3,3'-diindolylmethane profile

3,3'-Diindolylmethane (DIM) is a naturally occurring compound found in cruciferous vegetables like broccoli, cauliflower, and Brussels sprouts. It is formed when indole-3-carbinol (I3C), another compound found in these vegetables, is broken down in the body. DIM has garnered significant research interest due to its potential health benefits, particularly in the areas of cancer prevention and hormone regulation. Research suggests that DIM may exhibit anti-cancer activity by influencing the metabolism of estrogen, a hormone linked to certain types of cancers. It is thought to modulate estrogen receptor activity and potentially promote the detoxification of harmful estrogen metabolites. DIM's impact on estrogen metabolism has also led to investigations of its role in managing conditions like endometriosis and fibroids. Notably, DIM is synthesized by the acid-catalyzed dimerization of indole-3-carbinol. Studies exploring its efficacy and safety are ongoing, and further research is needed to fully understand its mechanisms of action and potential therapeutic applications.'

3,3'-diindolylmethane: anti-inflammatory from edible cruciferous vegetables; a cytochrome P-450 antagonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Products

ID Source	ID
PubMed CID	3071
CHEMBL ID	446452
CHEBI ID	50182
SCHEMBL ID	325162
MeSH ID	M0066345

Synonym
CBIOL_001839
BRD-K37846922-001-05-2
nsc-708486
NCI60_038418
BIO2_000010
CBDIVE_010856
BIO1_000614
BIO1_001103
BIO2_000490
BIO1_000125
SPECTRUM5_001955
3,3'-methylenebis(1h-indole)
1968-05-4
bis-1h-indol-3-ylmethane
CHEBI:50182 ,
diindolylmethane
HSCI1_000069
BSPBIO_003589
OPREA1_740951
IDI1_033760
DIM ,
nsc708486
NCGC00095348-01
NCGC00095348-03
NCGC00095348-02
NCGC00095348-04
1h-indole, 3,3'-methylenebis-
3,3'-methylenebis-1h-indole
3,3'-diindolymethane
ccris 5806
3,3'-diindolylmethane
KBIO3_000020
KBIOGR_000010
KBIOSS_000010
KBIO2_000010
KBIO3_000019
KBIO3_003002
KBIO2_005146
KBIO2_002578
SPBIO_001722
SPECTRUM2_001711
SPECTRUM3_001989
SPECTRUM1505331
OPREA1_472633
BSPBIO_001290
NCGC00095348-05
NCGC00095348-06
3,3,-diindolylmethane
D-3720
3-diindolyl methane
STK263696
3,3'-methanediylbis(1h-indole)
3,3'-di(indol-3-yl)methane
AC-11611
HMS1989A12
arundine
3,3-diindolylmethane
CHEMBL446452
BML3-F11
HMS1361A12
HMS1791A12
M1399
3,3'-methylenediindole
di-3-indolylmethane
3-(1h-indol-3-ylmethyl)-1h-indole
AKOS003627372
di(1h-indol-3-yl)methane
S4728
CCG-39861
ssz9hqt61z ,
hb 236
infemin
plant indole
unii-ssz9hqt61z
FT-0614061
NCGC00095348-07
AM84671
diindolylmethane, 3,3'-
diindolylmethane [vandf]
3,3'-diindolylmethane [who-dd]
GR-207
HY-15758
CS-1652
SCHEMBL325162
KS-5266
3,3'-di-indolylmethane
smr001828114
MLS006011847
3,3'-diindolylmethane (dim)
HMS3402A12
mfcd00195766
DTXSID8037047
3,3'-diindolylmethane, aldrichcpr
3,3'-diindolylmethane, >=98% (hplc)
gtpl11208
3,3'-diindolylmethane, analytical standard
di(3-indolyl)methane
DB11875
diidolylmethane
Q4634053
SY038972
BCP00470
BRD-K37846922-001-09-4
BRD-K37846922-001-06-0
A16321
SB16901
33'-diindolylmethane
3,3 inverted exclamation marka-diindolylmethane
33diindolylmethyle
EN300-1717487
3-[(1h-indol-3-yl)methyl]-1h-indole
3-3-diindolylmethane
dim;arundine;hb 236
Z56791159

Excerpt	Reference	Relevance
" This study examined the potential of these phytochemicals to reduce the adverse effects of E2 on PCa."	( 3,3'-Diindolylmethane and genistein decrease the adverse effects of estrogen in LNCaP and PC-3 prostate cancer cells. Auborn, KJ; Bradlow, HL; Sepkovic, D; Smith, S, 2008)	1.79
"Diindolylmethane seems to have no adverse affects on the rat even when given in doses 3x what we propose to be therapeutic."	( A controlled safety study of diindolylmethane in the immature rat model. Elackattu, AP; Feng, L; Wang, Z, 2009)	0.35
" Although extensive studies have only focused on DIM's beneficial effects, the toxic effects of DIM on the immune systems have not been clearly elucidated."	( 3,3'-Diindolylmethane induces immunotoxicity via splenocyte apoptosis in neonatal mice. Cho, A; Cho, SD; Islam, MR; Kim, B; Kim, J; Kim, JH; Lee, JW; Lim, CW; Roh, YS, 2011)	1.81

Excerpt	Reference	Relevance
" A physiologically based pharmacokinetic (PBPK) model was developed to characterize the pharmacokinetic properties of the two different formulations."	( Physiological modeling of formulated and crystalline 3,3'-diindolylmethane pharmacokinetics following oral administration in mice. Anderton, MJ; Gescher, A; Mager, DE; Manson, MM; Steward, WP; Verschoyle, R; Williams, ML, 2004)	0.57
" Mean Cmax for DIM increased from 61 ng/mL at the 400-mg I3C dose to 607 ng/mL following a 1,000-mg dose."	( Single-dose and multiple-dose administration of indole-3-carbinol to women: pharmacokinetics based on 3,3'-diindolylmethane. Arneson, DW; Crowell, JA; Gray, JC; Hurwitz, A; Mayo, MS; Putnam, WC; Reed, GA; Smith, HJ; Sullivan, DK, 2006)	0.55
" Despite rapidly increasing knowledge regarding mechanisms responsible for the chemopreventive properties of DIM-C-pPhC6H5, there have been relatively few studies determining the absorption and pharmacokinetic properties of DIM-C-pPhC6H5 to explore its clinical utility."	( Pharmacokinetic evaluation and in vitro-in vivo correlation (IVIVC) of novel methylene-substituted 3,3' diindolylmethane (DIM). Chougule, MB; Patel, AR; Safe, S; Singh, M; Spencer, SD, 2012)	0.38
"The pharmacokinetic absorption model presented represents a useful basis for obtaining plasma level predictability for poorly bioavailable, highly lipophilic drugs, such as the DIM analog DIM-C-pPhC6H5."	( Pharmacokinetic evaluation and in vitro-in vivo correlation (IVIVC) of novel methylene-substituted 3,3' diindolylmethane (DIM). Chougule, MB; Patel, AR; Safe, S; Singh, M; Spencer, SD, 2012)	0.38
" We postulated that the pharmacokinetic behavior of C-DIM compounds after oral administration would correlate with neuroprotective efficacy in vivo in a mouse model of Parkinson's disease."	( Neuroprotective efficacy and pharmacokinetic behavior of novel anti-inflammatory para-phenyl substituted diindolylmethanes in a mouse model of Parkinson's disease. Colagiovanni, D; De Miranda, BR; Gustafson, DL; Hansen, RJ; Lunghofer, PJ; Miller, JA; Safe, S; Tjalkens, RB, 2013)	0.39
" In this study, we sought to characterize the pharmacokinetics of DIM and to build a pharmacokinetic (PK) and pharmacodynamic (PD) model of the DIM-induced gene expression of phase II drug metabolizing enzymes (DME), which potentially links DIM's molecular effects to its in vivo chemopreventive efficacy."	( Pharmacokinetics and pharmacodynamics of 3,3'-diindolylmethane (DIM) in regulating gene expression of phase II drug metabolizing enzymes. Androulakis, IP; Boyanapalli, S; Gounder, M; Huang, Y; Kagan, L; Khor, TO; Kong, AN; Lin, H; Su, ZY; Wang, H; Wu, TY; Zhang, C, 2015)	0.68

Excerpt	Reference	Relevance
" Relative drug exposure and absorption parameters suggest that BioResponse-DIM exhibited approximately 50% higher bioavailability than the crystalline formulation."	( Physiological modeling of formulated and crystalline 3,3'-diindolylmethane pharmacokinetics following oral administration in mice. Anderton, MJ; Gescher, A; Mager, DE; Manson, MM; Steward, WP; Verschoyle, R; Williams, ML, 2004)	0.57
" We found that BioResponse DIM (B-DIM), a formulated DIM with higher bioavailability, inhibited angiogenesis and invasion by reducing the bioavailability of vascular endothelial growth factor (VEGF) via repressing extracellular matrix-degrading proteases, such as matrix metalloproteinase (MMP)-9 and urokinase-type plasminogen activator (uPA), in human prostate cancer cells and reduced vascularity (angiogenesis) in vivo using Matrigel plug assay."	( Inhibition of angiogenesis and invasion by 3,3'-diindolylmethane is mediated by the nuclear factor-kappaB downstream target genes MMP-9 and uPA that regulated bioavailability of vascular endothelial growth factor in prostate cancer. Banerjee, S; Kong, D; Li, Y; Sarkar, FH; Wang, Z, 2007)	0.6
" However, some of these agents have poor bioavailability and many of the in-depth studies into their mechanisms of action have been carried out in vitro using doses which are unachievable in humans."	( Predicting the physiological relevance of in vitro cancer preventive activities of phytochemicals. Andreadi, CK; Foreman, BE; Howells, LM; Hudson, EA; Manson, MM; Moiseeva, EP; Neal, CP; Sun, YY, 2007)	0.34
" In the present study, we determined the effects of 3,3'-diindolylmethane (Bioresponse BR-DIM referred to as B-DIM), a formulated DIM with greater bioavailability on cell viability and apoptosis with erlotinib in vitro and in vivo using an orthotopic animal tumor model."	( Apoptosis-inducing effect of erlotinib is potentiated by 3,3'-diindolylmethane in vitro and in vivo using an orthotopic model of pancreatic cancer. Ahmad, A; Ali, S; Banerjee, S; El-Rayes, BF; Philip, PA; Sarkar, FH, 2008)	0.84
" An important development has been the availability of DIM formulation with superior bioavailability for humans."	( Attenuation of multi-targeted proliferation-linked signaling by 3,3'-diindolylmethane (DIM): from bench to clinic. Banerjee, S; Bao, B; Hillman, GG; Kong, D; Sarkar, FH; Wang, Z, )	0.37
" The saturation model obtained accounts for a nonlinear change in C(max)/Dose, and the absolute bioavailability (0."	( Pharmacokinetic evaluation and in vitro-in vivo correlation (IVIVC) of novel methylene-substituted 3,3' diindolylmethane (DIM). Chougule, MB; Patel, AR; Safe, S; Singh, M; Spencer, SD, 2012)	0.38
" We previously reported that a formulated DIM (BR-DIM; hereafter referred as B-DIM) with higher bioavailability was able to induce apoptosis and inhibit cell growth, angiogenesis, and invasion of prostate cancer cells."	( Activation of AMP-activated protein kinase by 3,3'-Diindolylmethane (DIM) is associated with human prostate cancer cell death in vitro and in vivo. Banerjee, S; Chen, D; Cui, QC; Dou, QP; Kong, D; Sarkar, FH, 2012)	0.64
"The main reasons for the failure of most chemopreventive agents during clinical trials are poor in vivo bioavailability and dose-limiting side effects."	( Chemoprevention of lung tumorigenesis by intranasally administered diindolylmethane in A/J mice. Kassie, F; Melkamu, T; Qian, X; Song, JM; Upadhyaya, P, 2013)	0.39
" Oral bioavailability of each compound ranged from 6% (C-DIM8) to 42% (C-DIM12)."	( Neuroprotective efficacy and pharmacokinetic behavior of novel anti-inflammatory para-phenyl substituted diindolylmethanes in a mouse model of Parkinson's disease. Colagiovanni, D; De Miranda, BR; Gustafson, DL; Hansen, RJ; Lunghofer, PJ; Miller, JA; Safe, S; Tjalkens, RB, 2013)	0.39
" Caco-2 permeability studies resulted in poor permeability and poor oral bioavailability was demonstrated by pharmacokinetic studies."	( Novel diindolylmethane derivatives based NLC formulations to improve the oral bioavailability and anticancer effects in triple negative breast cancer. Doddapaneni, R; Godugu, C; Safe, SH; Singh, M, 2016)	0.43
"The evaluation of the bioavailability of bioactive compounds from cruciferous foods is one challenge in the design of clinical trials for studying their functionality."	( Bioavailability and new biomarkers of cruciferous sprouts consumption. Baenas, N; García-Viguera, C; Moreno, DA; Suárez-Martínez, C, 2017)	0.46
" Further in vivo studies were carried out to analyze the biodistribution of the drug, blood biochemical analysis and bioavailability of the drug."	( Natural polymer functionalized graphene oxide for co-delivery of anticancer drugs: In-vitro and in-vivo. Andrews, NG; Deb, A; Raghavan, V, 2018)	0.48
" However, low stability and bioavailability limit its application."	( Interactions between β-Lactoglobulin and 3,3'-Diindolylmethane in Model System. Guo, M; Sun, X; Wang, C; Wang, H; Zhou, X, 2019)	0.78
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."	( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)	0.51

Excerpt	Relevance	Reference
" I33' may have accounted for Vg increases observed in trout fed I3C as it is present in liver after oral dosing at concentrations (70 microM) expected to maximally induce Vg."	( 3,3'-diindolylmethane, a major condensation product of indole-3-carbinol, is a potent estrogen in the rainbow trout. Carlson, DB; Katchamart, S; Shilling, AD; Williams, DE, 2001)	1.75
" The concentrations of DIM required to suppress CSCs formation are in the close range to those achievable in human plasma after oral dosing of the compound."	( Diindolilmethane (DIM) selectively inhibits cancer stem cells. Alakhov, V; Iourtchenco, L; Kiselev, V; Li, S; Liu, LF; Muyjnek, E; Semov, A; Su, X; Xu, Y, 2012)	0.38
" We report that administration of DIM in a multidose schedule protected rodents against lethal doses of total body irradiation up to 13 Gy, whether DIM dosing was initiated before or up to 24 h after radiation."	( DIM (3,3'-diindolylmethane) confers protection against ionizing radiation by a unique mechanism. Brown, ML; Dritschilo, A; Fan, S; Jiao, Y; Meng, Q; Rosen, EM; Sarkar, FH; Xu, J; Zhang, X; Zhao, L, 2013)	0.9

Product Category	Products
Active Lifestyle & Fitness	10
Pet Supplies	1
Professional Supplements	5
Vitamins & Supplements	13

Product	Brand	Category	Compounds Matched from Ingredients	Date Retrieved
Action Labs DIM for Men - Alpha Advantage -- 30 VegCaps	Action Labs	Active Lifestyle & Fitness	Diindolylmethane	2024-11-29 10:47:42
ALLMAX Nutrition DIM -- 60 Veggie Capsules	ALLMAX Nutrition	Active Lifestyle & Fitness	3,3'-Diindolymethane	2024-11-29 10:47:42
Animal Power Balance -- 30 Packs	Animal	Active Lifestyle & Fitness	Diindolylmethane, Biotin, Chromium, Folate, phytonadione, Vitamin K	2024-11-29 10:47:42
Animal Stak All-in-1 Pill Packs -- 21 Packets	Animal	Active Lifestyle & Fitness	Diindolylmethane, Astaxanthin, Coenzyme Q10, L-Glutamine, Glycine, Vitamin B6, Quercetin Dihydrate, Alpha-Lipoic Acid, Vitamin B6	2024-11-29 10:47:42
Bark & Whiskers Adrenal Support Supplement Powder for Dogs & Cats -- 3.17 oz	Bark & Whiskers	Pet Supplies	Diindolylmethane, Melatonin	2024-11-29 10:47:42
Codeage Liposomal DIM-E - Diindolylmethane Antioxidant SGS Vitamin E Tocopherols & Isomers -- 120 Capsules	Codeage	Professional Supplements	Diindolylmethane, Gamma, Beta	2024-11-29 10:47:42
Cutler Nutrition Triumph Testosterone Booster -- 56 Vegetarian Capsules	Cutler Nutrition	Active Lifestyle & Fitness	Diindolylmethane	2024-11-29 10:47:42
DaVinci Laboratories DIMPRO -- 150 mg - 60 Capsules	DaVinci Laboratories	Professional Supplements	diindolylmethane	2024-11-29 10:47:42
DaVinci Laboratories DIMPRO -- 60 Capsules	DaVinci Laboratories	Professional Supplements	diindolylmethane	2024-11-29 10:47:42
DaVinci Laboratories Hair Effects™ -- 90 Capsules	DaVinci Laboratories	Professional Supplements	diindolylmethane, Biotin, L-Cysteine, Methylsulfonylmethane, Gamma Linoleic Acid	2024-11-29 10:47:42
Emerald Labs Estrogen Detox for Men and Women -- 60 Vegetable Caps	Emerald Labs	Vitamins & Supplements	Diindolylmethane, Vitamin B12	2024-11-29 10:47:42
Evlution Nutrition DIM200 -- 60 Veggie Capsules	Evlution Nutrition	Vitamins & Supplements	Diindolylmethane	2024-11-29 10:47:42
Force Factor Fundalmentals DIM -- 30 Capsules	Force Factor	Active Lifestyle & Fitness	DIM, Selenium	2024-11-29 10:47:42
Natural Factors WomenSense EstroSense® -- 60 Vegetarian Capsules	Natural Factors	Vitamins & Supplements	Di-Indolylmethane, Curcumin, Microcrystalline cellulose, Indole-3-Carbinol, Lycopene, Carnosic Acid, Sulforaphane	2024-11-29 10:47:42
Nutricost DIM Capsules -- 300 mg - 120 Capsules	Nutricost	Vitamins & Supplements	DIM	2024-11-29 10:47:42
Olympian Labs DIM -- 60 Vegetarian Capsules	Olympian Labs	Vitamins & Supplements	DIM, microcrystalline cellulose	2024-11-29 10:47:42
Olympian Labs DIM-150 -- 30 Vegetarian Capsules	Olympian Labs	Vitamins & Supplements	DIM, microcrystalline cellulose	2024-11-29 10:47:42
Olympian Labs PSN DIM -- 100 mg - 120 Capsules	Olympian Labs	Vitamins & Supplements	DIM, microcrystalline cellulose	2024-11-29 10:47:42
Olympian Labs PSN DIM -- 150 mg - 30 Vegetarian Capsules	Olympian Labs	Vitamins & Supplements	DIM	2024-11-29 10:47:42
Olympian Labs PSN DIM -- 250 mg - 30 Capsules	Olympian Labs	Active Lifestyle & Fitness	DIM, microcrystalline cellulose	2024-11-29 10:47:42
Olympian Labs PSN DIM -- 250 mg - 30 Vegetarian Capsules	Olympian Labs	Vitamins & Supplements	DIM, microcrystalline cellulose	2024-11-29 10:47:42
Olympian Labs PSN Testosterone Booster -- 60 Capsules	Olympian Labs	Active Lifestyle & Fitness	DIM, DHEA, microcrystalline cellulose, Vitamin B6, Vitamin B6	2024-11-29 10:47:42
Snap Supplements Testo Booster -- 60 Capsules	Snap Supplements	Vitamins & Supplements	Diindolylmethane, Vitamin D3, Vitamin B3	2024-11-29 10:47:42
Source Naturals DIM -- 200 mg - 120 Tablets	Source Naturals	Vitamins & Supplements	Diindolylmethane, Vitamin E, Vitamin E, Microcrystalline cellulose, stearic acid	2024-11-29 10:47:42
Source Naturals DIM -- 200 mg - 60 Tablets	Source Naturals	Vitamins & Supplements	Diindolylmethane, Vitamin E, Vitamin E, Microcrystalline cellulose, stearic acid	2024-11-29 10:47:42
Sunwarrior Sport Active Creatine for Her Raspberry Elderberry Lemonade -- 14.1 oz	Sunwarrior	Active Lifestyle & Fitness	DIM, citric acid, citric acid, rebaudioside A	2024-11-29 10:47:42
Thorne Research Hormone Advantage -- 60 Capsules	Thorne Research	Professional Supplements	Diindolylmethane	2024-11-29 10:47:42
Zhou Boost Elite® -- 90 Veggie Capsules	Zhou	Active Lifestyle & Fitness	Diindolylmethane	2024-11-29 10:47:42
Zhou DIM Active™ with Activated Broccoli Extract -- 60 Veggie Capsules	Zhou	Vitamins & Supplements	DIM, Vitamin C, Vitamin E, Vitamin E	2024-11-29 10:47:42

Role	Description
antineoplastic agent	A substance that inhibits or prevents the proliferation of neoplasms.
P450 inhibitor	An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.
[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
indoles	Any compound containing an indole skeleton.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
indole glucosinolate activation (herbivore attack)	3	20
indole glucosinolate activation (herbivore attack)	4	24

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASE	Homo sapiens (human)	Potency	35.4813	0.0040	23.8416	100.0000	AID485290
Chain A, Ferritin light chain	Equus caballus (horse)	Potency	11.2202	5.6234	17.2929	31.6228	AID485281
USP1 protein, partial	Homo sapiens (human)	Potency	56.2341	0.0316	37.5844	354.8130	AID504865
Microtubule-associated protein tau	Homo sapiens (human)	Potency	29.0027	0.1800	13.5574	39.8107	AID1460; AID1468
regulator of G-protein signaling 4	Homo sapiens (human)	Potency	0.1337	0.5318	15.4358	37.6858	AID504845
EWS/FLI fusion protein	Homo sapiens (human)	Potency	6.4514	0.0013	10.1577	42.8575	AID1259252; AID1259253; AID1259255; AID1259256
euchromatic histone-lysine N-methyltransferase 2	Homo sapiens (human)	Potency	17.0157	0.0355	20.9770	89.1251	AID504332
vitamin D3 receptor isoform VDRA	Homo sapiens (human)	Potency	50.1187	0.3548	28.0659	89.1251	AID504847
cytochrome P450 3A4 isoform 1	Homo sapiens (human)	Potency	39.8107	0.0316	10.2792	39.8107	AID884; AID885
Gamma-aminobutyric acid receptor subunit pi	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit beta-1	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit delta	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit gamma-2	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-5	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-3	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit gamma-1	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-2	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-4	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit gamma-3	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-6	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-1	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit beta-3	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit beta-2	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
GABA theta subunit	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit epsilon	Rattus norvegicus (Norway rat)	Potency	39.8107	1.0000	12.2248	31.6228	AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Aryl hydrocarbon receptor	Mus musculus (house mouse)	EC50 (µMol)	78.0000	0.0000	0.0000	0.0000	AID1527840
Aryl hydrocarbon receptor	Mus musculus (house mouse)	Kd	0.0900	0.0008	0.0454	0.0900	AID1527833
Nuclear receptor ROR-gamma	Homo sapiens (human)	EC50 (µMol)	78.0000	0.0200	0.7035	9.0000	AID1527840
G-protein coupled receptor 84	Mus musculus (house mouse)	EC50 (µMol)	4.2700	4.2700	4.2700	4.2700	AID1707050
G-protein coupled receptor 84	Homo sapiens (human)	EC50 (µMol)	3.3129	0.0890	3.8687	10.0000	AID1447407; AID1447408; AID1447416; AID1447417; AID1447418; AID1447419; AID1546371; AID1546372; AID1546374; AID1546376; AID1546378; AID1546389; AID1546390; AID1546392
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
G-protein coupled receptor 84	Homo sapiens (human)	Kb	0.8800	0.8800	0.8800	0.8800	AID1447422
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
negative regulation of transcription by RNA polymerase II	Nuclear receptor ROR-gamma	Homo sapiens (human)
xenobiotic metabolic process	Nuclear receptor ROR-gamma	Homo sapiens (human)
regulation of glucose metabolic process	Nuclear receptor ROR-gamma	Homo sapiens (human)
regulation of steroid metabolic process	Nuclear receptor ROR-gamma	Homo sapiens (human)
intracellular receptor signaling pathway	Nuclear receptor ROR-gamma	Homo sapiens (human)
circadian regulation of gene expression	Nuclear receptor ROR-gamma	Homo sapiens (human)
cellular response to sterol	Nuclear receptor ROR-gamma	Homo sapiens (human)
positive regulation of circadian rhythm	Nuclear receptor ROR-gamma	Homo sapiens (human)
regulation of fat cell differentiation	Nuclear receptor ROR-gamma	Homo sapiens (human)
positive regulation of DNA-templated transcription	Nuclear receptor ROR-gamma	Homo sapiens (human)
adipose tissue development	Nuclear receptor ROR-gamma	Homo sapiens (human)
T-helper 17 cell differentiation	Nuclear receptor ROR-gamma	Homo sapiens (human)
regulation of transcription by RNA polymerase II	Nuclear receptor ROR-gamma	Homo sapiens (human)
biological_process	G-protein coupled receptor 84	Homo sapiens (human)
neuropeptide signaling pathway	G-protein coupled receptor 84	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specific	Nuclear receptor ROR-gamma	Homo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specific	Nuclear receptor ROR-gamma	Homo sapiens (human)
DNA-binding transcription factor activity	Nuclear receptor ROR-gamma	Homo sapiens (human)
protein binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
oxysterol binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
zinc ion binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
ligand-activated transcription factor activity	Nuclear receptor ROR-gamma	Homo sapiens (human)
sequence-specific double-stranded DNA binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
nuclear receptor activity	Nuclear receptor ROR-gamma	Homo sapiens (human)
urotensin II receptor activity	G-protein coupled receptor 84	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
plasma membrane	Gamma-aminobutyric acid receptor subunit gamma-2	Rattus norvegicus (Norway rat)
nucleus	Nuclear receptor ROR-gamma	Homo sapiens (human)
nucleoplasm	Nuclear receptor ROR-gamma	Homo sapiens (human)
nuclear body	Nuclear receptor ROR-gamma	Homo sapiens (human)
chromatin	Nuclear receptor ROR-gamma	Homo sapiens (human)
nucleus	Nuclear receptor ROR-gamma	Homo sapiens (human)
plasma membrane	Gamma-aminobutyric acid receptor subunit alpha-1	Rattus norvegicus (Norway rat)
plasma membrane	Gamma-aminobutyric acid receptor subunit beta-2	Rattus norvegicus (Norway rat)
plasma membrane	G-protein coupled receptor 84	Homo sapiens (human)
specific granule membrane	G-protein coupled receptor 84	Homo sapiens (human)
tertiary granule membrane	G-protein coupled receptor 84	Homo sapiens (human)
receptor complex	G-protein coupled receptor 84	Homo sapiens (human)
plasma membrane	G-protein coupled receptor 84	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (139)

Assay ID	Title	Year	Journal	Article
AID1347411	qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Mechanism Interrogation Plate v5.0 (MIPE) Libary	2020	ACS chemical biology, 07-17, Volume: 15, Issue:7	High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1296008	Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening	2020	SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1	Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347093	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347101	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347105	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347108	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347107	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347094	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347090	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347096	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347100	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347098	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347095	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347097	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID1347103	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630	Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay	2021	Cell reports, 04-27, Volume: 35, Issue:4	A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347102	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347154	Primary screen GU AMC qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347086	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347092	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347106	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347083	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347089	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347104	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347099	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1346986	P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987	P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347091	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1447429	Activation of AhR in human HepG2 cells assessed as induction of CYP1A1 mRNA expression after 18 hrs by RT-PCR method
AID582000	Binding affinity to recombinant wild type Leishmania donovani AG83 topoisomerase 1b after 24 hrs by equilibrium dialysis method	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID582003	Binding affinity to recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b large subunit F270L, K430N mutant after 24 hrs by equilibrium dialysis method	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID308569	Growth promoting activity in Oryza sativa assessed as shoot length at 125 ppm on day 5	2007	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17	Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.
AID581976	Antimicrobial activity against wild type Leishmania donovani AG83 transfected with drug-resistant Leishmania donovani LdDR50 topoisomerase 1 F270L, K430N mutant in large subunit and N184S mutant in small subunit assessed as inhibition of parasite growth a	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID1546378	Agonist activity at human Gi1alpha-coupled GPR84 expressed in baculovirus infected Sf9 insect cells assessed as stimulation of [35S]GTPgammaS binding measured after 30 mins by liquid scintillation counting method	2020	Journal of medicinal chemistry, 03-12, Volume: 63, Issue:5	An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights.
AID1546371	Agonist activity at human N-terminal FLAG-tagged GPR84 receptor stably expressed in CHO cells assessed as inhibition of forskolin-induced cAMP production preincubated for 20 mins followed by forskolin addition and measured after 20 mins	2020	Journal of medicinal chemistry, 03-12, Volume: 63, Issue:5	An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights.
AID398042	Antifungal activity against Mucor miehei by agar diffusion method	2003	Journal of natural products, Nov, Volume: 66, Issue:11	New indole alkaloids from the North Sea bacterium Vibrio parahaemolyticus Bio249.
AID581987	Inhibition of recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b large subunit F270L mutant and small subunit N184S mutant-mediated relaxation of supercoiled pBluescript SK(+) DNA at up to 50 uM after 30 mins using ethidium bromide sta	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID582001	Ratio of KD for drug-resistant Leishmania donovani LdDR50 topoisomerase 1b to KD for wild type Leishmania donovani AG83 topoisomerase 1b	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581855	Antimicrobial activity against wild type Leishmania donovani AG83 transfected with drug-resistant Leishmania donovani LdDR50 topoisomerase 1 F270L, N184S mutant in large subunit assessed as inhibition of parasite growth at 20 uM after 24 hrs by MTT assay	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID1447425	Agonist activity at human FFAR4 expressed in CHO cells assessed as beta-arrestin recruitment at 10 uM after 90 mins by beta-galactosidase complementation assay
AID398038	Antibacterial activity against Staphylococcus aureus by agar diffusion method	2003	Journal of natural products, Nov, Volume: 66, Issue:11	New indole alkaloids from the North Sea bacterium Vibrio parahaemolyticus Bio249.
AID308566	Growth promoting activity in Oryza sativa assessed as root length at 31.25 ppm on day 5	2007	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17	Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.
AID581985	Inhibition of recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b wild type small subunit and large subunit F270L mutant-mediated relaxation of supercoiled pBluescript SK(+) DNA at up to 50 uM after 30 mins using ethidium bromide staini	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581982	Inhibition of recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b-mediated relaxation of supercoiled pBluescript SK(+) DNA at up to 50 uM after 30 mins using ethidium bromide staining	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581981	Antimicrobial activity against wild type Leishmania donovani AG83 transfected with drug-resistant Leishmania donovani LdDR50 topoisomerase 1 wild type large subunit and N184S mutant in small subunit assessed as inhibition of parasite growth at 20 uM after	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581854	Antimicrobial activity against wild type Leishmania donovani AG83 assessed as inhibition of parasite growth after 24 hrs by MTT assay	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581978	Drug uptake in wild type Leishmania donovani AG83 at 20 uM after 30 mins by spectrophotometric analysis	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID1447408	Agonist activity at human GPR84 expressed in CHO cells assessed as beta-arrestin recruitment after 90 mins by beta-galactosidase complementation assay
AID581997	Inhibition of recombinant Leishmania donovani AG83 topoisomerase 1b-mediated religation of 14-mer/25-mer suicide DNA substrate at 20 uM after 120 mins by PAGE analysis	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581989	Inhibition of recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b large subunit K430N mutant and small subunit N184S mutant-mediated relaxation of supercoiled pBluescript SK(+) DNA at up to 50 uM after 30 mins using ethidium bromide sta	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581998	Inhibition of recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b small subunit N184S mutant-mediated religation of 14-mer/25-mer suicide DNA substrate at 20 uM after 120 mins by PAGE analysis	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID1546389	Agonist activity at recombinant human HA-tagged GPR84 stably expressed in HEK293 cells assessed as stimulation of [35S]GTPgammaS binding measured after 30 mins by liquid scintillation counting method	2020	Journal of medicinal chemistry, 03-12, Volume: 63, Issue:5	An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights.
AID582007	Binding affinity to Leishmania donovani small subunit of topoisomerase 1b	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID1447416	Positive allosteric modulation of Gi coupled human GPR84 expressed in CHO cells assessed as potentiation of decanoic acid-induced inhibition of forskolin-induced cAMP accumulation by measuring decanoic acid EC50 at 0.1 uM after 15 mins in presence of [3H]
AID660428	Growth inhibition of human MCF7 cells after 48 hrs by MTT assay	2012	Journal of medicinal chemistry, Feb-23, Volume: 55, Issue:4	Synthesis and evaluation of the cytotoxicities of tetraindoles: observation that the 5-hydroxy tetraindole (SK228) induces G₂ arrest and apoptosis in human breast cancer cells.
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.
AID308576	Growth promoting activity in Oryza sativa assessed as root length at 1000 ppm on day 5	2007	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17	Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.
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.
AID581988	Inhibition of recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b wild type small subunit and large subunit K430N mutant-mediated relaxation of supercoiled pBluescript SK(+) DNA at up to 50 uM after 30 mins using ethidium bromide staini	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581980	Antimicrobial activity against wild type Leishmania donovani AG83 transfected with drug-resistant Leishmania donovani LdDR50 topoisomerase 1 K430N mutant in large subunit and wild type small subunit assessed as inhibition of parasite growth at 20 uM after	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581979	Antimicrobial activity against wild type Leishmania donovani AG83 transfected with drug-resistant Leishmania donovani LdDR50 topoisomerase 1 K430N mutant in large subunit and N184S mutant in small subunit assessed as inhibition of parasite growth at 20 uM	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID398039	Antibacterial activity against Bacillus subtilis by agar diffusion method	2003	Journal of natural products, Nov, Volume: 66, Issue:11	New indole alkaloids from the North Sea bacterium Vibrio parahaemolyticus Bio249.
AID436767	Cytotoxicity against human ME18 cells for 48 hrs by MTT assay	2009	European journal of medicinal chemistry, Oct, Volume: 44, Issue:10	Novel 3,3'-diindolylmethane derivatives: synthesis and cytotoxicity, structural characterization in solid state.
AID398040	Antibacterial activity against Streptomyces viridochromogenes by agar diffusion method	2003	Journal of natural products, Nov, Volume: 66, Issue:11	New indole alkaloids from the North Sea bacterium Vibrio parahaemolyticus Bio249.
AID1447419	Positive allosteric modulation of Gi coupled human GPR84 expressed in CHO cells assessed as potentiation of decanoic acid-induced inhibition of forskolin-induced cAMP accumulation by measuring decanoic acid EC50 at 3 uM after 15 mins in presence of [3H]-c
AID1447427	Antagonist activity at human FFAR4 expressed in CHO cells assessed as inhibition of TUG-89-induced beta-arrestin recruitment at 10 uM preincubated for 30 mins followed by TUG-89 addition measured after 90 mins by beta-galactosidase complementation assay
AID1546391	Positive allosteric modulation of recombinant human GPR84 expressed in CHO cell membranes co-expressing beta-arrestin2 assessed as increase in [3H]PSB-1584 binding measured after 6 hrs by scintillation counting method relative to control	2020	Journal of medicinal chemistry, 03-12, Volume: 63, Issue:5	An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights.
AID1447406	Agonist activity at Gi coupled human GPR84 expressed in CHO cells assessed as inhibition of forskolin-induced cAMP accumulation at 10 uM after 15 mins in presence of [3H]-cAMP by radiometric assay relative to decanoic acid
AID1447438	Stability of the compound in pH 1.2 artificial gastric fluid containing HCl, NaCl and pepsin assessed as parent compound remaining at 100 uM after 2 hrs by HPLC-MS analysis
AID1447424	Agonist activity at Gq protein coupled human FFAR1 expressed in human 1321N1 cells assessed as induction of intracellular calcium level at 10 uM measured at 1.2 secs time interval by Fluo-4-AM dye based fluorescence assay
AID1439693	Cytotoxicity against human U87 cells assessed as decrease in cell proliferation after 72 hrs by SRB assay	2017	Bioorganic & medicinal chemistry letters, 04-01, Volume: 27, Issue:7	Preliminary SAR on indole-3-carbinol and related fragments reveals a novel anticancer lead compound against resistant glioblastoma cells.
AID581856	Antimicrobial activity against wild type Leishmania donovani AG83 transfected with drug-resistant Leishmania donovani LdDR50 topoisomerase 1 F270L, K430N mutant in large subunit assessed as inhibition of parasite growth at 20 uM after 24 hrs by MTT assay	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID1447435	Stability of the compound in 1 mM sodium hydroxide solution at 100 uM at pH 11 up to 24 hrs by HPLC-MS analysis
AID1527833	Displacement of 2-azido-3-[125I]7,8-dibromodibenzo-pdioxin from C57BL/6J mouse liver AhR	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Targeting Aryl hydrocarbon receptor for next-generation immunotherapies: Selective modulators (SAhRMs) versus rapidly metabolized ligands (RMAhRLs).
AID581852	Ratio of antimicrobial activity against drug-resistant Leishmania donovani LdDR50 to antimicrobial activity against wild type Leishmania donovani AG83	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581994	Effect on recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b small subunit N184S mutant-mediated cleavage of 25-mer duplex oligonucleotide at 5 uM after 30 mins by PAGE analysis	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID436769	Cytotoxicity against human WS1 cells for 48 hrs by MTT assay	2009	European journal of medicinal chemistry, Oct, Volume: 44, Issue:10	Novel 3,3'-diindolylmethane derivatives: synthesis and cytotoxicity, structural characterization in solid state.
AID398037	Antibacterial activity against Escherichia coli by agar diffusion method	2003	Journal of natural products, Nov, Volume: 66, Issue:11	New indole alkaloids from the North Sea bacterium Vibrio parahaemolyticus Bio249.
AID581991	Effect on recombinant wild type Leishmania donovani AG83 topoisomerase 1b-mediated cleavage of 25-mer duplex oligonucleotide at 20 uM after 30 mins by PAGE analysis	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID977602	Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	2013	Molecular pharmacology, Jun, Volume: 83, Issue:6	Structure-based identification of OATP1B1/3 inhibitors.
AID582006	Binding affinity to Leishmania donovani large subunit of topoisomerase 1b	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581993	Effect on recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b large subunit K430N mutant-mediated cleavage of 25-mer duplex oligonucleotide at 20 uM after 30 mins by PAGE analysis	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID1447439	Stability of the compound in pH 1.2 artificial gastric fluid containing HCl, NaCl and pepsin assessed as parent compound remaining at 100 uM after 4 hrs by HPLC-MS analysis
AID1447418	Positive allosteric modulation of Gi coupled human GPR84 expressed in CHO cells assessed as potentiation of decanoic acid-induced inhibition of forskolin-induced cAMP accumulation by measuring decanoic acid EC50 at 1 uM after 15 mins in presence of [3H]-c
AID1546392	Positive allosteric modulation of recombinant human GPR84 expressed in CHO cell membranes co-expressing beta-arrestin2 assessed as increase in [3H]PSB-1584 binding measured after 6 hrs by scintillation counting method	2020	Journal of medicinal chemistry, 03-12, Volume: 63, Issue:5	An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights.
AID1447407	Agonist activity at Gi coupled human GPR84 expressed in CHO cells assessed as inhibition of forskolin-induced cAMP accumulation after 15 mins in presence of [3H]-cAMP by radiometric assay
AID1439694	Cytotoxicity against human U251 cells assessed as decrease in cell proliferation after 72 hrs by SRB assay	2017	Bioorganic & medicinal chemistry letters, 04-01, Volume: 27, Issue:7	Preliminary SAR on indole-3-carbinol and related fragments reveals a novel anticancer lead compound against resistant glioblastoma cells.
AID398041	Antifungal activity against Candida albicans by agar diffusion method	2003	Journal of natural products, Nov, Volume: 66, Issue:11	New indole alkaloids from the North Sea bacterium Vibrio parahaemolyticus Bio249.
AID308574	Growth promoting activity in Oryza sativa assessed as root length at 500 ppm on day 5	2007	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17	Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.
AID581983	Inhibition of recombinant wild type Leishmania donovani AG83 topoisomerase 1b-mediated relaxation of supercoiled pBluescript SK(+) DNA at 10 uM after 30 mins using ethidium bromide staining	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581857	Antimicrobial activity against wild type Leishmania donovani AG83 transfected with drug-resistant Leishmania donovani LdDR50 topoisomerase 1 F270Lmutant in large subunit assessed as inhibition of parasite growth at 20 uM after 24 hrs by MTT assay	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID582004	Binding affinity to recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b large subunit F270L mutant after 24 hrs by equilibrium dialysis method	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID308567	Growth promoting activity in Oryza sativa assessed as shoot length at 62.5 ppm on day 5	2007	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17	Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.
AID1546369	Displacement of [3H]PSB-1584 from recombinant human GPR84 expressed in CHO cell membranes co-expressing beta-arrestin2 measured after 6 hrs by scintillation counting method	2020	Journal of medicinal chemistry, 03-12, Volume: 63, Issue:5	An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights.
AID1447437	Stability of the compound in pH 1.2 artificial gastric fluid containing HCl, NaCl and pepsin assessed as parent compound remaining at 100 uM after 1 hr by HPLC-MS analysis
AID1546372	Agonist activity at human N-terminal FLAG-tagged GPR84 receptor stably expressed in CHO cell membranes assessed as stimulation of [35S]GTPgammaS binding incubated for 1 hr by liquid scintillation counting method	2020	Journal of medicinal chemistry, 03-12, Volume: 63, Issue:5	An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights.
AID1439695	Cytotoxicity against human IN1472 cells assessed as decrease in cell proliferation after 72 hrs by SRB assay	2017	Bioorganic & medicinal chemistry letters, 04-01, Volume: 27, Issue:7	Preliminary SAR on indole-3-carbinol and related fragments reveals a novel anticancer lead compound against resistant glioblastoma cells.
AID660427	Growth inhibition of human MDA-MB-231 cells after 48 hrs by MTT assay	2012	Journal of medicinal chemistry, Feb-23, Volume: 55, Issue:4	Synthesis and evaluation of the cytotoxicities of tetraindoles: observation that the 5-hydroxy tetraindole (SK228) induces G₂ arrest and apoptosis in human breast cancer cells.
AID1447428	Agonist activity at human GPR35 at 10 uM
AID1546376	Agonist activity at recombinant human N-terminal epitope tagged/C-terminal eYFP-fused FLAG-tagged GPR84 expressed in Flp-In TREx 293 cell membranes assessed as inhibition of forskolin-induced cAMP production measured after 30 mins by HTRF assay	2020	Journal of medicinal chemistry, 03-12, Volume: 63, Issue:5	An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights.
AID581990	Inhibition of recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b wild type large subunit and small subunit N184S mutant-mediated relaxation of supercoiled pBluescript SK(+) DNA at up to 50 uM after 30 mins using ethidium bromide staini	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581995	Effect on recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b small subunit N184S mutant-mediated cleavage of 25-mer duplex oligonucleotide at 20 uM after 30 mins by PAGE analysis	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581986	Inhibition of recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b wild type small subunit and large subunit F270L, K430N mutant-mediated relaxation of supercoiled pBluescript SK(+) DNA at up to 50 uM after 30 mins using ethidium bromide	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID292177	Antitumor activity against MCF7 cells	2007	Journal of medicinal chemistry, Jul-26, Volume: 50, Issue:15	Computer-aided rational drug design: a novel agent (SR13668) designed to mimic the unique anticancer mechanisms of dietary indole-3-carbinol to block Akt signaling.
AID308572	Growth promoting activity in Oryza sativa assessed as root length at 250 ppm on day 5	2007	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17	Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.
AID1447414	Ratio of EC50 for human GPR84 expressed in CHO cells assessed as beta-arrestin recruitment to EC50 for Gi coupled human GPR84 expressed in CHO cells assessed as inhibition of forskolin-induced cAMP accumulation
AID1447422	Positive allosteric modulation of Gi coupled human GPR84 expressed in CHO cells assessed as potentiation of decanoic acid-induced inhibition of forskolin-induced cAMP accumulation by measuring decanoic acid Kb after 15 mins in presence of [3H]-cAMP by rad
AID581977	Drug uptake in drug-resistant Leishmania donovani LdDR50 at 20 uM after 30 mins by spectrophotometric analysis	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID308573	Growth promoting activity in Oryza sativa assessed as shoot length at 500 ppm on day 5	2007	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17	Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.
AID1439696	Cytotoxicity against human IN1528 cells assessed as decrease in cell proliferation after 72 hrs by SRB assay	2017	Bioorganic & medicinal chemistry letters, 04-01, Volume: 27, Issue:7	Preliminary SAR on indole-3-carbinol and related fragments reveals a novel anticancer lead compound against resistant glioblastoma cells.
AID581992	Effect on recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b large subunit F270L mutant-mediated cleavage of 25-mer duplex oligonucleotide at 20 uM after 30 mins by PAGE analysis	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID581996	Inhibition of recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b large subunit F270L mutant-mediated religation of 14-mer/25-mer suicide DNA substrate at 20 uM after 120 mins by PAGE analysis	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID308570	Growth promoting activity in Oryza sativa assessed as root length at 125 ppm on day 5	2007	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17	Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.
AID1447409	Agonist activity at human GPR84 expressed in CHO cells assessed as beta-arrestin recruitment at 10 uM after 90 mins by beta-galactosidase complementation assay relative to embelin
AID1447412	Effect on forskolin-induced cAMP accumulation in CHO cells preincubated for 5 mins followed by forskolin addition measured after 15 mins in presence of [3H]-cAMP by radiometric assay
AID308571	Growth promoting activity in Oryza sativa assessed as shoot length at 250 ppm on day 5	2007	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17	Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.
AID1447434	Stability of the compound in water at 100 uM up to 24 hrs by HPLC-MS analysis
AID1546390	Agonist activity at human Gi1alpha-coupled GPR84 expressed in baculovirus infected Sf9 insect cells assessed as stimulation of [35S]GTPgammaS binding measured after 30 mins by top-count liquid scintillation counting method	2020	Journal of medicinal chemistry, 03-12, Volume: 63, Issue:5	An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights.
AID436768	Cytotoxicity against doxorubicin-resistant human ME18 cells for 48 hrs by MTT assay	2009	European journal of medicinal chemistry, Oct, Volume: 44, Issue:10	Novel 3,3'-diindolylmethane derivatives: synthesis and cytotoxicity, structural characterization in solid state.
AID1447436	Stability of the compound in 0.01% ammonia solution at 100 uM at pH 9 up to 24 hrs by HPLC-MS analysis
AID582002	Binding affinity to recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b large subunit F270L, K430N mutant and small subunit N184S mutant after 24 hrs by equilibrium dialysis method	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID582005	Binding affinity to recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b small subunit N184S mutant after 24 hrs by equilibrium dialysis method	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID308565	Growth promoting activity in Oryza sativa assessed as shoot length at 31.25 ppm on day 5	2007	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17	Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.
AID308575	Growth promoting activity in Oryza sativa assessed as shoot length at 1000 ppm on day 5	2007	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17	Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.
AID581999	Binding affinity to recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b after 24 hrs by equilibrium dialysis method	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID1447417	Positive allosteric modulation of Gi coupled human GPR84 expressed in CHO cells assessed as potentiation of decanoic acid-induced inhibition of forskolin-induced cAMP accumulation by measuring decanoic acid EC50 at 0.3 uM after 15 mins in presence of [3H]
AID308568	Growth promoting activity in Oryza sativa assessed as root length at 62.5 ppm on day 5	2007	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17	Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.
AID581984	Inhibition of recombinant drug-resistant Leishmania donovani LdDR50 topoisomerase 1b large subunit F270L, K430N mutant and small subunit N184S mutant-mediated relaxation of supercoiled pBluescript SK(+) DNA at up to 50 uM after 30 mins using ethidium brom	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID1527840	Displacement of 2-azido-3-[125I]7,8-dibromodibenzo-pdioxin from C57BL/6J mouse liver AhR relative to TCDD	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Targeting Aryl hydrocarbon receptor for next-generation immunotherapies: Selective modulators (SAhRMs) versus rapidly metabolized ligands (RMAhRLs).
AID1546374	Agonist activity at recombinant human N-terminal epitope tagged/C-terminal eYFP-fused FLAG-tagged GPR84 expressed in Flp-In TREx 293 cell membranes assessed as stimulation of [35S]GTPgammaS binding preincubated for 15 mins followed by [35S]GTPgammaS addit	2020	Journal of medicinal chemistry, 03-12, Volume: 63, Issue:5	An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights.
AID1439697	Cytotoxicity against human IN1760 cells assessed as decrease in cell proliferation after 72 hrs by SRB assay	2017	Bioorganic & medicinal chemistry letters, 04-01, Volume: 27, Issue:7	Preliminary SAR on indole-3-carbinol and related fragments reveals a novel anticancer lead compound against resistant glioblastoma cells.
AID1707050	Agonist activity at mouse Galphai2-coupled GPR84 expressed in human Flp-In-T-REx-293 cell membrane assessed as stimulation of [35S]GTPgammaS binding incubated for 60 mins by liquid scintillation spectroscopy	2020	Journal of medicinal chemistry, 12-24, Volume: 63, Issue:24	Modulation of the G-Protein-Coupled Receptor 84 (GPR84) by Agonists and Antagonists.
AID977599	Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	2013	Molecular pharmacology, Jun, Volume: 83, Issue:6	Structure-based identification of OATP1B1/3 inhibitors.
AID581853	Antimicrobial activity against drug-resistant Leishmania donovani LdDR50 assessed as inhibition of parasite growth at up to 50 uM after 24 hrs by MTT assay	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3'-diindolylmethane.
AID540299	A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis	2010	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21	Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519	A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities	2011	Antiviral research, Sep, Volume: 91, Issue:3	High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID1159550	Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening	2015	Nature cell biology, Nov, Volume: 17, Issue:11	6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	5 (1.25)	18.7374
1990's	12 (3.01)	18.2507
2000's	110 (27.57)	29.6817
2010's	224 (56.14)	24.3611
2020's	48 (12.03)	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	16 (3.91%)	5.53%
Reviews	23 (5.62%)	6.00%
Case Studies	4 (0.98%)	4.05%
Observational	0 (0.00%)	0.25%
Other	366 (89.49%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Trial	Phase	Enrollment	Study Type	Start Date	Status
A Single-Blind, Placebo-Controlled Study to Evaluate the Safety, Tolerability, and Pharmacodynamics of 3,3'-Diindolylmethane (BR-DIM) in Patients With Systemic Lupus Erythematosus (SLE) [NCT02483624]	Phase 1	6 participants (Actual)	Interventional	2016-01-31	Terminated
A Nutritional Intervention to Decrease Breast Density Among Female BRCA Carriers -A Prospective Clinical Trial [NCT02197000]		23 participants (Actual)	Interventional	2014-11-11	Completed
Phase II Trial of B-DIM (DIM: 3,3 Diindolylmethane) on Intermediate Endpoint Biomarkers in Patients With Prostate Cancer Who Are Undergoing Prostatectomy [NCT00888654]	Phase 2	41 participants (Actual)	Interventional	2009-08-31	Completed
Evaluation of Diindolylmethane Supplementation to Modulate Tamoxifen Efficacy in Breast Cancer The Diindolylmethane Efficacy Study [NCT01391689]		144 participants (Actual)	Interventional	2011-02-28	Completed
Phase I Ascending Single Dose Pharmacokinetics (PK) and Safety Study of 3,3' Di-indolylmethane (DIM) [NCT00784394]	Phase 1	20 participants (Actual)	Interventional	2004-04-30	Completed
The Potential for Oral DIM Supplementation to Increase the Production of the BRCA1 Protein in BRCA1 Mutation Carriers [NCT01022333]	Phase 1	300 participants (Anticipated)	Interventional	2009-07-31	Recruiting
The Effect of Food Supplements on Food Intake and Gut Hormone Levels [NCT04292236]		20 participants (Actual)	Interventional	2019-02-22	Completed
An Investigation Into the Effects of Diidolylmethane (BioResponse DIM®) Supplementation in Women With Low-Grade Cervical Cytological Abnormalities [CRISP-1] [NCT00462813]	Phase 3	3,000 participants (Anticipated)	Interventional	2004-10-31	Completed
Phase Ib Placebo-Controlled Trial of Diindolylmethane (BR-DIM) in the Study of the Modulation of Intermediate Endpoint Markers in Patients With Prostate Cancer Who Are Undergoing Prostatectomy [NCT00450229]	Phase 1	45 participants (Actual)	Interventional	2007-02-28	Completed
Phase 1 Multiple-Dose Safety, Pharmacokinetic, and Drug Interaction Clinical Study of Nutritional-Grade, Absorption-Enhanced DIM (BR-DIM) [NCT00392652]	Phase 1	14 participants (Actual)	Interventional	2006-11-30	Completed
Targeting FMO-Mediated TMAO Formation in Kidney Disease (TMAO) Study [NCT03152097]		13 participants (Actual)	Interventional	2018-03-30	Completed
Voice Preserving Therapy of Laryngeal Papilloma In Children [NCT00591305]		1 participants (Actual)	Interventional	2007-09-30	Terminated(stopped due to insufficient resource for recruitment)
Phase I Study of Bioresponse-dim in Non-Metastatic, Hormone-Refractory Prostate Cancer Patients With Rising Serum PSA [NCT00305747]	Phase 1	12 participants (Actual)	Interventional	2005-08-31	Completed
Diindolymethane: Anti-proliferation Agent in Thyroid Disease-Non-surgical Protocol [NCT01846364]	Early Phase 1	7 participants (Actual)	Interventional	2006-11-30	Terminated(stopped due to Lack of sufficient enrollment)
A Pilot Study of BR-DIM in Women With Stage II-III, Triple Negative, and Androgen Receptor Positive, Invasive Breast Cancer, Who Have Residual Disease Following Surgical Resection After Neoadjuvant Chemotherapy [NCT01612910]	Phase 2	0 participants (Actual)	Interventional	2012-06-30	Withdrawn(stopped due to Research cancelled.)
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial	Outcome
NCT00591305 (3) [back to overview]	Estradiol Level in Blood Post Treatment
NCT00591305 (3) [back to overview]	Estradiol Level in Blood Pre Treatment
NCT00591305 (3) [back to overview]	Number of Cases With Recurrence of Laryngeal Papilloma in 5 Months
NCT00888654 (3) [back to overview]	Mean Level of Diindolylmethane in Prostate Tissue After Treatment
NCT00888654 (3) [back to overview]	Levels of Androgen Receptor in Prostate Tissue
NCT00888654 (3) [back to overview]	Serum Levels of PSA, Testosterone, and Diindolylmethane

Intervention	pg/ml (Number)
Intervention	29

Intervention	pg/ml (Number)
Intervention	20

Intervention	case (Number)
Intervention	1

Intervention	ng/g (Mean)
B-Dim, Radical Prosatectomy	14.2

Intervention	AR score (intensity x % cells stained) (Mean)
	Pre-BR-DIM Androgen Receptor	Post-BR-DIM Androgen Receptor
B-Dim, Radical Prosatectomy	278	245

Intervention	ng/ml (Median)
	Pre-treatment PSA	Post-treatment PSA	Pre-treatment Testosterone	Post-treatment Testosterone	Pre-treatment DIM	Post-treatment DIM
B-Dim, Radical Prosatectomy	6.4	5.8	301	388	0.0	7.5

Substance	Relationship Strength	Studies	Trials	Classes	Roles
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	7.6	1	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
aminooxyacetic acid Aminooxyacetic Acid: A compound that inhibits aminobutyrate aminotransferase activity in vivo, thereby raising the level of gamma-aminobutyric acid in tissues.. (aminooxy)acetic acid : A member of the class of hydroxylamines that is acetic acid substituted at postion 2 by an aminooxy group. It is a compound which inhibits aminobutyrate aminotransferase activity in vivo, resulting in increased levels of gamma-aminobutyric acid in tissues.	2.25	1	0	amino acid; hydroxylamines; monocarboxylic acid	anticonvulsant; EC 2.6.1.19 (4-aminobutyrate--2-oxoglutarate transaminase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; nootropic agent
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	7.68	3	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
choline [no description available]	2.1	1	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae 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.	2.25	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	7.25	1	0	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
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
cytosine [no description available]	3.12	1	0	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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.	2.6	1	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
1,4-dihydroxy-2-naphthoic acid [no description available]	7.41	1	0	dihydroxy monocarboxylic acid; naphthalenediols; naphthohydroquinone; naphthoic acid	Escherichia coli metabolite
glycine [no description available]	2.25	1	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
indole [no description available]	3.64	2	0	indole; polycyclic heteroarene	Escherichia coli metabolite
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	2.46	2	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	2.11	1	0	diatomic iodine	nutrient
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.31	1	0	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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
n,n-dimethylaniline N,N-dimethylaniline: RN given refers to parent cpd; structure. dimethylaniline : A methylaniline carrying at least two methyl groups.. N,N-dimethylaniline : A tertiary amine that is aniline in which the amino hydrogens are replaced by two methyl groups.	2	1	0	dimethylaniline; tertiary amine
trimethyloxamine trimethyloxamine: used in manufacture of quaternary ammonium cpds; insect attractant; warming agent for gas; oxidant; structure. trimethylamine N-oxide : A tertiary amine oxide resulting from the oxidation of the amino group of trimethylamine.	2.21	1	0	tertiary amine oxide	Escherichia coli metabolite; metabolite; osmolyte
epibatidine [no description available]	2.07	1	0	alkaloid
mandelic acid SAMMA: mandelic acid condensation polymer	2.08	1	0	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine: A dopaminergic neurotoxic compound which produces irreversible clinical, chemical, and pathological alterations that mimic those found in Parkinson disease.. 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine : A tetrahydropyridine that is 1,2,3,6-tetrahydropyridine substituted by a methyl group at position 1 and a phenyl group at position 4.	2.05	1	0	methylpyridines; phenylpyridine; tetrahydropyridine	neurotoxin
alpha-hydroxymyristic acid 2-hydroxymyristic acid : A long-chain fatty acid that is a derivative of myristic acid having a hydroxy substituent at C-2.	2.25	1	0	2-hydroxy fatty acid; long-chain fatty acid
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	2.03	1	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
phenytoin [no description available]	2.02	1	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
aristolochic acid i aristolochic acid I: phospholipase A inhibitor. aristolochic acid A : An aristolochic acid that is phenanthrene-1-carboxylic acid that is substituted by a methylenedioxy group at the 3,4 positions, by a methoxy group at position 8, and by a nitro group at position 10. It is the most abundant of the aristolochic acids and is found in almost all Aristolochia (birthworts or pipevines) species. It has been tried in a number of treatments for inflammatory disorders, mainly in Chinese and folk medicine. However, there is concern over their use as aristolochic acid is both carcinogenic and nephrotoxic.	2.07	1	0	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	2.13	1	0	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	6.44	4	1	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
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.	7.48	2	0	5-methoxyfurocoumarin; organic heterotricyclic compound; psoralens	hepatoprotective agent; plant metabolite
beta-naphthoflavone beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.	4.22	5	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
2,5-di-tert-butylhydroquinone 2,5-di-tert-butylbenzene-1,4-diol : A member of the class of hydroquinones that is benzene-1,4-diol substituted by tert-butyl groups at position 2 and 5.	2.06	1	0	hydroquinones
bicalutamide bicalutamide: approved for treatment of advanced prostate cancer. N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide : A member of the class of (trifluoromethyl)benzenes that is 4-amino-2-(trifluoromethyl)benzonitrile in which one of the amino hydrogens is substituted by a 3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanoyl group.. bicalutamide : A racemate comprising of equal amounts of (R)-bicalutamide and (S)-bicalutamide. It is an oral non-steroidal antiandrogen used in the treatment of prostate cancer and hirsutism.	2.01	1	0	(trifluoromethyl)benzenes; monocarboxylic acid amide; monofluorobenzenes; nitrile; sulfone; tertiary alcohol
cacodylic acid dimethylarsinic acid : The organoarsenic compound that is arsenic acid substituted on the central arsenic atom with two methyl groups.	2.13	1	0	organoarsenic compound	xenobiotic 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.	2.31	1	0	aromatic ether; nitrile; polyether; tertiary amino compound
carmustine Carmustine: A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed). carmustine : A member of the class of N-nitrosoureas that is 1,3-bis(2-chloroethyl)urea in which one of the nitrogens is substituted by a nitroso group.	2.11	1	0	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent
celecoxib [no description available]	2.04	1	0	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	2.07	1	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	1.94	1	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic 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.	2.59	2	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
econazole Econazole: An imidazole derivative that is commonly used as a topical antifungal agent.. econazole : A racemate composed of equimolar amounts of (R)- and (S)-econazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections.. 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 4-chlorobenzyl group.	2.06	1	0	dichlorobenzene; ether; imidazoles; monochlorobenzenes
ellipticine ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.	2.07	1	0	indole alkaloid; organic heterotetracyclic compound; organonitrogen heterocyclic compound; polycyclic heteroarene	antineoplastic agent; plant metabolite
embelin embelin: from Embelia fruit (Myrsinaceae). embelin : A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, antineoplastic and inhibitory activity towards hepatitis C protease.	2.53	2	0	dihydroxy-1,4-benzoquinones	antimicrobial agent; antineoplastic agent; hepatitis C protease inhibitor; plant metabolite
emodin Emodin: Purgative anthraquinone found in several plants, especially RHAMNUS PURSHIANA. It was formerly used as a laxative, but is now used mainly as a tool in toxicity studies.. emodin : A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs.	2.07	1	0	trihydroxyanthraquinone	antineoplastic agent; laxative; plant metabolite; tyrosine kinase inhibitor
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
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.	11.79	71	2	indolyl alcohol	antineoplastic agent; plant metabolite
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
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
lapachol lapachol : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae.	3.21	1	0
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.	2.66	2	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	2.76	3	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
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	2.13	1	0	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
methoxsalen Methoxsalen: A naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA ADDUCTS in the presence of ultraviolet A irradiation.. methoxsalen : A member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis.	2.48	2	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
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2.06	1	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
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'.	2.02	1	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
phloretin [no description available]	2.07	1	0	dihydrochalcones	antineoplastic agent; plant metabolite
rofecoxib [no description available]	3.25	1	0	butenolide; sulfone	analgesic; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
safrole Safrole: A member of the BENZODIOXOLES that is a constituent of several VOLATILE OILS, notably SASSAFRAS oil. It is a precursor in the synthesis of the insecticide PIPERONYL BUTOXIDE and the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA).. safrole : A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sassafras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.	1.98	1	0	benzodioxoles	flavouring agent; insecticide; metabolite; plant metabolite
sanguinarine benzophenanthridine alkaloid : A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.	2.07	1	0	alkaloid antibiotic; benzophenanthridine alkaloid; botanical anti-fungal agent
streptonigrin [no description available]	2.07	1	0	pyridines; quinolone	antimicrobial agent; antineoplastic agent
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	4.34	7	0	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
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
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
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
estriol hormonin: estrogen replacement; each tablet contains 600 ug micronized 17beta-estradiol, 270 ug estriol and 1.4 mg estrone. chlorapatite : A phosphate mineral with the formula Ca5(PO4)3Cl.	4.32	1	1	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-hydroxy steroid	estrogen; human metabolite; human xenobiotic metabolite; mouse metabolite
reserpine Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.. reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.	2.07	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
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	2.13	1	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	6.1	3	2	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
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.	2.41	1	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.	3.61	2	0	cyclic dicarboxylic anhydride; monoterpenoid	EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; herbicide
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.06	1	0	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	2.02	1	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
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.	2.7	3	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.	2.07	1	0	kanamycins	bacterial metabolite
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
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	2.02	1	0	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
androstenedione Androstenedione: A delta-4 C19 steroid that is produced not only in the TESTIS, but also in the OVARY and the ADRENAL CORTEX. Depending on the tissue type, androstenedione can serve as a precursor to TESTOSTERONE as well as ESTRONE and ESTRADIOL.. androst-4-ene-3,17-dione : A 3-oxo Delta(4)-steroid that is androst-4-ene substituted by oxo groups at positions 3 and 17. It is a steroid hormone synthesized in the adrenal glands and gonads.	1.98	1	0	17-oxo steroid; 3-oxo-Delta(4) steroid; androstanoid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
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.	2.1	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.	2.07	1	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.	2.72	3	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
egtazic acid Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.	2.03	1	0	diether; tertiary amino compound; tetracarboxylic acid	chelator
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
isoleucine Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.	2.05	1	0	aspartate family amino acid; isoleucine; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
trifluoroethanol Trifluoroethanol: A non-aqueous co-solvent that serves as tool to study protein folding. It is also used in various pharmaceutical, chemical and engineering applications.	2.41	1	0	fluoroalcohol
gibberellic acid gibberellic acid: RN given refers to (1alpha,2beta,4aalpha,4bbeta,10beta)-isomer; structure. gibberellin A3 : A C19-gibberellin that is a pentacyclic diterpenoid responsible for promoting growth and elongation of cells in plants. Initially identified in Gibberella fujikuroi,it differs from gibberellin A1 in the presence of a double bond between C-3 and C-4.	2.07	1	0	C19-gibberellin; gibberellin monocarboxylic acid; lactone; organic heteropentacyclic compound	mouse metabolite; plant metabolite
bisphenol a 4,4'-isopropylidene diphenol: stimulates proliferative responses and cytokine productions of murine spleen cells and thymus cells in vitro. bisphenol : By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom.. bisphenol A : A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.	2.15	1	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
visnagin visnagin: from Musineon divaricatum. visnagin : A furanochromone that is furo[3,2-g]chromen-5-one which is substituted at positions 4 and 7 by methoxy and methyl groups, respectively. Found in the toothpick-plant, Ammi visnaga.	2.07	1	0	aromatic ether; furanochromone; polyketide	anti-inflammatory agent; antihypertensive agent; EC 1.1.1.37 (malate dehydrogenase) inhibitor; phytotoxin; plant metabolite; vasodilator agent
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.	2.07	1	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
propargyl alcohol propargyl alcohol: irreversibly inactivates alcohol oxidase; RN given refers to parent cpd. prop-2-yn-1-ol : A terminal acetylenic compound that is prop-2-yne substituted by a hydroxy group at position 1.	2.1	1	0	propynol; terminal acetylenic compound; volatile organic compound	antifungal agent; Saccharomyces cerevisiae metabolite
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	2.31	1	0	pyrrole; secondary amine
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.	2.25	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.	2.66	2	0	medium-chain fatty acid; straight-chain saturated fatty acid	antifungal agent; human 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
isoquinoline [no description available]	3.21	1	0	azaarene; isoquinolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
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
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	2.41	1	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
shikimic acid Shikimic Acid: A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.. shikimic acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms.	2.07	1	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; 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.	3.54	2	0	catechin	antioxidant; plant metabolite
dibenzo(a,l)pyrene dibenzo(a,l)pyrene: structure in first source	2.11	1	0	ortho- and peri-fused polycyclic arene	human metabolite; mutagen
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.	2.45	2	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	2.08	1	0	isoxazoles; 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.	2.43	2	0	pyrrolizidine alkaloid
nandrolone Nandrolone: C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of ESTRADIOL to resemble TESTOSTERONE but less one carbon at the 19 position.. nandrolone : A 3-oxo Delta(4)-steroid that is estr-4-en-3-one substituted by a beta-hydroxy group at position 17.	3.56	1	1	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; anabolic androgenic steroid	human 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
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.	2.07	1	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
hesperidin Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.07	1	0	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
dihydrotestosterone Dihydrotestosterone: A potent androgenic metabolite of TESTOSTERONE. It is produced by the action of the enzyme 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE.. 17beta-hydroxyandrostan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4-5 double bond has been reduced to a single bond with unspecified configuration at position 5.. 17beta-hydroxy-5alpha-androstan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5.	2.45	2	0	17beta-hydroxy steroid; 17beta-hydroxyandrostan-3-one; 3-oxo-5alpha-steroid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
tryptophol tryptophol : An indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2.	2.15	1	0	indolyl alcohol	auxin; plant metabolite; Saccharomyces cerevisiae metabolite
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	2.49	2	0	C-nitro compound; imidazoles	antitubercular agent
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.31	1	0	dialdehyde	biomarker
myristic acid Myristic Acid: A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). tetradecanoic acid : A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.. tetradecanoate : A long-chain fatty acid anion that is the conjugate base of myristic acid; major species at pH 7.3.	2.66	2	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite
trinitrobenzenesulfonic acid Trinitrobenzenesulfonic Acid: A reagent that is used to neutralize peptide terminal amino groups.. 2,4,6-trinitrobenzenesulfonic acid : The arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions.	2.06	1	0	arenesulfonic acid; C-nitro compound	epitope; explosive; reagent
alpha-naphthoflavone alpha-naphthoflavone: inhibits P4501A1 and P4501A2; stimulates some activities of P4503A4. alpha-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14).	3.59	2	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist; aryl hydrocarbon receptor antagonist; EC 1.14.14.14 (aromatase) inhibitor
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.	2.25	1	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
methylnitrosourea Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.	2.06	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
2-phenylindole alpha-phenylindole: RN given refers to parent cpd	2.15	1	0	phenylindole
deoxycytidine [no description available]	2.96	4	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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
beta-hydroxymyristic acid beta-hydroxymyristic acid: RN given refers to cpd without isomeric designation. 3-hydroxytetradecanoic acid : A 3-hydroxy fatty acid that is tetradecanoic (myristic) acid substituted at position 3 by a hydroxy group	2.25	1	0	3-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; long-chain fatty acid	bacterial metabolite; human metabolite
phenethyl isothiocyanate phenethyl isothiocyanate: a dietary liver aldehyde dehydrogenase inhibitor; promotes urinary bladder carcinoma. phenethyl isothiocyanate : An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.	2.43	2	0	isothiocyanate	antineoplastic agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; metabolite
muscarine [no description available]	2.07	1	0
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
butylhydroxybutylnitrosamine Butylhydroxybutylnitrosamine: A substituted carcinogenic nitrosamine.. N-butyl-N-(4-hydroxybutyl)nitrosamine : A nitrosamine that has butyl and 4-hydroxybutyl substituents. In mice, it causes high-grade, invasive cancers in the urinary bladder, but not in any other tissues.	2.53	2	0	nitrosamine; primary alcohol	carcinogenic agent
n-methylaspartate N-Methylaspartate: An amino acid that, as the D-isomer, is the defining agonist for the NMDA receptor subtype of glutamate receptors (RECEPTORS, NMDA).. N-methyl-D-aspartic acid : An aspartic acid derivative having an N-methyl substituent and D-configuration.	2.25	1	0	amino dicarboxylic acid; D-alpha-amino acid; D-aspartic acid derivative; secondary amino compound	neurotransmitter agent
propargyl ether propargyl ether: structure in first source	2.08	1	0
n-deacetyl-n-formylcolchicine N-deacetyl-N-formylcolchicine: structure given in first source	2.07	1	0	cyclic ketone
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.08	1	0	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	2.08	1	0	elemental platinum; nickel group element atom; platinum group metal atom
scandium Scandium: An element of the rare earth family of metals. It has the atomic symbol Sc, atomic number 21, and atomic weight 45.	2.17	1	0	d-block element atom; rare earth metal atom; scandium group element atom
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	2.41	1	0	cadmium molecular entity; zinc group element atom
vanadium Vanadium: A metallic element with the atomic symbol V, atomic number 23, and atomic weight 50.94. It is used in the manufacture of vanadium steel. Prolonged exposure can lead to chronic intoxication caused by absorption usually via the lungs.	2.66	2	0	elemental vanadium; vanadium group element atom	micronutrient
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	2.11	1	0	D-galactosamine; primary amino compound	toxin
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	3.9	3	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
myrmicacin myrmicacin: found in secretions of South American leaf-cutting ant; inhibitor for mitotic progression after metaphase. 3-hydroxydecanoic acid : A medium-chain fatty acid that is decanoic acid substituted at position 3 by a hydroxy group.	2.25	1	0	3-hydroxy fatty acid; medium-chain fatty acid	antimitotic; Escherichia coli metabolite
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.47	2	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
iodine [no description available]	2.11	1	0	halide anion; monoatomic iodine	human metabolite
2-bromoergocryptine mesylate [no description available]	2.07	1	0	methanesulfonate salt	antiparkinson drug
zingerone zingerone: pungent principle of ginger; structure. zingerone : A methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.	2.07	1	0	methyl ketone; monomethoxybenzene; phenols	anti-inflammatory agent; antiemetic; antioxidant; flavouring agent; fragrance; plant metabolite; radiation protective agent
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.1	1	0	benzenes; phenyl acetates
azoxymethane Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.	2.05	1	0
nigericin Nigericin: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. (From Merck Index, 11th ed). nigericin : A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.	2.08	1	0	polycyclic ether	antibacterial agent; antimicrobial agent; bacterial metabolite; potassium ionophore
3,4,3',4'-tetrachlorobiphenyl 3,4,3',4'-tetrachlorobiphenyl: RN given refers to parent cpd. 3,3',4,4'-tetrachlorobiphenyl : A tetrachlorobiphenyl that is biphenyl in which the hydrogens at position 3 and 4 on each phenyl group are replaced by chlorines.	2.03	1	0	dichlorobenzene; tetrachlorobiphenyl
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	3.01	4	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
etoposide [no description available]	2.75	3	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
1,2,7,8-tetrachlorodibenzo-p-dioxin 1,2,7,8-tetrachlorodibenzo-p-dioxin: structure in first source	2.05	1	0
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
chlorodiphenyl (54% chlorine) Chlorodiphenyl (54% Chlorine): A mixture of polychlorinated biphenyls that induces hepatic microsomal UDP-glucuronyl transferase activity towards thyroxine.. Aroclor 1254 : A mixture of polychlorobiphenyls of unspecified composition, containing 54% chlorine (X = Cl or H).	1.99	1	0
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
idarubicin Idarubicin: An orally administered anthracycline antineoplastic. The compound has shown activity against BREAST NEOPLASMS; LYMPHOMA; and LEUKEMIA.	7.04	1	0	anthracycline antibiotic; deoxy hexoside; monosaccharide derivative
4-(n-methyl-n-nitrosamino)-1-(3-pyridyl)-1-butanone 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone: structure; from tobacco smoke	4.52	2	0	nitrosamine; pyridines
colforsin Colforsin: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant COLEUS FORSKOHLII. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.	2.07	1	0	acetate ester; cyclic ketone; labdane diterpenoid; organic heterotricyclic compound; tertiary alpha-hydroxy ketone; triol	adenylate cyclase agonist; anti-HIV agent; antihypertensive agent; plant metabolite; platelet aggregation inhibitor; protein kinase A agonist
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
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
fura-2 Fura-2: A fluorescent calcium chelating agent which is used to study intracellular calcium in tissues.	2.76	3	0
imiquimod Imiquimod: A topically-applied aminoquinoline immune modulator that induces interferon production. It is used in the treatment of external genital and perianal warts, superficial CARCINOMA, BASAL CELL; and ACTINIC KERATOSIS.. imiquimod : An imidazoquinoline fused [4,5-c] carrying isobutyl and amino substituents at N-1 and C-4 respectively. A prescription medication, it acts as an immune response modifier and is used to treat genital warts, superficial basal cell carcinoma, and actinic keratosis.	2.41	1	0	imidazoquinoline	antineoplastic agent; interferon inducer
cidofovir anhydrous Cidofovir: An acyclic nucleoside phosphonate that acts as a competitive inhibitor of viral DNA polymerases. It is used in the treatment of RETINITIS caused by CYTOMEGALOVIRUS INFECTIONS and may also be useful for treating HERPESVIRUS INFECTIONS.. cidofovir anhydrous : Cytosine substituted at the 1 position by a 3-hydroxy-2-(phosphonomethoxy)propyl group (S configuration). A nucleoside analogue, it is an injectable antiviral used for the treatment of cytomegalovirus (CMV) retinitis in AIDS patients.	3.12	1	0	phosphonic acids; pyrimidone	anti-HIV agent; antineoplastic agent; antiviral drug; photosensitizing agent
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.	2.96	4	0	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
3,4,5,3',4'-pentachlorobiphenyl 3,3',4,4',5-pentachlorobiphenyl : A pentachlorobiphenyl in which the chlorines are located at the 3, 4, 5, 3', and 4' positions.	2.21	1	0	pentachlorobiphenyl; trichlorobenzene
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	2.21	1	0	D-glucopyranose	epitope; mouse metabolite
mevastatin mevastatin: antifungal metabolite from Penicillium brevicopactum; potent inhibitory activity to sterol synthesis; structure. mevastatin : A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals.	2.07	1	0	2-pyranones; carboxylic ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	antifungal agent; apoptosis inducer; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; fungal metabolite; Penicillium metabolite
ursolic acid [no description available]	2.07	1	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
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.	3.84	3	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
2,2'-dithiodiethanesulfonic acid [no description available]	1.93	1	0
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
dienogest [no description available]	8.56	1	1	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; aliphatic nitrile; steroid hormone	progesterone receptor agonist; progestin; synthetic oral contraceptive
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.	2.07	1	0	catechin; polyphenol	antioxidant
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]	2.07	1	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
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
12-hydroxydodecanoic acid 12-hydroxylauric acid : A medium-chain fatty acid that is the 12-hydroxylated derivative of lauric acid.	2.25	1	0	omega-hydroxy-medium-chain fatty acid	human metabolite
eriocitrin eriocitrin: structure in first source. eriocitrin : A disaccharide derivative that consists of eriodictyol substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.07	1	0	3'-hydroxyflavanones; 4'-hydroxyflavanones; disaccharide derivative; flavanone glycoside; rutinoside; trihydroxyflavanone	antioxidant
chloramphenicol 3-acetate chloramphenicol 3-acetate: inactive metabolite of chloramphenicol	2.02	1	0	acetate ester
cyprodinil cyprodinil: structure in first source. cyprodinil : A member of the class of aminopyrimidine that is N-phenylpyrimidin-2-amine carrying additional cyclopropyl and methyl substituents at positions 4 and 6 respectively. A broad spectrum fungicide used to control a range of pathogens including Tapesia yallundae, Botrytis spp., Alternaria spp. and Rhynchospium secalis. Whilst it is a recognised irritant no serious human health concerns have been identified. It is moderately toxic to birds as well as most aquatic organisms and earthworms, but it is not considered toxic to honeybees.	7.17	1	0	aminopyrimidine; anilinopyrimidine fungicide; cyclopropanes; secondary amino compound	antifungal agrochemical; aryl hydrocarbon receptor agonist; environmental contaminant; xenobiotic
7,8-dihydromethysticin [no description available]	2.07	1	0	2-pyranones; aromatic ether
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	7.75	3	0	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
cinchonine [no description available]	2.07	1	0	(8xi)-cinchonan-9-ol; cinchona alkaloid	metabolite
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
3-hydroxydodecanoic acid 3-hydroxydodecanoic acid: RN given refers to cpd without isomeric designation. 3-hydroxylauric acid : A medium-chain fatty acid that is the 3-hydroxylated derivative of lauric acid; associated with fatty acid metabolic disorders.	2.66	2	0	3-hydroxy fatty acid; medium-chain fatty acid
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
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	2.08	1	0	D-glucuronic acid	algal metabolite
10-hydroxycamptothecin [no description available]	2.07	1	0	pyranoindolizinoquinoline
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
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	2.11	1	0	cobalt group element atom; metal allergen	micronutrient
fulvestrant Fulvestrant: An estradiol derivative and estrogen receptor antagonist that is used for the treatment of estrogen receptor-positive, locally advanced or metastatic breast cancer.. fulvestrant : A 3-hydroxy steroid that is 17beta-estradiol in which the 7alpha hydrogen has been replaced by a nonyl group in which one of the hydrogens of the terminal methyl has been replaced by a (4,4,5,5,5-pentafluoropentyl)sulfinyl group. An estrogen receptor antagonist, it is used in the treatment of breast cancer.	2.44	2	0	17beta-hydroxy steroid; 3-hydroxy steroid; organofluorine compound; sulfoxide	antineoplastic agent; estrogen antagonist; estrogen receptor antagonist
1,2-bis(2-aminophenoxy)ethane-n,n,n',n'-tetraacetic acid 1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid: structure in first source	2.03	1	0	polyamino carboxylic acid; tetracarboxylic acid	chelator
1-(2-(3-(4-methoxyphenyl)propoxy)-4-methoxyphenylethyl)-1h-imidazole 1-(2-(3-(4-methoxyphenyl)propoxy)-4-methoxyphenylethyl)-1H-imidazole: inhibits platelet aggregation & Ca2+ entry into platelets. SKF-96365 free base : An ether that is 2-(1H-imidazol-1-yl)-1-(4-methoxyphenyl)ethanol in which the hydrogen of the hydroxy group has been substituted by a 3-(4-methoxyphenyl)propyl group.	2.06	1	0	ether; imidazoles; monomethoxybenzene	TRP channel blocker
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
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
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	2.02	1	0
homoorientin homoorientin: isolated from Swertia japonica; structure given in first source	2.07	1	0	flavone C-glycoside; tetrahydroxyflavone	antineoplastic agent; radical scavenger
16-hydroxyestrone 16-hydroxyestrone: has implications in estrogen physiology & pathophysiology; RN given refers to parent cpd; structure in Negwer, 5th ed, #3670	4.84	2	1
6-methyl-1,3,8-trichlorodibenzofuran 6-methyl-1,3,8-trichlorodibenzofuran: structure given in first source	3.59	2	0
tanshinone tanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agent	2.11	1	0	abietane diterpenoid	anticoronaviral agent
ponasterone a ponasterone A: RN given refers to (2 beta,3 beta,5 beta,22R)-isomer	2.05	1	0	14alpha-hydroxy steroid; 20-hydroxy steroid; 22-hydroxy steroid; 2beta-hydroxy steroid; 3beta-hydroxy steroid; 6-oxo steroid; phytoecdysteroid
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
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
5,6,11,12,17,18-hexahydrocyclononatriindole 5,6,11,12,17,18-hexahydrocyclononatriindole: structure given in first source; occurs in edible cruciferous vegetables	2.67	3	0
methotrexate [no description available]	2.25	1	0	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
delphinidin delphinidin: RN given refers to parent cpd;. delphinidin : An anthocyanidin cation consisting of benzopyrylium with hydroxy substituents at the 3-, 5- and 7-positions and a 3,4,5-trihydroxyphenyl group at the 2-position. It is a plant pigment responsible for the colours of the plants of the genera Viola and Delphinium.	2.11	1	0	5-hydroxyanthocyanidin	antineoplastic agent; biological pigment; plant 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
docetaxel anhydrous Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.	2.99	4	0	secondary alpha-hydroxy ketone; tetracyclic diterpenoid	antimalarial; antineoplastic agent; photosensitizing agent
centchroman Centchroman: A non-steroidal anti-fertility agent with anti-hormonal properties.	2.82	2	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.	2.31	1	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
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
kynurenine L-kynurenine : A kynurenine that has L configuration.	3.35	1	0	amino acid zwitterion; kynurenine; non-proteinogenic L-alpha-amino acid	human metabolite; mouse metabolite; Saccharomyces cerevisiae 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
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	2.11	1	0	amino acid zwitterion; angiotensin II	human metabolite
erlotinib hydrochloride [no description available]	2.45	2	0	hydrochloride; terminal acetylenic compound	antineoplastic agent; protein kinase inhibitor
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	3.12	1	0	divalent inorganic anion; phosphite ion
limonin [no description available]	2.07	1	0	epoxide; furans; hexacyclic triterpenoid; lactone; limonoid; organic heterohexacyclic compound	inhibitor; metabolite; volatile oil component
propargylglycine propargylglycine: RN given refers to cpd without isomeric designation; structure	2.25	1	0
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	3.1	5	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
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
n-nitroso-tris-chloroethylurea N-nitroso-tris-chloroethylurea: induces dysplasia and premalignant lesions	2.11	1	0
troleandomycin Troleandomycin: A macrolide antibiotic that is similar to ERYTHROMYCIN.. troleandomycin : A semi-synthetic macrolide antibiotic obtained by acetylation of the three free hydroxy groups of oleandomycin. Troleandomycin is only found in individuals that have taken the drug.	2.07	1	0	acetate ester; epoxide; macrolide antibiotic; monosaccharide derivative; polyketide; semisynthetic derivative	EC 1.14.13.97 (taurochenodeoxycholate 6alpha-hydroxylase) inhibitor; xenobiotic
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
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.03	1	0
lupeol [no description available]	2.53	2	0	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory drug; plant metabolite
metribolone Metribolone: A synthetic non-aromatizable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.. 17beta-hydroxy-17-methylestra-4,9,11-trien-3-one : A synthetic non-aromatisable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.	2.01	1	0	17beta-hydroxy steroid; 3-oxo steroid; anabolic androgenic steroid	androgen
acetylstrophanthidin acetylstrophanthidin: structure. acetylstrophanthidin : An acetate ester that is strophanidin acetylated at the 3beta-hydroxy group.	2.07	1	0	acetate ester	anti-arrhythmia drug
3',4'-dimethoxy-alpha-naphthoflavone 3',4'-dimethoxy-alpha-naphthoflavone: activated Ah receptor; structure in first source	3.35	1	0
Harringtonine harringtonin: alkaloid C from Caphalotaxus fortunei	2.07	1	0	alkaloid
acivicin [no description available]	2.48	2	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
indole-3-acetonitrile indole-3-acetonitrile: occurs in edible cruciferous vegetables. indole-3-acetonitrile : A nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a 1H-indol-3-yl group.	3.11	5	0	indoles; nitrile	auxin; human xenobiotic metabolite; plant hormone; plant metabolite
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
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.	2.1	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
mimosine L-mimosine : An L-alpha-amino acid that is propionic acid substituted by an amino group at position 2 and a 3-hydroxy-4-oxopyridin-1(4H)-yl group at position 3 (the 2S-stereoisomer). It a non-protein plant amino acid isolated from Mimosa pudica.	2.07	1	0	4-pyridones; amino acid zwitterion; non-proteinogenic L-alpha-amino acid	EC 1.14.18.1 (tyrosinase) inhibitor; plant metabolite
2-hydroxyestrone 2-hydroxyestrone: catechol estrogen which is a major metabolite of estradiol in man & animals; RN given refers to parent cpd. 2-hydroxyestrone : A 2-hydroxy steroid that is estrone substituted by a hydroxy group at position 2.	6.1	3	2	2-hydroxy steroid; catechols	human metabolite
eriodictyol eriodictyol: structure. eriodictyol : A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' respectively.	2.07	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
monensin Monensin: An antiprotozoal agent produced by Streptomyces cinnamonensis. It exerts its effect during the development of first-generation trophozoites into first-generation schizonts within the intestinal epithelial cells. It does not interfere with hosts' development of acquired immunity to the majority of coccidial species. Monensin is a sodium and proton selective ionophore and is widely used as such in biochemical studies.. monensin A : A spiroketal, monensin A is the major component of monensin, a mixture of antibiotic substances produced by Streptomyces cinnamonensis. An antiprotozoal, it is used as the sodium salt as a feed additive for the prevention of coccidiosis in poultry and as a growth promoter in cattle.	2.08	1	0	cyclic hemiketal; monocarboxylic acid; polyether antibiotic; spiroketal	antifungal agent; coccidiostat; ionophore
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]	2.07	1	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.	2.07	1	0	beta-hydroxy ketone; guaiacols	antineoplastic agent; plant metabolite
securinine securinine: a quinolizine pseudoalkaloid (not from amino acid) from Securinega suffurutiosa or Securinini nitras	2.07	1	0	indolizines
Dubinidine [no description available]	2.07	1	0	organic heterotricyclic compound; organonitrogen heterocyclic compound; oxacycle
cyclopamine [no description available]	2.48	2	0	piperidines	glioma-associated oncogene inhibitor
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
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	2.07	1	0	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	5.2	8	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	2.07	1	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.	3.14	5	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.	2.48	2	0	2-benzofurans; gamma-lactone; monocarboxylic acid; phenols	anticoronaviral agent; antimicrobial agent; antineoplastic agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; environmental contaminant; immunosuppressive agent; mycotoxin; Penicillium metabolite; xenobiotic
prostaglandin d2 Prostaglandin D2: The principal cyclooxygenase metabolite of arachidonic acid. It is released upon activation of mast cells and is also synthesized by alveolar macrophages. Among its many biological actions, the most important are its bronchoconstrictor, platelet-activating-factor-inhibitory, and cytotoxic effects.. prostaglandin D2 : A member of the class of prostaglandins D that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,9alpha,13E,15S- stereoisomer).	2.02	1	0	prostaglandins D	human metabolite; mouse 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
h 89 N-(2-(4-bromocinnamylamino)ethyl)-5-isoquinolinesulfonamide: structure given in first source. N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A member of the class of isoquinolines that is the sulfonamide obtained by formal condensation of the sulfo group of isoquinoline-5-sulfonic acid with the primary amino group of N(1)-[3-(4-bromophenyl)prop-2-en-1-yl]ethane-1,2-diamine. It is a protein kinase A inhibitor.. (E)-N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide in which the double bond adopts a trans-configuration.	2.02	1	0	N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide
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
8-prenylnaringenin 8-prenylnaringenin: a phytogenic antineoplastic agent; structure in first source. sophoraflavanone B : A trihydroxyflavanone that is (S)-naringenin having a prenyl group at position 8.	2.02	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; trihydroxyflavanone	plant metabolite; platelet aggregation inhibitor
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
sinapinic acid sinapinic acid: a matrix for matrix-assisted laser desorption technique for protein MW determination; a constituent of propolis. trans-sinapic acid : A sinapic acid in which the double bond has trans-configuration.	2.6	1	0	sinapic acid	MALDI matrix material; plant metabolite
isosafrole isosafrole: RN given refers to cpd without isomeric designation	1.98	1	0	benzodioxoles
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.	2.07	1	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.	4.77	5	0	stilbene
xanthohumol xanthohumol: from hop plant, Humulus lupulus. xanthohumol : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells.	2.05	1	0	aromatic ether; chalcones; polyphenol	anti-HIV-1 agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor; metabolite
rauwolscine Rauwolscine: A stereoisomer of yohimbine.	2.07	1	0	methyl 17-hydroxy-20xi-yohimban-16-carboxylate
glucobrassicin glucobrassicin: isolated from Brussels sprouts; structure given in first source. glucobrassicin : An indolylmethylglucosinolic acid that is 1-thio-beta-D-glucopyranose having a 2-(1H-indol-3-yl)-N-(sulfooxy)ethanimidoyl group attached to the anomeric sulfur.	12.17	5	2	indolyl carbohydrate; indolylmethylglucosinolic acid
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
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.	2.07	1	0	caffeic acid	geroprotector; mouse 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.	2.52	2	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.	10.39	7	0	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.	7.11	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.	7.49	2	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
aurapten aurapten: RN refers to (E)-isomer; structure given in first source. auraptene : A member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group. Ii is isolated from several edible fruits and vegetables and exhibits a variety of therapeutic properties.	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
oxazolone Oxazolone: Immunologic adjuvant and sensitizing agent.	7.08	1	0
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.	2.07	1	0	cinnamate ester; tannin	food component; plant metabolite
thiosemicarbazide thiosemicarbazide: glutamate decarboxylase antagonist; structure given in first source. hydrazinecarbothioamide : A member of the class of thioureas that is thiourea in which a hydrogen of one of the amino groups is replaced by an amino group.	2.17	1	0	hydrazines; thiocarboxamide; thioureas
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	2.08	1	0	thiocarboxamide	hepatotoxic 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]	10.44	5	1	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
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
toremifene Toremifene: A first generation selective estrogen receptor modulator (SERM). Like TAMOXIFEN, it is an estrogen agonist for bone tissue and cholesterol metabolism but is antagonistic on mammary and uterine tissue.	2	1	0	aromatic ether; organochlorine compound; tertiary amine	antineoplastic agent; bone density conservation agent; estrogen antagonist; estrogen receptor modulator
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
cobaltous chloride cobaltous chloride: RN given refers to unlabeled cpd; RN in Chemline for cobalt trichloride: 10241-04-0; RN for 60-labeled cpd: 14543-09-0; RN for 57-labeled cpd: 164113-89-1; RN for 58-labeled cpd: 29377-09-1; structure. cobalt dichloride : A cobalt salt in which the cobalt metal is in the +2 oxidation state and the counter-anion is chloride. It is used as an indicator for water in desiccants.	2.11	1	0	cobalt salt; inorganic chloride	allergen; calcium channel blocker; sensitiser; two-colour indicator
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
ascorbigen ascorbigen: a depot form of ascorbic acid. ascorbigen : An indolyl carbohydrate that consists of (3aS,6S,6aR)-3,3a,6-trihydroxy-3-tetrahydrofuro[3,2-b]furan-2-one in which position 3 is substituted by an indol-3-ylmethyl group. Formed from indole-3-carbinol and ascorbic acid in brassica vegetables.	2.77	3	0	indolyl carbohydrate	metabolite
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
mtt formazan MTT formazan: a blue MEM-insoluble mitochondrial byproduct; used to determine viability of cells with active mitochondrial dehydrogenase enzymes	2	1	0
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	3.21	1	0
5,6-dehydrokawain 5,6-dehydrokawain: from Alpinia speciosa rhizoma; RN given for cpd without isomeric designation; structure given in first source	2.07	1	0	2-pyranones; aromatic ether
9,10-dihydrolysergol 9,10-dihydrolysergol: RN given refers to cpd without isomeric designation	2.07	1	0
geranylgeranic acid geranylgeranic acid: RN given refers to cpd without isomeric designation. (2E,6E,10E)-geranylgeranic acid : A diterpenoid obtained by formal oxidation of the CH2OH group of (E,E,E)-geranylgeraniol to the corresponding carboxylic acid.	2.07	1	0	alpha,beta-unsaturated monocarboxylic acid; diterpenoid; methyl-branched fatty acid; trienoic fatty acid
quercetin [no description available]	3.9	3	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
bilirubin [no description available]	2.41	1	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.96	4	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	2.07	1	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
biochanin a [no description available]	2.07	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	antineoplastic agent; EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
formononetin [no description available]	2.07	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	phytoestrogen; plant metabolite
prostaglandin b1 prostaglandin Bx: phospholipase A2 inhibitor; polymeric derivative of diketo-PGB1; mean MW 2,200. prostaglandin B1 : A member of the class of prostaglandins B that is prosta-8(12),13-dien-1-oic acid carrying oxo and hydroxy substituents at positions 9 and 15 respectively (the 13E,15S-stereoisomer).	2.07	1	0	prostaglandins B	human metabolite
sterigmatocystin [no description available]	2.07	1	0	sterigmatocystins	metabolite
vitexin [no description available]	2.07	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.	2.07	1	0	dihydroxyflavone; monomethoxyflavone	anticonvulsant; plant metabolite
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	2.07	1	0	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	2.45	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
calcitriol dihydroxy-vitamin D3: as a major in vitro metabolite of 1alpha,25-dihydroxyvitamin D3, produced in primary cultures of neonatal human keratinocytes	2.01	1	0	D3 vitamins; hydroxycalciol; triol	antineoplastic agent; antipsoriatic; bone density conservation agent; calcium channel agonist; calcium channel modulator; hormone; human metabolite; immunomodulator; metabolite; mouse metabolite; nutraceutical
quercitrin [no description available]	2.07	1	0	alpha-L-rhamnoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	antileishmanial agent; antioxidant; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; plant metabolite
scopoletin [no description available]	2.07	1	0	hydroxycoumarin	plant growth regulator; plant metabolite
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
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]	3.91	3	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
9-deoxy-delta-9-prostaglandin d2 9-deoxy-delta-9-prostaglandin D2: has potent antineoplastic & weak smooth muscle contracting activities; structure given in first source. prostaglandin J2 : A member of the class of prostaglandins J that consists of prosta-5,9,13-trien-1-oic acid substituted by an oxo group at position 11 and a hydroxy group at position 15 (the 5Z,13E,15S stereoisomer).	2.02	1	0	prostaglandins J	human 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]	9.55	7	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
butein [no description available]	2.07	1	0	chalcones; polyphenol	antineoplastic agent; antioxidant; EC 1.1.1.21 (aldehyde reductase) inhibitor; geroprotector; hypoglycemic agent; plant metabolite; radiosensitizing agent; tyrosine kinase inhibitor
sulfuretin sulfuretin: the chalcone C ring closes into a 5 instead of the more typical 6 membered ring leaving a phenyl methane at the 2 position instead of the typical phenyl	2.07	1	0	1-benzofurans
genistin genistin: glycoside of soy bean isoflavone, gentistein	2.07	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside
chartreusin chartreusin: structure	2.07	1	0	benzochromenone; glycoside
garcinol garcinol: from stem bark of Garcinia huillensis; has chemotherapeutic activity against gram-positive & gram-negative cocci, mycobacteria & fungi	3.23	1	0
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.	2.45	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]	2.46	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
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	2.07	1	0	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
rosmarinic acid rosmarinic acid: RN given refers to parent cpd; promote OT project. (R)-rosmarinic acid : A stereoisomer of rosmarinic acid having (R)-configuration.. rosmarinic acid : The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.	2.07	1	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]	2.53	2	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
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
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.	2.46	2	0	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
brefeldin a [no description available]	2.07	1	0	macrolide antibiotic	Penicillium metabolite
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
kn 93 KN 93: reduces dopamine content in PC12h cells. KN-93 : A sulfonamide resulting from the formal condensation of p-methoxybenzenesulfonic acid with the anilino nitrogen of 2-(aminomethyl)-N-(2-hydroxyethyl)aniline in which the hydrogens of the primary amino group have been replaced by methyl and p-chlorocinnamyl groups. KN-93 is a selective inhibitor of Ca(2+)/calmodulin-dependent protein kinase II.	2.03	1	0	monochlorobenzenes; monomethoxybenzene; primary alcohol; sulfonamide; tertiary amino compound	EC 2.7.11.17 (Ca(2+)/calmodulin-dependent protein kinase) inhibitor; geroprotector
bisdemethoxycurcumin curcumin III: structure in first source. bisdemethoxycurcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups.	2.07	1	0	beta-diketone; diarylheptanoid; enone; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; metabolite
andrographolide [no description available]	2.07	1	0	carbobicyclic compound; gamma-lactone; labdane diterpenoid; primary alcohol; secondary alcohol	anti-HIV agent; anti-inflammatory drug; antineoplastic agent; metabolite
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
6,7-dihydroxyflavone 6,7-dihydroxyflavone: intensifies effect of antibiotics on Staphylococcus aureus; structure in first source	2.07	1	0
flavokawain a flavokawain A: from kava extract, induces apoptosis in bladder cancer cells; structure in first source	2.07	1	0	chalcones
flavokawain b flavokawain B: from Piper methysticum Forst (Kava Kava) roots; structure in first source. flavokawain B : A member of the class of chalcones that consists of trans-chalcone substituted by hydroxy group at positions 2' and methoxy groups at positions 4' and 6'. Isolated from Piper methysticum and Piper rusbyi, it exhibits antileishmanial, anti-inflammatory and antineoplastic activities.	2.07	1	0	chalcones; dimethoxybenzene; phenols	anti-inflammatory agent; antileishmanial agent; antineoplastic agent; apoptosis inducer; metabolite
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.	2.46	2	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
bakuchiol bakuchiol: chief component of Psoralea corylifolia Linn; structure	2.07	1	0
zerumbone zerumbone: RN given for (E,E,E)-isomer; structure in first source. zerumbone : A sesquiterpenoid and cyclic ketone that is (1E,4E,8E)-alpha-humulene which is substituted by an oxo group at the carbon atom attached to two double bonds. It is obtained by steam distillation from a type of edible ginger, Zingiber zerumbet Smith, grown particularly in southeast Asia.	2.07	1	0	cyclic ketone; sesquiterpenoid	anti-inflammatory agent; glioma-associated oncogene inhibitor; plant metabolite
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
sinigrin sinigrin: glucosinate in mustard seeds etc.; RN given refers to parent cpd. sinigrin : An alkenylglucosinolic acid that consists of 1-thio-beta-D-glucopyranose having a 4-[(sulfooxy)imino]but-1-en-4-yl group attached to the anomeric sulfur.	2.13	1	0	alkenylglucosinolic acid
(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
bafilomycin a [no description available]	2.07	1	0
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
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
sulphoraphene sulphoraphene: from radish; structure in first source	3.06	1	0
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
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
etoposide phosphate [no description available]	2.08	1	0	furonaphthodioxole
anisodamine [no description available]	2.07	1	0
bufalin bufalin: cardiotonic; powerful anesthetic & one of the active constituents of the Chinese drug ch'an su(senso); in Japan prepared from skin of Bufo bufo garfarizans; RN given refers to (3beta,5beta)-isomer. bufalin : A 14beta-hydroxy steroid that is bufan-20,22-dienolide having hydroxy substituents at the 5beta- and 14beta-positions. It has been isolated from the skin of the toad Bufo bufo.	2.07	1	0	14beta-hydroxy steroid; 3beta-hydroxy steroid	animal metabolite; anti-inflammatory agent; antineoplastic agent; cardiotonic drug
glucoiberin glucoiberin: from Iberis amara; structure in first source	2.13	1	0
alpha-solanine [no description available]	2.07	1	0	glycoalkaloid; organic heterohexacyclic compound; steroid saponin; trisaccharide derivative	antineoplastic agent; apoptosis inducer; phytotoxin; plant metabolite
formazans Formazans: Colored azo compounds formed by the reduction of tetrazolium salts. Employing this reaction, oxidoreductase activity can be determined quantitatively in tissue sections by allowing the enzymes to act on their specific substrates in the presence of tetrazolium salts.	2	1	0
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
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	2.42	2	0	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
bn 52020 [no description available]	2.07	1	0
4-hydroxyestrone 4-hydroxyestrone : A 4-hydroxy steroid that is estrone substituted by a hydroxy group at position 4.	4.45	1	1	17-oxo steroid; 3-hydroxy steroid; 4-hydroxy steroid; catechols; phenolic steroid	carcinogenic agent; estrogen; human urinary metabolite
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
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
nutlin-3a nutlin 3: an MDM2 antagonist; structure in first source	2.25	1	0	stilbenoid
calcimycin Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.	2.07	1	0	benzoxazole
cinobufagin cinobufagin: isolated from Chinese medicinal preparation ch'an su; derived from toad venom	2.07	1	0	steroid lactone
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
hypocrellin a hypocrellin A: isolated from fungus Hypocrella bambusae sacc	2.07	1	0
mdv 3100 [no description available]	2.31	1	0	(trifluoromethyl)benzenes; benzamides; imidazolidinone; monofluorobenzenes; nitrile; thiocarbonyl compound	androgen antagonist; antineoplastic agent
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.73	3	0
atrial natriuretic factor Atrial Natriuretic Factor: A potent natriuretic and vasodilatory peptide or mixture of different-sized low molecular weight PEPTIDES derived from a common precursor and secreted mainly by the HEART ATRIUM. All these peptides share a sequence of about 20 AMINO ACIDS.	2.11	1	0	polypeptide
oligonucleotides [no description available]	2.08	1	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	7.25	1	0	glycoside
(9R)-9-chloro-11,17-dihydroxy-17-(2-hydroxy-1-oxoethyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one Beclomethasone: An anti-inflammatory, synthetic glucocorticoid. It is used topically as an anti-inflammatory agent and in aerosol form for the treatment of ASTHMA.. beclomethasone : A 17alpha-hydroxy steroid that is prednisolone in which the hydrogens at the 9alpha and 16beta positions are substituted by a chlorine and a methyl group, respectively.	2.02	1	0	21-hydroxy steroid
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	2.31	1	0	chlorophyll; methyl ester	cofactor
dihydrorobinetin dihydrorobinetin: structure in first source	2.07	1	0
chitosan [no description available]	7.53	2	0
mesna Mesna: A sulfhydryl compound used to prevent urothelial toxicity by inactivating metabolites from ANTINEOPLASTIC AGENTS, such as IFOSFAMIDE or CYCLOPHOSPHAMIDE.	1.93	1	0	organosulfonic acid
monensin [no description available]	2.07	1	0
ethyl cellulose [no description available]	2.25	1	0	glycoside
natriuretic peptide, brain Natriuretic Peptide, Brain: A PEPTIDE that is secreted by the BRAIN and the HEART ATRIA, stored mainly in cardiac ventricular MYOCARDIUM. It can cause NATRIURESIS; DIURESIS; VASODILATION; and inhibits secretion of RENIN and ALDOSTERONE. It improves heart function. It contains 32 AMINO ACIDS.	2.11	1	0	polypeptide
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.	2.77	3	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
epidermal growth factor Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.	2.07	1	0
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	2.8	3	0
phytoestrogens Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.	4.39	3	0
ajmaline [no description available]	2.07	1	0
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	8.47	7	0
transforming growth factor alpha Transforming Growth Factor alpha: An EPIDERMAL GROWTH FACTOR related protein that is found in a variety of tissues including EPITHELIUM, and maternal DECIDUA. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form which binds to the EGF RECEPTOR.	2	1	0
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	2.03	1	0
icg 001 ICG 001: PRI-724 is an enantiomer of ICG-001; binds to cAMP response element-binding protein; structure in first source	3.25	1	0
guanosine monophosphate Guanosine Monophosphate: A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature.. guanosine 5'-monophosphate : A purine ribonucleoside 5'-monophosphate having guanine as the nucleobase.	2.08	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	biomarker; Escherichia coli metabolite; metabolite; mouse metabolite
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)	2.07	1	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
alpha-cyclopiazonic acid [no description available]	2.07	1	0	alpha-cyclopiazonic acids
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	3.25	1	0

3,3'-diindolylmethane

Description

Cross-References

Synonyms (114)

Research Excerpts

Toxicity

Pharmacokinetics

Bioavailability

Dosage Studied

Occurs in Manufacturing (29 Product(s))

Product Categories

Products

Roles (2)

Drug Classes (1)

Pathways (1)

Protein Targets (31)

Potency Measurements

Activation Measurements

Other Measurements

Biological Processes (15)

Molecular Functions (11)

Ceullar Components (8)

Bioassays (139)

Research

Studies (399)

Market Indicators

Research Demand Index: 26.07

Study Types

Clinical Trials (15)

Trial Overview

Trial Outcomes

Estradiol Level in Blood Post Treatment

Estradiol Level in Blood Pre Treatment

Number of Cases With Recurrence of Laryngeal Papilloma in 5 Months

Mean Level of Diindolylmethane in Prostate Tissue After Treatment

Levels of Androgen Receptor in Prostate Tissue

Serum Levels of PSA, Testosterone, and Diindolylmethane

Condition	Indicated	Relationship Strength	Studies	Trials
Malignant Melanoma [description not available]	0	7.81	3	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	0	7.81	3	0
Encephalitis, Polio [description not available]	0	2.06	1	0
Poliomyelitis An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)	0	2.06	1	0
Breast Cancer [description not available]	0	10.91	54	5
Breast Neoplasms Tumors or cancer of the human BREAST.	1	12.91	54	5
Benign Neoplasms [description not available]	0	7.04	9	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	0	7.04	9	0
Benign Neoplasms, Brain [description not available]	0	2.15	1	0
Astrocytoma, Grade IV [description not available]	0	2.15	1	0
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	0	2.15	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.	0	2.15	1	0
Diseases of Immune System [description not available]	0	3.17	1	0
Immune System Diseases Disorders caused by abnormal or absent immunologic mechanisms, whether humoral, cell-mediated, or both.	0	3.17	1	0
Congenital Zika Syndrome [description not available]	0	2.25	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	0	6.26	19	0
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	0	2.25	1	0
Cryptogenic Fibrosing Alveolitis [description not available]	0	2.25	1	0
Bowel Diseases, Inflammatory [description not available]	0	2.63	2	0
Inflammatory Bowel Diseases Chronic, non-specific inflammation of the GASTROINTESTINAL TRACT. Etiology may be genetic or environmental. This term includes CROHN DISEASE and ULCERATIVE COLITIS.	0	2.63	2	0
Idiopathic Pulmonary Fibrosis A common interstitial lung disease of unknown etiology, usually occurring between 50-70 years of age. Clinically, it is characterized by an insidious onset of breathlessness with exertion and a nonproductive cough, leading to progressive DYSPNEA. Pathological features show scant interstitial inflammation, patchy collagen fibrosis, prominent fibroblast proliferation foci, and microscopic honeycomb change.	0	2.25	1	0
Blood Clot [description not available]	0	3.57	2	0
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	0	8.57	2	0
Cancer of Stomach [description not available]	0	3.69	9	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	0	3.69	9	0
Anhedonia Inability to experience pleasure due to impairment or dysfunction of normal psychological and neurobiological mechanisms. It is a symptom of many PSYCHOTIC DISORDERS (e.g., DEPRESSIVE DISORDER, MAJOR; and SCHIZOPHRENIA).	0	2.41	1	0
Palmoplantaris Pustulosis [description not available]	0	2.41	1	0
Dermatitis Any inflammation of the skin.	0	2.41	1	0
Psoriasis A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.	0	2.41	1	0
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	0	2.96	3	0
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	0	2.96	3	0
Cirrhosis, Liver [description not available]	0	2.41	1	0
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	0	2.41	1	0
Angiogenesis, Pathologic [description not available]	0	4.49	8	0
Carcinoma, Anaplastic [description not available]	0	3.04	4	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	0	3.04	4	0
Colitis Gravis [description not available]	0	2.93	3	0
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	0	2.93	3	0
Anoxemia [description not available]	0	2.6	1	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	0	2.6	1	0

3,3'-diindolylmethane

Description

Cross-References

Synonyms (114)

Research Excerpts

Toxicity

Pharmacokinetics

Bioavailability

Dosage Studied

Occurs in Manufacturing (29 Product(s))

Product Categories

Products

Roles (2)

Drug Classes (1)

Pathways (1)

Protein Targets (31)

Potency Measurements

Activation Measurements

Other Measurements

Biological Processes (15)

Molecular Functions (11)

Ceullar Components (8)

Bioassays (139)

Research

Studies (399)

Market Indicators

Research Demand Index: 26.07

Study Types

Clinical Trials (15)

Trial Overview

Trial Outcomes

Estradiol Level in Blood Post Treatment

Estradiol Level in Blood Pre Treatment

Number of Cases With Recurrence of Laryngeal Papilloma in 5 Months

Mean Level of Diindolylmethane in Prostate Tissue After Treatment

Levels of Androgen Receptor in Prostate Tissue

Serum Levels of PSA, Testosterone, and Diindolylmethane

Related Drugs (576)

Related Conditions (220)