bisdemethoxycurcumin profile

curcumin III: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

bisdemethoxycurcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups. [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]

Products

ID Source	ID
PubMed CID	5315472
CHEMBL ID	105350
CHEBI ID	71045
SCHEMBL ID	428638
SCHEMBL ID	13521971
MeSH ID	M0106979

Synonym
nsc-687839
c19h16o4
bisdemethoxycurcumin
bis(4-hydroxycinnamoyl)methane
1,6-heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-
24939-16-0
bis-demethoxycurcumin
(1e,6e)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
1,6-heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-, (1e,6e)-
nsc687839
curcumin iii
curcuminoid a
33171-05-0
didemethoxycurcumin
B3347
1,7-bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione
BRD-K37445107-001-01-9
bisdemethoxy curcumin
CHEMBL105350 ,
chebi:71045 ,
curcumin lll
cid_5324473
bdbm50059989
1,7-bis(4-hydroxyphenyl)-3-hydroxy-1,3,6-heptatrien-5-one
(1e,4z,6e)-5-hydroxy-1,7-bis-(4-hydroxy-phenyl)-hepta-1,4,6-trien-3-one
(1e,6e)-1,7-bis-(4-hydroxy-phenyl)-hepta-1,6-diene-3,5-dione
5-hydroxy-1,7-bis-(4-hydroxy-phenyl)-hepta-1,4,6-trien-3-one
1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
bisdesmethoxycurcumin
bis(p-hydroxycinnamoyl)methane
1,6-heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-, (e,e)-
2efo1bp34r ,
unii-2efo1bp34r
bhcmt
AKOS015902102
bisdesmethoxycurcumin [usp-rs]
ins no.100(iii)
e-100(iii)
bis-demethoxycurcumin [inci]
1,7-bis-(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dione
ins-100(iii)
CCG-207959
CCG-208635
SCHEMBL428638
SCHEMBL13521971
mfcd03419284
bisdemethoxycucurmin
Q-100322
AC-24239
(e,e)-bisdemethoxycurcumin
bisdemethoxycurcumin, analytical standard
bisdemethoxycurcumin, >=98% (hplc), solid
DTXSID00872663
1,7-bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione(e,e)
AS-68737
(1e,6e)-1,7-bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione
Q4917168
di-p-coumaroylmethane
dide methoxycurcu min
(1e,6e)-1,7-bis(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dione
A14544
p,p'-dihydroxydicinnamoylmethane
curcumin iii;didemethoxycurcumin
22608-12-4
adamantan-1-yl-aceticacidhydrazide
AS-57295
S3938
ZAA93916
AC-34720
A875406
HY-N0007A
CS-0018287
bdmc;(e,e)-curcumin iii

Excerpt	Reference	Relevance
"Bisdemethoxycurcumin (BDMC) is an affordable and safe curcuminoid with medicinal properties."	( Bisdemethoxycurcumin-mediated Attenuation of Apoptosis Prevents Gentamicin-induced Ototoxicity in Mouse Cochlear UB/OC-2 Cells. Hsu, CJ; Kang, TY; Lin, HY; Lin, JN; Tseng, GF; Wang, JS; Wen, YH; Wu, CC; Wu, HP; Wu, RS; Yu, SH, )	2.3
"Bisdemethoxycurcumin (BDMC) is a natural demethoxy curcumin derivative."	( Bisdemethoxycurcumin Inhibits VEGF-Induced HUVECs Proliferation, Migration and Invasion through AMPK/mTOR Pathway-Dependent Autophagy Activation and Cell Cycle Arrest. Qu, T; Sun, C; Wang, M; Wang, X, 2022)	2.89
"Bisdemethoxycurcumin (BDMC), which is a classical derivative of curcumin, was found to have neuroprotective effects against a cell model of Alzheimer's disease (AD) in our previous studies."	( Bisdemethoxycurcumin inhibits oxidative stress and antagonizes Alzheimer's disease by up-regulating SIRT1. Chang, Y; He, B; He, D; Hu, R; Ma, R; Wang, Y; Wu, H; Wu, L; Xiao, Z; Xie, M; Xu, C; Xu, Y; Zhou, G, 2020)	2.72
"Bisdemethoxycurcumin (BDMC) is a natural derivative of curcumin present in the phenolic components extracted from the dried rhizome of Curcuma longa L. "	( Bisdemethoxycurcumin suppresses MCF-7 cells proliferation by inducing ROS accumulation and modulating senescence-related pathways. Gao, JL; Hoi, PM; Lee, SM; Li, YB; Wang, YT; Zhong, ZF, 2013)	3.28
"Bisdemethoxycurcumin (BDMC) is a natural derivative of curcumin with anti-inflammatory and anti-cancer activities."	( Bisdemethoxycurcumin Induces apoptosis in activated hepatic stellate cells via cannabinoid receptor 2. Jee, JG; Kim, HP; Lee, PJ; Sung, SH; Woo, SJ, 2015)	2.58
"Bisdemethoxycurcumin (BDMC) is an active component of curcumin and a chemotherapeutic agent, which has been suggested to inhibit tumor growth, invasion and metastasis in multiple cancers. "	( Role of Wnt Inhibitory Factor-1 in Inhibition of Bisdemethoxycurcumin Mediated Epithelial-to-Mesenchymal Transition in Highly Metastatic Lung Cancer 95D Cells. Gong, L; Tang, CL; Wang, HJ; Xu, JH; Yang, HP; Zhou, XD, 2015)	2.11
"Bisdemethoxycurcumin (BDMC) is a minor constituent (approximately 3%) of curcuminoids that has been shown to be more stable than the other two main curcuminoids, that is, curcumin and demthoxycurcumin."	( Promising anti-tumor properties of bisdemethoxycurcumin: A naturally occurring curcumin analogue. Hatamipour, M; Ramezani, M; Sahebkar, A, 2018)	1.48

Excerpt	Reference	Relevance
"Bisdemethoxycurcumin has good antioxidant and anti-inflammatory effects and has been widely used as food and feed supplements in the form of curcuminoids. "	( Bisdemethoxycurcumin attenuates lipopolysaccharide-induced intestinal damage through improving barrier integrity, suppressing inflammation, and modulating gut microbiota in broilers. Han, H; Wang, T; Yang, Y; Zhang, J; Zhang, L, 2021)	3.51
"Bisdemethoxycurcumin has shown positive effects on inflammatory diseases."	( Investigating the Mechanisms of Bisdemethoxycurcumin in Ulcerative Colitis: Network Pharmacology and Experimental Verification. Chen, H; Jiang, R; Lian, Q; Sha, W; Tu, S; Wu, H; Yang, Q; Zeng, R; Zhuo, Z, 2022)	1.73
"Bisdemethoxycurcumin (BDCur) has been found widely in foods such as cheese, butter, etc., and in curry (powder) as a spice. "	( Natural borneol enhances bisdemethoxycurcumin-induced cell cycle arrest in the G2/M phase through up-regulation of intracellular ROS in HepG2 cells. Chen, J; Chen, T; Li, L; Su, J, 2015)	2.16

Excerpt	Reference	Relevance
"Bisdemethoxycurcumin appears to enhance immune function in mononuclear cells of AD patients and may provide a novel approach to AD immunotherapy."	( Immune defects in Alzheimer's disease: new medications development. Abel, KJ; Cashman, JR; Fiala, M; Ghirmai, S, 2008)	1.07

Excerpt	Reference	Relevance
" Our investigation clearly revealed that NBDMCA is hemocompatible in vitro and also safe to vital organs in vivo."	( Future of nano bisdemethoxy curcumin analog: guaranteeing safer intravenous delivery. Devasena, T; Francis, AP; Ganapathy, S; Murthy, PB; Palla, VR, 2015)	0.42
"Studies have shown that lead (Pb) is one of hazardous heavy metals with various adverse effects on human health including mental health; Pb can induce psychiatric disorders like anxiety."	( Lead (Pb) exposure induces physiological alterations in the serotoninergic and vasopressin systems causing anxiogenic-like behavior in Meriones shawi: Assessment of BDMC as a neuroprotective compound for Pb-neurotoxicity and kidney damages. Abbaoui, A; Bouyatas, MM; El Khiat, A; Gamrani, H; Tamegart, L, 2021)	0.62
" Bisdemethoxycurcumin (BDMC) is an affordable and safe curcuminoid with medicinal properties."	( Bisdemethoxycurcumin-mediated Attenuation of Apoptosis Prevents Gentamicin-induced Ototoxicity in Mouse Cochlear UB/OC-2 Cells. Hsu, CJ; Kang, TY; Lin, HY; Lin, JN; Tseng, GF; Wang, JS; Wen, YH; Wu, CC; Wu, HP; Wu, RS; Yu, SH, )	2.48

Excerpt	Reference	Relevance
" Antimalarial activity of curcuminoids-loaded liposomes alone and in combination with α/β arteether when administered intravenously, was evaluated in Plasmodium berghei infected mice."	( Curcuminoids-loaded liposomes in combination with arteether protects against Plasmodium berghei infection in mice. Aditya, NP; Banerjee, R; Chimote, G; Gunalan, K; Madhusudhan, B; Patankar, S, 2012)	0.38

Excerpt	Reference	Relevance
" It appeared that co-existing curcuminoids improved the bioavailability of curcumin."	( Metabolic and pharmacokinetic studies of curcumin, demethoxycurcumin and bisdemethoxycurcumin in mice tumor after intragastric administration of nanoparticle formulations by liquid chromatography coupled with tandem mass spectrometry. Guo, D; He, R; Li, Q; Li, R; Lin, X; Qiao, X; Xiang, C; Ye, M, 2011)	0.6
"Curcuminoid, a dietary polyphenolic compound, has poor water solubility and low bioavailability following oral administration."	( Preparation and oral bioavailability study of curcuminoid-loaded microemulsion. Chen, X; Meng, F; Ping, Q; Xiao, Y; Yang, L; Zhu, X; Zou, L, 2013)	0.39
" Poor oral bioavailability and the low plasma concentration of curcuminoids limited their clinical use, and one of the major reasons is their rapid metabolism in vivo."	( Curcuminoid metabolism and its contribution to the pharmacological effects. Qiu, F; Wang, K, 2013)	0.39
" However its bioavailability is low due to its limited intestinal uptake and rapid metabolism."	( The oral bioavailability of curcumin from micronized powder and liquid micelles is significantly increased in healthy humans and differs between sexes. Behnam, D; Frank, J; Jandasek, J; Kocher, A; Schiborr, C; Toelstede, S, 2014)	0.4
"Both, the micronized powder and in particular the liquid micellar formulation of curcumin significantly improved its oral bioavailability without altering safety parameters and may thus be ideally suited to deliver curcumin in human intervention trials."	( The oral bioavailability of curcumin from micronized powder and liquid micelles is significantly increased in healthy humans and differs between sexes. Behnam, D; Frank, J; Jandasek, J; Kocher, A; Schiborr, C; Toelstede, S, 2014)	0.4
") administration which showed enhanced bioavailability of curcuminoids in brain as compared to intravenous administration."	( PNIPAM nanoparticles for targeted and enhanced nose-to-brain delivery of curcuminoids: UPLC/ESI-Q-ToF-MS/MS-based pharmacokinetics and pharmacodynamic evaluation in cerebral ischemia model. Ahmad, FJ; Ahmad, I; Ahmad, N; Iqbal, Z; Samim, M; Umar, S, 2016)	0.43
"Poor oral bioavailability of curcuminoids limited their various applications, and one of the main reasons is their rapid metabolism in vivo."	( Sulfonation of curcuminoids: characterization and contribution of individual SULT enzymes. Han, L; Jiang, K; Lu, X; Ma, Y; Meng, S; Zhang, M; Zhou, Y, 2015)	0.42
" As there is no BDMCA sensor available so far, this type of detection is very essential to monitor the pharmacokinetic behavior, the therapeutic dosage, bioavailability and related toxicity of BDMCA in different formulations and samples."	( State of the Art Detection System for Curcumin Analog. Devasena, T; Francis, AP; Jebarani, AH, 2015)	0.42
" While the rich bioavailability research of curcumin, BDMC is the poor studies."	( Hepatoprotective Effect and Synergism of Bisdemethoycurcumin against MCD Diet-Induced Nonalcoholic Fatty Liver Disease in Mice. Ahn, YS; Cha, SW; Han, SH; Kang, OH; Kim, SB; Kong, R; Kwon, DY; Lee, YS; Seo, YS, 2016)	0.43
"The oral bioavailability of curcuminoids is low, but can be enhanced by incorporation into micelles."	( Intratumoral Concentrations and Effects of Orally Administered Micellar Curcuminoids in Glioblastoma Patients. Dützmann, S; Frank, J; Franz, K; Geßler, F; Hattingen, E; Kocher, A; Pilatus, U; Quick-Weller, J; Schiborr, C; Seifert, V; Senft, C; Weissenberger, J, )	0.13
" Unfortunately, most curcuminoids poorly reach their site of action because of low bioavailability issues, (partly) associated with the labile β-diketo structure."	( Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress. D'hooghe, M; D'hoore, S; De Vreese, R; Grootaert, C; Theppawong, A; Van Bogaert, M; Van Camp, J; Van Damme, S, 2016)	0.43
" In that respect, augmenting the water solubility by structural modification of the curcumin scaffold may result in improved bioavailability and pharmacokinetics."	( Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids. D'hooghe, M; De Vreese, R; Grootaert, C; Theppawong, A; Van Camp, J; Vannecke, L, 2016)	0.43
" In this study, we investigated the bioavailability of a new γ-cyclodextrin curcumin formulation (CW8)."	( Analysis of different innovative formulations of curcumin for improved relative oral bioavailability in human subjects. Lowery, RP; Mannan, H; Münch, G; Purpura, M; Razmovski-Naumovski, V; Wilson, JM, 2018)	0.48
" Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism."	( Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin. Deck, LM; Hunsaker, LA; Royer, RE; Vander Jagt, DL; Vander Jagt, TA; Whalen, LJ, 2018)	0.48
" However, the poor stability, solubility, in vivo bioavailability and weak activity of CU greatly limit its clinical application."	( Recent advances of analogues of curcumin for treatment of cancer. Pi, C; Wei, Y; Ye, Y; Zhao, L; Zhao, S, 2019)	0.51
"In spite of their extensive medicinal properties, cur and curcuminoids have poor solubility and bioavailability due to their hydrophobicity."	( Curcumin-C3 Complexed with α-, β-cyclodextrin Exhibits Antibacterial and Antioxidant Properties Suitable for Cancer Treatments. Huang, FY; Kumar, R; Reddy, DNK; Wang, SP, 2019)	0.51
"In this study, we sought to overcome the poor solubility and bioavailability of bismethoxycurcumin (BDMC) by fabricating a BDMC-loaded self micro-emulsifying system (BDMC-SMEDDS)."	( Enhanced oral bioavailability of Bisdemethoxycurcumin-loaded self-microemulsifying drug delivery system: Formulation design, in vitro and in vivo evaluation. Adu-Frimpong, M; Liu, J; Omari-Siaw, E; Wang, Q; Xu, X; Yu, J, 2020)	0.84
" However, BDC is almost insoluble in water, poorly absorbed by the organism, and degrades rapidly."	( Bisdemethoxycurcumin (BDC)-Loaded H-Ferritin-Nanocages Mediate the Regulation of Inflammation in Alzheimer's Disease Patients. Bonizzi, A; Busacca, M; Cereda, C; Corsi, F; Costa, A; Cotta Ramusino, M; Gagliardi, S; Garofalo, M; Mazzucchelli, S; Mocchi, M; Morasso, C; Negri, S; Pandini, C; Perini, G; Prosperi, D; Ricciardi, A; Sevieri, M; Sitia, L; Tinelli, V; Truffi, M, 2022)	2.16

Excerpt	Relevance	Reference
" Colon cancer was induced by sub-cutaneous injection of DMH at a dosage of 20mg/kg body weight (15 doses, at 1-week intervals)."	( Bis-1,7-(2-hydroxyphenyl)-hepta-1,6-diene-3,5-dione (a curcumin analog) ameliorates DMH-induced hepatic oxidative stress during colon carcinogenesis. Devasena, T; Menon, VP; Rajasekaran, KN, 2002)	0.31
" For curcumin-SLNs group, the dosing of 250 mg/kg of curcumin resulted in AUC((0-48 h)) of 2285 ngh/mL and C(max) of 209 ng/mL."	( Metabolic and pharmacokinetic studies of curcumin, demethoxycurcumin and bisdemethoxycurcumin in mice tumor after intragastric administration of nanoparticle formulations by liquid chromatography coupled with tandem mass spectrometry. Guo, D; He, R; Li, Q; Li, R; Lin, X; Qiao, X; Xiang, C; Ye, M, 2011)	0.6
" Both effects were observed to increase in proportion to the cellular uptake of curcuminoids; cellular uptake increased following an increase in the dosage of curcuminoids."	( The cellular uptake and cytotoxic effect of curcuminoids on breast cancer cells. Chang, CC; Chen, TY; Fu, CF; Hsu, YC; Yang, WT, 2012)	0.38
" It was found that the three curcumins could inhibit the proliferation of HUVEC cells induced by OX-LDL within the dosage range 4, 8, 16 mg x L(-1), with a dose-dependence."	( [Study on anti-angiogenesis effect of three curcumin pigments and expression of their relevant factors]. Ding, ZS; Huang, YF; Lv, GY; Zhu, XX, 2015)	0.42

Product Category	Products
Professional Supplements	1

Product	Brand	Category	Compounds Matched from Ingredients	Date Retrieved
Designs for Sport Curcumin Complex - NSF Certified for Sport -- 60 Softgels	Designs for Sport	Professional Supplements	bisdemethoxycurcumin, demethoxycurcumin	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.
EC 3.2.1.1 (alpha-amylase) inhibitor	An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-amylase (EC 3.2.1.1).
[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
beta-diketone	A diketone in which the two keto groups are separated by a single carbon atom.
polyphenol	Members of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group.
enone	An alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position.
diarylheptanoid	A family of plant metabolites with a common 1,7-diphenylheptane structural skeleton, carrying various substituents. They are mainly distributed in the roots, rhizomes and bark of Alpinia, Zingiber, Curcuma and Alnus species.
[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]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Acetylcholinesterase	Electrophorus electricus (electric eel)	IC50 (µMol)	18.2700	0.0000	0.9453	9.9400	AID747035
Aldo-keto reductase family 1 member B10	Homo sapiens (human)	IC50 (µMol)	0.0600	0.0010	1.9445	9.6000	AID1465693
Aldo-keto reductase family 1 member B1	Homo sapiens (human)	IC50 (µMol)	5.1000	0.0010	1.1913	10.0000	AID1465694
CPG DNA methylase	Spiroplasma monobiae	IC50 (µMol)	0.0300	0.0028	0.5582	1.6000	AID367266
Sodium-dependent dopamine transporter	Rattus norvegicus (Norway rat)	IC50 (µMol)	36.3700	0.0007	0.9774	9.7000	AID247571
Prostaglandin G/H synthase 2	Homo sapiens (human)	IC50 (µMol)	36.3700	0.0001	0.9950	10.0000	AID247571
Lactoylglutathione lyase	Homo sapiens (human)	Ki	18.1000	0.0012	2.5947	9.1400	AID568008; AID604299
Integrase	Human immunodeficiency virus 1	IC50 (µMol)	100.0000	0.0005	1.5443	10.0000	AID91579; AID93381; AID93515; AID93530
Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)	IC50 (µMol)	37.0000	0.0000	1.6395	10.0000	AID687453
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
retinoid metabolic process	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
farnesol catabolic process	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
retinol metabolic process	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
daunorubicin metabolic process	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
doxorubicin metabolic process	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
cellular detoxification of aldehyde	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
retinoid metabolic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
epithelial cell maturation	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
renal water homeostasis	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
carbohydrate metabolic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
prostaglandin metabolic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
C21-steroid hormone biosynthetic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
L-ascorbic acid biosynthetic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
regulation of urine volume	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
retinol metabolic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
negative regulation of apoptotic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
daunorubicin metabolic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
doxorubicin metabolic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
fructose biosynthetic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
cellular hyperosmotic salinity response	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
metanephric collecting duct development	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
prostaglandin biosynthetic process	Prostaglandin G/H synthase 2	Homo sapiens (human)
angiogenesis	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to oxidative stress	Prostaglandin G/H synthase 2	Homo sapiens (human)
embryo implantation	Prostaglandin G/H synthase 2	Homo sapiens (human)
learning	Prostaglandin G/H synthase 2	Homo sapiens (human)
memory	Prostaglandin G/H synthase 2	Homo sapiens (human)
regulation of blood pressure	Prostaglandin G/H synthase 2	Homo sapiens (human)
negative regulation of cell population proliferation	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to xenobiotic stimulus	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to nematode	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to fructose	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to manganese ion	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of vascular endothelial growth factor production	Prostaglandin G/H synthase 2	Homo sapiens (human)
cyclooxygenase pathway	Prostaglandin G/H synthase 2	Homo sapiens (human)
bone mineralization	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of prostaglandin biosynthetic process	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of fever generation	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of synaptic plasticity	Prostaglandin G/H synthase 2	Homo sapiens (human)
negative regulation of synaptic transmission, dopaminergic	Prostaglandin G/H synthase 2	Homo sapiens (human)
prostaglandin secretion	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to estradiol	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to lipopolysaccharide	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of peptidyl-serine phosphorylation	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to vitamin D	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to heat	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to tumor necrosis factor	Prostaglandin G/H synthase 2	Homo sapiens (human)
maintenance of blood-brain barrier	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of protein import into nucleus	Prostaglandin G/H synthase 2	Homo sapiens (human)
hair cycle	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of apoptotic process	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of nitric oxide biosynthetic process	Prostaglandin G/H synthase 2	Homo sapiens (human)
negative regulation of cell cycle	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of vasoconstriction	Prostaglandin G/H synthase 2	Homo sapiens (human)
negative regulation of smooth muscle contraction	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of smooth muscle contraction	Prostaglandin G/H synthase 2	Homo sapiens (human)
decidualization	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of smooth muscle cell proliferation	Prostaglandin G/H synthase 2	Homo sapiens (human)
regulation of inflammatory response	Prostaglandin G/H synthase 2	Homo sapiens (human)
brown fat cell differentiation	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to glucocorticoid	Prostaglandin G/H synthase 2	Homo sapiens (human)
negative regulation of calcium ion transport	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of synaptic transmission, glutamatergic	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to fatty acid	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to mechanical stimulus	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to lead ion	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to ATP	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to hypoxia	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to non-ionic osmotic stress	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to fluid shear stress	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of transforming growth factor beta production	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of cell migration involved in sprouting angiogenesis	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of fibroblast growth factor production	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of brown fat cell differentiation	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of platelet-derived growth factor production	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular oxidant detoxification	Prostaglandin G/H synthase 2	Homo sapiens (human)
regulation of neuroinflammatory response	Prostaglandin G/H synthase 2	Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to osmotic stress	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to homocysteine	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to angiotensin	Prostaglandin G/H synthase 2	Homo sapiens (human)
carbohydrate metabolic process	Lactoylglutathione lyase	Homo sapiens (human)
regulation of transcription by RNA polymerase II	Lactoylglutathione lyase	Homo sapiens (human)
glutathione metabolic process	Lactoylglutathione lyase	Homo sapiens (human)
methylglyoxal metabolic process	Lactoylglutathione lyase	Homo sapiens (human)
osteoclast differentiation	Lactoylglutathione lyase	Homo sapiens (human)
negative regulation of apoptotic process	Lactoylglutathione lyase	Homo sapiens (human)
G1/S transition of mitotic cell cycle	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
response to ischemia	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
protein phosphorylation	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
calcium ion transport	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
positive regulation of cardiac muscle cell apoptotic process	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
peptidyl-serine phosphorylation	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
cellular response to interferon-beta	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
angiotensin-activated signaling pathway	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
positive regulation of receptor signaling pathway via JAK-STAT	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
protein autophosphorylation	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
regulation of neurotransmitter secretion	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
regulation of neuronal synaptic plasticity	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
positive regulation of NF-kappaB transcription factor activity	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
negative regulation of hydrolase activity	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
positive regulation of calcium ion transport	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
dendritic spine development	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
cellular response to type II interferon	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
regulation of mitochondrial membrane permeability involved in apoptotic process	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
peptidyl-threonine autophosphorylation	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
regulation of endocannabinoid signaling pathway	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
regulation of neuron migration	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
retinal dehydrogenase activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
aldo-keto reductase (NADPH) activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
protein binding	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
alcohol dehydrogenase (NADP+) activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
geranylgeranyl reductase activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
allyl-alcohol dehydrogenase activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
indanol dehydrogenase activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
aldose reductase (NADPH) activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
retinal dehydrogenase activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
aldose reductase (NADPH) activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
protein binding	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
electron transfer activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
prostaglandin H2 endoperoxidase reductase activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
glyceraldehyde oxidoreductase activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
allyl-alcohol dehydrogenase activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
L-glucuronate reductase activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
glycerol dehydrogenase [NADP+] activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
peroxidase activity	Prostaglandin G/H synthase 2	Homo sapiens (human)
prostaglandin-endoperoxide synthase activity	Prostaglandin G/H synthase 2	Homo sapiens (human)
protein binding	Prostaglandin G/H synthase 2	Homo sapiens (human)
enzyme binding	Prostaglandin G/H synthase 2	Homo sapiens (human)
heme binding	Prostaglandin G/H synthase 2	Homo sapiens (human)
protein homodimerization activity	Prostaglandin G/H synthase 2	Homo sapiens (human)
metal ion binding	Prostaglandin G/H synthase 2	Homo sapiens (human)
oxidoreductase activity, acting on single donors with incorporation of molecular oxygen, incorporation of two atoms of oxygen	Prostaglandin G/H synthase 2	Homo sapiens (human)
lactoylglutathione lyase activity	Lactoylglutathione lyase	Homo sapiens (human)
protein binding	Lactoylglutathione lyase	Homo sapiens (human)
zinc ion binding	Lactoylglutathione lyase	Homo sapiens (human)
protein serine/threonine kinase activity	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
calmodulin-dependent protein kinase activity	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
protein binding	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
calmodulin binding	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
ATP binding	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
kinase activity	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
glutamate receptor binding	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
identical protein binding	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
protein homodimerization activity	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
metal ion binding	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
protein serine kinase activity	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
extracellular region	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
lysosome	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
cytosol	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
cytosol	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
mitochondrion	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
extracellular space	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
nucleoplasm	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
cytosol	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
extracellular exosome	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
cytosol	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
nuclear inner membrane	Prostaglandin G/H synthase 2	Homo sapiens (human)
nuclear outer membrane	Prostaglandin G/H synthase 2	Homo sapiens (human)
cytoplasm	Prostaglandin G/H synthase 2	Homo sapiens (human)
endoplasmic reticulum	Prostaglandin G/H synthase 2	Homo sapiens (human)
endoplasmic reticulum lumen	Prostaglandin G/H synthase 2	Homo sapiens (human)
endoplasmic reticulum membrane	Prostaglandin G/H synthase 2	Homo sapiens (human)
caveola	Prostaglandin G/H synthase 2	Homo sapiens (human)
neuron projection	Prostaglandin G/H synthase 2	Homo sapiens (human)
protein-containing complex	Prostaglandin G/H synthase 2	Homo sapiens (human)
neuron projection	Prostaglandin G/H synthase 2	Homo sapiens (human)
cytoplasm	Prostaglandin G/H synthase 2	Homo sapiens (human)
nucleoplasm	Lactoylglutathione lyase	Homo sapiens (human)
cytoplasm	Lactoylglutathione lyase	Homo sapiens (human)
cytosol	Lactoylglutathione lyase	Homo sapiens (human)
plasma membrane	Lactoylglutathione lyase	Homo sapiens (human)
extracellular exosome	Lactoylglutathione lyase	Homo sapiens (human)
nucleus	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
nucleoplasm	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
mitochondrion	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
cytosol	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
postsynaptic density	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
endocytic vesicle membrane	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
dendritic spine	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
calcium- and calmodulin-dependent protein kinase complex	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
neuron projection	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
cytoplasm	Calcium/calmodulin-dependent protein kinase type II subunit alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (171)

Assay ID	Title	Year	Journal	Article
AID515080	Antimycobacterial activity against Mycobacterium tuberculosis H37Ra after 24 hrs by microtiter alamar blue assay	2010	European journal of medicinal chemistry, Oct, Volume: 45, Issue:10	Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity.
AID1511037	Cell cycle arrest in human SKOV3 cells assessed as accumulation at G1 phase at 15 umol/L after 24 hrs by propidium iodide staining-based assay (Rvb = 58.1%)	2019	European journal of medicinal chemistry, Oct-15, Volume: 180	Recent advances of analogues of curcumin for treatment of cancer.
AID754240	Toxicity in human MDA-MB-231 cells xenografted athymic nude mouse left cardiac ventricle assessed as effect on white blood cells at 50 mg/kg, ip administered every other day for 3 weeks (Rvb = 35.84 +/- 1.3 K/uL)	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID754255	Inhibition of osteolytic bone metastases in human MDA-MB-231 cells xenografted in athymic nude mouse left cardiac ventricle assessed as reduction in lytic bone lesion area at 25 to 50 mg/kg, ip administered every other day for 3 weeks measured on day 16 r	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID1330229	Induction of ROS generation in human Caco2 cells at 10 uM using DCFH-DA by fluorescence assay relative to control	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID466921	Antileishmanial activity against Leishmania mexicana MNYC/BZ/62/M379 amastigotes after 48 hrs by alamar blue assay	2010	European journal of medicinal chemistry, Mar, Volume: 45, Issue:3	Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID754262	Inhibition of TGF-beta-induced PTHrP secretion in human MDA-MB-231 cells treated 4 hrs before TGF-beta challenge measured after 24 hrs by radioimmunoassay	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID754260	Cytotoxicity against human MDA-MB-231 cells assessed as cell viability by MTT assay	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID1330214	Aqueous solubility of the compound in sodium phosphate buffer at pH 6.8 after 24 hrs by shake flask method	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID1169233	Cytotoxicity against mouse HT22 cells assessed as cell viability at 1 to 25 uM after 24 hrs by MTT assay relative to control	2014	Journal of natural products, Oct-24, Volume: 77, Issue:10	Synthesis of natural and non-natural curcuminoids and their neuroprotective activity against glutamate-induced oxidative stress in HT-22 cells.
AID1333303	Growth inhibition of undifferentiated human Caco2 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID403532	Cytotoxicity against human OVCAR-3 after 48 hrs	1998	Journal of natural products, Dec, Volume: 61, Issue:12	Cytotoxicity of curcuminoids and some novel compounds from Curcuma zedoaria.
AID1330237	Induction of ROS generation in human EAhy926 cells at 10 uM using DCFH-DA by fluorescence assay relative to control	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID1333301	Growth inhibition of CHOK1 cells measured after 72 hrs by SRB assay	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID1333304	Growth inhibition of undifferentiated human Caco2 cells measured after 72 hrs by SRB assay	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID1062644	Inhibition of Wnt3A/beta-catenin signaling in HEK293 cells at 5 uM after 24 hrs by firefly/renilla dual luciferase reporter gene assay relative to vehicle-treated control	2014	European journal of medicinal chemistry, Jan, Volume: 71	Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway.
AID402713	Cytotoxicity against human NCI-H460	2005	Journal of natural products, Jul, Volume: 68, Issue:7	A labdane diterpene glucoside from the rhizomes of Curcuma mangga.
AID376768	Inhibition of topoisomerase 2 in Saccharomyces cerevisiae JN394t2-5 assessed as inhibition of growth at 50 ug/mL after 72 hrs	1998	Journal of natural products, Apr, Volume: 61, Issue:4	Novel bioactivities of Curcuma longa constituents.
AID1198247	Antiinvasive activity against human MCF7/6 cells precultured with 9 day old chick embryo heart tissue fragment at 0.01 micromol/l by chick heart invasion assay	2015	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 25, Issue:5	Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids.
AID1395721	Cytotoxicity against human WRL68 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay	2018	European journal of medicinal chemistry, May-10, Volume: 151	Antiproliferative efficacy of curcumin mimics through microtubule destabilization.
AID243850	Percent inhibition against Prostaglandin G/H synthase 1 from ram seminal vesicles at 100 uM	2005	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 15, Issue:7	Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammatory agents.
AID754251	Inhibition of osteolytic bone metastases in human MDA-MB-231 cells xenografted in athymic nude mouse left cardiac ventricle assessed as effect on tumor burden at 25 to 50 mg/kg, ip administered every other day for 3 weeks by histological analysis	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID376497	Inhibition of topoisomerase 2 in Saccharomyces cerevisiae JN394 assessed as inhibition of growth at 25 ug/mL after 72 hrs	1998	Journal of natural products, Apr, Volume: 61, Issue:4	Novel bioactivities of Curcuma longa constituents.
AID717731	Cytotoxicity against human HepG2 cells after 72 hrs by crystal violet staining based microplate reader analysis	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Terpecurcumins A-I from the rhizomes of Curcuma longa: absolute configuration and cytotoxic activity.
AID376766	Inhibition of topoisomerase 2 in Saccharomyces cerevisiae JN394 assessed as inhibition of growth at 50 ug/mL after 72 hrs	1998	Journal of natural products, Apr, Volume: 61, Issue:4	Novel bioactivities of Curcuma longa constituents.
AID1330235	Induction of ROS generation in CHOK1 cells at 10 uM using DCFH-DA by fluorescence assay relative to control	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID1395720	Cytotoxicity against human A431 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay	2018	European journal of medicinal chemistry, May-10, Volume: 151	Antiproliferative efficacy of curcumin mimics through microtubule destabilization.
AID1198244	Antiinvasive activity against human MCF7/6 cells precultured with 9 day old chick embryo heart tissue fragment at 10 micromol/l by chick heart invasion assay	2015	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 25, Issue:5	Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids.
AID1287161	Cytotoxicity against human HepG2 cells assessed as reduction in cell viability after 48 hrs by MTT assay	2016	European journal of medicinal chemistry, Apr-13, Volume: 112	3,3'-OH curcumin causes apoptosis in HepG2 cells through ROS-mediated pathway.
AID1330234	Induction of ROS generation in CHOK1 cells at 1 uM using DCFH-DA by fluorescence assay relative to control	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID402708	Antioxidant activity assessed as inhibition of copper-induced lipid peroxidation by Fe3(CN)6 method at 300 uM	2005	Journal of natural products, Jul, Volume: 68, Issue:7	A labdane diterpene glucoside from the rhizomes of Curcuma mangga.
AID376494	Inhibition of topoisomerase 1 in Saccharomyces cerevisiae JN394 assessed as inhibition of growth at 25 ug/mL after 72 hrs	1998	Journal of natural products, Apr, Volume: 61, Issue:4	Novel bioactivities of Curcuma longa constituents.
AID754244	Toxicity in human MDA-MB-231 cells xenografted athymic nude mouse left cardiac ventricle assessed as effect on spleen weight at 50 mg/kg, ip administered every other day for 3 weeks (Rvb = 0.134 +/- 0.02 gram)	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID95500	Compound concentration required to reduce the exponential growth of KB cells by 50%	1998	Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21	Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: synthesis, biological evaluation, and molecular modeling.
AID1333298	Antioxidant activity assessed as inhibition of DPPH radical activity at 1 uM measured after 30 mins under dark conditions by spectrophotometric analysis relative to control	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID328873	Increase in TLR2 protein expression in PBMC from Alzheimer's disease patient at 0.1 uM by flow cytometry	2007	Proceedings of the National Academy of Sciences of the United States of America, Jul-31, Volume: 104, Issue:31	Innate immunity and transcription of MGAT-III and Toll-like receptors in Alzheimer's disease patients are improved by bisdemethoxycurcumin.
AID1333299	Growth inhibition of CHOK1 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID466920	Antileishmanial activity against Leishmania major Friedlin promastigotes after 48 hrs by alamar blue assay	2010	European journal of medicinal chemistry, Mar, Volume: 45, Issue:3	Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID754248	Effect on orthotopic tumor mass in human MDA-MB-231 cells xenografted athymic nude mouse left cardiac ventricle at 25 to 50 mg/kg, ip administered every other day for 3 weeks	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID754258	Inhibition of TGF-beta-induced Smad3 phosphorylation in human MDA-MB-231 cells treated 12 hrs before TGF-beta challenge measured after 1 hr by Western blotting	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
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.
AID106581	Compound concentration required to reduce the exponential growth of MT-4 cells by 50%	1998	Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21	Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: synthesis, biological evaluation, and molecular modeling.
AID466919	Antitrypanosomal activity against multidrug-resistant Trypanosoma brucei brucei B48 after 48 hrs by alamar blue assay	2010	European journal of medicinal chemistry, Mar, Volume: 45, Issue:3	Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID754247	Toxicity in human MDA-MB-231 cells xenografted athymic nude mouse left cardiac ventricle assessed as effect on liver weight at 25 mg/kg, ip administered every other day for 3 weeks (Rvb = 1 +/- 0.10 gram)	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID754250	Inhibition of osteolytic bone metastases in human MDA-MB-231 cells xenografted in athymic nude mouse left cardiac ventricle assessed as reduction of bone lysis at 25 to 50 mg/kg, ip administered every other day for 3 weeks measured on day 21	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID418000	Antiproliferative activity against human LNCAP cells after 72 hrs by MTT assay	2009	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7	Structure-activity relationship studies of curcumin analogues.
AID376765	Inhibition of topoisomerase 1 in Saccharomyces cerevisiae JN394t2-5 assessed as inhibition of growth at 50 ug/mL after 72 hrs	1998	Journal of natural products, Apr, Volume: 61, Issue:4	Novel bioactivities of Curcuma longa constituents.
AID247571	Anti-oxidant activity in DPPH radicak scavenging assay; n=3-4	2005	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 15, Issue:7	Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammatory agents.
AID754252	Inhibition of osteolytic bone metastases in human MDA-MB-231 cells xenografted in athymic nude mouse left cardiac ventricle assessed as reduction of bone-tumor interface at 50 mg/kg, ip administered every other day for 3 weeks	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID328874	Increase in TLR3 protein expression in PBMC from Alzheimer's disease patient at 0.1 uM by flow cytometry	2007	Proceedings of the National Academy of Sciences of the United States of America, Jul-31, Volume: 104, Issue:31	Innate immunity and transcription of MGAT-III and Toll-like receptors in Alzheimer's disease patients are improved by bisdemethoxycurcumin.
AID1333306	Growth inhibition of differentiated human Caco2 cells measured after 72 hrs by SRB assay	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID1330226	Cytotoxicity against CHOK1 cells assessed as decrease in cell viability after 48 hrs by MTT assay	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID1175312	Inhibition of amyloid beta-42 self-aggregation (unknown origin) at 25 uM after 20 hrs by ThT fluorescence assay	2014	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 24, Issue:24	Structure activity relationship study of curcumin analogues toward the amyloid-beta aggregation inhibitor.
AID367264	Inhibition of C1226 catalytic site of DNMT1	2009	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3	Curcumin is a potent DNA hypomethylation agent.
AID1395722	Cytotoxicity against human MCF7 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay	2018	European journal of medicinal chemistry, May-10, Volume: 151	Antiproliferative efficacy of curcumin mimics through microtubule destabilization.
AID402709	Cytotoxicity against human HL60	2005	Journal of natural products, Jul, Volume: 68, Issue:7	A labdane diterpene glucoside from the rhizomes of Curcuma mangga.
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.
AID1168664	Activation of human telomerase activity expressed in HEK293T cells incubated for 30 mins by modified TRAP assay	2014	Bioorganic & medicinal chemistry letters, Nov-15, Volume: 24, Issue:22	Curcuminoid derivatives enhance telomerase activity in an in vitro TRAP assay.
AID754261	Inhibition of TGF-beta-induced PTHrP secretion in human MDA-MB-231 cells at 100 uM treated 4 hrs before TGF-beta challenge measured after 24 hrs by radioimmunoassay	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID1154169	Cytotoxicity against human KB cells assessed as growth inhibition by resazurin microplate assay	2014	Bioorganic & medicinal chemistry letters, Jul-01, Volume: 24, Issue:13	Synthesis, cytotoxicity against human oral cancer KB cells and structure-activity relationship studies of trienone analogues of curcuminoids.
AID1333312	Effect on oxidative stress in CHO cells assessed as intracellular ROS level at 10 uM after overnight incubation by DCFH-DA staining based fluorescence assay relative to control	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID399390	Antiplatelet activity in human whole blood assessed as inhibition of ristocetin-induced platelet aggregation at 100 ug/mL relative to control	1998	Journal of natural products, Jan, Volume: 61, Issue:1	A new antiplatelet diarylheptanoid from Alpinia blepharocalyx.
AID1330213	Aqueous solubility of the compound in sodium phosphate buffer at pH 6.8 after 90 mins by shake flask method	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID568008	Inhibition of human recombinant His-tagged glyoxalase 1 expressed in Escherichia coli BL21 (DE3) preincubated for 20 mins by Dixon plot analysis	2011	Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3	Identification of curcumin derivatives as human glyoxalase I inhibitors: A combination of biological evaluation, molecular docking, 3D-QSAR and molecular dynamics simulation studies.
AID1333317	Effect on oxidative stress in human EAhy926 cells assessed as intracellular ROS level at 10 uM after overnight incubation by DCFH-DA staining based fluorescence assay relative to control	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID1330231	Induction of ROS generation in human HepG2 cells at 10 uM using DCFH-DA by fluorescence assay relative to control	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID754256	Inhibition of TGF-beta-induced p38 phosphorylation in human MDA-MB-231 cells treated 12 hrs before TGF-beta challenge measured after 1 hr by Western blotting	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID1198250	Cytotoxicity against human MCF7/6 cells at 10 umol/l	2015	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 25, Issue:5	Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids.
AID1126926	Reduction in Flt3 protein level in human EOL-1 cells at 15 uM after 48 hrs by Western blot analysis	2014	Journal of natural products, Apr-25, Volume: 77, Issue:4	Inhibitory effect of turmeric curcuminoids on FLT3 expression and cell cycle arrest in the FLT3-overexpressing EoL-1 leukemic cell line.
AID1465694	Inhibition of AKR1B1 (unknown origin)	2017	Journal of medicinal chemistry, 10-26, Volume: 60, Issue:20	Synthesis of Potent and Selective Inhibitors of Aldo-Keto Reductase 1B10 and Their Efficacy against Proliferation, Metastasis, and Cisplatin Resistance of Lung Cancer Cells.
AID754237	Toxicity in human MDA-MB-231 cells xenografted athymic nude mouse left cardiac ventricle assessed as effect on alanine aminotransferase at 25 mg/kg, ip administered every other day for 3 weeks (Rvb = 7.04 +/- 2.2 U/L)	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID754245	Toxicity in human MDA-MB-231 cells xenografted athymic nude mouse left cardiac ventricle assessed as effect on spleen weight at 25 mg/kg, ip administered every other day for 3 weeks (Rvb = 0.134 +/- 0.02 gram)	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID1330215	Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins by spectrophotometric analysis	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID402712	Cytotoxicity against human DU145	2005	Journal of natural products, Jul, Volume: 68, Issue:7	A labdane diterpene glucoside from the rhizomes of Curcuma mangga.
AID1511039	Decrease in UPA expression in human HT1080 cells	2019	European journal of medicinal chemistry, Oct-15, Volume: 180	Recent advances of analogues of curcumin for treatment of cancer.
AID1330227	Cytotoxicity against human EAhy926 cells assessed as decrease in cell viability after 48 hrs by MTT assay	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID754241	Toxicity in human MDA-MB-231 cells xenografted athymic nude mouse left cardiac ventricle assessed as effect on white blood cells at 25 mg/kg, ip administered every other day for 3 weeks (Rvb = 35.84 +/- 1.3 K/uL)	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID376495	Inhibition of topoisomerase 1 in Saccharomyces cerevisiae JN394t-1 assessed as inhibition of growth at 25 ug/mL after 72 hrs	1998	Journal of natural products, Apr, Volume: 61, Issue:4	Novel bioactivities of Curcuma longa constituents.
AID754243	Toxicity in human MDA-MB-231 cells xenografted athymic nude mouse left cardiac ventricle assessed as effect on hematocrit at 25 mg/kg, ip administered every other day for 3 weeks (Rvb = 30.2 +/- 1.5%)	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID747035	Inhibition of electric eel AChE using acetylthiocholine iodide as substrate after 15 mins by Ellman's method	2013	Bioorganic & medicinal chemistry letters, May-15, Volume: 23, Issue:10	Novel racemic tetrahydrocurcuminoid dihydropyrimidinone analogues as potent acetylcholinesterase inhibitors.
AID1333305	Growth inhibition of differentiated human Caco2 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID1348957	Activation of Nrf2 (unknown origin) expressed in human HepG2 cells at 15 uM after 5 hrs by ARE-driven luciferase reporter gene assay relative to control	2018	European journal of medicinal chemistry, Jan-01, Volume: 143	Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin.
AID402711	Cytotoxicity against human MCF7	2005	Journal of natural products, Jul, Volume: 68, Issue:7	A labdane diterpene glucoside from the rhizomes of Curcuma mangga.
AID1198245	Antiinvasive activity against human MCF7/6 cells precultured with 9 day old chick embryo heart tissue fragment at 1 micromol/l by chick heart invasion assay	2015	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 25, Issue:5	Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids.
AID1333316	Effect on oxidative stress in human HT-29 cells assessed as intracellular ROS level at 10 uM after overnight incubation by DCFH-DA staining based fluorescence assay relative to control	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID1586747	Drug metabolism assessed as horseradish peroxidase-mediated oxidation by measuring bisdemethoxy-7-Norcyclopentadione formation at 50 uM after 1 hr in presence of H2O2 by LC-MS analysis	2018	Journal of natural products, 12-28, Volume: 81, Issue:12	A Curcumin Degradation Product, 7-Norcyclopentadione, Formed by Aryl Migration and Loss of a Carbon from the Heptadienedione Chain.
AID1333315	Effect on oxidative stress in human HT-29 cells assessed as intracellular ROS level at 1 uM after overnight incubation by DCFH-DA staining based fluorescence assay relative to control	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID93515	Inhibition of 3'- processing activity of HIV-1 integrase	1997	Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19	Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action.
AID402710	Cytotoxicity against human HepG2	2005	Journal of natural products, Jul, Volume: 68, Issue:7	A labdane diterpene glucoside from the rhizomes of Curcuma mangga.
AID560228	Inhibition of GFP-tagged Candida albicans CDR1 expressed in Saccharomyces cerevisiae assessed as inhibition of R6G efflux	2009	Antimicrobial agents and chemotherapy, Aug, Volume: 53, Issue:8	Curcumin modulates efflux mediated by yeast ABC multidrug transporters and is synergistic with antifungals.
AID1198246	Antiinvasive activity against human MCF7/6 cells precultured with 9 day old chick embryo heart tissue fragment at 0.1 micromol/l by chick heart invasion assay	2015	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 25, Issue:5	Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids.
AID1330223	Cytotoxicity against human Caco2 cells assessed as decrease in cell viability after 48 hrs by MTT assay	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID754239	Toxicity in human MDA-MB-231 cells xenografted athymic nude mouse left cardiac ventricle assessed as effect on platelets at 25 mg/kg, ip administered every other day for 3 weeks (Rvb = 513 +/- 54 K/uL)	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID1333314	Effect on oxidative stress in undifferentiated human Caco2 cells assessed as intracellular ROS level at 10 uM after overnight incubation by DCFH-DA staining based fluorescence assay relative to control	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID754254	Inhibition of osteolytic bone metastases in human MDA-MB-231 cells xenografted in athymic nude mouse left cardiac ventricle assessed as reduction in lytic bone lesion area at 25 to 50 mg/kg, ip administered every other day for 3 weeks measured on day 21 r	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID1511038	Increase in MMP3 level in human MDA-MB-231 cells after 24 hrs by ELISA	2019	European journal of medicinal chemistry, Oct-15, Volume: 180	Recent advances of analogues of curcumin for treatment of cancer.
AID1348958	Effect on firefly luciferase activity expressed in human HepG2 cells at low concentration after 5 hrs by luminescence assay	2018	European journal of medicinal chemistry, Jan-01, Volume: 143	Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin.
AID1126925	Reduction in Flt3 protein level in human EOL-1 cells at 15 uM after 24 hrs by Western blot analysis	2014	Journal of natural products, Apr-25, Volume: 77, Issue:4	Inhibitory effect of turmeric curcuminoids on FLT3 expression and cell cycle arrest in the FLT3-overexpressing EoL-1 leukemic cell line.
AID1062642	Inhibition of Wnt3A/beta-catenin signaling in HEK293 cells at 20 uM after 24 hrs by firefly/renilla dual luciferase reporter gene assay relative to vehicle-treated control	2014	European journal of medicinal chemistry, Jan, Volume: 71	Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway.
AID376500	Inhibition of topoisomerase 1 in Saccharomyces cerevisiae JN394 assessed as inhibition of growth at 50 ug/mL after 72 hrs	1998	Journal of natural products, Apr, Volume: 61, Issue:4	Novel bioactivities of Curcuma longa constituents.
AID364862	Inhibition of TrxR preincuabatd for 2 mins	2008	Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17	Synthesis and evaluation of curcumin analogues as potential thioredoxin reductase inhibitors.
AID1330225	Cytotoxicity against human HT-29 cells assessed as decrease in cell viability after 48 hrs by MTT assay	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID1330228	Induction of ROS generation in human Caco2 cells at 1 uM using DCFH-DA by fluorescence assay relative to control	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID376496	Inhibition of topoisomerase 1 in Saccharomyces cerevisiae JN394t2-5 assessed as inhibition of growth at 25 ug/mL after 72 hrs	1998	Journal of natural products, Apr, Volume: 61, Issue:4	Novel bioactivities of Curcuma longa constituents.
AID376767	Inhibition of topoisomerase 2 in Saccharomyces cerevisiae JN394t-1 assessed as inhibition of growth at 50 ug/mL after 72 hrs	1998	Journal of natural products, Apr, Volume: 61, Issue:4	Novel bioactivities of Curcuma longa constituents.
AID1062645	Inhibition of Wnt3A/beta-catenin signaling in HEK293 cells at 1 uM after 24 hrs by firefly/renilla dual luciferase reporter gene assay relative to vehicle-treated control	2014	European journal of medicinal chemistry, Jan, Volume: 71	Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway.
AID492140	Antioxidant activity assessed as formazan formation induced absorbance changes at 25 ppm at 570 nm at 37 degC for 6 hrs by MTT assay	2010	Journal of natural products, Jul-23, Volume: 73, Issue:7	An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds.
AID1333311	Effect on oxidative stress in CHO cells assessed as intracellular ROS level at 1 uM after overnight incubation by DCFH-DA staining based fluorescence assay relative to control	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID1395723	Cytotoxicity against human DLD1 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay	2018	European journal of medicinal chemistry, May-10, Volume: 151	Antiproliferative efficacy of curcumin mimics through microtubule destabilization.
AID1330236	Induction of ROS generation in human EAhy926 cells at 1 uM using DCFH-DA by fluorescence assay relative to control	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID1062643	Inhibition of Wnt3A/beta-catenin signaling in HEK293 cells at 10 uM after 24 hrs by firefly/renilla dual luciferase reporter gene assay relative to vehicle-treated control	2014	European journal of medicinal chemistry, Jan, Volume: 71	Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway.
AID399389	Antiplatelet activity in human whole blood assessed as inhibition of arachidonic acid-induced platelet aggregation at 100 ug/mL relative to control	1998	Journal of natural products, Jan, Volume: 61, Issue:1	A new antiplatelet diarylheptanoid from Alpinia blepharocalyx.
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.
AID1333310	Effect on oxidative stress in human EAhy926 cells assessed as intracellular ROS level at 1 uM after overnight incubation by DCFH-DA staining based fluorescence assay relative to control	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID604299	Inhibition of human glyoxalase 1	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Structural investigation into the inhibitory mechanisms of indomethacin and its analogues towards human glyoxalase I.
AID335875	Protection against beta-amyloid (25 to 35) insult in rat PC12 cells assessed as viable cells after 24 hrs by MTT assay	2002	Journal of natural products, Sep, Volume: 65, Issue:9	Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: a drug discovery effort against Alzheimer's disease.
AID754249	Toxicity in human MDA-MB-231 cells xenografted athymic nude mouse left cardiac ventricle assessed as effect on bone-forming osteoblast cell at 25 to 50 mg/kg, ip administered every other day for 3 weeks	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID93381	Compound concentration required to reduce HIV-1 Integrase 3'-processing activity by 50%	1998	Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21	Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: synthesis, biological evaluation, and molecular modeling.
AID328870	Induction of amyloid beta phagocytosis in macrophages from Alzheimer's disease patient at 0.1 uM	2007	Proceedings of the National Academy of Sciences of the United States of America, Jul-31, Volume: 104, Issue:31	Innate immunity and transcription of MGAT-III and Toll-like receptors in Alzheimer's disease patients are improved by bisdemethoxycurcumin.
AID754238	Toxicity in human MDA-MB-231 cells xenografted athymic nude mouse left cardiac ventricle assessed as effect on platelets at 50 mg/kg, ip administered every other day for 3 weeks (Rvb = 513 +/- 54 K/uL)	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID687453	Inhibition of alphaCaMK2 using GST-NR2A as substrate incubated for 1 min prior to substrate addition measured after 1 min	2012	Bioorganic & medicinal chemistry, Oct-15, Volume: 20, Issue:20	Curcumin is an inhibitor of calcium/calmodulin dependent protein kinase II.
AID1330230	Induction of ROS generation in human HepG2 cells at 1 uM using DCFH-DA by fluorescence assay relative to control	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID418001	Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay	2009	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7	Structure-activity relationship studies of curcumin analogues.
AID754259	Inhibition of TGF-beta-induced Smad2 phosphorylation in human MDA-MB-231 cells treated 12 hrs before TGF-beta challenge measured after 1 hr by Western blotting	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID1330233	Induction of ROS generation in human HT-29 cells at 10 uM using DCFH-DA by fluorescence assay relative to control	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID1154170	Cytotoxicity against african green monkey Vero cells by green fluorescent protein detection method	2014	Bioorganic & medicinal chemistry letters, Jul-01, Volume: 24, Issue:13	Synthesis, cytotoxicity against human oral cancer KB cells and structure-activity relationship studies of trienone analogues of curcuminoids.
AID1465693	Inhibition of AKR1B10 (unknown origin)	2017	Journal of medicinal chemistry, 10-26, Volume: 60, Issue:20	Synthesis of Potent and Selective Inhibitors of Aldo-Keto Reductase 1B10 and Their Efficacy against Proliferation, Metastasis, and Cisplatin Resistance of Lung Cancer Cells.
AID399387	Antiplatelet activity in human whole blood assessed as inhibition of collagen-induced platelet aggregation at 100 ug/mL relative to control	1998	Journal of natural products, Jan, Volume: 61, Issue:1	A new antiplatelet diarylheptanoid from Alpinia blepharocalyx.
AID399388	Antiplatelet activity in human whole blood assessed as inhibition of ADP-induced platelet aggregation at 100 ug/mL relative to control	1998	Journal of natural products, Jan, Volume: 61, Issue:1	A new antiplatelet diarylheptanoid from Alpinia blepharocalyx.
AID754246	Toxicity in human MDA-MB-231 cells xenografted athymic nude mouse left cardiac ventricle assessed as effect on liver weight at 50 mg/kg, ip administered every other day for 3 weeks (Rvb = 1 +/- 0.10 gram)	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID466918	Antitrypanosomal activity against diminazene-resistant Trypanosoma brucei brucei deltaTbat1-KO after 48 hrs by alamar blue assay	2010	European journal of medicinal chemistry, Mar, Volume: 45, Issue:3	Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID1333313	Effect on oxidative stress in undifferentiated human Caco2 cells assessed as intracellular ROS level at 1 uM after overnight incubation by DCFH-DA staining based fluorescence assay relative to control	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID1333308	Growth inhibition of human EAhy926 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID96213	Fold increase in protein-linked DNA breaks (PLDB) with respect to untreated controls.	1998	Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21	Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: synthesis, biological evaluation, and molecular modeling.
AID1333307	Growth inhibition of human HT-29 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID1330238	Chemical stability of the compound sodium phosphate buffer at pH 6.8 after 24 hrs by LC-MS analysis	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID1333302	Growth inhibition of human HT-29 cells measured after 72 hrs by SRB assay	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID717733	Cytotoxicity against human A549 cells after 72 hrs by crystal violet staining based microplate reader analysis	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Terpecurcumins A-I from the rhizomes of Curcuma longa: absolute configuration and cytotoxic activity.
AID328871	Upregulation of MGAT3 transcription in PBMC from Alzheimer's disease patient	2007	Proceedings of the National Academy of Sciences of the United States of America, Jul-31, Volume: 104, Issue:31	Innate immunity and transcription of MGAT-III and Toll-like receptors in Alzheimer's disease patients are improved by bisdemethoxycurcumin.
AID1126918	Cytotoxicity against human EOL-1 cells after 48 hrs by MTT assay	2014	Journal of natural products, Apr-25, Volume: 77, Issue:4	Inhibitory effect of turmeric curcuminoids on FLT3 expression and cell cycle arrest in the FLT3-overexpressing EoL-1 leukemic cell line.
AID376498	Inhibition of topoisomerase 2 in Saccharomyces cerevisiae JN394t-1 assessed as inhibition of growth at 25 ug/mL after 72 hrs	1998	Journal of natural products, Apr, Volume: 61, Issue:4	Novel bioactivities of Curcuma longa constituents.
AID466917	Antitrypanosomal activity against Trypanosoma brucei brucei 427 after 48 hrs by alamar blue assay	2010	European journal of medicinal chemistry, Mar, Volume: 45, Issue:3	Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID1198248	Antiinvasive activity against human MCF7/6 cells precultured with 9 day old chick embryo heart tissue fragment assessed as lowest concentration by chick heart invasion assay	2015	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 25, Issue:5	Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids.
AID1330224	Cytotoxicity against human HepG2 cells assessed as decrease in cell viability after 48 hrs by MTT assay	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID1330232	Induction of ROS generation in human HT-29 cells at 1 uM using DCFH-DA by fluorescence assay relative to control	2016	Bioorganic & medicinal chemistry letters, 12-01, Volume: 26, Issue:23	Synthesis and biological assessment of novel N-(hydroxy/methoxy)alkyl β-enaminone curcuminoids.
AID604088	Antioxidant activity assessed as DPPH radical scavenging activity	2011	Bioorganic & medicinal chemistry, Jun-15, Volume: 19, Issue:12	Significant enhancement in radical-scavenging activity of curcuminoids conferred by acetoxy substituent at the central methylene carbon.
AID376499	Inhibition of topoisomerase 2 in Saccharomyces cerevisiae JN394t2-5 assessed as inhibition of growth at 25 ug/mL after 72 hrs	1998	Journal of natural products, Apr, Volume: 61, Issue:4	Novel bioactivities of Curcuma longa constituents.
AID717732	Cytotoxicity against human MDA-MB-231 cells after 72 hrs by crystal violet staining based microplate reader analysis	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Terpecurcumins A-I from the rhizomes of Curcuma longa: absolute configuration and cytotoxic activity.
AID328875	Increase in TLR4 protein expression in PBMC from Alzheimer's disease patient at 0.1 uM by flow cytometry	2007	Proceedings of the National Academy of Sciences of the United States of America, Jul-31, Volume: 104, Issue:31	Innate immunity and transcription of MGAT-III and Toll-like receptors in Alzheimer's disease patients are improved by bisdemethoxycurcumin.
AID466922	Cytotoxicity against HEK293 cells after 16 hrs by alamar blue assay	2010	European journal of medicinal chemistry, Mar, Volume: 45, Issue:3	Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID91579	Inhibitory activity against HIV-1 Integrase (HIV-1-IN)	2002	Journal of medicinal chemistry, Feb-14, Volume: 45, Issue:4	CoMFA and CoMSIA 3D QSAR and docking studies on conformationally-restrained cinnamoyl HIV-1 integrase inhibitors: exploration of a binding mode at the active site.
AID1198243	Antiinvasive activity against human MCF7/6 cells precultured with 9 day old chick embryo heart tissue fragment at 100 micromol/l by chick heart invasion assay	2015	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 25, Issue:5	Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids.
AID754257	Inhibition of TGF-beta-induced Ets-1 expression in human MDA-MB-231 cells treated 18 hrs before TGF-beta challenge measured after 1 hr by Western blotting	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID1333300	Antioxidant activity assessed as trolox equivalent of ferric ion reducing activity using Fe3+-TPTZ by measuring Fe2+-TPTZ formation after 4 mins by UV-vis spectrophotometry based FRAP assay	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID754253	Inhibition of osteolytic bone metastases in human MDA-MB-231 cells xenografted in athymic nude mouse left cardiac ventricle assessed as reduction of bone-tumor interface at 25 mg/kg, ip administered every other day for 3 weeks	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID754236	Toxicity in human MDA-MB-231 cells xenografted athymic nude mouse left cardiac ventricle assessed as effect on alanine aminotransferase at 50 mg/kg, ip administered every other day for 3 weeks (Rvb = 7.04 +/- 2.2 U/L)	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID418002	Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by MTT assay	2009	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7	Structure-activity relationship studies of curcumin analogues.
AID243855	Percent inhibition against Prostaglandin G/H synthase 2 from sheep placenta at 100 uM	2005	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 15, Issue:7	Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammatory agents.
AID417999	Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay	2009	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7	Structure-activity relationship studies of curcumin analogues.
AID367266	Inhibition of Spiroplasma sp. MQ-1 M.SssI	2009	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3	Curcumin is a potent DNA hypomethylation agent.
AID328872	Upregulation of TLR transcription in PBMC from Alzheimer's disease patient	2007	Proceedings of the National Academy of Sciences of the United States of America, Jul-31, Volume: 104, Issue:31	Innate immunity and transcription of MGAT-III and Toll-like receptors in Alzheimer's disease patients are improved by bisdemethoxycurcumin.
AID93530	Inhibition of strand transfer activity of HIV-1 integrase	1997	Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19	Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action.
AID754242	Toxicity in human MDA-MB-231 cells xenografted athymic nude mouse left cardiac ventricle assessed as effect on hematocrit at 50 mg/kg, ip administered every other day for 3 weeks (Rvb = 30.2 +/- 1.5%)	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID335876	Protection against beta-amyloid (1 to 42) insult in rat PC12 cells assessed as viable cells after 24 hrs by MTT assay	2002	Journal of natural products, Sep, Volume: 65, Issue:9	Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: a drug discovery effort against Alzheimer's disease.
AID1333309	Growth inhibition of human EAhy926 cells measured after 72 hrs by SRB assay	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID754235	Inhibition of osteolytic bone metastases in human MDA-MB-231 cells xenografted in athymic nude mouse left cardiac ventricle assessed as improvement in host survival at 25 to 50 mg/kg, ip administered every other day for 3 weeks measured on day 16 relative	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID376501	Inhibition of topoisomerase 1 in Saccharomyces cerevisiae JN394t-1 assessed as inhibition of growth at 50 ug/mL after 72 hrs	1998	Journal of natural products, Apr, Volume: 61, Issue:4	Novel bioactivities of Curcuma longa constituents.
AID1333297	Solubility of the compound in serum-free DMEM assessed as compound concentration required for crystal formation measured after 1 day by microscopic analysis	2016	European journal of medicinal chemistry, Nov-10, Volume: 123	Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress.
AID754234	Inhibition of osteolytic bone metastases in human MDA-MB-231 cells xenografted in athymic nude mouse left cardiac ventricle assessed as improvement in body weight at 25 to 50 mg/kg, ip administered every other day for 3 weeks measured on day 16 relative t	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Curcuminoids block TGF-β signaling in human breast cancer cells and limit osteolysis in a murine model of breast cancer bone metastasis.
AID1794808	Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).	2014	Journal of biomolecular screening, Jul, Volume: 19, Issue:6	A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808	Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	9 (3.96)	18.2507
2000's	44 (19.38)	29.6817
2010's	137 (60.35)	24.3611
2020's	37 (16.30)	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	11 (4.62%)	5.53%
Reviews	6 (2.52%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	221 (92.86%)	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
4-hydroxybenzaldehyde [no description available]	2.43	2	0	hydroxybenzaldehyde	EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor; 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.	2.05	1	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	2.31	1	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
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.	2.04	1	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
choline [no description available]	2.13	1	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
3-methylcatechol 3-methylbenzene-1,2-diol: structure in first source. dihydroxytoluene : Any hydroxytoluene that has two hydroxy substituents. 3-methylcatechol : A methylcatechol carrying a methyl substituent at position 3. It is a xenobiotic metabolite produced by some bacteria capable of degrading nitroaromatic compounds present in pesticide-contaminated soil samples.	2.05	1	0	methylcatechol	bacterial xenobiotic 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.	2.05	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.	2.07	1	0	aminophenol	allergen; metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.15	1	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	2.08	1	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
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
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.	3.31	6	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
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)	2.11	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
pyrogallol benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.	2.05	1	0	benzenetriol; phenolic donor	plant metabolite
sulfuric acid sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.	2.04	1	0	sulfur oxoacid	catalyst
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	2.46	2	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
epibatidine [no description available]	2.07	1	0	alkaloid
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.	2.01	1	0	hydrazines	alkylating agent; carcinogenic agent
2,4-dinitrophenol 2,4-Dinitrophenol: A toxic dye, chemically related to trinitrophenol (picric acid), used in biochemical studies of oxidative processes where it uncouples oxidative phosphorylation. It is also used as a metabolic stimulant. (Stedman, 26th ed). dinitrophenol : Members of the class of nitrophenol carrying two nitro substituents.. 2,4-dinitrophenol : A dinitrophenol having the nitro groups at the 2- and 4-positions.	2.15	1	0	dinitrophenol	allergen; antiseptic drug; bacterial xenobiotic metabolite; geroprotector; oxidative phosphorylation inhibitor
amitrole Amitrole: A non-selective post-emergence, translocated herbicide. According to the Seventh Annual Report on Carcinogens (PB95-109781, 1994) this substance may reasonably be anticipated to be a carcinogen. (From Merck Index, 12th ed) It is an irreversible inhibitor of CATALASE, and thus impairs activity of peroxisomes.. amitrole : A member of the class of triazoles that is 1H-1,2,4-triazole substituted by an amino group at position 3. Used to control annual grasses and aquatic weeds (but not on food crops because it causes cancer in laboratory animals). Its use within the EU was banned from September 2017 on the grounds of potential groundwater contamination and risks to aquatic life; there have also been concerns about its endocrine-disrupting properties.	1.99	1	0	aromatic amine; triazoles	carotenoid biosynthesis inhibitor; EC 1.11.1.6 (catalase) inhibitor; herbicide
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
2,2'-azobis(2-amidinopropane) 2,2'-azobis(2-amidinopropane): water-soluble free-radical initiator	2.03	1	0	monoazo compound
acemetacin acemetacin : A carboxylic ester that is the carboxymethyl ester of indometacin. A non-steroidal anti-inflammatory drug, it is used in the treatment of rheumatoid arthritis, osteoarthritis, and low back pain, as well as for postoperative pain and inflammation. Its activity is due to both acemetacin and its major metabolite, indometacin.	2.06	1	0	carboxylic ester; indol-3-yl carboxylic acid; monocarboxylic acid; monochlorobenzenes; N-acylindole	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
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
diminazene Diminazene: An effective trypanocidal agent.. diminazene : A triazene derivative that is triazene in which each of the terminal nitrogens is substituted by a 4-carbamimidoylphenyl group.	2.05	1	0	carboxamidine; triazene derivative	antiparasitic agent; trypanocidal drug
5-methoxypsoralen 5-Methoxypsoralen: A linear furanocoumarin that has phototoxic and anti-inflammatory properties, with effects similar to METHOXSALEN. It is used in PUVA THERAPY for the treatment of PSORIASIS.. 5-methoxypsoralen : A 5-methoxyfurocoumarin that is psoralen substituted by a methoxy group at position 5.	2.07	1	0	5-methoxyfurocoumarin; organic heterotricyclic compound; psoralens	hepatoprotective agent; plant metabolite
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.	2.15	1	0	aromatic ether; nitrile; polyether; tertiary amino compound
celecoxib [no description available]	2.02	1	0	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory 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.	2.05	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
deferoxamine Deferoxamine: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form.. desferrioxamine B : An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.	2.15	1	0	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
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
ellipticine ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.	2.49	2	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.	2.07	1	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.	2.02	1	0
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.	2.47	2	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; non-narcotic analgesic; non-steroidal anti-inflammatory drug
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	2.17	1	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
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
hypericin [no description available]	2.07	1	0
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	2.02	1	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
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.	2.72	3	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
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).	2.05	1	0	carbohydrazide	antitubercular agent; drug allergen
itraconazole [no description available]	2.05	1	0	piperazines
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
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.	2.05	1	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.	2.47	2	0	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
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
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.	2.05	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
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	2.21	1	0	chromones; morpholines; organochlorine compound	autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector
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
methacrylic acid methacrylic acid: RN given refers to parent cpd. methacrylic acid : An alpha,beta-unsaturated monocarboxylic acid that is acrylic acid in which the hydrogen at position 2 is substituted by a methyl group.	2.04	1	0	alpha,beta-unsaturated monocarboxylic acid
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.	2.07	1	0	aromatic ether; psoralens	antineoplastic agent; cross-linking reagent; dermatologic drug; photosensitizing agent; plant metabolite
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
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
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'.	2.21	1	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
pentamidine Pentamidine: Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.. pentamidine : A diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease.	2.05	1	0	aromatic ether; carboxamidine; diether	anti-inflammatory agent; antifungal agent; calmodulin antagonist; chemokine receptor 5 antagonist; EC 2.3.1.48 (histone acetyltransferase) inhibitor; NMDA receptor antagonist; S100 calcium-binding protein B inhibitor; trypanocidal drug; xenobiotic
phloretin [no description available]	2.07	1	0	dihydrochalcones	antineoplastic agent; plant metabolite
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.	2.02	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.	2.15	1	0	benzoic acids; sulfonamide	uricosuric drug
sanguinarine benzophenanthridine alkaloid : A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.	2.07	1	0	alkaloid antibiotic; benzophenanthridine alkaloid; botanical anti-fungal agent
stearic acid octadecanoic acid : A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.	2.05	1	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
streptonigrin [no description available]	2.07	1	0	pyridines; quinolone	antimicrobial agent; antineoplastic agent
tetrahydropapaverine tetrahydropapaverine: RN given refers to parent cpd. 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline : A benzylisoquinoline alkaloid that is norlaudanosoline in which the four phenolic hydrogens have been replaced by methyl groups.	2.07	1	0	aromatic ether; benzylisoquinoline alkaloid; benzyltetrahydroisoquinoline; polyether; secondary amino compound
theobromine Theobromine: 3,7-Dimethylxanthine. The principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than THEOPHYLLINE and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9). theobromine : A dimethylxanthine having the two methyl groups located at positions 3 and 7. A purine alkaloid derived from the cacao plant, it is found in chocolate, as well as in a number of other foods, and is a vasodilator, diuretic and heart stimulator.	2.07	1	0	dimethylxanthine	adenosine receptor antagonist; bronchodilator agent; food component; human blood serum metabolite; mouse metabolite; plant metabolite; vasodilator agent
tolmetin Tolmetin: A non-steroidal anti-inflammatory agent (ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL) similar in mode of action to INDOMETHACIN.. tolmetin : A monocarboxylic acid that is (1-methylpyrrol-2-yl)acetic acid substituted at position 5 on the pyrrole ring by a 4-methylbenzoyl group. Used in the form of its sodium salt dihydrate as a nonselective nonsteroidal anti-inflammatory drug.	2.47	2	0	aromatic ketone; monocarboxylic acid; pyrroles	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
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
zomepirac zomepirac: RN given refers to parent cpd; structure	2.47	2	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.	2.07	1	0	mitomycin	alkylating agent; antineoplastic agent
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.	2.07	1	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
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
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	2.44	2	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
cantharidin Cantharidin: A toxic compound, isolated from the Spanish fly or blistering beetle (Lytta (Cantharis) vesicatoria) and other insects. It is a potent and specific inhibitor of protein phosphatases 1 (PP1) and 2A (PP2A). This compound can produce severe skin inflammation, and is extremely toxic if ingested orally.. cantharidin : A monoterpenoid with an epoxy-bridged cyclic dicarboxylic anhydride structure secreted by many species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria. Natural toxin inhibitor of protein phosphatases 1 and 2A.	2.07	1	0	cyclic dicarboxylic anhydride; monoterpenoid	EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; herbicide
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	2.05	1	0	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
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
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	1.98	1	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
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.	2.47	2	0	kanamycins	bacterial 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.	2.15	1	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	2.15	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
veratramine veratramine: structure. veratramine : A piperidine alkaloid comprising the 14,15,16,17-tetradehydro derivative of veratraman having two hydroxy groups at the 3- and 23-positions.	2.07	1	0	piperidine alkaloid
phlorhizin [no description available]	2.07	1	0	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	antioxidant; plant metabolite
papaverine hydrochloride [no description available]	2.07	1	0
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	2.13	1	0	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
colchicine (S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.	2.52	2	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
chloroform Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.	2.04	1	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
gliotoxin Gliotoxin: A fungal toxin produced by various species of Trichoderma, Gladiocladium fimbriatum, Aspergillus fumigatus, and Penicillium. It is used as an immunosuppressive agent.. gliotoxin : A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi.	2.07	1	0	dipeptide; organic disulfide; organic heterotetracyclic compound; pyrazinoindole	antifungal agent; EC 2.5.1.58 (protein farnesyltransferase) inhibitor; immunosuppressive agent; mycotoxin; proteasome inhibitor
tubercidin Tubercidin: An antibiotic purine ribonucleoside that readily substitutes for adenosine in the biological system, but its incorporation into DNA and RNA has an inhibitory effect on the metabolism of these nucleic acids.. tubercidin : An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus.	2.07	1	0	antibiotic antifungal agent; N-glycosylpyrrolopyrimidine; ribonucleoside	antimetabolite; antineoplastic agent; bacterial metabolite
veratridine [no description available]	2.07	1	0	steroid	sodium channel modulator
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	2.05	1	0	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
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.	2.01	1	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2.06	1	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
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
methacrylamide [no description available]	2.04	1	0	acrylamides; primary carboxamide
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
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
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
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.05	1	0	alkane
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	2.13	1	0	cyclohexanols; secondary alcohol	solvent
pelargonic acid pelargonic acid: K salt acts as cariostatic agent; RN given refers to parent cpd; structure. nonanoic acid : A C9 straight-chain saturated fatty acid which occurs naturally as esters of the oil of pelargonium. Has antifungal properties, and is also used as a herbicide as well as in the preparation of plasticisers and lacquers.	2.05	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antifeedant; Daphnia magna metabolite; plant metabolite
undecanoic acid undecanoic acid : A straight-chain, eleven-carbon saturated medium-chain fatty acid found in body fluids; the most fungitoxic of the C7:0 - C18:0 fatty acid series.. undecanoate : A medium-chain fatty acid anion that is the conjugate base of undecanoic acid; used in tandem with testosterone cation in the treatment of male hypogonadism. Major species at pH 7.3.	2.05	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	antifungal agent; human metabolite
behenic acid behenic acid: RN given refers to parent cpd; structure. docosanoic acid : A straight-chain, C22, long-chain saturated fatty acid.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
methylergonovine Methylergonovine: A homolog of ERGONOVINE containing one more CH2 group. (Merck Index, 11th ed)	2.07	1	0	ergoline alkaloid
2,2'-methylenebis(4-methyl-6-tert-butylphenol) [no description available]	2.07	1	0	diarylmethane
dibenzoylmethane dibenzoylmethane : A beta-diketone that is acetylacetone (acac) in which both methyl groups have been replaced by phenyl groups. It is a minor constituent of the root extract of licorice (Glycyrrhiza glabra) and exhibits antimutagenic and anticancer effects.	3.31	1	0	aromatic ketone; beta-diketone	antimutagen; antineoplastic agent; metabolite
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	2.05	1	0	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
indolebutyric acid indolebutyric acid: RN given refers to parent cpd. indole-3-butyric acid : A indol-3-yl carboxylic acid that is butanoic acid carrying a 1H-indol-3-yl substituent at position 1.	2.07	1	0	indol-3-yl carboxylic acid	auxin; plant hormone; plant metabolite
shikimic acid Shikimic Acid: A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.. shikimic acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms.	2.51	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.)	2.15	1	0	NTA; tricarboxylic acid	carcinogenic agent; nephrotoxic agent
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2.04	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
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.	2.44	2	0	catechin	antioxidant; plant metabolite
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	2.69	2	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
thiazoles [no description available]	2.17	1	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
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
galantamine Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.	2.08	1	0	benzazepine alkaloid fundamental parent; benzazepine alkaloid; organic heterotetracyclic compound; tertiary amino compound	antidote to curare poisoning; cholinergic drug; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant 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
boldine [no description available]	2.07	1	0	aporphine alkaloid
indirubin [no description available]	2.07	1	0
plumbagin plumbagin: a superoxide anion generator. plumbagin : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.	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.	2.07	1	0	aromatic primary alcohol; dihydroxyanthraquinone	antineoplastic agent; plant metabolite
osthol osthol: from Cnidium monnieri and Angelica pubescens (both Apiaceae); structure given in first source	2.07	1	0	botanical anti-fungal agent; coumarins	metabolite
cytisine [no description available]	2.07	1	0	alkaloid; bridged compound; lactam; organic heterotricyclic compound; secondary amino compound	nicotinic acetylcholine receptor agonist; phytotoxin; plant metabolite
bicuculline Bicuculline: An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.. bicuculline : A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.	2.07	1	0	benzylisoquinoline alkaloid; isoquinoline alkaloid; isoquinolines	agrochemical; central nervous system stimulant; GABA-gated chloride channel antagonist; GABAA receptor antagonist; neurotoxin
kainic acid Kainic Acid: (2S-(2 alpha,3 beta,4 beta))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid. Ascaricide obtained from the red alga Digenea simplex. It is a potent excitatory amino acid agonist at some types of excitatory amino acid receptors and has been used to discriminate among receptor types. Like many excitatory amino acid agonists it can cause neurotoxicity and has been used experimentally for that purpose.	2.07	1	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
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.	2.05	1	0	hydroxy monocarboxylic acid	plant metabolite
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	2.13	1	0
mustard gas Mustard Gas: Severe irritant and vesicant of skin, eyes, and lungs. It may cause blindness and lethal lung edema and was formerly used as a war gas. The substance has been proposed as a cytostatic and for treatment of psoriasis. It has been listed as a known carcinogen in the Fourth Annual Report on Carcinogens (NTP-85-002, 1985) (Merck, 11th ed).. bis(2-chloroethyl) sulfide : An ethyl sulfide that is diethyl sulfide in which a hydrogen from each of the terminal methyl groups is replaced by a chlorine. It is a powerful vesicant regulated under the Chemical Weapons Convention.	3.5	1	1	ethyl sulfide; organochlorine compound	alkylating agent; carcinogenic agent; vesicant
margaric acid margaric acid: RN given refers to unlabeled parent cpd. heptadecanoic acid : A C17 saturated fatty acid and trace component of fats in ruminants.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; mammalian metabolite
arachidic acid icosanoic acid : A C20 striaght-chain saturated fatty acid which forms a minor constituent of peanut (L. arachis) and corn oils. Used as an organic thin film in the production of liquid crystals for a wide variety of technical applications.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
oleanolic acid [no description available]	2.07	1	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.	2.52	2	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.	2.45	2	0	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	2.07	1	0	C-nitro compound; imidazoles	antitubercular agent
herniarin herniarin: methoxy analog of umbelliferone; structure. herniarin : A member of the class of coumarins that is coumarin substituted by a methoxy group at position 7.	2.05	1	0	coumarins	fluorochrome
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.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite
lignoceric acid lignoceric acid: RN given refers to parent cpd; structure. tetracosanoic acid : A C24 straight-chain saturated fatty acid.	2.05	1	0	straight-chain saturated fatty acid; very long-chain fatty acid	Daphnia tenebrosa metabolite; human metabolite; 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.	2.01	1	0	bis(azo) compound
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.51	2	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
Berberine chloride (TN) [no description available]	2.07	1	0	organic molecular entity
tridecanoic acid tridecanoate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of tridecanoic acid.. tridecanoic acid : A C13 straight-chain saturated fatty acid.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
nonadecanoic acid nonadecanoic acid : A C19 straight-chain fatty acid of plant or bacterial origin. An intermediate in the biodegradation of n-icosane, it has been shown to inhibit cancer growth.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	fungal metabolite
deoxycytidine [no description available]	3.87	2	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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.	2.72	3	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
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
2-tert-butylhydroquinone 2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent. 2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.	2.05	1	0	hydroquinones	food antioxidant
muscarine [no description available]	2.07	1	0
heneicosanoic acid henicosanoic acid : A long-chain fatty acid that is henicosane in which one of the methyl groups has been oxidised to give the corresponding carboxylic acid.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid
thioflavin t thioflavin T: RN given refers to chloride; structure. thioflavine T : An organic chloride salt having 2-[4-(dimethylamino)phenyl]-3,6-dimethyl-1,3-benzothiazol-3-ium as the counterion. It is widely used to visualise and quantify the presence of amyloids, both in vitro and in vivo.	2.17	1	0	organic chloride salt	fluorochrome; geroprotector; histological dye
tricosanoic acid tricosanoic acid : A very long-chain fatty acid that is tricosane in which one of the methyl groups has been oxidised to the corresponding carboxylic acid.	2.05	1	0	straight-chain saturated fatty acid; very long-chain fatty acid	Daphnia magna metabolite; human metabolite; plant metabolite
ecdysone [no description available]	2.07	1	0	14alpha-hydroxy steroid; 22-hydroxy steroid; 25-hydroxy steroid; 2beta-hydroxy steroid; 3beta-sterol; 6-oxo steroid; ecdysteroid	prohormone
n-deacetyl-n-formylcolchicine N-deacetyl-N-formylcolchicine: structure given in first source	2.07	1	0	cyclic ketone
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	7.11	1	0	cobalt group element atom; platinum group metal atom
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	2.15	1	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
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.	7.31	1	0	metal allergen; nickel group element atom; platinum group metal atom
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	7.11	1	0	cobalt group element atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	7.07	1	0	iron group element atom; platinum group metal atom
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.43	2	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
ferric nitrilotriacetate ferric nitrilotriacetate: induces diabetes in animals (iron loading)	2.15	1	0	iron chelate	carcinogenic agent; mutagen
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.	3.16	5	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
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.	2.04	1	0	benzenes; phenyl acetates
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.	2.44	2	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.	2.05	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
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	2.02	1	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	2.48	2	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
etoposide [no description available]	2.43	2	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
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
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
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	2.74	3	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
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
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
tolrestat tolrestat: RN & structure given in first source	2.15	1	0	naphthalenes	EC 1.1.1.21 (aldehyde reductase) inhibitor
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
gemcitabine gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.	3.87	2	1	organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; environmental contaminant; immunosuppressive agent; photosensitizing agent; prodrug; radiosensitizing agent; xenobiotic
daunorubicin hydrochloride [no description available]	2.07	1	0	anthracycline
mevastatin mevastatin: antifungal metabolite from Penicillium brevicopactum; potent inhibitory activity to sterol synthesis; structure. mevastatin : A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals.	2.07	1	0	2-pyranones; carboxylic ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	antifungal agent; apoptosis inducer; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; fungal metabolite; Penicillium metabolite
ursolic acid [no description available]	2.47	2	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
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
betulinic acid [no description available]	2.07	1	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
diminazene aceturate [no description available]	2.05	1	0
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.	2.45	2	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant 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
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
bergenin bergenin: RN refers to (2R-(2alpha,3beta,4alpha,4aalpha,10bbeta))-isomer; structure	2.07	1	0	trihydroxybenzoic acid	metabolite
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
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
epicatechin (-)-epicatechin : A catechin with (2R,3R)-configuration.	2.74	3	0	catechin; polyphenol	antioxidant
gallocatechol (-)-epigallocatechin : A flavan-3,3',4',5,5',7-hexol having (2R,3R)-configuration.	2.02	1	0	catechin; flavan-3,3',4',5,5',7-hexol	antioxidant; food component; plant metabolite
hesperetin [no description available]	2.07	1	0	3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone	antineoplastic agent; antioxidant; plant metabolite
magnolol [no description available]	2.07	1	0	biphenyls
honokiol [no description available]	2.47	2	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
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
(-)-catechin (-)-catechin : The (-)-enantiomer of catechin.	2.05	1	0	catechin	metabolite
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
4-hydroxyindole hydroxyindoles : Any member of the class of indoles carrying at least one hydroxy group.	2.07	1	0	hydroxyindoles; phenols
4'-methoxyflavone 4'-methoxyflavone: from seeds of Psoralea corylifolia (Fabaceae); structure in first source	2.05	1	0	ether; flavonoids
eriocitrin eriocitrin: structure in first source. eriocitrin : A disaccharide derivative that consists of eriodictyol substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.07	1	0	3'-hydroxyflavanones; 4'-hydroxyflavanones; disaccharide derivative; flavanone glycoside; rutinoside; trihydroxyflavanone	antioxidant
7,8-dihydromethysticin [no description available]	2.07	1	0	2-pyranones; aromatic ether
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	2.07	1	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
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.	2.07	1	0	cyclic terpene ketone; pentacyclic triterpenoid	anti-inflammatory drug; antipyretic; non-narcotic analgesic; plant metabolite
catalpol [no description available]	2.07	1	0	organic molecular entity	metabolite
quinine hydrochloride [no description available]	2.07	1	0
sarsasapogenin [no description available]	2.07	1	0	sapogenin
corynanthine Corynanthine: A stereoisomer of yohimbine.	2.07	1	0	yohimban alkaloid
prunin protein, prunus prunin protein, Prunus: a legumin-like type of globulin; structure given in first source. naringenin 7-O-beta-D-glucoside : A flavanone 7-O-beta-D-glucoside that is (S)-naringenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.07	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; flavanone 7-O-beta-D-glucoside; monosaccharide derivative	antibacterial agent; antilipemic drug; hypoglycemic agent; metabolite
podocarpic acid podocarpic acid: structure. podocarpic acid : An abietane diterpenoid lacking the isopropyl substituent with an aromatic C-ring and a hydroxy group at the 12-position.	2.07	1	0	abietane diterpenoid
harmol hydrochloride [no description available]	2.07	1	0
5-Methoxyflavone 5-methoxyflavone: DNA polymerase-beta inhibitor and neuroprotective agent against beta-amyloid toxicity; structure in first source	2.07	1	0	ether; flavonoids
10-hydroxycamptothecin [no description available]	2.07	1	0	pyranoindolizinoquinoline
phorbolol myristate acetate [no description available]	2.8	3	0
corydaline [no description available]	2.07	1	0	isoquinoline alkaloid; isoquinolines
demissidine [no description available]	2.07	1	0	alkaloid; organic heteropolycyclic compound; steroid
cinchonidine cinchonidine: has antimalarial activity; diastereoisomer of cinchonine with distinct physiochemical properties; RN given refers to parent cpd(8alpha,9R)-isomer. cinchonidine : 8-epi-Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (R configuration). A diasteroisomer of cinchonine, it occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis.	2.07	1	0	(8xi)-cinchonan-9-ol; cinchona alkaloid	metabolite
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.	2.17	1	0	aromatic ether; secondary amino compound	metabolite
propidium iodide [no description available]	2.07	1	0	organic iodide salt
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
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.	2.44	2	0	catechin; gallate ester; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
deguelin deguelin: a natural product from Mundulea sericea; RN refers to (7aS-cis)-isomer; structure given in first source. deguelin : A rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers.	2.07	1	0	aromatic ether; diether; organic heteropentacyclic compound; rotenones	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; mitochondrial NADH:ubiquinone reductase inhibitor; plant metabolite
catechin (+)-catechin monohydrate : The monohydrate of (+)-catechin.	2.07	1	0	hydrate	geroprotector
daidzin daidzin: a potent, selective, and reversible inhibitor of human mitochondrial aldehyde dehydrogenase. daidzein 7-O-beta-D-glucoside : A glycosyloxyisoflavone that is daidzein attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It is used in the treatment of alcohol dependency (antidipsotropic).	2.07	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; monosaccharide derivative	plant metabolite
cafestol [no description available]	2.07	1	0	diterpenoid; furans; organic heteropentacyclic compound; primary alcohol; tertiary alcohol	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; hypoglycemic agent; plant metabolite
parthenolide [no description available]	2.07	1	0	germacranolide
homoorientin homoorientin: isolated from Swertia japonica; structure given in first source	2.07	1	0	flavone C-glycoside; tetrahydroxyflavone	antineoplastic agent; radical scavenger
cp 65,526 azidoprazosin: labeled with 125I	2.02	1	0
asiatic acid [no description available]	2.07	1	0	monocarboxylic acid; pentacyclic triterpenoid; triol	angiogenesis modulating agent; metabolite
angustmycin a angustmycin A: structure; from Streptomyces hygroscopicus; inhibits GMP synthesis	2.07	1	0	6-aminopurines
razadyne Razadyne: Name of the FDA approved preparation from J&J.	2.07	1	0
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
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
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).	2.01	1	0	nitrogen oxoacid
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
tetrahydrocurcumin tetrahydrocurcumin : A beta-diketone that is curcumin in which both of the double bonds have been reduced to single bonds.	6.29	13	1	beta-diketone; diarylheptanoid; polyphenol	metabolite
yakuchinone-a yakuchinone-A: from Alpinia oxyphylla; structure given in first source. 1-(4'-hydroxy-3'-methoxyphenyl)-7-phenyl-3-heptanone : A ketone that is heptan-3-one substituted by a 4-hydroxy-3-methoxyphenyl group at position 1 and a phenyl group at position 7. Isolated from in Alpinia oxyphylla, it exhibits antineoplastic and inhibitory activities against COX-1, COX-2 and NO synthase.	3.31	1	0	ketone; monomethoxybenzene; phenols	antineoplastic agent; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; EC 1.14.13.39 (nitric oxide synthase) inhibitor; metabolite
sinensetin sinensetin: isolated from citrus fruit; exhibit antiadhesive action on platelets. sinensetin : A pentamethoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 3' and 4' respectively.	2.07	1	0	pentamethoxyflavone	plant metabolite
harmalol hydrochloride [no description available]	2.07	1	0
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
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	2.43	2	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
camphora camphora: a component of Guanxingao, a kind of traditional Chinese rubber electuary medicine which is able to either cure or guard against coronary heart disease and angina pectoris. (R)-camphor : The (R)- enantiomer of camphor.	2.05	1	0	camphor
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.	2.06	1	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
cryptotanshinone cryptotanshinone: from Salvia miltiorrhiza	2.07	1	0	abietane diterpenoid	anticoronaviral agent
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
ar-turmerone ar-turmerone: potent antivenom against snake bites; isolated form Curcuma longa; structure given in first source. (+)-(S)-ar-turmerone : A sesquiterpenoid that is 2-methylhept-2-en-4-one substituted by a 4-methylphenyl group at position 6. It has been isolated from Peltophorum dasyrachis.	2.13	1	0	enone; sesquiterpenoid	EC 3.1.1.7 (acetylcholinesterase) inhibitor; plant metabolite
isovitexin [no description available]	2.07	1	0	C-glycosyl compound; trihydroxyflavone	EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
sclareol sclareol: structure given in first source. sclareol : A labdane diterpenoid that is labd-14-ene substituted by hydroxy groups at positions 8 and 13. It has been isolated from Salvia sclarea.	2.07	1	0	labdane diterpenoid	antifungal agent; antimicrobial agent; apoptosis inducer; fragrance; plant metabolite
tanshinone ii a tashinone IIA: a cardiovascular agent with antineoplastic activity; isolated from Salvia miltiorrhiza; structure in first source	2.07	1	0	abietane diterpenoid
leucodin leucodin: structure in first source	2.07	1	0	sesquiterpene lactone
limonin [no description available]	2.07	1	0	epoxide; furans; hexacyclic triterpenoid; lactone; limonoid; organic heterohexacyclic compound	inhibitor; metabolite; volatile oil component
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.	2.44	2	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
sitosterol, (3beta)-isomer Sobatum: tradename; active fraction of Solanum trilobatum; reduces side-effects of radiation-induced toxicity. sitosterol : A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3.	2.07	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C29-steroid; phytosterols; stigmastane sterol	anticholesteremic drug; antioxidant; mouse metabolite; plant metabolite; sterol methyltransferase inhibitor
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
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]	2.07	1	0	acetate ester; cyclic ketone; delta-lactone; organic heteropentacyclic compound	anticoronaviral agent; antineoplastic agent; autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector; Penicillium metabolite; radiosensitizing agent
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
calcein am calcein AM: a non-fluorescent compound cleaved to a fluorescent compound by non-specific intracellular esterases. calcein am : An organic heteropentacyclic compound that is calcein in which all four carboxy group hydrogens have been substituted by (acetyloxy)methoxy groups and the hyrodgens of the two hydroxy groups have been substituted by acetyl groups. It is a a non-fluorescent probe cleaved to a fluorescent probe by non-specific intracellular esterases.	2.02	1	0	2-benzofurans; acetate ester; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; xanthene dye	fluorochrome
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.	2.25	1	0
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	2.07	1	0	(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.	2.07	1	0	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
puromycin [no description available]	2.07	1	0	puromycins	antiinfective agent; antimicrobial agent; antineoplastic agent; EC 3.4.11.14 (cytosol alanyl aminopeptidase) inhibitor; EC 3.4.14.2 (dipeptidyl-peptidase II) inhibitor; nucleoside antibiotic; protein synthesis inhibitor
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	2.07	1	0	taxifolin	metabolite
cholesteryl glucoside cholesteryl glucoside: RN given refers to cpd without isomeric designation	2.05	1	0	monosaccharide derivative; sterol 3-beta-D-glucoside
mimosine L-mimosine : An L-alpha-amino acid that is propionic acid substituted by an amino group at position 2 and a 3-hydroxy-4-oxopyridin-1(4H)-yl group at position 3 (the 2S-stereoisomer). It a non-protein plant amino acid isolated from Mimosa pudica.	2.07	1	0	4-pyridones; amino acid zwitterion; non-proteinogenic L-alpha-amino acid	EC 1.14.18.1 (tyrosinase) inhibitor; plant metabolite
eriodictyol eriodictyol: structure. eriodictyol : A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' respectively.	2.07	1	0	3'-hydroxyflavanones; tetrahydroxyflavanone
arbutin hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.	2.07	1	0	beta-D-glucoside; monosaccharide derivative	Escherichia coli metabolite; plant metabolite
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.	2.07	1	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
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
deltaline [no description available]	2.07	1	0	acetate ester; cyclic acetal; diterpene alkaloid; organic polycyclic compound; tertiary alcohol; tertiary amino compound
ingenol [no description available]	2.07	1	0	cyclic terpene ketone; tetracyclic diterpenoid
picrotin picrotin: the less toxic component of PICROTOXIN lacking GABA activity. picrotin : An organic heteropentacyclic compound that is picrotoxinin in which the olefinic double bond has undergone addition of water to give the corresponding tertiary alcohol. It is the less toxic component of picrotoxin, lacking GABA activity.	2.07	1	0	diol; epoxide; gamma-lactone; organic heteropentacyclic compound; picrotoxane sesquiterpenoid; tertiary alcohol	plant metabolite
picrotoxinin [no description available]	2.07	1	0	epoxide; gamma-lactone; organic heteropentacyclic compound; picrotoxane sesquiterpenoid; tertiary alcohol	GABA antagonist; plant metabolite; serotonergic antagonist
naringin [no description available]	2.45	2	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
isonaringin isonaringin: structure in first source. narirutin : A disaccharide derivative that is (S)-naringenin substituted by a 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.07	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; rutinoside	anti-inflammatory agent; antioxidant; metabolite
ochratoxin a ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.	2.07	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
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.	3.62	2	0	beta-hydroxy ketone; guaiacols	antineoplastic agent; plant metabolite
securinine securinine: a quinolizine pseudoalkaloid (not from amino acid) from Securinega suffurutiosa or Securinini nitras	2.07	1	0	indolizines
Dubinidine [no description available]	2.07	1	0	organic heterotricyclic compound; organonitrogen heterocyclic compound; oxacycle
cyclopamine [no description available]	2.07	1	0	piperidines	glioma-associated oncogene inhibitor
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	2.06	1	0
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.	2.21	1	0	cyclodextrin
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	3.31	1	0	cinnamic acid	plant metabolite
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	2.53	2	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
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	2.07	1	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).	2.01	1	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	4.12	4	0	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
thapsigargin Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.	2.07	1	0	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
mycophenolic acid Mycophenolic Acid: Compound derived from Penicillium stoloniferum and related species. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase (IMP DEHYDROGENASE). Mycophenolic acid exerts selective effects on the immune system in which it prevents the proliferation of T-CELLS, LYMPHOCYTES, and the formation of antibodies from B-CELLS. It may also inhibit recruitment of LEUKOCYTES to sites of INFLAMMATION.. mycophenolate : A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of mycophenolic acid.. mycophenolic acid : A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mofetil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.	2.07	1	0	2-benzofurans; gamma-lactone; monocarboxylic acid; phenols	anticoronaviral agent; antimicrobial agent; antineoplastic agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; environmental contaminant; immunosuppressive agent; mycotoxin; Penicillium metabolite; xenobiotic
lycopene [no description available]	2.05	1	0	acyclic carotene	antioxidant; plant metabolite
alitretinoin Alitretinoin: A retinoid that is used for the treatment of chronic hand ECZEMA unresponsive to topical CORTICOSTEROIDS. It is also used to treat cutaneous lesions associated with AIDS-related KAPOSI SARCOMA.	2.07	1	0	retinoic acid	antineoplastic agent; keratolytic drug; metabolite; retinoid X receptor agonist
L-cycloserine L-cycloserine : A 4-amino-1,2-oxazolidin-3-one that has S configuration. An antibiotic isolated from Erwinia uredovora.	2.07	1	0	4-amino-1,2-oxazolidin-3-one	anti-HIV agent; anticonvulsant; EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor
12-deoxyphorbol 13-acetate [no description available]	2.07	1	0	phorbol ester	metabolite
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
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
(+)-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
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
hirsutanone hirsutanone: from methanolic extract of the aerial parts of Viscum cruciatum (Viscaceae)	2.05	1	0	diarylheptanoid
calebin-a calebin-A: structure in first source	2.01	1	0	hydroxycinnamic 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.	2.05	1	0	4-coumaric acid	food component; mouse metabolite; plant metabolite
chalcone trans-chalcone : The trans-isomer of chalcone.	4.15	4	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
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.	2.49	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.	2.11	1	0	stilbene
isoliquiritigenin [no description available]	2.41	2	0	chalcones	antineoplastic agent; biological pigment; EC 1.14.18.1 (tyrosinase) inhibitor; GABA modulator; geroprotector; metabolite; NMDA receptor antagonist
dibenzylidene acetone dibenzylidene acetone: structure in first source	2.81	3	0
cardamonin cardamonin: found in Zingiberaceae; structure in first source	1.99	1	0	chalcones
Methylenedioxycinnamic acid [no description available]	2.05	1	0	hydroxycinnamic acid
rauwolscine Rauwolscine: A stereoisomer of yohimbine.	2.07	1	0	methyl 17-hydroxy-20xi-yohimban-16-carboxylate
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
sesquiterpenes [no description available]	2.78	3	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
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	3.88	3	0	caffeic acid	geroprotector; mouse metabolite
methyl caffeate methyl caffeate: from plant Gaillardia pulchella. methyl caffeate : An alkyl caffeate ester formed by the formal condensation of caffeic acid with methyl alcohol.	2.01	1	0	alkyl caffeate ester; methyl ester
ethyl ferulate ethyl ferulate: structure in first source	2.06	1	0
4-hydroxycinnamoylmethane 4-hydroxycinnamoylmethane: RN given refers to cpd without isomeric designation. p-hydroxyphenylbut-3-ene-2-one : An enone in which a 4-hydroxyphenyl group is attached to the beta-carbon atom of but-3-en-2-one.	2.1	1	0
(1e,4e)-1,5-bis(2-methoxyphenyl)penta-1,4-dien-3-one [no description available]	2.17	1	0
isoeugenol trans-isoeugenol : The trans-stereoisomer of isoeugenol.	3.31	1	0	isoeugenol	plant metabolite
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
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.	14.67	171	10	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
sulindac Sulindac: A sulfinylindene derivative prodrug whose sulfinyl moiety is converted in vivo to an active NSAID analgesic. Specifically, the prodrug is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This helps to maintain constant blood levels with reduced gastrointestinal side effects.. sulindac : A monocarboxylic acid that is 1-benzylidene-1H-indene which is substituted at positions 2, 3, and 5 by methyl, carboxymethyl, and fluorine respectively, and in which the phenyl group of the benzylidene moiety is substituted at the para position by a methylsulfinyl group. It is a prodrug for the corresponding sulfide, a non-steroidal anti-inflammatory drug, used particularly in the treatment of acute and chronic inflammatory conditions.	2.06	1	0	monocarboxylic acid; organofluorine compound; sulfoxide	analgesic; antineoplastic agent; antipyretic; apoptosis inducer; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug; tocolytic agent
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	3.62	2	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
cyqualon cyclovalone: is a synthetic curcumin derivative; structure in first source	2.96	4	0
aurapten aurapten: RN refers to (E)-isomer; structure given in first source. auraptene : A member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group. Ii is isolated from several edible fruits and vegetables and exhibits a variety of therapeutic properties.	2.07	1	0	coumarins; monoterpenoid	antihypertensive agent; antineoplastic agent; antioxidant; apoptosis inducer; dopaminergic agent; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; gamma-secretase modulator; gastrointestinal drug; hepatoprotective agent; matrix metalloproteinase inhibitor; neuroprotective agent; plant metabolite; PPARalpha agonist; vulnerary
caryophyllene oxide caryophyllene oxide: has butyrylcholinesterase inhibitory activity; structure in first source. epoxide : Any cyclic ether in which the oxygen atom forms part of a 3-membered ring.	2.11	1	0	epoxide	metabolite
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	2.47	2	0	cinnamate ester; tannin	food component; plant metabolite
2,6-bis(2,5-dimethoxybenzylidene)cyclohexanone 2,6-bis(2,5-dimethoxybenzylidene)cyclohexanone: an anti-inflammatory agent that down-regulates cyclooxygenase-2 expression; structure in first source	2.17	1	0
D-fructopyranose [no description available]	2.11	1	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
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]	2.17	1	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
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.45	2	0
artemotil artemotil: structure given in first source; RN given refers to cpd without isomeric designation	2.07	1	0	artemisinin derivative
lincomycin Lincomycin: An antibiotic produced by Streptomyces lincolnensis var. lincolnensis. It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.. lincomycin : A carbohydrate-containing antibiotic produced by the actinomyces Streptomyces lincolnensis.	2.07	1	0	carbohydrate-containing antibiotic; L-proline derivative; monocarboxylic acid amide; pyrrolidinecarboxamide; S-glycosyl compound	antimicrobial agent; bacterial metabolite
valinomycin Valinomycin: A cyclododecadepsipeptide ionophore antibiotic produced by Streptomyces fulvissimus and related to the enniatins. It is composed of 3 moles each of L-valine, D-alpha-hydroxyisovaleric acid, D-valine, and L-lactic acid linked alternately to form a 36-membered ring. (From Merck Index, 11th ed) Valinomycin is a potassium selective ionophore and is commonly used as a tool in biochemical studies.. valinomycin : A twelve-membered cyclodepsipeptide composed of three repeating D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl units joined in sequence. An antibiotic found in several Streptomyces strains.	2.07	1	0	cyclodepsipeptide; macrocycle	antimicrobial agent; antiviral agent; bacterial metabolite; potassium ionophore
u 0126 U 0126: protein kinase kinase inhibitor; structure in first source	2.05	1	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
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
12-deoxyphorbolphenylacetate-20-acetate [no description available]	2.07	1	0
brassinin [no description available]	2.07	1	0	dithiocarbamic ester; indole phytoalexin
chaetomellic acid a chaetomellic acid A: structure given in first source; an inhibitor of farnesyl-protein transferase	2.07	1	0
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
zd 6474 CH 331: structure in first source	2.31	1	0	aromatic ether; organobromine compound; organofluorine compound; piperidines; quinazolines; secondary amine	antineoplastic agent; tyrosine kinase inhibitor
calixarenes Calixarenes: Phenolic metacyclophanes derived from condensation of PHENOLS and ALDEHYDES. The name derives from the vase-like molecular structures. A bracketed [n] indicates the number of aromatic rings.. calixarenes : Originally macrocyclic compounds capable of assuming a basket (or "calix") shaped conformation. They are formed from p-hydrocarbyl phenols and formaldehyde. The term now applies to a variety of derivatives by substitution of the hydrocarbon cyclo{oligo[(1,3-phenylene)methylene]}.. calixarene : A macrocycle composed of 1,3-phenylene groups linked by methylene groups. The number of 1,3-phenylene units in the macrocycle is denoted by the "n" in calix[n]arene name.	2.31	1	0
salinomycin salinomycin: from Streptomyces albus; RN given refers to parent cpd; structure	2.07	1	0	polyketide; spiroketal	animal growth promotant; potassium ionophore
silybin [no description available]	2.07	1	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.17	1	0
rhodamine 123 Rhodamine 123: A fluorescent probe with low toxicity which is a potent substrate for ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 and the bacterial multidrug efflux transporter. It is used to assess mitochondrial bioenergetics in living cells and to measure the efflux activity of ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 in both normal and malignant cells. (Leukemia 1997;11(7):1124-30). rhodamine 123(1+) : A cationic fluorescent dye derived from 9-phenylxanthene.	2.02	1	0	organic cation; xanthene dye	fluorochrome
5,6-dehydrokawain 5,6-dehydrokawain: from Alpinia speciosa rhizoma; RN given for cpd without isomeric designation; structure given in first source	2.43	2	0	2-pyranones; aromatic ether
9,10-dihydrolysergol 9,10-dihydrolysergol: RN given refers to cpd without isomeric designation	2.07	1	0
geranylgeranic acid geranylgeranic acid: RN given refers to cpd without isomeric designation. (2E,6E,10E)-geranylgeranic acid : A diterpenoid obtained by formal oxidation of the CH2OH group of (E,E,E)-geranylgeraniol to the corresponding carboxylic acid.	2.07	1	0	alpha,beta-unsaturated monocarboxylic acid; diterpenoid; methyl-branched fatty acid; trienoic fatty acid
quercetin [no description available]	2.97	4	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
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.	2.47	2	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	2.07	1	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
biochanin a [no description available]	2.47	2	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]	2.47	2	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]	2.07	1	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.	2.47	2	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.	2.47	2	0	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	2.47	2	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
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	2.45	2	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
quercitrin [no description available]	2.47	2	0	alpha-L-rhamnoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	antileishmanial agent; antioxidant; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; plant metabolite
scopoletin [no description available]	2.98	4	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.	2.44	2	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
hymecromone Hymecromone: A coumarin derivative possessing properties as a spasmolytic, choleretic and light-protective agent. It is also used in ANALYTICAL CHEMISTRY TECHNIQUES for the determination of NITRIC ACID.	2.07	1	0	hydroxycoumarin	antineoplastic agent; hyaluronic acid synthesis inhibitor
alprostadil [no description available]	2.07	1	0	prostaglandins E	anticoagulant; human metabolite; platelet aggregation inhibitor; vasodilator agent
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.	3.85	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	2.07	1	0	beta-D-glucoside; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; antipruritic drug; bone density conservation agent; geroprotector; histamine antagonist; osteogenesis regulator; plant metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.07	1	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	2.07	1	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
genistein [no description available]	2.47	2	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
erucic acid [no description available]	2.05	1	0	docosenoic acid
nervonic acid (15Z)-tetracosenoic acid : A tetracosenoic acid having a cis-double bond at position 15.	2.05	1	0	tetracosenoic acid
butein [no description available]	2.71	3	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	2.47	2	0	7-hydroxyisoflavones 7-O-beta-D-glucoside
chartreusin chartreusin: structure	2.07	1	0	benzochromenone; glycoside
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
baicalein [no description available]	2.07	1	0	trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 4.1.1.17 (ornithine decarboxylase) inhibitor; ferroptosis inhibitor; geroprotector; hormone antagonist; plant metabolite; prostaglandin antagonist; radical scavenger
chrysin chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.	2.47	2	0	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
datiscetin datiscetin : A tetrahydroxyflavone that is 7-hydroxyflavonol bearing two additional hydroxy substituents at positions 2' and 5.	2.07	1	0	7-hydroxyflavonol; tetrahydroxyflavone
diosmetin [no description available]	2.07	1	0	3'-hydroxyflavonoid; monomethoxyflavone; trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; bone density conservation agent; cardioprotective agent; plant metabolite; tropomyosin-related kinase B receptor agonist; vasodilator agent
diosmin [no description available]	2.07	1	0	dihydroxyflavanone; disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; rutinoside	anti-inflammatory agent; antioxidant
fisetin [no description available]	2.07	1	0	3'-hydroxyflavonoid; 7-hydroxyflavonol; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; metabolite; plant metabolite
galangin 5,7-dihydroxyflavonol: antimicrobial from the twigs of Populus nigra x Populus deltoides; structure in first source. galangin : A 7-hydroxyflavonol with additional hydroxy groups at positions 3 and 5 respectively; a growth inhibitor of breast tumor cells.	2.07	1	0	7-hydroxyflavonol; trihydroxyflavone	antimicrobial agent; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; plant metabolite
3-methylquercetin isorhamnetin : A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.	2.07	1	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	anticoagulant; EC 1.14.18.1 (tyrosinase) inhibitor; metabolite
morin morin: a light yellowish pigment found in the wood of old fustic (Chlorophora tinctoria). morin : A pentahydroxyflavone that is 7-hydroxyflavonol bearing three additional hydroxy substituents at positions 2' 4' and 5.	2.07	1	0	7-hydroxyflavonol; pentahydroxyflavone	angiogenesis modulating agent; anti-inflammatory agent; antibacterial agent; antihypertensive agent; antineoplastic agent; antioxidant; EC 5.99.1.2 (DNA topoisomerase) inhibitor; hepatoprotective agent; metabolite; neuroprotective agent
myricetin [no description available]	2.07	1	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
rhamnetin rhamnetin: aglycone of xanthorhamnin; from Rhamnus. rhamnetin : A monomethoxyflavone that is quercetin methylated at position 7.	2.07	1	0	monomethoxyflavone; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; metabolite
robinetin robinetin: structure given in first source. robinetin : A pentahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 7, 3, 4' and 5'.	2.07	1	0	7-hydroxyflavonol; pentahydroxyflavone	plant metabolite
tamarixetin tamarixetin: isolated from Costsus spicatus. tamarixetin : A monomethoxyflavone that is quercetin methylated at position O-4'. Isolated from Cyperus teneriffae.	2.07	1	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	antioxidant; metabolite
wogonin wogonin: structure in first source. wogonin : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-8.	2.07	1	0	dihydroxyflavone; monomethoxyflavone	angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite
coumestrol Coumestrol: A daidzein derivative occurring naturally in forage crops which has some estrogenic activity.. coumestrol : A member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9.	2.07	1	0	coumestans; delta-lactone; polyphenol	anti-inflammatory agent; antioxidant; plant metabolite
daidzein [no description available]	2.47	2	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
gingerenone a gingerenone A: has antineoplastic activity; isolated from Zingiber officinale; structure in first source	2.46	2	0	diarylheptanoid
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	2.44	2	0	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
rosmarinic acid rosmarinic acid: RN given refers to parent cpd; promote OT project. (R)-rosmarinic acid : A stereoisomer of rosmarinic acid having (R)-configuration.. rosmarinic acid : The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.	2.42	2	0	rosmarinic acid	geroprotector; plant metabolite
wedelolactone wedelolactone: antihepatotoxic coumestan from Eclipta prostrata and Wedelia calendulacea (both Asteraceae); structure given in first source. wedelolactone : A member of the class of coumestans that is coumestan with hydroxy substituents as positions 1, 8 and 9 and a methoxy substituent at position 3.	2.07	1	0	aromatic ether; coumestans; delta-lactone; polyphenol	antineoplastic agent; apoptosis inducer; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; hepatoprotective agent; metabolite
rottlerin rottlerin: an angiogenesis inhibitor; an inhibitor of protein kinase Cdelta (PKCdelta) and calmodulin kinase III; RN refers to (E)-isomer; do not confuse this chalcone with an anthraquinone that is also called rottlerin (RN 481-72-1);. rottlerin : A chromenol that is 2,2-dimethyl-2H-chromene substituted by hydroxy groups at positions 5 and 7, a 3-acetyl-2,4,6-trihydroxy-5-methylbenzyl group at position 6 and a (1E)-3-oxo-1-phenylprop-1-en-3-yl group at position 8. A potassium channel opener, it is isolated from Mallotus philippensis.	2.07	1	0	aromatic ketone; benzenetriol; chromenol; enone; methyl ketone	anti-allergic agent; antihypertensive agent; antineoplastic agent; apoptosis inducer; K-ATP channel agonist; metabolite
ellagic acid [no description available]	2.07	1	0	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
7-hydroxyflavone 7-hydroxyflavone : A hydroxyflavonoid in which the flavone nucleus is substituted at position 7 by a hydroxy group.	2.07	1	0	hydroxyflavonoid
prostaglandin a1 [no description available]	2.07	1	0	prostaglandins A
coenzyme q10 coenzyme Q10: Ubiquinone ring with a chain of 10 isoprene units; redox equilibrium with ubiqunol serving in mitochondrial inner membrane to transfer electrons; presence during reconstitution of acetylcholine receptor into phospholipid vesicles yields vesicles active in catalyzing carbamylcholine-sensitive Na+ flux; coenzyme Q10 depletion has been noted with use of statins. coenzyme Q10 : A ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration.	2.01	1	0	ubiquinones	antioxidant; ferroptosis inhibitor; human metabolite
cerulenin Cerulenin: An epoxydodecadienamide isolated from several species, including ACREMONIUM, Acrocylindrum, and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.. cerulenin : An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.	2.07	1	0	epoxide; monocarboxylic acid amide	antifungal agent; antiinfective agent; antilipemic drug; antimetabolite; antimicrobial agent; fatty acid synthesis inhibitor
rhoifolin rhoifolin: from many plants. apigenin 7-O-neohesperidoside : An apigenin derivative having an alpha-(1->2)-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety attached to the 7-hydroxy group.	2.07	1	0	dihydroxyflavone; glycosyloxyflavone; neohesperidoside	metabolite
vitexin rhamnoside 2''-O-rhamnopyranosylvitexin: has both analgesic and anti-inflammatory activities; isolated from Alternanthera maritima; structure in first source. vitexin 2''-O-alpha-L-rhamnoside : A derivative of vitexin having an alpha-L-rhamnosyl residue attached at the 2''-position of the glucitol moiety.	2.07	1	0	C-glycosyl compound; disaccharide derivative; trihydroxyflavone	plant metabolite
domoic acid domoic acid: kainic acid analog, heterocyclic amino acid from seaweed; RN given refers to parent cpd; structure. domoic acid : An L-proline derivative that is L-proline substituted by a carboxymethyl group at position 3 and a 6-carboxyhepta-2,4-dien-2-yl group at position 4. It is produced by the diatomic algal Pseudo-nitzschia. It is an analogue of kainic acid and a neurotoxin which causes amnesic shellfish poisoning (ASP).	2.07	1	0	L-proline derivative; non-proteinogenic L-alpha-amino acid; pyrrolidinecarboxylic acid; tricarboxylic acid	algal metabolite; hapten; marine metabolite; neuromuscular agent; neurotoxin
isotretinoin Isotretinoin: A topical dermatologic agent that is used in the treatment of ACNE VULGARIS and several other skin diseases. The drug has teratogenic and other adverse effects.. isotretinoin : A retinoic acid that is all-trans-retinoic acid in which the double bond which is alpha,beta- to the carboxy group is isomerised to Z configuration. A synthetic retinoid, it is used for the treatment of severe cases of acne and other skin diseases.	2.07	1	0	retinoic acid	antineoplastic agent; keratolytic drug; teratogenic agent
cyclosporine ramihyphin A: one of the metabolites produced by Fusarium sp. S-435; RN given refers to cpd with unknown MF	2.07	1	0	homodetic cyclic peptide	anti-asthmatic drug; anticoronaviral agent; antifungal agent; antirheumatic drug; carcinogenic agent; dermatologic drug; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; geroprotector; immunosuppressive agent; metabolite
phenylethyl 3-methylcaffeate phenylethyl 3-methylcaffeate: a caffeic acid ester present in propolis, a natural resin produced by honey bees; structure given in first source	2.01	1	0
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
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.	2.54	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
gamma-cyclodextrin gamma-cyclodextrin : A cycloamylose composed of eight alpha-(1->4) linked D-glucopyranose units.	3.56	1	1	cyclodextrin
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.	7.1	1	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
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
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
ethyl caffeate (E)-ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate: structure in first source. ethyl trans-caffeate : An ethyl ester resulting from the formal condensation of the carboxy group of trans-caffeic acid with ethanol.	2.01	1	0	alkyl caffeate ester; ethyl ester; hydroxycinnamic acid	anti-inflammatory agent; antineoplastic agent; metabolite
hexahydrocurcumin hexahydrocurcumin: from Zingiber officinale; structure in first source	2.98	4	0	diarylheptanoid
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
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
methyl linolenate [no description available]	2.05	1	0	fatty acid methyl ester	insect attractant; plant metabolite
caryophyllene caryophyllene: RN given refers to cpd without isomeric designation; structure given in first source	2.11	1	0
5-hydroxy-3,3',4',7-tetramethoxyflavone 5-hydroxy-3,7,3',4'-tetramethoxyflavone: from the rhizome of Kaempferia parviflora; inhibits monocyte adhesion and cellular reactive oxygen species production in human umbilical vein endothelial cells. 5-hydroxy-3,3',4',7-tetramethoxyflavone : A monohydroxyflavone that is 5-hydroxyflavone which is substituted by methoxy groups at positions 3,3',4' and 7.	2.05	1	0	3'-methoxyflavones; monohydroxyflavone; tetramethoxyflavone	plant metabolite
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	2.76	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
methyl-3-methoxy-4-hydroxystyryl ketone methyl-3-methoxy-4-hydroxystyryl ketone: structure given in first source; RN given refers to cpd without isomeric designation	2.53	2	0	hydroxycinnamic acid
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
4-(2-hydroxyphenyl)but-3-en-2-one 4-(2-hydroxyphenyl)but-3-en-2-one: inhibits lipopolysaccharide-induced expression of inducible nitric oxide synthase; structure in first source	2.17	1	0
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	2.15	1	0	boron group element atom; elemental aluminium; metal atom
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
vinblastine sulfate [no description available]	2.07	1	0
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	2.07	1	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
bleomycin [no description available]	2.07	1	0	bleomycin	antineoplastic agent; metabolite
4,4'-dihydroxychalcone 4,4'-dihydroxychalcone: structure	2.1	1	0
bakuchiol bakuchiol: chief component of Psoralea corylifolia Linn; structure	2.07	1	0
demethoxycurcumin demethoxycurcumin: corresponds to curcumin with one methoxy group replaced by hydrogen; isolated from rhizomes of Curcuma longa. demethoxycurcumin : A beta-diketone that is curcumin in which one of the methoxy groups is replaced by hydrogen. It is found in Curcuma zedoaria and Etlingera elatior.	13.57	100	9	beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antineoplastic agent; metabolite
tetrahydroxycurcumin [no description available]	3.14	5	0	beta-diketone; catechols; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; neuroprotective agent; plant metabolite
zerumbone zerumbone: RN given for (E,E,E)-isomer; structure in first source. zerumbone : A sesquiterpenoid and cyclic ketone that is (1E,4E,8E)-alpha-humulene which is substituted by an oxo group at the carbon atom attached to two double bonds. It is obtained by steam distillation from a type of edible ginger, Zingiber zerumbet Smith, grown particularly in southeast Asia.	3.62	2	0	cyclic ketone; sesquiterpenoid	anti-inflammatory agent; glioma-associated oncogene inhibitor; plant metabolite
2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone 2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone: has antineoplastic activity; structure in first source	2.1	1	0
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
(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
benzyl caffeate benzyl caffeate: isolated from Liaoxi propolis	2.01	1	0
helichrysetin helichrysetin: isolated from Helichrysum odoratissimum; RN from CA Index Guide 1986; RN given refers to (E)-isomer; RN for cpd without isomeric designation not avail. 10/89	1.99	1	0	chalcones
monorden monorden: inhibits HSP90 Heat-Shock Proteins, DNA topoisomerase VI and human Topoisomerase II	2.07	1	0	cyclic ketone; enone; epoxide; macrolide antibiotic; monochlorobenzenes; phenols	antifungal agent; metabolite; tyrosine kinase inhibitor
ginkgolide b [no description available]	2.07	1	0
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
marein marein: hypoglycemic from Coreopsis tinctoria; structure in first source	2.07	1	0	flavonoids; glycoside
curdione curdione: from Curcuma wenyujin; structure in first source	2.04	1	0	germacrane sesquiterpenoid
diacetylcurcumin diacetylcurcumin: structure in first source	8.17	5	0
hylin [no description available]	3.29	6	0
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
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
anisodamine [no description available]	2.07	1	0
isoborneol isoborneol: RN given refers to cpd without isomeric designation; structure	2.11	1	0	borneol
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
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
3,5-bis(2-fluorobenzylidene)piperidin-4-one 3,5-bis(2-fluorobenzylidene)piperidin-4-one: an antineoplastic agent; structure in first source	3.31	1	0
bn 52020 [no description available]	2.07	1	0
dimethoxycurcumin dimethoxycurcumin: has antineoplsatic activity; structure in first source	8.49	7	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
bavachinin bavachinin: do not confuse with bavachin	2.07	1	0	flavanones
1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one 1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one: a macrophage TNF-alpha antagonist; structure in first source	2.96	4	0	diarylheptanoid; enone; phenols	plant metabolite
1,7-bis(4-hydroxy-3-methoxyphenyl)-1,4,6-heptatrien-3-one 1,7-bis(4-hydroxy-3-methoxyphenyl)-1,4,6-heptatrien-3-one: from Curcuma longa; structure in first source	2.96	4	0	diarylheptanoid
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
Dihydrotanshinone I dihydrotanshinone I: extracted from Radix Salviae	2.07	1	0	abietane diterpenoid	anticoronaviral agent
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.	2.52	2	0	benzoxazole
cinobufagin cinobufagin: isolated from Chinese medicinal preparation ch'an su; derived from toad venom	2.07	1	0	steroid lactone
pituitrin Pituitrin: A substance or extract from the neurohypophysis (PITUITARY GLAND, POSTERIOR).	2.31	1	0
atropine sulfate [no description available]	2.07	1	0
cannogenin thevetoside cannogenin thevetoside: from Thevetia neriifolia; minor descriptor (75-84); on-line & Index Medicus search CARDENOLIDES (77-84), CARDANOLIDES (75-76); RN given refers to (3beta,5beta)-isomer	2.07	1	0	cardenolide glycoside
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
curcumol [no description available]	2.04	1	0	sesquiterpenoid
bisacurone bisacurone: an NSAID isolated from Curcuma longa; structure in first source	2.13	1	0
hypocrellin a hypocrellin A: isolated from fungus Hypocrella bambusae sacc	2.07	1	0
oregonin oregonin: a diarylheptanoid from the bark of Alnus hirsuta var. sibirica; inhibits cyclooxygenase-2 expression; structure in first source	3.31	1	0	diarylheptanoid
quercetin [no description available]	2.05	1	0
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	2.01	1	0
dihydrorobinetin dihydrorobinetin: structure in first source	2.07	1	0
chitosan [no description available]	2.11	1	0
icotinib [no description available]	7.25	1	0
monensin [no description available]	2.07	1	0
(E)-1,7-Bis(4-hydroxyphenyl)hept-4-en-3-one [no description available]	2.05	1	0	diarylheptanoid
catechin [no description available]	2.05	1	0
piperidines Piperidines: A family of hexahydropyridines.	2.58	2	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.	2.46	2	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
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
citrinin Citrinin: Antibiotic and mycotoxin from Aspergillus niveus and Penicillium citrinum.	2.07	1	0
vulpinic acid vulpinic acid: RN given refers to cpd without isomeric designation; structure given in first source; vulpinic acid refers to (E)-isomer	2.07	1	0	butenolide
ajmaline [no description available]	2.07	1	0
curcumin glucuronide curcumin glucuronide: a curcumin metabolite	2.1	1	0	diarylheptanoid
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	2	1	0
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	2.17	1	0
amyloid beta-peptides amyloid beta-protein (1-40): although acutely neurotoxic in both rat & monkey cerebral cortex, neuronal degeneration in primates resembles more closely to that found in Alzheimer's disease; amino acid sequence has been determined	2.05	1	0
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	2.25	1	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	2.47	2	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
cnb 001 [no description available]	2.47	2	0
hydrazinocurcumin hydrazinocurcumin: structure in first source. hydrazinocurcumin : A pyrazole obtained by cyclocodensation of the two carbonyl groups of curcumin with hydrazine.	4.42	6	0	aromatic ether; olefinic compound; polyphenol; pyrazoles	angiogenesis modulating agent; antineoplastic agent; EC 2.3.1.48 (histone acetyltransferase) inhibitor; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor
alpha-cyclopiazonic acid [no description available]	2.07	1	0	alpha-cyclopiazonic acids

Condition	Relationship Strength	Studies	Trials
Acute Confusional Senile Dementia [description not available]	6.92	15	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)	11.92	15	1
Leucocythaemia [description not available]	2.5	2	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)	2.5	2	0
Koch's Disease [description not available]	2.05	1	0
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	2.05	1	0
Bone Cancer [description not available]	2.83	3	0
Breast Cancer [description not available]	3.32	6	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.62	8	0
Osteolysis Dissolution of bone that particularly involves the removal or loss of calcium.	2.08	1	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	2.83	3	0
Breast Neoplasms Tumors or cancer of the human BREAST.	3.32	6	0
Osteogenic Sarcoma [description not available]	2.58	2	0
Invasiveness, Neoplasm [description not available]	3.65	8	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)	7.58	2	0
Plasmodium falciparum Malaria [description not available]	2.1	1	0
Malaria, Falciparum Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.	2.1	1	0
Acute Myelogenous Leukemia [description not available]	2.1	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.	2.1	1	0
Benign Neoplasms [description not available]	5.03	8	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.	5.03	8	0
Cancer of Liver [description not available]	3.08	4	0
Liver Neoplasms Tumors or cancer of the LIVER.	3.08	4	0
Cancer of Lung [description not available]	3.94	11	0
Metastase [description not available]	2.57	2	0
Lung Neoplasms Tumors or cancer of the LUNG.	3.94	11	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.57	2	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.	2.17	1	0
Dermatoses [description not available]	2.31	1	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	2.31	1	0
Innate Inflammatory Response [description not available]	5.5	7	2
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.	5.5	7	2
Intestinal Diseases Pathological processes in any segment of the INTESTINE from DUODENUM to RECTUM.	2.31	1	0
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	2.31	1	0
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	2.31	1	0
Infections, Staphylococcal [description not available]	2.31	1	0
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	2.31	1	0
Age-Related Osteoporosis [description not available]	2.41	1	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.	7.41	1	0
Carcinoma, Non-Small Cell Lung [description not available]	3.26	5	0
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	3.26	5	0
Benign Neoplasms, Brain [description not available]	2.41	1	0
Astrocytoma, Grade IV [description not available]	2.41	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.	2.41	1	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.	7.41	1	0
Nerve Pain [description not available]	2.41	1	0
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.41	1	0
Chronic Kidney Diseases [description not available]	2.69	2	0
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	2.69	2	0
Colitis Gravis [description not available]	3.33	1	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.	3.33	1	0
Acute Kidney Failure [description not available]	2.25	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.25	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.	2.25	1	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.25	1	0
Hepatocellular Carcinoma [description not available]	7.57	2	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.	2.57	2	0
Lassitude [description not available]	2.25	1	0
Fatigue The state of weariness following a period of exertion, mental or physical, characterized by a decreased capacity for work and reduced efficiency to respond to stimuli.	2.25	1	0
Idiopathic Parkinson Disease [description not available]	2.25	1	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)	2.25	1	0
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	2.31	1	0
Alloxan Diabetes [description not available]	2.31	1	0
Cardiac Failure [description not available]	2.17	1	0
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	2.17	1	0
Hypertrophy General increase in bulk of a part or organ due to CELL ENLARGEMENT and accumulation of FLUIDS AND SECRETIONS, not due to tumor formation, nor to an increase in the number of cells (HYPERPLASIA).	2.17	1	0
Cancer of Cervix [description not available]	2.17	1	0
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	2.17	1	0
Allergic Rhinitis [description not available]	2.17	1	0
Anaphylactic Reaction [description not available]	2.17	1	0
Allergic Reaction [description not available]	2.17	1	0
Anaphylaxis An acute hypersensitivity reaction due to exposure to a previously encountered ANTIGEN. The reaction may include rapidly progressing URTICARIA, respiratory distress, vascular collapse, systemic SHOCK, and death.	2.17	1	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	2.17	1	0
Rhinitis, Allergic An inflammation of the NASAL MUCOSA triggered by ALLERGENS.	2.17	1	0
Cirrhosis [description not available]	2.21	1	0
Ureteral Obstruction Blockage in any part of the URETER causing obstruction of urine flow from the kidney to the URINARY BLADDER. The obstruction may be congenital, acquired, unilateral, bilateral, complete, partial, acute, or chronic. Depending on the degree and duration of the obstruction, clinical features vary greatly such as HYDRONEPHROSIS and obstructive nephropathy.	2.21	1	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	7.21	1	0
Apoplexy [description not available]	2.51	2	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)	7.51	2	0
Experimental Neoplasms [description not available]	2.1	1	0
Cerebral Ischemia [description not available]	2.13	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.	2.13	1	0
Chronic Illness [description not available]	3.5	1	1
Disease, Pulmonary [description not available]	3.5	1	1
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	3.5	1	1
Lung Diseases Pathological processes involving any part of the LUNG.	3.5	1	1
Extravascular Hemolysis [description not available]	2.76	3	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.76	3	0
Arthritis, Degenerative [description not available]	2.11	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.	7.11	1	0
Carcinoma, Large Cell A tumor of undifferentiated (anaplastic) cells of large size. It is usually bronchogenic. (From Dorland, 27th ed)	2.11	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).	7.13	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.13	1	0
Fatty Liver, Nonalcoholic [description not available]	2.13	1	0
Choline Deficiency A condition produced by a deficiency of CHOLINE in animals. Choline is known as a lipotropic agent because it has been shown to promote the transport of excess fat from the liver under certain conditions in laboratory animals. Combined deficiency of choline (included in the B vitamin complex) and all other methyl group donors causes liver cirrhosis in some animals. Unlike compounds normally considered as vitamins, choline does not serve as a cofactor in enzymatic reactions. (From Saunders Dictionary & Encyclopedia of Laboratory Medicine and Technology, 1984)	2.13	1	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	2.13	1	0
Cancer of Ovary [description not available]	2.13	1	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.	2.13	1	0
Colorectal Cancer [description not available]	2.13	1	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	2.13	1	0
Adenocarcinoma, Basal Cell [description not available]	4.16	3	1
Cancer of Pancreas [description not available]	3.87	2	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	9.16	3	1
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	3.87	2	1
Cancer of Colon [description not available]	2.43	2	0
Colonic Neoplasms Tumors or cancer of the COLON.	2.43	2	0
Gastric Ulcer [description not available]	7.05	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).	2.05	1	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.45	2	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	3.43	1	1
Disease Exacerbation [description not available]	3.85	2	1
ALS - Amyotrophic Lateral Sclerosis [description not available]	2.07	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)	2.07	1	0
Arteriosclerosis, Coronary [description not available]	7.5	4	4
Cardiovascular Stroke [description not available]	7.5	4	4
Coronary Artery Disease Pathological processes of CORONARY ARTERIES that may derive from a congenital abnormality, atherosclerotic, or non-atherosclerotic cause.	7.5	4	4
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	7.5	4	4
Infections, Plasmodium [description not available]	2.07	1	0
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	2.07	1	0
Diabetes Mellitus, Adult-Onset [description not available]	2.07	1	0
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	2.07	1	0
Carcinoma, Ductal, Breast An invasive (infiltrating) CARCINOMA of the mammary ductal system (MAMMARY GLANDS) in the human BREAST.	2.07	1	0
Aortic Diseases Pathological processes involving any part of the AORTA.	2.01	1	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.	2.01	1	0
Alveolitis, Fibrosing [description not available]	2.02	1	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.	2.02	1	0
Anasarca [description not available]	2.04	1	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.04	1	0
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	2.05	1	0
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.	1.98	1	0
Cancer of Skin [description not available]	1.98	1	0
Skin Neoplasms Tumors or cancer of the SKIN.	1.98	1	0
Bile Duct Obstruction [description not available]	2	1	0
Cholestasis Impairment of bile flow due to obstruction in small bile ducts (INTRAHEPATIC CHOLESTASIS) or obstruction in large bile ducts (EXTRAHEPATIC CHOLESTASIS).	2	1	0
B16 Melanoma [description not available]	2.01	1	0
Angiogenesis, Pathologic [description not available]	2.01	1	0

bisdemethoxycurcumin

Description

Cross-References

Synonyms (73)

Research Excerpts

Overview

Effects

Actions

Toxicity

Compound-Compound Interactions

Bioavailability

Dosage Studied

Occurs in Manufacturing (1 Product(s))

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Products

Roles (2)

Drug Classes (4)

Protein Targets (10)

Inhibition Measurements

Biological Processes (101)

Molecular Functions (31)

Ceullar Components (22)

Bioassays (171)

Research

Studies (227)

Market Indicators

Research Demand Index: 26.68

Study Types

bisdemethoxycurcumin

Description

Cross-References

Synonyms (73)

Research Excerpts

Overview

Effects

Actions

Toxicity

Compound-Compound Interactions

Bioavailability

Dosage Studied

Occurs in Manufacturing (1 Product(s))

Product Categories

Products

Roles (2)

Drug Classes (4)

Protein Targets (10)

Inhibition Measurements

Biological Processes (101)

Molecular Functions (31)

Ceullar Components (22)

Bioassays (171)

Research

Studies (227)

Market Indicators

Research Demand Index: 26.68

Study Types

Related Drugs (585)

Related Conditions (136)