal atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	2.59	2	0	copper group element atom; elemental silver	Escherichia coli metabolite
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	3.57	7	0	titanium group element atom
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.	7.07	1	0	cadmium molecular entity; zinc group element atom
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.	3.47	1	1	aluminium coordination entity	Lewis acid
zalcitabine Zalcitabine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.. zalcitabine : A pyrimidine 2',3'-dideoxyribonucleoside compound having cytosine as the nucleobase.	3.15	1	0	pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
mercuric chloride Mercuric Chloride: Mercury chloride (HgCl2). A highly toxic compound that volatizes slightly at ordinary temperature and appreciably at 100 degrees C. It is corrosive to mucous membranes and used as a topical antiseptic and disinfectant.. mercury dichloride : A mercury coordination entity made up of linear triatomic molecules in which a mercury atom is bonded to two chlorines. Water-soluble, it is highly toxic. Once used in a wide variety of applications, including preserving wood and anatomical specimens, embalming and disinfecting, as an intensifier in photography, as a mordant for rabbit and beaver furs, and freeing gold from lead, its use has markedly declined as less toxic alternatives have been developed.	2.1	1	0	mercury coordination entity	sensitiser
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	2	1	0	D-galactosamine; primary amino compound	toxin
hypochlorous acid Hypochlorous Acid: An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent.. hypochlorous acid : A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.	2.41	1	0	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human metabolite
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.95	4	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
sodium sulfate [no description available]	7.17	1	0	inorganic sodium salt
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	7.21	1	0	dihydrogen
nickel sulfate nickel sulfate: RN given refers to cpd with MF of Ni(2+)-H2SO4. nickel sulfate : A metal sulfate having nickel(2+) as the metal ion.	2.47	2	0	metal sulfate	allergen
butylated hydroxyanisole [no description available]	3.1	1	0
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	2.84	3	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
4-chloro-7-nitrobenzofurazan 4-Chloro-7-nitrobenzofurazan: A benzofuran derivative used as a protein reagent since the terminal N-NBD-protein conjugate possesses interesting fluorescence and spectral properties. It has also been used as a covalent inhibitor of both beef heart mitochondrial ATPase and bacterial ATPase.. 4-chloro-7-nitrobenzofurazan : A benzoxadiazole that is 2,1,3-benzoxadiazole which is substituted at position 4 by chlorine and at position 7 by a nitro group.	2.31	1	0	benzoxadiazole; C-nitro compound; organochlorine compound	EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.6.1.3 (adenosinetriphosphatase) inhibitor; fluorescent probe; fluorochrome
amopyroquine amopyroquine: RN given refers to parent cpd; structure	2.08	1	0
rhamnose [no description available]	3.75	10	0	L-rhamnose
ammonium chloride Ammonium Chloride: An acidifying agent that has expectorant and diuretic effects. Also used in etching and batteries and as a flux in electroplating.. ammonium chloride : An inorganic chloride having ammonium as the counterion.	7.15	1	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
3-hydroxybenzo(a)pyrene 3-hydroxybenzo(a)pyrene: RN given refers to unlabeled parent cpd	3.1	1	0	ortho- and peri-fused polycyclic arene
titanium dioxide titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.	2.17	1	0	titanium oxides	food colouring
4-n-Pentylphenol [no description available]	3.1	1	0	phenols
cephalexin Cephalexin: A semisynthetic cephalosporin antibiotic with antimicrobial activity similar to that of CEPHALORIDINE or CEPHALOTHIN, but somewhat less potent. It is effective against both gram-positive and gram-negative organisms.. cephalexin : A semisynthetic first-generation cephalosporin antibiotic having methyl and beta-(2R)-2-amino-2-phenylacetamido groups at the 3- and 7- of the cephem skeleton, respectively. It is effective against both Gram-negative and Gram-positive organisms, and is used for treatment of infections of the skin, respiratory tract and urinary tract.	3.15	1	0	beta-lactam antibiotic allergen; cephalosporin; semisynthetic derivative	antibacterial drug
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.	2.77	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
fluorides [no description available]	2.6	1	0	halide anion; monoatomic fluorine
9-hydroxybenzo(a)pyrene 9-hydroxybenzo(a)pyrene: RN given refers to unlabeled parent cpd	3.1	1	0	ortho- and peri-fused polycyclic arene
metergoline Metergoline: A dopamine agonist and serotonin antagonist. It has been used similarly to BROMOCRIPTINE as a dopamine agonist and also for MIGRAINE DISORDERS therapy.. metergoline : An ergoline alkaloid that is the N-benzyloxycarbonyl derivative of lysergamine. A 5-HT2 antagonist. Also 5-HT1 antagonist and 5-HT1D ligand. Has moderate affinity for 5-HT6 and high affinity for 5-HT7.	2.08	1	0	carbamate ester; ergoline alkaloid	dopamine agonist; geroprotector; serotonergic antagonist
keracyanin cyanidin 3-rutinoside: an anthocyanin compound. cyanidin 3-O-rutinoside chloride : A member of the class of anthocyanin chlorides that has cyanidin 3-O-rutinoside as the cationic counterpart.	2.5	2	0	anthocyanin chlorides
neohesperidin dihydrochalcone neohesperidin dihydrochalcone : A member of the dihydrochalcones that is 3,2',4',6'-tetrahydroxy-4-methoxydihydrochalcone attached to a neohesperidosyl residue at position 4' via glycosidic linkage. It is found in sweet orange.	2.25	1	0	dihydrochalcones; disaccharide derivative; neohesperidoside	environmental contaminant; plant metabolite; sweetening agent; xenobiotic
daunorubicin Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.	8.53	2	0	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
2-bromoergocryptine mesylate [no description available]	2.07	1	0	methanesulfonate salt	antiparkinson drug
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.	2.07	1	0	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.	4.34	4	1	benzenes; phenyl acetates
n-phenylethanolamine [no description available]	3.1	1	0	aralkylamine
4-ethylphenol 4-ethylphenol: RN given refers to parent cpd. 4-ethylphenol : A member of the class of phenols carrying an ethyl substituent at position 4.	3.1	1	0	phenols	fungal xenobiotic metabolite
ethyl nonanoate ethyl nonanoate : A fatty acid ethyl ester of nonanoic acid.	2.25	1	0	fatty acid ethyl ester	metabolite
ethyl myristate ethyl myristate : A long-chain fatty acid ethyl ester resulting from the formal condensation of the carboxy group of myristic acid with the hydroxy group of ethanol.	2.25	1	0	long-chain fatty acid ethyl ester
sucrose octaacetate sucrose octaacetate: bitter tasting cpd preferred by rats to quinine; RN given refers to ((beta-D)-fructofuranosyl)-isomer	2.05	1	0	glycoside
ursodeoxycholic acid Ursodeoxycholic Acid: An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.. ursodeoxycholic acid : A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.. ursodeoxycholate : A bile acid anion that is the conjugate base of ursodeoxycholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	3.1	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
pregnanolone Pregnanolone: A pregnane found in the urine of pregnant women and sows. It has anesthetic, hypnotic, and sedative properties.. 3alpha-hydroxy-5beta-pregnan-20-one : The 3alpha-stereoisomer of 3-hydroxy-5beta-pregnan-20-one.	3.1	1	0	3-hydroxy-5beta-pregnan-20-one; 3alpha-hydroxy steroid	human metabolite; intravenous anaesthetic; sedative
butylated hydroxytoluene 2,6-di-tert-butyl-4-methylphenol : A member of the class of phenols that is 4-methylphenol substituted by tert-butyl groups at positions 2 and 6.	3.1	1	0	phenols	antioxidant; ferroptosis inhibitor; food additive; geroprotector
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.	2.03	1	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
azoxymethane Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.	7.17	1	0
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	4.57	4	0	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
tobramycin Tobramycin: An aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius. It is effective against gram-negative bacteria, especially the PSEUDOMONAS species. It is a 10% component of the antibiotic complex, NEBRAMYCIN, produced by the same species.. tobramycin : A amino cyclitol glycoside that is kanamycin B lacking the 3-hydroxy substituent from the 2,6-diaminoglucose ring.	2.13	1	0	amino cyclitol glycoside	antibacterial agent; antimicrobial agent; toxin
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).	4.68	8	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
etoposide [no description available]	3.86	3	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
substance p [no description available]	2.08	1	0	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
6-hydroxybenzo(a)pyrene 6-hydroxybenzo(a)pyrene: RN given refers to parent cpd; structure in first source	3.1	1	0	ortho- and peri-fused polycyclic arene
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
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.	2.08	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.	7.45	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.	2.77	3	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.	2.5	2	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
dexibuprofen dexibuprofen: structure in first source	3.1	1	0	ibuprofen	non-narcotic analgesic; non-steroidal anti-inflammatory drug
benoxaprofen benoxaprofen: RN given refers to parent cpd; structure. benoxaprofen : A monocarboxylic acid that is propionic acid substituted at position 2 by a 2-(4-chlorophenyl)-1,3-benzoxazol-5-yl group. It was used as a non-steroidal anti-inflammatory drug until 1982 when it was withdrawn from the market due to adverse side-effects including liver necrosis, photosensitivity, and carcinogenicity in animals.	3.1	1	0	1,3-benzoxazoles; monocarboxylic acid; monochlorobenzenes	antipsoriatic; antipyretic; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; hepatotoxic agent; nephrotoxin; non-narcotic analgesic; non-steroidal anti-inflammatory drug; protein kinase C agonist
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
acarbose [no description available]	2.15	1	0	tetrasaccharide derivative	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; geroprotector; hypoglycemic agent
2-hydroxybenzo(a)pyrene 2-hydroxybenzo(a)pyrene: RN given refers to parent cpd; structure in first source	3.1	1	0	ortho- and peri-fused polycyclic arene
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.	2.49	2	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.	3.57	2	0	alkanethiol; L-proline derivative; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
4-(n-methyl-n-nitrosamino)-1-(3-pyridyl)-1-butanone 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone: structure; from tobacco smoke	2.03	1	0	nitrosamine; pyridines
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.	3.57	2	0	cephalosporin	antibacterial drug
cefaclor anhydrous Cefaclor: Semisynthetic, broad-spectrum antibiotic derivative of CEPHALEXIN.. cefaclor : A cephalosporin bearing chloro and (R)-2-amino-2-phenylacetamido groups at positions 3 and 7, respectively, of the cephem skeleton.	3.15	1	0	cephalosporin	antibacterial drug; drug allergen
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).	3.29	6	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	anticholesteremic drug; antineoplastic agent; Aspergillus metabolite; prodrug
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.	2.81	3	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
pravastatin Pravastatin: An antilipemic fungal metabolite isolated from cultures of Nocardia autotrophica. It acts as a competitive inhibitor of HMG CoA reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES).. pravastatin : A carboxylic ester resulting from the formal condensation of (S)-2-methylbutyric acid with the hydroxy group adjacent to the ring junction of (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6,8-dihydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid. Derived from microbial transformation of mevastatin, pravastatin is a reversible inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA). The sodium salt is used for lowering cholesterol and preventing cardiovascular disease. It is one of the lower potency statins, but has the advantage of fewer side effects compared with lovastatin and simvastatin.	9.09	4	0	3-hydroxy carboxylic acid; carbobicyclic compound; carboxylic ester; hydroxy monocarboxylic acid; secondary alcohol; statin (semi-synthetic)	anticholesteremic drug; environmental contaminant; metabolite; xenobiotic
atomoxetine atomoxetine : A secondary amino compound having methyl and 3-(2-methylphenoxy)-3-phenylpropan-1-yl substituents.	2.07	1	0	aromatic ether; secondary amino compound; toluenes	adrenergic uptake inhibitor; antidepressant; environmental contaminant; xenobiotic
mifepristone Mifepristone: A progestational and glucocorticoid hormone antagonist. Its inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua. As a glucocorticoid receptor antagonist, the drug has been used to treat hypercortisolism in patients with nonpituitary CUSHING SYNDROME.	2.07	1	0	3-oxo-Delta(4) steroid; acetylenic compound; tertiary amino compound	abortifacient; contraceptive drug; hormone antagonist; synthetic oral contraceptive
itraconazole Itraconazole: A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.. itraconazole : An N-arylpiperazine that is cis-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a p-[(+-)1-sec-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]phenyl group. A potent P-glycoprotein and CYP3A4 inhibitor, it is used as an antifungal drug for the treatment of various fungal infections, including aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, and sporotrichosis.	7.08	1	0	aromatic ether; conazole antifungal drug; cyclic ketal; dichlorobenzene; dioxolane; N-arylpiperazine; triazole antifungal drug; triazoles	EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; Hedgehog signaling pathway inhibitor; P450 inhibitor
ranolazine Ranolazine: An acetanilide and piperazine derivative that functions as a SODIUM CHANNEL BLOCKER and prevents the release of enzymes during MYOCARDIAL ISCHEMIA. It is used in the treatment of ANGINA PECTORIS.. N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide : An aromatic amide obtained by formal condensation of the carboxy group of 2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetic acid with the amino group of 2,6-dimethylaniline.. ranolazine : A racemate comprising equal amounts of (R)- and (S)-ranolazine. Used for treatment of chronic angina.	2.07	1	0	aromatic amide; monocarboxylic acid amide; monomethoxybenzene; N-alkylpiperazine; secondary alcohol
adefovir adefovir: inhibitor of African swine fever virus. adefovir(1-) : A organophosphonate oxoanion obtained by removal of a proton from the phosphonate group of adefovir, a nucleoside reverse transcriptase inhibitor. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).. adefovir : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.	3.15	1	0	6-aminopurines; ether; phosphonic acids	antiviral drug; DNA synthesis inhibitor; drug metabolite; HIV-1 reverse transcriptase inhibitor; nephrotoxic agent
clopidogrel Clopidogrel: A ticlopidine analog and platelet purinergic P2Y receptor antagonist that inhibits adenosine diphosphate-mediated PLATELET AGGREGATION. It is used to prevent THROMBOEMBOLISM in patients with ARTERIAL OCCLUSIVE DISEASES; MYOCARDIAL INFARCTION; STROKE; or ATRIAL FIBRILLATION.. clopidogrel : 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, the methylene hydrogen of which is replaced by a methoxycarbonyl group (the S enantiomer). A P2Y12 receptor antagonist, it is used to inhibit blood clots and prevent heart attacks.	2.07	1	0	methyl ester; monochlorobenzenes; thienopyridine	anticoagulant; P2Y12 receptor antagonist; platelet aggregation inhibitor
cidofovir anhydrous Cidofovir: An acyclic nucleoside phosphonate that acts as a competitive inhibitor of viral DNA polymerases. It is used in the treatment of RETINITIS caused by CYTOMEGALOVIRUS INFECTIONS and may also be useful for treating HERPESVIRUS INFECTIONS.. cidofovir anhydrous : Cytosine substituted at the 1 position by a 3-hydroxy-2-(phosphonomethoxy)propyl group (S configuration). A nucleoside analogue, it is an injectable antiviral used for the treatment of cytomegalovirus (CMV) retinitis in AIDS patients.	3.15	1	0	phosphonic acids; pyrimidone	anti-HIV agent; antineoplastic agent; antiviral drug; photosensitizing agent
topotecan Topotecan: An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA TOPOISOMERASES, TYPE I.. topotecan : A pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks.	3.57	2	0	pyranoindolizinoquinoline	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor
atorvastatin [no description available]	2.48	2	0	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic
lamivudine [no description available]	3.15	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
irinotecan [no description available]	4.07	4	0	carbamate ester; delta-lactone; N-acylpiperidine; pyranoindolizinoquinoline; ring assembly; tertiary alcohol; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 5.99.1.2 (DNA topoisomerase) 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.	3.57	2	0	biphenylyltetrazole; monocarboxylic acid amide; monocarboxylic acid	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
emtricitabine Emtricitabine: A deoxycytidine analog and REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B viruses. It is used to treat HIV INFECTIONS.. emtricitabine : An organofluorine compound that is 5-fluorocytosine substituted at the 1 position by a 2-(hydroxymethyl)-1,3-oxathiolan-5-yl group (2R,5S configuration). It is used in combination therapy for the treatment of HIV-1 infection.	3.57	2	0	monothioacetal; nucleoside analogue; organofluorine compound; pyrimidone	antiviral drug; HIV-1 reverse transcriptase inhibitor
octyl gallate [no description available]	3.1	1	0	gallate ester	food antioxidant; hypoglycemic agent; plant metabolite
pentadecan-2-one [no description available]	2.25	1	0	ketone
daunorubicin hydrochloride [no description available]	2.07	1	0	anthracycline
dehydrofelodipine dehydrofelodipine: the primary pyridine metabolite of felodipine	4.34	2	2	phenylpyridine
4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol [no description available]	3.1	1	0	stilbenoid
efavirenz efavirenz: HIV-1 reverse transcriptase inhibitor. efavirenz : 1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.	3.57	2	0	acetylenic compound; benzoxazine; cyclopropanes; organochlorine compound; organofluorine compound	antiviral drug; HIV-1 reverse transcriptase inhibitor
nelfinavir Nelfinavir: A potent HIV protease inhibitor. It is used in combination with other antiviral drugs in the treatment of HIV in both adults and children.. nelfinavir : An aryl sulfide that is used (as its mesylate salt) for treatment of HIV and also exhibits some anticancer properties.	2.07	1	0	aryl sulfide; benzamides; organic heterobicyclic compound; phenols; secondary alcohol; tertiary amino compound	antineoplastic agent; HIV protease inhibitor
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	4.75	28	0	D-glucopyranose	epitope; mouse metabolite
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
dihydrochalcone dihydrochalcone : A member of the class of dihydrochalcones that is acetophenone in which one of the hydrogens of the methyl group is replaced by a benzyl group.	7.51	2	0	dihydrochalcones	plant metabolite
2',7'-dichlorofluorescein 2',7'-dichlorofluorescein: RN given refers to parent cpd	3.1	1	0	2-benzofurans	fluorochrome
ursolic acid [no description available]	2.99	4	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
n-methylnicotinamide N-methylnicotinamide: structure. N-methylnicotinamide : A pyridinecarboxamide that is nicotinamide in which one of the amide hydrogens is substituted by a methyl group.	2.07	1	0	pyridinecarboxamide	metabolite
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.	2.07	1	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.	2.44	2	0	organic bromide salt	colorimetric reagent; dye
betulinic acid [no description available]	2.48	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
baicalin [no description available]	3.9	3	0	dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative	antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug
plerixafor plerixafor: a bicyclam derivate, highly potent & selective inhibitor of HIV-1 & HIV-2. plerixafor : An azamacrocycle consisting of two cyclam rings connected by a 1,4-phenylenebis(methylene) linker. It is a CXCR4 chemokine receptor antagonist and a hematopoietic stem cell mobilizer. It is used in combination with grulocyte-colony stimulating factor (G-CSF) to mobilize hematopoietic stem cells to the perpheral blood for collection and subsequent autologous transplantation in patients with non-Hodgkin's lymphoma and multiple myeloma.	2.17	1	0	azacycloalkane; azamacrocycle; benzenes; crown amine; secondary amino compound; tertiary amino compound	anti-HIV agent; antineoplastic agent; C-X-C chemokine receptor type 4 antagonist; immunological adjuvant
amprenavir [no description available]	2.07	1	0	carbamate ester; sulfonamide; tetrahydrofuryl ester	antiviral drug; HIV protease inhibitor
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.	4.55	7	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
aica ribonucleotide AICA ribonucleotide: purine precursor that has antineoplastic activity. AICA ribonucleotide : A 1-(phosphoribosyl)imidazolecarboxamide that is acadesine in which the hydroxy group at the 5' position has been converted to its monophosphate derivative.	2.42	2	0	1-(phosphoribosyl)imidazolecarboxamide; aminoimidazole	cardiovascular drug; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae 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.	2.11	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.	2.07	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
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
cephalosporin c cephalosporin C: RN given refers to parent cpd; structure in Merck, 9th ed, #1937. cephalosporin C : A cephalosporin antibiotic carrying a 3-acetoxymethyl substituent and a 6-oxo-N(6)-L-lysino group at position 7.	2.11	1	0	cephalosporin	fungal metabolite
16-hydroxytestosterone 16-hydroxytestosterone: RN given refers to (16alpha,17beta)-isomer. 16alpha-hydroxytestosterone : A C19-steroid that is testosterone in which the hydrogen at the 16alpha position has been replaced by a hydroxy group.	3.1	1	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; androstanoid; C19-steroid; diol; secondary alcohol	androgen
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
rutecarpine rutacarpine: from Evodia rutaecarpa; an ingredient in zhuyu hewei zhitong capsules	2.07	1	0	beta-carbolines
moguisteine [no description available]	2.08	1	0
repaglinide [no description available]	3.57	2	0	piperidines
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.	3.57	2	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
2-methoxyestradiol 2-methoxy-17beta-estradiol : A 17beta-hydroxy steroid, being 17beta-estradiol methoxylated at C-2.	3.1	1	0	17beta-hydroxy steroid; 3-hydroxy steroid	angiogenesis modulating agent; antimitotic; antineoplastic agent; human metabolite; metabolite; mouse metabolite
2-(n-cyclohexylamino)ethanesulfonic acid 2-(N-cyclohexylamino)ethanesulfonic acid: RN given refers to parent cpd. N-cyclohexyl-2-aminoethanesulfonic acid : An alkanesulfonic acid that is cyclohexanamine in which one of the amino hydrogens is substituted by a 2-sulfoethyl group. It is used as a buffer (pH range of 8.6-10.0) for studying pH-dependent processes in enzymology.	2.06	1	0	alkanesulfonic acid; secondary aliphatic amine	Good's buffer substance
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
tangeretin tangeretin: structure given in first source; from citrus plants; inhibits invasion of MO4 mouse cells into embryonic chick heart in vitro. tangeretin : A pentamethoxyflavone flavone with methoxy groups at positions 4', 5, 6 , 7 and 8.. pentamethoxyflavone : A methoxyflavone that is flavone substituted by a five methoxy groups.	5.73	15	0	pentamethoxyflavone	antineoplastic agent; plant metabolite
isoimperatorin isoimperatorin: tumor necrosis factor antagonist isolated from Glehniae root. isoimperatorin : A member of the class of psoralens that is psoralen substituted by a prenyloxy group at position 5. Isolated from Angelica dahurica and Angelica koreana, it acts as a acetylcholinesterase inhibitor.	7.03	1	0	psoralens	EC 3.1.1.7 (acetylcholinesterase) inhibitor; metabolite
5-hydroxyflavone [no description available]	2.05	1	0	flavones
5,6,7,8-tetrahydro-1-naphthol 5,6,7,8-tetrahydro-1-naphthol : 1-naphthol hydrogenated at C-5, -6, -7 and -8.	3.1	1	0	tetralins
alfatradiol alfatradiol: used for treating androgenetic alopecia. 17alpha-estradiol : An estradiol that is estra-1,3,5(10)-triene substituted by hydroxy groups at positions 3 and 17 (the 17alpha stereoisomer).	3.1	1	0	17alpha-hydroxy steroid; 3-hydroxy steroid; estradiol	estrogen; geroprotector
sertraline Sertraline: A selective serotonin uptake inhibitor that is used in the treatment of depression.. sertraline : A member of the class of tetralins that is tetralin which is substituted at positions 1 and 4 by a methylamino and a 3,4-dichlorophenyl group, respectively (the S,S diastereoisomer). A selective serotonin-reuptake inhibitor (SSRI), it is administered orally as the hydrochloride salt as an antidepressant for the treatment of depression, obsessive-compulsive disorder, panic disorder and post-traumatic stress disorder.	7.13	1	0	dichlorobenzene; secondary amino compound; tetralins	antidepressant; serotonin uptake inhibitor
talinolol [no description available]	5.75	7	1	ureas
4-hydroxyquinoline 4-quinolone : A quinolone that is 1,4-dihydroquinoline substituted by an oxo group at position 4.	3.1	1	0	monohydroxyquinoline; quinolone
malvidin chloride [no description available]	2.05	1	0
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
vinburnine [no description available]	2.07	1	0	alkaloid
uk 68798 [no description available]	2.07	1	0	aromatic ether; sulfonamide; tertiary amino compound	anti-arrhythmia drug; potassium channel blocker
bufuralol bufuralol: RN given refers to cpd without isomeric designation; structure	2.07	1	0	benzofurans
ubenimex ubenimex: growth inhibitor	3.57	2	0
epicatechin (-)-epicatechin : A catechin with (2R,3R)-configuration.	3.3	6	0	catechin; polyphenol	antioxidant
gallocatechol (-)-epigallocatechin : A flavan-3,3',4',5,5',7-hexol having (2R,3R)-configuration.	2.44	2	0	catechin; flavan-3,3',4',5,5',7-hexol	antioxidant; food component; plant metabolite
6-hydroxyflavone 6-hydroxyflavone: antioxidant; structure in first source	2.05	1	0	hydroxyflavonoid
hesperetin [no description available]	11.78	18	1	3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone	antineoplastic agent; antioxidant; plant metabolite
magnolol [no description available]	8.45	7	0	biphenyls
honokiol [no description available]	7.97	4	0	biphenyls
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
nobiletin nobiletin : A methoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 8, 3' and 4' respectively.	5.09	13	0	methoxyflavone	antineoplastic agent; plant metabolite
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
tetrandrine tetrandrine: a bisbenzylisoquinoline that exhibits antifibrogenic activity	2.07	1	0	bisbenzylisoquinoline alkaloid; isoquinolines
beta-amyrin beta-amyrin: alpha-amyrin is also available; a 5 ring triterpene derived from oleanane that differs from alpha-amyrin in having the 29-carbon at the 20 position; RN given refers to (3 beta)-isomer. beta-amyrin : A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants.	2.42	2	0	pentacyclic triterpenoid; secondary alcohol	Aspergillus metabolite; plant metabolite
(-)-catechin (-)-catechin : The (-)-enantiomer of catechin.	2.11	1	0	catechin	metabolite
alpha-amyrin alpha-amyrin: beta-amyrin is also available; a 5 ring triterpene derived from taraxasterol that differs from beta-amyrin in having the 29-carbon at the 19 position. alpha-amyrin : A pentacyclic triterpenoid that is ursane which contains a double bond between positions 12 and 13 and in which the hydrogen at the 3beta position is substituted by a hydroxy group.	2.07	1	0	pentacyclic triterpenoid; secondary alcohol
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	2.07	1	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
perfluorooctane sulfonic acid perfluorooctane-1-sulfonic acid : A perfluoroalkanesulfonic acid that is octane-1-sulfonic acid in which all seventeen of the hydrogens that are attached to carbons hvae been replaced by fluorines.	2.17	1	0	perfluoroalkanesulfonic acid	antilipemic drug; persistent organic pollutant
3-(3,4-dimethoxyphenyl)propanoic acid 3-(3,4-dimethoxyphenyl)propanoic acid : A monocarboxylic acid that is propanoic acid substituted by a 3,4-dimethoxyphenyl group at position 3.	2.11	1	0	dimethoxybenzene; monocarboxylic acid
4-hydroxyindole hydroxyindoles : Any member of the class of indoles carrying at least one hydroxy group.	2.07	1	0	hydroxyindoles; phenols
methyl alpha-d-galactopyranoside methyl-galactopyranoside: structure in first source. methyl alpha-D-galactoside : An alpha-D-galactoside having a methyl substituent at the anomeric position.	3.51	1	0	alpha-D-galactoside; methyl D-galactoside; monosaccharide derivative
2',7'-dichlorodihydrofluorescein diacetate [no description available]	2.1	1	0
eletriptan eletriptan: 5-HT(1B/1D) receptor agonist; structure in first source. eletriptan : An N-alkylpyrrolidine, that is N-methylpyrrolidine in which the pro-R hydrogen at position 2 is replaced by a {5-[2-(phenylsulfonyl)ethyl]-1H-indol-3-yl}methyl group.	2.07	1	0	indoles; N-alkylpyrrolidine; sulfone	non-steroidal anti-inflammatory drug; serotonergic agonist; vasoconstrictor agent
rosiglitazone [no description available]	2.07	1	0	aminopyridine; thiazolidinediones	EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; insulin-sensitizing drug
4-phenylbutylamine 4-phenylbutylamine: used as a drug partition into lipid bilayers in a cubic liquid-crystalline phase. 4-phenylbutylamine : A phenylalkylamine that is benzene in which one of the hydrogens is substituted by a 4-aminobutyl group.	2.6	1	0	benzenes; phenylalkylamine; primary amino compound
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.	5.31	4	1	3'-hydroxyflavanones; 4'-hydroxyflavanones; disaccharide derivative; flavanone glycoside; rutinoside; trihydroxyflavanone	antioxidant
hypobromous acid [no description available]	2.05	1	0	bromine oxoacid
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.	2.48	2	0	macrolide antibiotic	antibacterial drug; environmental contaminant; protein synthesis inhibitor; xenobiotic
bromates Bromates: Negative ions or salts derived from bromic acid, HBrO3.	2.05	1	0	bromine oxoanion; monovalent inorganic anion
7,8-dihydromethysticin [no description available]	2.07	1	0	2-pyranones; aromatic ether
gentiopicroside gentiopicroside: a secoiridoid in Gentiana with rearrangement to two pyran rings	2.07	1	0	glycoside
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.	2.79	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]	2.07	1	0	(8xi)-cinchonan-9-ol; cinchona alkaloid	metabolite
fibrinogen Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.	2.03	1	0	iditol	fungal metabolite
17-alpha-hydroxypregnenolone 17-alpha-Hydroxypregnenolone: A 21-carbon steroid that is converted from PREGNENOLONE by STEROID 17-ALPHA-HYDROXYLASE. It is an intermediate in the delta-5 pathway of biosynthesis of GONADAL STEROID HORMONES and the adrenal CORTICOSTEROIDS.. 17alpha-hydroxypregnenolone : A hydroxypregnenolone carrying an alpha-hydroxy group at position 17.	3.1	1	0	17alpha-hydroxy-C21-steroid; 17alpha-hydroxy steroid; 3beta-hydroxy-Delta(5)-steroid; hydroxypregnenolone; tertiary alpha-hydroxy ketone	human metabolite; mouse 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]	2.07	1	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.	2.94	4	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
5-(3-hydroxyphenyl)-5-phenylhydantoin 5-(3-hydroxyphenyl)-5-phenylhydantoin: metabolite of phenytoin; RN given refers to cpd without isomeric designation	3.1	1	0
deacetyldiltiazem deacetyldiltiazem: metabolite of diltiazem; RN given refers to (cis-(+-))-isomer	2.02	1	0	benzothiazepine
sarsasapogenin [no description available]	2.07	1	0	sapogenin
taraxerol taraxerol: structure. taraxerol : A pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15.	2.07	1	0	pentacyclic triterpenoid; secondary alcohol	metabolite
spathulenol [no description available]	2.07	1	0	carbotricyclic compound; olefinic compound; sesquiterpenoid; tertiary alcohol	anaesthetic; plant metabolite; vasodilator agent; volatile oil component
7-amino-4-methylcoumarin 7-amino-4-methylcoumarin: RN given refers to parent cpd	3.1	1	0	7-aminocoumarins	fluorochrome
zofenopril zofenopril: structure given in first source; SQ 26900 refers to K salt & SQ 26991 to Ca salt. zofenopril : A proline derivative that is 4-(phenylsulfanyl)-L-proline in which the amine proton is replaced by a (2S)-3-(benzoylsulfanyl)-2-methylpropanoyl group. A prodrug for zofenoprilat.	3.15	1	0	aryl sulfide; L-proline derivative; N-acyl-L-amino acid; thioester	anticonvulsant; apoptosis inhibitor; cardioprotective agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; prodrug; vasodilator agent
lopinavir [no description available]	8.9	3	0	amphetamines; dicarboxylic acid diamide	anticoronaviral agent; antiviral drug; HIV protease inhibitor
11-hydroxyprogesterone, (11alpha)-isomer 11alpha-hydroxyprogesterone : A 11alpha-hydroxy steroid that is pregn-4-ene-3,20-dione substituted by a hydroxy group at position 11.	3.1	1	0	11alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(4) steroid
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.	3.1	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.	2.93	4	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; flavanone 7-O-beta-D-glucoside; monosaccharide derivative	antibacterial agent; antilipemic drug; hypoglycemic agent; metabolite
3,5-diiodothyronine, (l)-isomer [no description available]	3.1	1	0	phenylalanine derivative
glycyl-l-phenylalanine glycylphenylalanine: RN given refers to (DL)-isomer. Gly-Phe : A dipeptide formed from glycine and L-phenylalanine residues.	2.04	1	0	dipeptide zwitterion; dipeptide	human metabolite; 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
glycylsarcosine glycylsarcosine : A dipeptide obtained by formal condensation of the carboxy group of glycine with the amino group of sarcosine.	3.15	1	0	dipeptide zwitterion; dipeptide
methyl beta-galactoside methyl beta-galactoside: RN given refers to (beta-D)-isomer. methyl galactoside : A methyl glycoside in which the H of the OH group on C-1 of galactose is replaced by a methyl group.. methyl beta-D-galactoside : A beta-D-galactopyranoside having a methyl substituent at the anomeric position.	3.51	1	0	beta-D-galactoside; methyl D-galactoside; monosaccharide derivative
harmol hydrochloride [no description available]	3.53	2	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
4',5,6,7-tetramethoxyflavone 4',5,6,7-tetramethoxyflavone: structure given in first source; from plant Eupatorium odoratum. 4',5,6,7-tetramethoxyflavone : A tetramethoxyflavone that is the tetra-O-methyl derivative of scutellarein.	2	1	0	tetramethoxyflavone	antimutagen; plant metabolite
10-hydroxycamptothecin [no description available]	2.07	1	0	pyranoindolizinoquinoline
diosgenin [no description available]	3.55	2	0	3beta-sterol; hexacyclic triterpenoid; sapogenin; spiroketal	antineoplastic agent; antiviral agent; apoptosis inducer; metabolite
sarsasapogenin, (3beta,5alpha,25r)-isomer tigogenin : A widely used steroidal sapogenin isolated from several plant species and used for synthesizing steroid drugs.	3.1	1	0	sapogenin	gout suppressant; plant metabolite
syringaresinol [no description available]	2.25	1	0	aromatic ether; furofuran; lignan; polyether; polyphenol	plant metabolite
corydaline [no description available]	2.07	1	0	isoquinoline alkaloid; isoquinolines
friedelinol friedelinol: isolated from seeds of Aster auriculatus Franch; structure given in first source; RN given refers to friedelanol (friedelinol), the (3alpha)-isomer	2	1	0
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.	2.07	1	0	(8xi)-cinchonan-9-ol; cinchona alkaloid	metabolite
3 alpha,17 alpha-dihydroxy-5 beta-pregnan-20-one 3alpha,17alpha-dihydroxy-5beta-pregnan-20-one : A 17alpha-hydroxy steroid that is 3alpha-hydroxy-5beta-pregnan-20-one carrying an additional hydroxy group at position 17alpha.	3.1	1	0	17alpha-hydroxy steroid; 20-oxo steroid; 3alpha-hydroxy steroid; C21-steroid; corticosteroid hormone	human urinary metabolite
methyl mannoside, (alpha-d)-isomer methylmannoside: RN given refers to (D)-isomer; see also record for 3-O-methylmannose. methyl alpha-D-mannoside : A methyl mannoside having alpha-configuration at the anomeric centre.	3.51	1	0	alpha-D-mannoside; methyl mannoside
2-methoxyestriol [no description available]	3.1	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.	2.21	1	0	cobalt group element atom; metal allergen	micronutrient
p-methoxy-n-methylphenethylamine p-Methoxy-N-methylphenethylamine: A potent mast cell degranulator. It is involved in histamine release.. N,O-dimethyltyramine : A secondary amino compound that is tyramine in which the hydrogen of the phenolic hydroxy group has been replaced by a methyl group.	1.95	1	0	aromatic ether; secondary amino compound	metabolite
fulvestrant Fulvestrant: An estradiol derivative and estrogen receptor antagonist that is used for the treatment of estrogen receptor-positive, locally advanced or metastatic breast cancer.. fulvestrant : A 3-hydroxy steroid that is 17beta-estradiol in which the 7alpha hydrogen has been replaced by a nonyl group in which one of the hydrogens of the terminal methyl has been replaced by a (4,4,5,5,5-pentafluoropentyl)sulfinyl group. An estrogen receptor antagonist, it is used in the treatment of breast cancer.	2.08	1	0	17beta-hydroxy steroid; 3-hydroxy steroid; organofluorine compound; sulfoxide	antineoplastic agent; estrogen antagonist; estrogen receptor antagonist
arginyl-glycyl-aspartic acid arginyl-glycyl-aspartic acid: amino acid sequence of basic unit of widespread cellular recognition system	2.41	1	0	oligopeptide
cp-55,940 [no description available]	3.15	1	0
2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine: directly acting genotoxic metabolite of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine. N-hydroxy-PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, hydoxyamino, and phenyl groups, respectively. The active metabolite of the dietary carcinogen PhIP.	3.1	1	0	hydroxylamine; imidazopyridine	carcinogenic agent; genotoxin; human xenobiotic metabolite; mouse metabolite; mutagen; neurotoxin; rat metabolite
norverapamil norverapamil: N-demethylated active metabolite of verapamil; RN given refers to parent cpd without isomeric designation; structure in second source. norverapamil : A racemate comprising equimolar amounts of (R)- and (S)-norverapamil. The major active metabolite of verapamil.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-2-(propan-2-yl)pentanenitrile : A secondary amino compound that is 3,4-dimethoxyphenylethylamine in which one of the hydrogens attached to the nitrogen has been replaced by a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	7.43	2	0	aromatic ether; nitrile; polyether; secondary amino compound
fluo-3 Fluo-3: fluorescent Ca(2+) indicator; permits continuous monitoring of Ca without interference with use of UV-sensitive caged compounds	2.48	2	0	xanthene dye	fluorochrome
propidium iodide [no description available]	2.07	1	0	organic iodide salt
saikosaponin d [no description available]	2.49	2	0
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	2.07	1	0	beta-carbolines
geniposide [no description available]	2.49	2	0	terpene glycoside
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.	2.52	2	0	proanthocyanidin
pisatin pisatin: phytoalexin produced in plants after injection with fungi; RN given refers to (6aS-cis)-isomer; structure	2.06	1	0
epicatechin gallate epicatechin gallate: a steroid 5alpha-reductase inhibitor; RN given refers to the (cis)-isomer; structure given in first source; isolated from green tea. (-)-epicatechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.	2.73	3	0	catechin; gallate ester; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
ecopipam ecopipam: structure given in first source	3.1	1	0	benzazepine
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).	2.76	3	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
proanthocyanidin proanthocyanidin: RN given refers to proanthocyanidin A; Cannabinoid Receptor CB1 antagonist. proanthocyanidin : A flavonoid oligomer obtained by the the condensation of two or more units of hydroxyflavans.	2.52	2	0
parthenolide [no description available]	2.07	1	0	germacranolide
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.	2.31	1	0
neoeriocitrin neoeriocitrin: protects against autophagy-inhibiting effects of okadaic acid; isolated from Drynariae rhizome; structure in first source. neoeriocitrin : A flavanone glycoside that is eriodictyol substituted by a 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage.	3.52	7	0	4'-hydroxyflavanones; disaccharide derivative; flavanone glycoside; neohesperidoside; trihydroxyflavanone	plant metabolite
homoorientin homoorientin: isolated from Swertia japonica; structure given in first source	2.07	1	0	flavone C-glycoside; tetrahydroxyflavone	antineoplastic agent; radical scavenger
liquiritigenin liquiritigenin: structure given in first source; isolated from Pterocarpus marsupium. 4',7-dihydroxyflavanone : A dihydroxyflavanone in which the two hydroxy substituents are located at positions 4' and 7.. liquiritigenin : A dihydroxyflavanone compound having the two hydroxy substituents at the 4'- and 7-positions. Isolated from the root of Glycyrrhizae uralensis, it is a selective agonist for oestrogen receptor beta.	2.74	3	0	4',7-dihydroxyflavanone	hormone agonist; plant metabolite
ibuprofen, (r)-isomer [no description available]	3.1	1	0	ibuprofen
11-hydroxytestosterone 11-hydroxytestosterone: RN given refers to (11 beta,17 beta)-isomer. 11beta-hydroxytestosterone : An androstanoid that is testosterone carrying an additional hydroxy substituent at the 11beta-position.	3.1	1	0	11beta-hydroxy steroid; 17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; androstanoid; C19-steroid	bacterial xenobiotic metabolite; human xenobiotic metabolite; marine metabolite
norbuprenorphine norbuprenorphine: metabolite of buprenorphine found in urine & feces; RN given refers to (5alpha,7alpha)-isomer; structure given in first source	3.1	1	0	phenanthrenes
3'-o-(4-benzoyl)benzoyladenosine 5'-triphosphate 3'-O-(4-benzoyl)benzoyladenosine 5'-triphosphate: purinergic receptors agonist; structure given in first source	2.13	1	0	purine ribonucleoside triphosphate
asiatic acid [no description available]	2.07	1	0	monocarboxylic acid; pentacyclic triterpenoid; triol	angiogenesis modulating agent; metabolite
obacunone obacunone: from bark of Chinese plant Phellodendron amurense; shortens sleeping time induced in mice by alpha-chloralose-urethane	1.99	1	0	limonoid
benzo(a)pyrene-3,6-quinol [no description available]	3.1	1	0
elacridar Elacridar: inhibitor of MDR1 PROTEIN; structure given in first source	2.47	2	0
pramipexole Pramipexole: A benzothiazole derivative and dopamine agonist with antioxidant properties that is used in the treatment of PARKINSON DISEASE and RESTLESS LEGS SYNDROME.. pramipexole : A member of the class of benzothiazoles that is 4,5,6,7-tetrahydro-1,3-benzothiazole in which the hydrogens at the 2 and 6-pro-S-positions are substituted by amino and propylamino groups, respectively.	3.15	1	0	benzothiazoles; diamine	antidyskinesia agent; antiparkinson drug; dopamine agonist; radical scavenger
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
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
tetradecanoylphorbol acetate [no description available]	2.07	1	0
celastrol [no description available]	2.07	1	0	monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory drug; antineoplastic agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Hsp90 inhibitor; metabolite
procyanidin b2 procyanidin B2 : A proanthocyanidin consisting of two molecules of (-)-epicatechin joined by a bond between positions 4 and 8' in a beta-configuration. Procyanidin B2 can be found in Cinchona pubescens (Chinchona, in the rind, bark and cortex), in Cinnamomum verum (Ceylon cinnamon, in the rind, bark and cortex), in Crataegus monogyna (Common hawthorn, in the flower and blossom), in Uncaria guianensis (Cat's claw, in the root), in Vitis vinifera (Common grape vine, in the leaf), in Litchi chinensis (litchi, in the pericarp), in the apple, in Ecdysanthera utilis and in red wine.	2.8	3	0	biflavonoid; hydroxyflavan; polyphenol; proanthocyanidin	antioxidant; 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
aromadedrin aromadedrin: inhibits protein kinase C; the dihydro makes it a flavone rather than a flavonol. (+)-dihydrokaempferol : A tetrahydroxyflavanone having hydroxy groupa at the 3-, 4'-, 5- and 7-positions.	2.05	1	0	4'-hydroxyflavanones; dihydroflavonols; secondary alpha-hydroxy ketone; tetrahydroxyflavanone	metabolite
peroxynitrous acid Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).	2.11	1	0	nitrogen oxoacid
imatinib mesylate imatinib methanesulfonate : A methanesulfonate (mesylate) salt that is the monomesylate salt of imatinib. Used for treatment of chronic myelogenous leukemia and gastrointestinal stromal tumours.	2.06	1	0	methanesulfonate salt	anticoronaviral agent; antineoplastic agent; apoptosis inducer; tyrosine kinase inhibitor
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
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
methotrexate [no description available]	4.14	4	0	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
delphinidin delphinidin: RN given refers to parent cpd;. delphinidin : An anthocyanidin cation consisting of benzopyrylium with hydroxy substituents at the 3-, 5- and 7-positions and a 3,4,5-trihydroxyphenyl group at the 2-position. It is a plant pigment responsible for the colours of the plants of the genera Viola and Delphinium.	2.05	1	0	5-hydroxyanthocyanidin	antineoplastic agent; biological pigment; plant metabolite
cyanidin cyanidin: RN given refers to parent cpd; structure. cyanidin cation : An anthocyanidin cation that is flavylium substituted at positions 3, 3', 4', 5 and 7 by hydroxy groups.	2.48	2	0	5-hydroxyanthocyanidin	antioxidant; metabolite; neuroprotective agent
olmesartan medoxomil Olmesartan Medoxomil: An ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKER that is used to manage HYPERTENSION.	2.07	1	0	biphenyls
kn 04 KN 04: structure given in first source	1.99	1	0
5-carboxyfluorescein diacetate [no description available]	2.07	1	0
carbapenems [no description available]	2.41	1	0
aspartame [no description available]	3.89	2	1	carboxylic acid; dipeptide zwitterion; dipeptide; methyl ester	apoptosis inhibitor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; environmental contaminant; micronutrient; nutraceutical; sweetening agent; xenobiotic
5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone: has antineoplastic activity; structure in first source	2	1	0	ether; flavonoids
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.	2.43	2	0	pentamethoxyflavone	plant metabolite
harmalol hydrochloride [no description available]	2.07	1	0
atazanavir atazanavir : A heavily substituted carbohydrazide that is an antiretroviral drug of the protease inhibitor (PI) class used to treat infection of human immunodeficiency virus (HIV).	2.07	1	0	carbohydrazide	antiviral drug; HIV protease inhibitor
tariquidar [no description available]	3.15	1	0	benzamides
levofloxacin Levofloxacin: The L-isomer of Ofloxacin.. levofloxacin : An optically active form of ofloxacin having (S)-configuration; an inhibitor of bacterial topoisomerase IV and DNA gyrase.	3.58	2	0	9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid; fluoroquinolone antibiotic; quinolone antibiotic	antibacterial drug; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; topoisomerase IV inhibitor
ezetimibe Ezetimibe: An azetidine derivative and ANTICHOLESTEREMIC AGENT that inhibits intestinal STEROL absorption. It is used to reduce total CHOLESTEROL; LDL CHOLESTEROL, and APOLIPOPROTEINS B in the treatment of HYPERLIPIDEMIAS.. ezetimibe : A beta-lactam that is azetidin-2-one which is substituted at 1, 3, and 4 by p-fluorophenyl, 3-(p-fluorophenyl)-3-hydroxypropyl, and 4-hydroxyphenyl groups, respectively (the 3R,3'S,4S enantiomer).	2.07	1	0	azetidines; beta-lactam; organofluorine compound	anticholesteremic drug; antilipemic drug; antimetabolite
3,3',4',5,6,7,8-heptamethoxyflavone 3,3',4',5,6,7,8-heptamethoxyflavone: has anti-inflammatory activity; isolated from citrus fruit; exhibit antiadhesive action on platelets	2	1	0	ether; flavonoids
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	2.07	1	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.	3.1	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.	2.99	4	0	oxygen hydride; oxygen radical; reactive oxygen species
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
atazanavir sulfate Atazanavir Sulfate: An azapeptide and HIV-PROTEASE INHIBITOR that is used in the treatment of HIV INFECTIONS and AIDS in combination with other ANTI-HIV AGENTS.	2.15	1	0	organic sulfate salt
olmesartan olmesartan: an active metabolite of CS 866	3.15	1	0	biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent
apigeninidin apigeninidin: a sorghum phytoalexin; structure given in first source	2.43	2	0
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.	2.02	1	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
cryptotanshinone cryptotanshinone: from Salvia miltiorrhiza	2.07	1	0	abietane diterpenoid	anticoronaviral agent
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	2.04	1	0
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
cortolone [no description available]	3.1	1	0	21-hydroxy steroid
maprounic acid maprounic acid: from Maprounea africana; structure given in first source. maprounic acid : A pentacyclic triterpenoid isolated from Maprounea africana and has been shown to exhibit inhibitory activity against HIV-1 reverse transcriptase.	2.07	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	HIV-1 reverse transcriptase inhibitor; plant metabolite
isovitexin [no description available]	3.9	3	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
hamaudol hamaudol: intermediate in the synthesis of furanochromones	2.07	1	0	chromenes
4'-hydroxyflavanone 4'-hydroxyflavanone: structure in first source. 4'-hydroxyflavanones : Any hydroxyflavanone having a hydroxy substituent located at position 4'.	2.05	1	0	4'-hydroxyflavanones; monohydroxyflavanone
leucodin leucodin: structure in first source	2.07	1	0	sesquiterpene lactone
procyanidin C1 procyanidin trimer C1: a flavonoid found in multiple plant sources including grape, apple, and cacao, which has antioxidant and anti-inflammatory properties. procyanidin C1 : A proanthocyanidin consisting of three (-)-epicatechin units joined by two successive (4beta->8)-linkages.	2.05	1	0	hydroxyflavan; polyphenol; proanthocyanidin	anti-inflammatory agent; antioxidant; EC 1.17.3.2 (xanthine oxidase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; lipoxygenase inhibitor; metabolite
varenicline Varenicline: A benzazepine derivative that functions as an ALPHA4-BETA2 NICOTINIC RECEPTOR partial agonist. It is used for SMOKING CESSATION.. varenicline : An organic heterotetracyclic compound that acts as a partial agonist for nicotinic cholinergic receptors and is used (in the form of its tartate salt) as an aid to giving up smoking.	3.57	2	0
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).	2.54	2	0	amino acid zwitterion; angiotensin II	human metabolite
sb 203580 [no description available]	2.79	3	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
erlotinib [no description available]	2.07	1	0	aromatic ether; quinazolines; secondary amino compound; terminal acetylenic compound	antineoplastic agent; epidermal growth factor receptor antagonist; protein kinase inhibitor
cilengitide Cilengitide: an alphaVbeta3 integrin antagonist that paralyzes cancer cells	3.15	1	0	oligopeptide
2'-hydroxyflavanone [no description available]	2.05	1	0
limonin [no description available]	4.78	9	0	epoxide; furans; hexacyclic triterpenoid; lactone; limonoid; organic heterohexacyclic compound	inhibitor; metabolite; volatile oil component
scutellarin scutellarin: see scutellarein for aglycone. scutellarin : The glycosyloxyflavone which is the 7-O-glucuronide of scutellarein.	2.07	1	0	glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antineoplastic agent; proteasome inhibitor
fixb protein, e coli muscarinic toxin 2: muscarinic agonists from Dendroaspis angusticeps; amino acid sequence given in first source. alpha-D-mannoside : Any mannoside in which the anomeric centre has alpha-configuration.. alpha-D-mannose : D-Mannopyranose having alpha-configuration at the anomeric centre.	3.51	1	0	D-mannopyranose	epitope
6-o-veratroyl catalpol [no description available]	2.07	1	0
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.	7.46	2	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
carbocysteine Carbocysteine: A compound formed when iodoacetic acid reacts with sulfhydryl groups in proteins. It has been used as an anti-infective nasal spray with mucolytic and expectorant action.. S-carboxymethyl-L-cysteine : An L-cysteine thioether that is L-cysteine in which the hydrogen of the thiol group has been replaced by a carboxymethyl group.	3.1	1	0	L-cysteine thioether; non-proteinogenic L-alpha-amino acid	mucolytic
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
(-)-gallocatechin gallate (-)-gallocatechin gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of (-)-gallocatechin. A natural product found in found in green tea.	2.02	1	0	catechin; gallate ester; polyphenol	antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human xenobiotic metabolite; plant metabolite
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
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
cholic acid Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.. cholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.	3.53	2	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse 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.	2.48	2	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C29-steroid; phytosterols; stigmastane sterol	anticholesteremic drug; antioxidant; mouse metabolite; plant metabolite; sterol methyltransferase inhibitor
4-allyl-2,6-dimethoxyphenol 4-allyl-2,6-dimethoxyphenol: structure in first source. 4-allyl-2,6-dimethoxyphenol : A member of the class of phenols that is phenol substituted by an allyl group at position 4 and methoxy groups at positions 2 and 6 respectively.	2.07	1	0	dimethoxybenzene; phenols; phenylpropanoid
5 alpha-androstane-3 beta,17 beta-diol 5alpha-androstane-3beta,17beta-diol : An androstane-3,17-diol that is 5alpha-androstane substituted by beta-hydroxy groups at positions 3 and 17. It is a metabolite of dihydrotestosterone.	3.1	1	0	17beta-hydroxy steroid; 3beta-hydroxy steroid; androstane-3,17-diol	Daphnia magna metabolite; human metabolite
cortol [no description available]	3.1	1	0	21-hydroxy steroid
21-hydroxypregnenolone 21-hydroxypregnenolone: RN given refers to (3beta)-isomer;. 21-hydroxypregnenolone : A hydroxypregnenolone that is pregnenolone which has been substituted by a hydroxy group at position 21.	3.1	1	0	21-hydroxy steroid; hydroxypregnenolone; primary alpha-hydroxy ketone	mouse metabolite
2-hydroxyestradiol 2-hydroxyestradiol: catechol estrogen; RN given refers to (17 beta)-isomer. 2-hydroxy-17beta-estradiol : A 2-hydroxy steroid that consists of 17beta-estradiol having an additional hydroxy group at position 2.	3.1	1	0	17beta-hydroxy steroid; 2-hydroxy steroid	carcinogenic agent; human metabolite; metabolite; mouse metabolite; prodrug
epietiocholanolone epietiocholanolone : A 3beta-hydroxy steroid that is 5beta-androstane substituted by a hydroxy group at position 3beta and an oxo group at position 17. It is a metabolite of testosterone.	3.1	1	0	17-oxo steroid; 3beta-hydroxy steroid; androstanoid	androgen; animal metabolite; human blood serum metabolite; mouse metabolite; rat metabolite
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.	2.07	1	0	monohydroxypyrrolidine; organonitrogen heterocyclic antibiotic	anticoronaviral agent; antimicrobial agent; antineoplastic agent; antiparasitic agent; bacterial metabolite; DNA synthesis inhibitor; protein synthesis inhibitor
lupeol [no description available]	7.6	1	0	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory drug; plant metabolite
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
Harringtonine harringtonin: alkaloid C from Caphalotaxus fortunei	2.07	1	0	alkaloid
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]	2.44	2	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
medicarpin (-)-medicarpin : The (-)-enantiomer of medicarpin.	2.06	1	0	medicarpin	plant metabolite
3,4-dihydroxyphenylpropionic acid 3,4-dihydroxyphenylpropionic acid: metabolite of caffeic acid; RN given refers to parent cpd; structure. 3-(3,4-dihydroxyphenyl)propanoic acid : A monocarboxylic acid that is 3-phenylpropionic acid substituted by hydroxy groups at positions 3 and 4. Also known as dihydrocaffeic acid, it is a metabolite of caffeic acid and exhibits antioxidant activity.	2.11	1	0	(dihydroxyphenyl)propanoic acid	antioxidant; human xenobiotic metabolite
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
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
5-demethylnobiletin 5-demethylnobiletin: antineoplastic from Citrus plants; structure in first source	2	1	0	ether; flavonoids
taurochenodeoxycholic acid Taurochenodeoxycholic Acid: A bile salt formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed. It is used as a cholagogue and choleretic.. taurochenodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurochenodeoxycholic acid arising from deprotonation of the sulfonate OH group; major species at pH 7.3.. taurochenodeoxycholic acid : A bile acid taurine conjugate of chenodeoxycholic acid.	2.07	1	0	bile acid taurine conjugate	human metabolite; mouse metabolite
8-deoxygartanin 8-deoxygartanin: a butyrylcholinesterase inhibitor; isolated from Garcinia mangostana; structure in first source	2.07	1	0	xanthones
ritonavir Ritonavir: An HIV protease inhibitor that works by interfering with the reproductive cycle of HIV. It also inhibits CYTOCHROME P-450 CYP3A.. ritonavir : An L-valine derivative that is L-valinamide in which alpha-amino group has been acylated by a [(2-isopropyl-1,3-thiazol-4-yl)methyl]methylcarbamoyl group and in which a hydrogen of the carboxamide amino group has been replaced by a (2R,4S,5S)-4-hydroxy-1,6-diphenyl-5-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}hexan-2-yl group. A CYP3A inhibitor and antiretroviral drug from the protease inhibitor class used to treat HIV infection and AIDS, it is often used as a fixed-dose combination with another protease inhibitor, lopinavir. Also used in combination with dasabuvir sodium hydrate, ombitasvir and paritaprevir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as cirrhosis of the liver.	8.9	3	0	1,3-thiazoles; carbamate ester; carboxamide; L-valine derivative; ureas	antiviral drug; environmental contaminant; HIV protease inhibitor; xenobiotic
tryptoquivaline fumitremorgin C : An organic heteropentacyclic compound that is a mycotoxic indole alkaloid produced by several fungi. A potent and specific inhibitor of the breast cancer resistance protein multidrug transporter.	3.15	1	0	aromatic ether; indole alkaloid; organic heteropentacyclic compound	breast cancer resistance protein inhibitor; mycotoxin
dihydropyridines Dihydropyridines: Pyridine moieties which are partially saturated by the addition of two hydrogen atoms in any position.	3.08	1	0
s-adenosylhomocysteine S-Adenosylhomocysteine: 5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine. Formed from S-adenosylmethionine after transmethylation reactions.. S-adenosyl-L-homocysteine : An organic sulfide that is the S-adenosyl derivative of L-homocysteine.	2.01	1	0	adenosines; amino acid zwitterion; homocysteine derivative; homocysteines; organic sulfide	cofactor; EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor; EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor; epitope; fundamental metabolite
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.	2.55	2	0
amylopectin Amylopectin: A highly branched glucan in starch.. amylopectin : A polydisperse highly branched polysaccharide derivative composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage. The chains are joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some 6-phosphate ester groups also may occur. The branches in amylopectin typically contain 24 to 30 glucose residues.	2.07	1	0
raffinose Raffinose: A trisaccharide occurring in Australian manna (from Eucalyptus spp, Myrtaceae) and in cottonseed meal.. raffinose : A trisaccharide composed of alpha-D-galactopyranose, alpha-D-glucopyranose and beta-D-fructofuranose joined in sequence by 1->6 and 1<->2 glycosidic linkages, respectively.	3.51	1	0	raffinose family oligosaccharide; trisaccharide	mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	12.44	116	4	(2S)-flavan-4-one; naringenin	expectorant; 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.	3.86	3	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
salicin [no description available]	2.05	1	0	aromatic primary alcohol; aryl beta-D-glucoside; benzyl alcohols	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
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.	8.34	6	0	taxifolin	metabolite
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	2.07	1	0	tartaric acid	Escherichia coli metabolite
taurolithocholic acid Taurolithocholic Acid: A bile salt formed in the liver from lithocholic acid conjugation with taurine, usually as the sodium salt. It solubilizes fats for absorption and is itself absorbed. It is a cholagogue and choleretic.. taurolithocholic acid : The bile acid taurine conjugate of lithocholic acid.	2.07	1	0	bile acid taurine conjugate; monocarboxylic acid amide	human metabolite
n'-formylkynurenine N'-formylkynurenine: a photochemical breakdown product of tryptophan in proteins; RN given refers to parent cpd without isomeric designation	2.1	1	0	amino acid zwitterion; N-formylkynurenine; non-proteinogenic amino acid derivative; non-proteinogenic L-alpha-amino acid	human metabolite; mouse metabolite; Saccharomyces cerevisiae 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
2-hydroxyestrone 2-hydroxyestrone: catechol estrogen which is a major metabolite of estradiol in man & animals; RN given refers to parent cpd. 2-hydroxyestrone : A 2-hydroxy steroid that is estrone substituted by a hydroxy group at position 2.	3.1	1	0	2-hydroxy steroid; catechols	human metabolite
eriodictyol eriodictyol: structure. eriodictyol : A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' respectively.	2.97	4	0	3'-hydroxyflavanones; tetrahydroxyflavanone
pelargonidin pelargonidin: influences flower phenotype. pelargonidin : An anthocyanidin cation that is flavylium substituted by a hydroxy groups at positions 3, 5, 7 and 4'.	2.01	1	0	5-hydroxyanthocyanidin	plant metabolite
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.	2.49	2	0	beta-D-glucoside; monosaccharide derivative	Escherichia coli metabolite; plant metabolite
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.	4.42	6	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.	2.07	1	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.	2.07	1	0	cardenolide glycoside	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
saquinavir Saquinavir: An HIV protease inhibitor which acts as an analog of an HIV protease cleavage site. It is a highly specific inhibitor of HIV-1 and HIV-2 proteases, and also inhibits CYTOCHROME P-450 CYP3A.. saquinavir : An aspartic acid derivative obtained by formal condensation of the primary amino group of (2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-ylamine with the carboxy group of N(2)(-quinolin-2-ylcarbonyl)-L-asparagine. An inhibitor of HIV-1 protease.	9.25	5	0	L-asparagine derivative; quinolines	antiviral drug; HIV protease 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
epiandrosterone epiandrosterone : A 3beta-hydroxy steroid that is (5alpha)-androstane substituted by a beta-hydroxy group at position 3 and an oxo group at position 17.	3.1	1	0	17-oxo steroid; 3beta-hydroxy steroid; androstanoid	androgen; human metabolite
saponarin saponarin: structure in first source. 7-O-(beta-D-glucosyl)isovitexin : A C-glycosyl compound that is isovitexin in which the hydroxyl hydrogen at position 7 is replaced by a beta-D-glucosyl residue.	2.25	1	0	C-glycosyl compound; dihydroxyflavone; glycosyloxyflavone; monosaccharide derivative	metabolite
deltaline [no description available]	2.07	1	0	acetate ester; cyclic acetal; diterpene alkaloid; organic polycyclic compound; tertiary alcohol; tertiary amino compound
ginsenoside re [no description available]	2.11	1	0	12beta-hydroxy steroid; 3beta-hydroxy-4,4-dimethylsteroid; 3beta-hydroxy steroid; beta-D-glucoside; disaccharide derivative; ginsenoside; tetracyclic triterpenoid	anti-inflammatory agent; antineoplastic agent; antioxidant; nephroprotective agent; neuroprotective agent; plant metabolite
ingenol [no description available]	2.07	1	0	cyclic terpene ketone; tetracyclic diterpenoid
stevioside stevioside: Kaurene glucoside from leaves of Stevia rebaudiana; 300 times as sweet as sugar. stevioside : A diterpene glycoside that is rubusoside in which the hydroxy group at position 2 of the allylic beta-D-glucoside has been converted to the corresponding beta-D-glucoside. It is a natural herbal sweetener that is 250-300 times sweeter than sucrose (though with a bitter aftertaste), extracted from the Stevia rebaudiana plant native to South America.. diterpene glycoside : A terpene glycoside in which the terpene moiety is a diterpenoid.	2.25	1	0	beta-D-glucoside; bridged compound; diterpene glycoside; ent-kaurane diterpenoid; tetracyclic diterpenoid	anti-inflammatory agent; antineoplastic agent; antioxidant; hypoglycemic agent; plant metabolite; sweetening agent
abyssinone v abyssinone V: isolated from Erythrina sigboidea; RN from Chemical Abstracts Index Guide; structure given in first source. abyssinone V : A trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7 and 4' and prenyl groups at positions 3' and 5' respectively.	2.03	1	0	4'-hydroxyflavanones; phenols; trihydroxyflavanone	metabolite
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
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.	4.37	19	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; rutinoside	anti-inflammatory agent; antioxidant; metabolite
pulegone pulegone: component of peppermint oil; RN given refers to cpd without isomeric designation; structure in Merck. (+)-pulegone : The (5R)-enantiomer of p-menth-4(8)-en-3-one.	1.98	1	0	p-menth-4(8)-en-3-one
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.	2.07	1	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
vicenin ii vicenin: isolated from the leaves of the Indian plant Ocimum sanctum were tested for their radioprotective effect in mice. isovitexin 8-C-beta-glucoside : A C-glycosyl compound that is isovitexin in which the hydrogen at position 8 is replaced by a beta-D-glucosyl residue.	2.1	1	0	C-glycosyl compound; trihydroxyflavone	metabolite
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.	2.07	1	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
alpha bitter acid humulon: antibiotic from hops; structure	2.02	1	0	aromatic ketone; cyclic ketone; diketone; tertiary alpha-hydroxy ketone; triol	antibacterial drug; antioxidant; cyclooxygenase 2 inhibitor; metabolite
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)	3.31	6	0
1-alpha-terpineol (S)-(-)-alpha-terpineol : The (S)-enantiomer of alpha-terpineol.	3.1	1	0	alpha-terpineol	plant metabolite
diprenorphine Diprenorphine: A narcotic antagonist similar in action to NALOXONE. It is used to remobilize animals after ETORPHINE neuroleptanalgesia and is considered a specific antagonist to etorphine.	3.1	1	0	morphinane alkaloid
sodium arsenite sodium arsenite : An inoganic sodium salt with formula with formula NaAsO2.	2.52	2	0	arsenic molecular entity; inorganic sodium salt	antibacterial agent; antifungal agent; antineoplastic agent; carcinogenic agent; herbicide; insecticide; rodenticide
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
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	3.19	5	0	cyclodextrin
acarbose [no description available]	2.49	2	0	amino cyclitol; glycoside
ergosterol [no description available]	3.1	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae 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.	3.82	3	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.	2.06	1	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.	2.98	4	0	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).	4.03	4	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
cyanoginosin lr cyanoginosin LR: cyclic heptapeptide from cyanobacterium Microcystis aeruginosa. microcystin-LR : A microcystin consisting of D-alanyl, L-leucyl, (3S)-3-methyl-D-beta-aspartyl,L-arginyl, 2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl, D-gamma-glutamyl, and 2,3-didehydro-N-methylalanyl residues joined into a 25-membered macrocycle. Produced by the cyanobacterium Microcystis aeruginosa, it is the most studied of the microcystins.	2.44	2	0	microcystin	bacterial metabolite; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; environmental contaminant; xenobiotic
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	9.89	10	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.	2.41	1	0	D-galactopyranuronic acid
cerivastatin cerivastatin: cerivastatin is the ((E)-(+))-isomer; structure given in first source. cerivastatin : (3R,5S)-3,5-dihydroxyhept-6-enoic acid in which the (7E)-hydrogen is substituted by a 4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl group. Formerly used (as its sodium salt) to lower cholesterol and prevent cardiovascular disease, it was withdrawn from the market worldwide in 2001 following reports of a severe form of muscle toxicity.	2.07	1	0	dihydroxy monocarboxylic acid; pyridines; statin (synthetic)
rosuvastatin rosuvastatin : A dihydroxy monocarboxylic acid that is (6E)-7-{4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl} hept-6-enoic acid carrying two hydroxy substituents at positions 3 and 5 (the 3R,5S-diastereomer).	2.07	1	0	dihydroxy monocarboxylic acid; monofluorobenzenes; pyrimidines; statin (synthetic); sulfonamide	anti-inflammatory agent; antilipemic drug; cardioprotective agent; CETP inhibitor; environmental contaminant; xenobiotic
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.	3.53	2	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
lycopene [no description available]	2.07	1	0	acyclic carotene	antioxidant; plant metabolite
diethylstilbestrol Diethylstilbestrol: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). diethylstilbestrol : An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.	3.53	2	0	olefinic compound; polyphenol	antifungal agent; antineoplastic agent; autophagy inducer; calcium channel blocker; carcinogenic agent; EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; endocrine disruptor; xenoestrogen
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
h 89 N-(2-(4-bromocinnamylamino)ethyl)-5-isoquinolinesulfonamide: structure given in first source. N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A member of the class of isoquinolines that is the sulfonamide obtained by formal condensation of the sulfo group of isoquinoline-5-sulfonic acid with the primary amino group of N(1)-[3-(4-bromophenyl)prop-2-en-1-yl]ethane-1,2-diamine. It is a protein kinase A inhibitor.. (E)-N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide in which the double bond adopts a trans-configuration.	2.11	1	0	N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide
afimoxifene afimoxifene : A tertiary amino compound that is tamoxifen in which the phenyl group which is in a Z- relationship to the ethyl substituent is hydroxylated at the para- position. It is the active metabolite of tamoxifen.	2.04	1	0	phenols; tertiary amino compound	antineoplastic agent; estrogen receptor antagonist; metabolite
iridoids Iridoids: A type of MONOTERPENES, derived from geraniol. They have the general form of cyclopentanopyran, but in some cases, one of the rings is broken as in the case of secoiridoid. They are different from the similarly named iridals (TRITERPENES).	2.8	3	0
12-deoxyphorbol 13-acetate [no description available]	2.07	1	0	phorbol ester	metabolite
cefamandole Cefamandole: Semisynthetic wide-spectrum cephalosporin with prolonged action, probably due to beta-lactamase resistance. It is used also as the nafate.. cefamandole : A cephalosporin compound having (R)-mandelamido and N-methylthiotetrazole side-groups.	2.07	1	0	cephalosporin; semisynthetic derivative	antibacterial drug
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.	2.44	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
tenofovir tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.	3.57	2	0	nucleoside analogue; phosphonic acids	antiviral drug; drug metabolite; HIV-1 reverse transcriptase inhibitor
euscaphic acid euscaphic acid: isolated from medicinal plant, Euscaphis japonica Pax.; structure; RN given refers to 2alpha,3alpha-isomer. euscaphic acid : A pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 19 respectively (the 2alpha,3alpha-stereoisomer). It has been isolated from the leaves of Rosa laevigata.	2.03	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid; triol	plant metabolite
(+)-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
likviriton liquiritin: isoalted from Glycyrrhizae radix. liquiritin : A flavanone glycoside that is liquiritigenin attached to a beta-D-glucopyranosyl residue at position 4' via a glycosidic linkage.	3.15	5	0	beta-D-glucoside; flavanone glycoside; monohydroxyflavanone; monosaccharide derivative	anti-inflammatory agent; anticoronaviral agent; plant metabolite
ammonium acetate ammonium acetate : An ammonium salt obtained by reaction of ammonia with acetic acid. A deliquescent white crystalline solid, it has a relatively low melting point (114degreeC) for a salt. Used as a food acidity regulator, although no longer approved for this purpose in the EU.	2.44	2	0	acetate salt; ammonium salt	buffer; food acidity regulator
carbenoxolone sodium Carbenoxolone: An agent derived from licorice root. It is used for the treatment of digestive tract ulcers, especially in the stomach. Antidiuretic side effects are frequent, but otherwise the drug is low in toxicity.	1.98	1	0	triterpenoid
drimanial drimanial: isolated from the bark of Drimys wintery (Winteraceae); structure in first source	2.03	1	0
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
3-coumaric acid 3-coumaric acid: RN given refers to cpd without isomeric designation in Chemline. trans-3-coumaric acid : A 3-coumaric acid that is phenol substituted with trans-2-propenoic acid at position C-3.. 3-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-3 of the phenyl ring.	2.07	1	0	3-coumaric acid
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	2.1	1	0	4-coumaric acid	food component; mouse metabolite; plant metabolite
geraniol [no description available]	3.1	1	0	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	6.2	25	0
chalcone trans-chalcone : The trans-isomer of chalcone.	2.88	3	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
sinapinic acid sinapinic acid: a matrix for matrix-assisted laser desorption technique for protein MW determination; a constituent of propolis. trans-sinapic acid : A sinapic acid in which the double bond has trans-configuration.	3.66	2	0	sinapic acid	MALDI matrix material; plant metabolite
piperine 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.	3.59	2	0	benzodioxoles; N-acylpiperidine; piperidine alkaloid; tertiary carboxamide	food component; human blood serum metabolite; NF-kappaB inhibitor; plant metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.75	3	0	stilbene
isoliquiritigenin [no description available]	2.45	2	0	chalcones	antineoplastic agent; biological pigment; EC 1.14.18.1 (tyrosinase) inhibitor; GABA modulator; geroprotector; metabolite; NMDA receptor antagonist
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.	3.6	2	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
rauwolscine Rauwolscine: A stereoisomer of yohimbine.	2.07	1	0	methyl 17-hydroxy-20xi-yohimban-16-carboxylate
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.	3.15	1	0	olefinic compound; phytocannabinoid; resorcinols	antimicrobial agent; plant metabolite
malonyl coenzyme a Malonyl Coenzyme A: A coenzyme A derivative which plays a key role in the fatty acid synthesis in the cytoplasmic and microsomal systems.. omega-carboxyacyl-CoA : An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of any alpha,omega-dicarboxylic acid.	2.17	1	0	malonyl-CoAs	EC 2.3.1.21 (carnitine O-palmitoyltransferase) inhibitor; Escherichia coli metabolite; metabolite; mouse metabolite
gw9662 2-chloro-5-nitrobenzanilide: pretreatment of peroxisome proliferator activated receptors with GW9662 results in the irreversible loss of ligand binding	2.51	2	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
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.	7.4	2	0	pyrimidinethione	antidote to paracetamol poisoning; antimetabolite; antioxidant; antithyroid drug; carcinogenic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor; hormone antagonist
sesquiterpenes [no description available]	2.45	2	0
chlorprothixene Chlorprothixene: A thioxanthine with effects similar to the phenothiazine antipsychotics.. (Z)-chlorprothixene : A chlorprothixene in which the double bond adopts a (Z)-configuration.	2.07	1	0	chlorprothixene
dienestrol Dienestrol: A synthetic, non-steroidal estrogen structurally related to stilbestrol. It is used, usually as the cream, in the treatment of menopausal and postmenopausal symptoms.. dienestrol : An olefinic compound that is hexa-2,4-diene substituted by 4-hydroxyphenyl groups at positions 3 and 4 respectively.	3.1	1	0
vasicine vasicine: RN given refers to (R)-isomer	2.07	1	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
3,6-dihydroxyflavone 3,6-dihydroxyflavone: induces apoptosis in leukemia HL-60 cells; structure in first source	2.05	1	0
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	8.33	6	0	caffeic acid	geroprotector; mouse metabolite
captax captax: RN given refers to parent cpd. 1,3-benzothiazole-2-thiol : 1,3-Benzothiazole substituted at the 2-position with a sulfanyl group.	3.1	1	0	aryl thiol; benzothiazoles	carcinogenic agent; metabolite
isoferulic acid isoferulic acid: isomer of ferulic acid; structure. isoferulic acid : A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring.	2.11	1	0	ferulic acids	antioxidant; biomarker; metabolite
4-(4-(4-chloro-phenyl)thiazol-2-ylamino)phenol [no description available]	2.11	1	0	substituted aniline
7-benzyloxy-4-trifluoromethylcoumarin 7-benzyloxy-4-trifluoromethylcoumarin: a substrate for CYP3A4	2.13	1	0
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
thiothixene [no description available]	3.1	1	0	N-methylpiperazine	anticoronaviral agent
tetrahydropalmatine [no description available]	2.03	1	0
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.	5.66	5	1	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
nootkatone nootkatone: RN given refers to cpd without isomeric designation; structure given in first source. (+)-nootkatone : A sesquiterpenoid that is 4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one which is substituted by methyl groups at positions 4 and 4a, and by an isopropenyl group at position 6 (the 4R,4aS,6R stereoisomer).	2.07	1	0	carbobicyclic compound; enone; sesquiterpenoid	fragrance; insect repellent; plant metabolite
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.	2.78	3	0	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.	7.84	3	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
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.	9.77	9	0	cinnamate ester; tannin	food component; plant metabolite
meranzin meranzin: structure in first source	2.69	2	0
D-fructopyranose [no description available]	4.21	3	1	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	7.15	1	0	thiocarboxamide	hepatotoxic agent
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.	3.86	3	0	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
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]	7.46	2	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
sodium taurodeoxycholate Taurodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. It is used as a cholagogue and choleretic, also industrially as a fat emulsifier.. taurodeoxycholic acid : A bile acid taurine conjugate of deoxycholic acid.. taurodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurodeoxycholic acid.	2.07	1	0	bile acid taurine conjugate	human metabolite
1-butyl-3-methylimidazolium tetrafluoroborate [no description available]	2.47	2	0
6-hydroxyflavanone 6-hydroxyflavanone : A monohydroxyflavanone that is flavanone substituted by a hydroxy group at position 6.	2.05	1	0	monohydroxyflavanone	fungal xenobiotic metabolite
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)	3.45	7	0
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
estrone sulfate estrone sulfate: sulfoconjugated estrone; RN given refers to parent cpd	4.26	5	0	17-oxo steroid; steroid sulfate	human metabolite; mouse metabolite
u 0126 U 0126: protein kinase kinase inhibitor; structure in first source	2.48	2	0	aryl sulfide; dinitrile; enamine; substituted aniline	antineoplastic agent; antioxidant; apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; osteogenesis regulator; vasoconstrictor agent
glycylproline Gly-Pro : A dipeptide consisting of L-proline having a glycyl residue attached to its alpha-amino group.	3.57	2	0	dipeptide zwitterion; dipeptide	metabolite
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]	6.12	9	1	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
12-deoxyphorbolphenylacetate-20-acetate [no description available]	2.07	1	0
glycodeoxycholic acid Glycodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic.. glycodeoxycholic acid : A bile acid glycine conjugate of deoxycholic acid.	2.07	1	0	bile acid glycine conjugate	human metabolite
brassinin [no description available]	2.07	1	0	dithiocarbamic ester; indole phytoalexin
sch 23390 SCH 23390: a selective D1-receptor antagonist. SCH 23390 : A benzazepine that is 2,3,4,5-tetrahydro-3-benzazepine bearing a phenyl substituent at position 1, a methyl substituent at position 3, a chloro substituent at position 7 and a hydroxy substituent at position 8.	3.53	2	0	benzazepine
chaetomellic acid a chaetomellic acid A: structure given in first source; an inhibitor of farnesyl-protein transferase	2.07	1	0
hirsutine [no description available]	2.07	1	0
3-deoxyvasicine, hydrochloride [no description available]	2.07	1	0
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
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.44	2	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.	2.52	2	0
silybin [no description available]	2.49	2	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.78	3	0
mtt formazan MTT formazan: a blue MEM-insoluble mitochondrial byproduct; used to determine viability of cells with active mitochondrial dehydrogenase enzymes	2.03	1	0
zinc protoporphyrin ix [no description available]	2.13	1	0
am 630 iodopravadoline: an aminoalkylindole; a competitive cannabinoid receptor antagonist; structure given in first source	3.15	1	0	N-acylindole
digitoxigenin Digitoxigenin: 3 beta,14-Dihydroxy-5 beta-card-20(22)enolide. A cardenolide which is the aglycon of digitoxin. Synonyms: Cerberigenin; Echujetin; Evonogenin; Thevetigenin.. digitoxigenin : A 5beta-cardenolide that is 5beta-cardanolide with hydroxy substituents at the 3beta- and 14beta-positions and double bond unsaturation at C(20)-C(22).	3.1	1	0	14beta-hydroxy steroid; 3beta-hydroxy steroid
osteoprotegerin Osteoprotegerin: A secreted member of the TNF receptor superfamily that negatively regulates osteoclastogenesis. It is a soluble decoy receptor of RANK LIGAND that inhibits both CELL DIFFERENTIATION and function of OSTEOCLASTS by inhibiting the interaction between RANK LIGAND and RECEPTOR ACTIVATOR OF NUCLEAR FACTOR-KAPPA B.	7.83	3	0	long-chain fatty acid
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
catechin gallate catechin gallate: structure in first source. (+)-catechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3S)-hydroxy group of (+)-catechin.	2.52	2	0	flavans; gallate ester; polyphenol	metabolite
quercetin [no description available]	8.58	48	1	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]	4.04	2	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.	4.23	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
bergaptol 5-hydroxyfurocoumarin : A furanocoumarin which bears a hydroxy group at position 5.	2.06	1	0	5-hydroxyfurocoumarin; psoralens
biochanin a [no description available]	3.01	4	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]	2.94	4	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]	2.79	3	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.	2.97	4	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.	5.23	15	0	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	3.03	4	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]	8.1	5	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]	3.84	3	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.	2.95	4	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.	3.53	2	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.	3.01	4	0	beta-D-glucoside; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antioxidant; plant metabolite
gossypetin gossypetin: inhibits activity of penicillinase enzyme in E coli. gossypetin : A hexahydroxyflavone having the hydroxy groups placed at the 3-, 3'-, 4'-, 5- 7- and 8-positions.	2	1	0	7-hydroxyflavonol; hexahydroxyflavone	plant metabolite
chrysoeriol chrysoeriol: isolated from leaves of Eurya japonica & E. emarginata. 4',5,7-trihydroxy-3'-methoxyflavone : The 3'-O-methyl derivative of luteolin.	2	1	0	monomethoxyflavone; trihydroxyflavone	antineoplastic agent; antioxidant; metabolite
quercetin 3-o-methyl ether quercetin 3-O-methyl ether: from Rhamnus species; structure in first source. 3',4',5,7-tetrahydroxy-3-methoxyflavone : A tetrahydroxyflavone having the 4-hydroxy groups located at the 3'- 4'- 5- and 7-positions as well as a methoxy group at the 2-position.	2	1	0	monomethoxyflavone; tetrahydroxyflavone	antimicrobial agent; metabolite
apigetrin apigetrin: structure given in first source. apigenin 7-O-beta-D-glucoside : A glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.05	1	0	beta-D-glucoside; dihydroxyflavone; glycosyloxyflavone; monosaccharide derivative	antibacterial agent; metabolite; non-steroidal anti-inflammatory drug
alprostadil [no description available]	2.07	1	0	prostaglandins E	anticoagulant; human metabolite; platelet aggregation inhibitor; vasodilator agent
vitamin d 2 Ergocalciferols: Derivatives of ERGOSTEROL formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. They differ from CHOLECALCIFEROL in having a double bond between C22 and C23 and a methyl group at C24.. vitamin D2 : A vitamin D supplement and has been isolated from alfalfa.	3.1	1	0	hydroxy seco-steroid; seco-ergostane; vitamin D	bone density conservation agent; nutraceutical; plant metabolite; rodenticide
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.	2.07	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.	4.94	2	1	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	2.99	4	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.	6.06	36	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
bilirubin diglucuronide [no description available]	3.15	1	0
kaempferol [no description available]	3.65	9	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
alpha-linolenic acid linolenic acid : A two-membered subclass of octadecatrienoic acid comprising the (9Z,12Z,15Z)- and (6Z,9Z,12Z)-isomers. Linolenic acids are nutrients essential to the formation of prostaglandins and are also used in making paints and synthetic resins.. linolenate : A polyunsaturated fatty acid anion obtained by deprotonation of the carboxy group of either alpha- or gamma-linolenic acid.	2.15	1	0	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
genistein [no description available]	5.24	15	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.	2.07	1	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.	2.07	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
butein [no description available]	2.47	2	0	chalcones; polyphenol	antineoplastic agent; antioxidant; EC 1.1.1.21 (aldehyde reductase) inhibitor; geroprotector; hypoglycemic agent; plant metabolite; radiosensitizing agent; tyrosine kinase inhibitor
lutein Lutein: A xanthophyll found in the major LIGHT-HARVESTING PROTEIN COMPLEXES of plants. Dietary lutein accumulates in the MACULA LUTEA.. xanthophyll : A subclass of carotenoids consisting of the oxygenated carotenes.	2.02	1	0	carotenol	food colouring; plant metabolite
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	2.74	3	0	7-hydroxyisoflavones 7-O-beta-D-glucoside
chartreusin chartreusin: structure	2.07	1	0	benzochromenone; glycoside
esculetin esculetin: used in filters for absorption of ultraviolet light; structure. esculetin : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.	3.83	3	0	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
esculin [no description available]	2.47	2	0	beta-D-glucoside; hydroxycoumarin	antioxidant; metabolite
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	3.78	3	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
oleuropein oleuropein: iridoid isolated from leaves and fruit of Olea and Ligustrum (Oleaceae). oleuropein : A secoiridoid glycoside that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the anomeric hydroxy group at position 2 has been converted into its beta-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2S,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars.	2.15	1	0	beta-D-glucoside; catechols; diester; methyl ester; pyrans; secoiridoid glycoside	anti-inflammatory agent; antihypertensive agent; antineoplastic agent; antioxidant; apoptosis inducer; NF-kappaB inhibitor; nutraceutical; plant metabolite; radical scavenger
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
amentoflavone [no description available]	2.07	1	0	biflavonoid; hydroxyflavone; ring assembly	angiogenesis inhibitor; antiviral agent; cathepsin B inhibitor; P450 inhibitor; plant metabolite
baicalein [no description available]	9.55	7	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.	9.86	10	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]	2.78	3	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]	3.44	7	0	dihydroxyflavanone; disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; rutinoside	anti-inflammatory agent; antioxidant
fisetin [no description available]	9.67	8	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.	4.23	5	0	7-hydroxyflavonol; trihydroxyflavone	antimicrobial agent; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; plant metabolite
gossypin gossypin: do not confuse with gossypin(e) which is synonym for choline. gossypin : A glycosyloxyflavone that is gossypetin attached to a beta-D-glucopyranosyl residue at position 8 via a glycosidic linkage.	7.05	1	0	7-hydroxyflavonol; glycosyloxyflavone; monosaccharide derivative; pentahydroxyflavone	neuroprotective agent; plant metabolite
hyperoside quercetin 3-O-beta-D-galactopyranoside : A quercetin O-glycoside that is quercetin with a beta-D-galactosyl residue attached at position 3. Isolated from Artemisia capillaris, it exhibits hepatoprotective activity.	2.47	2	0	beta-D-galactoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	hepatoprotective agent; plant metabolite
mangostin mangostin: xanthone from rind of Garcinia mangostana Linn. fruit. alpha-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3 and 6, a methoxy group at position 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antioxidant, antimicrobial and antitumour activities.	2.07	1	0	aromatic ether; phenols; xanthones	antimicrobial agent; antineoplastic agent; antioxidant; plant metabolite
3-methylquercetin isorhamnetin : A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.	2.47	2	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.	3.76	10	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]	8.65	9	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
myricitrin myricitrin: isolated from root bark of Myrica cerifera L.; structure. myricitrin : A glycosyloxyflavone that consists of myricetin attached to a alpha-L-rhamnopyranosyl residue at position 3 via a glycosidic linkage. Isolated from Myrica cerifera, it exhibits anti-allergic activity.	7.05	1	0	alpha-L-rhamnoside; glycosyloxyflavone; monosaccharide derivative; pentahydroxyflavone	anti-allergic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; plant metabolite
orientin orientin: structure given in first source; RN given refers to the (D-glucopyranosyl)-isomer. orientin : A C-glycosyl compound that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 8.	2.05	1	0	3'-hydroxyflavonoid; C-glycosyl compound; tetrahydroxyflavone	antioxidant; metabolite
rhamnetin rhamnetin: aglycone of xanthorhamnin; from Rhamnus. rhamnetin : A monomethoxyflavone that is quercetin methylated at position 7.	2.73	3	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
sciadopitysin sciadopitysin: biflavonoid from Taxus celebica & Ginkgo biloba. sciadopitysin : A biflavonoid that is a 7, 4', 4'''-trimethyl ether derivative of amentoflavone.	3.15	1	0	biflavonoid; hydroxyflavone; methoxyflavone; ring assembly	bone density conservation agent; platelet aggregation inhibitor
scutellarein scutellarein: aglycone of scutellarin from Scutellaria baicalensis; carthamidin is 2S isomer of scutellarein; do not confuse with isoscutellarein and/or isocarthamidin which are respective regioisomers, or with the scutelarin protein. scutellarein : Flavone substituted with hydroxy groups at C-4', -5, -6 and -7.	2.07	1	0	tetrahydroxyflavone	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.	2.07	1	0	dihydroxyflavone; monomethoxyflavone	angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite
7-hydroxy-6,4'-dimethoxyisoflavone afromosin: structure given in first source; isolated from Wistaria brachybotrys. afrormosin : A 4'-methoxyisoflavone that is isoflavone substituted by methoxy groups at positions 6 and 4' and a hydroxy group at position 7.	2.06	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	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.	2.48	2	0	coumestans; delta-lactone; polyphenol	anti-inflammatory agent; antioxidant; plant metabolite
daidzein [no description available]	3.45	7	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
cynarine cynarine: active principle of the artichoke; functions primarily as a cholagogue and choleretic and also as antilipemic agent	2.11	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.	2.07	1	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.	2.49	2	0	rosmarinic acid	geroprotector; plant metabolite
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.	3.51	1	0	catechols; cinnamate ester; disaccharide derivative; glycoside; polyphenol	anti-inflammatory agent; antibacterial agent; antileishmanial agent; neuroprotective agent; plant metabolite
psi-baptigenin pseudobaptigenin : A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone and in which the phenyl group at position 3 is replaced by a 1,3-benzodioxol-5-yl group.	2.06	1	0	7-hydroxyisoflavones; benzodioxoles	antiprotozoal drug; 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]	3.92	3	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
flupenthixol cis-flupenthixol : A flupenthixol in which the double bond adopts a cis-configuration.	2.07	1	0	flupenthixol	dopaminergic antagonist
sdz psc 833 valspodar: nonimmunosuppressive cyclosporin analog which is a potent multidrug resistance modifier; 7-10 fold more potent than cyclosporin A; a potent P glycoprotein inhibitor; MW 1215	2.07	1	0	homodetic cyclic peptide
estradiol-17 beta-glucuronide 17beta-estradiol 17-glucosiduronic acid : A steroid glucosiduronic acid that consists of 17beta-estradiol having a beta-glucuronyl residue attached at position 17 via a glycosidic linkage.	3.57	2	0	3-hydroxy steroid; steroid glucosiduronic acid
l 660,711 [no description available]	2.07	1	0	quinolines
7-hydroxyflavone 7-hydroxyflavone : A hydroxyflavonoid in which the flavone nucleus is substituted at position 7 by a hydroxy group.	2.73	3	0	hydroxyflavonoid
prostaglandin a1 [no description available]	2.07	1	0	prostaglandins A
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
astragalin kaempferol-3-O-glucoside: isolated from the pit of Mahkota dewa; structure in first source. kaempferol 3-O-beta-D-glucoside : A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage.	2.15	1	0	beta-D-glucoside; kaempferol O-glucoside; monosaccharide derivative; trihydroxyflavone	plant metabolite; trypanocidal drug
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.	4.3	5	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
4-hydroxyestradiol 4-hydroxyestradiol: catechol estrogen. 4-hydroxy-17beta-estradiol : A 4-hydroxy steroid that consists of 17beta-estradiol having an additional hydroxy group at position 4.	3.1	1	0	4-hydroxy steroid	metabolite
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.	3.53	2	0	retinoic acid	antineoplastic agent; keratolytic drug; teratogenic agent
pitavastatin pitavastatin : A dihydroxy monocarboxylic acid that is (6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]hept-6-enoic acid in which the two hydroxy groups are located at positions 3 and 5 (the 3R,5S-stereoisomer). Used as its calcium salt for treatment of hypercholesterolemia (elevated levels of cholesterol in the blood) on patients unable to sufficiently lower their cholesterol levels by diet and exercise.	2.47	2	0	cyclopropanes; dihydroxy monocarboxylic acid; monofluorobenzenes; quinolines; statin (synthetic)	antioxidant
hyodeoxycholic acid hyodeoxycholic acid: differs from deoxycholic acid in that the 6 alpha-OH is in the 12 position in the former; RN given refers to (3alpha,5beta,6alpha)-isomer. hyodeoxycholic acid : A member of the class of 5beta-cholanic acids that is (5beta)-cholan-24-oic acid substituted by alpha-hydroxy groups at positions 3 and 6.	3.1	1	0	5beta-cholanic acids; 6alpha,20xi-murideoxycholic acid; bile acid; C24-steroid	human metabolite; mouse metabolite
codeine [no description available]	3.53	2	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	3.86	3	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
hydromorphone Hydromorphone: An opioid analgesic made from MORPHINE and used mainly as an analgesic. It has a shorter duration of action than morphine.. hydromorphone : A morphinane alkaloid that is a hydrogenated ketone derivative of morphine. A semi-synthetic drug, it is a centrally acting pain medication of the opioid class.	3.1	1	0	morphinane alkaloid; organic heteropentacyclic compound	mu-opioid receptor agonist; opioid analgesic
nalmefene nalmefene: RN given refers to 5-alpha isomer	3.1	1	0	morphinane alkaloid
nalorphine Nalorphine: A narcotic antagonist with some agonist properties. It is an antagonist at mu opioid receptors and an agonist at kappa opioid receptors. Given alone it produces a broad spectrum of unpleasant effects and it is considered to be clinically obsolete.	3.1	1	0	morphinane alkaloid
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.	3.1	1	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
oxycodone Oxycodone: A semisynthetic derivative of CODEINE.. oxycodone : A semisynthetic opioid of formula C18H21NO4 that is derived from thebaine. It is a moderately potent opioid analgesic, generally used for relief of moderate to severe pain.	3.1	1	0	organic heteropentacyclic compound; semisynthetic derivative	antitussive; mu-opioid receptor agonist; opioid analgesic
oxymorphone Oxymorphone: An opioid analgesic with actions and uses similar to those of MORPHINE, apart from an absence of cough suppressant activity. It is used in the treatment of moderate to severe pain, including pain in obstetrics. It may also be used as an adjunct to anesthesia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1092)	3.1	1	0	morphinane alkaloid
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.	2.44	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
6alpha-hydroxy-17beta-estradiol 6alpha-hydroxy-17beta-estradiol : A 4-hydroxy steroid that consists of 17beta-estradiol bearing an additional 6alpha-hydroxy substituent.	3.1	1	0	6alpha-hydroxy steroid
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.	3.53	2	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
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.	2.17	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.	2.07	1	0	cytochalasin; lactam; lactone; organic heterotricyclic compound	actin polymerisation inhibitor; metabolite; mycotoxin; platelet aggregation inhibitor
nalbuphine Nalbuphine: A narcotic used as a pain medication. It appears to be an agonist at KAPPA RECEPTORS and an antagonist or partial agonist at MU RECEPTORS.	3.1	1	0	organic heteropentacyclic compound	mu-opioid receptor antagonist; opioid analgesic
vinorelbine [no description available]	2.07	1	0	acetate ester; methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; ring assembly; vinca alkaloid	antineoplastic agent; photosensitizing agent
kn 93 KN 93: reduces dopamine content in PC12h cells. KN-93 : A sulfonamide resulting from the formal condensation of p-methoxybenzenesulfonic acid with the anilino nitrogen of 2-(aminomethyl)-N-(2-hydroxyethyl)aniline in which the hydrogens of the primary amino group have been replaced by methyl and p-chlorocinnamyl groups. KN-93 is a selective inhibitor of Ca(2+)/calmodulin-dependent protein kinase II.	1.99	1	0	monochlorobenzenes; monomethoxybenzene; primary alcohol; sulfonamide; tertiary amino compound	EC 2.7.11.17 (Ca(2+)/calmodulin-dependent protein kinase) inhibitor; geroprotector
kn 62 KN 62: inhibitor of Ca/calmodulin-dependent protein kinase II	2.39	2	0	piperazines
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.	2.45	2	0	beta-diketone; diarylheptanoid; enone; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; metabolite
cinnamyl alcohol cinnamyl alcohol: RN given refers to parent cpd without isomeric designation. (E)-cinnamyl alcohol : The E (trans) stereoisomer of cinnamyl alcohol.. cinnamyl alcohol : A primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified).	3.1	1	0	cinnamyl alcohol	plant metabolite
linarin linarin: flavone glycoside isolated from leaves of Linaria japonica MIQ	7.47	2	0
glycitein glycitein : A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4'. It has been isolated from the mycelia of the fungus Cordyceps sinensis.	2.05	1	0	7-hydroxyisoflavone; methoxyisoflavone	fungal metabolite; phytoestrogen; plant metabolite
andrographolide [no description available]	2.07	1	0	carbobicyclic compound; gamma-lactone; labdane diterpenoid; primary alcohol; secondary alcohol	anti-HIV agent; anti-inflammatory drug; antineoplastic agent; metabolite
isofraxidin isofraxidin: also see fraxidin	2.03	1	0	hydroxycoumarin
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
icaritin icaritin: structure in first source	2.07	1	0
icariin [no description available]	3.23	5	0	flavonols; glycosyloxyflavone	antioxidant; bone density conservation agent; EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; phytoestrogen
luteolin 4'-o-glucoside luteolin 4'-O-glucoside: from Kummerowia striata. luteolin-4'-O-beta-D-glucopyranoside : A glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl residue at position 4' via a glycosidic linkage. It has been isolated from Olea europaea.	2.05	1	0	beta-D-glucoside; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	plant metabolite
sappanchalcone sappanchalcone: RN given from Toxline; RN not in Chemline 3/85; structure given in first source. sappanchalcone : A member of the class of chalcones that consists of trans-chalcone substituted by hydroxy groups at positions 3, 4 and 4' and a methoxy group at position 2'. Isolated from Caesalpinia sappan, it exhibits neuroprotective and cytoprotective activity.	2.05	1	0	catechols; chalcones; monomethoxybenzene	anti-allergic agent; anti-inflammatory agent; antioxidant; metabolite
neoisoliquiritin neoisoliquiritin: inhibits angiogenesis; isolated from licorice root; isoliquiritin is the (E)-isomer; structure in first source; isoliquiritin is also available	2.25	1	0	flavonoids; glycoside
tiliroside tiliroside: isolated from seeds of Eremocarpus setigerus	2.07	1	0	cinnamate ester; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	plant metabolite
sophoricoside sophoricoside: from fruit of Sophora japonica; structure in first source	2.74	3	0	acrovestone; isoflavonoid
fluvoxamine Fluvoxamine: A selective serotonin reuptake inhibitor that is used in the treatment of DEPRESSION and a variety of ANXIETY DISORDERS.. fluvoxamine : An oxime O-ether that is benzene substituted by a (1E)-N-(2-aminoethoxy)-5-methoxypentanimidoyl group at position 1 and a trifluoromethyl group at position 4. It is a selective serotonin reuptake inhibitor that is used for the treatment of obsessive-compulsive disorder.	2.07	1	0	(trifluoromethyl)benzenes; 5-methoxyvalerophenone O-(2-aminoethyl)oxime	antidepressant; anxiolytic drug; serotonin uptake inhibitor
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	7.57	2	0	carbon group element atom; elemental lead; metal atom	neurotoxin
6,7-dihydroxyflavone 6,7-dihydroxyflavone: intensifies effect of antibiotics on Staphylococcus aureus; structure in first source	2.07	1	0
bay 11-7082 (E)-3-tosylacrylonitrile : A nitrile that is acrylonitrile in which the hydrogen located beta,trans to the cyano group is replaced by a tosyl group. It is an inhibitor of cytokine-induced IkappaB-alpha phosphorylation in cells.	2.31	1	0	nitrile; sulfone	apoptosis inducer; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; non-steroidal anti-inflammatory drug; platelet aggregation inhibitor
(6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid : A dihydroxy monocarboxylic acid that is N-isopropylindole which is substituted at position 3 by a p-fluorophenyl group and at position 2 by a 6-carboxy-3,5-dihydroxyhex-1-en-1-yl group. It has four possible diastereoisomers.	2.07	1	0	dihydroxy monocarboxylic acid; indoles; organofluorine compound
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
levorphanol Levorphanol: A narcotic analgesic that may be habit-forming. It is nearly as effective orally as by injection.	3.1	1	0	morphinane alkaloid
naltrexone Naltrexone: Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.. naltrexone : An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A mu-opioid receptor antagonist, it is used to treat alcohol dependence.	3.1	1	0	cyclopropanes; morphinane-like compound; organic heteropentacyclic compound	antidote to opioid poisoning; central nervous system depressant; environmental contaminant; mu-opioid receptor antagonist; xenobiotic
dextromethorphan Dextromethorphan: Methyl analog of DEXTRORPHAN that shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (RECEPTORS, N-METHYL-D-ASPARTATE) and acts as a non-competitive channel blocker. It is one of the widely used ANTITUSSIVES, and is also used to study the involvement of glutamate receptors in neurotoxicity.. dextromethorphan : A 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the sterocenters at positions 4a, 10 and 10a have S-configuration. It is a prodrug of dextrorphan and used as an antitussive drug for suppressing cough.	2.07	1	0	6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene	antitussive; environmental contaminant; neurotoxin; NMDA receptor antagonist; oneirogen; prodrug; xenobiotic
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.	2.07	1	0	dipeptide	EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
ramipril Ramipril: A long-acting angiotensin-converting enzyme inhibitor. It is a prodrug that is transformed in the liver to its active metabolite ramiprilat.. ramipril : A dipeptide that is the prodrug for ramiprilat, the active metabolite obtained by hydrolysis of the ethyl ester group. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.. quark : Quarks comprise one of two classes of the fundamental particles. Quarks possess fractional electric charges and are not observed in free state. The word "quark" first appears in James Joyce's Finnegans Wake and has been chosen by Murray Gell-Mann as a name for fundamental building blocks of particles.	2.13	1	0	azabicycloalkane; cyclopentapyrrole; dicarboxylic acid monoester; dipeptide; ethyl ester	bradykinin receptor B2 agonist; cardioprotective agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; matrix metalloproteinase inhibitor; prodrug
indinavir sulfate Indinavir: A potent and specific HIV protease inhibitor that appears to have good oral bioavailability.	2.07	1	0	dicarboxylic acid diamide; N-(2-hydroxyethyl)piperazine; piperazinecarboxamide	HIV protease inhibitor
beta-damascenone beta-damascenone: from Ipomoea pes-caprea; RN given refers to cpd without isomeric designation; RN 23726-93-4 refers to beta-damascenone; structure given in first source. beta-damascenone : A cyclic monoterpene ketone that is 2,6,6-trimethylcyclohexa-1,3-diene substituted at position 1 by a crotonoyl group.	2.25	1	0	apo carotenoid monoterpenoid; cyclic monoterpene ketone; enone	fragrance; plant metabolite; volatile oil component
kavain [no description available]	2.07	1	0	racemate	glycine receptor antagonist
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
puerarin [no description available]	2.04	1	0	C-glycosyl compound; isoflavonoid
enalapril Enalapril: An angiotensin-converting enzyme inhibitor that is used to treat HYPERTENSION and HEART FAILURE.. enalapril : A dicarboxylic acid monoester that is ethyl 4-phenylbutanoate in which a hydrogen alpha to the carboxy group is substituted by the amino group of L-alanyl-L-proline (S-configuration).	3.57	2	0	dicarboxylic acid monoester; dipeptide	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; geroprotector; prodrug
vinblastine sulfate [no description available]	2.07	1	0
3,7-dihydroxyflavone 3,7-dihydroxyflavone: structure in first source. 7-hydroxyflavonol : Any flavonol carrying a 7-hydroxy substituent.	2.05	1	0	hydroxyflavan
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
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	3.46	1	1	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite
bleomycin [no description available]	2.07	1	0	bleomycin	antineoplastic agent; metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	7.6	1	0	cysteinium	fundamental metabolite
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	2.03	1	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
normorphine normorphine: RN given refers to (5 alpha,6 alpha)-isomer	3.1	1	0	morphinane alkaloid
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid: chromogen in glucose oxidase-peroxidase method for determining serum glucose; used in free radical scavenging assays; structure in first source	2.4	2	0
gamma-mangostin gamma-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3, 6 and 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antitumour activity.	2.07	1	0	phenols; xanthones	antineoplastic agent; plant metabolite; protein kinase inhibitor
bakuchiol bakuchiol: chief component of Psoralea corylifolia Linn; structure	2.07	1	0
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
bergamottin bergamottin: constituent of bergamot oil; structure given in first source	11.6	10	2	furanocoumarin	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
guajavarin guajavarin: from leaves of Psidium guajava	3.51	1	0
naltrindole benzofuran naltrindole benzofuran: structure given in first source	3.1	1	0	morphinane alkaloid
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
avicularin avicularin: from Polygonum aviculare L.; RN given refers to L-isomer. avicularin : A quercetin O-glycoside in which an alpha-L-arabinofuranosyl residue is attached at position 3 of quercetin via a glycosidic linkage. It is isolated particularly from Juglans regia and Foeniculum vulgare.	2.25	1	0	alpha-L-arabinofuranoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	hepatoprotective agent; plant metabolite
alpinumisoflavone alpinumisoflavone: extract from twigs of poisonous British plant	2.03	1	0	isoflavanones	metabolite
aliskiren aliskiren: orally active nonpeptidic renin inhibitor. aliskiren : A monomethoxybenzene compound having a 3-methoxypropoxy group at the 2-position and a multi-substituted branched alkyl substituent at the 4-position.	3.46	1	1	monocarboxylic acid amide; monomethoxybenzene	antihypertensive agent
z-val-ala-asp(ome)-fluoromethylketone z-Val-Ala-Asp(Ome)-fluoromethylketone: confuse with Z-VAD-FMK. Z-Val-Ala-Asp(OMe)-CH2F : A tripeptide consisting of Z-Val-Ala-Asp(OMe) in which the C-terminal OH group has been replaced by a fluoromethyl group. An irreversible pan-caspase inhibitor.	2.03	1	0	carbamate ester; organofluorine compound; tripeptide	apoptosis inhibitor; protease inhibitor
naltrindole naltrindole: delta opioid receptor antagonist	3.1	1	0	isoquinolines
(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
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
lyoniside daucosterol : A steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa.	2.07	1	0	beta-D-glucoside; monosaccharide derivative; steroid saponin	plant metabolite
quercetin-3'-o-beta-d-glucopyranoside quercetin 3'-O-glucoside: structure in first source	2.13	1	0
c.i. fluorescent brightening agent 28 4,4'-bis({4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino)stilbene-2,2'-disulfonic acid : An organosulfonic acid comprising stilbene having 4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino groups at the 4 and 4'-positions and sulfo groups at the 2- and 2'-positions.	2.25	1	0
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
rifamycin sv rifamycin SV: RN given refers to parent cpd; structure in Merck Index, 9th ed, #8009. rifamycin SV : A member of the class of rifamycins that exhibits antibiotic and antitubercular properties.	2.07	1	0	acetate ester; cyclic ketal; lactam; macrocycle; organic heterotetracyclic compound; polyphenol; rifamycins	antimicrobial agent; antitubercular agent; bacterial metabolite
ginkgolide b [no description available]	2.07	1	0
jatrophone jatrophone: RN refers to (2R-(2R,3aR,9E,12Z))-isomer; structure	2.03	1	0	oxolanes
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
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
2,3,5,4'-tetrahydroxystilbene 2-o-glucopyranoside 2,3,5,4'-tetrahydroxystilbene 2-O-glucopyranoside: isolated from dried root tubers of Polygonum multiflorum; structure in first source	2.07	1	0
6',7'-dihydroxybergamottin 6',7'-dihydroxybergamottin: structure given in first source	10.85	8	1	psoralens
marein marein: hypoglycemic from Coreopsis tinctoria; structure in first source	2.07	1	0	flavonoids; glycoside
trilobatin trilobatin: anti-inflammatory from Lithocarpus polystachyus leaves; structure in first source. trilobatin : An aryl beta-D-glucoside that is phloretin attached to a beta-D-glucopyranosyl residue at position 4' via a glycosidic linkage. It is isolated from the leaves of the Chinese sweet tea Lithocarpus polystachyus and exhibits significant anti-hyperglycemic, anti-oxidative and anti-inflammatory properties.	7.17	1	0	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	anti-inflammatory agent; antioxidant; plant metabolite; sweetening agent
19-hydroxycholesterol 19-hydroxycholesterol: structure given in first source	3.1	1	0	cholestanoid
indigo carmine 3,5-di-O-(E)-caffeoylquinic acid: from roots of Lychnophora ericoides; structure in first source. 3,5-di-O-caffeoyl quinic acid : A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.	2.11	1	0
verlukast verlukast: LTD4 receptor antagonist	2.07	1	0
ceftizoxime [no description available]	3.15	1	0	cephalosporin	antibacterial drug
beta-escin [no description available]	4.26	5	0
borneol [no description available]	3.1	1	0	borneol
nitrofurantoin Nitrofurantoin: A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.. nitrofurantoin : An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.	2.07	1	0	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent
hydroxyachillin hydroxyachillin: isolated from Tanacetum microphyllum; structure given in first source	2.07	1	0	gamma-lactone
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.	2.07	1	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
fumagillin [no description available]	2.07	1	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	2.07	1	0	artemisinin derivative; cyclic acetal; dicarboxylic acid monoester; hemisuccinate; semisynthetic derivative; sesquiterpenoid	antimalarial; antineoplastic agent; ferroptosis inducer
nps2143 [no description available]	3.15	1	0
jwh-133 1,1-dimethylbutyl-1-deoxy-Delta(9)-THC: a CB2 receptor agonists; no further information available on 8/2001. JWH-133 : A dibenzopyran that is Delta(9)-tetrahydrocannabinol which is lacking the hydroxy group and in which the pentyl group at position 3 has been replaced by a 1,1-dimethylbutyl group. A potent and highly selective CB2 receptor agonist.	3.15	1	0	benzochromene; dibenzopyran; organic heterotricyclic compound	analgesic; anti-inflammatory agent; antineoplastic agent; apoptosis inhibitor; CB2 receptor agonist; opioid analgesic; vasodilator agent
relacatib relacatib: a cathepsin K inhibitor; structure in first source	3.15	1	0
anisodamine [no description available]	2.07	1	0
staurosporine staurosporinium : Conjugate acid of staurosporine.	1.99	1	0	ammonium ion derivative
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
mannich bases Mannich Bases: Ketonic amines prepared from the condensation of a ketone with formaldehyde and ammonia or a primary or secondary amine. A Mannich base can act as the equivalent of an alpha,beta unsaturated ketone in synthesis or can be reduced to form physiologically active amino alcohols.	2.17	1	0
formazans Formazans: Colored azo compounds formed by the reduction of tetrazolium salts. Employing this reaction, oxidoreductase activity can be determined quantitatively in tissue sections by allowing the enzymes to act on their specific substrates in the presence of tetrazolium salts.	2.03	1	0
fosinopril [no description available]	3.15	1	0
ono4819 ONO4819: prostanoid receptor EP4 agonist	3.15	1	0	benzyl ether
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.	3.57	2	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
mk-0429 [no description available]	3.15	1	0
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).	2.78	3	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
ginsenoside rb1 [no description available]	2.07	1	0	ginsenoside; glycoside; tetracyclic triterpenoid	anti-inflammatory drug; anti-obesity agent; apoptosis inhibitor; neuroprotective agent; plant metabolite; radical scavenger
bn 52020 [no description available]	2.07	1	0
prunin protein, prunus naringenin-7-O-glucoside: from Dracocephalum rupestre; has protective effects against doxorubicin-induced apoptosis	2.13	1	0
norcodeine norcodeine: RN given refers to (5 alpha,6 alpha)-isomer. norcodeine : A morphinane-like compound that is the N-demethylated derivative of codeine.	3.1	1	0	morphinane alkaloid
zeolites [no description available]	2.41	1	0
epoxybergamottin epoxybergamottin: from grapefruit peel; structure in first source	2.95	1	0	psoralens
4-hydroxyestrone 4-hydroxyestrone : A 4-hydroxy steroid that is estrone substituted by a hydroxy group at position 4.	3.1	1	0	17-oxo steroid; 3-hydroxy steroid; 4-hydroxy steroid; catechols; phenolic steroid	carcinogenic agent; estrogen; human urinary metabolite
abyssinone ii abyssinone II: chemopreventive agent from Broussonetia papypera; structure in first source	2.04	1	0
odanacatib odanacatib: a selective inhibitor of cathepsin K for the treatment of post-menopausal osteoporosis; structure in first source	3.15	1	0
balicatib balicatib: cathepsin K inhibitor	3.15	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
11 beta-hydroxyandrosterone 11 beta-hydroxyandrosterone: RN given refers to (3alpha,5alpha,11beta)-isomer; structure	3.1	1	0	3-hydroxy steroid	androgen
saracatinib [no description available]	3.15	1	0	aromatic ether; benzodioxoles; diether; N-methylpiperazine; organochlorine compound; oxanes; quinazolines; secondary amino compound	anticoronaviral agent; antineoplastic agent; apoptosis inducer; autophagy inducer; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; radiosensitizing agent
ko 143 [no description available]	2.07	1	0	beta-carbolines; tert-butyl ester
2-hydroxyestriol 2-hydroxyestriol: structure	3.1	1	0
bavachinin bavachinin: do not confuse with bavachin	2.07	1	0	flavanones
ribose ribopyranose : The pyranose form of ribose.	7.41	1	0	D-ribose; ribopyranose
acebutolol alpha-D-glucosyl-(1->4)-alpha-D-mannose : An alpha-D-glucosyl-(1->4)-D-mannopyranose in which the anomeric hydroxy group has alpha configuration.	2.05	1	0	alpha-D-glucosyl-(1->4)-D-mannopyranose
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
malvidin-3-glucoside oenin: pigment found in red wine	2.05	1	0
procyanidin b1 procyanidin B1 : A proanthocyanidin consisting of (-)-epicatechin and (+)-catechin units joined by a bond between positions 4 and 8' respectively in a beta-configuration.. Procyanidin B1 can be found in Cinnamomum verum (Ceylon cinnamon, in the rind, bark or cortex), in Uncaria guianensis (cat's claw, in the root), and in Vitis vinifera (common grape vine, in the leaf) or in peach.	2.05	1	0	biflavonoid; hydroxyflavan; polyphenol; proanthocyanidin	anti-inflammatory agent; EC 3.4.21.5 (thrombin) inhibitor; metabolite
nystatin a1 Nystatin: Macrolide antifungal antibiotic complex produced by Streptomyces noursei, S. aureus, and other Streptomyces species. The biologically active components of the complex are nystatin A1, A2, and A3.. nystatin : A heterogeneous mixture of polyene compounds produced by cultures of Streptomyces noursei. It mainly consists of three biologically active components designated nystatin A1, nystatin A2, and nystatin A3. It is used to treat oral and dermal fungal infections.. nystatin A1 : A polyene macrolide antibiotic; part of the nystatin complex produced by several Streptomyces species. It is an antifungal antibiotic used for the treatment of topical fungal infections caused by a broad spectrum of fungal pathogens comprising yeast-like and filamentous species.	2.07	1	0	nystatins
Dihydrotanshinone I dihydrotanshinone I: extracted from Radix Salviae	2.07	1	0	abietane diterpenoid	anticoronaviral agent
N-methyl-N-[2-[[[2-[(2-oxo-1,3-dihydroindol-5-yl)amino]-5-(trifluoromethyl)-4-pyrimidinyl]amino]methyl]phenyl]methanesulfonamide [no description available]	3.15	1	0	sulfonamide
pf-562,271 [no description available]	3.15	1	0	indoles
2-(n-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose 2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose: fluorescent probe for glucose uptake activity in E coli; structure given in first source	2.31	1	0
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.	2.07	1	0	benzoxazole
sepharose agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.	2.76	2	0
cinobufagin cinobufagin: isolated from Chinese medicinal preparation ch'an su; derived from toad venom	2.07	1	0	steroid lactone
verproside verproside: from Pseudolysimachion longifolium; structure in first source	2.07	1	0	glycoside	metabolite
minecoside [no description available]	2.07	1	0	hydroxycinnamic acid	metabolite
(R)-(+)-6',7'-dihydroxybergamottin [no description available]	3.79	2	1	furanocoumarin	metabolite
atropine sulfate [no description available]	2.07	1	0
nomilin [no description available]	2.5	2	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
sudachitin sudachitin: antimicrobial from the peels of Citrus sudachi; structure in first source	3.35	1	0	ether; flavonoids
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	2.77	3	0
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
prim-o-glucosylcimifugin prim-O-glucosylcimifugin: from Peucedanum dissolutum; structure in first source	2.07	1	0	organic heterotricyclic compound; oxacycle
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	1	0
fortunellin fortunellin: from Mentha piperita; structure in first source	2.07	1	0
amodiaquine hydrochloride [no description available]	2.48	2	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.	2.57	2	0
teriparatide [no description available]	3.15	1	0	polypeptide
tannins Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.	3.1	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.	2.07	1	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	3.07	4	0	glycoside
endothelin-1 Endothelin-1: A 21-amino acid peptide produced in a variety of tissues including endothelial and vascular smooth-muscle cells, neurons and astrocytes in the central nervous system, and endometrial cells. It acts as a modulator of vasomotor tone, cell proliferation, and hormone production. (N Eng J Med 1995;333(6):356-63)	2.25	1	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.17	1	0	1,2-diacyl-sn-glycero-3-phosphocholine
WAY-316606 WAY-316606 : A sulfonamide resulting from the formal condensation of the sulfonic acid group of 5-(phenylsulfonyl)-2-(trifluoromethyl)benzenesulfonic acid with the primary amino group of piperidin-4-amine. An inhibitor of secreted Frizzled-Related Protein-1 (sFRP-1).	3.15	1	0	(trifluoromethyl)benzenes; piperidines; secondary amino compound; sulfonamide; sulfone	secreted frizzled-related protein 1 inhibitor
didymin didymin: a dietary glycoside from citrus fruits that induces Fas-mediated apoptotic pathway in human non-small-cell lung cancer cells in vitro and in vivo; structure in first source	3.63	2	0	flavonoids; glycoside
dihydrorobinetin dihydrorobinetin: structure in first source	2.07	1	0
chitosan [no description available]	3.23	5	0
bucladesine Bucladesine: A cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed). bucladesine : A 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP.	2.01	1	0	3',5'-cyclic purine nucleotide
taurocholic acid, monosodium salt [no description available]	3.54	2	0	bile salt
monensin [no description available]	2.07	1	0
s-adenosylmethionine (R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.	2.01	1	0	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
vel-0230 VEL-0230: a cathepsin K antagonist	3.15	1	0
prunin prunin: structure in first source	8.21	5	0
piperidines Piperidines: A family of hexahydropyridines.	3.19	1	0
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.	3.21	5	0
gypenoside XVII gypenoside XVII : 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 groups at positions 3 and 20 have been converted to the corresponding beta-D-glucopyranoside and beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside respectively, and in which a double bond has been introduced at the 24-25 position.	2.07	1	0	12beta-hydroxy steroid; beta-D-glucoside; disaccharide derivative; ginsenoside; tetracyclic triterpenoid	plant metabolite
isoquercitrin [no description available]	2.13	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.	3.93	12	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
novobiocin Novobiocin: An antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189). novobiocin : A coumarin-derived antibiotic obtained from Streptomyces niveus.	4.34	3	0	carbamate ester; ether; hexoside; hydroxycoumarin; monocarboxylic acid amide; monosaccharide derivative; phenols	antibacterial agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Escherichia coli metabolite; hepatoprotective 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.	8.85	3	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.	2.07	1	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]	2.07	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
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.	3.68	9	0	benzenes; hydroxycoumarin; methyl ketone
rk 682 [no description available]	2.46	2	0
6-o-palmitoylascorbic acid [no description available]	2.41	2	0	fatty acid ester
citrinin Citrinin: Antibiotic and mycotoxin from Aspergillus niveus and Penicillium citrinum.	2.07	1	0
tipranavir tipranavir: inhibits HIV-1 protease. tipranavir : A pyridine-2-sulfonamide substituted at C-5 by a trifluoromethyl group and at the sulfonamide nitrogen by a dihydropyrone-containing m-tolyl substituent. It is an HIV-1 protease inhibitor.	2.07	1	0	sulfonamide	antiviral drug; HIV protease inhibitor
4-hydroxycoumarin 2-hydroxychromone: structure	3.1	1	0	hydroxycoumarin
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
nickel nitrilotriacetic acid [no description available]	2.11	1	0
epidermal growth factor Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.	2.07	1	0
microcystin microcystin: microcystins have the general structure cyclo(D-Ala-L-X-D-erythro--methylisoasp-L-Y-Adda-D-isoGlu-N-methyldehydroAla) where X and Y are variable L-amino acids;. microcystin : A family of cyclic heptapeptide hepatotoxins produced by a number of cyanobacteria, the most notable of which is Microcystis, from which the name of the family is derived. Microcystins consist of a heptapeptide macrocycle made up of five non-protein amino acids and two protein amino acids.	7.73	3	0	peptide
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.	3.38	6	0
phytoestrogens Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.	2.08	1	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.	3.25	6	0	ketal
ajmaline [no description available]	2.07	1	0
thearubigin thearubigin: from black tea leaves; a catechin oxidized product; a mixture of heterogenous polyphenols	2.03	1	0
g(m3) ganglioside G(M3) Ganglioside: A ganglioside present in abnormally large amounts in the brain and liver due to a deficient biosynthetic enzyme, G(M3):UDP-N-acetylgalactosaminyltransferase. Deficiency of this enzyme prevents the formation of G(M2) ganglioside from G(M3) ganglioside and is the cause of an anabolic sphingolipidosis.. alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/24:1(15Z)) : A sialotriaosylceramide consisting of beta-D-GalNAc-(1->4)-[alpha-Neu5Ac-(2->3)]-beta-D-Gal-(1->4)-beta-D-Glc attached to the primary hydroxy function of ceramide(d18:1/24:1(15Z)).	2.13	1	0	alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-ceramide; sialodiosylceramide; sialotriaosylceramide	mouse metabolite
angiotensin i Angiotensin I: A decapeptide that is cleaved from precursor angiotensinogen by RENIN. Angiotensin I has limited biological activity. It is converted to angiotensin II, a potent vasoconstrictor, after the removal of two amino acids at the C-terminal by ANGIOTENSIN CONVERTING ENZYME.. angiotensin I : A ten amino acid peptide formed by renin cleavage of angiotensinogen. Angiotensin I has no direct biological function except that high levels can stimulate catecholamine production. It is metabolized to its biologically active byproduct angiotensin II, a potent vasoconstrictor, by angiotensin converting enzyme (ACE) through cleavage of the two terminal amino acids.. angiotensin I dizwitterion : A peptide zwitterion that is the dizwitterionic form of angiotensin I having both carboxy groups deprotonated and the aspartyl amino group and arginine side-chain protonated. It is the major species at pH 7.3.	2.1	1	0	angiotensin; peptide zwitterion	human metabolite; neurotransmitter agent
oridonin [no description available]	7.11	1	0
peoniflorin peoniflorin: from Radix and of Paeonia suffruticosa	3.88	11	0
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).	8.11	5	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.	2.73	3	0
lactoferrin Lactoferrin: An iron-binding protein that was originally characterized as a milk protein. It is widely distributed in secretory fluids and is found in the neutrophilic granules of LEUKOCYTES. The N-terminal part of lactoferrin possesses a serine protease which functions to inactivate the TYPE III SECRETION SYSTEM used by bacteria to export virulence proteins for host cell invasion.	7.21	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.	2.13	1	0
neohesperidin [no description available]	5.75	24	0
poncirin poncirin: isolated from the fructus of Poncirus trifoliata; structure in first source	4.48	6	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.	3.57	2	0	2-aminopurines; oxopurine	antimetabolite; antiviral drug
cyclic gmp Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.	3.51	2	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
deoxyguanosine [no description available]	2.07	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanine [no description available]	2.44	2	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; 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.	7.21	1	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
3-methyladenine N3-methyladenine: structure in first source	2.15	1	0
7-methylguanine 7-methylguanine: RN given refers to unlabeled cpd; structure. 7-methylguanine : A methylguanine that is guanine substituted by a methyl group at position 7. It is a metabolite obtained during the methylation of DNA.. 2-imino-7-methyl-1,2,3,7-tetrahydro-6H-purin-6-one : A 7-methylguanine that is 1,2,3,7-tetrahydro-6H-purin-6-one substituted by an imino group at position 2 and a methyl group at position 7.. 2-amino-7-methyl-7H-purin-6-ol : A 7-methylguanine that is 7H-purine substituted by an amino group at position 2, a methyl group at position 7 and a hydroxy group at position 6.. 2-amino-7-methyl-1,7-dihydro-6H-purin-6-one : A 7-methylguanine that is 1,7-dihydro-6H-purin-6-one substituted by an amino group at position 2 and a methyl group at position 7.	2.03	1	0	7-methylguanine
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)	4.57	4	0	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.	8.88	3	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
valacyclovir Valacyclovir: A prodrug of acyclovir that is used in the treatment of HERPES ZOSTER and HERPES SIMPLEX VIRUS INFECTION of the skin and mucous membranes, including GENITAL HERPES.	3.57	2	0	L-valyl ester	antiviral drug
sildenafil sildenafil : A pyrazolo[4,3-d]pyrimidin-7-one having a methyl substituent at the 1-position, a propyl substituent at the 3-position and a 2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl group at the 5-position.	2.07	1	0	piperazines; pyrazolopyrimidine; sulfonamide	EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; vasodilator agent
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.	2.43	2	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
norclozapine norclozapine: structure given in first source. N-desmethylclozapine : A dibenzodoazepine substituted with chloro and piperazino groups which is a major metabolite of clozapine; a potent and selective 5-HT2C serotonin receptor antagonist.	3.1	1	0	dibenzodiazepine; organochlorine compound; piperazines	delta-opioid receptor agonist; metabolite; serotonergic antagonist
hesperadin [no description available]	2.02	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.	2.07	1	0	guanosines	biomarker
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.	2.03	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.	7.57	2	0

Condition	Relationship Strength	Studies	Trials
Bilirubinemia [description not available]	2.92	1	0
Benign Neoplasms [description not available]	5.08	6	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.	5.08	6	0
Bone Loss, Osteoclastic [description not available]	4.26	6	0
Age-Related Osteoporosis [description not available]	6.13	19	0
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	6.13	19	0
Innate Inflammatory Response [description not available]	7.67	31	1
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.	7.67	31	1
Anemia, Fanconi [description not available]	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)	2.13	1	0
Atherogenesis [description not available]	4.54	8	0
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	4.54	8	0
Carcinoma, Anaplastic [description not available]	2.31	1	0
Cancer of Stomach [description not available]	3.16	4	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	7.31	1	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	3.16	4	0
Injury, Ischemia-Reperfusion [description not available]	4.22	15	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.	4.22	15	0
Elevated Cholesterol [description not available]	6.41	8	2
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.	11.41	8	2
Cancer of Ovary [description not available]	3.07	3	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.	3.07	3	0
Hepatocellular Carcinoma [description not available]	3.23	5	0
Cancer of Liver [description not available]	3.11	4	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.	3.23	5	0
Liver Neoplasms Tumors or cancer of the LIVER.	3.11	4	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.	4.18	5	0
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.	4.18	5	0
Cancer of Esophagus [description not available]	2.69	2	0
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	2.69	2	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.	2.9	2	0
Cancer of Colon [description not available]	3.18	5	0
Colonic Neoplasms Tumors or cancer of the COLON.	3.18	5	0
Cancer of Cervix [description not available]	3.07	4	0
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	3.07	4	0
Acute Liver Injury, Drug-Induced [description not available]	5.2	15	0
Chemical and Drug Induced Liver Injury, Chronic Liver disease lasting six months or more, caused by an adverse effect of a drug or chemical. The adverse effect may be caused by drugs, drug metabolites, chemicals from the environment, or an idiosyncratic response.	3.57	5	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.	5.2	15	0
Degenerative Disc Disease [description not available]	2.9	3	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	6.91	58	1
Intervertebral Disc Degeneration Degenerative changes in the INTERVERTEBRAL DISC due to aging or structural damage, especially to the vertebral end-plates.	2.9	3	0
Dyslipidemia [description not available]	7.55	2	0
Liver Steatosis [description not available]	7.86	3	0
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.	2.86	3	0
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.	2.55	2	0
Cardiovascular Stroke [description not available]	3.43	7	0
Injury, Myocardial Reperfusion [description not available]	2.9	3	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	3.43	7	0
Cancer of Lung [description not available]	2.47	2	0
Lung Neoplasms Tumors or cancer of the LUNG.	2.47	2	0
Cirrhosis [description not available]	3.43	5	0
Dermatoses [description not available]	2.41	1	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	3.43	5	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	2.41	1	0
Airflow Obstruction, Chronic [description not available]	3.78	3	0
Pulmonary Disease, Chronic Obstructive A disease of chronic diffuse irreversible airflow obstruction. Subcategories of COPD include CHRONIC BRONCHITIS and PULMONARY EMPHYSEMA.	3.78	3	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	9.4	19	0
Peripheral Nerve Diseases [description not available]	2.41	1	0
Peripheral Nervous System Diseases Diseases of the peripheral nerves external to the brain and spinal cord, which includes diseases of the nerve roots, ganglia, plexi, autonomic nerves, sensory nerves, and motor nerves.	2.41	1	0
Cirrhosis, Liver [description not available]	3.17	4	0
Liver Dysfunction [description not available]	2.47	2	0
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	3.17	4	0
Liver Diseases Pathological processes of the LIVER.	2.47	2	0
Colitis Gravis [description not available]	2.94	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.	2.94	3	0
Insulin Sensitivity [description not available]	6.27	6	2
Atrophy, Muscle [description not available]	2.41	1	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.	6.27	6	2
Muscular Atrophy Derangement in size and number of muscle fibers occurring with aging, reduction in blood supply, or following immobilization, prolonged weightlessness, malnutrition, and particularly in denervation.	2.41	1	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).	11.05	9	1
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	8.73	8	0
Blood Pressure, High [description not available]	3.54	6	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.	3.54	6	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	3.74	9	0
Acute Confusional Senile Dementia [description not available]	3.4	6	0
Age-Related Memory Disorders [description not available]	4.91	7	1
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)	3.4	6	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.	4.91	7	1
Hyperlipemia [description not available]	2.9	2	0
Hyperlipidemias Conditions with excess LIPIDS in the blood.	2.9	2	0
Alveolitis, Fibrosing [description not available]	2.85	3	0
Pulmonary Fibrosis A process in which normal lung tissues are progressively replaced by FIBROBLASTS and COLLAGEN causing an irreversible loss of the ability to transfer oxygen into the bloodstream via PULMONARY ALVEOLI. Patients show progressive DYSPNEA finally resulting in death.	2.85	3	0
Cardiac Toxicity [description not available]	8.12	4	0
Cardiotoxicity Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.	3.12	4	0
Diabetic Feet [description not available]	2.59	2	0
Diabetic Foot Common foot problems in persons with DIABETES MELLITUS, caused by any combination of factors such as DIABETIC NEUROPATHIES; PERIPHERAL VASCULAR DISEASES; and INFECTION. With the loss of sensation and poor circulation, injuries and infections often lead to severe foot ulceration, GANGRENE and AMPUTATION.	7.59	2	0
Acute Myelogenous Leukemia [description not available]	2.6	1	0
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	2.6	1	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	7.72	2	0
Aerobic Glycolysis, Oncologic [description not available]	2.6	1	0
Alloxan Diabetes [description not available]	4.56	22	0
Diabetic Glomerulosclerosis [description not available]	3.1	4	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.	3.1	4	0
Blood Poisoning [description not available]	3.45	6	0
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	3.45	6	0
Epithelial Ovarian Cancer [description not available]	7.6	1	0
Carcinoma, Ovarian Epithelial A malignant neoplasm that originates in cells on the surface EPITHELIUM of the ovary and is the most common form of ovarian cancer. There are five histologic subtypes: papillary serous, endometrioid, mucinous, clear cell, and transitional cell. Mutations in BRCA1, OPCML, PRKN, PIK3CA, AKT1, CTNNB1, RRAS2, and CDH1 genes are associated with this cancer.	2.6	1	0
Colorectal Cancer [description not available]	7.88	3	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.	2.88	3	0
Blood Clot [description not available]	2.6	1	0
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	7.6	1	0
Aseptic Necrosis of Bone [description not available]	2.6	1	0
Osteonecrosis Death of a bone or part of a bone, either atraumatic or posttraumatic.	7.6	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)	2.6	1	0
Injuries, Spinal Cord [description not available]	2.57	2	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.).	2.57	2	0
Hyperpotassemia [description not available]	2.6	1	0
Hyperkalemia Abnormally high potassium concentration in the blood, most often due to defective renal excretion. It is characterized clinically by electrocardiographic abnormalities (elevated T waves and depressed P waves, and eventually by atrial asystole). In severe cases, weakness and flaccid paralysis may occur. (Dorland, 27th ed)	2.6	1	0
Bacterial Pneumonia [description not available]	2.6	1	0
Pneumonia, Bacterial Inflammation of the lung parenchyma that is caused by bacterial infections.	2.6	1	0
Peripheral Nerve Injury [description not available]	2.21	1	0
Peripheral Nerve Injuries Injuries to the PERIPHERAL NERVES.	2.21	1	0
Acute Kidney Failure [description not available]	2.47	2	0
Heart Disease, Ischemic [description not available]	2.21	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).	2.21	1	0
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	2.47	2	0
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.69	2	0
Anterior Choroidal Artery Infarction [description not available]	2.25	1	0
Cerebral Ischemia [description not available]	7.9	3	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).	7.25	1	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.	2.9	3	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.	2.69	2	0
Autosomal Dominant Juvenile Parkinson Disease [description not available]	2.25	1	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.	2.25	1	0
Chondrodystrophic Myotonia [description not available]	2.25	1	0
Poultry Diseases Diseases of birds which are raised as a source of meat or eggs for human consumption and are usually found in barnyards, hatcheries, etc. The concept is differentiated from BIRD DISEASES which is for diseases of birds not considered poultry and usually found in zoos, parks, and the wild.	2.25	1	0
Infections, Pseudomonas [description not available]	2.25	1	0
Pseudomonas Infections Infections with bacteria of the genus PSEUDOMONAS.	2.25	1	0
Cognitive Decline [description not available]	3.83	3	0
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	8.83	3	0
Respiration Disorders Diseases of the respiratory system in general or unspecified or for a specific respiratory disease not available.	3.17	1	0
Dementia Praecox [description not available]	2.25	1	0
Schizophrenia A severe emotional disorder of psychotic depth characteristically marked by a retreat from reality with delusion formation, HALLUCINATIONS, emotional disharmony, and regressive behavior.	2.25	1	0
Osteogenic Sarcoma [description not available]	2.8	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)	2.8	3	0
Experimental Hepatoma [description not available]	2.25	1	0
Diabetes Mellitus, Adult-Onset [description not available]	4.4	7	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.	4.4	7	0
Osteolysis Dissolution of bone that particularly involves the removal or loss of calcium.	3.37	6	0
Astrocytoma, Grade IV [description not available]	3.07	4	0
Angiogenesis, Pathologic [description not available]	2.59	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.	3.07	4	0
Skin Aging The process of aging due to changes in the structure and elasticity of the skin over time. It may be a part of physiological aging or it may be due to the effects of ultraviolet radiation, usually through exposure to sunlight.	2.25	1	0
Encephalopathy, Toxic [description not available]	4.21	3	1
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	3.46	2	0
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	3.45	2	0
Cancer of Prostate [description not available]	2.41	1	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.41	1	0
Prosthesis Durability [description not available]	2.25	1	0
Intestinal Diseases Pathological processes in any segment of the INTESTINE from DUODENUM to RECTUM.	2.31	1	0
Abnormal Movements [description not available]	2.31	1	0
Tardive Dystonia [description not available]	2.31	1	0
Tardive Dyskinesia Drug-related movement disorder characterized by uncontrollable movements in certain muscles. It is associated with a long-term exposure to certain neuroleptic medications (e.g., METOCLOPRAMIDE).	7.31	1	0
Agranulocytosis A decrease in the number of GRANULOCYTES; (BASOPHILS; EOSINOPHILS; and NEUTROPHILS).	7.31	1	0
Weight Gain Increase in BODY WEIGHT over existing weight.	7.72	3	0
Asthma, Bronchial [description not available]	3.08	4	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).	3.08	4	0
2019 Novel Coronavirus Disease [description not available]	3.23	1	0
Colitis, Mucous [description not available]	2.66	2	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.	7.66	2	0
Fatty Liver, Nonalcoholic [description not available]	2.31	1	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	2.31	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.	7.72	2	0
Delayed Effects, Prenatal Exposure [description not available]	2.31	1	0
Burns Injuries to tissues caused by contact with heat, steam, chemicals (BURNS, CHEMICAL), electricity (BURNS, ELECTRIC), or the like.	2.41	1	0
Bone Diseases Diseases of BONES.	4.24	3	0
Brain Hemorrhage, Cerebral [description not available]	2.15	1	0
Allodynia [description not available]	2.15	1	0
Cerebral Hemorrhage Bleeding into one or both CEREBRAL HEMISPHERES including the BASAL GANGLIA and the CEREBRAL CORTEX. It is often associated with HYPERTENSION and CRANIOCEREBRAL TRAUMA.	7.15	1	0
Arthritis, Degenerative [description not available]	2.54	2	0
Ache [description not available]	2.15	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.	2.54	2	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	7.15	1	0
Nervous System Disorders [description not available]	3.97	2	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.	3.97	2	0
Hyperammonemia Elevated level of AMMONIA in the blood. It is a sign of defective CATABOLISM of AMINO ACIDS or ammonia to UREA.	2.15	1	0
Breast Cancer [description not available]	7.83	3	0
Breast Neoplasms Tumors or cancer of the human BREAST.	2.83	3	0
Impaired Glucose Tolerance [description not available]	2.54	2	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.	2.54	2	0
Complications of Diabetes Mellitus [description not available]	2.17	1	0
Autoimmune Diabetes [description not available]	3.36	6	0
Diabetes Mellitus, Type 1 A subtype of DIABETES MELLITUS that is characterized by INSULIN deficiency. It is manifested by the sudden onset of severe HYPERGLYCEMIA, rapid progression to DIABETIC KETOACIDOSIS, and DEATH unless treated with insulin. The disease may occur at any age, but is most common in childhood or adolescence.	3.36	6	0
Dermatitis Any inflammation of the skin.	2.17	1	0
Aseptic Necrosis of Femur Head [description not available]	2.17	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.	8.56	1	1
Ulcer A lesion on the surface of the skin or a mucous surface, produced by the sloughing of inflammatory necrotic tissue.	7.17	1	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	5.66	6	1
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	10.66	6	1
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	2.55	2	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.	2.17	1	0
Diabetic Cardiomyopathies Diabetes complications in which VENTRICULAR REMODELING in the absence of CORONARY ATHEROSCLEROSIS and hypertension results in cardiac dysfunctions, typically LEFT VENTRICULAR DYSFUNCTION. The changes also result in myocardial hypertrophy, myocardial necrosis and fibrosis, and collagen deposition due to impaired glucose tolerance.	2.17	1	0
Constriction, Pathological [description not available]	2.17	1	0
Constriction, Pathologic The condition of an anatomical structure's being constricted beyond normal dimensions.	2.17	1	0
Anasarca [description not available]	2.68	3	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.68	3	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)	3.84	11	0
Bowel Diseases, Inflammatory [description not available]	2.17	1	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.	2.17	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.	2.55	2	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.	2.55	2	0
Chronic Lung Injury [description not available]	2.17	1	0
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	2.8	3	0
Pneumonia Infection of the lung often accompanied by inflammation.	2.8	3	0
Cicatrix, Hypertrophic An elevated scar, resembling a KELOID, but which does not spread into surrounding tissues. It is formed by enlargement and overgrowth of cicatricial tissue and regresses spontaneously.	2.17	1	0
Alcoholic Liver Diseases [description not available]	2.21	1	0
Alcoholic Fatty Liver [description not available]	2.21	1	0
Liver Diseases, Alcoholic Liver diseases associated with ALCOHOLISM. It usually refers to the coexistence of two or more subentities, i.e., ALCOHOLIC FATTY LIVER; ALCOHOLIC HEPATITIS; and ALCOHOLIC CIRRHOSIS.	2.21	1	0
Absence Seizure [description not available]	2.53	2	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.	7.53	2	0
ALS - Amyotrophic Lateral Sclerosis [description not available]	2.21	1	0
Amyotrophic Lateral Sclerosis A degenerative disorder affecting upper MOTOR NEURONS in the brain and lower motor neurons in the brain stem and SPINAL CORD. Disease onset is usually after the age of 50 and the process is usually fatal within 3 to 6 years. Clinical manifestations include progressive weakness, atrophy, FASCICULATION, hyperreflexia, DYSARTHRIA, dysphagia, and eventual paralysis of respiratory function. Pathologic features include the replacement of motor neurons with fibrous ASTROCYTES and atrophy of anterior SPINAL NERVE ROOTS and corticospinal tracts. (From Adams et al., Principles of Neurology, 6th ed, pp1089-94)	2.21	1	0
Bone Cancer [description not available]	2.53	2	0
Experimental Neoplasms [description not available]	2.37	2	0
Invasiveness, Neoplasm [description not available]	2.82	3	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	2.53	2	0
Abscess, Amebic [description not available]	2.21	1	0
E coli Infections [description not available]	2.21	1	0
Infections, Staphylococcal [description not available]	2.21	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.	2.21	1	0
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	2.21	1	0
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	2.21	1	0
Prediabetes [description not available]	4.51	1	1
Prediabetic State The time period before the development of symptomatic diabetes. For example, certain risk factors can be observed in subjects who subsequently develop INSULIN RESISTANCE as in type 2 diabetes (DIABETES MELLITUS, TYPE 2).	4.51	1	1
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	2.21	1	0
Palmoplantaris Pustulosis [description not available]	2.21	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.	7.21	1	0
Left Ventricular Dysfunction [description not available]	2.21	1	0
Cardiomyopathies, Primary [description not available]	2.57	2	0
Cardiomyopathies A group of diseases in which the dominant feature is the involvement of the CARDIAC MUSCLE itself. Cardiomyopathies are classified according to their predominant pathophysiological features (DILATED CARDIOMYOPATHY; HYPERTROPHIC CARDIOMYOPATHY; RESTRICTIVE CARDIOMYOPATHY) or their etiological/pathological factors (CARDIOMYOPATHY, ALCOHOLIC; ENDOCARDIAL FIBROELASTOSIS).	2.57	2	0
Ventricular Dysfunction, Left A condition in which the LEFT VENTRICLE of the heart was functionally impaired. This condition usually leads to HEART FAILURE; MYOCARDIAL INFARCTION; and other cardiovascular complications. Diagnosis is made by measuring the diminished ejection fraction and a depressed level of motility of the left ventricular wall.	2.21	1	0
Lung Injury, Acute [description not available]	2.77	3	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).	2.77	3	0
Extravascular Hemolysis [description not available]	2.1	1	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.1	1	0
Acute Necrotizing Pancreatitis [description not available]	2.47	2	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.08	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.	2.08	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.	2.78	3	0
Condition, Preneoplastic [description not available]	2.1	1	0
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	2.1	1	0
Disease Exacerbation [description not available]	2.1	1	0
Polyarthritis [description not available]	2.1	1	0
Autoimmune Disease [description not available]	2.1	1	0
Arthritis Acute or chronic inflammation of JOINTS.	7.1	1	0
Autoimmune Diseases Disorders that are characterized by the production of antibodies that react with host tissues or immune effector cells that are autoreactive to endogenous peptides.	2.1	1	0
Acute Brain Injuries [description not available]	2.78	3	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.	2.78	3	0
Idiopathic Parkinson Disease [description not available]	2.52	2	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)	2.52	2	0
Chondrosarcoma A slowly growing malignant neoplasm derived from cartilage cells, occurring most frequently in pelvic bones or near the ends of long bones, in middle-aged and old people. Most chondrosarcomas arise de novo, but some may develop in a preexisting benign cartilaginous lesion or in patients with ENCHONDROMATOSIS. (Stedman, 25th ed)	7.1	1	0
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2.1	1	0
Demineralization, Tooth [description not available]	2.1	1	0
Pleurisy INFLAMMATION of PLEURA, the lining of the LUNG. When PARIETAL PLEURA is involved, there is pleuritic CHEST PAIN.	2.11	1	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	2.1	1	0
Hyperthyroid [description not available]	7.1	1	0
Hyperthyroidism Hypersecretion of THYROID HORMONES from the THYROID GLAND. Elevated levels of thyroid hormones increase BASAL METABOLIC RATE.	2.1	1	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	3.33	6	0
Encephalopathy, Hepatic [description not available]	2.1	1	0
Hepatic Encephalopathy A syndrome characterized by central nervous system dysfunction in association with LIVER FAILURE, including portal-systemic shunts. Clinical features include lethargy and CONFUSION (frequently progressing to COMA); ASTERIXIS; NYSTAGMUS, PATHOLOGIC; brisk oculovestibular reflexes; decorticate and decerebrate posturing; MUSCLE SPASTICITY; and bilateral extensor plantar reflexes (see REFLEX, BABINSKI). ELECTROENCEPHALOGRAPHY may demonstrate triphasic waves. (From Adams et al., Principles of Neurology, 6th ed, pp1117-20; Plum & Posner, Diagnosis of Stupor and Coma, 3rd ed, p222-5)	7.1	1	0
Anoxemia [description not available]	2.11	1	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	2.11	1	0
Chromosome-Defective Micronuclei [description not available]	2.72	3	0
Brain Inflammation [description not available]	2.49	2	0
Encephalitis Inflammation of the BRAIN due to infection, autoimmune processes, toxins, and other conditions. Viral infections (see ENCEPHALITIS, VIRAL) are a relatively frequent cause of this condition.	2.49	2	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.	2.11	1	0
Caries, Cervical [description not available]	2.13	1	0
Malignant Melanoma [description not available]	2.13	1	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)	2.13	1	0
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.	2.44	2	0
Cancer of Intestines [description not available]	2.13	1	0
Intestinal Neoplasms Tumors or cancer of the INTESTINES.	2.13	1	0
Intestinal Polyps Discrete abnormal tissue masses that protrude into the lumen of the INTESTINE. A polyp is attached to the intestinal wall either by a stalk, pedunculus, or by a broad base.	2.13	1	0
Metastase [description not available]	2.13	1	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.13	1	0
Eosinophilia, Tropical [description not available]	2.13	1	0
Eosinophilia Abnormal increase of EOSINOPHILS in the blood, tissues or organs.	2.13	1	0
Benign Psychomotor Epilepsy, Childhood [description not available]	3.45	2	0
Epilepsy, Temporal Lobe A localization-related (focal) form of epilepsy characterized by recurrent seizures that arise from foci within the TEMPORAL LOBE, most commonly from its mesial aspect. A wide variety of psychic phenomena may be associated, including illusions, hallucinations, dyscognitive states, and affective experiences. The majority of complex partial seizures (see EPILEPSY, COMPLEX PARTIAL) originate from the temporal lobes. Temporal lobe seizures may be classified by etiology as cryptogenic, familial, or symptomatic. (From Adams et al., Principles of Neurology, 6th ed, p321).	3.45	2	0
Acetonemia [description not available]	2.13	1	0
Complication, Postoperative [description not available]	2.13	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.	2.13	1	0
Benign Neoplasms, Brain [description not available]	2.15	1	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.	2.15	1	0
Academic Disorder, Developmental [description not available]	2.53	2	0
Learning Disabilities Conditions characterized by a significant discrepancy between an individual's perceived level of intellect and their ability to acquire new language and other cognitive skills. These may result from organic or psychological conditions. Relatively common subtypes include DYSLEXIA, DYSCALCULIA, and DYSGRAPHIA.	2.53	2	0
Cardiac Rupture, Traumatic [description not available]	2.13	1	0
Adverse Drug Event [description not available]	2.13	1	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.	2.13	1	0
Low Back Ache [description not available]	2.13	1	0
Low Back Pain Acute or chronic pain in the lumbar or sacral regions, which may be associated with musculo-ligamentous SPRAINS AND STRAINS; INTERVERTEBRAL DISK DISPLACEMENT; and other conditions.	7.13	1	0
Acquired-Immune Deficiency Syndrome Dementia Complex [description not available]	2.13	1	0
AIDS Dementia Complex A neurologic condition associated with the ACQUIRED IMMUNODEFICIENCY SYNDROME and characterized by impaired concentration and memory, slowness of hand movements, ATAXIA, incontinence, apathy, and gait difficulties associated with HIV-1 viral infection of the central nervous system. Pathologic examination of the brain reveals white matter rarefaction, perivascular infiltrates of lymphocytes, foamy macrophages, and multinucleated giant cells. (From Adams et al., Principles of Neurology, 6th ed, pp760-1; N Engl J Med, 1995 Apr 6;332(14):934-40)	2.13	1	0
Amentia [description not available]	2.13	1	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.	2.13	1	0
Leucocythaemia [description not available]	2.15	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)	2.15	1	0
Pericementitis [description not available]	2.15	1	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)	7.15	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.	2.43	2	0
Brain Swelling [description not available]	2.15	1	0
Hemorrhage, Subarachnoid [description not available]	2.15	1	0
Brain Edema Increased intracellular or extracellular fluid in brain tissue. Cytotoxic brain edema (swelling due to increased intracellular fluid) is indicative of a disturbance in cell metabolism, and is commonly associated with hypoxic or ischemic injuries (see HYPOXIA, BRAIN). An increase in extracellular fluid may be caused by increased brain capillary permeability (vasogenic edema), an osmotic gradient, local blockages in interstitial fluid pathways, or by obstruction of CSF flow (e.g., obstructive HYDROCEPHALUS). (From Childs Nerv Syst 1992 Sep; 8(6):301-6)	2.15	1	0
Subarachnoid Hemorrhage Bleeding into the intracranial or spinal SUBARACHNOID SPACE, most resulting from INTRACRANIAL ANEURYSM rupture. It can occur after traumatic injuries (SUBARACHNOID HEMORRHAGE, TRAUMATIC). Clinical features include HEADACHE; NAUSEA; VOMITING, nuchal rigidity, variable neurological deficits and reduced mental status.	7.15	1	0
Degenerative Diseases, Central Nervous System [description not available]	2.51	2	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.	2.51	2	0
Acute Edematous Pancreatitis [description not available]	2.15	1	0
Acute Disease Disease having a short and relatively severe course.	2.15	1	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.	2.15	1	0
Genome Instability [description not available]	2.44	2	0
Abnormalities, Autosome [description not available]	2.96	4	0
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	2.05	1	0
Chronic Fatigue and Immune Dysfunction Syndrome [description not available]	2.05	1	0
Fatigue Syndrome, Chronic A syndrome characterized by persistent or recurrent fatigue, diffuse musculoskeletal pain, sleep disturbances, and subjective cognitive impairment of 6 months duration or longer. Symptoms are not caused by ongoing exertion; are not relieved by rest; and result in a substantial reduction of previous levels of occupational, educational, social, or personal activities. Minor alterations of immune, neuroendocrine, and autonomic function may be associated with this syndrome. There is also considerable overlap between this condition and FIBROMYALGIA. (From Semin Neurol 1998;18(2):237-42; Ann Intern Med 1994 Dec 15;121(12): 953-9)	2.05	1	0
Contact Dermatitis [description not available]	2.05	1	0
Dermatitis, Contact A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	2.05	1	0
Akinetic-Rigid Variant of Huntington Disease [description not available]	2.05	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)	2.05	1	0
Apoplexy [description not available]	2.05	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)	7.05	1	0
Absence Status [description not available]	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)	7.06	1	0
Cystic Fibrosis of Pancreas [description not available]	2.06	1	0
Cystic Fibrosis An autosomal recessive genetic disease of the EXOCRINE GLANDS. It is caused by mutations in the gene encoding the CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR expressed in several organs including the LUNG, the PANCREAS, the BILIARY SYSTEM, and the SWEAT GLANDS. Cystic fibrosis is characterized by epithelial secretory dysfunction associated with ductal obstruction resulting in AIRWAY OBSTRUCTION; chronic RESPIRATORY INFECTIONS; PANCREATIC INSUFFICIENCY; maldigestion; salt depletion; and HEAT PROSTRATION.	7.06	1	0
Adjuvant Arthritis [description not available]	2.06	1	0
Marasmus [description not available]	2.06	1	0
Protein-Energy Malnutrition The lack of sufficient energy or protein to meet the body's metabolic demands, as a result of either an inadequate dietary intake of protein, intake of poor quality dietary protein, increased demands due to disease, or increased nutrient losses.	2.06	1	0
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.	2.67	3	0
Granulocytic Leukemia, Chronic [description not available]	2.06	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.	2.06	1	0
Alveolar Bone Atrophy [description not available]	2.06	1	0
Chromosomal Instability An increased tendency to acquire CHROMOSOME ABERRATIONS when various processes involved in chromosome replication, repair, or segregation are dysfunctional.	7.06	1	0
Cat Diseases Diseases of the domestic cat (Felis catus or F. domesticus). This term does not include diseases of the so-called big cats such as CHEETAHS; LIONS; tigers, cougars, panthers, leopards, and other Felidae for which the heading CARNIVORA is used.	3.45	1	1
Break-Bone Fever [description not available]	2.06	1	0
Dengue An acute febrile disease transmitted by the bite of AEDES mosquitoes infected with DENGUE VIRUS. It is self-limiting and characterized by fever, myalgia, headache, and rash. SEVERE DENGUE is a more virulent form of dengue.	2.06	1	0
Carcinoma 256, Walker A transplantable carcinoma of the rat that originally appeared spontaneously in the mammary gland of a pregnant albino rat, and which now resembles a carcinoma in young transplants and a sarcoma in older transplants. (Stedman, 25th ed)	2.07	1	0
Cachexia General ill health, malnutrition, and weight loss, usually associated with chronic disease.	2.07	1	0
Brain Thrombosis [description not available]	2.07	1	0
Asymmetric Diabetic Proximal Motor Neuropathy [description not available]	2.07	1	0
Nerve Pain [description not available]	2.07	1	0
Diabetic Neuropathies Peripheral, autonomic, and cranial nerve disorders that are associated with DIABETES MELLITUS. These conditions usually result from diabetic microvascular injury involving small blood vessels that supply nerves (VASA NERVORUM). Relatively common conditions which may be associated with diabetic neuropathy include third nerve palsy (see OCULOMOTOR NERVE DISEASES); MONONEUROPATHY; mononeuropathy multiplex; diabetic amyotrophy; a painful POLYNEUROPATHY; autonomic neuropathy; and thoracoabdominal neuropathy. (From Adams et al., Principles of Neurology, 6th ed, p1325)	2.07	1	0
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.07	1	0
Electrocardiogram QT Prolonged [description not available]	2.01	1	0
Torsade de Pointes [description not available]	2.01	1	0
Long QT Syndrome A condition that is characterized by episodes of fainting (SYNCOPE) and varying degree of ventricular arrhythmia as indicated by the prolonged QT interval. The inherited forms are caused by mutation of genes encoding cardiac ion channel proteins. The two major forms are ROMANO-WARD SYNDROME and JERVELL-LANGE NIELSEN SYNDROME.	2.01	1	0
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	2.42	2	0
Arteriosclerosis Thickening and loss of elasticity of the walls of ARTERIES of all sizes. There are many forms classified by the types of lesions and arteries involved, such as ATHEROSCLEROSIS with fatty lesions in the ARTERIAL INTIMA of medium and large muscular arteries.	2.7	3	0
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	6.93	1	0
Glycosuria The appearance of an abnormally large amount of GLUCOSE in the urine, such as more than 500 mg/day in adults. It can be due to HYPERGLYCEMIA or genetic defects in renal reabsorption (RENAL GLYCOSURIA).	1.93	1	0
Carcinoma, Epidermoid [description not available]	2.02	1	0
Cancer of Mouth [description not available]	2.44	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)	2.02	1	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	2.44	2	0
Eczema, Atopic [description not available]	2.02	1	0
Hay Fever [description not available]	2.02	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.	2.02	1	0
Rhinitis, Allergic, Seasonal Allergic rhinitis that occurs at the same time every year. It is characterized by acute CONJUNCTIVITIS with lacrimation and ITCHING, and regarded as an allergic condition triggered by specific ALLERGENS.	2.02	1	0
Uveitis, Anterior Inflammation of the anterior uvea comprising the iris, angle structures, and the ciliary body. Manifestations of this disorder include ciliary injection, exudation into the anterior chamber, iris changes, and adhesions between the iris and lens (posterior synechiae). Intraocular pressure may be increased or reduced.	2.02	1	0
Endotoxin Shock [description not available]	7.03	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.	2.03	1	0
Allergic Contact Dermatitis [description not available]	2.03	1	0
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	2.03	1	0
Cardiac Diseases [description not available]	2.03	1	0
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	2.03	1	0
Caries, Dental [description not available]	2.03	1	0
Dental Plaque A film that attaches to teeth, often causing DENTAL CARIES and GINGIVITIS. It is composed of MUCINS, secreted from salivary glands, and microorganisms.	2.03	1	0
Dental Caries Localized destruction of the tooth surface initiated by decalcification of the enamel followed by enzymatic lysis of organic structures and leading to cavity formation. If left unchecked, the cavity may penetrate the enamel and dentin and reach the pulp.	2.03	1	0
Parodontosis [description not available]	2.04	1	0
Periodontal Diseases Pathological processes involving the PERIODONTIUM including the gum (GINGIVA), the alveolar bone (ALVEOLAR PROCESS), the DENTAL CEMENTUM, and the PERIODONTAL LIGAMENT.	2.04	1	0
Bladder Cancer [description not available]	2.04	1	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.04	1	0
Esophagitis, Reflux [description not available]	2.03	1	0
Esophagitis, Peptic INFLAMMATION of the ESOPHAGUS that is caused by the reflux of GASTRIC JUICE with contents of the STOMACH and DUODENUM.	2.03	1	0
Primary Peritonitis [description not available]	1.95	1	0
Edema, Pulmonary [description not available]	1.95	1	0
Peritonitis INFLAMMATION of the PERITONEUM lining the ABDOMINAL CAVITY as the result of infectious, autoimmune, or chemical processes. Primary peritonitis is due to infection of the PERITONEAL CAVITY via hematogenous or lymphatic spread and without intra-abdominal source. Secondary peritonitis arises from the ABDOMINAL CAVITY itself through RUPTURE or ABSCESS of intra-abdominal organs.	6.95	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.	6.95	1	0
Gastric Ulcer [description not available]	1.98	1	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).	1.98	1	0
Adenocarcinoma, Basal Cell [description not available]	1.98	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	1.98	1	0
Infectious Endophthalmitis Infectious condition of the internal eye.	1.98	1	0
Endophthalmitis Suppurative inflammation of the tissues of the internal structures of the eye frequently associated with an infection.	1.98	1	0
Uveitis, Posterior Inflammation of the choroid as well as the retina and vitreous body. Some form of visual disturbance is usually present. The most important characteristics of posterior uveitis are vitreous opacities, choroiditis, and chorioretinitis.	1.98	1	0
Gastroduodenal Ulcer [description not available]	2.92	1	0
Peptic Ulcer Ulcer that occurs in the regions of the GASTROINTESTINAL TRACT which come into contact with GASTRIC JUICE containing PEPSIN and GASTRIC ACID. It occurs when there are defects in the MUCOSA barrier. The common forms of peptic ulcers are associated with HELICOBACTER PYLORI and the consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	2.92	1	0

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naringin

Cross-References

Synonyms (98)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Occurs in Manufacturing (3 Product(s))

Product Categories

Products

Roles (3)

Drug Classes (5)

Pathways (1)

Protein Targets (13)

Potency Measurements

Inhibition Measurements

Activation Measurements

Biological Processes (85)

Molecular Functions (35)

Ceullar Components (38)

Bioassays (89)

Research

Studies (899)

Market Indicators

Research Demand Index: 42.36

Study Types

Related Drugs (1,369)

Related Conditions (386)