gentiopicroside profile

Gentiopicroside is a secoiridoid glycoside found in the roots of Gentiana species. It is known for its diverse pharmacological activities, including anti-inflammatory, antioxidant, hepatoprotective, and antidiabetic effects. Research has shown that gentiopicroside can inhibit the production of pro-inflammatory cytokines, scavenge free radicals, protect liver cells from damage, and enhance insulin sensitivity. It is also being investigated for its potential to treat various diseases, including cancer and Alzheimer's disease. The synthesis of gentiopicroside involves the extraction from natural sources, although attempts to develop synthetic routes are underway. Its importance stems from its promising therapeutic potential and its potential for development as a drug or dietary supplement.'

gentiopicroside: a secoiridoid in Gentiana with rearrangement to two pyran rings [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Related Flora

Flora	Rank	Flora Definition	Family	Family Definition
Gentiana	genus	A plant genus of the family Gentianaceae whose members contain SECOIRIDOIDS and have been used in TRADITIONAL MEDICINE for suppressing INFLAMMATION.[MeSH]	Gentianaceae	A plant family of the order Gentianales, subclass Asteridae, class Magnoliopsida.[MeSH]

ID Source	ID
PubMed CID	88708
CHEMBL ID	508320
CHEBI ID	5321
SCHEMBL ID	154304
MeSH ID	M0060415

Synonym
AC-20248
nsc-606402
ACON1_001284
NCGC00180669-01
MEGXP0_000872
gentiopicroside
gentiopicrin
C09782
20831-76-9
LMPR0102070009
BRD-K33131085-001-01-5
smr001397341
MLS002473254
CHEMBL508320
chebi:5321 ,
(3s,4r)-4-ethenyl-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3h-pyrano[3,4-c]pyran-8-one
A814958
(5beta-trans)-6-(beta-d-glucopyranosyloxy)-5,6-dihydro-5-vinyl-1h,3h-pyrano[3,4-c]pyran-1-one
HMS2198G10
nsc 606402
unii-0we09z21rc
einecs 244-070-2
0we09z21rc ,
1h,3h-pyrano(3,4-c)pyran-1-one, 5-ethenyl-6-(beta-d-glucopyranosyloxy)-5,6-dihydro-, (5r-trans)-
(5r-trans)-6-(beta-d-glucopyranosyloxy)-5,6-dihydro-5-vinyl-1h,3h-pyrano(3,4-c)pyran-1-one
S3777
AKOS015896721
gentiopicrin [mi]
(5r,6s)-5-ethenyl-6-(.beta.-d-glucopyranosyloxy)-5,6-dihydro-1h,3h-pyrano(3,4-c)pyran-1-one
SCHEMBL154304
AC-33960
mfcd00075700
(5r,6s)-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,3h,5h,6h-pyrano[3,4-c]pyran-1-one
AS-74360
gentiopicroside, >=98% (hplc)
CS-0009015
HY-N0494
(5r,6s)-6-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)-5-vinyl-5,6-dihydropyrano[3,4-c]pyran-1(3h)-one
gentiopicrin,(s)
Q27106718
(5r-trans)-6-(b-d-glucopyranosyloxy)-5,6-dihydro-5-vinyl-1h,3h-pyrano[3,4-c]pyran-1-one
ZB1867
(5r,6s)-6-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-5-vinyl-5,6-dihydropyrano[3,4-c]pyran-1(3h)-one
CCG-268110
DTXSID40878043 ,
G0576
EX-A6716
dtxcid501016106

Research Excerpts

Overview

Gentiopicroside is a major active component of the Gentiana scabra Bge., which is commonly used as herbal medicine for the treatment of inflammation in Asia. Gentiopicro side is an important plant secondary metabolite and has been reported to exhibit tremendous pharmacological potential.

Excerpt	Reference	Relevance
"Gentiopicroside is a major active component of the Gentiana scabra Bge., which is commonly used as herbal medicine for the treatment of inflammation in Asia. "	( Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice. Choi, RY; Lee, HI; Lee, J; Lee, MK; Leutou, AS; Nam, SJ; Ri Ham, J, 2019)	3.4
"Gentiopicroside (GEN) is a secoiridoid glycosides isolated from a traditional Chinese medicine Gentiana macrophylla Pall.. "	( Gentiopicroside attenuates collagen-induced arthritis in mice via modulating the CD147/p38/NF-κB pathway. Cui, J; Ding, Y; Jia, N; Ma, H; Wang, J; Wang, L; Zha, Y; Zhang, T, 2022)	3.61
"Gentiopicroside is a novel selective inhibitor of cyclooxygenase-2 from Chinese herbal medicine."	( Synthesis and Biological Evaluation of Gentiopicroside Derivatives as Novel Cyclooxygenase-2 Inhibitors with Anti-Inflammatory Activity. Fang, P; Jin, X; Peng, X; Ren, G; Wang, J; Xia, P; Xu, Y; Zhang, J; Zhang, Q; Zhao, L, 2023)	1.9
"Gentiopicroside (GPS) is a secoiridoid glycoside compound that exhibits anti-inflammatory property."	( Gentiopicroside ameliorates ovalbumin-induced airway inflammation in a mouse model of allergic asthma via regulating SIRT1/NF-κB signaling pathway. Cao, C; Fu, Y; Kong, L; Pan, D; Wang, W; Zou, B, 2021)	2.79
"Gentiopicroside (GPS) is a natural secoiridoid glycoside from gentian species of medicinal plants, and has a variety of pharmacological activities, including hepatoprotective and cholagogic, anti-inflammatory, antinociceptive, and smooth muscle relaxing activities."	( Gentiopicroside ameliorates bleomycin-induced pulmonary fibrosis in mice via inhibiting inflammatory and fibrotic process. Chen, C; Cheng, MQ; Hong, ZP; Wang, YX; Wang, YY; Yin, JB; Zhang, X, 2018)	2.64
"Gentiopicroside is an important plant secondary metabolite and has been reported to exhibit tremendous pharmacological potential. "	( Gentiopicroside exerts convincing antitumor effects in human ovarian carcinoma cells (SKOV3) by inducing cell cycle arrest, mitochondrial mediated apoptosis and inhibition of cell migration. Li, X; Shen, H; Yang, C, )	3.02
"Gentiopicroside (Gent) is a secoiridoid compound isolated from Gentiana lutea that exhibits analgesic properties and inhibits the expression of GluN2B-containing N-methyl-D-aspartate (NMDA) receptors in the anterior cingulate cortex of mice."	( Attenuation of reserpine-induced pain/depression dyad by gentiopicroside through downregulation of GluN2B receptors in the amygdala of mice. Gao, GD; Guo, HJ; Li, XS; Liu, SB; Tian, Z; Zhang, N; Zhao, MG; Zhao, R, 2014)	1.37
"Gentiopicroside is a major component of Gentianae radix and Gentianae scabrae radix."	( Application of quantitative 1H-NMR method to determination of gentiopicroside in Gentianae radix and Gentianae scabrae radix. Hasebe, Y; Nagatsu, A; Tanaka, R, 2014)	1.36
"Gentiopicroside is a secoiridoid compound isolated from Gentiana lutea which is called Qin Jiao in Chinese. "	( Research Progress of Natural Product Gentiopicroside - a Secoiridoid Compound. Dechoux, L; Ning, Y; Sollogoub, M; Sun, W; Thorimbert, S; Wu, S; Zhang, Y; Zhao, Y, 2017)	2.17
"Gentiopicroside (GPS) is a secoiridoid glucoside isolated from the ethanol extract of Gentianae Radix with a content of 13%, which has been used for centuries in Chinese as a digestive aid."	( Isolation of gentiopicroside from Gentianae Radix and its pharmacokinetics on liver ischemia/reperfusion rats. Chang-Liao, WL; Chien, CF; Lin, LC; Tsai, TH, 2012)	2.19

Effects

Excerpt	Reference	Relevance
"Gentiopicroside (Gent) has powerful anti-inflammatory property and exhibits promising antidepressant effect in an animal model of pain/depression dyad by down-regulating GluN2B-containing NMDA receptors."	( Gentiopicroside abrogates lipopolysaccharide-induced depressive-like behavior in mice through tryptophan-degrading pathway. Deng, YT; Li, XH; Xu, TJ; Zhao, MG, 2018)	2.64

Actions

Excerpt	Reference	Relevance
"Gentiopicroside could inhibit apoptosis caused by corticosterone, and also decrease neuronal cell proliferation and BDNF levels in vitro."	( Metabolomic evidence for the therapeutic effect of gentiopicroside in a corticosterone-induced model of depression. Cui, Q; Liu, Z; Wang, C; Wang, G; Yao, T; Zhang, Q, 2019)	1.49

Pharmacokinetics

There are significantly differences in pharmacokinetic parameters between gentiopicroside and Gentianae Radix extract in rats. The effects of gentiopMicroside, gastrodin, and sweroside in rats were dose-dependent when the dose of JWXF was 1-4 g/kg.

Excerpt	Reference	Relevance
" The study confirms the importance of careful pharmacokinetic analysis in the characterization of herbal medicines when applied for future clinical applications."	( Pharmacokinetic behavior of gentiopicroside from decoction of Radix Gentianae, Gentiana macrophylla after oral administration in rats: a pharmacokinetic comaprison with gentiopicroside after oral and intravenous administration alone. Bligh, SW; Branford-White, CJ; Cheng, XM; He, YQ; Wang, CH; Wang, ZT; White, KN, 2007)	0.63
" This method was successfully applied to determination of the pharmacokinetic properties of swertiamarin in rats after oral administration at a dose of 20 mg/kg."	( Development and validation of a LC-ESI-MS/MS method for the determination of swertiamarin in rat plasma and its application in pharmacokinetics. Feng, EF; He, JC; Li, HL; Peng, XJ; Rao, GX; Xu, GL, 2011)	0.37
"The area under concentration curve (AUC) was significantly increased; however, the clearance (Cl) was significantly decreased in the liver I/R rats."	( Isolation of gentiopicroside from Gentianae Radix and its pharmacokinetics on liver ischemia/reperfusion rats. Chang-Liao, WL; Chien, CF; Lin, LC; Tsai, TH, 2012)	0.75
" The main pharmacokinetic parameters of gentiopicroside and Gentianae Radix extract were: C(max) (16."	( [Comparative study on pharmacokinetics of gentiopicroside and gentianae radix extract in rats]. Duan, JC; Feng, B; Gu, JK; Guan, J; Hao, CY; Zhu, HY, 2013)	0.92
"There are significantly differences in pharmacokinetic parameters between gentiopicroside and Gentianae Radix extract in rats."	( [Comparative study on pharmacokinetics of gentiopicroside and gentianae radix extract in rats]. Duan, JC; Feng, B; Gu, JK; Guan, J; Hao, CY; Zhu, HY, 2013)	0.89
" The method was fully validated and applied to a pharmacokinetic study involving oral administration of a Radix Gentianae extract to groups of male and female rats."	( A rapid and sensitive UFLC-MS/MS method for the simultaneous determination of gentiopicroside and swertiamarin in rat plasma and its application in pharmacokinetics. Fawcett, JP; Feng, B; Gu, J; Guan, J; Liu, W; Yin, L; Zhao, L; Zhu, H, 2014)	0.63
"There were remarkable differences in pharmacokinetic properties of gentiopicroside and swertiamarin between male and female rats."	( A rapid and sensitive UFLC-MS/MS method for the simultaneous determination of gentiopicroside and swertiamarin in rat plasma and its application in pharmacokinetics. Fawcett, JP; Feng, B; Gu, J; Guan, J; Liu, W; Yin, L; Zhao, L; Zhu, H, 2014)	0.87
" The pharmacokinetic data demonstrated that the area under concentration-time curve (AUC) values of gentiopicroside, geniposide, baicalin, and swertiamarin were 1417 ± 83."	( Determination and pharmacokinetic study of gentiopicroside, geniposide, baicalin, and swertiamarin in Chinese herbal formulae after oral administration in rats by LC-MS/MS. Lin, LC; Lu, CM; Tsai, TH, 2014)	0.88
" Pharmacokinetic analysis showed that the effects of gentiopicroside, gastrodin, and sweroside in rats were dose-dependent when the dose of JWXF was 1-4 g/kg."	( Discovery of the material basis of Jiuwei Xifeng granules using pharmaco-chemistry and pharmacokinetics. Cao, L; Chen, X; Gao, H; Gao, X; Wang, J; Wang, Z; Xiao, W, 2023)	1.16

Compound-Compound Interactions

Excerpt	Reference	Relevance
"LEF and/or MTX combined with GPS ameliorated oxidative stress by increasing the mRNA levels of the antioxidant gene Nrf2, GCLC, HO-1, and NQO1, increasing the antioxidant enzymes superoxide dismutase (SOD), glutathione (GSH) and catalase (CAT), reducing the oxidant substance malondialdehyde (MDA), reducing the inflammatory response by decreasing the mRNA levels of NF-κB, tumour necrosis factor-α (TNF-α), interleukin-1β (IL-1β), and interleukin-6 (IL-6), and inhibiting the secretion of the pro-inflammatory cytokines TNFα, IL-6, IL-1β and reducing C-reactive protein (CRP), as well as alleviating the external symptoms of arthritis."	( Hepatoprotective effect of gentiopicroside in combination with leflunomide and/or methotrexate in arthritic rats. Li, H; Li, M; Li, X; Liu, J; Liu, Q; Wan, Z; Wang, R; Wu, X; Zhao, H, 2021)	0.92

Bioavailability

In jejunum the constant of absorption rate (Ka) of gentiopicroside and swertiamarin increased with the raised dosage of Gentianae Radix et Rhizoma.

Excerpt	Reference	Relevance
"50 h, and the bioavailability was 39."	( Pharmacokinetics and tissue distribution of gentiopicroside following oral and intravenous administration in mice. Bligh, SW; Wang, CH; Wang, ZT; White, CJ; White, KN, )	0.39
"The pharmacokinetics and bioavailability of gentiopicroside (GPS), an active component of the Gentian plant species, from orally administered decoctions of Gentianae (DG), or in combination with other plants in the prescription of Longdan Xiegan Tang (LXT), was compared in rats with oral administration of GPS alone, using doses adjusted to deliver equivalent amounts of GPS (150 mg/kg)."	( Pharmacokinetics and bioavailability of gentiopicroside from decoctions of Gentianae and Longdan Xiegan Tang after oral administration in rats--comparison with gentiopicroside alone. Bligh, SW; Branford-White, CJ; Cheng, XM; Wang, CH; Wang, ZT; White, KN, 2007)	0.87
" The results demonstrate that the bioavailability of GPS was markedly improved when administered as a decoction than as purified GPS."	( Pharmacokinetic behavior of gentiopicroside from decoction of Radix Gentianae, Gentiana macrophylla after oral administration in rats: a pharmacokinetic comaprison with gentiopicroside after oral and intravenous administration alone. Bligh, SW; Branford-White, CJ; Cheng, XM; He, YQ; Wang, CH; Wang, ZT; White, KN, 2007)	0.63
" The oral bioavailability of GPS was 10."	( Isolation of gentiopicroside from Gentianae Radix and its pharmacokinetics on liver ischemia/reperfusion rats. Chang-Liao, WL; Chien, CF; Lin, LC; Tsai, TH, 2012)	0.75
" Micro-needles can be used as the ideal ingredients for traditional Chinese medicine complex transdermal delivery; transdermal absorption time delay could be greatly reduced and its bioavailability was improved."	( [Transdermal delivery of Gentiana macrophylla complex components system under micro-needle conditions]. Chen, G; Dou, JJ; Hao, BH; Hui, X; Ju, DH; Xu, K; Yan, JH, 2011)	0.37
"Results showed that in female rats, both compounds were absorbed to a greater extent and eliminated more slowly than in male rats, although the rate of absorption was similar in the two groups."	( A rapid and sensitive UFLC-MS/MS method for the simultaneous determination of gentiopicroside and swertiamarin in rat plasma and its application in pharmacokinetics. Fawcett, JP; Feng, B; Gu, J; Guan, J; Liu, W; Yin, L; Zhao, L; Zhu, H, 2014)	0.63
"In this study, the effect of D-cellobiose on oral bioavailability of gentiopicroside (GPS) was investigate."	( [Effect of D-cellobiose on oral bioavailability of gentiopicroside]. Dai, YH; Ju, JM; Wang, LL; Wang, M; Zhang, ZH; Zhu, YN, 2016)	0.92
" However, it is highly hydrophilic owing to the presence of the sugar fragment in its structure that reduces its oral bioavailability and limits efficacy."	( Synthesis and Biological Evaluation of Gentiopicroside Derivatives as Novel Cyclooxygenase-2 Inhibitors with Anti-Inflammatory Activity. Fang, P; Jin, X; Peng, X; Ren, G; Wang, J; Xia, P; Xu, Y; Zhang, J; Zhang, Q; Zhao, L, 2023)	1.18

Dosage Studied

Excerpt	Relevance	Reference
" The results will provide helpful information for the development of suitable dosage forms and clinical references on rational administration."	( A rapid and sensitive UFLC-MS/MS method for the simultaneous determination of gentiopicroside and swertiamarin in rat plasma and its application in pharmacokinetics. Fawcett, JP; Feng, B; Gu, J; Guan, J; Liu, W; Yin, L; Zhao, L; Zhu, H, 2014)	0.63
" The pharmacokinetic profiles provide constructive information for the dosage regimen of herbal medicine and also contribute to elucidate the absorption mechanism in herbal applications and pharmacological experiments."	( Determination and pharmacokinetic study of gentiopicroside, geniposide, baicalin, and swertiamarin in Chinese herbal formulae after oral administration in rats by LC-MS/MS. Lin, LC; Lu, CM; Tsai, TH, 2014)	0.67
"In order to optimize the base fertilizer dosage and root size of Gentiana crassicaulis in Ludian,Yulong, Yunnan,the differences in yield and quality of Gentiana crassicaulis caused by different base fertilizer dosage and root size were investigated."	( [Influences of Base Fertilizer Dosage and Root Size on Quality and Yield of Gentiana crassicaulis Root]. Chen, XF; Cheng, T; Meng, J; Song, JH; Yang, WY; Zeng, Y, 2015)	0.42
"There were big differences in yield and quality of Gentiana crassicaulis among different base fertilizer dosage and root size."	( [Influences of Base Fertilizer Dosage and Root Size on Quality and Yield of Gentiana crassicaulis Root]. Chen, XF; Cheng, T; Meng, J; Song, JH; Yang, WY; Zeng, Y, 2015)	0.42

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Class	Description
glycoside	A glycosyl compound resulting from the attachment of a glycosyl group to a non-acyl group RO-, RS-, RSe-, etc. The bond between the glycosyl group and the non-acyl group is called a glycosidic bond. By extension, the terms N-glycosides and C-glycosides are used as class names for glycosylamines and for compounds having a glycosyl group attached to a hydrocarbyl group respectively. These terms are misnomers and should not be used. The preferred terms are glycosylamines and C-glycosyl compounds, respectively.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
USP1 protein, partial	Homo sapiens (human)	Potency	50.1187	0.0316	37.5844	354.8130	AID743255
Smad3	Homo sapiens (human)	Potency	0.8913	0.0052	7.8098	29.0929	AID588855
chromobox protein homolog 1	Homo sapiens (human)	Potency	100.0000	0.0060	26.1688	89.1251	AID540317
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (69)

Assay ID	Title	Year	Journal	Article
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810	Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504812	Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID465473	Mutagenic activity in Salmonella typhimurium TA98 assessed as increase in number of revertants at 60 ug/plate by Ames test presence of S9 fraction (Rvb=34+/- 4)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465470	Mutagenic activity in Salmonella Typhimurium TA98 assessed as increase in number of revertants at 100 ug/plate by Ames test absence of S9 fraction (Rvb=22+/- 4)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1446882	Antiviral activity against HCV pseudoparticle harboring HCV envelope protein E1 and E2 assessed as inhibition of pseudoparticle entry into human Huh7 cells at 5 uM measured after 3 days by Bright-Glo luciferase reporter gene assay relative to control	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Design, synthesis and biological evaluation of gentiopicroside derivatives as potential antiviral inhibitors.
AID465367	Mutagenic activity in Salmonella typhimurium TA98 assessed as increase in number of revertants at 60 ug/plate by Ames test absence of S9 fraction (Rvb=22+/- 4)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465493	Mutagenic activity in Salmonella Typhimurium TA100 assessed as increase in number of revertants at 60 ug/plate by Ames test presence of S9 fraction (Rvb=124+/-13)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465495	Mutagenic activity in Salmonella typhimurium TA100 assessed as increase in number of revertants at 100 ug/plate by Ames test presence of S9 fraction (Rvb=124+/-13)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465506	Cytotoxicity activity against CHO cells assessed as cell viability after 2 hrs by WST1 test	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1545072	Cytotoxicity against mouse 3T3L1 cells assessed as reduction in cell viability up to 10 uM	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID465497	Mutagenic activity in Salmonella Typhimurium TA102 assessed as increase in number of revertants at 40 ug/plate by Ames test absence of S9 fraction (Rvb=290+/-10)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465487	Mutagenic activity in Salmonella Typhimurium TA100 assessed as increase in number of revertants at 40 ug/plate by Ames test absence of S9 fraction (Rvb=108+/-5)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID390344	Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 by FACS	2008	Journal of natural products, Dec, Volume: 71, Issue:12	Fagraldehyde, a secoiridoid isolated from Fagraea fragrans.
AID465503	Mutagenic activity in Salmonella Typhimurium TA102 assessed as increase in number of revertants at 60 ug/plate by Ames test presence of S9 fraction (Rvb=369+/-34)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465469	Mutagenic activity in Salmonella Typhimurium TA98 assessed as increase in number of revertants at 80 ug/plate by Ames test absence of S9 fraction (Rvb=22+/- 4)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465480	Mutagenic activity in Salmonella Typhimurium TA97a assessed as increase in number of revertants at 100 ug/plate by Ames test absence of S9 fraction (Rvb=146+/- 8)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1545085	Downregulation of FAS mRNA expression in mouse 3T3L1 cells up to 10 uM incubated for 8 days followed by compound wash out measured by RT-PCR method	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID465489	Mutagenic activity in Salmonella typhimurium TA100 assessed as increase in number of revertants at 80 ug/plate by Ames test absence of S9 fraction (Rvb=108+/-5)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1545082	Antiinflammatory activity in mouse 3T3L1 cells assessed as reduction in TNFalpha mRNA expression up to 10 uM incubated for 8 days followed by compound wash out measured by RT-PCR method	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID465479	Mutagenic activity in Salmonella Typhimurium TA97a assessed as increase in number of revertants at 80 ug/plate by Ames test absence of S9 fraction (Rvb=146+/- 8)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1545090	Antiobesity activity in HFD-induced obese C57BL/6N mouse model assessed as reduction in epididymal WAT adipocyte size at 50 mg/kg, po administered once daily for 12 weeks by H and E staining based microscopic method	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID465485	Mutagenic activity in Salmonella Typhimurium TA97a assessed as increase in number of revertants at 100 ug/plate by Ames test presence of S9 fraction (Rvb=154+/-18)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1545089	Antiobesity activity in HFD-induced obese C57BL/6N mouse model assessed as decrease in visceral fat mass at 50 mg/kg, po administered once daily for 12 weeks	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID1446877	Antiviral activity against HCV pseudoparticle harboring HCV envelope protein E1 and E2 assessed as inhibition of pseudoparticle entry into human Huh7 cells at 1 uM measured after 3 days by Bright-Glo luciferase reporter gene assay relative to control	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Design, synthesis and biological evaluation of gentiopicroside derivatives as potential antiviral inhibitors.
AID465505	Mutagenic activity in Salmonella Typhimurium TA102 assessed as increase in number of revertants at 100 ug/plate by Ames test presence of S9 fraction (Rvb=369+/-34)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1545077	Downregulation of LPL mRNA expression in mouse 3T3L1 cells up to 10 uM incubated for 8 days followed by compound wash out measured by RT-PCR method	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID465502	Mutagenic activity in Salmonella Typhimurium TA102 assessed as increase in number of revertants at 40 ug/plate by Ames test presence of S9 fraction (Rvb=369+/-34)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465366	Mutagenic activity in Salmonella typhimurium TA98 assessed as increase in number of revertants at 40 ug/plate by Ames test absence of S9 fraction (Rvb=22+/- 4)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465482	Mutagenic activity in Salmonella Typhimurium TA97a assessed as increase in number of revertants at 40 ug/plate by Ames test presence of S9 fraction (Rvb=154+/-18)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1545074	Inhibition of cell differentiation in mouse 3T3L1 cells assessed as reduction in pre-adipocyte differentiation into matured adipocytes at 5 uM incubated for 8 days followed by compound wash out measured by oil red O staining based method relative to contr	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID1545088	Antiobesity activity in HFD-induced obese C57BL/6N mouse model assessed as decrease in epididymal fat mass level at 50 mg/kg, po administered once daily for 12 weeks	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID465475	Mutagenic activity in Salmonella Typhimurium TA98 assessed as increase in number of revertants at 100 ug/plate by Ames test presence of S9 fraction (Rvb=34+/- 4)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1545086	Downregulation of SREBP-1c mRNA expression in mouse 3T3L1 cells up to 10 uM incubated for 8 days followed by compound wash out measured by RT-PCR method	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID1545081	Antiinflammatory activity in mouse 3T3L1 cells assessed as reduction in IL-6 mRNA expression up to 10 uM incubated for 8 days followed by compound wash out measured by RT-PCR method	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID465504	Mutagenic activity in Salmonella typhimurium TA102 assessed as increase in number of revertants at 80 ug/plate by Ames test presence of S9 fraction (Rvb=369+/-34)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465494	Mutagenic activity in Salmonella Typhimurium TA100 assessed as increase in number of revertants at 80 ug/plate by Ames test presence of S9 fraction (Rvb=124+/-13)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1545087	Antiobesity activity in HFD-induced obese C57BL/6N mouse model assessed as decrease in body weight at 50 mg/kg, po administered once daily for 12 weeks and measured every week for 12 weeks	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID465492	Mutagenic activity in Salmonella typhimurium TA100 assessed as increase in number of revertants at 40 ug/plate by Ames test presence of S9 fraction (Rvb=124+/-13)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465484	Mutagenic activity in Salmonella typhimurium TA97a assessed as increase in number of revertants at 80 ug/plate by Ames test presence of S9 fraction (Rvb=154+/-18)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465507	Cytotoxicity activity against CHO cells assessed as cell viability after 24 hrs by WST1 test	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465483	Mutagenic activity in Salmonella typhimurium TA97a assessed as increase in number of revertants at 60 ug/plate by Ames test presence of S9 fraction (Rvb=154+/-18)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1545080	Downregulation of DGAT2 mRNA expression in mouse 3T3L1 cells up to 10 uM incubated for 8 days followed by compound wash out measured by RT-PCR method	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID465490	Mutagenic activity in Salmonella Typhimurium TA100 assessed as increase in number of revertants at 100 ug/plate by Ames test absence of S9 fraction (Rvb=124+/-13)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465500	Mutagenic activity in Salmonella Typhimurium TA102 assessed as increase in number of revertants at 100 ug/plate by Ames test absence of S9 fraction (Rvb=290+/-10)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1545078	Downregulation of FABP4 mRNA expression in mouse 3T3L1 cells up to 10 uM incubated for 8 days followed by compound wash out measured by RT-PCR method	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID1545075	Downregulation of PPARgamma mRNA expression in mouse 3T3L1 cells up to 10 uM incubated for 8 days followed by compound wash out measured by RT-PCR method	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID465498	Mutagenic activity in Salmonella Typhimurium TA102 assessed as increase in number of revertants at 60 ug/plate by Ames test absence of S9 fraction (Rvb=290+/-10)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1545079	Anti-adipogenic activity in mouse 3T3L1 cells grown in differentiation media assessed as decrease in lipid accumulation incubated for 8 days by Oil Red O staining based method	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID465488	Mutagenic activity in Salmonella typhimurium TA100 assessed as increase in number of revertants at 60 ug/plate by Ames test absence of S9 fraction (Rvb=108+/-5)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465499	Mutagenic activity in Salmonella Typhimurium TA102 assessed as increase in number of revertants at 80 ug/plate by Ames test absence of S9 fraction (Rvb=290+/-10)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465477	Mutagenic activity in Salmonella Typhimurium TA97a assessed as increase in number of revertants at 40 ug/plate by Ames test absence of S9 fraction (Rvb=146+/- 8)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465478	Mutagenic activity in Salmonella typhimurium TA97a assessed as increase in number of revertants at 60 ug/plate by Ames test absence of S9 fraction (Rvb=146+/- 8)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID465472	Mutagenic activity in Salmonella typhimurium TA98 assessed as increase in number of revertants at 40 ug/plate by Ames test presence of S9 fraction (Rvb=34+/- 4)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1545084	Downregulation of SCD1 mRNA expression in mouse 3T3L1 cells up to 10 uM incubated for 8 days followed by compound wash out measured by RT-PCR method	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID465474	Mutagenic activity in Salmonella Typhimurium TA98 assessed as increase in number of revertants at 80 ug/plate by Ames test presence of S9 fraction (Rvb=34+/- 4)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1545073	Anti-adipogenic activity in mouse 3T3L1 cells grown in differentiation media assessed as decrease in lipid accumulation up to 10 uM incubated for 8 days by Oil Red O staining based method	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID1545083	Antiinflammatory activity in mouse 3T3L1 cells assessed as reduction in NFkappaB1 mRNA expression level up to 10 uM incubated for 8 days followed by compound wash out measured by RT-PCR method	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
AID1545076	Downregulation of C/EBPalpha mRNA expression in mouse 3T3L1 cells up to 10 uM incubated for 8 days followed by compound wash out measured by RT-PCR method	2019	Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14	Gentiopicroside isolated from Gentiana scabra Bge. inhibits adipogenesis in 3T3-L1 cells and reduces body weight in diet-induced obese mice.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	9 (5.29)	18.7374
1990's	5 (2.94)	18.2507
2000's	28 (16.47)	29.6817
2010's	91 (53.53)	24.3611
2020's	37 (21.76)	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	0 (0.00%)	5.53%
Reviews	3 (1.72%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	171 (98.28%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	2.21	1	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
choline [no description available]	2.1	1	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	2.41	1	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	2.41	1	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.11	1	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
2,4-dichlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic Acid: An herbicide with irritant effects on the eye and the gastrointestinal system.. 2,4-D : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2 and 4 are substituted by chlorines.	2.07	1	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
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.	2.05	1	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
berberine [no description available]	6.99	1	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
leflunomide Leflunomide: An isoxazole derivative that inhibits dihydroorotate dehydrogenase, the fourth enzyme in the pyrimidine biosynthetic pathway. It is used an immunosuppressive agent in the treatment of RHEUMATOID ARTHRITIS and PSORIATIC ARTHRITIS.. leflunomide : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-methyl-1,2-oxazole-4-carboxylic acid with the anilino group of 4-(trifluoromethyl)aniline. The prodrug of teriflunomide.	7.31	1	(trifluoromethyl)benzenes; isoxazoles; monocarboxylic acid amide	antineoplastic agent; antiparasitic agent; EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; hepatotoxic agent; immunosuppressive agent; non-steroidal anti-inflammatory drug; prodrug; pyrimidine synthesis inhibitor; tyrosine kinase inhibitor
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.	2.41	1	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	2.07	1	diarylmethane
pyridinolcarbamate Pyridinolcarbamate: A drug that has been given by mouth in the treatment of atherosclerosis and other vascular disorders, hyperlipidemias, and thrombo-embolic disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1408)	2.41	1	pyridines
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.	2.05	1	mitomycin	alkylating agent; antineoplastic agent
corticosterone [no description available]	7.21	1	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
reserpine Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.. reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.	7.1	1	alkaloid ester; methyl ester; yohimban alkaloid	adrenergic uptake inhibitor; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; first generation antipsychotic; plant metabolite; xenobiotic
pilocarpine Pilocarpine: A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.. (+)-pilocarpine : The (+)-enantiomer of pilocarpine.	2.6	1	pilocarpine	antiglaucoma drug
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.	2.78	3	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	2.1	1	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	7.17	1	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
taurocholic acid Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	2.11	1	amino sulfonic acid; bile acid taurine conjugate	human metabolite
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	1.99	1	xanthene
2,4,7-trinitrofluorenone 2,4,7-trinitrofluorenone: structure	2.05	1
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.13	1	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
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.	7.41	1	1,4-benzoquinones	adjuvant; anti-inflammatory agent; antidepressant; antineoplastic agent; antioxidant; cardioprotective agent; plant metabolite
oleanolic acid [no description available]	2.76	3	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
cellobiose beta-cellobiose : A cellobiose with beta configuration at the reducing-end glucose residue.	7.13	1	cellobiose	epitope
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.	2.08	1	dialdehyde	biomarker
1-naphthylisothiocyanate 1-Naphthylisothiocyanate: A tool for the study of liver damage which causes bile stasis and hyperbilirubinemia acutely and bile duct hyperplasia and biliary cirrhosis chronically, with changes in hepatocyte function. It may cause skin and kidney damage.	2.55	2	isothiocyanate	insecticide
paeonol paeonol: structure	2.41	1	methoxybenzenes; phenols	metabolite
glycyrrhizic acid glycyrrhizinic acid : A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.	2.46	2	enone; glucosiduronic acid; pentacyclic triterpenoid; tricarboxylic acid; triterpenoid saponin	EC 3.4.21.5 (thrombin) inhibitor; plant metabolite
palmatine burasaine: structure in first source	6.99	1	berberine alkaloid; organic heterotetracyclic compound	plant metabolite
trimetazidine Trimetazidine: A vasodilator used in angina of effort or ischemic heart disease.	7.6	1	aromatic amine
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	7.05	1	D-galactosamine; primary amino compound	toxin
silver nitrate Silver Nitrate: A silver salt with powerful germicidal activity. It has been used topically to prevent OPHTHALMIA NEONATORUM.	2.05	1	inorganic nitrate salt; silver salt	astringent
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.	2.07	1	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
acridine half-mustard acridine half-mustard: RN given refers to parent cpd. acridine half-mustard : A member of the class of aminoacridines that is acridine which is substituted by a methoxy group at position 2, chlorine at position 6, and a {3-[(2-chloroethyl)amino]propyl}amino group at position 9.	2.05	1	aminoacridines; aromatic ether; organochlorine compound; secondary amino compound	mutagen
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.	2.13	1	benzenes; phenyl acetates
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.04	1	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
sodium azide Sodium Azide: A cytochrome oxidase inhibitor which is a nitridizing agent and an inhibitor of terminal oxidation. (From Merck Index, 12th ed). sodium azide : The sodium salt of hydrogen azide (hydrazoic acid).	2.05	1	inorganic sodium salt	antibacterial agent; explosive; mitochondrial respiratory-chain inhibitor; mutagen
thidiazuron [no description available]	2.05	1	ureas
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.	7.6	1	imidazoquinoline	antineoplastic agent; interferon inducer
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.	6.22	44	D-glucopyranose	epitope; mouse metabolite
baicalin [no description available]	2.74	3	dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative	antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug
oseltamivir Oseltamivir: An acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits NEURAMINIDASE.. oseltamivir : A cyclohexenecarboxylate ester that is the ethyl ester of oseltamivir acid. An antiviral prodrug (it is hydrolysed to the active free carboxylic acid in the liver), it is used to slow the spread of influenza.	2.15	1	acetamides; amino acid ester; cyclohexenecarboxylate ester; primary amino compound	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; environmental contaminant; prodrug; xenobiotic
isocoumarins Isocoumarins: Compounds that differ from COUMARINS in having the positions of the ring and ketone oxygens reversed so the keto oxygen is at the 1-position of the molecule.. isocoumarin : The simplest member of the class of isocoumarins that is 1H-isochromene which is substituted by an oxo group at position 1.	2.11	1	isocoumarins
echinocystic acid [no description available]	2.15	1	triterpenoid
loganin [no description available]	2.52	2	beta-D-glucoside; cyclopentapyran; enoate ester; iridoid monoterpenoid; methyl ester; monosaccharide derivative; secondary alcohol	anti-inflammatory agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; EC 3.4.23.46 (memapsin 2) inhibitor; neuroprotective agent; plant metabolite
loganic acid loganic acid: structure. loganic acid : A cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid substituted at positions 1, 6 and 7 by beta-D-glucosyloxy, hydroxy and methyl groups respectively	4.12	14	alpha,beta-unsaturated monocarboxylic acid; cyclopentapyran; glucoside	plant metabolite
geniposide [no description available]	2.81	3	terpene glycoside
homoorientin homoorientin: isolated from Swertia japonica; structure given in first source	3.12	5	flavone C-glycoside; tetrahydroxyflavone	antineoplastic agent; radical scavenger
gastrodin gastrodin: the glucoside of 4-hydroxybenzyl alcohol (gastrodigenin); isolated from Gastrodia elata Blume;	2.6	1	glycoside
amarogentin amarogentin: secoiridoid glycoside. amarogentin : A secoiridoid glycoside that consists of (4aS,5R,6R)-5-ethenyl-6-hydroxy-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one having a 2-O-[(3,3',5-trihydroxybiphenyl-2-yl)carbonyl]-beta-D-glucopyranosyl group attached at position 6 via a glycosidic linkage.	2.81	3	monosaccharide derivative; secoiridoid glycoside	EC 5.99.1.2 (DNA topoisomerase) inhibitor; metabolite
methotrexate [no description available]	7.31	1	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
sweroside [no description available]	4.73	27	glycoside
isovitexin [no description available]	2.44	2	C-glycosyl compound; trihydroxyflavone	EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
sb 203580 [no description available]	2.21	1	imidazoles; monofluorobenzenes; pyridines; sulfoxide	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector; Hsp90 inhibitor; neuroprotective agent
erythrocentaurin erythrocentaurin: isolated from Centaurium umbellatum Gilib, Enicostemma hyssopifolium & Swertia lawii; structure	2.11	1
gentianine gentianine: from Gentiana macrophylla	2	1	lactone; pyranopyridine; pyridine alkaloid
lithium chloride Lithium Chloride: A salt of lithium that has been used experimentally as an immunomodulator.. lithium chloride : A metal chloride salt with a Li(+) counterion.	2.6	1	inorganic chloride; lithium salt	antimanic drug; geroprotector
genipin [no description available]	2.11	1	iridoid monoterpenoid	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cross-linking reagent; hepatotoxic agent; uncoupling protein inhibitor
naringin [no description available]	2.07	1	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
swertiamarin swertiamarin: seco-iridoid glucoside from Swertia japonica;	6.1	37	glycoside
n-formylmethionine leucyl-phenylalanine N-Formylmethionine Leucyl-Phenylalanine: A formylated tripeptide originally isolated from bacterial filtrates that is positively chemotactic to polymorphonuclear leucocytes, and causes them to release lysosomal enzymes and become metabolically activated.. N-formyl-L-methionyl-L-leucyl-L-phenylalanine : A tripeptide composed of L-Met, L-Leu and L-Phe in a linear sequence with a formyl group at the amino terminus. It acts as a potent inducer of leucocyte chemotaxis and macrophage activator as well as a ligand for the FPR receptor.	2.07	1	tripeptide
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	2.52	2	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
tacrolimus Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.	2.41	1	macrolide lactam	bacterial metabolite; immunosuppressive agent
iridoids Iridoids: A type of MONOTERPENES, derived from geraniol. They have the general form of cyclopentanopyran, but in some cases, one of the rings is broken as in the case of secoiridoid. They are different from the similarly named iridals (TRITERPENES).	11.59	63
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	2.13	1	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
glycosides [no description available]	5.02	13
gw9662 2-chloro-5-nitrobenzanilide: pretreatment of peroxisome proliferator activated receptors with GW9662 results in the irreversible loss of ligand binding	2.17	1	benzamides
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.	2.15	1	cinnamate ester; tannin	food component; plant metabolite
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.49	2
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.48	2
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	7.31	1
2,4-dinitrophenylhydrazine 2,4-dinitrophenylhydrazine: structure. 2,4-dinitrophenylhydrazine : A C-nitro compound that is phenylhydrazine substituted at the 2- and 4-positions by nitro groups.	7.11	1	C-nitro compound; phenylhydrazines	reagent
bilirubin [no description available]	2.49	2	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.	2.59	2	prostaglandins E	human metabolite; mouse metabolite; oxytocic
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.	2.44	2	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	3.29	6	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
kaempferol [no description available]	2.07	1	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
alpha-linolenic acid linolenic acid : A two-membered subclass of octadecatrienoic acid comprising the (9Z,12Z,15Z)- and (6Z,9Z,12Z)-isomers. Linolenic acids are nutrients essential to the formation of prostaglandins and are also used in making paints and synthetic resins.. linolenate : A polyunsaturated fatty acid anion obtained by deprotonation of the carboxy group of either alpha- or gamma-linolenic acid.	2.13	1	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
jasmonic acid jasmonic acid: a derivative of alpha-linolenic acid that has a role in plant response to herbivory analogous to the role of prostanoids in inflammation in mammals;. jasmonic acid : An oxo monocarboxylic acid that is (3-oxocyclopentyl)acetic acid substituted by a (2Z)-pent-2-en-1-yl group at position 2 of the cyclopentane ring.	2.13	1	oxo monocarboxylic acid	jasmonates; plant metabolite
isogentisin isogentisin: found in plants such as Guttiferae & Gentianaceae.; structure. isogentisin : A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1 and 3 and a methoxy group at position 7.	2.11	1	aromatic ether; polyphenol; xanthones	EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
mangiferin shamimin: isolated from the leaves of Bombax ceiba; structure in first source	8.13	5	C-glycosyl compound; xanthones	anti-inflammatory agent; antioxidant; hypoglycemic agent; plant metabolite
norswertianolin norswertianolin: RN given refers to beta-D-isomer; from Swertia randaiensis; shows depressant acitivity on cental nervous system. norswertianolin : A beta-D-glucoside that is bellidin in which a beta-D-glucopyranosyl residue is attached at position O-8. A natural product found particularly in Gentiana campestris and Gentiana germanica.	2.05	1	beta-D-glucoside; xanthones	EC 3.1.1.7 (acetylcholinesterase) inhibitor; 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.	6.99	1	dihydroxyflavone; monomethoxyflavone	angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	7.07	1	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
clobetasol Clobetasol: A derivative of PREDNISOLONE with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than FLUOCINONIDE, it is used topically in treatment of PSORIASIS but may cause marked adrenocortical suppression.. clobetasol : A 3-oxo-Delta(1),Delta(4)-steroid that is 16beta-methylpregna-1,4-diene-3,20-dione bearing hydroxy groups at the 11beta and 17alpha positions, fluorine at position 9, and a chlorine substituent at position 21. It is used as its 17alpha-propionate ester to treat various skin disorders, including exzema and psoriasis.	2.41	1	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; chlorinated steroid; fluorinated steroid; glucocorticoid; tertiary alpha-hydroxy ketone	anti-inflammatory drug; SMO receptor agonist
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	2.6	1	carbon group element atom; elemental lead; metal atom	neurotoxin
bay 11-7082 (E)-3-tosylacrylonitrile : A nitrile that is acrylonitrile in which the hydrogen located beta,trans to the cyano group is replaced by a tosyl group. It is an inhibitor of cytokine-induced IkappaB-alpha phosphorylation in cells.	2.21	1	nitrile; sulfone	apoptosis inducer; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; non-steroidal anti-inflammatory drug; platelet aggregation inhibitor
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	2.13	1	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
picroside i picroside I: RN given for (1aS-(1aalpha,1bbeta,2beta(E),5abeta,6beta,6aalpha))-isomer; hepatoprotective agent; structure in first source	2.6	1
ro 25-6981 Ro 25-6981: blocks NMDA receptors containg NR2B subunit; structure in first source. Ro 25-6981 : A member of the class of piperidines that is 4-benzylpiperidine substituted by a 3-hydroxy-3-(4-hydroxyphenyl)-2-methylpropyl group at position 1 (the 1R,2S-stereoisomer). It is a potent antagonist of the GluN2B subunit of the N-methyl-D-aspartate (NMDA) receptor.	2.1	1	benzenes; phenols; piperidines; secondary alcohol; tertiary amino compound	anticonvulsant; antidepressant; neuroprotective agent; NMDA receptor antagonist
roburic acid roburic acid : A tetracyclic triterpenoid with formula C30H40O2 that is isolated from the roots of Gentiana dahurica and Gentiana macrophylla.	2.6	1	monocarboxylic acid; olefinic compound; tetracyclic triterpenoid	plant metabolite
lyoniside lyoniside: see also eleutherosides & syringin for eleutheroside B: 118-34-3; RN given refers to (3beta)-isomer	2.48	2
gastrins Gastrins: A family of gastrointestinal peptide hormones that excite the secretion of GASTRIC JUICE. They may also occur in the central nervous system where they are presumed to be neurotransmitters.	2.11	1
chitosan [no description available]	7.6	1
methyl jasmonate [no description available]	7.13	1
piperidines Piperidines: A family of hexahydropyridines.	2.1	1
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.	2.31	1
picroside ii picroside II: RN given for (1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6abeta))-isomer; structure in first source	2.6	1

Condition	Relationship Strength	Studies
Innate Inflammatory Response [description not available]	3.66	8
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	3.66	8
Grippe [description not available]	2.15	1
Influenza, Human An acute viral infection in humans involving the respiratory tract. It is marked by inflammation of the NASAL MUCOSA; the PHARYNX; and conjunctiva, and by headache and severe, often generalized, myalgia.	2.15	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	7.21	1
Gouty Arthritis [description not available]	7.41	1
Arthritis, Gouty Arthritis, especially of the great toe, as a result of gout. Acute gouty arthritis often is precipitated by trauma, infection, surgery, etc. The initial attacks are usually monoarticular but later attacks are often polyarticular. Acute and chronic gouty arthritis are associated with accumulation of MONOSODIUM URATE in and around affected joints.	2.41	1
Age-Related Osteoporosis [description not available]	2.31	1
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	2.31	1
Adjuvant Arthritis [description not available]	2.9	3
Plica Syndrome [description not available]	2.41	1
Synovitis Inflammation of the SYNOVIAL MEMBRANE.	2.41	1
Alloxan Diabetes [description not available]	2.41	1
Diabetes Mellitus, Adult-Onset [description not available]	2.41	1
Cirrhosis [description not available]	2.41	1
Cardiac Failure [description not available]	2.41	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	2.41	1
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	7.41	1
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	2.41	1
Dermatitis Any inflammation of the skin.	7.9	2
Acute Confusional Senile Dementia [description not available]	2.6	1
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	2.6	1
Anasarca [description not available]	2.6	1
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.6	1
Injury, Myocardial Reperfusion [description not available]	2.6	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.89	10
Palmoplantaris Pustulosis [description not available]	2.6	1
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.	2.6	1
Cardiovascular Stroke [description not available]	2.6	1
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	7.6	1
Dehydration The condition that results from excessive loss of water from a living organism.	2.6	1
Rheumatoid Arthritis [description not available]	2.66	2
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	2.66	2
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	2.84	3
Diabetic Glomerulosclerosis [description not available]	2.25	1
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	2.25	1
Liver Dysfunction [description not available]	2.25	1
Liver Diseases Pathological processes of the LIVER.	2.25	1
Cancer of Cervix [description not available]	2.31	1
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	2.31	1
Polyarthritis [description not available]	2.31	1
Arthritis Acute or chronic inflammation of JOINTS.	2.31	1
Cancer of Stomach [description not available]	2.25	1
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.25	1
Gastritis Inflammation of the GASTRIC MUCOSA, a lesion observed in a number of unrelated disorders.	7.31	1
Alcoholic Liver Diseases [description not available]	2.31	1
Liver Diseases, Alcoholic Liver diseases associated with ALCOHOLISM. It usually refers to the coexistence of two or more subentities, i.e., ALCOHOLIC FATTY LIVER; ALCOHOLIC HEPATITIS; and ALCOHOLIC CIRRHOSIS.	2.31	1
Tetraploid [description not available]	2.31	1
Asthma, Bronchial [description not available]	2.31	1
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	7.31	1
Gastric Ulcer [description not available]	2.17	1
Stomach Ulcer Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	2.17	1
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	2.17	1
Alveolitis, Fibrosing [description not available]	2.17	1
Pneumonia Infection of the lung often accompanied by inflammation.	2.17	1
Pulmonary Fibrosis A process in which normal lung tissues are progressively replaced by FIBROBLASTS and COLLAGEN causing an irreversible loss of the ability to transfer oxygen into the bloodstream via PULMONARY ALVEOLI. Patients show progressive DYSPNEA finally resulting in death.	7.17	1
Alcoholic Fatty Liver [description not available]	2.17	1
Acute Liver Injury, Drug-Induced [description not available]	3.21	5
Bile Duct Obstruction [description not available]	2.55	2
Cholestasis Impairment of bile flow due to obstruction in small bile ducts (INTRAHEPATIC CHOLESTASIS) or obstruction in large bile ducts (EXTRAHEPATIC CHOLESTASIS).	2.55	2
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	3.21	5
Dyslipidemia [description not available]	2.17	1
Asymmetric Diabetic Proximal Motor Neuropathy [description not available]	2.17	1
Allodynia [description not available]	2.53	2
Diabetic Neuropathies Peripheral, autonomic, and cranial nerve disorders that are associated with DIABETES MELLITUS. These conditions usually result from diabetic microvascular injury involving small blood vessels that supply nerves (VASA NERVORUM). Relatively common conditions which may be associated with diabetic neuropathy include third nerve palsy (see OCULOMOTOR NERVE DISEASES); MONONEUROPATHY; mononeuropathy multiplex; diabetic amyotrophy; a painful POLYNEUROPATHY; autonomic neuropathy; and thoracoabdominal neuropathy. (From Adams et al., Principles of Neurology, 6th ed, p1325)	2.17	1
Dyslipidemias Abnormalities in the serum levels of LIPIDS, including overproduction or deficiency. Abnormal serum lipid profiles may include high total CHOLESTEROL, high TRIGLYCERIDES, low HIGH DENSITY LIPOPROTEIN CHOLESTEROL, and elevated LOW DENSITY LIPOPROTEIN CHOLESTEROL.	2.17	1
Dermatophytoses [description not available]	2.21	1
Tinea Fungal infection of keratinized tissues such as hair, skin and nails. The main causative fungi include MICROSPORUM; TRICHOPHYTON; and EPIDERMOPHYTON.	2.21	1
Pain, Chronic [description not available]	2.1	1
Ache [description not available]	2.47	2
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.47	2
Chronic Pain Aching sensation that persists for more than a few months. It may or may not be associated with trauma or disease, and may persist after the initial injury has healed. Its localization, character, and timing are more vague than with acute pain.	2.1	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.76	3
Acute Edematous Pancreatitis [description not available]	2.11	1
Pancreatitis INFLAMMATION of the PANCREAS. Pancreatitis is classified as acute unless there are computed tomographic or endoscopic retrograde cholangiopancreatographic findings of CHRONIC PANCREATITIS (International Symposium on Acute Pancreatitis, Atlanta, 1992). The two most common forms of acute pancreatitis are ALCOHOLIC PANCREATITIS and gallstone pancreatitis.	7.11	1
Cholera Infantum [description not available]	2.11	1
Lesion of Sciatic Nerve [description not available]	2.13	1
Nerve Pain [description not available]	2.13	1
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.13	1
Hepatocellular Carcinoma [description not available]	2.13	1
Cancer of Liver [description not available]	2.13	1
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.13	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.13	1
Bowel Diseases, Inflammatory [description not available]	2.13	1
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	7.13	1
Inflammatory Bowel Diseases Chronic, non-specific inflammation of the GASTROINTESTINAL TRACT. Etiology may be genetic or environmental. This term includes CROHN DISEASE and ULCERATIVE COLITIS.	2.13	1
Hepatic Failure [description not available]	7.05	1
Liver Failure Severe inability of the LIVER to perform its normal metabolic functions, as evidenced by severe JAUNDICE and abnormal serum levels of AMMONIA; BILIRUBIN; ALKALINE PHOSPHATASE; ASPARTATE AMINOTRANSFERASE; LACTATE DEHYDROGENASES; and albumin/globulin ratio. (Blakiston's Gould Medical Dictionary, 4th ed)	2.05	1
Disease, Pulmonary [description not available]	2.06	1
Lung Diseases Pathological processes involving any part of the LUNG.	2.06	1
Injury, Ischemia-Reperfusion [description not available]	2.07	1
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	2.07	1
Chronic Illness [description not available]	2.04	1
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2.04	1
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	1.98	1
Hepatitis, Animal INFLAMMATION of the LIVER in non-human animals.	1.98	1
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	2	1

gentiopicroside

Description

Cross-References

Synonyms (48)

Research Excerpts

Overview

Effects

Actions

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Drug Classes (1)

Protein Targets (3)

Potency Measurements

Bioassays (69)

Research

Studies (170)

Market Indicators

Research Demand Index: 37.13

Study Types

gentiopicroside

Description

Related Flora

Cross-References

Synonyms (48)

Research Excerpts

Overview

Effects

Actions

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Drug Classes (1)

Protein Targets (3)

Potency Measurements

Bioassays (69)

Research

Studies (170)

Market Indicators

Research Demand Index: 37.13

Study Types

Related Drugs (100)

Related Conditions (97)