2-hydroxychavicol profile

2-Hydroxychavicol, also known as chavicol, is a naturally occurring phenolic compound found in various plants, particularly in the essential oil of black pepper (Piper nigrum). It is a colorless to pale yellow liquid with a characteristic spicy aroma. 2-Hydroxychavicol exhibits a range of biological activities, including antioxidant, antimicrobial, anti-inflammatory, and anticancer properties. Its antioxidant activity is attributed to its ability to scavenge free radicals, while its antimicrobial activity is related to its ability to inhibit the growth of bacteria and fungi. Research suggests that 2-hydroxychavicol may also possess anti-inflammatory effects by inhibiting the production of pro-inflammatory cytokines. Additionally, studies have explored its potential anticancer effects, demonstrating its ability to induce apoptosis and inhibit cell proliferation in certain cancer cell lines. 2-Hydroxychavicol is widely studied for its potential therapeutic applications due to its diverse biological activities. Its presence in black pepper and other plants makes it a valuable natural compound with potential health benefits.'

2-hydroxychavicol: antimutagen from betel leaf; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	70775
CHEMBL ID	111134
SCHEMBL ID	43300
MeSH ID	M0145959

Synonym
4-allylcatechol
4-allylpyrocatechol
1,2-benzenediol, 4-(2-propenyl)-
hydroxychavicol
2-hydroxychavicol
ccris 1524
4-(prop-2-en-1-yl)benzene-1,2-diol
STK046904
CHEMBL111134
4-prop-2-enylbenzene-1,2-diol
1126-61-0
fg58c4j9br ,
unii-fg58c4j9br
AKOS005384863
4-allylbenzene-1,2-diol
BBL029399
SCHEMBL43300
W-200844
CS-7492
4-(2-propenyl)-1,2-benzenediol
1,2-dihydroxy-4-allylbenzene
hydroxy chavicol
4-allylbenzene-1,2-d
hydroxychavicol; 4-allylpyrocatechol
desmethylisoeugenol
DTXSID20150112
4-allylpyrocatechol, analytical standard
AS-58835
3,4-dihydroxy-allylbenzene
HY-N1887
mfcd01548379
4-allyl-1,2-dihydroxybenzene
4-allyl-1,2-benzenediol
4-allylcatechol; 2-hydroxychavicol pound>>hydroxychavicol
BCP29736
A894552
bdbm50267733
hydroxychavicolhydroxychavicol
hydroxychavicol, 2-
p-allylcatechol
SY053072

Excerpt	Reference	Relevance
" HC alone was slightly toxic to HepG2 cells."	( Enhanced hydroxychavicol-induced cytotoxic effects in glutathione-depleted HepG2 cells. Chen, CL; Chi, CW; Liu, TY, 2000)	0.31
" This study investigated whether HC modulates cigarette carcinogen benzo[a]pyrene (B[a]P)-mediated toxic effects."	( Hydroxychavicol modulates benzo[a]pyrene-induced genotoxicity through induction of dihydrodiol dehydrogenase. Chang, KW; Chi, CW; Liu, TY; Tang, DW, 2004)	0.32
" HC at a weakly toxic level (0."	( Biotransformation and cytotoxic effects of hydroxychavicol, an intermediate of safrole metabolism, in isolated rat hepatocytes. Ishii, H; Nakagawa, Y; Nakajima, K; Ogata, A; Suzuki, T, 2009)	0.35

Excerpt	Reference	Relevance
" Derivatives of imidazole, 1,3-thiazole and pyrimidine proved to be more potent than febuxostat while also displaying/possessing favorable predicted physico-chemical, pharmacokinetic and toxicological properties."	( Xanthine oxidase inhibitors beyond allopurinol and febuxostat; an overview and selection of potential leads based on in silico calculated physico-chemical properties, predicted pharmacokinetics and toxicity. Anderluh, M; Jakopin, Ž; Kocić, G; Petronijević, Ž; Šmelcerović, A; Šmelcerović, Ž; Tomašič, T; Tomović, K, 2017)	0.46

Excerpt	Relevance	Reference
" HC was well-tolerated at this dosing level without any observable toxicity."	( Hydroxychavicol, a betel leaf component, inhibits prostate cancer through ROS-driven DNA damage and apoptosis. Aneja, R; Brahmbhatt, M; Cheng, A; Gundala, SR; Mukkavilli, R; Pannu, V; Paranjpe, R; Reid, MD; Yang, C, 2014)	0.4

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Xanthine dehydrogenase/oxidase	Homo sapiens (human)	IC50 (µMol)	16.7000	0.0013	2.8138	9.8200	AID1485271
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
allantoin metabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
negative regulation of protein phosphorylation	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
negative regulation of endothelial cell proliferation	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
guanine catabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
inosine catabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
deoxyinosine catabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
adenosine catabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
deoxyadenosine catabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
deoxyguanosine catabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
AMP catabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
IMP catabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
lactation	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
hypoxanthine catabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
xanthine catabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
negative regulation of gene expression	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
iron-sulfur cluster assembly	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
amide catabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
negative regulation of endothelial cell differentiation	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
GMP catabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
dGMP catabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
dAMP catabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
negative regulation of phosphatidylinositol 3-kinase/protein kinase B signal transduction	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
positive regulation of p38MAPK cascade	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
negative regulation of vascular endothelial growth factor signaling pathway	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
positive regulation of reactive oxygen species metabolic process	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
negative regulation of vasculogenesis	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
xanthine dehydrogenase activity	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
xanthine oxidase activity	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
iron ion binding	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
protein binding	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
protein homodimerization activity	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
molybdopterin cofactor binding	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
flavin adenine dinucleotide binding	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
2 iron, 2 sulfur cluster binding	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
hypoxanthine dehydrogenase activity	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
hypoxanthine oxidase activity	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
FAD binding	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
cytosol	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
extracellular space	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
peroxisome	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
cytosol	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
sarcoplasmic reticulum	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
extracellular space	Xanthine dehydrogenase/oxidase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (111)

Assay ID	Title	Year	Journal	Article
AID1196414	Growth inhibition of human MCF7 cells at 30 uM after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543623	Cytotoxicity against human neutrophils at 2.5 to 10 ug/ml after 3 hrs by MTT assay	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196422	Growth inhibition of human MCF7 cells after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1196430	Cell cycle arrest in human HL60 cells assessed as apoptotic cells at 10 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 3%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543619	Antioxidant activity in rat liver microsomes assessed as reduction in lipid peroxidation at 10 to 100 ug/ml by thiobarbituric acid assay	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196410	Growth inhibition of human HL60 cells at 30 uM after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1196428	Cell cycle arrest in human HL60 cells assessed as accumulation at S phase at 5 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 63%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID323196	Cytotoxicity against mouse L929 cells assessed as survival at 10 uM after 20 hrs by MTT method relative to control	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages.
AID543589	Antimicrobial activity against Haemophilus actinomycetemcomitans ATCC 29522 by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID543617	Antimicrobial activity against Streptococcus mutans ATCC 25175 assessed as increase in membrane permeability at 1000 ug/ml after 30 mins by propidium iodide staining-based flow cytometry	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196434	Cell cycle arrest in human HL60 cells assessed as apoptotic cells at 15 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 3%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1485272	Potency index, ratio of allopurinol IC50 to compound IC50 for xanthine oxidase (unknown origin)	2017	European journal of medicinal chemistry, Jul-28, Volume: 135	Xanthine oxidase inhibitors beyond allopurinol and febuxostat; an overview and selection of potential leads based on in silico calculated physico-chemical properties, predicted pharmacokinetics and toxicity.
AID543598	Bactericidal activity against Haemophilus actinomycetemcomitans ATCC 29522 after 24 hrs by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196431	Cell cycle arrest in human HL60 cells assessed as accumulation at G1 phase at 10 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 36%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543592	Antimicrobial activity against Porphyromonas gingivalis ATCC 33277 by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196425	Growth inhibition of human HL60 cells after 24 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543625	Toxicity in healthy human assessed as occurrence of after taste	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID323208	Prevention of 10 mins photoirradiation-induced damage in mouse L929 cells assessed as survival at 5 uM by MTT assay	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages.
AID1683067	Anti-inflammatory activity in murine RAW264.7 cells assessed as inhibition of LPS-induced NO production	2021	Bioorganic & medicinal chemistry letters, 01-01, Volume: 31	A new sesquineolignan and four new neolignans isolated from the leaves of Piper betle, a traditional medicinal plant in Myanmar.
AID543605	Antimicrobial activity against Streptococcus mutans ATCC 25175 after 12 hrs by time kill analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196441	Cell cycle arrest in human HL60 cells assessed as accumulation at G2 phase at 20 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 36%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1196439	Cell cycle arrest in human HL60 cells assessed as accumulation at G1 phase at 20 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 36%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID323209	Prevention of 15 mins photoirradiation-induced damage in mouse L929 cells assessed as survival at 5 uM by MTT assay	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages.
AID1485271	Inhibition of xanthine oxidase (unknown origin) assessed as reduction in uric acid formation using xanthine as substrate after 4 mins by UV-Vis spectrophotometric assay	2017	European journal of medicinal chemistry, Jul-28, Volume: 135	Xanthine oxidase inhibitors beyond allopurinol and febuxostat; an overview and selection of potential leads based on in silico calculated physico-chemical properties, predicted pharmacokinetics and toxicity.
AID1196420	Growth inhibition of human HL60 cells after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1187910	Metal chelating activity of the compound assessed as Cu2+ chelating activity at 10 uM by fluorescence assay relative to control	2014	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17	A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity.
AID1196436	Cell cycle arrest in human HL60 cells assessed as accumulation at S phase at 15 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 63%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1196424	Growth inhibition of human SK-N-SH cells after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1196415	Growth inhibition of human MCF7 cells at 50 uM after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543593	Bactericidal activity against Streptococcus mutans ATCC 25175 after 24 hrs by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196413	Growth inhibition of human MIAPaCa2 cells at 50 uM after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543621	Antiinflammatory activity against human neutrophils assessed as inhibition of LPS-stimulated TNFalpha production at 2.5 ug/ml after 3 hrs by FACS analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1075969	Cytotoxicity against human PC3 cells assessed as growth inhibition after 48 hrs by MTT assay	2014	European journal of medicinal chemistry, Mar-21, Volume: 75	Synthesis and evaluation of antiproliferative activity of a novel series of hydroxychavicol analogs.
AID543612	Antimicrobial activity against Actinomyces viscosus ATCC 15987 assessed as post antibiotic effect at 2 times MIC	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID543610	Antimicrobial activity against Streptococcus mutans ATCC 25175 assessed as post antibiotic effect at 2 times MIC	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID543602	Antimicrobial activity against Streptococcus mutans ATCC 25175 assessed as log reduction in bacterial growth at 250 ug/ml measured at 10 hrs by time kill analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID543615	Antimicrobial activity against Streptococcus mutans ATCC 25175 assessed as eradication of preformed biofilm after 24 hrs by crystal violet staining	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID543597	Bactericidal activity against Actinomyces viscosus ATCC 15987 after 24 hrs by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196417	Growth inhibition of human HepG2 cells at 50 uM after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543591	Antimicrobial activity against Fusobacterium nucleatum ATCC 10953 by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1187905	Inhibition of alpha-glucosidase (unknown origin) using 3 mM p-NPG solution at 50 uM relative to control	2014	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17	A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity.
AID1196435	Cell cycle arrest in human HL60 cells assessed as accumulation at G1 phase at 15 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 36%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543618	Antimicrobial activity against Actinomyces viscosus ATCC 15987 assessed as increase in membrane permeability at 1000 ug/ml after 30 mins by propidium iodide staining-based flow cytometry	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196408	Reduction in mitochondrial membrane potential in human HL60 cells at 5 uM after 24 hrs by Rh-123-staining based flow cytometry (Rvb = 7%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543604	Antimicrobial activity against Streptococcus mutans ATCC 25175 assessed as reduction in bacterial growth at 4 times MIC measured at 4 hrs by time kill analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196416	Growth inhibition of human HepG2 cells at 30 uM after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1110759	Nematocidal activity against Caenorhabditis elegans assessed as mortality	2002	Annual review of phytopathology, , Volume: 40	Phytochemical based strategies for nematode control.
AID323188	Protection against 30 mins photoirradiation-induced lipid peroxidation damage in rat liver mitochondria assessed as prevention of TBARS formation at 180 uM	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages.
AID543614	Antimicrobial activity against Actinomyces viscosus ATCC 15987 assessed as inhibition of biofilm formation after 24 hrs by crystal violet staining	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID543587	Antimicrobial activity against Streptococcus sanguis ATCC 10556 by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID543609	Antimicrobial activity against Streptococcus mutans ATCC 25175 assessed as post antibiotic effect at 250 ug/ml	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID543613	Antimicrobial activity against Streptococcus mutans ATCC 25175 assessed as inhibition of biofilm formation after 24 hrs by crystal violet staining	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196411	Growth inhibition of human HL60 cells at 50 uM after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1196427	Cell cycle arrest in human HL60 cells assessed as accumulation at G1 phase at 5 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 36%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543406	Antimicrobial activity against Streptococcus mutans ATCC 25175 by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196419	Growth inhibition of human SK-N-SH cells at 50 uM after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID323200	Prevention of 15 mins photoirradiation-induced damage in mouse L929 cells assessed as survival at 9 uM by MTT assay	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages.
AID543595	Bactericidal activity against Enterococcus faecalis ATCC 29212 after 24 hrs by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196442	Reduction in mitochondrial membrane potential in human HL60 cells at 10 uM after 24 hrs by Rh-123-staining based flow cytometry (Rvb = 7%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543590	Antimicrobial activity against Prevotella intermedia ATCC 25611 by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID323204	Prevention of 5 mins photoirradiation-induced damage in mouse L929 cells assessed as survival at 10 uM by MTT assay	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages.
AID323206	Prevention of 15 mins photoirradiation-induced damage in mouse L929 cells assessed as survival at 10 uM by MTT assay	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages.
AID543608	Antimicrobial activity against Streptococcus mutans ATCC 25175 at 125 to 500 ug/ml by time kill analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID323186	Protection against 30 mins photoirradiation-induced lipid peroxidation damage in rat liver mitochondria assessed as prevention of TBARS formation at 30 uM	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages.
AID543601	Bactericidal activity against Porphyromonas gingivalis ATCC 33277 after 24 hrs by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196412	Growth inhibition of human MIAPaCa2 cells at 30 uM after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1187909	Antioxidant activity assessed as copper(I)ion reduction power at 10 uM after 1 hr by cupric ion reducing antioxidant capacity assay	2014	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17	A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity.
AID543607	Antimicrobial activity against adherent cells of Streptococcus mutans ATCC 25175 assessed as inhibition of water-insoluble glucan synthesis at 1000 ug/ml in presence of sucrose	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID248765	Inhibitory concentration of compound on nitric oxide (NO) production in lipopolysaccharide activated mouse peritoneal macrophages	2005	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 15, Issue:7	Structure-activity relationships of 1'S-1'-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages.
AID323205	Prevention of 10 mins photoirradiation-induced damage in mouse L929 cells assessed as survival at 10 uM by MTT assay	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages.
AID1196433	Cell cycle arrest in human HL60 cells assessed as accumulation at G2 phase at 10 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 1%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543594	Bactericidal activity against Enterococcus faecium ATCC 8042 after 24 hrs by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1187908	Antioxidant activity assessed as copper(I)ion reduction power at 1 uM after 1 hr by cupric ion reducing antioxidant capacity assay	2014	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17	A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity.
AID1196429	Cell cycle arrest in human HL60 cells assessed as accumulation at G2 phase at 5 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 1%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1196421	Growth inhibition of human MIAPaCa2 cells after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1196444	Reduction in mitochondrial membrane potential in human HL60 cells at 20 uM after 24 hrs by Rh-123-staining based flow cytometry (Rvb = 7%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543606	Antimicrobial activity against adherent cells of Streptococcus mutans ATCC 25175 at 1000 ug/ml	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID543407	Antimicrobial activity against Enterococcus faecium ATCC 8042 by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID543596	Bactericidal activity against Streptococcus sanguis ATCC 10556 after 24 hrs by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID166551	Percentage inhibition against release of beta-hexosaminidase from RBL-2H3 cells at 100 uM from control	2003	Bioorganic & medicinal chemistry letters, Oct-06, Volume: 13, Issue:19	Antiallergic principles from Alpinia galanga: structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF-alpha and IL-4 in RBL-2H3 cells.
AID1196446	Induction of apoptosis in human HL60 cells assessed as effect on morphology at 5 to 20 uM after 24 hrs by phase-contrast microscopy	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1196423	Growth inhibition of human HepG2 cells after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID166539	Inhibitory activity against release of beta-hexosaminidase from RBL-2H3 cells	2003	Bioorganic & medicinal chemistry letters, Oct-06, Volume: 13, Issue:19	Antiallergic principles from Alpinia galanga: structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF-alpha and IL-4 in RBL-2H3 cells.
AID1196438	Cell cycle arrest in human HL60 cells assessed as apoptotic cells at 20 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 3%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543616	Antimicrobial activity against Actinomyces viscosus ATCC 15987 assessed as eradication of preformed biofilm after 24 hrs by crystal violet staining	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID543603	Antimicrobial activity against Streptococcus mutans ATCC 25175 assessed as reduction in bacterial growth at 2 times MIC measured at 8 hrs by time kill analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID323189	Protection against 30 mins photoirradiation-induced damage in rat liver mitochondria assessed as reduction of lipid hydroperoxide formation at 180 uM	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages.
AID543622	Antiinflammatory activity against human neutrophils assessed as inhibition of LPS-stimulated TNFalpha production at 10 ug/ml after 3 hrs by FACS analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1075968	Cytotoxicity against human HeLa cells assessed as growth inhibition after 48 hrs by MTT assay	2014	European journal of medicinal chemistry, Mar-21, Volume: 75	Synthesis and evaluation of antiproliferative activity of a novel series of hydroxychavicol analogs.
AID543586	Antimicrobial activity against Enterococcus faecalis ATCC 29212 by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1196443	Reduction in mitochondrial membrane potential in human HL60 cells at 15 uM after 24 hrs by Rh-123-staining based flow cytometry (Rvb = 7%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1196426	Cell cycle arrest in human HL60 cells assessed as apoptotic cells at 5 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 3%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543599	Bactericidal activity against Prevotella intermedia ATCC 25611 after 24 hrs by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID323195	Cytotoxicity against mouse L929 cells assessed as survival at 5 uM after 20 hrs by MTT method relative to control	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages.
AID323187	Protection against 30 mins photoirradiation-induced lipid peroxidation damage in rat liver mitochondria assessed as prevention of TBARS formation at 60 uM	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages.
AID543611	Antimicrobial activity against Actinomyces viscosus ATCC 15987 assessed as post antibiotic effect at 250 ug/ml	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1187907	Antioxidant activity assessed as trolox equivalent of AAPH radical scavenging activity at 10 uM after 2 mins by ORAC-RCoo assay	2014	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17	A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity.
AID1196445	Induction of apoptosis in human HL60 cells assessed as apoptotic bodies formation at 5 to 20 uM after 24 hrs by Hoechst 33342-staining based fluorescence microscopy	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID515754	Cytotoxicity against human MCF7 cells at 100 uM after 72 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Oct-01, Volume: 18, Issue:19	Comparative nuclease and anti-cancer properties of the naturally occurring malabaricones.
AID1196432	Cell cycle arrest in human HL60 cells assessed as accumulation at S phase at 10 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 63%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID1196437	Cell cycle arrest in human HL60 cells assessed as accumulation at G2 phase at 15 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 63%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID543588	Antimicrobial activity against Actinomyces viscosus ATCC 15987 by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID334211	Cytotoxicity against human NUGC cells at 50 uM	2003	Journal of natural products, Feb, Volume: 66, Issue:2	New flavans, spirostanol sapogenins, and a pregnane genin from Tupistra chinensis and their cytotoxicity.
AID1196418	Growth inhibition of human SK-N-SH cells at 30 uM after 72 hrs by MTT assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
AID323207	Prevention of 5 mins photoirradiation-induced damage in mouse L929 cells assessed as survival at 5 uM by MTT assay	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages.
AID543620	Antiinflammatory activity against human neutrophils assessed as inhibition of LPS-stimulated TNFalpha production at 5 ug/ml after 3 hrs by FACS analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID543626	Toxicity in healthy human assessed as occurrence of tingling sensation	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID543600	Bactericidal activity against Fusobacterium nucleatum ATCC 10953 after 24 hrs by turbidimetric analysis	2009	Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1	Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
AID1187906	Antioxidant activity assessed as trolox equivalent of AAPH radical scavenging activity at 1 uM after 2 mins by ORAC-RCoo assay	2014	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17	A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity.
AID323197	Cytotoxicity against mouse L929 cells assessed as survival at 20 uM after 20 hrs by MTT method relative to control	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages.
AID1196440	Cell cycle arrest in human HL60 cells assessed as accumulation at S phase at 20 uM after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 36%)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	3 (6.00)	18.7374
1990's	2 (4.00)	18.2507
2000's	14 (28.00)	29.6817
2010's	26 (52.00)	24.3611
2020's	5 (10.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	2 (4.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	48 (96.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	2.02	1	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
catechol [no description available]	3.11	1	catechols	allelochemical; genotoxin; plant 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.	2.02	1	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
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.	2.52	2	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
melatonin [no description available]	2.21	1	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	2.51	2	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.08	1	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
arecoline Arecoline: An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands.. arecoline : A tetrahydropyridine that is 1,2,5,6-tetrahydropyridine with a methyl group at position 1, and a methoxycarbonyl group at position 3. An alkaloid found in the areca nut, it acts as an agonist of muscarinic acetylcholine.	2.21	1	enoate ester; methyl ester; pyridine alkaloid; tetrahydropyridine	metabolite; muscarinic agonist
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	2.02	1	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
bis(2-guanidinoethyl)disulfide bis(2-guanidinoethyl)disulfide: bifunctional cation; RN given refers to parent cpd; structure	2.02	1
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	1.98	1	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
rolipram [no description available]	2.05	1	pyrrolidin-2-ones	antidepressant; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
safrole Safrole: A member of the BENZODIOXOLES that is a constituent of several VOLATILE OILS, notably SASSAFRAS oil. It is a precursor in the synthesis of the insecticide PIPERONYL BUTOXIDE and the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA).. safrole : A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sassafras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.	2.41	2	benzodioxoles	flavouring agent; insecticide; metabolite; plant metabolite
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	1.96	1	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	2.31	1	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	2.04	1	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
mannitol [no description available]	2.04	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
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.	2.05	1	monoterpenoid; phenols	volatile oil component
methyleugenol methyleugenol: structure	2.42	2	phenylpropanoid
acetyleugenol acetyleugenol: from cloves; inhibits arachidonate-, adrenaline-, & collagen-induced platelet aggregation	2.01	1	benzoate ester; phenols
oleanolic acid [no description available]	2.13	1	hydroxy monocarboxylic acid; pentacyclic triterpenoid	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.	2	1	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
methylnitrosourea Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.	1.97	1	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
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.	2.54	2	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
buthionine sulfoximine Buthionine Sulfoximine: A synthetic amino acid that depletes glutathione by irreversibly inhibiting gamma-glutamylcysteine synthetase. Inhibition of this enzyme is a critical step in glutathione biosynthesis. It has been shown to inhibit the proliferative response in human T-lymphocytes and inhibit macrophage activation. (J Biol Chem 1995;270(33):1945-7). 2-amino-4-(S-butylsulfonimidoyl)butanoic acid : A non-proteinogenic alpha-amino acid that is homocysteine in which the thiol group carries an oxo, imino and butyl groups.. S-butyl-DL-homocysteine (S,R)-sulfoximine : A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.	2.44	2	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
tomatine alpha-tomatine: in tomato fruits and vegetative plant tissues; structure in first source	3.11	1	alkaloid antibiotic; glycoalkaloid; glycoside; steroid alkaloid; tetrasaccharide derivative	antifungal agent; immunological adjuvant; phytotoxin
sodium azide Sodium Azide: A cytochrome oxidase inhibitor which is a nitridizing agent and an inhibitor of terminal oxidation. (From Merck Index, 12th ed). sodium azide : The sodium salt of hydrogen azide (hydrazoic acid).	2.04	1	inorganic sodium salt	antibacterial agent; explosive; mitochondrial respiratory-chain inhibitor; mutagen
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	2.11	1	pseudohalide anion	mitochondrial respiratory-chain inhibitor
1'-hydroxyestragole 1'-hydroxyestragole: structure	2.02	1
4-(n-methyl-n-nitrosamino)-1-(3-pyridyl)-1-butanone 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone: structure; from tobacco smoke	1.97	1	nitrosamine; pyridines
4-vinylphenol 4-vinylphenol: RN given refers to cpd with locants as specified. 4-hydroxystyrene : A member of the class of phenols that is styrene carrying a hydroxy substituent at position 4.	3.11	1	phenols	human urinary metabolite; human xenobiotic metabolite
allicin [no description available]	3.11	1	botanical anti-fungal agent; sulfoxide	antibacterial agent
chavicol 4-allylphenol: an inhibitor of aryl-alcohol oxidase; has free radical scavenging activity. chavicol : A phenylpropanoid that is phenol substituted by a prop-2-enyl group at position 4.	3.81	3	phenols; phenylpropanoid
beta-amyrin beta-amyrin: alpha-amyrin is also available; a 5 ring triterpene derived from oleanane that differs from alpha-amyrin in having the 29-carbon at the 20 position; RN given refers to (3 beta)-isomer. beta-amyrin : A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants.	2.13	1	pentacyclic triterpenoid; secondary alcohol	Aspergillus metabolite; plant metabolite
malabaricone c malabaricone C: from maize (Myristica fragrans); structure given in first source	2.05	1	butanone	metabolite
1'-acetoxychavicol acetate 1'-acetoxychavicol acetate: antifungal component of Alpinia galanga; structure given in first source. 1'-acetoxychavicol acetate : An acetate ester that is chavicol acetate substituted by an acetoxy group at position 1'.	2.42	2	acetate ester; phenylpropanoid	antineoplastic agent; NF-kappaB inhibitor; plant metabolite
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.	2.52	2	methanesulfonate salt	anticoronaviral agent; antineoplastic agent; apoptosis inducer; tyrosine kinase inhibitor
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.	2.31	1	amino acid zwitterion; arginine derivative; guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid
febuxostat Febuxostat: A thiazole derivative and inhibitor of XANTHINE OXIDASE that is used for the treatment of HYPERURICEMIA in patients with chronic GOUT.. febuxostat : A 1,3-thiazolemonocarboxylic acid that is 4-methyl-1,3-thiazole-5-carboxylic acid which is substituted by a 3-cyano-4-(2-methylpropoxy)phenyl group at position 2. It is an orally-active, potent, and selective xanthine oxidase inhibitor used for the treatment of chronic hyperuricaemia in patients with gout.	3.25	1	1,3-thiazolemonocarboxylic acid; aromatic ether; nitrile	EC 1.17.3.2 (xanthine oxidase) inhibitor
quinone methide quinone methide: intermediate in eumelanin biosynthesis; structure given in first source. quinomethane : A methylidenecyclohexadienone, formally derived from a benzoquinone by replacement of one of the quinone oxygens by a methylidene group.	1.98	1	quinomethane
dihydroguaiaretic acid dihydroguaiaretic acid: lignan extracted form Larrea divaricata; inhibitory to beef heart mitochondrial succinoxidase & NADH-oxidase; RN given refers to cpd without isomeric designation	3.11	1
malabaricone b malabaricone B: from maize (Myristica fragrans); structure given in first source	2.05	1
3-n-butyl-4,5-dihydrophthalide 3-N-butyl-4,5-dihydrophthalide: from seeds of Apium graveolens Linn.; RN given refers to (-)-isomer; structure given in first source	3.11	1
benzyl d-glucopyranoside benzyl beta-D-glucopyranoside : A beta-D-glucoside that is beta-D-glucopyranose in which the hydroxy group at position 1R is substituted by a benzyloxy group.	2.1	1	benzenes; beta-D-glucoside	plant metabolite
malabaricone a malabaricone A: from Myristica malabarica (rampatri), has antipromastigote activity; structure in first source	2.05	1
acarbose [no description available]	2.1	1	amino cyclitol; glycoside
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2.42	2	cinnamic acid	plant metabolite
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.	2.03	1	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
y-700 [no description available]	3.25	1
chavibetol chavibetol: isolated from essential oil of Pimenta pseudocaryophyllus leaf; structure in first source	2.76	3	methoxybenzenes; phenols
2-hydroxycinnamic acid trans-2-coumaric acid : The trans-isomer of 2-coumaric acid.. 2-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring.	2.42	2	2-coumaric acid; phenols	antioxidant; metabolite
3-coumaric acid 3-coumaric acid: RN given refers to cpd without isomeric designation in Chemline. trans-3-coumaric acid : A 3-coumaric acid that is phenol substituted with trans-2-propenoic acid at position C-3.. 3-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-3 of the phenyl ring.	2.42	2	3-coumaric acid
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	2.01	1	4-coumaric acid	food component; mouse metabolite; plant metabolite
sinapinic acid sinapinic acid: a matrix for matrix-assisted laser desorption technique for protein MW determination; a constituent of propolis. trans-sinapic acid : A sinapic acid in which the double bond has trans-configuration.	2.42	2	sinapic acid	MALDI matrix material; plant metabolite
p-hydroxycinnamaldehyde p-hydroxycinnamaldehyde: an antibacterial substance from the saw fly, Acantholyda parki S.; structure in first source. 4-hydroxycinnamaldehyde : A cinnamaldehyde that is (E)-cinnamaldehyde substituted at position 4 on the phenyl ring by a hydroxy group.	2.74	3	cinnamaldehydes	apoptosis inducer; EC 1.14.13.39 (nitric oxide synthase) inhibitor; plant metabolite
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.42	2	caffeic acid	geroprotector; mouse metabolite
4-methoxycinnamic acid [no description available]	2.42	2	cinnamic acids
3-(3,4-dimethoxyphenyl)propenoic acid 3-(3,4-dimethoxyphenyl)propenoic acid: structure given in first source; RN given refers to parent cpd. 3,4-dimethoxycinnamic acid : A methoxycinnamic acid that is trans-cinnamic acid substituted by methoxy groups at positions 3' and 4' respectively.	2.42	2	methoxycinnamic acid
coniferyl alcohol coniferyl alcohol: structure. coniferol : A phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring.	2.31	1	guaiacols; phenylpropanoid	animal metabolite; monolignol; mouse metabolite; pheromone; plant metabolite; volatile oil component
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	2.07	1	cinnamate ester; tannin	food component; plant metabolite
quercetin [no description available]	3.25	1	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.	2.01	1	prostaglandins E	human metabolite; mouse metabolite; oxytocic
acacetin 5,7-dihydroxy-4'-methoxyflavone : A monomethoxyflavone that is the 4'-methyl ether derivative of apigenin.	3.25	1	dihydroxyflavone; monomethoxyflavone	anticonvulsant; plant metabolite
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	3.25	1	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	3.56	2	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	3.11	1	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
3-(4-hydroxyphenyl)-1-propane 3-(4-hydroxyphenyl)-1-propane: structure given in first source. trans-p-coumaryl alcohol : 4-Hydroxycinnamyl alcohol with E-configuration of the propenyl double bond. It is one of the main monolignols.. 4-hydroxycinnamyl alcohol : A primary alcohol being cinnamyl alcohol hydroxylated at C-4 of the phenyl ring.	2.42	2	4-hydroxycinnamyl alcohol; phenols; phenylpropanoid	monolignol
coniferaldehyde coniferaldehyde: from aqueous extract of Senra incana. coniferyl aldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.31	1	cinnamaldehydes; guaiacols; phenylpropanoid	antifungal agent; plant metabolite
genistein [no description available]	3.25	1	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
baicalein [no description available]	3.25	1	trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 4.1.1.17 (ornithine decarboxylase) inhibitor; ferroptosis inhibitor; geroprotector; hormone antagonist; plant metabolite; prostaglandin antagonist; radical scavenger
chrysin chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.	3.25	1	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
Pinosylvin methyl ether [no description available]	3.11	1	stilbenoid
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	2.02	1	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
tranilast tranilast: antiallergic drug; potent inhibitor of homologous passive cutaneous anaphylaxis. tranilast : An amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 3,4-dimethoxycinnamoyl group.	2.01	1	amidobenzoic acid; cinnamamides; dimethoxybenzene; secondary carboxamide	anti-allergic agent; anti-asthmatic drug; antineoplastic agent; aryl hydrocarbon receptor agonist; calcium channel blocker; hepatoprotective agent; nephroprotective agent
thromboxane b2 Thromboxane B2: A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).. thromboxane B2 : A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.	2.03	1	thromboxanes B	human metabolite; mouse metabolite
topiroxostat FYX-051: xanthine oxidoreductase inhibitor	3.25	1
methyl-p-coumarate methyl-p-coumarate: structure in first source. 4-coumaric acid methyl ester : A cinnamate ester that is the methyl ester of 4-coumaric acid.	2.31	1	4-coumaric acid methyl ester
plastochromanol 8 plastochromanol 8: has antiproliferative activity against 3T3-L1 cells and anti-adipogenic activity; structure; plastochromanol 3 is gamma-tocotrienol	2.54	2
broussochalcone a broussochalcone A: RN given for (E)-isomer; inhibits neutrophil respiratory burst; structure in first source	3.25	1
tachioside tachioside: from the linseed meal; structure in first source	2.1	1
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.04	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	2.21	1
deoxyguanosine [no description available]	2.4	2	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	3.9	3	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	2.4	2	guanosines	biomarker

Condition	Relationship Strength	Studies
Cancer of Nasopharynx [description not available]	2.01	1
Cancer of Stomach [description not available]	2.01	1
Nasopharyngeal Neoplasms Tumors or cancer of the NASOPHARYNX.	2.01	1
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.01	1
Benign Neoplasms [description not available]	2.1	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.1	1
Benign Neoplasms, Brain [description not available]	2.54	2
Glial Cell Tumors [description not available]	2.54	2
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	2.54	2
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	2.54	2
Age-Related Osteoporosis [description not available]	2.31	1
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	2.31	1
Bacterial Disease [description not available]	2.15	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).	2.15	1
Bacterial Infections Infections by bacteria, general or unspecified.	2.15	1
Granulocytic Leukemia, Chronic [description not available]	2.8	3
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.	2.8	3
Cancer of Pancreas [description not available]	2.21	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).	2.21	1
Cancer of Prostate [description not available]	2.49	2
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.49	2
Candida Infection [description not available]	2.13	1
Dermatomycoses Superficial infections of the skin or its appendages by any of various fungi.	2.13	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.49	2
Dermatophytoses [description not available]	2.13	1
Candidiasis Infection with a fungus of the genus CANDIDA. It is usually a superficial infection of the moist areas of the body and is generally caused by CANDIDA ALBICANS. (Dorland, 27th ed)	2.13	1
Tinea Fungal infection of keratinized tissues such as hair, skin and nails. The main causative fungi include MICROSPORUM; TRICHOPHYTON; and EPIDERMOPHYTON.	2.13	1
Adjuvant Arthritis [description not available]	2.05	1
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	2.05	1
Carcinoma, Epidermoid [description not available]	2.42	2
Cancer of Mouth [description not available]	2.42	2
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)	2.42	2
Mouth Neoplasms Tumors or cancer of the MOUTH.	2.42	2
Abnormalities, Autosome [description not available]	1.99	1
Cancer of Liver [description not available]	2	1
Liver Neoplasms Tumors or cancer of the LIVER.	2	1

2-hydroxychavicol

Description

Cross-References

Synonyms (41)

Research Excerpts

Toxicity

Pharmacokinetics

Dosage Studied

Protein Targets (1)

Inhibition Measurements

Biological Processes (27)

Molecular Functions (11)

Ceullar Components (4)

Bioassays (111)

Research

Studies (50)

Market Indicators

Research Demand Index: 11.24

Study Types

2-hydroxychavicol

Description

Cross-References

Synonyms (41)

Research Excerpts

Toxicity

Pharmacokinetics

Dosage Studied

Protein Targets (1)

Inhibition Measurements

Biological Processes (27)

Molecular Functions (11)

Ceullar Components (4)

Bioassays (111)

Research

Studies (50)

Market Indicators

Research Demand Index: 11.24

Study Types

Related Drugs (85)

Related Conditions (36)