medicarpin profile

(-)-medicarpin : The (-)-enantiomer of medicarpin. [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]

ID Source	ID
PubMed CID	336327
CHEMBL ID	238845
CHEBI ID	100
SCHEMBL ID	72476
MeSH ID	M0136807

Synonym
6h-benzofuro[3,2-c][1]benzopyran-3-ol, 6a,11a-dihydro-9-methoxy-, cis-
NCI60_003118
medicarpin, (-)-
6h-benzofuro[3, 6a,11a-dihydro-9-methoxy-, cis-
nsc-350085
NSC350085 ,
(l)-de-o-methylhomopterocarpan
6h-benzofuro[3, 6a,11a-dihydro-9-methoxy-, (6ar-cis)-
(-)-3-hydroxy-9-methoxypterocarpan
demethylhomopterocarpin
l-3-hydroxy-9-methoxypterocarpan
(-)-demethylhomopterocarpin
MEGXP0_001319
NCGC00180373-01
ACON1_001568
CHEBI:100 ,
33983-40-3
(6ar,11ar)-9-methoxy-6a,11a-dihydro-6h-[1]benzofuro[3,2-c]chromen-3-ol
32383-76-9
medicarpin ,
(-)-medicarpin
3-hydroxy-9-methoxypterocarpan
(-) medicarpin
3-hydroxy-9-methoxypterocarpan, (-)
(6ar,11ar)-9-methoxy-6a,11a-dihydro-6h-benzofuro[3,2-c]chromen-3-ol
6h-benzofuro[3, 2-c][1]benzopyran-3-ol, 6a,11a-dihydro-9-methoxy-, (6ar-cis)-
smr000470945
MLS000697611
(6ar,11ar)-medicarpin
CHEMBL238845 ,
BRD-K20359375-001-01-6
LMPK12070028
HMS2270J20
6h-benzofuro(3,2-c)(1)benzopyran-3-ol, 6a,11a-dihydro-9-methoxy-, cis-
unii-6tx086i6ig
6a,11a-dihydro-9-methoxy-6h-benzofuro(3,2-c)(1)benzopyran-3-ol
6tx086i6ig ,
nsc 350085
SCHEMBL72476
(6ar,11ar)-6a,11a-dihydro-9-methoxy-6h-benzofuro(3,2-c)(1)benzopyran-3-ol
medicarpin [mi]
9-methoxy-6a,11a-dihydro-6h-[1]benzofuro[3,2-c]chromen-3-ol, cis-
6h-benzofuro[3,2-c][1]benzopyran-3-ol, 6a,11a-dihydro-9-methoxy-, cis-(-)-
NSRJSISNDPOJOP-BBRMVZONSA-N
6h-benzofuro[3,2-c][1]benzopyran-3-ol, 6a,11a-dihydro-9-methoxy-, (6ar-cis)-
mfcd00161527
AKOS032948389
Q56036865
(4-ethoxyphenyl)-oxo-acetonitrile
HY-N3308
CS-0023866
MS-23819
6h-benzofuro[3,2-c][1]benzopyran-3-ol, 6a,11a-dihydro-9-methoxy-,(6ar,11ar)-
bdbm50535253
(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0?,?.0??,??]heptadeca-2,4,6,11,13,15-hexaen-5-ol
DTXSID301026587
6h-benzofuro[3,2-c][1]benzopyran-3-ol,6a,11a-dihydro-9-methoxy-,(6ar,11ar)-rel-
(6ar,11ar)-9-methoxy-6a,11a-dihydro-6h-(1)benzofuro(3,2-c)chromen-3-ol
rel-(6ar,11ar)-9-methoxy-6a,11a-dihydro-6h-benzofuro[3,2-c]chromen-3-ol

Excerpt	Reference	Relevance
"Medicarpin is a natural pterocarpan-type phytoalexin widely distributed in many traditional Chinese medicines, such as Astragali Radix. "	( Systems pharmacology approach uncovers the therapeutic mechanism of medicarpin against scopolamine-induced memory loss. Cai, C; Ding, B; Fang, J; Fang, S; Guo, P; Ke, H; Li, D; Liao, Y; Wang, Q; Wu, Q, 2021)	2.3
"Medicarpin is a bioactive pterocarpan that has been attracting increasing attention in recent years. "	( Metabolites of Medicarpin and Their Distributions in Rats. Cai, SQ; Ji, R; Li, T; Li, YL; Liu, GX; Shang, MY; Wang, HY; Xu, F, 2019)	2.31

Excerpt	Reference	Relevance
"(+)-Medicarpin has been synthesized asymmetrically for the first time in a linear scalable process with an overall yield of 11%. "	( Total Synthesis of (+)-Medicarpin. Cheng, CH; Horng, LY; Hsieh, MT; Hsu, PL; Lee, KH; Sung, HC; Wu, RT; Xin, G; Yang, X; Zhao, Y, 2017)	1.32

Excerpt	Reference	Relevance
"Medicarpin treatment ameliorated depressive-like behaviors in CUMS-induced mice by modulating LXRβ level."	( Medicarpin Improves Depressive-Like Behaviors in a Chronic Unpredictable Mild Stress-Induced Mouse Model of Depression by Upregulating Liver X Receptor β Expression in the Amygdala. He, X; Li, Y; Liu, X; Zhang, J; Zhou, G; Zhou, Q, 2022)	2.89
"Medicarpin treatment to OVx mice maintained parameters of trabecular microarchitecure."	( Medicarpin inhibits osteoclastogenesis and has nonestrogenic bone conserving effect in ovariectomized mice. Bhargavan, B; Brazier, M; Chattopadhyay, N; Gautam, AK; Goel, A; Kumar, A; Maurya, R; Mentaverri, R; Pollet, C; Saravanan, S; Singh, D; Singh, N; Srivastava, K; Trivedi, R; Tyagi, AM; Yadav, DK, 2010)	2.52
"Treatment with medicarpin or millepurpan triggered apoptosis in sensitive as well as multidrug resistant P388 cells."	( Medicarpin and millepurpan, two flavonoids isolated from Medicago sativa, induce apoptosis and overcome multidrug resistance in leukemia P388 cells. Bertin, E; El btaouri, H; Gatouillat, G; Lavaud, C; Madoulet, C; Magid, AA; Morjani, H, 2015)	2.2

Excerpt	Reference	Relevance
" In pharmacokinetic studies, Med exhibited oral bioavailability of 22."	( Medicarpin, a legume phytoalexin, stimulates osteoblast differentiation and promotes peak bone mass achievement in rats: evidence for estrogen receptor β-mediated osteogenic action of medicarpin. Bhargavan, B; Chakravarti, B; Chattopadhyay, N; Dixit, M; Dwivedi, SD; Gautam, AK; Goel, A; Jain, GK; Kumar, A; Manickavasagam, L; Maurya, R; Mishra, JS; Pandey, R; Ramachandran, R; Sanyal, S; Singh, D; Trivedi, A, 2012)	1.82

Excerpt	Reference	Relevance
" In pharmacokinetic studies, Med exhibited oral bioavailability of 22."	( Medicarpin, a legume phytoalexin, stimulates osteoblast differentiation and promotes peak bone mass achievement in rats: evidence for estrogen receptor β-mediated osteogenic action of medicarpin. Bhargavan, B; Chakravarti, B; Chattopadhyay, N; Dixit, M; Dwivedi, SD; Gautam, AK; Goel, A; Jain, GK; Kumar, A; Manickavasagam, L; Maurya, R; Mishra, JS; Pandey, R; Ramachandran, R; Sanyal, S; Singh, D; Trivedi, A, 2012)	1.82
" Its oral bioavailability was 17."	( LC-ESI-MS/MS method for bioanalytical determination of osteogenic phytoalexin, medicarpin, and its application to preliminary pharmacokinetic studies in rats. Challagundla, M; Goel, A; Raghuvanshi, A; Raju, KS; Taneja, I; Wahajuddin, M, 2015)	0.64
" The oral bioavailability of medicarpin was found to be low with low systemic levels."	( Bioavailability, tissue distribution and excretion studies of a potential anti-osteoporotic agent, medicarpin, in female rats using validated LC-MS/MS method. Awasthi, P; Goel, A; Raghuvanshi, A; Rama Raju, KS; Rashid, M; Singh, S; Singh, SP; Taneja, I; Wahajuddin, M, 2020)	1.07

Role	Description
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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
medicarpin	A member of the class of pterocarpans that is 3-hydroxyptercarpan with a methoxy substituent at position 9.
[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
vestitol and sativan biosynthesis	0	8
medicarpin conjugates interconversion	0	15
superpathway of pterocarpan biosynthesis (via formononetin)	0	31
(-)-medicarpin biosynthesis	0	10
superpathway of formononetin derivative biosynthesis	0	31
pterocarpan phytoalexins modification (maackiain, medicarpin, pisatin, phaseollin)	4	24
medicarpin conjugates interconversion	0	17
(-)-medicarpin biosynthesis	2	10
superpathway of pterocarpan biosynthesis (via formononetin)	3	34
superpathway of formononetin derivative biosynthesis	2	34
Medicarpin biosynthesis	0	12

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Nrf2	Homo sapiens (human)	Potency	35.4813	0.0920	8.2222	23.1093	AID624171
ClpP	Bacillus subtilis	Potency	0.7079	1.9953	22.6730	39.8107	AID651965
geminin	Homo sapiens (human)	Potency	1.1582	0.0046	11.3741	33.4983	AID624297
TAR DNA-binding protein 43	Homo sapiens (human)	Potency	35.4813	1.7783	16.2081	35.4813	AID652104
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Proteasome subunit beta type-5	Homo sapiens (human)	IC50 (µMol)	100.0000	0.0005	0.9394	10.0000	AID1633148
[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)
Delta-type opioid receptor	Rattus norvegicus (Norway rat)	CD	13.7000	0.4300	4.6150	8.8000	AID334057
Quinone oxidoreductase	Mus musculus (house mouse)	CD	13.7000	0.2000	2.7421	9.8000	AID334057
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
proteolysis	Proteasome subunit beta type-5	Homo sapiens (human)
response to oxidative stress	Proteasome subunit beta type-5	Homo sapiens (human)
proteasome-mediated ubiquitin-dependent protein catabolic process	Proteasome subunit beta type-5	Homo sapiens (human)
negative regulation of protein phosphorylation	TAR DNA-binding protein 43	Homo sapiens (human)
mRNA processing	TAR DNA-binding protein 43	Homo sapiens (human)
RNA splicing	TAR DNA-binding protein 43	Homo sapiens (human)
negative regulation of gene expression	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of protein stability	TAR DNA-binding protein 43	Homo sapiens (human)
positive regulation of insulin secretion	TAR DNA-binding protein 43	Homo sapiens (human)
response to endoplasmic reticulum stress	TAR DNA-binding protein 43	Homo sapiens (human)
positive regulation of protein import into nucleus	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of circadian rhythm	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of apoptotic process	TAR DNA-binding protein 43	Homo sapiens (human)
negative regulation by host of viral transcription	TAR DNA-binding protein 43	Homo sapiens (human)
rhythmic process	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of cell cycle	TAR DNA-binding protein 43	Homo sapiens (human)
3'-UTR-mediated mRNA destabilization	TAR DNA-binding protein 43	Homo sapiens (human)
3'-UTR-mediated mRNA stabilization	TAR DNA-binding protein 43	Homo sapiens (human)
nuclear inner membrane organization	TAR DNA-binding protein 43	Homo sapiens (human)
amyloid fibril formation	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of gene expression	TAR DNA-binding protein 43	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
threonine-type endopeptidase activity	Proteasome subunit beta type-5	Homo sapiens (human)
protein binding	Proteasome subunit beta type-5	Homo sapiens (human)
peptidase activity	Proteasome subunit beta type-5	Homo sapiens (human)
endopeptidase activity	Proteasome subunit beta type-5	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	TAR DNA-binding protein 43	Homo sapiens (human)
DNA binding	TAR DNA-binding protein 43	Homo sapiens (human)
double-stranded DNA binding	TAR DNA-binding protein 43	Homo sapiens (human)
RNA binding	TAR DNA-binding protein 43	Homo sapiens (human)
mRNA 3'-UTR binding	TAR DNA-binding protein 43	Homo sapiens (human)
protein binding	TAR DNA-binding protein 43	Homo sapiens (human)
lipid binding	TAR DNA-binding protein 43	Homo sapiens (human)
identical protein binding	TAR DNA-binding protein 43	Homo sapiens (human)
pre-mRNA intronic binding	TAR DNA-binding protein 43	Homo sapiens (human)
molecular condensate scaffold activity	TAR DNA-binding protein 43	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
nucleus	Proteasome subunit beta type-5	Homo sapiens (human)
cytoplasm	Proteasome subunit beta type-5	Homo sapiens (human)
proteasome complex	Proteasome subunit beta type-5	Homo sapiens (human)
nucleus	Proteasome subunit beta type-5	Homo sapiens (human)
nucleoplasm	Proteasome subunit beta type-5	Homo sapiens (human)
centrosome	Proteasome subunit beta type-5	Homo sapiens (human)
cytosol	Proteasome subunit beta type-5	Homo sapiens (human)
extracellular exosome	Proteasome subunit beta type-5	Homo sapiens (human)
proteasome core complex	Proteasome subunit beta type-5	Homo sapiens (human)
proteasome core complex, beta-subunit complex	Proteasome subunit beta type-5	Homo sapiens (human)
cytosol	Proteasome subunit beta type-5	Homo sapiens (human)
intracellular non-membrane-bounded organelle	TAR DNA-binding protein 43	Homo sapiens (human)
nucleus	TAR DNA-binding protein 43	Homo sapiens (human)
nucleoplasm	TAR DNA-binding protein 43	Homo sapiens (human)
perichromatin fibrils	TAR DNA-binding protein 43	Homo sapiens (human)
mitochondrion	TAR DNA-binding protein 43	Homo sapiens (human)
cytoplasmic stress granule	TAR DNA-binding protein 43	Homo sapiens (human)
nuclear speck	TAR DNA-binding protein 43	Homo sapiens (human)
interchromatin granule	TAR DNA-binding protein 43	Homo sapiens (human)
nucleoplasm	TAR DNA-binding protein 43	Homo sapiens (human)
chromatin	TAR DNA-binding protein 43	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
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.
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.
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
AID1224817	Assays to identify small molecules inhibitory for eIF4E expression	2015	Chemistry & biology, Jul-23, Volume: 22, Issue:7	Internal Ribosome Entry Site-Based Bicistronic In Situ Reporter Assays for Discovery of Transcription-Targeted Lead Compounds.
AID1243357	Antioxidant activity assessed as reduction of Fe3+ to Fe2+ after 20 mins	2015	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18	Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L.
AID1243359	Cytotoxicity against rat PC12 cells assessed as cell viability at 75 uM after 24 hrs by MTT assay relative to control	2015	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18	Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L.
AID756490	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production after 24 hrs by Griess assay	2013	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 23, Issue:14	Inhibitory constituents of the heartwood of Dalbergia odorifera on nitric oxide production in RAW 264.7 macrophages.
AID1243358	Cytotoxicity against rat PC12 cells assessed as cell viability at 30 uM after 24 hrs by MTT assay	2015	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18	Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L.
AID1243356	Antioxidant activity assessed as ABTS radical scavenging activity after 6 mins	2015	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18	Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L.
AID1243360	Cytotoxicity against rat PC12 cells assessed as cell viability at 150 uM after 24 hrs by MTT assay relative to control	2015	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18	Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L.
AID756489	Cytotoxicity against mouse RAW264.7 cells by CCK assay	2013	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 23, Issue:14	Inhibitory constituents of the heartwood of Dalbergia odorifera on nitric oxide production in RAW 264.7 macrophages.
AID1432767	Enhancement of GLUT4 translocation at plasma membrane of rat L6 cells expressing pIRAP-mOrange at 10 uM after 30 mins by fluorescence assay relative to control	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Chemical constituents from Sophora tonkinensis and their glucose transporter 4 translocation activities.
AID334057	Induction of quinone reductase activity in mouse Hepa-1c1c7 cells assessed as drug level required to double enzyme activity after 48 hrs by MTT assay	1997	Journal of natural products, Sep, Volume: 60, Issue:9	Activity-guided isolation of constituents of Tephrosia purpurea with the potential to induce the phase II enzyme, quinone reductase.
AID1243355	Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins	2015	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18	Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L.
AID334058	Cytotoxicity against mouse Hepa-1c1c7 cells assessed as cell survival after 2 days by MTT assay	1997	Journal of natural products, Sep, Volume: 60, Issue:9	Activity-guided isolation of constituents of Tephrosia purpurea with the potential to induce the phase II enzyme, quinone reductase.
AID334059	Chemoprevention index, ratio of IC50 for mouse Hepa-1c1c7 cells to drug level required to double quinone reductase activity in mouse Hepa-1c1c7 cells	1997	Journal of natural products, Sep, Volume: 60, Issue:9	Activity-guided isolation of constituents of Tephrosia purpurea with the potential to induce the phase II enzyme, quinone reductase.
AID1243363	Neuroprotective activity against amyloid beta (25 to 35)-induced toxicity in rat PC12 cells assessed as increase in cell viability after 24 hrs by MTT assay	2015	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18	Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L.
AID1243361	Neuroprotective activity against amyloid beta (25 to 35)-induced toxicity in rat PC12 cells assessed as increase in cell viability at 30 uM after 24 hrs by MTT assay relative to control	2015	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18	Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L.
AID1633148	Inhibition of chymotrypsin-like activity of purified human erythrocyte 20S proteasome assessed as decrease in AMC hydrolysis using Suc-LLVY-AMC as substrate preincubated for 10 mins and measured by fluorescence based method	2019	European journal of medicinal chemistry, Apr-01, Volume: 167	Another look at phenolic compounds in cancer therapy the effect of polyphenols on ubiquitin-proteasome system.
AID1243362	Neuroprotective activity against amyloid beta (25 to 35)-induced toxicity in rat PC12 cells assessed as increase in cell viability at 75 uM after 24 hrs by MTT assay relative to control	2015	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18	Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	3 (4.00)	18.7374
1990's	9 (12.00)	18.2507
2000's	18 (24.00)	29.6817
2010's	33 (44.00)	24.3611
2020's	12 (16.00)	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	2 (2.63%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	74 (97.37%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
2-(3-pyridine)acetic acid 3-pyridylacetic acid : A monocarboxylic acid that is acetic acid substituted by a (pyridin-3-yl) group. It is a metabolite of nicotine and other tobacco alkaloids.	2.11	1	monocarboxylic acid; pyridines	human xenobiotic metabolite
ureidosuccinic acid ureidosuccinic acid: RN given refers to (DL)-isomer. N-carbamoylaspartic acid : An N-carbamoylamino acid that is aspartic acid with one of its amino hydrogens replaced by a carbamoyl group.	2.11	1	aspartic acid derivative; C4-dicarboxylic acid; N-carbamoyl-amino acid	Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite
arabinofuranosylcytosine triphosphate [no description available]	2.11	1	pyrimidine ribonucleoside monophosphate
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	7.66	2	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
aminoethylphosphonic acid Aminoethylphosphonic Acid: An organophosphorus compound isolated from human and animal tissues.. (2-aminoethyl)phosphonic acid : A phosphonic acid in which the hydrogen attached to the phosphorus of phosphonic acid is substituted by a 2-aminoethyl group.	2.11	1	phosphonic acids; primary amino compound; zwitterion	human metabolite; metabolite; mouse metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	3.31	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
gamma-guanidinobutyric acid gamma-guanidinobutyric acid: RN given refers to parent cpd. 4-guanidinobutyric acid : A monocarboxylic acid that is butanoic acid substituted by a guanidino group at position 4.. 4-guanidinobutanoate : A monocarboxylic acid anion that is the conjugate base of 4-guanidinobutanoic acid.. 4-guanidinobutanoic acid : The 4-guanidino derivative of butanoic acid.	2.11	1	guanidines; monocarboxylic acid; zwitterion	fungal metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
inositol Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.	2.11	1	cyclitol; hexol
pentachlorophenol PENTA: structure given in first source	2.11	1	aromatic fungicide; chlorophenol; organochlorine pesticide; pentachlorobenzenes	human xenobiotic metabolite
phenylalanine [no description available]	2.11	1	alpha-amino acid; aromatic amino acid	Daphnia magna metabolite
nsc-267703 [no description available]	2.11	1	anthracycline
n-acetyltryptophan N-acetyltryptophan : An N-acetylamino acid that is the N-acetyl derivative of tryptophan.	2.11	1	N-acetyl-amino acid; tryptophan derivative	metabolite
tyrphostin ag957 tyrphostin AG957: tyrosine kinase blocker; structure given in first source	2.11	1	aromatic amine
pimagedine pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.	2.08	1	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor
2-amino-4-phosphonobutyric acid 2-amino-4-phosphonobutyric acid: glutamate antagonist in locust muscle; structure; do not confuse with L-AP4, which is the propionic acid version	2.11	1
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.	2.11	1	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin
benzbromarone Benzbromarone: Uricosuric that acts by increasing uric acid clearance. It is used in the treatment of gout.. benzbromarone : 1-Benzofuran substituted at C-2 and C-3 by an ethyl group and a 3,5-dibromo-4-hydroxybenzoyl group respectively. An inhibitor of CYP2C9, it is used as an anti-gout medication.	2.11	1	1-benzofurans; aromatic ketone	uricosuric drug
benzylhydrochlorothiazide [no description available]	2.11	1	benzenes; benzothiadiazine; organochlorine compound; secondary amino compound; sulfonamide
eucalyptol [no description available]	2.11	1
amberlite cg 400 [no description available]	2.11	1	methyl ester; organic heteropentacyclic compound; yohimban alkaloid
benzophenone benzophenone : The simplest member of the class of benzophenones, being formaldehyde in which both hydrogens are replaced by phenyl groups.	2.1	1	benzophenones	photosensitizing agent; plant metabolite
stallimycin [no description available]	2.11	1
domperidone Domperidone: A specific blocker of dopamine receptors. It speeds gastrointestinal peristalsis, causes prolactin release, and is used as antiemetic and tool in the study of dopaminergic mechanisms.. domperidone : 1-[3-(Piperidin-1-yl)propyl]-1,3-dihydro-2H-benzimidazol-2-one in which the 4-position of the piperidine ring is substituted by a 5-chloro-1,3-dihydro-2H-benzimidazol-2-on-1-yl group. A dopamine antagonist, it is used as an antiemetic for the short-term treatment of nausea and vomiting, and to control gastrointestinal effects of dopaminergic drugs given in the management of parkinsonism. The free base is used in oral suspensions, while the maleate salt is used in tablet preparations.	2.11	1	benzimidazoles; heteroarylpiperidine	antiemetic; dopaminergic antagonist
ellipticine ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.	2.11	1	indole alkaloid; organic heterotetracyclic compound; organonitrogen heterocyclic compound; polycyclic heteroarene	antineoplastic agent; 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.	3.31	1	trihydroxyanthraquinone	antineoplastic agent; laxative; plant metabolite; tyrosine kinase inhibitor
glyphosate glyphosate: active cpd in herbicidal formulation Roundup; inhibits EC 2.5.1.19, 5-enolpyruvylshikimate-3-phosphate synthase; structure. glyphosate : A phosphonic acid resulting from the formal oxidative coupling of the methyl group of methylphosphonic acid with the amino group of glycine. It is one of the most commonly used herbicides worldwide, and the only one to target the enzyme 5-enolpyruvyl-3-shikimate phosphate synthase (EPSPS).	2.11	1	glycine derivative; phosphonic acid	agrochemical; EC 2.5.1.19 (3-phosphoshikimate 1-carboxyvinyltransferase) inhibitor; herbicide
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	2.11	1	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
miltefosine miltefosine: hexadecyl phosphocholine derivative of cisplatin; did not substantially activate HIV long terminal repeat; less toxic than cisplatin. miltefosine : A phospholipid that is the hexadecyl monoester of phosphocholine.	2.11	1	phosphocholines; phospholipid	anti-inflammatory agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antiprotozoal drug; apoptosis inducer; immunomodulator; protein kinase inhibitor
hypericin [no description available]	2.11	1
batyl alcohol batyl alcohol: RN given refers to cpd without isomeric designation. batilol : An alkylglycerol that is glycerol in which one of the primary hydroxy groups has been converted into the corresponding octadecyl ether. It is used in cosmetics as a stabilising ingredient and skin-conditioning agent.	2.11	1	alkylglycerol
imipramine Imipramine: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.. imipramine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.	2.11	1	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
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).	2.11	1	indolobenzazepine; lactam; organobromine compound	cardioprotective agent; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor; EC 2.7.11.26 (tau-protein kinase) inhibitor; geroprotector
ketoconazole 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.	2.11	1	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
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.	2.11	1	furanochromone; organic heterotricyclic compound; oxacycle	anti-asthmatic agent; bronchodilator agent; cardiovascular drug; vasodilator agent
2-amino-3-phosphonopropionic acid 2-amino-3-phosphonopropionic acid: metabotropic glutamate receptor antagonist; do not confuse AP-3 used as an abbreviation for this with enhancer-binding protein AP-3 (a trans-activator) or clathrin assembly protein AP-3. 2-amino-3-phosphonopropanoic acid : A non-proteinogenc alpha-amino acid that is alanine in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group.	2.11	1	alanine derivative; non-proteinogenic alpha-amino acid; phosphonic acids	human metabolite; metabotropic glutamate receptor antagonist
benzylsuccinic acid benzylsuccinic acid: inhibitor of carboxypeptidase A. 2-benzylsuccinic acid : A dicarboxylic acid consisting of succinic acid carrying a 2-benzyl substituent.	2.11	1	dicarboxylic acid	bacterial xenobiotic metabolite
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.	2.11	1	benzochromenone; orthoquinones	anti-inflammatory agent; antineoplastic agent; plant metabolite
mesoridazine Mesoridazine: A phenothiazine antipsychotic with effects similar to CHLORPROMAZINE.. mesoridazine : A phenothiazine substituted at position 2 (para to the S atom) by a methylsulfinyl group, and on the nitrogen by a 2-(1-methylpiperidin-2-yl)ethyl group.	2.11	1	phenothiazines; sulfoxide; tertiary amino compound	dopaminergic antagonist; first generation antipsychotic
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.	2.11	1	aromatic ether; psoralens	antineoplastic agent; cross-linking reagent; dermatologic drug; photosensitizing agent; plant metabolite
oxaprozin Oxaprozin: An oxazole-propionic acid derivative, cyclooxygenase inhibitor, and non-steroidal anti-inflammatory drug that is used in the treatment of pain and inflammation associated with of OSTEOARTHRITIS; RHEUMATOID ARTHRITIS; and ARTHRITIS, JUVENILE.. oxaprozin : A monocarboxylic acid that is a propionic acid derivative having a 4,5-diphenyl-1,3-oxazol-2-yl substituent at position 3. It is non-steroidal anti-inflammatory drug commonly used to relieve the pain and inflammatory responses associated with osteoarthritis and rheumatoid arthritis.	2.11	1	1,3-oxazoles; monocarboxylic acid	analgesic; non-steroidal anti-inflammatory drug
penicillamine [no description available]	2.11	1	non-proteinogenic alpha-amino acid; thiol
pentoxifylline [no description available]	2.11	1	oxopurine
phenolsulfonphthalein Phenolsulfonphthalein: Red dye, pH indicator, and diagnostic aid for determination of renal function. It is used also for studies of the gastrointestinal and other systems.. phenol red : 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 4-hydroxyphenyl groups. A pH indicator changing colour from yellow below pH 6.8 to bright pink above pH 8.2, it is commonly used as an indicator in cell cultures and in home swimming pool test kits. It is also used in the (now infrequently performed) phenolsulfonphthalein (PSP) test for estimation of overall blood flow through the kidney.	2.11	1	2,1-benzoxathiole; arenesulfonate ester; phenols; sultone	acid-base indicator; diagnostic agent; two-colour indicator
Picrotin, analytical standard [no description available]	2.11	1	furopyran
pomiferin pomiferin: structure in first source	2.11	1	isoflavanones
pridinol pridinol: antispasmodic & muscle relaxant; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7539. pridinol : A piperidine substituted at position 1 by a 3-hydroxy-3,3-diphenylpropyl group.	2.11	1	piperidines; tertiary alcohol	antiparkinson drug; muscle relaxant
sulfaquinoxaline Sulfaquinoxaline: An antiprotozoal agent used to combat coccidial infections of swine, cattle, fowl, and other veterinary animals. Also used in controlling outbreaks of fowl typhoid and fowl cholera and in treatment of infectious enteritis.	2.11	1	benzenes; sulfonamide
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	1.99	1	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
suramin Suramin: A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties.. suramin : A member of the class of phenylureas that is urea in which each of the amino groups has been substituted by a 3-({2-methyl-5-[(4,6,8-trisulfo-1-naphthyl)carbamoyl]phenyl}carbamoyl)phenyl group. An activator of both the rabbit skeletal muscle RyR1 and sheep cardiac RyR2 isoform ryanodine receptor channels, it has been used for the treatment of human African trypanosomiasis for over 100 years.	2.11	1	naphthalenesulfonic acid; phenylureas; secondary carboxamide	angiogenesis inhibitor; antinematodal drug; antineoplastic agent; apoptosis inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; GABA antagonist; GABA-gated chloride channel antagonist; purinergic receptor P2 antagonist; ryanodine receptor agonist; trypanocidal drug
4-methylglutamic acid 4-methylglutamic acid : A glutamic acid derivative that is glutamic acid substituted by a methyl group at position 4.	2.11	1	amino dicarboxylic acid; glutamic acid derivative
pilocarpine hydrochloride pilocarpine hydrochloride : The hydrochloride salt of (+)-pilocarpine, a medication used to treat increased pressure inside the eye and dry mouth.	2.11	1	hydrochloride
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.	2.11	1	piperidine alkaloid
chloroform Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.	2.03	1	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
gibberellic acid gibberellic acid: RN given refers to (1alpha,2beta,4aalpha,4bbeta,10beta)-isomer; structure. gibberellin A3 : A C19-gibberellin that is a pentacyclic diterpenoid responsible for promoting growth and elongation of cells in plants. Initially identified in Gibberella fujikuroi,it differs from gibberellin A1 in the presence of a double bond between C-3 and C-4.	2.11	1	C19-gibberellin; gibberellin monocarboxylic acid; lactone; organic heteropentacyclic compound	mouse metabolite; plant metabolite
santowhite powder 4,4'-butylidenebis(6-tert-butyl-m-cresol): putatively both an androgen and estrogen antagonist; structure in first source	2.11	1
fentichlor fentichlor: structure. fenticlor : An aryl sulfide having two 5-chloro-2-hydroxyphenyl groups attached to sulfur; an antiinfective drug mostly used in veterinary medicine.	2.11	1	aryl sulfide; bridged diphenyl antifungal drug; monochlorobenzenes; polyphenol	antiinfective agent; drug allergen
pyrrolidonecarboxylic acid Pyrrolidonecarboxylic Acid: A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism.. 5-oxo-L-proline : An optically active form of 5-oxoproline having L-configuration.	2.11	1	5-oxoproline; L-proline derivative; non-proteinogenic L-alpha-amino acid	algal metabolite
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.03	1	alkane
hexadecanolide hexadecanolide: structure in first source	2.11	1	macrolide
pamoic acid pamoic acid: RN given refers to parent cpd; structure	2.11	1	dicarboxylic acid
alpha-naphthylphthalamic acid alpha-naphthylphthalamic acid: RN given refers to parent cpd; structure. naptalam : A dicarboxylic acid monoamide which results from addition of one equivalent of 1-naphthylamine to phthalic anhydride.	2.01	1	carboxylic acid; dicarboxylic acid monoamide; N-(1-naphthyl)carboxamide	herbicide
carzenide [no description available]	2.11	1	sulfonamide
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	1.97	1	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
estradiol 17 beta-cypionate [no description available]	2.11	1	steroid ester
lithocholic acid Lithocholic Acid: A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic.. lithocholic acid : A monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.. lithocholate : A bile acid anion that is the conjugate base of lithocholic acid.	2.11	1	bile acid; C24-steroid; monohydroxy-5beta-cholanic acid	geroprotector; human metabolite; mouse metabolite
jervine jervine: teratogen from Veratrum grandiflorum; RN given refers to parent cpd(3beta,23beta)-isomer; structure	2.11	1	piperidines
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.	2.11	1	benzylisoquinoline alkaloid; isoquinoline alkaloid; isoquinolines	agrochemical; central nervous system stimulant; GABA-gated chloride channel antagonist; GABAA receptor antagonist; neurotoxin
salicylurate salicylurate: RN given refers to parent cpd. salicyluric acid : An N-acylglycine in which the acyl group is specified as 2-hydroxybenzoyl.. salicylurate : A monocarboxylic acid anion that is the conjugate base of salicyluric acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.11	1	N-acylglycine; secondary carboxamide	human xenobiotic metabolite; uremic toxin
3,5-pyridinedicarboxylic acid 3,5-pyridinedicarboxylic acid: structure in first source	2.11	1	pyridinedicarboxylic acid
oleanolic acid [no description available]	2.5	2	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
ricinine [no description available]	2.11	1	nitrile; pyridine alkaloid; pyridone
2,4,6-trimethylphenol [no description available]	2.03	1	hydroxytoluene
carinamide [no description available]	2.11	1
3,5-dibromotyrosine 3,5-dibromotyrosine: used to synthesize various secondary metabolites from marine sponges	2.11	1	monocarboxylic acid
hematoporphyrin Hematoporphyrins: Iron-free derivatives of heme with 4 methyl groups, 2 hydroxyethyl groups and 2 propionic acid groups attached to the pyrrole rings. Some of these PHOTOSENSITIZING AGENTS are used in the PHOTOTHERAPY of malignant NEOPLASMS.. hematoporphyrin : A dicarboxylic acid that is protoporphyrin in which the vinyl groups at positions 7 and 12 are replaced by 1-hydroxyethyl groups.	2.11	1
1H-indazol-3-amine 1H-indazol-3-amine: structure in first source	2.11	1	indazoles
1,1'-methylenedi-2-naphthol 1,1'-methylenedi-2-naphthol: piscicide	2.11	1
tricarballylic acid tricarballylic acid: RN given refers to parent cpd. tricarballylic acid : A tricarboxylic acid that is glutaric acid in which one of the beta-hydrogens is substituted by a carboxy group.	2.11	1	tricarboxylic acid
glycyrrhizic acid glycyrrhizinic acid : A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.	3.11	1	enone; glucosiduronic acid; pentacyclic triterpenoid; tricarboxylic acid; triterpenoid saponin	EC 3.4.21.5 (thrombin) inhibitor; plant metabolite
popop [no description available]	2.11	1	1,3-oxazoles	fluorochrome
2-tert-butylhydroquinone 2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent. 2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.	2.11	1	hydroquinones	food antioxidant
7-hydroxychlorpromazine 7-hydroxychlorpromazine: RN given refers to parent cpd	2.11	1	phenothiazines
cme-carbodiimide [no description available]	2.11	1
cyclacillin Cyclacillin: A cyclohexylamido analog of PENICILLANIC ACID.	2.11	1	penicillin	antibacterial drug
strombine N-methyliminodiacetic acid: structure in first source	2.11	1
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.	2.07	1	cadmium molecular entity; zinc group element atom
cupric chloride cupric chloride: RN given refers to unlabeled parent cpd. copper(II) chloride : An inorganic chloride of copper in which the metal is in the +2 oxidation state.	2	1	copper molecular entity; inorganic chloride	EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor
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.	1.97	1	benzenes; phenyl acetates
thymolphthalein Thymolphthalein: Used as a pH indicator and as a reagent for blood after decolorizing the alkaline solution by boiling with zinc dust.	2.11	1	terpene lactone
butylated hydroxytoluene 2,6-di-tert-butyl-4-methylphenol : A member of the class of phenols that is 4-methylphenol substituted by tert-butyl groups at positions 2 and 6.	2.11	1	phenols	antioxidant; ferroptosis inhibitor; food additive; geroprotector
1,4,5,8-naphthalenetetracarboxylic acid 1,4,5,8-naphthalenetetracarboxylic acid: structure given in first source	2.11	1
(7S,9S)-7-[(4-amino-5-hydroxy-6-methyl-2-oxanyl)oxy]-6,9,11-trihydroxy-9-(2-hydroxy-1-oxoethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione [no description available]	2.11	1	anthracycline
hydroxyphenylazouracil Hydroxyphenylazouracil: Inhibitor of DNA replication in gram-positive bacteria.	2.11	1
canadine canadine: RN given refers to cpd without isomeric designation; structure. canadine : A berberine alkaloid that is 5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline substituted by methoxy groups at positions 9 and 10.	2.11	1	aromatic ether; berberine alkaloid; organic heteropentacyclic compound; oxacycle
pimonidazole pimonidazole: structure given in first source	2.11	1
flavone acetic acid flavone acetic acid: structure given in first source	2.11	1
trichlorophene trichlorophene: contains 20 carbon atoms; do not confuse with trichlorophene as name for trichloro derivs of 2,2'-methylenebisphenol (contain 13 carbon atoms)	2.11	1
verapamil hydrochloride verapamil hydrochloride : A racemate comprising equimolar amounts of dexverapamil hydrochloride and (S)-verapamil hydrochloride.	2.11	1
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.	2.73	3	D-glucopyranose	epitope; mouse 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.	3.31	1	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
4-aminomethylbenzoic acid [no description available]	2.11	1	benzoic acids
cedrol cedrol: a cyclic terpenoid from cedarwood oil; 8-epicedrol is an epimer	2.11	1	cedrane sesquiterpenoid; tertiary alcohol
propazole propazole: RN given refers to parent cpd; structure	2.11	1	benzimidazoles
reserpic acid reserpic acid: inhibitor of norepinephrine transport into chromaffin vesicle ghosts; RN given refers to (3beta,16beta,17alpha,18beta,20alpha)-isomer parent cpd; structure given in first source	2.11	1	yohimban alkaloid
pifexole pifexole: structure	2.11	1
Diphenolic acid diphenolic acid: an estrogenic ligand	2.11	1	bisphenol
Melicopidine [no description available]	2.11	1	acridines
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.	2.08	1	(2S)-flavan-4-one; dihydroxyflavanone	antineoplastic agent; antioxidant; metabolite; neuroprotective agent; vasodilator agent
resorufin [no description available]	2.11	1	phenoxazine
vinburnine [no description available]	2.11	1	alkaloid
gallocatechol (-)-epigallocatechin : A flavan-3,3',4',5,5',7-hexol having (2R,3R)-configuration.	3.31	1	catechin; flavan-3,3',4',5,5',7-hexol	antioxidant; food component; plant metabolite
pacein PAcein: structure. pacein : A member of the class of benzofurans that is dibenzo[b,d]furan-3,7-dione bearing two methyl substituents at positions 1 and 9 as well as two 2,4-dihydroxy-6-methylanilino substituents at positions 2 and 8.. orcein : A variable mixture of several compounds isolated from lichens, the eight most abundant being alpha-aminoorcein, alpha-hydroxyorcein, beta-aminoorcein, gamma-aminoorcein, beta-hydroxyorcein, gamma-hydroxyorcein, beta-aminoorceimine and beta-aminoorceimine (all are phenoxazine-based). It is used for the demonstration of elastic fibres as well as to stain the rough endoplasmic reticulum of hepatitis B infected liver cells.	2.11	1
alantolactone alantolactone: allergenic sesquiterpene lactone; crystalline mixture of alantolactones from group of sesquiterpenes; structure. alantolactone : A sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at position 3.	2.11	1	naphthofuran; olefinic compound; sesquiterpene lactone	antineoplastic agent; apoptosis inducer; plant metabolite
2-(4'-methylpiperazino-1-methyl)-1,3-diazafluoranthene 1-oxide 2-(4'-methylpiperazino-1-methyl)-1,3-diazafluoranthene 1-oxide: structure	2.11	1
tetrandrine tetrandrine: a bisbenzylisoquinoline that exhibits antifibrogenic activity	2.11	1	bisbenzylisoquinoline alkaloid; isoquinolines
beta-amyrin beta-amyrin: alpha-amyrin is also available; a 5 ring triterpene derived from oleanane that differs from alpha-amyrin in having the 29-carbon at the 20 position; RN given refers to (3 beta)-isomer. beta-amyrin : A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants.	2.25	1	pentacyclic triterpenoid; secondary alcohol	Aspergillus metabolite; plant metabolite
pinostrobin [no description available]	2.08	1	monohydroxyflavanone; monomethoxyflavanone	antidote; plant metabolite
stictic acid stictic acid: antioxidant from lichen, Usnea articulata; structure in first source	2.11	1	aromatic ether
gallocyanine gallocyanine: structure; gallocyanine-chrome alum is used as a nuclear stain to quantitate nucleic acids. gallocyanin : An organic chloride salt composed of 1-carboxy-7-(dimethylamino)-3,4-dihydroxyphenoxazin-5-ium and chloride ions in a 1:1 ratio. A histological dye used in solution with an iron alum mordant as a hematoxylin substitute in the H&E stain.	2.11	1
oxazolidin-2-one Oxazolidinones: Derivatives of oxazolidin-2-one. They represent an important class of synthetic antibiotic agents.. oxazolidin-2-one : An oxazolidinone that is 1,3-oxazolidine with an oxo substituent at position 2.. oxazolidinone : An oxazolidine containing one or more oxo groups.	2.15	1	carbamate ester; oxazolidinone	metabolite
propylsulfonic acid propylsulfonic acid: RN given refers to cpd without locant for propyl moiety	2.11	1
1-cyclohexyl-3-(2-(4-morpholinyl)ethyl)carbodiimide N-cyclohexyl-N'-(2-(4-morpholinyl)ethyl)carbodiimide : A carbodiimide having cyclcohexyl and 2-(4-morpholinyl)ethyl as the two N-substituents.	2.11	1	carbodiimide; morpholines	cross-linking reagent
6,6'-dithiodinicotinic acid 6,6'-dithiodinicotinic acid: RN given refers to parent cpd; structure	2.11	1
va 061 VA 061: a water-soluble radical initiator; structure in first source	2.11	1
n-acetyltyrosine, (dl)-isomer N-acetyltyrosine: RN given refers to (L)-isomer. N-acetyltyrosine : An N-acetyl-amino acid that is tyrosine with an amine hydrogen substituted by an acetyl group.	2.11	1	N-acetyl-amino acid; phenols; tyrosine derivative	human urinary metabolite
cinchonine [no description available]	2.11	1	(8xi)-cinchonan-9-ol; cinchona alkaloid	metabolite
equol Equol: A non-steroidal ESTROGEN generated when soybean products are metabolized by certain bacteria in the intestines.	2.03	1	hydroxyisoflavans
inermin inermin: phytoalexin produced in plants after injection with fungi; RN given refers to (cis-(+-))-isomer; RN for cpd without isomeric designation; structure. (-)-maackiain : The (-)-enantiomer of maackiain.	3.74	10	maackiain
n(6)-(delta(2)-isopentenyl)adenine N(6)-dimethylallyladenine : A 6-isopentenylaminopurine in which has the isopentenyl double bond is located between the 2 and 3 positions of the isopentenyl group.	2.11	1	6-isopentenylaminopurine	cytokinin
2-Phthalimidoglutaricacid [no description available]	2.11	1	glutamic acid derivative
vestitol vestitol: structure in first source. vestitol : A member of the class of hydroxyisoflavans that is isoflavan substituted by hydroxy groups at positions 7 and 2' and a methoxy group at position 4'. Isolated from Glycyrrhiza uralensis, it exhibits anti-inflammatory activity.	2.25	1	aromatic ether; hydroxyisoflavans; methoxyisoflavan	anti-inflammatory agent; phytoalexin; plant metabolite
nsc-87877 NSC-87877: potent Shp2 (nonreceptor protein tyrosine phosphatase) inhibitor; structure in first source	2.11	1
methyl lithocholate methyl lithocholate: RN given refers to (3alpha,5beta)-isomer	2.11	1
nipecotic acid amide nipecotic acid amide: RN & N1 form 9th CI Form Index; RN given refers to cpd without isomeric designation. nipecotamide : The amide resulting from the formal condensation of nipecotic acid with ammonia.	2.11	1	piperidinecarboxamide
dimethacrine dimethacrine: minor descriptor (75-84); on-line & Index Medicus search ACRIDINES (75-84); RN given refers to parent cpd without isomeric designation	2.11	1	acridines
dehydroabietic acid dehydroabietic acid: major aquatic toxicant in effluent of pulp and paper mills. dehydroabietic acid : An abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group.. dehydroabietate : A monocarboxylic acid anion that is the conjugate base of dehydroabietic acid, obtained by deprotonation of the carboxy group.	2.11	1	abietane diterpenoid; carbotricyclic compound; monocarboxylic acid	allergen; metabolite
4-deoxypyridoxine 5'-phosphate [no description available]	2.11	1
4-(phenylthio)butanoic acid 4-(phenylthio)butanoic acid: structure in first source	2.11	1
bis-a-tda bis-A-TDA: structure given in first source	2.11	1
1-amino-2-phenylethylphosphonic acid 1-amino-2-phenylethylphosphonic acid: RN given refers to cpd without isomeric designation: structure given in first source	2.11	1
4-fluoro-alpha-hydroxybenzeneacetic acid 4-fluoro-alpha-hydroxybenzeneacetic acid: an aprepitant urinary metabolite; structure in first source	2.11	1
Isopteropodin [no description available]	2.11	1	indolizines
benzpiperylone benzpiperylone: spelled benzopiperylone in title	2.11	1	pyrazoles; ring assembly
homopterocarpin homopterocarpin: an insect antifeedant isolated from Pterocarpus marcocarpus; structure in first source	2.44	2	pterocarpans
pisatin pisatin: phytoalexin produced in plants after injection with fungi; RN given refers to (6aS-cis)-isomer; structure	2.45	2
epicatechin gallate epicatechin gallate: a steroid 5alpha-reductase inhibitor; RN given refers to the (cis)-isomer; structure given in first source; isolated from green tea. (-)-epicatechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.	3.31	1	catechin; gallate ester; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
carboxyamido-triazole carboxyamido-triazole: structure given in first source; coccidiostat; U.S. patent No. 4,590,201	2.11	1
liquiritigenin liquiritigenin: structure given in first source; isolated from Pterocarpus marsupium. 4',7-dihydroxyflavanone : A dihydroxyflavanone in which the two hydroxy substituents are located at positions 4' and 7.. liquiritigenin : A dihydroxyflavanone compound having the two hydroxy substituents at the 4'- and 7-positions. Isolated from the root of Glycyrrhizae uralensis, it is a selective agonist for oestrogen receptor beta.	9.29	5	4',7-dihydroxyflavanone	hormone agonist; plant metabolite
nsc 607097 [no description available]	2.11	1
pacifenol pacifenol: isolated from sea weeds and marine alga Laurencia claviformis; RN refers to (2R,5R,5aR,7S,8S,9aS)-isomer; structure in first source	2.11	1
n-phenyliminodiacetic acid [no description available]	2.11	1
cyc 202 seliciclib : 2,6-Diaminopurine carrying benzylamino, (2R)-1-hydroxybutan-2-yl and isopropyl substituents at C-6, C-2-N and N-9 respectively. It is an experimental drug candidate in the family of pharmacological cyclin-dependent kinase (CDK) inhibitors.	2.11	1	2,6-diaminopurines	antiviral drug; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
cystamine hydrochloride [no description available]	2.11	1
dipiperidinoethane-di-n-oxide dipiperidinoethane-di-N-oxide: oxidized neurotoxic dipiperidinoethane deriv; structure given in first source	2.11	1
methyl abietate methyl abietate: RN given refers to (1R-(1alpha,4abeta,4balpha,10aalpha))-isomer	2.03	1
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	2.17	1
(-)-gallocatechin gallate (-)-gallocatechin gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of (-)-gallocatechin. A natural product found in found in green tea.	3.31	1	catechin; gallate ester; polyphenol	antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human xenobiotic metabolite; plant metabolite
benzyl-beta-d-xyloside benzyl-beta-D-xyloside: RN given refers to (beta-D)-isomer	2.11	1
2,2'-(3-methylcyclohexane-1,1-diyl)diacetic acid [no description available]	2.11	1	dicarboxylic acid
2,4-dinitrophenylacetic acid 2,4-dinitrophenylacetic acid: RN given refers to parent cpd	2.11	1
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.	2.11	1	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C29-steroid; phytosterols; stigmastane sterol	anticholesteremic drug; antioxidant; mouse metabolite; plant metabolite; sterol methyltransferase inhibitor
(5-Phenyl-1,2,4-triazol-3-yl)urea [no description available]	2.11	1	benzenes
fumagillol fumagillol: from Penicillium jensenii; FR 65814 is an analog; structure given in first source. fumagillol : A sesquiterpenoid with antimicrobial properties.	2.11	1	secondary alcohol; sesquiterpenoid; spiro-epoxide	antimicrobial agent
vacquinol-1 [no description available]	2.11	1
aspidospermine aspidospermine: an indole fused to a qunoline; isolated from Aspidosperma tree; structure given in first source. aspidospermine : An indole alkaloid having the structure of aspirospermidine methoxylated at C-17 and acetylated at N-1.	2.11	1	indole alkaloid
guaiol guaiol: structure in first source	2.11	1	guaiane sesquiterpenoid
benzatropine methanesulfonate [no description available]	2.11	1
pseudoyohimbine [no description available]	2.11	1	methyl 17-hydroxy-20xi-yohimban-16-carboxylate
gant58 GANT58: inhibits hedgehog signalling; structure in first source	2.11	1	pyridines
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.92	4
nsc 88915 4-pregnen-21-ol-3,20-dione-21-(4-bromobenzenesufonate): a tyrosyl-DNA phosphodiesterase inhibitor; structure in first source	2.11	1
o-acetylsolasodine [no description available]	2.11	1
viroallosecurinine [no description available]	2.11	1	indolizines
4-methyl-2-quinazolinamine 4-methyl-2-quinazolinamine: from Streptomyces of TCM plant; structure in first source	2.11	1
1-amino-9,10-dioxo-4-(3-sulfamoylanilino)anthracene-2-sulfonic acid 1-amino-9,10-dioxo-4-(3-sulfamoylanilino)anthracene-2-sulfonic acid: inhibits PH domain leucine-rich repeat protein phosphatase; structure in first source	2.11	1
adamantoylcytarabine adamantoylcytarabine: RN given refers to parent cpd; structure in Negwer, 5th ed, #4393	2.11	1
6,11-dioxo-12-naphtho[2,3-b]indolizinecarboxylic acid ethyl ester [no description available]	2.11	1	naphthalenes
noscapine Noscapine: A naturally occurring opium alkaloid that is a centrally acting antitussive agent.. (-)-noscapine : A benzylisoquinoline alkaloid that is 1,2,3,4-tetrahydroisoquinoline which is substituted by a 4,5-dimethoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl group at position 1, a methylenedioxy group at positions 6-7 and a methoxy group at position 8. Obtained from plants of the Papaveraceae family, it lacks significant painkilling properties and is primarily used for its antitussive (cough-suppressing) effects.	2.11	1	aromatic ether; benzylisoquinoline alkaloid; cyclic acetal; isobenzofuranone; organic heterobicyclic compound; organic heterotricyclic compound; tertiary amino compound	antineoplastic agent; antitussive; apoptosis inducer; plant metabolite
LSM-1290 [no description available]	2.11	1	benzazepine alkaloid; cyclic acetal
2-glycineamide-5-chlorophenyl-2-pyrryl ketone [no description available]	2.11	1
nsc 154020 [no description available]	2.11	1	N-glycosyl compound
4-[(1-naphthalenylamino)-oxomethyl]benzene-1,3-dicarboxylic acid [no description available]	2.11	1	2-hydroxyisophthalic acid
2,2-bis(hydroxymethyl)-1-azabicyclo(2,2,2,)octan-3-one 2,2-bis(hydroxymethyl)-1-azabicyclo(2,2,2,)octan-3-one: structure in first source	2.11	1	cyclic ketone; quinuclidines
5-(1,3-benzodioxol-5-yl)-N-(2,4-dimethylphenyl)-1,3,4-oxadiazol-2-amine [no description available]	2.11	1	benzodioxoles
croton factor f1 croton factor F1: induces ornithine decarboxylase activity; structure given in first source. 16-hydroxyphorbol 13-decanoate 12-palmitate : A phorbol ester that consists of 16-hydroxyphorbol bearing O-hexadecanoyl (palmitoyl) and O-decanoyl substituents at position 12 and 13 respectively.	2.11	1	phorbol ester; tertiary alpha-hydroxy ketone
latifolin latifolin: structure in first source	2.08	1
gitoxigenin gitoxigenin: structure	2.11	1	14beta-hydroxy steroid; 16beta-hydroxy steroid; 3beta-hydroxy steroid
aromoline aromoline: from roots of Stephania cepharantha; structure given in first source	2.11	1
nsc668394 [no description available]	2.11	1
gant 61 GANT 61: a sonic hedgehog pathway inhibitor and Gli inhibitor; structure in first source. GANT61 : An aminal that is hexahydropyrimidine which is substituted on each nitrogen by a 2-(dimethylamino)benzyl group, and at the aminal carbon by a pyridin-4-yl group. A Hedgehog signaling pathway and Gli protein inhibitor.	2.11	1	aminal; dialkylarylamine; pyridines; substituted aniline; tertiary amino compound	antineoplastic agent; apoptosis inducer; glioma-associated oncogene inhibitor; Hedgehog signaling pathway inhibitor
s-adenosylhomocysteine S-Adenosylhomocysteine: 5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine. Formed from S-adenosylmethionine after transmethylation reactions.. S-adenosyl-L-homocysteine : An organic sulfide that is the S-adenosyl derivative of L-homocysteine.	2.03	1	adenosines; amino acid zwitterion; homocysteine derivative; homocysteines; organic sulfide	cofactor; EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor; EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor; epitope; fundamental metabolite
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	3.61	2	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
vestitone [no description available]	2.4	2	(3R)-2'-hydroxyisoflavanones; hydroxyisoflavanone; methoxyisoflavanone	antibacterial agent; metabolite
eriodictyol eriodictyol: structure. eriodictyol : A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' respectively.	3.31	1	3'-hydroxyflavanones; tetrahydroxyflavanone
nortriptyline hydrochloride [no description available]	2.11	1	organic tricyclic compound	geroprotector
sophoranone sophoranone: a flavonoid compound with isoprenoid side chains; extracted from a traditional Chinese medicine Shan Dou Gen, isolated from the roots of Sophora subprostrata; structure in first source. sophoranone : A dihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 7 and 4' and prenyl groups at positions 3' and 5' respectively.	2.15	1	4'-hydroxyflavanones; dihydroxyflavanone	plant metabolite
naringin [no description available]	2.06	1	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
ononin [no description available]	2.11	1	4'-methoxyisoflavones; 7-hydroxyisoflavones 7-O-beta-D-glucoside; monosaccharide derivative	plant metabolite
trifolirhizin trifolirhizin: from Sophora flavescens; has inhibitory effect on tyrosinase and melanin synthesis; structure in first source	2.15	1	pterocarpans
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2	1	cyclodextrin
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	2	1	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
nsc 45641 [no description available]	2.11	1
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	2.15	1	4-coumaric acid	food component; mouse metabolite; plant metabolite
geraniol [no description available]	2.11	1	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	2.13	1
chalcone trans-chalcone : The trans-isomer of chalcone.	3.11	1	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
isoliquiritigenin [no description available]	4.79	5	chalcones	antineoplastic agent; biological pigment; EC 1.14.18.1 (tyrosinase) inhibitor; GABA modulator; geroprotector; metabolite; NMDA receptor antagonist
aconitic acid cis-aconitic acid : The cis-isomer of aconitic acid.	2.11	1	aconitic acid	fundamental metabolite
amygdalin [no description available]	2.11	1
sesquiterpenes [no description available]	3.54	8
(2S)-7-hydroxyflavanone [no description available]	3.31	1	7-hydroxyflavanone
alpha-phenylcinnamate alpha-phenylcinnamate: RN given refers to parent cpd	2.11	1
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.	3.65	2	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
ethyldimethylaminopropyl carbodiimide 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride: structure in first source	2.11	1
tamoxifen citrate [no description available]	2.11	1	citrate salt	angiogenesis inhibitor; anticoronaviral agent
hydroxypropyl-gamma-cyclodextrin [no description available]	2	1
nadp [no description available]	1.98	1
eskazine [no description available]	2.11	1
nsc 336628 [no description available]	2.11	1
1,3-dimethyl-8-[2-(1-pyrrolidinyl)ethylthio]-6-sulfanylidene-7H-purin-2-one [no description available]	2.11	1	oxopurine
cambinol cambinol: inhibitor of human silent information regulator 2 enzymes; structure in first source	2.11	1
nsc 117199 [no description available]	2.11	1
quercetin [no description available]	4.12	4	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
biochanin a [no description available]	2.06	1	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]	5.74	15	4'-methoxyisoflavones; 7-hydroxyisoflavones	phytoestrogen; 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.	3.31	1	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	3.31	1	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
7,3'-dihydroxy-4'-methoxyisoflavone 7,3'-dihydroxy-4'-methoxyisoflavone: isolated from Astragali radix; structure in first source. calycosin : A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at the 3' position and a methoxy group at the 4' position.	2.13	1	4'-methoxyisoflavones; 7-hydroxyisoflavones	antioxidant; metabolite
leukotriene b4 Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.	1.97	1	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
kaempferol [no description available]	3.31	1	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
genistein [no description available]	4.79	5	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
butein [no description available]	2.08	1	chalcones; polyphenol	antineoplastic agent; antioxidant; EC 1.1.1.21 (aldehyde reductase) inhibitor; geroprotector; hypoglycemic agent; plant metabolite; radiosensitizing agent; tyrosine kinase inhibitor
chrysin chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.	3.31	1	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
mangostin mangostin: xanthone from rind of Garcinia mangostana Linn. fruit. alpha-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3 and 6, a methoxy group at position 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antioxidant, antimicrobial and antitumour activities.	2.11	1	aromatic ether; phenols; xanthones	antimicrobial agent; antineoplastic agent; antioxidant; plant metabolite
myricetin [no description available]	3.31	1	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
7-hydroxy-6,4'-dimethoxyisoflavone afromosin: structure given in first source; isolated from Wistaria brachybotrys. afrormosin : A 4'-methoxyisoflavone that is isoflavone substituted by methoxy groups at positions 6 and 4' and a hydroxy group at position 7.	2.06	1	4'-methoxyisoflavones; 7-hydroxyisoflavones	plant metabolite
coumestrol Coumestrol: A daidzein derivative occurring naturally in forage crops which has some estrogenic activity.. coumestrol : A member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9.	2.49	2	coumestans; delta-lactone; polyphenol	anti-inflammatory agent; antioxidant; plant metabolite
daidzein [no description available]	4.55	7	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
orobol orobol: from Aspergillus niger or Streptomyces neyagawaensis; potent inhibitor of phosphatidylinositol kinase. orobol : A member of the class of 7-hydroxyisoflavones which consists of isoflavone substituted by hydroxy groups at positions 5, 7, 3' and 4'. It has been isolated from the mycelia of Cordyceps sinensis.	2.08	1	7-hydroxyisoflavones	anti-inflammatory agent; fungal metabolite; plant metabolite; radical scavenger
prunetin prunetin: reduces herpes virus-1 plaque formation. prunetin : A hydroxyisoflavone that is genistein in which the hydroxy group at position 7 is replaced by a methoxy group.	2.03	1	7-methoxyisoflavones; hydroxyisoflavone	anti-inflammatory agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor; metabolite
psi-baptigenin pseudobaptigenin : A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone and in which the phenyl group at position 3 is replaced by a 1,3-benzodioxol-5-yl group.	2.49	2	7-hydroxyisoflavones; benzodioxoles	antiprotozoal drug; plant metabolite
tectorigenin tectorigenin: tectoridin is glycosylated form. tectorigenin : A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 5, 7 and 4' respectively.	2.13	1	7-hydroxyisoflavones; methoxyisoflavone	anti-inflammatory agent; plant 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.	2.11	1	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]	2.11	1	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
4',7-dihydroxyflavone 4',7-dihydroxyflavone: inducer of nod gene. 4',7-dihydroxyflavone : A dihydroxyflavone in which the two hydroxy substituents are located at positions 4' and 7.	2.46	2	dihydroxyflavone	metabolite
broussonin b broussonin B: structure in first source	3.31	1
7,8-dimethylalloxazine 7,8-dimethylalloxazine: structure. 7,8-dimethylisoalloxazine : A 7,8-dimethylbenzo[g]pteridine-2,4-dione that is isoalloxazine substituted by methyl groups at positions 7 and 8.. lumichrome : A compound showing blue fluorescence, formed by a photolysis of riboflavin in acid or neutral solution.	2.11	1	7,8-dimethylbenzo[g]pteridine-2,4-dione	plant metabolite
guttiferone e guttiferone E: isolated from the fruits of Garcinia pyrifera collected in Malaysia; structure in first source	2.25	1
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	7.1	1	carbon group element atom; elemental lead; metal atom	neurotoxin
dihydrothobainone [no description available]	2.11	1
piperic acid piperinic acid: from Piper longum; structure in first source. (E,E)-piperic acid : A monocarboxylic acid that is (E)-penta-2,4-dienoic acid substituted by a 1,3-benzodioxol-5-yl group at position 5. It has been isolated from black pepper (Piper nigrum).	2.11	1	alpha,beta-unsaturated monocarboxylic acid; benzodioxoles	plant metabolite
abscisic acid 2-trans-abscisic acid : An abscisic acid in which the two acyclic double bonds both have trans-geometry.	2.11	1	abscisic acids
radicinin radicinin: mold metabolite from plant pathogen Stemphylium radicinum; RN given refers to (2S-(2alpha,3beta,7E))-isomer; structure	2.11	1	aromatic ketone
5,6-dichloro-1H-imidazo[4,5-b]pyrazine-2-carboxylic acid [no description available]	2.11	1	imidazopyrazine
hispanolone hispanolone: structure in first source	2.11	1
(-)-catechin-3-O-gallate (-)-catechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of (-)-catechin.	3.31	1	flavans; gallate ester; polyphenol	metabolite
beta-escin [no description available]	3.55	2
oleanane oleanane: from the aerial roots of Ficus microcarpa; structure in first source	2.04	1	terpenoid fundamental parent; triterpene
glutinol glutinol: from a medicinal lichen, Usnea longissima; structure in first source. glutinol : A pentacyclic triterpenoid that is picene which has been fully hydrogenated except for a double bond between the 4a and 5 positions and is substituted by methyl groups at the 4, 4, 6bbeta, 8abeta, 11, 11, 12balpha and 14bbeta positions, and by a hydroxy group at the 3beta position.	2.25	1	pentacyclic triterpenoid; secondary alcohol
glabrol glabrol: from Glycyrrhiza glabra hairy root; structure in first source	2.15	1	flavanones
veratridine Veratridine: A benzoate-cevane found in VERATRUM and Schoenocaulon. It activates SODIUM CHANNELS to stay open longer than normal.	2.11	1
lyoniresinol lyoniresinol: isoalted from the vine stem of Bauhinia championii; structure in first source. (+)-lyoniresinol : A lignan that is tetralin substituted by a 4-hydroxy-3,5-dimethoxy group at position 4, hydroxymethyl groups at positions 2 and 3, methoxy groups at positions 5 and 7 and a hydroxy group at position 6. Isolated from Machilus robusta and Sinocalamus affinis, it exhibits antineoplastic activity.	2.1	1	dimethoxybenzene; lignan; polyphenol; primary alcohol; tetralins	antineoplastic agent; metabolite
losartan potassium Erythropoietin: Glycoprotein hormone, secreted chiefly by the KIDNEY in the adult and the LIVER in the FETUS, that acts on erythroid stem cells of the BONE MARROW to stimulate proliferation and differentiation.	2.15	1
2,7,4'-trihydroxyisoflavanone 2,7,4'-trihydroxyisoflavanone: structure in first source. 2,4',7-trihydroxyisoflavanone : A hydroxyisoflavanone that is isoflavanone with hydroxy substituents at positions 2, 7 and 4'.	2	1	hydroxyisoflavanone; lactol
scopolamine hydrobromide [no description available]	2.31	1
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.	2.11	1	chlorophyll; methyl ester	cofactor
zimelidine hydrochloride [no description available]	2.11	1
s-adenosylmethionine (R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.	2.03	1	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2	1	benzenes; hydroxycoumarin; methyl ketone
chlortetracycline hydrochloride Alexomycin: a thiopeptide; a cyclic peptide antibiotic produced by Streptomyces arginensis isolated from the soil	2.11	1
viridicatumtoxin viridicatumtoxin: isolated from cultures of Penicillium viridicatum; RN given refers to 2'alpha,7'beta,11'abeta,12'beta-(-) isomer. viridicatumtoxin : A tetracycline-like polyketide antibiotic that is produced by several species of Penicillium and Aspergillus.	2.11	1
phytoestrogens Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.	2	1
lupane lupane: has antineoplastic activity; structure in first source	2.04	1
dacarbazine (E)-dacarbazine : A dacarbazine in which the N=N double bond adopts a trans-configuration.	2.11	1	dacarbazine
hematein hematein: structure. hematein : An organic heterotetracyclic compound that is -6a,7-dihydrobenzo[b]indeno[1,2-d]pyran-9-one carrying four hydroxy substituents at positions 3, 4, 6a and 10.	2.11	1

Condition	Relationship Strength	Studies
Experimental Hepatoma [description not available]	1.99	1
Innate Inflammatory Response [description not available]	3.33	5
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.	3.33	5
Benign Neoplasms [description not available]	3.12	1
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.	3.12	1
Injury, Ischemia-Reperfusion [description not available]	2.41	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.	2.41	1
Disease Resistance The capacity of an organism to defend itself against pathological processes or the agents of those processes. This most often involves innate immunity whereby the organism responds to pathogens in a generic way. The term disease resistance is used most frequently when referring to plants.	2.88	3
Apoplexy [description not available]	2.31	1
Acute Brain Injuries [description not available]	2.31	1
Cerebral Ischemia [description not available]	7.31	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.51	6
Brain Injuries Acute and chronic (see also BRAIN INJURIES, CHRONIC) injuries to the brain, including the cerebral hemispheres, CEREBELLUM, and BRAIN STEM. Clinical manifestations depend on the nature of injury. Diffuse trauma to the brain is frequently associated with DIFFUSE AXONAL INJURY or COMA, POST-TRAUMATIC. Localized injuries may be associated with NEUROBEHAVIORAL MANIFESTATIONS; HEMIPARESIS, or other focal neurologic deficits.	2.31	1
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	2.31	1
Stroke A group of pathological conditions characterized by sudden, non-convulsive loss of neurological function due to BRAIN ISCHEMIA or INTRACRANIAL HEMORRHAGES. Stroke is classified by the type of tissue NECROSIS, such as the anatomic location, vasculature involved, etiology, age of the affected individual, and hemorrhagic vs. non-hemorrhagic nature. (From Adams et al., Principles of Neurology, 6th ed, pp777-810)	2.31	1
Bone Loss, Osteoclastic [description not available]	2.41	1
Age-Related Osteoporosis [description not available]	2.87	3
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.	2.87	3
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	3.33	4
Bladder Cancer [description not available]	7.6	1
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.6	1
Acute Confusional Senile Dementia [description not available]	2.31	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)	2.31	1
Acute Liver Injury, Drug-Induced [description not available]	2.1	1
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	2.1	1
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.	2.1	1
Granulocytic Leukemia [description not available]	2.1	1
Leukemia, Myeloid Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.	2.1	1
Bone Loss, Perimenopausal [description not available]	2.11	1
Osteoporosis, Postmenopausal Metabolic disorder associated with fractures of the femoral neck, vertebrae, and distal forearm. It occurs commonly in women within 15-20 years after menopause, and is caused by factors associated with menopause including estrogen deficiency.	2.11	1
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	7.11	1
Low Bone Density [description not available]	2.11	1
Bone Diseases, Metabolic Diseases that affect the METABOLIC PROCESSES of BONE TISSUE.	2.11	1
Breast Cancer [description not available]	2	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2	1
Cancer of Nasopharynx [description not available]	2	1
Nasopharyngeal Neoplasms Tumors or cancer of the NASOPHARYNX.	2	1

medicarpin

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