Compounds > 1'-acetoxychavicol acetate
Page last updated: 2024-12-07

1'-acetoxychavicol acetate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

1'-acetoxychavicol acetate, also known as eugenyl acetate, is a natural compound found in essential oils of plants like clove, cinnamon, and nutmeg. It is synthesized through the acetylation of eugenol, a phenolic compound. Eugenyl acetate possesses various biological activities, including antimicrobial, antioxidant, and anti-inflammatory properties. It is studied for its potential applications in food preservation, medicine, and cosmetics. Its antimicrobial properties make it a promising candidate for use as a natural food preservative. Moreover, its antioxidant effects contribute to its potential therapeutic benefits, such as reducing oxidative stress and inflammation. The compound is also used in fragrances and flavorings due to its pleasant aroma. Its potential health benefits and diverse applications continue to drive research into its properties and applications.

1'-acetoxychavicol acetate: antifungal component of Alpinia galanga; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1'-acetoxychavicol acetate : An acetate ester that is chavicol acetate substituted by an acetoxy group at position 1'. [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]

FloraRankFlora DefinitionFamilyFamily Definition
AlpiniagenusA plant genus of the family ZINGIBERACEAE. Members contain galangin, yakuchinone-A, and diarylheptanoids.[MeSH]ZingiberaceaeA 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]

Cross-References

ID SourceID
PubMed CID119104
CHEMBL ID323727
CHEBI ID469
SCHEMBL ID17454871
MeSH IDM0138216

Synonyms (31)

Synonym
1's-1'-acetoxychavicol acetate
[4-[(1s)-1-acetoxyallyl]phenyl] acetate
benzenemethanol, 4-(acetyloxy)-.alpha.-ethenyl-, acetate, (.alpha.s)-
(1s)-1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate
(alphas)-4-(acetyloxy)-alpha-ethenylbenzenemethanol
CHEBI:469 ,
benzenemethanol, 4-(acetyloxy)-alpha-ethenyl-, acetate, (s)-
1'-acetoxychavicol acetate
52946-22-2
(s)-1'-acetoxychavicol acetate
CHEMBL323727
[4-[(1s)-1-acetyloxyprop-2-enyl]phenyl] acetate
sqv3080a20 ,
unii-sqv3080a20
gtpl6298
benzenemethanol, 4-(acetyloxy)-.alpha.-ethenyl-, 1-acetate, (.alpha.s)-
(1's)-1'-acetoxychavicol acetate
galangal acetate, (s)-
galangal acetate, (-)-
1'-acetoxychavicol acetate, (-)-
JAMQIUWGGBSIKZ-ZDUSSCGKSA-N
(s)-4-(1-acetoxyallyl)phenyl acetate
benzenemethanol, 4-(acetyloxy)-.alpha.-ethenyl-, acetate, (s)-
SCHEMBL17454871
1'-acetoxychavicol
Q27070798
acetoxychavicol acetate, d/l-1''-
DTXSID80967420
PD046214
EN300-27114805
Z2737403435

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" The goal of the present study was to determine whether AUR and ACA are effective either alone or in combination with all-trans retinoic acid (ATRA) for suppressing SCC tumor growth."( Effects of ATRA combined with citrus and ginger-derived compounds in human SCC xenografts.
Adegboyega, P; Clifford, JL; Gill, JN; Kleiner-Hancock, HE; Mathis, JM; Prince, M; Remeika, A; Robbins, D; Shi, R; Syed, Z, 2010)		0.36
" However, in combination with ATRA at 5, 10, and 30 ppm, ACA 500 ppm significantly inhibited tumor volume by 56%, 62%, and 98%, respectively."( Effects of ATRA combined with citrus and ginger-derived compounds in human SCC xenografts.
Adegboyega, P; Clifford, JL; Gill, JN; Kleiner-Hancock, HE; Mathis, JM; Prince, M; Remeika, A; Robbins, D; Shi, R; Syed, Z, 2010)		0.36

Dosage Studied

ExcerptRelevanceReference
" They were fed the diets containing 100 or 200 ppm ACA for 5 weeks, starting 1 week before the first dosing of AOM."( A xanthine oxidase inhibitor 1'-acetoxychavicol acetate inhibits azoxymethane-induced colonic aberrant crypt foci in rats.
Hara, A; Kawabata, K; Kawamori, T; Koshimizu, K; Makita, H; Mori, H; Murakami, A; Ohigashi, H; Satoh, K; Tanaka, T, 1997)		0.59
" They were fed diet containing 100 or 500 ppm ACA for 4 weeks, starting one week before the first dosing of AOM (the initiation feeding)."( Chemoprevention of azoxymethane-induced rat colon carcinogenesis by a xanthine oxidase inhibitor, 1'-acetoxychavicol acetate.
Hara, A; Kakumoto, M; Kawabata, K; Koshimizu, K; Makita, H; Matsunaga, K; Mori, H; Murakami, A; Ohigashi, H; Satoh, K; Tanaka, T, 1997)		0.51
"Double and triple combination regimens that target induction of the same death mechanism with reduced dosage of each drug could potentially be clinically beneficial in reducing dose-related toxicities."( Inactivation of nuclear factor κB by MIP-based drug combinations augments cell death of breast cancer cells.
Ahmed, N; Awang, K; In, L; Liew, SK; Nagoor, NH; Subramaniam, M, 2018)		0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
NF-kappaB inhibitorAn inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
acetate esterAny carboxylic ester where the carboxylic acid component is acetic acid.
phenylpropanoidAny organic aromatic compound with a structure based on a phenylpropane skeleton. The class includes naturally occurring phenylpropanoid esters, flavonoids, anthocyanins, coumarins and many small phenolic molecules as well as their semi-synthetic and synthetic analogues. Phenylpropanoids are also precursors of lignin.
[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]

Bioassays (50)

Assay IDTitleYearJournalArticle
AID1194402Inhibition of NF-kappaB in human IM9 cells assessed as inhibition of nuclear translocation at 1 uM after 30 mins by NF-kappaB (p65) transcription factor assay2015Bioorganic & medicinal chemistry, May-01, Volume: 23, Issue:9
Structure-activity relationships of benzhydrol derivatives based on 1'-acetoxychavicol acetate (ACA) and their inhibitory activities on multiple myeloma cell growth via inactivation of the NF-κB pathway.
AID1325094Inhibition of mushroom tyrosinase activity using L-tyrosine as substrate at 100 uM after 30 mins2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID1325114Downregulation of TRP2 expression in theophylline-stimulated mouse B16-4A5 cells assessed as ratio of TRP2 mRNA expression to beta-actin mRNA expression at 10 uM after 72 hrs by qRT-PCR analysis (Rvb = 1 +/- 0.07 No_unit)2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID248765Inhibitory concentration of compound on nitric oxide (NO) production in lipopolysaccharide activated mouse peritoneal macrophages2005Bioorganic & 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.
AID166547Percentage inhibition against antigen-induced TNF-alpha production in RBL-2H3 cells at 100 uM concentration2003Bioorganic & 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.
AID1325087Cytotoxicity against theophylline-stimulated mouse B16-4A5 cells assessed as cell viability at 10 uM after 72 hrs by MTT assay relative to control2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID166545Percentage inhibition against antigen-induced TNF-alpha production in RBL-2H3 cells at 0 uM concentration2003Bioorganic & 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.
AID1325110Downregulation of TRP1 expression in theophylline-stimulated mouse B16-4A5 cells assessed as ratio of TRP1 mRNA expression to beta-actin mRNA expression at 10 uM after 72 hrs by qRT-PCR analysis (Rvb = 1 +/- 0.03 No_unit)2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID473043Inhibition of HIV1 HA-tagged Rev nuclear export expressed in human HeLa cells assessed as cellular localization after 12 hrs by FITC-labelled indirect fluorescence microscopy2010Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7
Halogenated analogs of 1'-acetoxychavicol acetate, Rev-export inhibitor from Alpinia galanga, designed from mechanism of action.
AID109998In vivo inhibitory activity against leakage of dye on ear PCA reaction 30 min after 25 mg/kg oral administration in mice2003Bioorganic & 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.
AID1325106Downregulation of tyrosinase expression in theophylline-stimulated mouse B16-4A5 cells assessed as ratio of tyrosinase mRNA expression to beta-actin mRNA expression at 10 uM after 72 hrs by qRT-PCR analysis (Rvb = 1 +/- 0.09 No_unit)2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID1325092Potency index, ratio of arbutin IC50 to compound IC50 for antimelanogenic activity in mouse B16-4A5 cells2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID353352Inhibition of hemagglutininin-tagged HIV1 Rev protein nuclear export in human HeLa cells assessed as localization at 5 uM by indirect fluorescent antibody technique2009Bioorganic & medicinal chemistry letters, May-01, Volume: 19, Issue:9
New Rev-export inhibitor from Alpinia galanga and structure-activity relationship.
AID1325095Inhibition of mushroom tyrosinase activity using L-DOPA as substrate at 10 uM after 30 mins2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID1194401Inhibition of NF-kappaB in human IM9 cells assessed as inhibition of nuclear translocation at 10 uM after 30 mins by NF-kappaB (p65) transcription factor assay2015Bioorganic & medicinal chemistry, May-01, Volume: 23, Issue:9
Structure-activity relationships of benzhydrol derivatives based on 1'-acetoxychavicol acetate (ACA) and their inhibitory activities on multiple myeloma cell growth via inactivation of the NF-κB pathway.
AID1325108Downregulation of TRP1 expression in theophylline-stimulated mouse B16-4A5 cells assessed as ratio of TRP1 mRNA expression to beta-actin mRNA expression at 3 uM after 72 hrs by qRT-PCR analysis (Rvb = 1 +/- 0.03 No_unit)2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID352014Antiallergic activity against antigen-IgE-mediated degranulation in rat RBL2H3 cells assessed as inhibition of DNP-BSA-induced IL4 release preincubated for 10 mins before DNP-BSA challenge measured after 4 hrs2009Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11
Acetoxybenzhydrols as highly active and stable analogues of 1'S-1'-acetoxychavicol, a potent antiallergic principal from Alpinia galanga.
AID1325078Antimelanogenic activity in theophylline-stimulated mouse B16-4A5 cells assessed as inhibition of melanogenesis at 10 uM after 72 hrs relative to control2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID1325076Antimelanogenic activity in theophylline-stimulated mouse B16-4A5 cells assessed as inhibition of melanogenesis at 1 uM after 72 hrs relative to control2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID1194403Cytotoxicity against human IM9 cells assessed as growth inhibition after 3 days2015Bioorganic & medicinal chemistry, May-01, Volume: 23, Issue:9
Structure-activity relationships of benzhydrol derivatives based on 1'-acetoxychavicol acetate (ACA) and their inhibitory activities on multiple myeloma cell growth via inactivation of the NF-κB pathway.
AID109996In vivo inhibitory activity against leakage of dye on ear PCA reaction 30 min after 12.5 mg/kg oral administration in mice2003Bioorganic & 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.
AID1325093Inhibition of mushroom tyrosinase activity using L-tyrosine as substrate at 10 uM after 30 mins2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID110000In vivo inhibitory activity against leakage of dye on ear PCA reaction 30 min after 50 mg/kg oral administration in mice2003Bioorganic & 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.
AID166537Inhibitory activity against IL-4 production in RBL-2H3 cells was determined2003Bioorganic & 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.
AID1325085Cytotoxicity against theophylline-stimulated mouse B16-4A5 cells assessed as cell viability at 1 uM after 72 hrs by MTT assay relative to control2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID1194399Cytotoxicity against human HL60 cells assessed as growth inhibition after 3 days2015Bioorganic & medicinal chemistry, May-01, Volume: 23, Issue:9
Structure-activity relationships of benzhydrol derivatives based on 1'-acetoxychavicol acetate (ACA) and their inhibitory activities on multiple myeloma cell growth via inactivation of the NF-κB pathway.
AID352013Antiallergic activity against antigen-IgE-mediated degranulation in rat RBL2H3 cells assessed as inhibition of DNP-BSA-induced TNFalpha release preincubated for 10 mins before DNP-BSA challenge measured after 4 hrs2009Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11
Acetoxybenzhydrols as highly active and stable analogues of 1'S-1'-acetoxychavicol, a potent antiallergic principal from Alpinia galanga.
AID166543Percentage inhibition against antigen-induced IL-4 production in RBL-2H3 cells at 3 uM concentration2003Bioorganic & 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.
AID166546Percentage inhibition against antigen-induced TNF-alpha production in RBL-2H3 cells at 10 uM concentration2003Bioorganic & 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.
AID1325096Inhibition of mushroom tyrosinase activity using L-DOPA as substrate at 100 uM after 30 mins2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID166541Percentage inhibition against antigen-induced IL-4 production in RBL-2H3 cells at 10 uM concentration2003Bioorganic & 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.
AID166538Inhibitory activity against TNF-alpha production in RBL-2H3 cells was determined2003Bioorganic & 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.
AID166542Percentage inhibition against antigen-induced IL-4 production in RBL-2H3 cells at 100 uM concentration2003Bioorganic & 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.
AID352012Antiallergic activity against antigen-IgE-mediated degranulation in rat RBL2H3 cells assessed as inhibition of DNP-BSA-induced beta-hexosaminidase release preincubated for 10 mins before DNP-BSA challenge measured after 10 mins2009Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11
Acetoxybenzhydrols as highly active and stable analogues of 1'S-1'-acetoxychavicol, a potent antiallergic principal from Alpinia galanga.
AID352011Chemical stability in DMSO-d6/D2O solution assessed as decomposition after 48 hrs2009Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11
Acetoxybenzhydrols as highly active and stable analogues of 1'S-1'-acetoxychavicol, a potent antiallergic principal from Alpinia galanga.
AID1325079Antimelanogenic activity in theophylline-stimulated mouse B16-4A5 cells assessed as inhibition of melanogenesis after 72 hrs relative to control2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID166540Percentage inhibition against antigen-induced IL-4 production in RBL-2H3 cells at 0 uM concentration2003Bioorganic & 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.
AID110001In vivo inhibitory activity against leakage of dye on ear PCA reaction 30 min after 6.25 mg/kg oral administration in mice2003Bioorganic & 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.
AID166544Percentage inhibition against antigen-induced IL-4 production in RBL-2H3 cells at 30 uM concentration2003Bioorganic & 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.
AID1325086Cytotoxicity against theophylline-stimulated mouse B16-4A5 cells assessed as cell viability at 3 uM after 72 hrs by MTT assay relative to control2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID1325084Cytotoxicity against theophylline-stimulated mouse B16-4A5 cells assessed as cell viability at 0.3 uM after 72 hrs by MTT assay relative to control2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID166539Inhibitory activity against release of beta-hexosaminidase from RBL-2H3 cells2003Bioorganic & 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.
AID166549Percentage inhibition against antigen-induced TNF-alpha production in RBL-2H3 cells at 3 uM concentration2003Bioorganic & 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.
AID1325112Downregulation of TRP2 expression in theophylline-stimulated mouse B16-4A5 cells assessed as ratio of TRP2 mRNA expression to beta-actin mRNA expression at 3 uM after 72 hrs by qRT-PCR analysis (Rvb = 1 +/- 0.07 No_unit)2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID473041Inhibition of HIV1 Rev nuclear export in Saccharomyces pombe expressing GST-NLS-GFP-RevNES fused protein assessed as cellular distribution after 3 hrs by fluorescence microscopy2010Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7
Halogenated analogs of 1'-acetoxychavicol acetate, Rev-export inhibitor from Alpinia galanga, designed from mechanism of action.
AID1325077Antimelanogenic activity in theophylline-stimulated mouse B16-4A5 cells assessed as inhibition of melanogenesis at 3 uM after 72 hrs relative to control2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID1325075Antimelanogenic activity in theophylline-stimulated mouse B16-4A5 cells assessed as inhibition of melanogenesis at 0.3 uM after 72 hrs relative to control2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID1325104Downregulation of tyrosinase expression in theophylline-stimulated mouse B16-4A5 cells assessed as ratio of tyrosinase mRNA expression to beta-actin mRNA expression at 3 uM after 72 hrs by qRT-PCR analysis (Rvb = 1 +/- 0.09 No_unit)2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
AID166550Percentage inhibition against antigen-induced TNF-alpha production in RBL-2H3 cells at 30 uM concentration2003Bioorganic & 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.
AID1346556Human TRPA1 (Transient Receptor Potential channels)2010Bioscience, biotechnology, and biochemistry, , Volume: 74, Issue:8
Galangal pungent component, 1'-acetoxychavicol acetate, activates TRPA1.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (80)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (2.50)18.7374
1990's8 (10.00)18.2507
2000's29 (36.25)29.6817
2010's37 (46.25)24.3611
2020's4 (5.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.41

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index25.41 (24.57)
Research Supply Index4.43 (2.92)
Research Growth Index5.28 (4.65)
Search Engine Demand Index29.12 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.41)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (3.61%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other80 (96.39%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
4-hydroxybenzaldehyde
[no description available]		2.1310hydroxybenzaldehydeEC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor;
mouse metabolite;
plant metabolite
acetone
methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).		2.0210ketone body;
methyl ketone;
propanones;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
human metabolite;
polar aprotic solvent
butyric acid
Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.		2.4920fatty acid 4:0;
straight-chain saturated fatty acid		human urinary metabolite;
Mycoplasma genitalium metabolite
choline
[no description available]		6.9910cholinesallergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
neurotransmitter;
nutrient;
plant metabolite;
Saccharomyces cerevisiae metabolite
3-hydroxybutyric acid
3-Hydroxybutyric Acid: BUTYRIC ACID substituted in the beta or 3 position. It is one of the ketone bodies produced in the liver.. 3-hydroxybutyric acid : A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics.		2.1310(omega-1)-hydroxy fatty acid;
3-hydroxy monocarboxylic acid;
hydroxybutyric acid		human metabolite
nitrates
Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.		2.1110monovalent 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)		2.1110monovalent inorganic anion;
nitrogen oxoanion;
reactive nitrogen species		human metabolite
palmitic acid
Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.		2.1310long-chain fatty acid;
straight-chain saturated fatty acid		algal metabolite;
Daphnia magna metabolite;
EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor;
plant metabolite
vanillin
Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).		2.1310benzaldehydes;
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.		2.0310aminonaphthalene;
naphthalenesulfonic acid		fluorescent probe
aspirin
Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.		2.0110benzoic acids;
phenyl acetates;
salicylates		anticoagulant;
antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
EC 1.1.1.188 (prostaglandin-F synthase) inhibitor;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
plant activator;
platelet aggregation inhibitor;
prostaglandin antagonist;
teratogenic agent
benzyl isothiocyanate
benzyl isothiocyanate: inhibits carcinogen-induced neoplasia; structure in Negwer, 5th ed, #715; also promotes urinary bladder carcinoma		2.0110benzenes;
isothiocyanate		antibacterial drug
bis(2-guanidinoethyl)disulfide
bis(2-guanidinoethyl)disulfide: bifunctional cation; RN given refers to parent cpd; structure		2.0210
ethidium
Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.		2.0710phenanthridinesfluorochrome;
intercalator
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.		2.0110aromatic 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
kojic acid
[no description available]		2.13104-pyranones;
enol;
primary alcohol		Aspergillus metabolite;
EC 1.10.3.1 (catechol oxidase) inhibitor;
EC 1.10.3.2 (laccase) inhibitor;
EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor;
EC 1.14.18.1 (tyrosinase) inhibitor;
EC 1.4.3.3 (D-amino-acid oxidase) inhibitor;
NF-kappaB inhibitor;
skin lightening agent
ethylmaleimide
Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.		2.0110maleimidesanticoronaviral agent;
EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor;
EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor;
EC 2.7.1.1 (hexokinase) inhibitor
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.		1.9910nitrosaminecarcinogenic agent;
hepatotoxic agent;
mutagen
4-nitroquinoline-1-oxide
4-nitroquinoline N-oxide : A quinoline N-oxide carrying a nitro substituent at position 4.		1.9910C-nitro compound;
quinoline N-oxide		carcinogenic 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.		2.0710ortho-fused polycyclic arene;
tetraphenes		carcinogenic agent
bromodeoxyuridine
Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.		1.9910pyrimidine 2'-deoxyribonucleosideantimetabolite;
antineoplastic agent
tyrosine
Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.		2.0110amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid;
tyrosine		EC 1.3.1.43 (arogenate dehydrogenase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
dimethylnitrosamine
Dimethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties. It causes serious liver damage and is a hepatocarcinogen in rodents.		210nitrosaminegeroprotector;
mutagen
fluocinolone acetonide
Fluocinolone Acetonide: A glucocorticoid derivative used topically in the treatment of various skin disorders. It is usually employed as a cream, gel, lotion, or ointment. It has also been used topically in the treatment of inflammatory eye, ear, and nose disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732). fluocinolone acetonide : A fluorinated steroid that is flunisolide in which the hydrogen at position 9 is replaced by fluorine. A corticosteroid with glucocorticoid activity, it is used (both as the anhydrous form and as the dihydrate) in creams, gels and ointments for the treatment of various skin disorders.		2.071011beta-hydroxy steroid;
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(1),Delta(4)-steroid;
cyclic ketal;
fluorinated steroid;
glucocorticoid;
organic heteropentacyclic compound;
primary alpha-hydroxy ketone		anti-inflammatory drug;
antipruritic drug
dinitrofluorobenzene
Dinitrofluorobenzene: Irritants and reagents for labeling terminal amino acid groups.. 1-fluoro-2,4-dinitrobenzene : The organofluorine compound that is benzene with a fluoro substituent at the 1-position and two nitro substituents in the 2- and 4-positions.		2.1110C-nitro compound;
organofluorine compound		agrochemical;
allergen;
chromatographic reagent;
EC 2.7.3.2 (creatine kinase) inhibitor;
protein-sequencing agent;
spectrophotometric reagent
4-hydroxypropiophenone
[no description available]		2.1310acetophenones
benzohydrol
diphenylmethanol : A secondary alcohol that is diphenylmethane which carries a hydroxy group at position 1.		2.1110benzyl alcohols;
secondary alcohol		bacterial xenobiotic metabolite;
human urinary metabolite;
human xenobiotic metabolite;
rat metabolite
methyleugenol
methyleugenol: structure		2.4220phenylpropanoid
acetyleugenol
acetyleugenol: from cloves; inhibits arachidonate-, adrenaline-, & collagen-induced platelet aggregation		2.0110benzoate ester;
phenols
catechin
Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.		3.5720catechinantioxidant;
plant metabolite
pyrazines
Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.		2.1110diazine;
pyrazines		Daphnia magna 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.		2.4420acetylcysteine;
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
nitrosobenzylmethylamine
nitrosobenzylmethylamine: structure		210
phenethyl isothiocyanate
phenethyl isothiocyanate: a dietary liver aldehyde dehydrogenase inhibitor; promotes urinary bladder carcinoma. phenethyl isothiocyanate : An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.		2.0310isothiocyanateantineoplastic agent;
EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor;
metabolite
tetradecanoylphorbol acetate
Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.		2.7130acetate 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
azoxymethane
Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.		2.730
ng-nitroarginine methyl ester
NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.		2.0110alpha-amino acid ester;
L-arginine derivative;
methyl ester;
N-nitro compound		EC 1.14.13.39 (nitric oxide synthase) inhibitor
1'-hydroxyestragole
1'-hydroxyestragole: structure		2.0210
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid
[no description available]		2.0310chromanol;
monocarboxylic acid;
phenols		antioxidant;
ferroptosis inhibitor;
neuroprotective agent;
radical scavenger;
Wnt signalling inhibitor
nitrosobis(2-oxopropyl)amine
nitrosobis(2-oxopropyl)amine: structure. nitrosobis(2-oxopropyl)amine : A nitrosamine that is iminodiacetone that is substituted by a nitroso group at the N-atom. It induces pancreatic ductal adenocarcinomas in Syrian golden hamsters (other rodents are not susceptible).		710ketone;
nitrosamine		carcinogenic agent
epigallocatechin gallate
epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.		3.5720flavans;
gallate ester;
polyphenol		antineoplastic agent;
antioxidant;
apoptosis inducer;
geroprotector;
Hsp90 inhibitor;
neuroprotective agent;
plant metabolite
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.		7.4220phenols;
phenylpropanoid
2-hydroxychavicol
2-hydroxychavicol: antimutagen from betel leaf; structure given in first source		2.4220
nobiletin
nobiletin : A methoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 8, 3' and 4' respectively.		9.0440methoxyflavoneantineoplastic agent;
plant metabolite
s-ethyl glutathione
[no description available]		2.0310oligopeptide
bortezomib
[no description available]		2.1110amino acid amide;
L-phenylalanine derivative;
pyrazines		antineoplastic agent;
antiprotozoal drug;
protease inhibitor;
proteasome inhibitor
epiglucan
epiglucan: a highly side-chain/branched alkali-insoluble cell wall glucan from fungus such as Epicoccum nigrum, Botrytis cinerea, ascomycetes & basidiomycetes; also isolated S-4001 from Lei Wan (polyporus mylitiae), HA-beta-glucan from mushroom Pleutotus ostreatus (Fr.) Quel., and translam from seaweed Laminaria cichorioides; with commercially important functional properties including emulsification and friction reduction.		2.1110
laminaran
beta-1,3-glucan: component of fungal cell walls; also used as antitumor polysaccharide; unspecified D usually means BETA-GLUCANS; beta-1,3-D-glucan is also available; glucan phosphate is also available; biosynthesis is inhibited by echinocandins (cyclic hexapeptides). laminarin : A polysaccharide composed of beta-(1->3)-linked glucose residues containing sporadic beta-(1->6)-linkages as branch points or inter-residue linkages and 2-3% D-mannitol at some reducing termini.		2.1110
arbutin
hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.		2.1310beta-D-glucoside;
monosaccharide derivative		Escherichia coli metabolite;
plant metabolite
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		2.4220cinnamic acidplant metabolite
tretinoin
Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.		2.0510retinoic acid;
vitamin A		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
AP-1 antagonist;
human metabolite;
keratolytic drug;
retinoic acid receptor agonist;
retinoid X receptor agonist;
signalling molecule
resveratrol
trans-resveratrol : A resveratrol in which the double bond has E configuration.		3.5320resveratrolantioxidant;
phytoalexin;
plant metabolite;
quorum sensing inhibitor;
radical scavenger
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.		2.42202-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.		2.42203-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.		2.01104-coumaric acidfood 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.		2.4220sinapic acidMALDI matrix material;
plant metabolite
stilbenes
Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.		3.5320stilbene
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.		2.7330cinnamaldehydesapoptosis inducer;
EC 1.14.13.39 (nitric oxide synthase) inhibitor;
plant metabolite
sesquiterpenes
[no description available]		4.7450
caffeic acid
trans-caffeic acid : The trans-isomer of caffeic acid.		2.4220caffeic acidgeroprotector;
mouse metabolite
4-methoxycinnamic acid
[no description available]		2.4220cinnamic 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.		2.4220methoxycinnamic acid
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.		4.0520aromatic 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
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.		2.1310guaiacols;
phenylpropanoid		animal metabolite;
monolignol;
mouse metabolite;
pheromone;
plant metabolite;
volatile oil component
aurapten
aurapten: RN refers to (E)-isomer; structure given in first source. auraptene : A member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group. Ii is isolated from several edible fruits and vegetables and exhibits a variety of therapeutic properties.		9.2350coumarins;
monoterpenoid		antihypertensive agent;
antineoplastic agent;
antioxidant;
apoptosis inducer;
dopaminergic agent;
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor;
gamma-secretase modulator;
gastrointestinal drug;
hepatoprotective agent;
matrix metalloproteinase inhibitor;
neuroprotective agent;
plant metabolite;
PPARalpha agonist;
vulnerary
u 0126
U 0126: protein kinase kinase inhibitor; structure in first source		2.1510aryl sulfide;
dinitrile;
enamine;
substituted aniline		antineoplastic agent;
antioxidant;
apoptosis inducer;
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor;
osteogenesis regulator;
vasoconstrictor agent
ovalbumin
Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.		7.0810
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.		3.1310prostaglandins Ehuman metabolite;
mouse metabolite;
oxytocic
luteolin
[no description available]		2.01103'-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
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.		2.73304-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.		2.1310cinnamaldehydes;
guaiacols;
phenylpropanoid		antifungal agent;
plant metabolite
genistein
[no description available]		2.01107-hydroxyisoflavonesantineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
geroprotector;
human urinary metabolite;
phytoestrogen;
plant metabolite;
tyrosine kinase inhibitor
galangin
5,7-dihydroxyflavonol: antimicrobial from the twigs of Populus nigra x Populus deltoides; structure in first source. galangin : A 7-hydroxyflavonol with additional hydroxy groups at positions 3 and 5 respectively; a growth inhibitor of breast tumor cells.		2.21107-hydroxyflavonol;
trihydroxyflavone		antimicrobial agent;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
plant metabolite
caffeic acid phenethyl ester
phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.		2.0210alkyl caffeate esteranti-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.		2.0110amidobenzoic acid;
cinnamamides;
dimethoxybenzene;
secondary carboxamide		anti-allergic agent;
anti-asthmatic drug;
antineoplastic agent;
aryl hydrocarbon receptor agonist;
calcium channel blocker;
hepatoprotective agent;
nephroprotective agent
ketotifen fumarate
ketotifen fumarate : An organoammonium salt consisting of equimolar amounts of ketotifen(1+) and fumarate(1-) ions. A blocker of histamine H1 receptors with a stabilising action on mast cells, it is a non-bronchodilator anti-asthmatic drug.		2.0510organoammonium saltanti-asthmatic drug;
H1-receptor antagonist
herbimycin
herbimycin: herbicidal antibiotic produced by Streptomyces sp.; see also herbimycin B; structure for herbimycin A in second source. herbimycin : A 19-membered macrocyle incorporating a benzoquinone ring and a lactam functionality. It is an ansamycin antibiotic that induces apoptosis and displays antitumour effects.		2.01101,4-benzoquinones;
lactam;
macrocycle		antimicrobial agent;
apoptosis inducer;
herbicide;
Hsp90 inhibitor;
tyrosine kinase inhibitor
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.		9.7450cyclic ketone;
sesquiterpenoid		anti-inflammatory agent;
glioma-associated oncogene inhibitor;
plant metabolite
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.		2.0310ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
warfarin
Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.		4.3960benzenes;
hydroxycoumarin;
methyl ketone
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.		3.150nucleobase analogue;
organic heterobicyclic compound		antimetabolite;
EC 1.17.3.2 (xanthine oxidase) inhibitor;
gout suppressant;
radical scavenger
ConditionIndicatedRelationship StrengthStudiesTrials
Acquired Immune Deficiency Syndrome
[description not available]		02.0510
Acquired Immunodeficiency Syndrome
An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.		02.0510
HIV Coinfection
[description not available]		02.4420
HIV Infections
Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).		02.4420
Kahler Disease
[description not available]		02.9740
Multiple Myeloma
A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.		02.9740
Innate Inflammatory Response
[description not available]		04.2960
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.		04.2960
Breast Cancer
[description not available]		03.3560
Breast Neoplasms
Tumors or cancer of the human BREAST.		03.3560
Amentia
[description not available]		03.1710
Benign Neoplasms
[description not available]		04.2460
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.		03.1710
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.		04.2460
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).		03.1710
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.5520
Primary Peritonitis
[description not available]		02.3110
Peritonitis
INFLAMMATION of the PERITONEUM lining the ABDOMINAL CAVITY as the result of infectious, autoimmune, or chemical processes. Primary peritonitis is due to infection of the PERITONEAL CAVITY via hematogenous or lymphatic spread and without intra-abdominal source. Secondary peritonitis arises from the ABDOMINAL CAVITY itself through RUPTURE or ABSCESS of intra-abdominal organs.		02.3110
Cancer of Cervix
[description not available]		02.5220
Uterine Cervical Neoplasms
Tumors or cancer of the UTERINE CERVIX.		02.5220
Cell Transformation, Neoplastic
Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.		02.5120
Malignant Melanoma
[description not available]		02.1510
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		07.1510
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.4420
Asthma, Bronchial
[description not available]		02.0810
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).		07.0810
Carcinoma, Epidermoid
[description not available]		02.7630
Cancer of Head
[description not available]		02.0810
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)		02.7630
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)		02.0810
Hepatocellular Carcinoma
[description not available]		07.4420
Cancer of Liver
[description not available]		02.4420
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.		02.4420
Liver Neoplasms
Tumors or cancer of the LIVER.		02.4420
Bone Cancer
[description not available]		02.110
Bone Neoplasms
Tumors or cancer located in bone tissue or specific BONES.		02.110
Contact Dermatitis
[description not available]		07.1110
Dermatitis, Contact
A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.		02.1110
Aging
The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.		02.1310
Carcinoma, Non-Small Cell Lung
[description not available]		02.1510
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.		02.1510
Adjuvant Arthritis
[description not available]		02.0310
Bone Loss, Osteoclastic
[description not available]		02.4420
Carcinoma, Ehrlich Tumor
A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.		03.1250
Cancer of Skin
[description not available]		02.4720
Skin Neoplasms
Tumors or cancer of the SKIN.		02.4720
Angiogenesis, Pathologic
[description not available]		02.0610
Cancer of Prostate
[description not available]		02.0610
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.0610
Cancer of Colon
[description not available]		02.4220
Colonic Neoplasms
Tumors or cancer of the COLON.		02.4220
Koch's Disease
[description not available]		02.0710
Tuberculosis
Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.		02.0710
Carcinoma, Anaplastic
[description not available]		02.0810
Carcinoma
A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.		07.0810
Cancer of Mouth
[description not available]		02.0710
Mouth Neoplasms
Tumors or cancer of the MOUTH.		02.0710
Gastroduodenal Ulcer
[description not available]		02.0110
Peptic Ulcer
Ulcer that occurs in the regions of the GASTROINTESTINAL TRACT which come into contact with GASTRIC JUICE containing PEPSIN and GASTRIC ACID. It occurs when there are defects in the MUCOSA barrier. The common forms of peptic ulcers are associated with HELICOBACTER PYLORI and the consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).		02.0110
Acute Promyelocytic Leukemia
[description not available]		02.0210
Leukemia, Promyelocytic, Acute
An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.		02.0210
Condition, Preneoplastic
[description not available]		02.9140
Cancer of the Tongue
[description not available]		01.9910
Precancerous Conditions
Pathological conditions that tend eventually to become malignant.		02.9140
Tongue Neoplasms
Tumors or cancer of the TONGUE.		01.9910
Colonic Diseases
Pathological processes in the COLON region of the large intestine (INTESTINE, LARGE).		01.9910
Experimental Hepatoma
[description not available]		01.9910
Cancer of Esophagus
[description not available]		0210
Esophageal Neoplasms
Tumors or cancer of the ESOPHAGUS.		0210
Cholangiocellular Carcinoma
[description not available]		0210
Adenocarcinoma, Basal Cell
[description not available]		0210
Adenoma, Basal Cell
[description not available]		0210
Bile Duct Cancer
[description not available]		0210
Cancer of Pancreas
[description not available]		0210
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		0210
Adenoma
A benign epithelial tumor with a glandular organization.		0210
Bile Duct Neoplasms
Tumors or cancer of the BILE DUCTS.		0210
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).		0210
Cholangiocarcinoma
A malignant tumor arising from the epithelium of the BILE DUCTS.		0210