Compounds > benzyl caffeate
Page last updated: 2024-12-11

benzyl caffeate

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Description

benzyl caffeate: isolated from Liaoxi propolis [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5919576
CHEMBL ID133714
MeSH IDM0296830

Synonyms (32)

Synonym
(e)-3-(3,4-dihydroxy-phenyl)-acrylic acid benzyl ester
phenylmethyl 1-(3'',4''-dihydroxyphenyl)propenate
bdbm50029198
3-(3,4-dihydroxy-phenyl)-acrylic acid benzyl ester
(e)-benzyl 3-(3,4-dihydroxyphenyl)acrylate
benzyl 3,4-dihydroxycinnamate
nsc-666590
benzyl caffeate
MEGXP0_000689
2-propenoic acid, 3-(3,4-dihydroxyphenyl)-, phenylmethyl ester, (2z)-
benzyl (e)-3-(3,4-dihydroxyphenyl)prop-2-enoate
nsc666590
benzyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate
benzyl 3-(3,4-dihydroxyphenyl)acrylate
CHEMBL133714 ,
phenylmethyl 1-(3',4'-dihydroxyphenyl)propenate
A801008
benzyl (e)-3-(3,4-dihydroxyphenyl)prop-2-enoate;phenethyl 3-(3,4-dihydroxyphenyl)acrylate
phenylmethyl 3-(3,4-dihydroxyphenyl)-2-propenoate
unii-bd29sjl432
phenylmethyl caffeate
107843-77-6
2-propenoic acid, 3-(3,4-dihydroxyphenyl)-, phenylmethyl ester
nsc 666590
bd29sjl432 ,
130734-47-3
caffeic acid benzyl ester
J-501993
benzyl (e)-3-(3,4-dihydroxyphenyl)acrylate
CS-0363076
caffeicacidbenzylester-d5
(e)-benzyl3-(3,4-dihydroxyphenyl)acrylate

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Druglike derivatives 13, 15, and 16 were predicted to cross the blood-brain barrier in vitro and were significantly less toxic than tolcapone and entacapone when incubated at 50 μM with rat primary hepatocytes."( Development of Blood-Brain Barrier Permeable Nitrocatechol-Based Catechol O-Methyltransferase Inhibitors with Reduced Potential for Hepatotoxicity.
Borges, F; Garrido, J; Martínez, A; Martínez-González, L; Mohamed, T; Pérez, DI; Rao, PP; Remião, F; Serrão, P; Shakeri, A; Silva, T; Soares-da-Silva, P; Uriarte, E; Valente, MJ, 2016)		0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Aldo-keto reductase family 1 member B10Homo sapiens (human)IC50 (µMol)0.21000.00101.94459.6000AID641086
Aldo-keto reductase family 1 member B1Homo sapiens (human)IC50 (µMol)0.40000.00101.191310.0000AID641085
Integrase Human immunodeficiency virus 1IC50 (µMol)39.30420.00051.544310.0000AID371216; AID91430; AID91579
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TransthyretinHomo sapiens (human)EC50 (µMol)16.00005.60007.54298.6000AID1169291
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (19)

Processvia Protein(s)Taxonomy
retinoid metabolic processAldo-keto reductase family 1 member B10Homo sapiens (human)
farnesol catabolic processAldo-keto reductase family 1 member B10Homo sapiens (human)
retinol metabolic processAldo-keto reductase family 1 member B10Homo sapiens (human)
daunorubicin metabolic processAldo-keto reductase family 1 member B10Homo sapiens (human)
doxorubicin metabolic processAldo-keto reductase family 1 member B10Homo sapiens (human)
cellular detoxification of aldehydeAldo-keto reductase family 1 member B10Homo sapiens (human)
signal transductionTransthyretinHomo sapiens (human)
purine nucleobase metabolic processTransthyretinHomo sapiens (human)
retinoid metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
epithelial cell maturationAldo-keto reductase family 1 member B1Homo sapiens (human)
renal water homeostasisAldo-keto reductase family 1 member B1Homo sapiens (human)
carbohydrate metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
prostaglandin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
C21-steroid hormone biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
L-ascorbic acid biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
regulation of urine volumeAldo-keto reductase family 1 member B1Homo sapiens (human)
retinol metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
negative regulation of apoptotic processAldo-keto reductase family 1 member B1Homo sapiens (human)
daunorubicin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
doxorubicin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
fructose biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
cellular hyperosmotic salinity responseAldo-keto reductase family 1 member B1Homo sapiens (human)
metanephric collecting duct developmentAldo-keto reductase family 1 member B1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
retinal dehydrogenase activityAldo-keto reductase family 1 member B10Homo sapiens (human)
aldo-keto reductase (NADPH) activityAldo-keto reductase family 1 member B10Homo sapiens (human)
protein bindingAldo-keto reductase family 1 member B10Homo sapiens (human)
alcohol dehydrogenase (NADP+) activityAldo-keto reductase family 1 member B10Homo sapiens (human)
geranylgeranyl reductase activityAldo-keto reductase family 1 member B10Homo sapiens (human)
allyl-alcohol dehydrogenase activityAldo-keto reductase family 1 member B10Homo sapiens (human)
indanol dehydrogenase activityAldo-keto reductase family 1 member B10Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activityAldo-keto reductase family 1 member B10Homo sapiens (human)
aldose reductase (NADPH) activityAldo-keto reductase family 1 member B10Homo sapiens (human)
hormone activityTransthyretinHomo sapiens (human)
protein bindingTransthyretinHomo sapiens (human)
identical protein bindingTransthyretinHomo sapiens (human)
thyroid hormone bindingTransthyretinHomo sapiens (human)
retinal dehydrogenase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
aldose reductase (NADPH) activityAldo-keto reductase family 1 member B1Homo sapiens (human)
protein bindingAldo-keto reductase family 1 member B1Homo sapiens (human)
electron transfer activityAldo-keto reductase family 1 member B1Homo sapiens (human)
prostaglandin H2 endoperoxidase reductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
glyceraldehyde oxidoreductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
allyl-alcohol dehydrogenase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
L-glucuronate reductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
glycerol dehydrogenase [NADP+] activityAldo-keto reductase family 1 member B1Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activityAldo-keto reductase family 1 member B1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
extracellular regionAldo-keto reductase family 1 member B10Homo sapiens (human)
lysosomeAldo-keto reductase family 1 member B10Homo sapiens (human)
cytosolAldo-keto reductase family 1 member B10Homo sapiens (human)
cytosolAldo-keto reductase family 1 member B10Homo sapiens (human)
mitochondrionAldo-keto reductase family 1 member B10Homo sapiens (human)
extracellular regionTransthyretinHomo sapiens (human)
extracellular spaceTransthyretinHomo sapiens (human)
azurophil granule lumenTransthyretinHomo sapiens (human)
extracellular exosomeTransthyretinHomo sapiens (human)
extracellular spaceTransthyretinHomo sapiens (human)
extracellular spaceAldo-keto reductase family 1 member B1Homo sapiens (human)
nucleoplasmAldo-keto reductase family 1 member B1Homo sapiens (human)
cytosolAldo-keto reductase family 1 member B1Homo sapiens (human)
extracellular exosomeAldo-keto reductase family 1 member B1Homo sapiens (human)
cytosolAldo-keto reductase family 1 member B1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (44)

Assay IDTitleYearJournalArticle
AID1161634Antitumor activity against human SiHa cells assessed as inhibition of cell growth by MTT assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis and antitumor activity of feruloyl and caffeoyl derivatives.
AID371219Cytotoxicity against human A549 cells by MTT assay2008Bioorganic & medicinal chemistry letters, Dec-15, Volume: 18, Issue:24
Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.
AID1179758Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins by spectrophotometry2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
Phenylpropanoid acid esters from Korean propolis and their antioxidant activities.
AID334276Antiproliferative activity against human HT1080 cells after 72 hrs by MTT assay2002Journal of natural products, May, Volume: 65, Issue:5
Constituents of Chinese propolis and their antiproliferative activities.
AID1632018Inhibition of S-COMT in Wistar rat liver assessed as metanephrine formation preincubated for 20 mins followed by addition of adrenaline as substrate and SAM measured after 5 mins by chromatographic analysis2016Journal of medicinal chemistry, 08-25, Volume: 59, Issue:16
Development of Blood-Brain Barrier Permeable Nitrocatechol-Based Catechol O-Methyltransferase Inhibitors with Reduced Potential for Hepatotoxicity.
AID1169299Competitive binding to TTR V30M mutant (unknown origin) expressed in Escherichia coli at 1 to 80 uM by fluorescence assay2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
AID780242Cytotoxicity against human LNCAP cells assessed as reduction in cell viability after 24 hrs by WST-1 assay2013Bioorganic & medicinal chemistry, Nov-15, Volume: 21, Issue:22
Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells.
AID339078Antiviral activity against influenza A virus (A/Hong Kong/1/1968(H3N2)) infected in hen chorioallantoic membrane assessed as minimum drug level causing inhibition of viral infectivity after 48 hrs1992Journal of natural products, Mar, Volume: 55, Issue:3
Anti-influenza virus effect of some propolis constituents and their analogues (esters of substituted cinnamic acids).
AID1632021Permeability of the compound in PBS:EtOH (70:30) measured after 2 hrs and 30 mins by PAMPA-BBB assay2016Journal of medicinal chemistry, 08-25, Volume: 59, Issue:16
Development of Blood-Brain Barrier Permeable Nitrocatechol-Based Catechol O-Methyltransferase Inhibitors with Reduced Potential for Hepatotoxicity.
AID1161635Antitumor activity against human Bewo cells assessed as inhibition of cell growth by MTT assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis and antitumor activity of feruloyl and caffeoyl derivatives.
AID1161633Antitumor activity against human HeLa cells assessed as inhibition of cell growth by MTT assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis and antitumor activity of feruloyl and caffeoyl derivatives.
AID334277Antiproliferative activity against human A549 cells after 72 hrs by MTT assay2002Journal of natural products, May, Volume: 65, Issue:5
Constituents of Chinese propolis and their antiproliferative activities.
AID334275Antiproliferative activity against mouse B16-BL6 cells after 72 hrs by MTT assay2002Journal of natural products, May, Volume: 65, Issue:5
Constituents of Chinese propolis and their antiproliferative activities.
AID339080Toxicity in hen chorioallantoic membrane assessed as maximum tolerable concentration causing no morphological changes1992Journal of natural products, Mar, Volume: 55, Issue:3
Anti-influenza virus effect of some propolis constituents and their analogues (esters of substituted cinnamic acids).
AID334280DPPH radical scavenging activity after 30 mins2002Journal of natural products, May, Volume: 65, Issue:5
Constituents of Chinese propolis and their antiproliferative activities.
AID371217Cytotoxicity against human Bel7402 cells by MTT assay2008Bioorganic & medicinal chemistry letters, Dec-15, Volume: 18, Issue:24
Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.
AID334279Antiproliferative activity against mouse 26-L5 cells after 72 hrs by MTT assay2002Journal of natural products, May, Volume: 65, Issue:5
Constituents of Chinese propolis and their antiproliferative activities.
AID1179757Antioxidant activity assessed as ABTS radical scavenging activity after 12 hrs by spectrophotometry2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
Phenylpropanoid acid esters from Korean propolis and their antioxidant activities.
AID91579Inhibitory activity against HIV-1 Integrase (HIV-1-IN)2002Journal of medicinal chemistry, Feb-14, Volume: 45, Issue:4
CoMFA and CoMSIA 3D QSAR and docking studies on conformationally-restrained cinnamoyl HIV-1 integrase inhibitors: exploration of a binding mode at the active site.
AID371220Cytotoxicity against human BCG823 cells by MTT assay2008Bioorganic & medicinal chemistry letters, Dec-15, Volume: 18, Issue:24
Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.
AID780232Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins by spectrophotometry2013Bioorganic & medicinal chemistry, Nov-15, Volume: 21, Issue:22
Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells.
AID1179763Ratio of compound IC50 to trolox IC50 for DPPH radical scavenging activity after 30 mins by spectrophotometry2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
Phenylpropanoid acid esters from Korean propolis and their antioxidant activities.
AID641084Selectivity ratio of IC50 for human recombinant N-terminus His6-tagged AKR1B1 to IC50 for human recombinant N-terminus His6-tagged AKR1B102012European journal of medicinal chemistry, Feb, Volume: 48Design, synthesis and evaluation of caffeic acid phenethyl ester-based inhibitors targeting a selectivity pocket in the active site of human aldo-keto reductase 1B10.
AID449663Lipophilicity, log P of the compound2009European journal of medicinal chemistry, Nov, Volume: 44, Issue:11
Antinociceptive properties of caffeic acid derivatives in mice.
AID780240Antiproliferative activity against human LNCAP cells after 72 hrs in presence of DHT2013Bioorganic & medicinal chemistry, Nov-15, Volume: 21, Issue:22
Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells.
AID362057Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells assessed as nitrite accumulation administered 1 hr before LPS challenge and measured after 24 hrs by Griess reagent assay2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages.
AID362056Cytotoxicity against mouse RAW264.7 cells assessed as cell survival after 24 hrs by MTT assay2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages.
AID449642Antinociceptive activity in Swiss mouse by inhibition of acetic acid-induced abdominal constriction at 10 mg/kg, ip after 20 mins2009European journal of medicinal chemistry, Nov, Volume: 44, Issue:11
Antinociceptive properties of caffeic acid derivatives in mice.
AID641086Inhibition of human recombinant N-terminus His6-tagged AKR1B10 expressed in Escherichia coli BL21 DE3 assessed as pyridine-3-aldehyde reduction by spectrometric analysis2012European journal of medicinal chemistry, Feb, Volume: 48Design, synthesis and evaluation of caffeic acid phenethyl ester-based inhibitors targeting a selectivity pocket in the active site of human aldo-keto reductase 1B10.
AID1179762Ratio of compound IC50 to trolox IC50 for ABTS radical scavenging activity after 12 hrs by spectrophotometry2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
Phenylpropanoid acid esters from Korean propolis and their antioxidant activities.
AID339079Antiviral activity against influenza A virus (A/Puerto Rico/8/34(H1N1)) infected in hen chorioallantoic membrane assessed as minimum drug level causing inhibition of viral infectivity after 48 hrs1992Journal of natural products, Mar, Volume: 55, Issue:3
Anti-influenza virus effect of some propolis constituents and their analogues (esters of substituted cinnamic acids).
AID1161638Antitumor activity against human HepG2 cells assessed as inhibition of cell growth by MTT assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis and antitumor activity of feruloyl and caffeoyl derivatives.
AID1161636Antitumor activity against human HL60 cells assessed as inhibition of cell growth by MTT assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis and antitumor activity of feruloyl and caffeoyl derivatives.
AID91430In vitro inhibitory activity against HIV-1 integrase.1995Journal of medicinal chemistry, Oct-13, Volume: 38, Issue:21
Hydroxylated aromatic inhibitors of HIV-1 integrase.
AID1169291Inhibition of TTR V30M mutant (unknown origin) expressed in Escherichia coli assessed as inhibition of amyloid fibril formation by fluorescence assay2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
AID1542227Inhibition of synthetic AcPHF6 peptide aggregation in pH 7.4 phosphate buffer assessed as reduction in fluorescence intensity at 50 uM and measured every minute over 2 hrs with 5 secs shaking prior to each reading by ThT fluorescence assay2019European journal of medicinal chemistry, Apr-01, Volume: 167Repurposing nitrocatechols: 5-Nitro-α-cyanocarboxamide derivatives of caffeic acid and caffeic acid phenethyl ester effectively inhibit aggregation of tau-derived hexapeptide AcPHF6.
AID641085Inhibition of human recombinant N-terminus His6-tagged AKR1B1 expressed in Escherichia coli BL21 DE3 assessed as pyridine-3-aldehyde reduction by spectrometric analysis2012European journal of medicinal chemistry, Feb, Volume: 48Design, synthesis and evaluation of caffeic acid phenethyl ester-based inhibitors targeting a selectivity pocket in the active site of human aldo-keto reductase 1B10.
AID1632019Inhibition of MB-COMT in Wistar rat brain assessed as metanephrine formation preincubated for 20 mins followed by addition of adrenaline as substrate and SAM measured after 15 mins by chromatographic analysis2016Journal of medicinal chemistry, 08-25, Volume: 59, Issue:16
Development of Blood-Brain Barrier Permeable Nitrocatechol-Based Catechol O-Methyltransferase Inhibitors with Reduced Potential for Hepatotoxicity.
AID371216Inhibition of HIV1 integrase by ELISA2008Bioorganic & medicinal chemistry letters, Dec-15, Volume: 18, Issue:24
Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.
AID362058Ratio of EC50 for mouse RAW264.7 cells to EC50 for inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages.
AID371218Cytotoxicity against human MCF7 cells by MTT assay2008Bioorganic & medicinal chemistry letters, Dec-15, Volume: 18, Issue:24
Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.
AID1161637Antitumor activity against human SGC7901 cells assessed as inhibition of cell growth by MTT assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis and antitumor activity of feruloyl and caffeoyl derivatives.
AID1179760Antioxidant activity assessed as hydroxyl radical scavenging activity at 50 uM after 30 mins by Fenton reaction-induced DNA single strand breakage method2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
Phenylpropanoid acid esters from Korean propolis and their antioxidant activities.
AID334278Antiproliferative activity against human HeLa cells after 72 hrs by MTT assay2002Journal of natural products, May, Volume: 65, Issue:5
Constituents of Chinese propolis and their antiproliferative activities.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (20.00)18.2507
2000's5 (33.33)29.6817
2010's7 (46.67)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.93

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.93 (24.57)
Research Supply Index2.77 (2.92)
Research Growth Index4.70 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.93)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
protocatechuic acid
protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.		2.2110catechols;
dihydroxybenzoic acid		antineoplastic agent;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor;
human xenobiotic metabolite;
plant metabolite
gallic acid
gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.		2.2110trihydroxybenzoic acidantineoplastic agent;
antioxidant;
apoptosis inducer;
astringent;
cyclooxygenase 2 inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
geroprotector;
human xenobiotic metabolite;
plant metabolite
acetaminophen
Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.		2.0510acetamides;
phenols		antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
cyclooxygenase 3 inhibitor;
environmental contaminant;
ferroptosis inducer;
geroprotector;
hepatotoxic agent;
human blood serum metabolite;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic
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.		2.0510benzoic 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
diflunisal
Diflunisal: A salicylate derivative and anti-inflammatory analgesic with actions and side effects similar to those of ASPIRIN.. diflunisal : An organofluorine compound comprising salicylic acid having a 2,4-difluorophenyl group at the 5-position.		2.110monohydroxybenzoic acid;
organofluorine compound		non-narcotic analgesic;
non-steroidal anti-inflammatory drug
fluorouracil
Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.		2.0110nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
masoprocol
nordihydroguaretic acid: antioxidant compound found in the creosote bush (Larrea tridentata)		2.110catechols;
lignan;
tetrol		antioxidant;
ferroptosis inhibitor;
geroprotector;
plant metabolite
phenylethyl alcohol
Phenylethyl Alcohol: An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery.. 2-phenylethanol : A primary alcohol that is ethanol substituted by a phenyl group at position 2.		2.0110benzenes;
primary alcohol		Aspergillus metabolite;
fragrance;
plant growth retardant;
plant metabolite;
Saccharomyces cerevisiae metabolite
undecan-1-ol
undecan-1-ol : A primary alcohol that is undecane substituted by a hydroxy group at position 1.. undecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of eleven carbon atoms.		2.0410primary alcohol;
undecanol		flavouring agent;
plant metabolite
orange g
orange G : An organic sodium salt that is the disodium salt of 7-hydroxy-8-[(E)-phenyldiazenyl]naphthalene-1,3-disulfonic acid. It is often combined with other yellow dyes in alcoholic solution to stain erythrocytes in trichrome methods, and is used for demonstrating cells in the pancreas and pituitary.		2.2110
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid
[no description available]		2.110chromanol;
monocarboxylic acid;
phenols		antioxidant;
ferroptosis inhibitor;
neuroprotective agent;
radical scavenger;
Wnt signalling inhibitor
pinocembrin
pinocembrin : A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea.		2.0110(2S)-flavan-4-one;
dihydroxyflavanone		antineoplastic agent;
antioxidant;
metabolite;
neuroprotective agent;
vasodilator agent
sesamin
(+)-sesamin : A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR stereoisomer). Isolated from Cinnamomum camphora, it exhibits cytotoxic activity.		2.110benzodioxoles;
furofuran;
lignan		antineoplastic agent;
neuroprotective agent;
plant metabolite
pinostrobin
[no description available]		2.0110monohydroxyflavanone;
monomethoxyflavanone		antidote;
plant metabolite
matairesinol
matairesinol: lignan that is a central precursor in plants in the biosynthesis of numerous lignans (coordinate with specific); RN refers to (3R-trans)-isomer. (-)-matairesinol : A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).		2.110gamma-lactone;
lignan;
polyphenol		angiogenesis inhibitor;
anti-asthmatic agent;
phytoestrogen;
plant metabolite
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		2.110
doxorubicin hydrochloride
[no description available]		2.0110anthracycline
ferulic acid
ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.		2.0410ferulic acidsanti-inflammatory agent;
antioxidant;
apoptosis inhibitor;
cardioprotective agent;
MALDI matrix material;
plant metabolite
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.		2.52204-coumaric acidfood component;
mouse metabolite;
plant metabolite
isoliquiritigenin
[no description available]		2.0110chalconesantineoplastic agent;
biological pigment;
EC 1.14.18.1 (tyrosinase) inhibitor;
GABA modulator;
geroprotector;
metabolite;
NMDA receptor antagonist
ethyl coumarate
ethyl coumarate: structure in first source		2.2110cinnamate ester
caffeic acid
trans-caffeic acid : The trans-isomer of caffeic acid.		3.5880caffeic acidgeroprotector;
mouse metabolite
methyl caffeate
methyl caffeate: from plant Gaillardia pulchella. methyl caffeate : An alkyl caffeate ester formed by the formal condensation of caffeic acid with methyl alcohol.		3.5480alkyl caffeate ester;
methyl ester
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.		2.0110methoxycinnamic acid
isoferulic acid
isoferulic acid: isomer of ferulic acid; structure. isoferulic acid : A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring.		2.0110ferulic acidsantioxidant;
biomarker;
metabolite
capsaicin
ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.		2.110capsaicinoidnon-narcotic analgesic;
TRPV1 agonist;
voltage-gated sodium channel blocker
cyqualon
cyclovalone: is a synthetic curcumin derivative; structure in first source		2.0110
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.		2.4920cinnamate ester;
tannin		food component;
plant metabolite
1,1-diphenyl-2-picrylhydrazyl
1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)		2.0110
tolcapone
Tolcapone: A benzophenone and nitrophenol compound that acts as an inhibitor of CATECHOL O-METHYLTRANSFERASE, an enzyme involved in the metabolism of DOPAMINE and LEVODOPA. It is used in the treatment of PARKINSON DISEASE in patients for whom levodopa is ineffective or contraindicated.. tolcapone : Benzophenone substituted on one of the phenyl rings at C-3 and C-4 by hydroxy groups and at C-5 by a nitro group, and on the other phenyl ring by a methyl group at C-4. It is an inhibitor of catechol O-methyltransferase.		2.57202-nitrophenols;
benzophenones;
catechols		antiparkinson drug;
EC 2.1.1.6 (catechol O-methyltransferase) inhibitor
apigenin
Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.		2.0110trihydroxyflavoneantineoplastic agent;
metabolite
entacapone
entacapone: structure given in first source. entacapone : A monocarboxylic acid amide that is N,N-diethylprop-2-enamide in which the hydrogen at position 2 is substituted by a cyano group and the hydrogen at the 3E position is substituted by a 3,4-dihydroxy-5-nitrophenyl group.		2.57202-nitrophenols;
catechols;
monocarboxylic acid amide;
nitrile		antidyskinesia agent;
antiparkinson drug;
central nervous system drug;
EC 2.1.1.6 (catechol O-methyltransferase) inhibitor
butein
[no description available]		2.0110chalcones;
polyphenol		antineoplastic agent;
antioxidant;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
geroprotector;
hypoglycemic agent;
plant metabolite;
radiosensitizing agent;
tyrosine kinase inhibitor
chrysin
chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.		2.01107-hydroxyflavonol;
dihydroxyflavone		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
EC 2.7.11.18 (myosin-light-chain kinase) inhibitor;
hepatoprotective agent;
plant metabolite
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.		2.01107-hydroxyflavonol;
trihydroxyflavone		antimicrobial agent;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
plant metabolite
3,4-di-o-caffeoylquinic acid
3,4-di-O-caffeoylquinic acid: isolated from Siphonostegia chinensis		2.0710quinic acid
caffeic acid phenethyl ester
phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.		4.97140alkyl caffeate esteranti-inflammatory agent;
antibacterial agent;
antineoplastic agent;
antioxidant;
antiviral agent;
immunomodulator;
metabolite;
neuroprotective agent
1,1-dimethylallyl caffeic acid ester
1,1-dimethylallyl caffeic acid ester: structure given in first source		2.4720hydroxycinnamic acid
rosmarinic acid
rosmarinic acid: RN given refers to parent cpd; promote OT project. (R)-rosmarinic acid : A stereoisomer of rosmarinic acid having (R)-configuration.. rosmarinic acid : The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.		2.110rosmarinic acidgeroprotector;
plant metabolite
tectochrysin
tectochrysin: structure in first source. tectochrysin : A monohydroxyflavone that is flavone substituted by a hydroxy group at position 4 and a methoxy group at position 7 respectively.		2.0110monohydroxyflavone;
monomethoxyflavone		antidiarrhoeal drug;
antineoplastic agent;
plant metabolite
phenylethyl 3-methylcaffeate
phenylethyl 3-methylcaffeate: a caffeic acid ester present in propolis, a natural resin produced by honey bees; structure given in first source		3.8440
morphine
Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.		2.0510morphinane alkaloid;
organic heteropentacyclic compound;
tertiary amino compound		anaesthetic;
drug allergen;
environmental contaminant;
geroprotector;
mu-opioid receptor agonist;
opioid analgesic;
plant metabolite;
vasodilator agent;
xenobiotic
bisdemethoxycurcumin
curcumin III: structure in first source. bisdemethoxycurcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups.		2.0110beta-diketone;
diarylheptanoid;
enone;
polyphenol		EC 3.2.1.1 (alpha-amylase) inhibitor;
metabolite
ethyl caffeate
(E)-ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate: structure in first source. ethyl trans-caffeate : An ethyl ester resulting from the formal condensation of the carboxy group of trans-caffeic acid with ethanol.		3.76100alkyl caffeate ester;
ethyl ester;
hydroxycinnamic acid		anti-inflammatory agent;
antineoplastic agent;
metabolite
octadecyl caffeate
caffeic acid n-octadecyl ester: isolated from Daphne acutiloba Rehd; structure in first source		2.7530
ag 99
tyrphostin A46: epidermal growth factor-urogastrone receptor antagonist		1.9810
2-Phenylethyl 3-phenyl-2-propenoate
[no description available]		2.7830cinnamate ester
artepillin c
artepillin C: RN refers to (E)-isomer		2.0710
bornyl caffeate
bornyl caffeate: structure in first source		2.4720hydroxycinnamic acid
drupanin
Drupanin: anti-oxidant and anti-cancer; structure in first source		2.0710
indigo carmine
3,5-di-O-(E)-caffeoylquinic acid: from roots of Lychnophora ericoides; structure in first source. 3,5-di-O-caffeoyl quinic acid : A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.		2.0710
hylin
[no description available]		2.0110
propyl caffeate
propyl caffeate: has antioxidant activity; structure in first source		2.9840
octyl caffeate
octyl caffeate: an antioxidant; structure in first source		3.1650
2,3-bis(3'-hydroxybenzyl)butyrolactone, (trans)-isomer
[no description available]		2.110
ks370g
KS370G: antihyperglycemic; structure in first source		2.5320
ConditionIndicatedRelationship StrengthStudiesTrials
Infections, Orthomyxoviridae
[description not available]		02.8910
Orthomyxoviridae Infections
Virus diseases caused by the ORTHOMYXOVIRIDAE.		02.8910
HIV
Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.		01.9810
Cancer of Colon
[description not available]		02.0110
Colonic Neoplasms
Tumors or cancer of the COLON.		02.0110
Ache
[description not available]		02.0510
Pain
An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.		02.0510
Cancer of Prostate
[description not available]		02.0810
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.0810
Amyloid Neuropathy Type 1
[description not available]		02.110
Amyloidosis
A group of sporadic, familial and/or inherited, degenerative, and infectious disease processes, linked by the common theme of abnormal protein folding and deposition of AMYLOID. As the amyloid deposits enlarge they displace normal tissue structures, causing disruption of function. Various signs and symptoms depend on the location and size of the deposits.		02.110
Amyloid Neuropathies, Familial
Inherited disorders of the peripheral nervous system associated with the deposition of AMYLOID in nerve tissue. The different clinical types based on symptoms correspond to the presence of a variety of mutations in several different proteins including transthyretin (PREALBUMIN); APOLIPOPROTEIN A-I; and GELSOLIN.		02.110
Tauopathies
Neurodegenerative disorders involving deposition of abnormal tau protein isoforms (TAU PROTEINS) in neurons and glial cells in the brain. Pathological aggregations of tau proteins are associated with mutation of the tau gene on chromosome 17 in patients with ALZHEIMER DISEASE; DEMENTIA; PARKINSONIAN DISORDERS; progressive supranuclear palsy (SUPRANUCLEAR PALSY, PROGRESSIVE); and corticobasal degeneration.		02.2110
Protein Aggregation, Pathological
A biochemical phenomenon in which misfolded proteins aggregate either intra- or extracellularly. Triggered by factors such as MUTATION; POST-TRANSLATIONAL MODIFICATIONS, and environmental stress, it is generally associated with ALZHEIMER DISEASE; PARKINSON DISEASE; HUNTINGTON DISEASE; and TYPE 2 DIABETES MELLITUS.		02.2110