shogaol profile

shogaol: from ginger, ZINGIBER OFFICINALE; less mutagenic than GINGEROL; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Related Flora

Flora	Rank	Flora Definition	Family	Family Definition
Zingiber	genus	[no description available]	Zingiberaceae	A plant family of the order Zingiberales, subclass Zingiberidae, class Liliopsida. It includes plants which have both flavoring and medicinal properties such as GINGER; turmeric (CURCUMA), and cardamom (ELETTARIA).[MeSH]

ID Source	ID
PubMed CID	5281794
CHEMBL ID	25948
CHEBI ID	10138
SCHEMBL ID	49054
MeSH ID	M0119623

Synonym
6-shogaol
4-decen-3-one, 1-(4-hydroxy-3-methoxyphenyl)
ACON1_001190
ccris 2038
4-decen-3-one, 1-(4-hydroxy-3-methoxyphenyl)-
(6)-shogaol
MEGXP0_001217
[6]-shogaol
555-66-8
shogaol
NCGC00169591-01
(e)-1-(4-hydroxy-3-methoxy-phenyl)-dec-4-en-3-one
[(e)-1-(4-hydroxy-3-methoxyphenyl)-dec-4-en-3-one]
bdbm50240419
chebi:10138 ,
trans-6-shogaol
CHEMBL25948 ,
BRD-K23331196-001-01-9
1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
(e)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
nsc752389
nsc-752389
nsc 752389
1-(4-hydroxy-3-methoxyphenyl)-4-decen-3-one
AKOS015888385
6-shogaol (constituent of ginger) [dsc]
83DNB5FIRF ,
enexasogaol [inn]
(e)-1-(4-hydroxy-3- methoxyphenyl)dec-4-en-3-one
enexasogaol
4-decen-3-one, 1-(4-hydroxy-3-methoxyphenyl)-, (e)
23513-13-5
SCHEMBL49054
H1771
W-206831
unii-83dnb5firf
AC-34334
Q-100639
bdbm50237536
CS-6175
HY-14616
4-decen-3-one, 1-(4-hydroxy-3-methoxyphenyl)-, (4e)-
[6]-shogaol, analytical standard
shogaol, >=90% (hplc)
1-(4-hydroxy-3-methoxyphenyl)-4-dodecen-3-one, 9ci
gtpl9773
Q2746448
shogaol (6-shogaol)
A14648
CCG-267210
(4e)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
AS-55975
S9043
DTXSID301336611
6-shogaol (constituent of ginger)

Excerpt	Reference	Relevance
"6-Shogaol is a major component of ginger and exhibits anti-oxidative and anti-inflammatory effects."	( Protective Effects of 6-Shogaol, an Active Compound of Ginger, in a Murine Model of Cisplatin-Induced Acute Kidney Injury. Gu, H; Gwon, MG; Leem, J; Park, KK, 2021)	1.49
"6-shogaol is a natural phenolic compound formed when ginger is exposed to heat and/or acidic conditions, and it has been shown to possess anti-tumor activity against leukemia cell lines and antioxidant effects."	( Is 6-Shogaol an Effective Phytochemical for Patients With Lower-risk Myelodysplastic Syndrome? A Narrative Review. Badmaev, V; Campbell, R; Golombick, T; Manoharan, A; Ooi, SL; Pak, SC; Ramakrishna, R; Schloss, J, )	1.2
"6-Shogaol is a biologically active substance derived from the rhizome of Zingiber officinale Roscoe with anti-tumor, anti-inflammatory, and antioxidant properties."	( 6-Shogaol alleviates CCl4-induced liver fibrosis by attenuating inflammatory response in mice through the NF-κB pathway. Chai, YN; Chen, LY; Duan, F; Duan, FY; Han, XY; Qiu, JL; Zhang, HJ, 2022)	2
"6-Shogaol is a promising candidate to be considered as a treatment of breast cancer."	( 6-Shogaol suppresses the growth of breast cancer cells by inducing apoptosis and suppressing autophagy via targeting notch signaling pathway. Al-Abbasi, FA; Al-Abd, AM; Anwar, F; Bawadood, AS; El-Halawany, AM, 2020)	2
"6-shogaol is a phytochemical of dietary ginger, we found that 6-shogaol could induced both autophagic and apoptotic death in human colon adenocarcinoma (HT-29) cells. "	( 6-shogaol induces autophagic cell death then triggered apoptosis in colorectal adenocarcinoma HT-29 cells. Chiang, BH; Li, TY, 2017)	1.9
"[6]-Shogaol ([6]-SHO) is a major constituent of ginger, exhibits various biological properties such as anti-oxidants, anti-inflammation and anti-tumor."	( [6]-Shogaol attenuates inflammation, cell proliferation via modulate NF-κB and AP-1 oncogenic signaling in 7,12-dimethylbenz[a]anthracene induced oral carcinogenesis. Annamalai, G; Suresh, K, 2018)	1.52
"[6]-Shogaol is a major bioactive component of Zingiber officinale. "	( [6]-Shogaol inhibits the production of proinflammatory cytokines via regulation of NF-κB and phosphorylation of JNK in HMC-1 cells. Cho, HJ; Han, NY; Jung, HS; Lee, MJ; Sohn, Y, 2013)	1.51
"6-Shogaol is a promising antitumor agent isolated from dietary ginger (Zingiber officinale). "	( 6-Shogaol induces apoptosis in human leukemia cells through a process involving caspase-mediated cleavage of eIF2α. Gao, N; Li, P; Liu, EH; Liu, Q; Peng, YB; Qi, LW; Zhang, M; Zhou, P, 2013)	1.83
"[6]-shogaol is a vanilloid compound present in steamed ginger (Zingiber officinale), a commonly used spice. "	( [6]-shogaol induces Ca²⁺ signals by activating the TRPV1 channels in the rat insulinoma INS-1E cells. Islam, MS; Rebellato, P, 2014)	1.52
"Shogaols are a group of the active constituents of ginger that have been identified to have various biological activities. "	( 6-Shogaol induces cell cycle arrest and apoptosis in human hepatoma cells through pleiotropic mechanisms. Chen, PS; Chen, YC; Huang, HS; Hung, JH; Lee, KH; Lee, YR; Omar, HA; Teng, YN; Wu, JJ, 2015)	2.58
"[6]-Shogaol is a major bioactive compound identified in ginger that possesses many pharmacological properties."	( [6]-Shogaol, a Novel Chemopreventor in 7,12-Dimethylbenz[a]anthracene-induced Hamster Buccal Pouch Carcinogenesis. Govindhan, A; Kathiresan, S, 2016)	1.47
"6-Shogaol is a potent inhibitor of MDA-MB-231 cell invasion, and the molecular mechanism involves at least in part the down-regulation of MMP-9 transcription by targeting the NF-κB activation cascade. "	( 6-Shogaol, an active constituent of ginger, inhibits breast cancer cell invasion by reducing matrix metalloproteinase-9 expression via blockade of nuclear factor-κB activation. Chew, EH; Chui, WK; Ling, H; Tan, SH; Yang, H, 2010)	1.8
"6-Shogaol is an active compound isolated from Ginger (Zingiber officinale Rosc). "	( 6-Shogaol induces apoptosis in human hepatocellular carcinoma cells and exhibits anti-tumor activity in vivo through endoplasmic reticulum stress. Gao, N; Hu, R; Li, P; Liu, Q; Ma, J; Peng, YB; Qi, LW; Wen, XD; Xu, X; Zhang, L; Zhou, P, 2012)	1.82

Excerpt	Reference	Relevance
"As 6-shogaol has a chemical structure similar to 6-gingerol, we also assessed the effect of 6-shogaol on the viability of gastric cancer cells."	( Ginger ingredients reduce viability of gastric cancer cells via distinct mechanisms. Ando, T; Goto, H; Ishiguro, K; Kadomatsu, K; Maeda, O; Niwa, Y; Ohmiya, N, 2007)	0.79
"6-Shogaol has been shown to possess many antitumor properties including inhibition of cancer cell growth, inhibition of cancer metastasis, induction of apoptosis in cancer cells and induction of cancer cell differentiation. "	( 6-Shogaol inhibits breast and colon cancer cell proliferation through activation of peroxisomal proliferator activated receptor γ (PPARγ). Bradshaw, TD; Kang, O; Khoo, AS; Leong, CO; Mai, CW; Pichika, MR; Tan, BS; Tiong, KH, 2013)	1.83
"6-Shogaol has also recently been shown to have anti-neuroinflammatory effects in lipopolysaccharide (LPS)-treated astrocytes and animal models of Parkinson's disease, LPS-induced inflammation and transient global ischemia."	( 6-Shogaol, an active constituent of ginger, attenuates neuroinflammation and cognitive deficits in animal models of dementia. Choi, JG; Ha, SK; Huh, Y; Kim, HG; Kim, SY; Lee, PK; Moon, M; Oh, H; Oh, MS; Park, Y, 2014)	1.68
"6-Shogaol has exhibited the most potent antioxidant and anti-inflammatory properties which can be attributed to the presence of alpha,beta-unsaturated ketone moiety. "	( Comparative antioxidant and anti-inflammatory effects of [6]-gingerol, [8]-gingerol, [10]-gingerol and [6]-shogaol. Balijepalli, MK; Dugasani, S; Korlakunta, JN; Nadarajah, VD; Pichika, MR; Tandra, S, 2010)	1.3
"Shogaols have been previously reported to induce cancer cell death via multiple mechanisms, among which one analog 6-shogaol has been reported to cause microtubule damage through specific reaction with sulfhydryl groups in tubulin. "	( Shogaols at proapoptotic concentrations induce G(2)/M arrest and aberrant mitotic cell death associated with tubulin aggregation. Ang, X; Chew, EH; Chui, WK; Gan, FF; Ho, OH; Nagle, AA; Tan, SH; Yang, H, 2011)	3.25
"[6]-Shogaol has beneficial effects in spinal neuronal regeneration, but associated molecules and mechanisms are not identified. "	( Protection by [6]-shogaol against lipopolysaccharide-induced toxicity in murine astrocytes is related to production of brain-derived neurotrophic factor. Kim, S; Kwon, J; Kwon, YB; Shim, S, 2012)	1.27
"As 6-shogaol has a chemical structure similar to 6-gingerol, we also assessed the effect of 6-shogaol on the viability of gastric cancer cells."	( Ginger ingredients reduce viability of gastric cancer cells via distinct mechanisms. Ando, T; Goto, H; Ishiguro, K; Kadomatsu, K; Maeda, O; Niwa, Y; Ohmiya, N, 2007)	0.79

Excerpt	Reference	Relevance
"6-Shogaol can inhibit the over activation of Notch pathway and regulate the balance of differentiation between colonic epithelialabsorptive cell line and secretory cell line and repair damaged mucosal tissue."	( [Effects of 6-Shogaol on Notch signaling pathway in colonic epithelial cells of ulcerative colitis mice]. Hui, Y; Li, JT; Shan, YP; Wang, Q; Wei, HL; Yan, SG, 2020)	1.64
"6-Shogaol could suppress cell proliferation and migration, cause cell cycle arrest in the G2/M phase in HeLa and SiHa cells. "	( 6-Shogaol from ginger shows anti-tumor effect in cervical carcinoma via PI3K/Akt/mTOR pathway. Gu, JZ; He, ZL; Jiang, LH; Li, L; Pei, XD; Shi, PZ; Wang, JH; Xiao, JS; Yao, HL, 2021)	2.06
"[6]-shogaol was shown to suppress the release of pro-inflammatory cytokines and decreased the level of inducible nitric oxide syntheses (iNOS), cyclooxygenase-2 (COX-2), and phospho-NF-kB in LPS-treated astrocytes."	( Anti-inflammatory effects of [6]-shogaol: potential roles of HDAC inhibition and HSP70 induction. Choi, DS; Kim, S; Kwon, J; Kwon, YB; Shim, S, 2011)	1.13

Excerpt	Reference	Relevance
"6-Shogaol treatment prevented articular cartilage lesions, synovitis and the presence of pro-inflammatory mediators, and disease markers in osteoarthritis animals. "	( 6-Shogaol (enexasogoal) treatment improves experimental knee osteoarthritis exerting a pleiotropic effect over immune innate signalling responses in chondrocytes. Gratal, P; Herencia, C; Herrero-Beaumont, G; Lamuedra, A; Largo, R; Martín-Santamaría, S; Matamoros-Recio, A; Mediero, A, 2022)	2.16
"Shogaol treated groups received two doses (2mg/kg & 12mg/kg) of Shogaol along with metals and HFD."	( Neuroprotective Effects of Shogaol in Metals (Al, As and Pb) and High-fat diet-induced Neuroinflammation and Behavior in Mice. Ahmed, T; Basri, R; Hameed, A; Ishaq, S; Liaqat, A; Siyar, S, 2023)	1.93
"Shogaol treatment improved BBB integrity."	( Neuroprotective Effects of Shogaol in Metals (Al, As and Pb) and High-fat diet-induced Neuroinflammation and Behavior in Mice. Ahmed, T; Basri, R; Hameed, A; Ishaq, S; Liaqat, A; Siyar, S, 2023)	1.93
"Shogaol treatment showed strong therapeutic potential in metals & HFD induced neuroinflammation and improved cognitive functions; thus, can be considered a potential drug candidate in the future."	( Neuroprotective Effects of Shogaol in Metals (Al, As and Pb) and High-fat diet-induced Neuroinflammation and Behavior in Mice. Ahmed, T; Basri, R; Hameed, A; Ishaq, S; Liaqat, A; Siyar, S, 2023)	2.65
"6-Shogaol pretreatment decreased the activities of cardiac and lipid peroxidative markers and enhanced the antioxidant status in ISO-induced cardiac injury rats."	( 6-Shogaol protects against isoproterenol-induced cardiac injury in rats through attenutating oxidative stress, inflammation, apoptosis and activating nuclear respiratory factor-2/heme oxygenase-1 signaling pathway. Hu, L; Li, H; Luo, W; Shen, J; Zhang, Y, 2022)	2
"6-shogaol Pretreatment effectively improves the above changes in D-GalN-induced rats."	( Preventive Effect of 6-shogaol on D-galactosamine Induced Hepatotoxicity Through NF-?B/MAPK Signaling Pathway in Rats. Ding, Q; Liu, Q; Liu, X; Song, S; Yan, X; Zhang, Y; Zong, X, 2023)	1.78
"Shogaol treatment induced apoptosis and a robust reduction in the levels of the antiapoptotic protein survivin but did not affect the levels of many other apoptosis regulators."	( Shogaol overcomes TRAIL resistance in colon cancer cells via inhibiting of survivin. Hwang, JS; Kwon, KH; Lee, DH; Lee, HC; Oh, SC, 2015)	2.58
"The shogaol-treated group recovered hindlimb reflexes more rapidly and a higher percentage of these rats regained responses compared with the untreated injured rats."	( 6-Shogaol, a natural product, reduces cell death and restores motor function in rat spinal cord injury. Geun, KY; Gon, JH; Ho, KJ; Kyung, KS; Suk, WJ; Sup, JJ, 2006)	1.54

Excerpt	Reference	Relevance
"To investigate the pharmacokinetics of [6]-shogaol, a pungent ingredient of Zingiber officinale Roscoe, the pharmacokinetic parameters were determined by using (14)C-[6]-shogaol (labeled compound) and [6]-shogaol (non-labeled compound)."	( Pharmacokinetics of [6]-shogaol, a pungent ingredient of Zingiber officinale Roscoe (Part I). Aburada, M; Aburada, T; Asami, A; Asano, T; Miyamoto, K; Mizuhara, Y; Shimada, T; Takeda, S, 2010)	0.93
" Pharmacokinetic analysis showed that half-lives of these four analytes and their metabolites were 1-3 h in human plasma."	( Examination of the pharmacokinetics of active ingredients of ginger in humans. Li, X; Sun, D; Wright, B; Yu, Y; Zick, S; Zou, P, 2011)	0.37
" In this context, we have considered the oral supplementation of a highly standardized lipophilic extract combining both above-mentioned phytocomplexes, formulated in attractive softgel capsules, with two objectives: on the one hand to study oral pharmacokinetic of main active extracts' components and on the other hand to examine the immunomodulation and anti-inflammatory properties by gene expression profiling."	( Combined extracts of Echinacea angustifolia DC. and Zingiber officinale Roscoe in softgel capsules: Pharmacokinetics and immunomodulatory effects assessed by gene expression profiling. Agostinis, C; Bulla, R; Dall'Acqua, S; Grabnar, I; Klaric, E; Luidy-Imada, E; Marchionni, L; Perissutti, B; Sut, S; Verardo, R; Voinovich, D, 2019)	0.51
" officinale Roscoe were determined by LC-MS analysis, and the pharmacokinetic analysis was performed."	( Combined extracts of Echinacea angustifolia DC. and Zingiber officinale Roscoe in softgel capsules: Pharmacokinetics and immunomodulatory effects assessed by gene expression profiling. Agostinis, C; Bulla, R; Dall'Acqua, S; Grabnar, I; Klaric, E; Luidy-Imada, E; Marchionni, L; Perissutti, B; Sut, S; Verardo, R; Voinovich, D, 2019)	0.51
" The method for validation following oral administration of ZR and ZRC to rats was proved to be a success in the pharmacokinetic study of the seven ingredients."	( A network pharmacology integrated pharmacokinetics strategy to investigate the pharmacological mechanism of absorbed components from crude and processed Zingiberis Rhizoma on deficiency-cold and hemorrhagic syndrome. Cao, H; Li, J; Li, W; Liu, S; Meng, J; Sun, Y; Wang, S; Zhang, Y, 2023)	0.91

Excerpt	Reference	Relevance
"The model mice were administered with berberine(100 mg·kg~(-1)), 6-shogaol(100 mg·kg~(-1)), and berberine(50 mg·kg~(-1)) combined 6-shogaol(50 mg·kg~(-1)) by gavage, once per day."	( [Experimental study on effects of berberine combined with 6-shogaol on intestinal inflammation and flora in mice with ulcerative colitis]. Chen, ZG; Li, JT; Wei, HL; Yan, SG, 2022)	1.2

Excerpt	Reference	Relevance
" However, the oral bioavailability of [6]-shogaol has been severely limited because of its poor solubility."	( Enhanced oral bioavailability and anti-gout activity of [6]-shogaol-loaded solid lipid nanoparticles. Cao, X; Deng, W; Firempong, CK; Guo, M; Shi, F; Wang, Q; Wei, Q; Xu, X; Yang, Q; Yu, J, 2018)	0.99
" However, its rapid metabolism after oral administration results in poor bioavailability and undetectable in vivo pharmacokinetics."	( Natural-lipid nanoparticle-based therapeutic approach to deliver 6-shogaol and its metabolites M2 and M13 to the colon to treat ulcerative colitis. Lama, S; Merlin, D; Wang, L; Yang, C; Zhang, M, 2020)	0.79
" The results showed that one-third of 6-gingerol was metabolized to produce its reduction metabolites, 6-gingerdiols, and more than 90% of 6-shogaol was metabolized to its phase I and cysteine-conjugated metabolites, suggesting the importance of considering the contribution of these metabolites to the bioavailability and health beneficial effects of gingerols and shogaols."	( Pharmacokinetics of Gingerols, Shogaols, and Their Metabolites in Asthma Patients. DiMango, E; Emala, CW; Sang, S; Saroya, TK; Zhang, S; Zhu, Y, 2022)	1.21

Excerpt	Relevance	Reference
"Cr inhibited the K+ (80 mM)-induced contractions and also shifted the Ca++ dose-response curves to the right, similar to verapamil, indicating Ca++ antagonist activity."	( Cardiovascular effects of ginger aqueous extract and its phenolic constituents are mediated through multiple pathways. Afridi, MB; Ghayur, MN; Gilani, AH; Houghton, PJ, 2005)	0.33
" dosing and can be detected as glucuronide and sulfate conjugates."	( Pharmacokinetics of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol and conjugate metabolites in healthy human subjects. Alrawi, S; Brenner, DE; Djuric, Z; Feng, MR; Litzinger, AJ; Normolle, DP; Ruffin, MT; Zick, SM, 2008)	0.59

Class	Description
monomethoxybenzene	Compounds containing a benzene skeleton substituted with one methoxy group.
phenols	Organic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
enone	An alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Cytochrome P450 3A4	Homo sapiens (human)	IC50 (µMol)	40.8500	0.0001	1.7536	10.0000	AID1443033; AID402936
5-hydroxytryptamine receptor 1A	Homo sapiens (human)	Ki	18.0200	0.0001	0.5326	10.0000	AID480937
Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)	IC50 (µMol)	7.4000	0.0001	1.6847	9.3200	AID345787
Leukotriene A-4 hydrolase	Homo sapiens (human)	IC50 (µMol)	18.5750	0.0005	1.2854	7.6500	AID1337016; AID1337017
Cytochrome P450 2D6	Homo sapiens (human)	IC50 (µMol)	100.0000	0.0000	2.0151	10.0000	AID402937
Transient receptor potential cation channel subfamily A member 1	Rattus norvegicus (Norway rat)	IC50 (µMol)	16.7000	0.4500	3.4243	7.5000	AID644967
Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)	IC50 (µMol)	0.2900	0.0002	0.6060	10.0000	AID644963
[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)
Transient receptor potential cation channel subfamily A member 1	Rattus norvegicus (Norway rat)	EC50 (µMol)	16.0000	0.0600	2.2223	8.4000	AID644966
Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)	EC50 (µMol)	0.3200	0.0005	1.0674	6.3096	AID644962
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
lipid hydroxylation	Cytochrome P450 3A4	Homo sapiens (human)
lipid metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
steroid catabolic process	Cytochrome P450 3A4	Homo sapiens (human)
xenobiotic metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
steroid metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
cholesterol metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
androgen metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
estrogen metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
alkaloid catabolic process	Cytochrome P450 3A4	Homo sapiens (human)
monoterpenoid metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
calcitriol biosynthetic process from calciol	Cytochrome P450 3A4	Homo sapiens (human)
xenobiotic catabolic process	Cytochrome P450 3A4	Homo sapiens (human)
vitamin D metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
vitamin D catabolic process	Cytochrome P450 3A4	Homo sapiens (human)
retinol metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
retinoic acid metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
long-chain fatty acid biosynthetic process	Cytochrome P450 3A4	Homo sapiens (human)
aflatoxin metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
oxidative demethylation	Cytochrome P450 3A4	Homo sapiens (human)
behavioral fear response	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
G protein-coupled receptor signaling pathway	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
adenylate cyclase-inhibiting serotonin receptor signaling pathway	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
serotonin receptor signaling pathway	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
gamma-aminobutyric acid signaling pathway	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
positive regulation of cell population proliferation	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
regulation of serotonin secretion	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
regulation of vasoconstriction	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
exploration behavior	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
regulation of dopamine metabolic process	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
serotonin metabolic process	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
regulation of hormone secretion	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
regulation of behavior	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
chemical synaptic transmission	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
negative regulation of endothelial cell proliferation	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukocyte chemotaxis involved in inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukocyte migration involved in inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukotriene production involved in inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukotriene metabolic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
humoral immune response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of angiogenesis	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukotriene biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
lipoxygenase pathway	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
positive regulation of bone mineralization	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
dendritic cell migration	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
glucose homeostasis	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
long-chain fatty acid biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of fat cell differentiation	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of insulin secretion	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of vascular wound healing	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of wound healing	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of inflammatory response to wounding	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of cytokine production involved in inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of cellular response to oxidative stress	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukotriene A4 biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of reactive oxygen species biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of response to endoplasmic reticulum stress	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of sprouting angiogenesis	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
positive regulation of leukocyte adhesion to arterial endothelial cell	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
lipoxin biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
arachidonic acid metabolic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
lipid oxidation	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
proteolysis	Leukotriene A-4 hydrolase	Homo sapiens (human)
lipid metabolic process	Leukotriene A-4 hydrolase	Homo sapiens (human)
response to zinc ion	Leukotriene A-4 hydrolase	Homo sapiens (human)
leukotriene biosynthetic process	Leukotriene A-4 hydrolase	Homo sapiens (human)
protein metabolic process	Leukotriene A-4 hydrolase	Homo sapiens (human)
peptide catabolic process	Leukotriene A-4 hydrolase	Homo sapiens (human)
response to peptide hormone	Leukotriene A-4 hydrolase	Homo sapiens (human)
type I pneumocyte differentiation	Leukotriene A-4 hydrolase	Homo sapiens (human)
xenobiotic metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
steroid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
cholesterol metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
estrogen metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
coumarin metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
alkaloid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
alkaloid catabolic process	Cytochrome P450 2D6	Homo sapiens (human)
monoterpenoid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
isoquinoline alkaloid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
xenobiotic catabolic process	Cytochrome P450 2D6	Homo sapiens (human)
retinol metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
long-chain fatty acid biosynthetic process	Cytochrome P450 2D6	Homo sapiens (human)
negative regulation of binding	Cytochrome P450 2D6	Homo sapiens (human)
oxidative demethylation	Cytochrome P450 2D6	Homo sapiens (human)
negative regulation of cellular organofluorine metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
arachidonic acid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
thermoception	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
fever generation	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
microglial cell activation	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
diet induced thermogenesis	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
peptide secretion	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
negative regulation of systemic arterial blood pressure	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
lipid metabolic process	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cell surface receptor signaling pathway	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
positive regulation of cytosolic calcium ion concentration	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
chemosensory behavior	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
negative regulation of heart rate	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
negative regulation of mitochondrial membrane potential	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
glutamate secretion	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
calcium-mediated signaling	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cellular response to heat	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
positive regulation of apoptotic process	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
response to peptide hormone	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
positive regulation of nitric oxide biosynthetic process	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
behavioral response to pain	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
sensory perception of mechanical stimulus	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
detection of temperature stimulus involved in thermoception	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
detection of temperature stimulus involved in sensory perception of pain	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of pain	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
protein homotetramerization	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
excitatory postsynaptic potential	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
smooth muscle contraction involved in micturition	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
calcium ion transmembrane transport	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cellular response to alkaloid	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cellular response to ATP	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cellular response to tumor necrosis factor	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cellular response to acidic pH	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cellular response to temperature stimulus	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
negative regulation of establishment of blood-brain barrier	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
calcium ion import across plasma membrane	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
response to capsazepine	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
cellular response to nerve growth factor stimulus	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
monooxygenase activity	Cytochrome P450 3A4	Homo sapiens (human)
steroid binding	Cytochrome P450 3A4	Homo sapiens (human)
iron ion binding	Cytochrome P450 3A4	Homo sapiens (human)
protein binding	Cytochrome P450 3A4	Homo sapiens (human)
steroid hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
retinoic acid 4-hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
oxidoreductase activity	Cytochrome P450 3A4	Homo sapiens (human)
oxygen binding	Cytochrome P450 3A4	Homo sapiens (human)
enzyme binding	Cytochrome P450 3A4	Homo sapiens (human)
heme binding	Cytochrome P450 3A4	Homo sapiens (human)
vitamin D3 25-hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
caffeine oxidase activity	Cytochrome P450 3A4	Homo sapiens (human)
quinine 3-monooxygenase activity	Cytochrome P450 3A4	Homo sapiens (human)
testosterone 6-beta-hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
1-alpha,25-dihydroxyvitamin D3 23-hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
anandamide 8,9 epoxidase activity	Cytochrome P450 3A4	Homo sapiens (human)
anandamide 11,12 epoxidase activity	Cytochrome P450 3A4	Homo sapiens (human)
anandamide 14,15 epoxidase activity	Cytochrome P450 3A4	Homo sapiens (human)
aromatase activity	Cytochrome P450 3A4	Homo sapiens (human)
vitamin D 24-hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
estrogen 16-alpha-hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
estrogen 2-hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
1,8-cineole 2-exo-monooxygenase activity	Cytochrome P450 3A4	Homo sapiens (human)
G protein-coupled serotonin receptor activity	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
protein binding	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
receptor-receptor interaction	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
neurotransmitter receptor activity	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
serotonin binding	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
arachidonate 5-lipoxygenase activity	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
arachidonate 12(S)-lipoxygenase activity	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
iron ion binding	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
protein binding	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
hydrolase activity	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
arachidonate 8(S)-lipoxygenase activity	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
RNA binding	Leukotriene A-4 hydrolase	Homo sapiens (human)
aminopeptidase activity	Leukotriene A-4 hydrolase	Homo sapiens (human)
epoxide hydrolase activity	Leukotriene A-4 hydrolase	Homo sapiens (human)
leukotriene-A4 hydrolase activity	Leukotriene A-4 hydrolase	Homo sapiens (human)
protein binding	Leukotriene A-4 hydrolase	Homo sapiens (human)
peptidase activity	Leukotriene A-4 hydrolase	Homo sapiens (human)
zinc ion binding	Leukotriene A-4 hydrolase	Homo sapiens (human)
tripeptide aminopeptidase activity	Leukotriene A-4 hydrolase	Homo sapiens (human)
metalloaminopeptidase activity	Leukotriene A-4 hydrolase	Homo sapiens (human)
monooxygenase activity	Cytochrome P450 2D6	Homo sapiens (human)
iron ion binding	Cytochrome P450 2D6	Homo sapiens (human)
oxidoreductase activity	Cytochrome P450 2D6	Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen	Cytochrome P450 2D6	Homo sapiens (human)
heme binding	Cytochrome P450 2D6	Homo sapiens (human)
anandamide 8,9 epoxidase activity	Cytochrome P450 2D6	Homo sapiens (human)
anandamide 11,12 epoxidase activity	Cytochrome P450 2D6	Homo sapiens (human)
anandamide 14,15 epoxidase activity	Cytochrome P450 2D6	Homo sapiens (human)
transmembrane signaling receptor activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
extracellular ligand-gated monoatomic ion channel activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
voltage-gated calcium channel activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
calcium channel activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
protein binding	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
calmodulin binding	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
ATP binding	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
intracellularly gated calcium channel activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
chloride channel regulator activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
phosphatidylinositol binding	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
identical protein binding	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
metal ion binding	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
phosphoprotein binding	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
temperature-gated ion channel activity	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
cytoplasm	Cytochrome P450 3A4	Homo sapiens (human)
endoplasmic reticulum membrane	Cytochrome P450 3A4	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 3A4	Homo sapiens (human)
plasma membrane	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
synapse	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
plasma membrane	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
dendrite	5-hydroxytryptamine receptor 1A	Homo sapiens (human)
extracellular region	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
extracellular space	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear envelope	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear envelope lumen	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nucleoplasm	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
cytosol	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear matrix	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear membrane	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
secretory granule lumen	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
perinuclear region of cytoplasm	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
ficolin-1-rich granule lumen	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear envelope	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
extracellular region	Leukotriene A-4 hydrolase	Homo sapiens (human)
nucleoplasm	Leukotriene A-4 hydrolase	Homo sapiens (human)
cytosol	Leukotriene A-4 hydrolase	Homo sapiens (human)
extracellular exosome	Leukotriene A-4 hydrolase	Homo sapiens (human)
tertiary granule lumen	Leukotriene A-4 hydrolase	Homo sapiens (human)
ficolin-1-rich granule lumen	Leukotriene A-4 hydrolase	Homo sapiens (human)
cytosol	Leukotriene A-4 hydrolase	Homo sapiens (human)
nucleus	Leukotriene A-4 hydrolase	Homo sapiens (human)
mitochondrion	Cytochrome P450 2D6	Homo sapiens (human)
endoplasmic reticulum	Cytochrome P450 2D6	Homo sapiens (human)
endoplasmic reticulum membrane	Cytochrome P450 2D6	Homo sapiens (human)
cytoplasm	Cytochrome P450 2D6	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 2D6	Homo sapiens (human)
plasma membrane	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
external side of plasma membrane	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
membrane	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
dendritic spine membrane	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
neuronal cell body	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
postsynaptic membrane	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
plasma membrane	Transient receptor potential cation channel subfamily V member 1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (141)

Assay ID	Title	Year	Journal	Article
AID499783	Activation of phospholipase A2/C in human OC2 cells assessed as decrease in intracellular calcium release at 100 uM in presence of Calcium entry blocker La3+	2010	Journal of natural products, Aug-27, Volume: 73, Issue:8	Effect of [6]-shogaol on cytosolic Ca2+ levels and proliferation in human oral cancer cells (OC2).
AID1269184	Cytotoxicity against rat C6 cells assessed as viable cells at 20 uM by MTT assay	2016	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2	Isolation of bioactive biphenyl compounds from the twigs of Chaenomeles sinensis.
AID1219988	Drug metabolism in human HCT116 cells assessed as 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-one formation at 10 uM after 24 hrs by HPLC-ECD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID499780	Activation of phospholipase A2/C in human OC2 cells assessed as increase in intracellular calcium level at 0.1 uM	2010	Journal of natural products, Aug-27, Volume: 73, Issue:8	Effect of [6]-shogaol on cytosolic Ca2+ levels and proliferation in human oral cancer cells (OC2).
AID1220000	Cytotoxicity against human HCT116 cells assessed as growth inhibition after 24 hrs by MTT assay	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID480944	Inhibition of human MDR1 expressed in MDCK cells assessed as fluorescence activity at 30 uM after 1.5 hrs by rhodamine 123 efflux test	2010	Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9	Identification of serotonin 5-HT1A receptor partial agonists in ginger.
AID1220002	Induction of apoptosis in human HCT116 cells assessed as apoptotic cells at 10 uM after 24 hrs by TUNEL assay	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1427106	Inhibition of TGFbeta1-induced epithelial-mesenchymal transition in human SNU182 cells assessed as reduction in MMP9 mRNA expression at 12.5 uM preincubated for 2 hrs followed by TGFbeta1 addition measured after 48 hrs by qRT-PCR method	2017	Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4	Combined treatment with zingerone and its novel derivative synergistically inhibits TGF-β1 induced epithelial-mesenchymal transition, migration and invasion of human hepatocellular carcinoma cells.
AID1219976	Drug excretion in C57BL/6J mouse feces assessed as 3',4'-dihydroxyphenyl-decan-3-one formation at 200 mg/kg, po by HPLC-ECD analysis relative to control	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1291762	Cytotoxicity in rat C6 cells assessed as cell viability at 20 uM after 24 hrs by MTT assay	2016	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 26, Issue:8	Bioactive lignan constituents from the twigs of Sambucus williamsii.
AID1219984	Drug metabolism in C57BL/6J mouse plasma assessed as glucuronidated form of metabolite formation at 200 mg/kg, po after 2 to 4 hrs by HPLC-ECD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID480941	Antagonist activity at 5HT1A receptor expressed in HEK293 cells assessed as inhibition of 8-OH-DPAT-induced [S35]GTPgammaS binding by scintillation counting	2010	Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9	Identification of serotonin 5-HT1A receptor partial agonists in ginger.
AID1219978	Drug excretion in C57BL/6J mouse feces assessed as 5-methylthio-1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-one formation at 200 mg/kg, po by HPLC analysis relative to control	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1525282	Cytotoxicity against rat C6 cells assessed as cell viability at 20 uM after 24 hrs by MTT assay relative to control	2019	Journal of natural products, 05-24, Volume: 82, Issue:5	Securinega Alkaloids from the Twigs of Securinega suffruticosa and Their Biological Activities.
AID480938	Displacement of [3H]8-OH-DPAT from 5HT1A receptor expressed in HEK293 cells at 25 ug/ml after 2 hrs by liquid scintillation counting	2010	Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9	Identification of serotonin 5-HT1A receptor partial agonists in ginger.
AID1055975	Induction of NGF secretion in rat C6 cells at 10 uM after 24 hrs by ELISA relative to control	2013	Journal of natural products, Nov-22, Volume: 76, Issue:11	Bioactive lignans from the trunk of Abies holophylla.
AID1219964	Drug recovery in C57BL/6J mouse urine assessed as sulfated form of metabolite formation at 200 mg/kg, po by LC/MS analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1337015	Selectivity index, ratio of IC50 for human TIG1 cells to IC50 for human HCT116 cells	2017	Bioorganic & medicinal chemistry, 02-01, Volume: 25, Issue:3	Synthesis, docking, cytotoxicity, and LTA
AID421747	Antiallergic activity in mIgE-DNP and DNP-BSA-stimulated rat RBL2H3 cells assessed as inhibition of beta-hexosaminidase release at 100 uM pretreated before mIgE-DNP challenge measured after 24 hrs relative to control	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID421737	Cytotoxicity against rat RBL2H3 cells after 12 hrs by MTT assay	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID1219968	Antioxidant activity assessed as DPPH radical scavenging activity	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID421745	Antiallergic activity in mIgE-DNP and DNP-BSA-stimulated rat RBL2H3 cells assessed as inhibition of beta-hexosaminidase release at 1 uM pretreated before mIgE-DNP challenge measured after 24 hrs relative to control	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID1219983	Drug recovery in C57BL/6J mouse urine assessed as sulfated form of metabolite formation at 200 mg/kg, po by HPLC-ECD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1295871	Cytotoxicity in rat C6 cells assessed as cell viability at 20 uM after 24 hrs by MTT assay	2016	Journal of natural products, Feb-26, Volume: 79, Issue:2	Diterpenes from the Trunk of Abies holophylla and Their Potential Neuroprotective and Anti-inflammatory Activities.
AID1219982	Drug recovery in C57BL/6J mouse urine assessed as glucuronidated form of metabolite formation at 200 mg/kg, po by HPLC-ECD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1219970	Drug excretion in C57BL/6J mouse feces assessed as 5-cysteinyl-[6]-shogaol formation at 200 mg/kg, po by HPLC-ECD analysis relative to control	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1433345	Induction of nerve growth factor secretion in rat C6 cells at 20 uM after 24 hrs by ELISA relative to control	2016	Journal of natural products, 10-28, Volume: 79, Issue:10	Wasabisides A-E, Lignan Glycosides from the Roots of Wasabia japonica.
AID1443021	Inhibition of CYP2B6 in human liver microsomes using bupropion as substrate preincubated for 10 mins followed by NADPH addition measured after 20 mins	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Effects of 6-paradol, an unsaturated ketone from gingers, on cytochrome P450-mediated drug metabolism.
AID1866679	Neuroprotective activity in rat C6 cells assessed as NGF secretion level at 25 uM measured after 24 hrs by ELISA	2022	Journal of natural products, 04-22, Volume: 85, Issue:4	Procyanidins and Phlobatannins from the Twigs of
AID1337014	Cytotoxicity against human HF19 cells assessed as reduction in cell viability after 48 hrs by WST1 assay	2017	Bioorganic & medicinal chemistry, 02-01, Volume: 25, Issue:3	Synthesis, docking, cytotoxicity, and LTA
AID1525281	Neuroprotective activity in rat C6 cells assessed as NGF secretion at 20 uM after 24 hrs by ELISA relative to control	2019	Journal of natural products, 05-24, Volume: 82, Issue:5	Securinega Alkaloids from the Twigs of Securinega suffruticosa and Their Biological Activities.
AID1219955	Induction of apoptosis in human HCT116 cells assessed as apoptotic cells at 20 uM after 24 hrs by TUNEL assay	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1427086	Inhibition of TGFbeta1-induced epithelial-mesenchymal transition in human SNU182 cells assessed as reduction in downregulation of E-cadherin expression at 12.5 uM preincubated for 2 hrs followed by TGFbeta1 addition measured after 48 hrs by Western blot m	2017	Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4	Combined treatment with zingerone and its novel derivative synergistically inhibits TGF-β1 induced epithelial-mesenchymal transition, migration and invasion of human hepatocellular carcinoma cells.
AID1219997	Drug metabolism in mouse CL-13 cells assessed as 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-ol formation at 10 uM after 24 hrs by HPLC-ECD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1866680	Cytotoxicity against rat C6 cells assessed as cell viability at 25 uM by MTT assay	2022	Journal of natural products, 04-22, Volume: 85, Issue:4	Procyanidins and Phlobatannins from the Twigs of
AID1219971	Drug excretion in C57BL/6J mouse feces assessed as 2-((2R)-2-amino-3-(3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-5-ylthio)propanamido)acetic acid formation at 200 mg/kg, po by HPLC-ECD analysis relative to control	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID499790	Cytotoxicity in human OC2 cells assessed as decrease in cell viability after 24 hrs by crystal violate assay	2010	Journal of natural products, Aug-27, Volume: 73, Issue:8	Effect of [6]-shogaol on cytosolic Ca2+ levels and proliferation in human oral cancer cells (OC2).
AID1443033	Inhibition of recombinant human CYP3A4 expressed in baculosomes using Vivid BOMR substrate red measured every 30 sec for 30 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Effects of 6-paradol, an unsaturated ketone from gingers, on cytochrome P450-mediated drug metabolism.
AID1443023	Inhibition of CYP2C9 in human liver microsomes using diclofenac as substrate preincubated for 10 mins followed by NADPH addition measured after 7 mins	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Effects of 6-paradol, an unsaturated ketone from gingers, on cytochrome P450-mediated drug metabolism.
AID1219956	Induction of apoptosis in human H1299 cells assessed as apoptotic cells at 20 uM after 24 hrs by TUNEL assay	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1161579	Inhibition of human recombinant AChE using acetylthiocholine iodide as substrate at 10 uM preincubated for 20 mins before substrate addition by Ellman method	2014	Bioorganic & medicinal chemistry, Oct-01, Volume: 22, Issue:19	Shogaol-huprine hybrids: dual antioxidant and anticholinesterase agents with β-amyloid and tau anti-aggregating properties.
AID1501258	Induction of NGF secretion in rat C6 cells at 20 uM after 24 hrs by ELISA relative to control	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Iridoid Glycosides from the Twigs of Sambucus williamsii var. coreana and Their Biological Activities.
AID1443022	Inhibition of CYP2C8 in human liver microsomes using amodiaquin as substrate preincubated for 10 mins followed by NADPH addition measured after 10 mins	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Effects of 6-paradol, an unsaturated ketone from gingers, on cytochrome P450-mediated drug metabolism.
AID644961	Agonist activity at human TRPV1 ion channel expressed in HEK293 cells assessed as calcium influx by fluo-4-Am-based fluorimetry relative to ionomycin	2012	Bioorganic & medicinal chemistry letters, Feb-15, Volume: 22, Issue:4	Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators.
AID1161573	Antioxidant activity assessed as ABTS free radical scavenging activity measured as trolox equivalent after 1 hr by spectrophotometry	2014	Bioorganic & medicinal chemistry, Oct-01, Volume: 22, Issue:19	Shogaol-huprine hybrids: dual antioxidant and anticholinesterase agents with β-amyloid and tau anti-aggregating properties.
AID1443037	Inhibition of CYP2C9 in human liver microsomes using tolbutamide as substrate by HPLC analysis	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Effects of 6-paradol, an unsaturated ketone from gingers, on cytochrome P450-mediated drug metabolism.
AID1604257	Growth inhibition of human HepG2 cells	2019	European journal of medicinal chemistry, Dec-01, Volume: 183	Recent advances in α,β-unsaturated carbonyl compounds as mitochondrial toxins.
AID1219969	Drug excretion in C57BL/6J mouse feces assessed as (2R)-2-amino-3-(3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-5-ylthio)propanoic acid formation at 200 mg/kg, po by HPLC-ECD analysis relative to control	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID421754	Antiallergic activity in mIgE-DNP and DNP-BSA-stimulated rat RBL2H3 cells assessed as inhibition of beta-hexosaminidase release at 50 uM pretreated before mIgE-DNP challenge measured after 24 to 48 hrs relative to control	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID499782	Activation of phospholipase A2/C in human OC2 cells assessed as increase in intracellular calcium level at 100 uM in presence of thapsigargin	2010	Journal of natural products, Aug-27, Volume: 73, Issue:8	Effect of [6]-shogaol on cytosolic Ca2+ levels and proliferation in human oral cancer cells (OC2).
AID1427080	Growth inhibition of human SNU182 cells at <12.5 uM after 48 hrs by CCK8 assay	2017	Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4	Combined treatment with zingerone and its novel derivative synergistically inhibits TGF-β1 induced epithelial-mesenchymal transition, migration and invasion of human hepatocellular carcinoma cells.
AID345787	Inhibition of 5LOX	2008	Bioorganic & medicinal chemistry, Dec-15, Volume: 16, Issue:24	Characterization of novel furan compounds on the basis of their radical scavenging activity and cytoprotective effects against glutamate- and lipopolysaccharide-induced insults.
AID1443028	Inhibition of CYP2E1 in human liver microsomes using chlorzoxazone as substrate preincubated for 10 mins followed by NADPH addition measured after 20 mins	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Effects of 6-paradol, an unsaturated ketone from gingers, on cytochrome P450-mediated drug metabolism.
AID1161574	Antioxidant activity assessed as DPPH free radical scavenging activity measured as trolox equivalent after 30 mins by spectrophotometry	2014	Bioorganic & medicinal chemistry, Oct-01, Volume: 22, Issue:19	Shogaol-huprine hybrids: dual antioxidant and anticholinesterase agents with β-amyloid and tau anti-aggregating properties.
AID1443039	Inhibition of CYP2E1 in human liver microsomes using chlorzoxazone as substrate by HPLC analysis	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Effects of 6-paradol, an unsaturated ketone from gingers, on cytochrome P450-mediated drug metabolism.
AID402937	Inhibition of human CYP2D6 by radiometric assay	2004	Journal of natural products, Jul, Volume: 67, Issue:7	Sesquiterpenes and flavonol glycosides from Zingiber aromaticum and their CYP3A4 and CYP2D6 inhibitory activities.
AID1220001	Cytotoxicity against human H1299 cells assessed as growth inhibition after 24 hrs by MTT assay	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID345785	Inhibition of COX1	2008	Bioorganic & medicinal chemistry, Dec-15, Volume: 16, Issue:24	Characterization of novel furan compounds on the basis of their radical scavenging activity and cytoprotective effects against glutamate- and lipopolysaccharide-induced insults.
AID1427083	Growth inhibition of human SNU182 cells assessed as cell survival at 12.5 uM after 48 hrs by CCK8 assay relative to control	2017	Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4	Combined treatment with zingerone and its novel derivative synergistically inhibits TGF-β1 induced epithelial-mesenchymal transition, migration and invasion of human hepatocellular carcinoma cells.
AID1443038	Inhibition of CYP2C19 in human liver microsomes using (S)-mephenytoin as substrate by HPLC analysis	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Effects of 6-paradol, an unsaturated ketone from gingers, on cytochrome P450-mediated drug metabolism.
AID1219965	Drug metabolism in C57BL/6J mouse plasma assessed as glucuronidated form of metabolite formation at 200 mg/kg, po after 2 to 4 hrs by LC/MS analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID421753	Antiallergic activity in mIgE-DNP and DNP-BSA-stimulated rat RBL2H3 cells assessed as inhibition of beta-hexosaminidase release at 10 uM pretreated before mIgE-DNP challenge measured after 24 to 48 hrs relative to control	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID402936	Inhibition of human CYP3A4 by radiometric assay	2004	Journal of natural products, Jul, Volume: 67, Issue:7	Sesquiterpenes and flavonol glycosides from Zingiber aromaticum and their CYP3A4 and CYP2D6 inhibitory activities.
AID1527555	Inhibition of NLRP3 inflammasome activation in LPS-primed human THP1 cells assessed as reduction in IL-1beta level at 20 uM preincubated for 1 hr followed by addition of ATP and measured after 3 hrs by ELISA method relative to control	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Development of small molecule inhibitors targeting NLRP3 inflammasome pathway for inflammatory diseases.
AID1443027	Inhibition of CYP2D6 in human liver microsomes using dextromethorphan as substrate preincubated for 10 mins followed by NADPH addition measured after 15 mins	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Effects of 6-paradol, an unsaturated ketone from gingers, on cytochrome P450-mediated drug metabolism.
AID499785	Activation of phospholipase A2/C in human OC2 cells assessed as increase in intracellular calcium level in presence of phospholipase-A2 inhibitor aristolochc acid	2010	Journal of natural products, Aug-27, Volume: 73, Issue:8	Effect of [6]-shogaol on cytosolic Ca2+ levels and proliferation in human oral cancer cells (OC2).
AID499781	Activation of phospholipase A2/C in human OC2 cells assessed as increase in intracellular calcium level at 100 uM	2010	Journal of natural products, Aug-27, Volume: 73, Issue:8	Effect of [6]-shogaol on cytosolic Ca2+ levels and proliferation in human oral cancer cells (OC2).
AID1200096	Inhibition of Brugia malayi thymidylate kinase using dTMP substrate by spectrophotometric assay	2015	European journal of medicinal chemistry, Mar-26, Volume: 93	Synthesis, molecular docking and Brugia malayi thymidylate kinase (BmTMK) enzyme inhibition study of novel derivatives of [6]-shogaol.
AID480937	Displacement of [3H]8-OH-DPAT from 5HT1A receptor expressed in HEK293 cells after 2 hrs by liquid scintillation counting	2010	Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9	Identification of serotonin 5-HT1A receptor partial agonists in ginger.
AID421746	Antiallergic activity in mIgE-DNP and DNP-BSA-stimulated rat RBL2H3 cells assessed as inhibition of beta-hexosaminidase release at 1 uM pretreated before mIgE-DNP challenge measured after 48 hrs relative to control	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID1219973	Drug excretion in C57BL/6J mouse feces assessed as 5-N-acetylcysteinyl-[6]-shogaol formation at 200 mg/kg, po by HPLC-ECD analysis relative to control	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1219980	Drug excretion in C57BL/6J mouse feces assessed as 5-methylthio-1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-ol formation at 200 mg/kg, po by HPLC-ECD analysis relative to control	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID499789	Activation of phospholipase A2/C in human OC2 cells assessed as increase in intracellular calcium level at 100 uM pretreated with phospholipase C inhibitor U7322 and ATP	2010	Journal of natural products, Aug-27, Volume: 73, Issue:8	Effect of [6]-shogaol on cytosolic Ca2+ levels and proliferation in human oral cancer cells (OC2).
AID1337013	Cytotoxicity against human TIG1 cells assessed as reduction in cell viability after 48 hrs by WST1 assay	2017	Bioorganic & medicinal chemistry, 02-01, Volume: 25, Issue:3	Synthesis, docking, cytotoxicity, and LTA
AID421748	Antiallergic activity in mIgE-DNP and DNP-BSA-stimulated rat RBL2H3 cells assessed as inhibition of beta-hexosaminidase release at 100 uM pretreated before mIgE-DNP challenge measured after 48 hrs relative to control	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID644962	Agonist activity at human TRPV1 ion channel expressed in HEK293 cells assessed as calcium influx by fluo-4-Am-based fluorimetry	2012	Bioorganic & medicinal chemistry letters, Feb-15, Volume: 22, Issue:4	Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators.
AID421750	Antiallergic activity in mIgE-DNP and DNP-BSA-stimulated rat RBL2H3 cells assessed as inhibition of beta-hexosaminidase release at 200 uM pretreated before mIgE-DNP challenge measured after 48 hrs relative to control	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID421752	Antiallergic activity in mIgE-DNP and DNP-BSA-stimulated rat RBL2H3 cells assessed as inhibition of beta-hexosaminidase release at 5 uM pretreated before mIgE-DNP challenge measured after 48 hrs	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID1443036	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate by HPLC analysis	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Effects of 6-paradol, an unsaturated ketone from gingers, on cytochrome P450-mediated drug metabolism.
AID1427084	Growth inhibition of human SNU182 cells after 48 hrs by CCK8 assay	2017	Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4	Combined treatment with zingerone and its novel derivative synergistically inhibits TGF-β1 induced epithelial-mesenchymal transition, migration and invasion of human hepatocellular carcinoma cells.
AID1220003	Induction of apoptosis in human H1299 cells assessed as apoptotic cells at 10 uM after 24 hrs by TUNEL assay	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1617010	Cytotoxicity against rat C6 cells assessed as cell viability at 20 uM incubated for 24 hrs by MTT assay relative to control	2019	Journal of natural products, 11-22, Volume: 82, Issue:11	Thiohydantoin and Hydantoin Derivatives from the Roots of
AID1295878	Neuroprotective activity in H2O2 treated rat astrocytes assessed as induction of NGF release at 10 uM preincubated for 1 hr followed by H2O2 treatment for 24 hrs	2016	Journal of natural products, Feb-26, Volume: 79, Issue:2	Diterpenes from the Trunk of Abies holophylla and Their Potential Neuroprotective and Anti-inflammatory Activities.
AID1161576	Inhibition of aggregation of amyloid beta (1 to 42) (unknown origin) expressed in Escherichia coli BL21 (DE3) at 10 uM after 24 hrs by thioflavin S fluorescence assay	2014	Bioorganic & medicinal chemistry, Oct-01, Volume: 22, Issue:19	Shogaol-huprine hybrids: dual antioxidant and anticholinesterase agents with β-amyloid and tau anti-aggregating properties.
AID1219977	Drug excretion in C57BL/6J mouse feces assessed as 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-ol formation at 200 mg/kg, po by HPLC-ECD analysis relative to control	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1161577	Inhibition of aggregation of TAU (unknown origin) expressed in Escherichia coli BL21 (DE3) at 10 uM after 24 hrs by thioflavin S fluorescence assay	2014	Bioorganic & medicinal chemistry, Oct-01, Volume: 22, Issue:19	Shogaol-huprine hybrids: dual antioxidant and anticholinesterase agents with β-amyloid and tau anti-aggregating properties.
AID1443026	Inhibition of CYP2A6 in human liver microsomes using Coumarin as substrate preincubated for 10 mins followed by NADPH addition measured after 15 mins	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Effects of 6-paradol, an unsaturated ketone from gingers, on cytochrome P450-mediated drug metabolism.
AID156507	Effective dose to protect PC12 cells from beta-Amyloid (BA) insult was determined using MTT reduction assay	2004	Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5	Side-chain length is important for shogaols in protecting neuronal cells from beta-amyloid insult.
AID1219987	Drug metabolism in human HCT116 cells assessed as 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-ol formation at 10 uM after 24 hrs by HPLC-ECD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1219986	Drug metabolism in human HCT116 cells assessed as 1-(4'-hydroxy-3'-methoxyphenyl)-4-decen-3-ol formation at 10 uM after 24 hrs by HPLC-ECD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID644966	Agonist activity at rat TRPA1 ion channel expressed in HEK293 cells assessed as calcium influx by fluo-4-Am-based fluorimetry	2012	Bioorganic & medicinal chemistry letters, Feb-15, Volume: 22, Issue:4	Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators.
AID421739	Cytotoxicity against rat RBL2H3 cells at 120 uM after 12 hrs by MTT assay	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID1364711	Cytotoxicity in rat C6 cells assessed as cell viability at 20 uM incubated for 24 hrs by MTT assay relative to untreated control	2017	Journal of natural products, 04-28, Volume: 80, Issue:4	Bioactive Triterpenoids from the Twigs of Chaenomeles sinensis.
AID1219975	Drug excretion in C57BL/6J mouse feces assessed as 5-methoxy-1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-one formation at 200 mg/kg, po by HPLC-ECD analysis relative to control	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1427088	Inhibition of TGFbeta1-induced epithelial-mesenchymal transition in human SNU182 cells assessed as reduction in upregulation of Snail expression at 12.5 uM preincubated for 2 hrs followed by TGFbeta1 addition measured after 48 hrs by Western blot method	2017	Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4	Combined treatment with zingerone and its novel derivative synergistically inhibits TGF-β1 induced epithelial-mesenchymal transition, migration and invasion of human hepatocellular carcinoma cells.
AID1364710	Neuroprotective activity in rat C6 cells assessed as induction of nerve growth factor secretion at 20 uM incubated for 24 hrs by ELISA method relative to untreated control	2017	Journal of natural products, 04-28, Volume: 80, Issue:4	Bioactive Triterpenoids from the Twigs of Chaenomeles sinensis.
AID1219991	Drug metabolism in human HT-29 cells assessed as 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-ol formation at 10 uM by HPLC-ECD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID421749	Antiallergic activity in mIgE-DNP and DNP-BSA-stimulated rat RBL2H3 cells assessed as inhibition of beta-hexosaminidase release at 200 uM pretreated before mIgE-DNP challenge measured after 24 hrs relative to control	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID480942	Antagonist activity at 5HT1A receptor expressed in HEK293 cells assessed as inhibition of serotonin-induced [S35]GTPgammaS binding by scintillation counting	2010	Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9	Identification of serotonin 5-HT1A receptor partial agonists in ginger.
AID1446623	Neuroprotective activity in rat C6 cells assessed as NGF secretion at 20 uM after 24 hrs by ELISA relative to control	2017	Journal of natural products, 02-24, Volume: 80, Issue:2	Anti-Neurodegenerative Biflavonoid Glycosides from Impatiens balsamina.
AID1337016	Inhibition of recombinant C-terminal His-tagged human LTA4H aminopeptidase activity expressed in Escherichia coli using L-alanine-4-nitro-anilide hydrochloride as substrate preincubated for 20 mins followed by substrate addition	2017	Bioorganic & medicinal chemistry, 02-01, Volume: 25, Issue:3	Synthesis, docking, cytotoxicity, and LTA
AID1337017	Inhibition of recombinant C-terminal His-tagged human LTA4H epoxide hydrolase activity expressed in Escherichia coli assessed as reduction in LTB4 production using LTA4 as substrate preincubated for 20 mins followed by substrate addition measured after 30	2017	Bioorganic & medicinal chemistry, 02-01, Volume: 25, Issue:3	Synthesis, docking, cytotoxicity, and LTA
AID499791	Activation of calcium channel in human OC2 cells assessed as increase in intracellular calcium efflux in presence of La3+	2010	Journal of natural products, Aug-27, Volume: 73, Issue:8	Effect of [6]-shogaol on cytosolic Ca2+ levels and proliferation in human oral cancer cells (OC2).
AID1219963	Drug recovery in C57BL/6J mouse urine assessed as glucuronidated form of metabolite formation at 200 mg/kg, po by LC/MS analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1439509	Antihelmintic activity against Hymenolepis nana	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Medicinal plants used as anthelmintics: Ethnomedical, pharmacological, and phytochemical studies.
AID1443020	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate preincubated for 10 mins followed by NADPH addition measured after 10 mins	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Effects of 6-paradol, an unsaturated ketone from gingers, on cytochrome P450-mediated drug metabolism.
AID644963	Antagonist activity at human TRPV1 ion channel expressed in HEK293 cells assessed as inhibition of capsaicin-induced calcium influx incubated for 5 mins prior to capsicin-induction by fluo-4-AM-based fluorimetry	2012	Bioorganic & medicinal chemistry letters, Feb-15, Volume: 22, Issue:4	Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators.
AID1443025	Inhibition of CYP3A4 in human liver microsomes using testosterone as substrate preincubated for 10 mins followed by NADPH addition measured after 10 mins	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Effects of 6-paradol, an unsaturated ketone from gingers, on cytochrome P450-mediated drug metabolism.
AID345786	Inhibition of COX2	2008	Bioorganic & medicinal chemistry, Dec-15, Volume: 16, Issue:24	Characterization of novel furan compounds on the basis of their radical scavenging activity and cytoprotective effects against glutamate- and lipopolysaccharide-induced insults.
AID1161580	Inhibition of human serum BChE using butyrylthiocholine iodide at 10 uM preincubated for 20 mins before substrate addition by Ellman method	2014	Bioorganic & medicinal chemistry, Oct-01, Volume: 22, Issue:19	Shogaol-huprine hybrids: dual antioxidant and anticholinesterase agents with β-amyloid and tau anti-aggregating properties.
AID1291763	Neuroprotective activity in rat C6 cells assessed as NGF secretion at 20 uM after 24 hrs by ELISA	2016	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 26, Issue:8	Bioactive lignan constituents from the twigs of Sambucus williamsii.
AID499786	Activation of phospholipase A2/C in human OC2 cells assessed as increase in intracellular calcium level at 100 uM in presence of PKA inhibitor H89	2010	Journal of natural products, Aug-27, Volume: 73, Issue:8	Effect of [6]-shogaol on cytosolic Ca2+ levels and proliferation in human oral cancer cells (OC2).
AID1617009	Neuroprotective activity in rat C6 cells assessed as NGF secretion at 20 uM incubated for 24 hrs by ELISA relative to control	2019	Journal of natural products, 11-22, Volume: 82, Issue:11	Thiohydantoin and Hydantoin Derivatives from the Roots of
AID644967	Antagonist activity at rat TRPA1 ion channel expressed in HEK293 cells assessed as inhibition of AITC-induced calcium influx incubated for 5 mins prior to AITC-induction by fluo-4-AM-based fluorimetry	2012	Bioorganic & medicinal chemistry letters, Feb-15, Volume: 22, Issue:4	Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators.
AID1337012	Cytotoxicity against human HCT116 cells assessed as reduction in cell viability after 48 hrs by WST1 assay	2017	Bioorganic & medicinal chemistry, 02-01, Volume: 25, Issue:3	Synthesis, docking, cytotoxicity, and LTA
AID644964	Agonist activity at rat TRPA1 ion channel expressed in HEK293 cells assessed as calcium influx by fluo-4-Am-based fluorimetry relative to allyl isothiocyanate	2012	Bioorganic & medicinal chemistry letters, Feb-15, Volume: 22, Issue:4	Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators.
AID1443029	Inhibition of CYP3A4 in human liver microsomes using midazolam as substrate preincubated for 10 mins followed by NADPH addition measured after 5 mins	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Effects of 6-paradol, an unsaturated ketone from gingers, on cytochrome P450-mediated drug metabolism.
AID1219992	Drug metabolism in human HT-29 cells assessed as 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-one formation at 10 uM by HPLC-ECD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1219985	Drug metabolism in C57BL/6J mouse plasma assessed as sulfated form of metabolite formation at 200 mg/kg, po after 2 to 4 hrs by HPLC analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1515004	Anti-inflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced nitric oxide production pretreated followed by LPS-stimulation by griess assay	2019	Bioorganic & medicinal chemistry letters, 01-15, Volume: 29, Issue:2	Synthesis and anti-neuroinflammatory activity of N-heterocyclic analogs based on natural biphenyl-neolignan honokiol.
AID1161575	Antioxidant activity assessed as total polyphenolics measured as gallic acid equivalent after 30 mins by Folin-Ciocalteu assay	2014	Bioorganic & medicinal chemistry, Oct-01, Volume: 22, Issue:19	Shogaol-huprine hybrids: dual antioxidant and anticholinesterase agents with β-amyloid and tau anti-aggregating properties.
AID1161578	Permeability of the compound by PAMPA-BBB assay	2014	Bioorganic & medicinal chemistry, Oct-01, Volume: 22, Issue:19	Shogaol-huprine hybrids: dual antioxidant and anticholinesterase agents with β-amyloid and tau anti-aggregating properties.
AID1228333	Neuroprotective activity in rat C6 cells assessed as stimulation of NGF release at 20 uM after 24 hrs by ELISA relative to control	2015	Journal of natural products, May-22, Volume: 78, Issue:5	Lignan Glycosides from the Twigs of Chaenomeles sinensis and Their Biological Activities.
AID1219995	Drug metabolism in human H1299 cells assessed as 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-one formation at 10 uM after 24 hrs by HPLC-ECD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1446624	Cytotoxicity against rat C6 cells assessed as cell viability at 20 uM after 24 hrs by MTT assay relative to control	2017	Journal of natural products, 02-24, Volume: 80, Issue:2	Anti-Neurodegenerative Biflavonoid Glycosides from Impatiens balsamina.
AID1501259	Cytotoxicity against rat C6 cells assessed as cell viability at 20 uM after 24 hrs by MTT assay relative to control	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Iridoid Glycosides from the Twigs of Sambucus williamsii var. coreana and Their Biological Activities.
AID91529	Effective dose to protect IMR-32 cells from beta-Amyloid (BA) insult was determined using MTT reduction assay	2004	Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5	Side-chain length is important for shogaols in protecting neuronal cells from beta-amyloid insult.
AID1219974	Drug excretion in C57BL/6J mouse feces assessed as 1-(4'-hydroxy-3'-methoxyphenyl)-4-decen-3-ol formation at 200 mg/kg, po by HPLC-ECD analysis relative to control	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID499788	Activation of phospholipase A2/C in human OC2 cells assessed as increase in intracellular calcium level at 100 uM in presence of PKC inhibitor GF109203X	2010	Journal of natural products, Aug-27, Volume: 73, Issue:8	Effect of [6]-shogaol on cytosolic Ca2+ levels and proliferation in human oral cancer cells (OC2).
AID499787	Activation of phospholipase A2/C in human OC2 cells assessed as increase in intracellular calcium level at 100 uM in presence of phospholipase C activator PMA	2010	Journal of natural products, Aug-27, Volume: 73, Issue:8	Effect of [6]-shogaol on cytosolic Ca2+ levels and proliferation in human oral cancer cells (OC2).
AID1269183	Stimulation of NGF secretion in rat C6 cells at 20 uM after 24 hrs by ELISA	2016	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2	Isolation of bioactive biphenyl compounds from the twigs of Chaenomeles sinensis.
AID1219979	Drug excretion in C57BL/6J mouse feces assessed as 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-one formation at 200 mg/kg, po by HPLC analysis relative to control	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID421751	Antiallergic activity in mIgE-DNP and DNP-BSA-stimulated rat RBL2H3 cells assessed as inhibition of beta-hexosaminidase release at 5 uM pretreated before mIgE-DNP challenge measured after 24 hrs	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID1219998	Drug metabolism in mouse CL-13 cells assessed as 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-one formation at 10 uM by HPLC-ECD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1219966	Drug metabolism in C57BL/6J mouse plasma assessed as sulfated form of metabolite formation at 200 mg/kg, po after 2 to 4 hrs by LC/MS analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1427104	Inhibition of TGFbeta1-induced epithelial-mesenchymal transition in human SNU182 cells assessed as reduction in MMP2 mRNA expression at 12.5 uM preincubated for 2 hrs followed by TGFbeta1 addition measured after 48 hrs by qRT-PCR method	2017	Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4	Combined treatment with zingerone and its novel derivative synergistically inhibits TGF-β1 induced epithelial-mesenchymal transition, migration and invasion of human hepatocellular carcinoma cells.
AID1433346	Cytotoxicity against rat C6 cells assessed as cell viability at 20 uM by MTT assay relative to control	2016	Journal of natural products, 10-28, Volume: 79, Issue:10	Wasabisides A-E, Lignan Glycosides from the Roots of Wasabia japonica.
AID1219994	Drug metabolism in human H1299 cells assessed as 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-ol formation at 10 uM after 24 hrs by HPLC-ECD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1219972	Drug excretion in C57BL/6J mouse feces assessed as (2R)-2-acetamido-3-(3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-5-ylthio)propanoic acid formation at 200 mg/kg, po by HPLC-ECD analysis relative to control	2012	Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4	Metabolism of [6]-shogaol in mice and in cancer cells.
AID1356587	Neuroprotective activity in rat C6 cells assessed as induction of nerve growth factor secretion at 20 uM measured after 24 hrs by ELISA relative to control	2018	Journal of natural products, 08-24, Volume: 81, Issue:8	Structural Characterization of Terpenoids from Abies holophylla Using Computational and Statistical Methods and Their Biological Activities.
AID1356589	Cytotoxicity against rat C6 cells assessed as cell viability at 20 uM measured after 24 hrs by MTT assay relative to control	2018	Journal of natural products, 08-24, Volume: 81, Issue:8	Structural Characterization of Terpenoids from Abies holophylla Using Computational and Statistical Methods and Their Biological Activities.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	11 (3.74)	18.7374
1990's	9 (3.06)	18.2507
2000's	34 (11.56)	29.6817
2010's	174 (59.18)	24.3611
2020's	66 (22.45)	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	4 (1.34%)	5.53%
Reviews	15 (5.03%)	6.00%
Case Studies	1 (0.34%)	4.05%
Observational	0 (0.00%)	0.25%
Other	278 (93.29%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
dinitrochlorobenzene Dinitrochlorobenzene: A skin irritant that may cause dermatitis of both primary and allergic types. Contact sensitization with DNCB has been used as a measure of cellular immunity. DNCB is also used as a reagent for the detection and determination of pyridine compounds.. 1-chloro-2,4-dinitrobenzene : A C-nitro compound that is chlorobenzene carrying a nitro substituent at each of the 2- and 4-positions.	2.13	1	0	C-nitro compound; monochlorobenzenes	allergen; epitope; sensitiser
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	3.25	1	0	catechols; dihydroxybenzoic acid	antineoplastic agent; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; human xenobiotic metabolite; plant metabolite
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	1.97	1	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	2.13	1	0	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	2.25	1	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	2.13	1	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.01	1	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	2.1	1	0	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
guaiacol Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.	6.31	19	0	guaiacols	disinfectant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; expectorant; plant metabolite
diacetyl butane-2,3-dione : An alpha-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation.	2.6	1	0	alpha-diketone	Escherichia coli metabolite; Saccharomyces cerevisiae metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	2.6	1	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.54	2	0	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	2.6	1	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.41	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.41	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	1.98	1	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	2.05	1	0	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
1-aminobenzotriazole [no description available]	2.08	1	0
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source. PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish.	2.21	1	0	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	7.41	1	0	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
albendazole [no description available]	2.05	1	0	aryl sulfide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	anthelminthic drug; microtubule-destabilising agent; tubulin modulator
berberine [no description available]	7.41	1	0	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	2.97	4	0	aromatic ether; nitrile; polyether; tertiary amino compound
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	2.21	1	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
cilostazol [no description available]	2.01	1	0	lactam; tetrazoles	anticoagulant; bronchodilator agent; EC 3.1.4.17 (3',5'-cyclic-nucleotide phosphodiesterase) inhibitor; fibrin modulating drug; neuroprotective agent; platelet aggregation inhibitor; vasodilator agent
cimetidine Cimetidine: A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.. cimetidine : A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach.	2.1	1	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
cisapride Cisapride: A substituted benzamide used for its prokinetic properties. It is used in the management of gastroesophageal reflux disease, functional dyspepsia, and other disorders associated with impaired gastrointestinal motility. (Martindale The Extra Pharmacopoeia, 31st ed). cisapride : The amide resulting from formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with cis-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-amine. It has been used (as its monohydrate or as its tartrate) for the treatment of gastro-oesophageal reflux disease and for non-ulcer dyspepsia, but its propensity to cause cardiac arrhythmias resulted in its complete withdrawal from many countries, including the U.K., and restrictions on its use elsewhere.	2.01	1	0	benzamides
clonidine Clonidine: An imidazoline sympatholytic agent that stimulates ALPHA-2 ADRENERGIC RECEPTORS and central IMIDAZOLINE RECEPTORS. It is commonly used in the management of HYPERTENSION.. clonidine (amino form) : A clonidine that is 4,5-dihydro-1H-imidazol-2-amine in which one of the amino hydrogens is replaced by a 2,6-dichlorophenyl group.	2.1	1	0	clonidine; imidazoline
desipramine Desipramine: A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.. desipramine : A dibenzoazepine consisting of 10,11-dihydro-5H-dibenzo[b,f]azepine substituted on nitrogen with a 3-(methylamino)propyl group.	2.1	1	0	dibenzoazepine; secondary amino compound	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; cholinergic antagonist; drug allergen; EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; serotonin uptake inhibitor
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	2.72	2	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	3.35	1	0	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	2.03	1	0	carboxamidine; guanidines; one-carbon compound
hexobarbital Hexobarbital: A barbiturate that is effective as a hypnotic and sedative.. hexobarbital : A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups.	1.96	1	0	barbiturates
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.	2.1	1	0	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	2.05	1	0	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	7.41	1	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
ketanserin Ketanserin: A selective serotonin receptor antagonist with weak adrenergic receptor blocking properties. The drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation. It is well tolerated and is particularly effective in older patients.. ketanserin : A member of the class of quinazolines that is quinazoline-2,4(1H,3H)-dione which is substituted at position 3 by a 2-[4-(p-fluorobenzoyl)piperidin-1-yl]ethyl group.	1.97	1	0	aromatic ketone; organofluorine compound; piperidines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; cardiovascular drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
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.	2.02	1	0	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
lomefloxacin lomefloxacin: structure given in first source. lomefloxacin : A fluoroquinolone antibiotic, used (generally as the hydrochloride salt) to treat bacterial infections including bronchitis and urinary tract infections. It is also used to prevent urinary tract infections prior to surgery.	2.1	1	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antimicrobial agent; antitubercular agent; photosensitizing agent
mefenamic acid Mefenamic Acid: A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase.. mefenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis.	3.35	1	0	aminobenzoic acid; secondary amino compound	analgesic; antipyretic; antirheumatic drug; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
nicardipine Nicardipine: A potent calcium channel blockader with marked vasodilator action. It has antihypertensive properties and is effective in the treatment of angina and coronary spasms without showing cardiodepressant effects. It has also been used in the treatment of asthma and enhances the action of specific antineoplastic agents.. nicardipine : A racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension.. 2-[benzyl(methyl)amino]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate : A dihydropyridine that is 1,4-dihydropyridine substituted by a methyl, {2-[benzyl(methyl)amino]ethoxy}carbonyl, 3-nitrophenyl, methoxycarbonyl and methyl groups at positions 2, 3, 4, 5 and 6, respectively.	2.05	1	0	benzenes; C-nitro compound; diester; dihydropyridine; methyl ester; tertiary amino compound
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2.05	1	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
masoprocol nordihydroguaretic acid: antioxidant compound found in the creosote bush (Larrea tridentata)	2.04	1	0	catechols; lignan; tetrol	antioxidant; ferroptosis inhibitor; geroprotector; plant metabolite
norfloxacin Norfloxacin: A synthetic fluoroquinolone (FLUOROQUINOLONES) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA GYRASE.. norfloxacin : A quinolinemonocarboxylic acid with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase.	2.1	1	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug; DNA synthesis inhibitor; environmental contaminant; xenobiotic
ofloxacin Ofloxacin: A synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA GYRASE, halting DNA REPLICATION.. 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid : An oxazinoquinoline that is 2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one substituted by methyl, carboxy, fluoro, and 4-methylpiperazin-1-yl groups at positions 3, 6, 9, and 10, respectively.. ofloxacin : A racemate comprising equimolar amounts of levofloxacin and dextrofloxacin. It is a synthetic fluoroquinolone antibacterial agent which inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.	2.1	1	0	3-oxo monocarboxylic acid; N-arylpiperazine; N-methylpiperazine; organofluorine compound; oxazinoquinoline
phloretin [no description available]	2.13	1	0	dihydrochalcones	antineoplastic agent; plant metabolite
pindolol Pindolol: A moderately lipophilic beta blocker (ADRENERGIC BETA-ANTAGONISTS). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638). pindolol : A member of the class of indols which is the 2-hydroxy-3-(isopropylamino)propyl ether derivative of 1H-indol-4-ol.	1.97	1	0	indoles; secondary amine	antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist; serotonergic antagonist; vasodilator agent
prazosin Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.. prazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.	1.98	1	0	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
promazine Promazine: A phenothiazine with actions similar to CHLORPROMAZINE but with less antipsychotic activity. It is primarily used in short-term treatment of disturbed behavior and as an antiemetic.. promazine : A phenothiazine deriative in which the phenothiazine tricycle has a 3-(dimethylaminopropyl) group at the N-10 position.	2.1	1	0	phenothiazines; tertiary amine	antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; muscarinic antagonist; phenothiazine antipsychotic drug; serotonergic antagonist
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	1.98	1	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
stearic acid octadecanoic acid : A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.	2.17	1	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	3.59	2	0	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
corticosterone [no description available]	2.1	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
pilocarpine Pilocarpine: A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.. (+)-pilocarpine : The (+)-enantiomer of pilocarpine.	2.6	1	0	pilocarpine	antiglaucoma drug
diethylnitrosamine Diethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties.. N-nitrosodiethylamine : A nitrosamine that is N-ethylethanamine substituted by a nitroso group at the N-atom.	2.07	1	0	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	2.41	1	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	2.13	1	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
allyl isothiocyanate allyl isothiocyanate: used in the manufacture of flavors, war gases; medical use as a counterirritant; structure. allyl isothiocyanate : An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152degreeC, it is responsible for the pungent taste of mustard, horseradish, and wasabi.	2.07	1	0	alkenyl isothiocyanate; isothiocyanate	antimicrobial agent; antineoplastic agent; apoptosis inducer; lachrymator; metabolite
physostigmine Physostigmine: A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.	2.04	1	0	carbamate ester; indole alkaloid	antidote to curare poisoning; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	3.98	2	1	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	2.13	1	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
ficusin Ficusin: A naturally occurring furocoumarin, found in PSORALEA. After photoactivation with UV radiation, it binds DNA via single and double-stranded cross-linking.. psoralen : The simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia.	3.25	1	0	psoralens	plant metabolite
mannitol [no description available]	3.51	1	1	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	2.04	1	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2.1	1	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
methylethyl ketone methylethyl ketone: solvent; colorless synthetic resins, smokeless powders; may be irritating to eyes, mucous membranes; may be toxic in high concentrations; structure. butanone : Any ketone that is butane substituted by an oxo group at unspecified position.. butan-2-one : A dialkyl ketone that is a four-carbon ketone carrying a single keto- group at position C-2.	2.41	1	0	butanone; dialkyl ketone; methyl ketone; volatile organic compound	bacterial metabolite; polar aprotic solvent
alpha-pinene [no description available]	2.07	1	0	pinene	plant metabolite
pyocyanine Pyocyanine: Antibiotic pigment produced by Pseudomonas aeruginosa.. pyocyanine : An iminium betaine that is 5-methylphenazin-5-ium which is substituted at position 1 by an oxidanidyl group. An antibiotic pigment produced by Pseudomonas aeruginosa.	2.1	1	0	iminium betaine; phenazines	antibacterial agent; bacterial metabolite; biological pigment; virulence factor
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	3.25	1	0	monoterpenoid; phenols	volatile oil component
uvitex swn Uvitex SWN: optical brightner from Ciba; structure	3.25	1	0	7-aminocoumarins	fluorochrome
methyleugenol methyleugenol: structure	3.25	1	0	phenylpropanoid
4-cymene 4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.	3.25	1	0	monoterpene; toluenes	human urinary metabolite; plant metabolite; volatile oil component
allyl alcohol allyl alcohol: structure. allylic alcohol : An alcohol where the hydroxy group is attached to a saturated carbon atom adjacent to a double bond (R groups may be H, organyl, etc.).. allyl alcohol : A propenol in which the C=C bond connects C-2 and C-3. It is has been found in garlic (Allium sativum). Formerly used as a herbicide for the control of various grass and weed seeds.	6.98	1	0	primary allylic alcohol; propenol	antibacterial agent; fungicide; herbicide; insecticide; plant metabolite
desaspidin desaspidin: structure	3.25	1	0
anthracene acene : A polycyclic aromatic hydrocarbon consisting of fused benzene rings in a rectilinear arrangement.. acenes : Polycyclic aromatic hydrocarbons consisting of fused benzene rings in a rectilinear arrangement and their substitution derivatives.	7.17	1	0	acene; anthracenes; ortho-fused tricyclic hydrocarbon
estragole estragole : A phenylpropanoid that is chavicol in which the hydroxy group is replaced by a methoxy group.	3.25	1	0	alkenylbenzene; monomethoxybenzene; phenylpropanoid	carcinogenic agent; flavouring agent; genotoxin; insect attractant; plant metabolite
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2.1	1	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
n-heptane Heptanes: Seven-carbon alkanes with the formula C7H16.. heptane : A straight-chain alkane with seven carbon atoms. It has been found in Jeffrey pine (Pinus jeffreyi).	2.39	2	0	alkane; volatile organic compound	non-polar solvent; plant metabolite
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	7.54	2	0	catechin	antioxidant; plant metabolite
thymidine monophosphate Thymidine Monophosphate: 5-Thymidylic acid. A thymine nucleotide containing one phosphate group esterified to the deoxyribose moiety.. dTMP : The neutral species of thymidine 5'-monophosphate (2'-deoxythymidine 5'-monophosphate).	2.11	1	0	thymidine 5'-monophosphate	fundamental metabolite
berbamine [no description available]	3.21	1	0	phenylpropanoid
plumbagin plumbagin: a superoxide anion generator. plumbagin : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.	3.61	2	0	hydroxy-1,4-naphthoquinone; phenols	anticoagulant; antineoplastic agent; immunological adjuvant; metabolite
oleanolic acid [no description available]	3.25	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
syringic acid syringic acid: RN given refers to parent cpd; structure in third source. syringic acid : A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid.	2.13	1	0	benzoic acids; dimethoxybenzene; phenols	plant metabolite
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.13	1	0	dialdehyde	biomarker
violacein [no description available]	2.1	1	0
beta-phellandrene [no description available]	2.07	1	0	phellandrene	plant metabolite
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	3.11	4	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
vinblastine [no description available]	2.05	1	0
deoxycytidine [no description available]	2.1	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	2.43	2	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	7.42	2	0	D-galactosamine; primary amino compound	toxin
copper sulfate Copper Sulfate: A sulfate salt of copper. It is a potent emetic and is used as an antidote for poisoning by phosphorus. It also can be used to prevent the growth of algae.. copper(II) sulfate : A metal sulfate compound having copper(2+) as the metal ion.	2.01	1	0	metal sulfate	emetic; fertilizer; sensitiser
barium chloride barium chloride: RN given refers to parent cpd. barium chloride : The inorganic dichloride salt of barium.	2.01	1	0	barium salt; inorganic chloride	potassium channel blocker
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.47	2	0	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
7-oxodehydroabietic acid 7-oxodehydroabietic acid: RN refers to (1R-(1alpha,4beta,10aalpha))-isomer; structure given in first source	2.13	1	0
zingerone zingerone: pungent principle of ginger; structure. zingerone : A methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.	10.28	9	0	methyl ketone; monomethoxybenzene; phenols	anti-inflammatory agent; antiemetic; antioxidant; flavouring agent; fragrance; plant metabolite; radiation protective agent
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.1	1	0	benzenes; phenyl acetates
azoxymethane Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.	2.41	1	0
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	2.25	1	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
etoposide [no description available]	3.4	6	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
substance p [no description available]	9.3	4	1	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
diltiazem Diltiazem: A benzothiazepine derivative with vasodilating action due to its antagonism of the actions of CALCIUM ion on membrane functions.. diltiazem : A 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate in which both stereocentres have S configuration. A calcium-channel blocker and vasodilator, it is used as the hydrochloride in the management of angina pectoris and hypertension.	2.05	1	0	5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate	antihypertensive agent; calcium channel blocker; vasodilator agent
gemcitabine gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.	7.1	1	0	organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; environmental contaminant; immunosuppressive agent; photosensitizing agent; prodrug; radiosensitizing agent; xenobiotic
irinotecan [no description available]	7.25	1	0	carbamate ester; delta-lactone; N-acylpiperidine; pyranoindolizinoquinoline; ring assembly; tertiary alcohol; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 5.99.1.2 (DNA topoisomerase) inhibitor; prodrug
ursolic acid [no description available]	3.25	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
betulinic acid [no description available]	3.65	2	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-HIV agent; anti-inflammatory agent; antimalarial; antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; plant metabolite
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	2.13	1	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	2.08	1	0	1,2,3-triazole
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.	3.25	1	0	(2S)-flavan-4-one; dihydroxyflavanone	antineoplastic agent; antioxidant; metabolite; neuroprotective agent; vasodilator agent
ubenimex ubenimex: growth inhibitor	2.15	1	0
4-o-methyl-12-o-tetradecanoylphorbol 13-acetate [no description available]	2.05	1	0
magnolol [no description available]	1.98	1	0	biphenyls
honokiol [no description available]	2.44	2	0	biphenyls
Tormentic acid tormentic acid: aglycone of Rosamultin	2.15	1	0	triterpenoid	metabolite
gliclazide 18alpha-glycyrrhetinic acid: a gap junction inhibitor	2.08	1	0
maslinic acid (2Alpha,3beta)-2,3-dihydroxyolean-12-en-28-oic acid: from Luehea divaricata and Agrimonia eupatoria	2.15	1	0	dihydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory agent; antineoplastic agent; antioxidant; plant metabolite
alpha-curcumene alpha-curcumene: active priniciple in essential oils of Curcuma xanthorrhiza. alpha-curcumene : A sesquiterpene that is 2-methyl-2-heptene in which one of the hydrogens at position 6 is substituted by a p-tolyl group.	2.07	1	0	sesquiterpene
6-paradol 6-paradol: induces apoptosis; structure in first source	9.63	7	0	ketone; monomethoxybenzene; phenols
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.	2.13	1	0	abietane diterpenoid; carbotricyclic compound; monocarboxylic acid	allergen; metabolite
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	2.17	1	0	D-glucuronic acid	algal metabolite
u 73122 1-(6-((3-methoxyestra-1,3,5(10)-trien-17-yl)amino)hexyl)-1H-pyrrole-2,5-dione: structure given in first source. U-73122 : An aza-steroid that is 3-O-methyl-17beta-estradiol in which the 17beta-hydroxy group is replaced by a 6-(maleimid-1-yl)hexylamino group. An inibitor of phospholipase C.	2.05	1	0	aromatic ether; aza-steroid; maleimides	EC 3.1.4.11 (phosphoinositide phospholipase C) inhibitor
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	2.07	1	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
aspidin bb [no description available]	3.25	1	0
imatinib mesylate imatinib methanesulfonate : A methanesulfonate (mesylate) salt that is the monomesylate salt of imatinib. Used for treatment of chronic myelogenous leukemia and gastrointestinal stromal tumours.	2.31	1	0	methanesulfonate salt	anticoronaviral agent; antineoplastic agent; apoptosis inducer; tyrosine kinase inhibitor
gefitinib [no description available]	7.6	1	0	aromatic ether; monochlorobenzenes; monofluorobenzenes; morpholines; quinazolines; secondary amino compound; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist
n(6)-carboxymethyllysine N(6)-carboxymethyllysine: RN given refers to (L)-isomer; structure given in first source. N(6)-carboxymethyl-L-lysine : An L-lysine derivative with a carboxymethyl substituent at the N(6)-position.	2.13	1	0	L-lysine derivative; non-proteinogenic L-alpha-amino acid	antigen
gr 65630 GR 65630: serotonin receptor ligand. GR 65630 : A member of the class of methylindoles that is 1-methylindole substituted at position 3 by a 3-(4-methylimidazol-5-yl)propanoyl group.	2.03	1	0
4-amino-1-(6-chloro-2-pyridyl)piperidine hydrochloride 4-amino-1-(6-chloro-2-pyridyl)piperidine hydrochloride: has high affinity and selectivity for 5-HT3 receptors; structure given in first source	2.03	1	0
omega-n-methylarginine omega-N-Methylarginine: A competitive inhibitor of nitric oxide synthetase.. N(omega)-methyl-L-arginine : A L-arginine derivative with a N(omega)-methyl substituent.	5.2	13	0	amino acid zwitterion; arginine derivative; guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid
4-methoxyhonokiol 4-methoxyhonokiol: an NSAID isolated from Magnolia obovata; structure in first source	2.21	1	0
ampelopsin ampelopsin: hepatoprotective agent; isolated from Hovenia dulcis; RN given for (2R-trans)-isomer; structure in first source. (+)-dihydromyricetin : An optically active form of dihydromyricetin having (2R,3R)-configuration.	2.15	1	0	dihydromyricetin; secondary alpha-hydroxy ketone	antineoplastic agent; antioxidant; metabolite
gingerdione gingerdione: structure given in first source	2.95	4	0	beta-diketone; monomethoxybenzene; phenols
methylinositol methylinositol: from Ebenus haussknechtii; structure in first source. pinitol : A cyclitol ether formed by etherification of the 3-hydroxy group of chiro-inositol. It is plant metabolite isolated from the leaves of Sutherlandia frutescens.. 1D-4-O-methyl-myo-inositol : A member of the class of methyl myo-inositols that is cyclohexane-1,2,3,4,5-pentol substituted by a methoxy group at position 6 (the 1R,2S,3S,4S,5S,6S-isomer).. D-pinitol : The D-enantiomer of pinitol.	3.25	1	0
8-gingerol 8-gingerol: isolated from Zingiber officinale	4.04	13	0	beta-hydroxy ketone; monomethoxybenzene; phenols
10-gingerol [no description available]	4.28	5	0	beta-hydroxy ketone; monomethoxybenzene; phenols
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	2.4	2	0
medioresinol medioresinol: has both leishmanicidal and antifungal activities; isolated from Sambucus williamsii; structure in first source. (-)-medioresinol : A lignan that is tetrahydro-1H,3H-furo[3,4-c]furan substituted by a 4-hydroxy-3,5-dimethoxyphenyl group at position 1 and a 4-hydroxy-3-methoxyphenyl group at position 4. It has been isolated from the stems of Sinocalamus affinis.	2.13	1	0	dimethoxybenzene; furofuran; lignan; polyphenol	plant metabolite
spirobrassinin spirobrassinin: structure in first source	2.21	1	0
pimaric acid pimaric acid: RN given refers to (D)-isomer; structure	2.17	1	0	diterpenoid
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.	2.02	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C29-steroid; phytosterols; stigmastane sterol	anticholesteremic drug; antioxidant; mouse metabolite; plant metabolite; sterol methyltransferase inhibitor
lupeol [no description available]	3.25	1	0	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory drug; plant metabolite
lariciresinol lariciresinol: found in human urine. (+)-lariciresinol : A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer).	2.13	1	0	aromatic ether; lignan; oxolanes; phenols; primary alcohol	antifungal agent; plant metabolite
pomolic acid pomolic acid: from Rosa woodsii & Hyptis capitata; structure in first source	3.25	1	0	triterpenoid	metabolite
inositol 1,4,5-trisphosphate Inositol 1,4,5-Trisphosphate: Intracellular messenger formed by the action of phospholipase C on phosphatidylinositol 4,5-bisphosphate, which is one of the phospholipids that make up the cell membrane. Inositol 1,4,5-trisphosphate is released into the cytoplasm where it releases calcium ions from internal stores within the cell's endoplasmic reticulum. These calcium ions stimulate the activity of B kinase or calmodulin.	2.05	1	0	myo-inositol trisphosphate	mouse metabolite
quinidine Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.	2.02	1	0	cinchona alkaloid	alpha-adrenergic antagonist; anti-arrhythmia drug; antimalarial; drug allergen; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; muscarinic antagonist; P450 inhibitor; potassium channel blocker; sodium channel blocker
limonene-1,2-epoxide limonene-1,2-epoxide: RN given refers to cpd without isomeric designation. (4R)-limonene 1,2-epoxide : The (R)-enantiomer of limonene 1,2-epoxide.	3.25	1	0	limonene 1,2-epoxide
aucuparin aucuparin: biphenyl phytoalexin in Sorbus aucuparia cell cultures; structure in first source	2.13	1	0	biphenyls
gingerol gingerol: an active ingredient in GINGER along with SHOGAOL. a nonvolatile methoxy phenyl decanone. gingerol : A beta-hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4-hydroxy-3-methoxyphenyl moiety at position 1; believed to inhibit adipogenesis. It is a constituent of fresh ginger.	13.57	118	4	beta-hydroxy ketone; guaiacols	antineoplastic agent; plant metabolite
securinine securinine: a quinolizine pseudoalkaloid (not from amino acid) from Securinega suffurutiosa or Securinini nitras	2.21	1	0	indolizines
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	1.98	1	0
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	2.4	2	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
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.	2.17	1	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	2.54	2	0	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
thapsigargin Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.	2.05	1	0	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
prostaglandin d2 Prostaglandin D2: The principal cyclooxygenase metabolite of arachidonic acid. It is released upon activation of mast cells and is also synthesized by alveolar macrophages. Among its many biological actions, the most important are its bronchoconstrictor, platelet-activating-factor-inhibitory, and cytotoxic effects.. prostaglandin D2 : A member of the class of prostaglandins D that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,9alpha,13E,15S- stereoisomer).	2.08	1	0	prostaglandins D	human metabolite; mouse metabolite
conidendrin conidendrin: RN given for (3aR-(3aalpha,4alpha,9alpha,9abeta))-isomer; a phenyl-naphthyl-furanolactone	2.08	1	0	lignan	metabolite
cinnamaldehyde 3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.	3.25	1	0	3-phenylprop-2-enal; cinnamaldehydes	antifungal agent; EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor; flavouring agent; hypoglycemic agent; plant metabolite; sensitiser; vasodilator agent
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.	2.13	1	0	4-coumaric acid	food component; mouse metabolite; plant metabolite
anethole anethole: an isomer of estragole; structurally similar to CAPSAICIN; has some neurological and insecticidal and skin absorption effects; RN given refers to unspecified stereoisomer. anethole : A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.. trans-anethole : The trans-stereoisomer of anethole.	3.25	1	0	anethole	flavouring agent
glycosides [no description available]	2.6	1	0
piperine piperine : A N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum.	2.1	1	0	benzodioxoles; N-acylpiperidine; piperidine alkaloid; tertiary carboxamide	food component; human blood serum metabolite; NF-kappaB inhibitor; plant metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.5	2	0	stilbene
isoliquiritigenin [no description available]	3.31	1	0	chalcones	antineoplastic agent; biological pigment; EC 1.14.18.1 (tyrosinase) inhibitor; GABA modulator; geroprotector; metabolite; NMDA receptor antagonist
xanthohumol xanthohumol: from hop plant, Humulus lupulus. xanthohumol : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells.	3.31	1	0	aromatic ether; chalcones; polyphenol	anti-HIV-1 agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor; metabolite
gw9662 2-chloro-5-nitrobenzanilide: pretreatment of peroxisome proliferator activated receptors with GW9662 results in the irreversible loss of ligand binding	2.15	1	0	benzamides
tropisetron Tropisetron: An indole derivative and 5-HT3 RECEPTOR antagonist that is used for the prevention of nausea and vomiting.. tropisetron : An indolyl carboxylate ester obtained by formal condensation of the carboxy group of indole-3-carboxylic acid with the hydroxy group of tropine.	2.03	1	0	indolyl carboxylic acid
sesquiterpenes [no description available]	3.64	2	0
3,4-methylenedioxy-beta-nitrostyrene 3,4-methylenedioxy-beta-nitrostyrene: tyrosine kinase inhibitor that prevents platelet glycoprotein IIb/IIIa activation; structure in first source	3.35	1	0
rhododendrol rhododendrol: structure in first source	2.25	1	0
sclareolide [no description available]	2.17	1	0	naphthofuran
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	5.19	8	0	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
hc 030031 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)-N-(4-isopropylphenyl)acetamide: a TRPA1 channel blocker	2.41	1	0
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	3.26	6	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	2.07	1	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
capsazepine capsazepine: modified capsaicin molecule; a capsaicin receptor antagonist. capsazepine : A benzazepine that is 2,3,4,5-tetrahydro-1H-2-benzazepine which is substituted by hydroxy groups at positions 7 and 8 and on the nitrogen atom by a 2-(p-chlorophenyl)ethylaminothiocarbonyl group. A synthetic analogue of capsaicin, it was the first reported capsaicin receptor antagonist.	2.1	1	0	benzazepine; catechols; monochlorobenzenes; thioureas	capsaicin receptor antagonist
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.76	3	0
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	3.61	2	0
quercetin [no description available]	2.15	1	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.94	4	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	1.97	1	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse 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.	3.35	1	0	trihydroxyflavone	antineoplastic agent; metabolite
thromboxane a2 Thromboxane A2: An unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).. thromboxane A2 : A thromboxane which is produced by activated platelets and has prothrombotic properties: it stimulates activation of new platelets as well as increases platelet aggregation.	1.96	1	0	epoxy monocarboxylic acid; thromboxanes A	mouse metabolite
5-hydroxy-6,8,11,14-eicosatetraenoic acid 5(S)-HETE : A HETE having a (5S)-hydroxy group and (6E)-, (8Z)-, (11Z)- and (14Z)-double bonds.. 5-HETE : A HETE having a 5-hydroxy group and (6E)-, (8Z)-, (11Z)- and (14Z)-double bonds.	1.96	1	0	HETE	human metabolite; mouse metabolite
quercetin 3-o-glucopyranoside quercetin 3-O-glucopyranoside: structure in first source. quercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells	2.15	1	0	beta-D-glucoside; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; antipruritic drug; bone density conservation agent; geroprotector; histamine antagonist; osteogenesis regulator; plant metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.15	1	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
3-methylkaempferol 3-methylkaempferol: structure in first source. 3-methoxyapigenin : A trihydroxyflavone that is apigenin substituted by a methoxy group at position 3.	2.02	1	0	monomethoxyflavone; trihydroxyflavone	plant metabolite
kaempferol [no description available]	2.15	1	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
genistein [no description available]	3.25	1	0	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
pyrantel pamoate Pyrantel Pamoate: Broad spectrum antinematodal anthelmintic used also in veterinary medicine.	1.97	1	0	organic molecular entity
lutein Lutein: A xanthophyll found in the major LIGHT-HARVESTING PROTEIN COMPLEXES of plants. Dietary lutein accumulates in the MACULA LUTEA.. xanthophyll : A subclass of carotenoids consisting of the oxygenated carotenes.	2.15	1	0	carotenol	food colouring; plant metabolite
chrysin chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.	3.25	1	0	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
pterostilbene [no description available]	2.5	2	0	diether; methoxybenzenes; stilbenol	anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; hypoglycemic agent; neuroprotective agent; neurotransmitter; plant metabolite; radical scavenger
gingerenone a gingerenone A: has antineoplastic activity; isolated from Zingiber officinale; structure in first source	3.9	3	0	diarylheptanoid
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.	3.21	1	0	aromatic ketone; benzenetriol; chromenol; enone; methyl ketone	anti-allergic agent; antihypertensive agent; antineoplastic agent; apoptosis inducer; K-ATP channel agonist; metabolite
astragalin kaempferol-3-O-glucoside: isolated from the pit of Mahkota dewa; structure in first source. kaempferol 3-O-beta-D-glucoside : A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage.	2.15	1	0	beta-D-glucoside; kaempferol O-glucoside; monosaccharide derivative; trihydroxyflavone	plant metabolite; trypanocidal drug
tocotrienol, alpha alpha-tocotrienol : A tocotrienol that is chroman-6-ol substituted by methyl groups at positions 2, 5, 7 and 8 and a farnesyl chain at position 2. It has been found in palm oil derived from Elaeis guineensis.	2.04	1	0	tocotrienol; vitamin E	ferroptosis inhibitor; human metabolite; neuroprotective agent; plant metabolite
15-deoxy-delta(12,14)-prostaglandin j2 15-deoxy-delta(12,14)-prostaglandin J2: 15-deoxy-PGJ2 is also available; check for double bonds (indicated by delta) at 12 and 14 positions. 15-deoxy-Delta(12,14)-prostaglandin J2 : A prostaglandin J derivative comprising prostaglandin J2 lacking the 15-hydroxy group and having C=C double bonds at the 12- and 14-positions.	2.08	1	0	prostaglandins J	electrophilic reagent; insulin-sensitizing drug; metabolite
kaempferol 3-o-rhamnoside kaempferol 3-O-rhamnoside: from apple (Malus domestica) leaves; structure in first source. afzelin : A glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage.	2.02	1	0	glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	anti-inflammatory agent; antibacterial agent; plant metabolite
hexahydrocurcumin hexahydrocurcumin: from Zingiber officinale; structure in first source	7.46	2	0	diarylheptanoid
kaempferol 3-o-neohesperidoside kaempferol 3-O-neohesperidoside: isolated from Daphniphyllum calycinum; structure in first source	2.15	1	0	flavonoids; glycoside
kaempferol-3-o-rutinoside kaempferol-3-O-rutinoside: isolated from the methanolic extract of the whole plants of Diodia teres through repeated silica gel and Sephadex LH-20 column chromatography; structure in first source. kaempferol-3-rutinoside : A kaempferol O-glucoside that is kaempferol attached to a rutinosyl [6-deoxy-alpha-L-mannosyl-(1->6)-beta-D-glucosyl] residue at position 3 via a glycosidic linkage. It has been isolated from the leaves of Solanum campaniforme.	2.15	1	0	disaccharide derivative; kaempferol O-glucoside; rutinoside; trihydroxyflavone	metabolite; plant metabolite; radical scavenger
licochalcone a licochalcone A: has both anti-inflammatory and antineoplastic activities; structure given in first source; isolated from root of Glycyrrhiza inflata; RN given refers to (E)-isomer	3.31	1	0	chalcones
ermanin ermanin: from Tanacetum microphyllum; structure given in first source. 3,4'-dimethylkaempferol : A dimethoxyflavone that is kaempferol in which the hydroxy groups at position 3 and 4' have been replaced by methoxy groups. It is a component of bee glue and isolated from several plant species including Tanacetum microphyllum.	2.02	1	0	dihydroxyflavone; dimethoxyflavone	anti-inflammatory agent; antimycobacterial drug; antineoplastic agent; apoptosis inducer; plant metabolite
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	2.6	1	0	carbon group element atom; elemental lead; metal atom	neurotoxin
bay 11-7082 (E)-3-tosylacrylonitrile : A nitrile that is acrylonitrile in which the hydrogen located beta,trans to the cyano group is replaced by a tosyl group. It is an inhibitor of cytokine-induced IkappaB-alpha phosphorylation in cells.	3.35	1	0	nitrile; sulfone	apoptosis inducer; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; non-steroidal anti-inflammatory drug; platelet aggregation inhibitor
methyl-3-methoxy-4-hydroxystyryl ketone methyl-3-methoxy-4-hydroxystyryl ketone: structure given in first source; RN given refers to cpd without isomeric designation	2	1	0	hydroxycinnamic acid
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	2.6	1	0	boron group element atom; elemental aluminium; metal atom
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	2.6	1	0	metalloid atom; pnictogen	micronutrient
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	2.66	2	0	chalcogen; nonmetal atom	macronutrient
2',4'-dihydroxychalcone 2',4'-dihydroxychalcone: RN given refers to (E)-isomer; RN for cpd without isomeric designation not available 6/89; structure given in first source	3.31	1	0
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	3.49	7	0	cysteinium	fundamental metabolite
zerumbone zerumbone: RN given for (E,E,E)-isomer; structure in first source. zerumbone : A sesquiterpenoid and cyclic ketone that is (1E,4E,8E)-alpha-humulene which is substituted by an oxo group at the carbon atom attached to two double bonds. It is obtained by steam distillation from a type of edible ginger, Zingiber zerumbet Smith, grown particularly in southeast Asia.	3.58	2	0	cyclic ketone; sesquiterpenoid	anti-inflammatory agent; glioma-associated oncogene inhibitor; plant metabolite
resiniferatoxin resiniferatoxin: phorbol related diterpene ester; potent agonist of vanilloid TRPV1 receptors. resiniferatoxin : A heteropentacyclic compound found in Euphorbia poissonii with molecular formula C37H40O9. It is an agonist of the transient receptor potential cation channel subfamily V member 1 (TrpV1).	2.13	1	0	carboxylic ester; diterpenoid; enone; monomethoxybenzene; organic heteropentacyclic compound; ortho ester; phenols; tertiary alpha-hydroxy ketone	analgesic; neurotoxin; plant metabolite; TRPV1 agonist
salubrinal salubrinal: prevents dephosphorylation of eIF2alpha; structure in first source. salubrinal : A member of the class of quinolines that is a mixed aminal resulting from the formal condensation oftrichloroacetaldehyde with the amide nitrogen of trans-cinnamamide and the primary amino group of 1-quinolin-8-ylthiourea. It is a selective inhibitor of cellular complexes that dephosphorylate eukaryotic translation initiation factor 2 subunit alpha (eIF2alpha).	2.07	1	0	aminal; organochlorine compound; quinolines; secondary carboxamide; thioureas
palonosetron Palonosetron: Isoquinoline and quinuclidine derivative that acts as a 5-HT3 RECEPTOR antagonist. It is used in the prevention of nausea and vomiting induced by cytotoxic chemotherapy, and for the prevention of post-operative nausea and vomiting.. palonosetron : An organic heterotricyclic compound that is an antiemetic used (as its hydrochloride salt) in combination with netupitant (under the trade name Akynzeo) to treat nausea and vomiting in patients undergoing cancer chemotherapy.	2.41	1	0	azabicycloalkane; delta-lactam; organic heterotricyclic compound	antiemetic; serotonergic antagonist
pyracrenic acid pyracrenic acid: a lupane from bark of Pyracantha crenulata; structure given in first source	2.15	1	0	triterpenoid	metabolite
sanshool sanshool: isolated from the stem bark of Zanthoxylum liebmannianum; RN given for (E,E,Z,E)-isomer; structure in first source	2.05	1	0	fatty amide
(8)-shogaol (8)-shogaol: isolated from ginger; structure in first source	4.28	5	0	enone; monomethoxybenzene; phenols
(10)-shogaol (10)-shogaol: isolated from ginger; structure in first source	4.27	5	0	enone; monomethoxybenzene; phenols
corosolic acid [no description available]	2.15	1	0	triterpenoid	metabolite
6-dehydrogingerdione 6-dehydrogingerdione: an antineoplastic agent isolated from Zingiber officinale; structure in first source	2.05	1	0	hydroxycinnamic acid
mcc-950 [no description available]	3.35	1	0
huprine y huprine Y: structure in first source	2.1	1	0
betulin-3-caffeate betulin-3-caffeate: has antineoplastic activity; isolated from Hibiscus syriacus; structure in first source	2.15	1	0
sl0101 SL0101: p90 Ribosomal S6 Kinase; structure in first source	2.02	1	0
(+)-lyoniresinol-3-alpha-O-beta-D-glucopyranoside (+)-lyoniresinol-3-alpha-O-beta-D-glucopyranoside : A lignan that is (+)-lyoniresinol substituted by a beta-D-glucopyranosyl moiety at position 3 via a glycosidic linkage. Isolated from the root barks of Stemmadenia minima and Lycium chinense, it exhibits antimicrobial activities.	2.11	1	0	beta-D-glucoside; dimethoxybenzene; lignan; monosaccharide derivative; polyphenol; primary alcohol; tetralins	antibacterial agent; antifungal agent; metabolite
veratridine Veratridine: A benzoate-cevane found in VERATRUM and Schoenocaulon. It activates SODIUM CHANNELS to stay open longer than normal.	2.03	1	0
calcimycin Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.	2.08	1	0	benzoxazole
2alpha,3beta-dihydroxy-20(29)-lupen-28-oic acid alphitolic acid: from the aerial parts of Gouania longipetala; structure in first source. 2alpha,3beta-dihydroxy-20(29)-lupen-28-oic acid : A pentacyclic triterpenoid that is betulinic acid carrying an additional alpha-hydroxy group at position 2. It has been isolated from Breynia fruticosa.	2.15	1	0	dihydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
(-)-pinoresinol (-)-pinoresinol : An enantiomer of pinoresinol having (-)-1R,3aS,4R,6aS-configuration.	2.13	1	0	pinoresinol	plant metabolite
Mangiferonic acid [no description available]	2.17	1	0	triterpenoid
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.51	2	0
hes1 protein, human HES1 protein, human: RefSeq NM_005524	2.25	1	0
chitosan [no description available]	2.17	1	0
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	2.02	1	0
epi-maslinic acid epi-maslinic acid : A pentacyclic triterpenoid that is 3alpha-hydroxy epimer of maslinic acid. Isolated from Prunella vulgaris and Isodon japonicus, it exhibits anti-inflammatory activity.	2.15	1	0	dihydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory agent; metabolite
piperidines Piperidines: A family of hexahydropyridines.	2.46	2	0
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.48	2	0
piroxicam [no description available]	2.1	1	0	benzothiazine; monocarboxylic acid amide; pyridines	analgesic; antirheumatic drug; cyclooxygenase 1 inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
millepachine millepachine: isolated from Millettia pachycarpa Benth (Leguminosae); structure in first source	3.31	1	0
longikaurin a longikaurin A: from Isodon adenolomus; structure in first source	3.31	1	0	kaurane diterpenoid	metabolite
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	2.57	2	0
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone: an interleukin-1beta converting enzyme (ICE)-like protease inhibitor	2.25	1	0
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	2.17	1	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.07	1	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
2-(4-methoxyphenyl)-1H-quinazolin-4-one [no description available]	3.35	1	0	quinazolines
sparstolonin b sparstolonin B: selectively blocks TLR2- and TLR4-mediated inflammatory signaling; isolated from a Chinese herb, Spaganium stoloniferum; structure in first source	3.21	1	0

Condition	Relationship Strength	Studies
Cancer of Mouth [description not available]	3.05	4
Mouth Neoplasms Tumors or cancer of the MOUTH.	3.05	4
Protein Aggregation, Pathological A biochemical phenomenon in which misfolded proteins aggregate either intra- or extracellularly. Triggered by factors such as MUTATION; POST-TRANSLATIONAL MODIFICATIONS, and environmental stress, it is generally associated with ALZHEIMER DISEASE; PARKINSON DISEASE; HUNTINGTON DISEASE; and TYPE 2 DIABETES MELLITUS.	2.1	1
Benign Neoplasms [description not available]	5.64	7
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	5.64	7
Colorectal Cancer [description not available]	3.22	5
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	3.22	5
Hepatocellular Carcinoma [description not available]	8.46	7
Cancer of Liver [description not available]	3.81	10
Invasiveness, Neoplasm [description not available]	3.33	6
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	3.46	7
Liver Neoplasms Tumors or cancer of the LIVER.	3.81	10
Innate Inflammatory Response [description not available]	4.96	12
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.	4.96	12
Amentia [description not available]	3.48	2
Dementia An acquired organic mental disorder with loss of intellectual abilities of sufficient severity to interfere with social or occupational functioning. The dysfunction is multifaceted and involves memory, behavior, personality, judgment, attention, spatial relations, language, abstract thought, and other executive functions. The intellectual decline is usually progressive, and initially spares the level of consciousness.	8.48	2
Acute Kidney Failure [description not available]	2.66	2
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	5.95	13
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	2.66	2
Carcinoma, Squamous Cell of Head and Neck [description not available]	2.31	1
Squamous Cell Carcinoma of Head and Neck The most common type of head and neck carcinoma that originates from cells on the surface of the NASAL CAVITY; MOUTH; PARANASAL SINUSES, SALIVARY GLANDS, and LARYNX. Mutations in TNFRSF10B, PTEN, and ING1 genes are associated with this cancer.	2.31	1
Diathesis [description not available]	2.31	1
Blood Poisoning [description not available]	2.31	1
Liver Dysfunction [description not available]	2.76	2
Liver Diseases Pathological processes of the LIVER.	2.76	2
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	7.31	1
Delayed Effects, Prenatal Exposure [description not available]	2.82	2
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.9	3
Nerve Pain [description not available]	2.41	1
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.41	1
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	3.21	4
Cirrhosis, Liver [description not available]	2.41	1
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	2.41	1
Osteoarthritis of Knee [description not available]	2.41	1
Osteoarthritis, Knee Noninflammatory degenerative disease of the knee joint consisting of three large categories: conditions that block normal synchronous movement, conditions that produce abnormal pathways of motion, and conditions that cause stress concentration resulting in changes to articular cartilage. (Crenshaw, Campbell's Operative Orthopaedics, 8th ed, p2019)	2.41	1
Asthma, Bronchial [description not available]	2.89	3
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	2.89	3
Colitis Gravis [description not available]	4.23	5
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	2.96	3
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	4.23	5
Adenoma, Basal Cell [description not available]	2.41	1
Cancer of Colon [description not available]	5.47	8
Adenoma A benign epithelial tumor with a glandular organization.	7.41	1
Colonic Neoplasms Tumors or cancer of the COLON.	5.47	8
Cirrhosis [description not available]	2.41	1
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.41	1
Acute Liver Injury, Drug-Induced [description not available]	2.75	3
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.	2.75	3
Cancer of Endometrium [description not available]	2.41	1
Endometrial Neoplasms Tumors or cancer of ENDOMETRIUM, the mucous lining of the UTERUS. These neoplasms can be benign or malignant. Their classification and grading are based on the various cell types and the percent of undifferentiated cells.	2.41	1
Carcinoma, Non-Small Cell Lung [description not available]	4.05	11
Cancer of Lung [description not available]	4.22	14
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	4.05	11
Lung Neoplasms Tumors or cancer of the LUNG.	4.22	14
Adjuvant Arthritis [description not available]	2.51	2
Rheumatoid Arthritis [description not available]	7.6	1
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	2.6	1
Cancer of Ovary [description not available]	2.6	1
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	2.6	1
Cardiac Rupture, Traumatic [description not available]	2.41	1
Injury, Ischemia-Reperfusion [description not available]	2.72	2
Intestinal Diseases Pathological processes in any segment of the INTESTINE from DUODENUM to RECTUM.	2.6	1
Ischemia A hypoperfusion of the BLOOD through an organ or tissue caused by a PATHOLOGIC CONSTRICTION or obstruction of its BLOOD VESSELS, or an absence of BLOOD CIRCULATION.	7.6	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.	2.72	2
Ciliophora Infections Infections with protozoa of the phylum CILIOPHORA.	2.6	1
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	2.6	1
Aortic Stenosis [description not available]	2.6	1
Cardiac Failure [description not available]	2.6	1
Aortic Valve Stenosis A pathological constriction that can occur above (supravalvular stenosis), below (subvalvular stenosis), or at the AORTIC VALVE. It is characterized by restricted outflow from the LEFT VENTRICLE into the AORTA.	2.6	1
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	7.6	1
Adenocarcinoma Of Kidney [description not available]	2.55	2
Cancer of Kidney [description not available]	2.55	2
Metastase [description not available]	2.81	3
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	2.55	2
Kidney Neoplasms Tumors or cancers of the KIDNEY.	2.55	2
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.81	3
Bone Loss, Osteoclastic [description not available]	2.69	2
Pericementitis [description not available]	2.25	1
Periodontitis Inflammation and loss of connective tissues supporting or surrounding the teeth. This may involve any part of the PERIODONTIUM. Periodontitis is currently classified by disease progression (CHRONIC PERIODONTITIS; AGGRESSIVE PERIODONTITIS) instead of age of onset. (From 1999 International Workshop for a Classification of Periodontal Diseases and Conditions, American Academy of Periodontology)	7.25	1
Alloxan Diabetes [description not available]	2.25	1
Asymmetric Diabetic Proximal Motor Neuropathy [description not available]	2.25	1
Allodynia [description not available]	2.25	1
Diabetic Neuropathies Peripheral, autonomic, and cranial nerve disorders that are associated with DIABETES MELLITUS. These conditions usually result from diabetic microvascular injury involving small blood vessels that supply nerves (VASA NERVORUM). Relatively common conditions which may be associated with diabetic neuropathy include third nerve palsy (see OCULOMOTOR NERVE DISEASES); MONONEUROPATHY; mononeuropathy multiplex; diabetic amyotrophy; a painful POLYNEUROPATHY; autonomic neuropathy; and thoracoabdominal neuropathy. (From Adams et al., Principles of Neurology, 6th ed, p1325)	2.25	1
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	2.25	1
Pneumonia Infection of the lung often accompanied by inflammation.	2.25	1
Bronchial Hyperreactivity Tendency of the smooth muscle of the tracheobronchial tree to contract more intensely in response to a given stimulus than it does in the response seen in normal individuals. This condition is present in virtually all symptomatic patients with asthma. The most prominent manifestation of this smooth muscle contraction is a decrease in airway caliber that can be readily measured in the pulmonary function laboratory.	2.25	1
Cognitive Decline [description not available]	2.25	1
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	2.25	1
Breast Cancer [description not available]	3.72	9
Breast Neoplasms Tumors or cancer of the human BREAST.	3.72	9
Atypical Lipomatous Tumor [description not available]	2.25	1
Liposarcoma A malignant tumor derived from primitive or embryonal lipoblastic cells. It may be composed of well-differentiated fat cells or may be dedifferentiated: myxoid (LIPOSARCOMA, MYXOID), round-celled, or pleomorphic, usually in association with a rich network of capillaries. Recurrences are common and dedifferentiated liposarcomas metastasize to the lungs or serosal surfaces. (From Dorland, 27th ed; Stedman, 25th ed)	7.25	1
Cancer of Cervix [description not available]	2.31	1
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	2.31	1
Granulocytic Leukemia, Chronic [description not available]	2.31	1
Leukemia, Myelogenous, Chronic, BCR-ABL Positive Clonal hematopoetic disorder caused by an acquired genetic defect in PLURIPOTENT STEM CELLS. It starts in MYELOID CELLS of the bone marrow, invades the blood and then other organs. The condition progresses from a stable, more indolent, chronic phase (LEUKEMIA, MYELOID, CHRONIC PHASE) lasting up to 7 years, to an advanced phase composed of an accelerated phase (LEUKEMIA, MYELOID, ACCELERATED PHASE) and BLAST CRISIS.	2.31	1
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	3.23	1
Adenocarcinoma, Basal Cell [description not available]	2.77	3
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.77	3
Emesis [description not available]	4.82	4
Vomiting The forcible expulsion of the contents of the STOMACH through the MOUTH.	4.82	4
Diabetes Mellitus, Adult-Onset [description not available]	2.57	2
Diabetic Glomerulosclerosis [description not available]	2.58	2
Hyperlipemia [description not available]	2.17	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	2.57	2
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	2.58	2
Hyperlipidemias Conditions with excess LIPIDS in the blood.	2.17	1
Carcinoma, Epidermoid [description not available]	2.85	3
Cancer of Head [description not available]	2.17	1
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	2.85	3
Head and Neck Neoplasms Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)	2.17	1
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	2.55	2
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.17	1
Gout Metabolic disorder characterized by recurrent acute arthritis, hyperuricemia and deposition of sodium urate in and around the joints, sometimes with formation of URIC ACID calculi.	7.17	1
Acute Brain Injuries [description not available]	2.21	1
Brain Hemorrhage, Cerebral [description not available]	2.21	1
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.	2.21	1
Cerebral Hemorrhage Bleeding into one or both CEREBRAL HEMISPHERES including the BASAL GANGLIA and the CEREBRAL CORTEX. It is often associated with HYPERTENSION and CRANIOCEREBRAL TRAUMA.	2.21	1
Cardiomyopathies, Primary [description not available]	2.17	1
Cardiomyopathies A group of diseases in which the dominant feature is the involvement of the CARDIAC MUSCLE itself. Cardiomyopathies are classified according to their predominant pathophysiological features (DILATED CARDIOMYOPATHY; HYPERTROPHIC CARDIOMYOPATHY; RESTRICTIVE CARDIOMYOPATHY) or their etiological/pathological factors (CARDIOMYOPATHY, ALCOHOLIC; ENDOCARDIAL FIBROELASTOSIS).	2.17	1
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.58	2
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	7.58	2
Diabetic Cardiomyopathies Diabetes complications in which VENTRICULAR REMODELING in the absence of CORONARY ATHEROSCLEROSIS and hypertension results in cardiac dysfunctions, typically LEFT VENTRICULAR DYSFUNCTION. The changes also result in myocardial hypertrophy, myocardial necrosis and fibrosis, and collagen deposition due to impaired glucose tolerance.	2.21	1
Hyperuricemia Excessive URIC ACID or urate in blood as defined by its solubility in plasma at 37 degrees C; greater than 0.42mmol per liter (7.0mg/dL) in men or 0.36mmol per liter (6.0mg/dL) in women. This condition is caused by overproduction of uric acid or impaired renal clearance. Hyperuricemia can be acquired, drug-induced or genetically determined (LESCH-NYHAN SYNDROME). It is associated with HYPERTENSION and GOUT.	2.21	1
Cancer of Prostate [description not available]	3.41	2
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	3.41	2
Autosomal Dominant Juvenile Parkinson Disease [description not available]	2.08	1
Parkinsonian Disorders A group of disorders which feature impaired motor control characterized by bradykinesia, MUSCLE RIGIDITY; TREMOR; and postural instability. Parkinsonian diseases are generally divided into primary parkinsonism (see PARKINSON DISEASE), secondary parkinsonism (see PARKINSON DISEASE, SECONDARY) and inherited forms. These conditions are associated with dysfunction of dopaminergic or closely related motor integration neuronal pathways in the BASAL GANGLIA.	2.08	1
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	2.48	2
Arthritis, Degenerative [description not available]	2.1	1
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	2.1	1
Leucocythaemia [description not available]	2.47	2
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	2.47	2
Adenoma, beta-Cell [description not available]	2.1	1
Cancer of Pancreas [description not available]	2.5	2
Insulinoma A benign tumor of the PANCREATIC BETA CELLS. Insulinoma secretes excess INSULIN resulting in HYPOGLYCEMIA.	7.1	1
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	2.5	2
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	2.1	1
Brain Inflammation [description not available]	2.49	2
Encephalitis Inflammation of the BRAIN due to infection, autoimmune processes, toxins, and other conditions. Viral infections (see ENCEPHALITIS, VIRAL) are a relatively frequent cause of this condition.	2.49	2
B16 Melanoma [description not available]	2.49	2
Atherogenesis [description not available]	2.49	2
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	2.49	2
Anasarca [description not available]	3.66	3
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	3.66	3
Carcinoma, Small Cell Lung [description not available]	2.1	1
Small Cell Lung Carcinoma A form of highly malignant lung cancer that is composed of small ovoid cells (SMALL CELL CARCINOMA).	2.1	1
Nausea An unpleasant sensation in the stomach usually accompanied by the urge to vomit. Common causes are early pregnancy, sea and motion sickness, emotional stress, intense pain, food poisoning, and various enteroviruses.	4.33	2
Acute Confusional Senile Dementia [description not available]	2.48	2
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)	2.48	2
Bowel Diseases, Inflammatory [description not available]	3.04	1
Inflammatory Bowel Diseases Chronic, non-specific inflammation of the GASTROINTESTINAL TRACT. Etiology may be genetic or environmental. This term includes CROHN DISEASE and ULCERATIVE COLITIS.	3.04	1
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.13	1
Infarction, Middle Cerebral Artery NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.	2.13	1
Dehydration The condition that results from excessive loss of water from a living organism.	7.15	1
Allergic Contact Dermatitis [description not available]	2.13	1
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	2.13	1
Ache [description not available]	2.15	1
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	7.15	1
Mucositis An INFLAMMATION of the MUCOSA with burning or tingling sensation. It is characterized by atrophy of the squamous EPITHELIUM, vascular damage, inflammatory infiltration, and ulceration. It usually occurs at the mucous lining of the MOUTH, the GASTROINTESTINAL TRACT or the airway due to chemical irritations, CHEMOTHERAPY, or radiation therapy (RADIOTHERAPY).	7.15	1
Papilloma, Squamous Cell [description not available]	2.05	1
Cancer of Skin [description not available]	2.05	1
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	2.05	1
Skin Neoplasms Tumors or cancer of the SKIN.	2.05	1
Anisakiasis Infection with roundworms of the genus ANISAKIS. Human infection results from the consumption of fish harboring roundworm larvae. The worms may cause acute NAUSEA; VOMITING; or penetrate into the wall of the DIGESTIVE TRACT where they give rise to EOSINOPHILIC GRANULOMA in the STOMACH; INTESTINES; or the OMENTUM.	2.05	1
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	2.91	4
Airway Remodeling The structural changes in the number, mass, size and/or composition of the airway tissues.	2.06	1
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	2.07	1
Cerebral Ischemia [description not available]	2.07	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.	2.07	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.07	1
Active Hyperemia [description not available]	2.01	1
Hyperemia The presence of an increased amount of blood in a body part or an organ leading to congestion or engorgement of blood vessels. Hyperemia can be due to increase of blood flow into the area (active or arterial), or due to obstruction of outflow of blood from the area (passive or venous).	2.01	1
Anesthesia A state characterized by loss of feeling or sensation. This depression of nerve function is usually the result of pharmacologic action and is induced to allow performance of surgery or other painful procedures.	2.39	2
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.03	1
Injuries, Spinal Cord [description not available]	2.03	1
Spinal Cord Injuries Penetrating and non-penetrating injuries to the spinal cord resulting from traumatic external forces (e.g., WOUNDS, GUNSHOT; WHIPLASH INJURIES; etc.).	2.03	1
Cancer of Stomach [description not available]	2.03	1
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.03	1
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	7.01	1
Hypothermia, Accidental [description not available]	1.97	1
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.	1.97	1
Hypothermia Lower than normal body temperature, especially in warm-blooded animals.	1.97	1
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	1.96	1

shogaol

Description

Cross-References

Synonyms (55)

Research Excerpts

Overview

Effects

Actions

Treatment

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Drug Classes (3)

Protein Targets (7)

Inhibition Measurements

Activation Measurements

Biological Processes (109)

Molecular Functions (54)

Ceullar Components (27)

Bioassays (141)

Research

Studies (294)

Market Indicators

Research Demand Index: 47.31

Study Types

shogaol

Description

Related Flora

Cross-References

Synonyms (55)

Research Excerpts

Overview

Effects

Actions

Treatment

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Drug Classes (3)

Protein Targets (7)

Inhibition Measurements

Activation Measurements

Biological Processes (109)

Molecular Functions (54)

Ceullar Components (27)

Bioassays (141)

Research

Studies (294)

Market Indicators

Research Demand Index: 47.31

Study Types

Related Drugs (248)

Related Conditions (184)