Compounds > phenylethyl 3-methylcaffeate
Page last updated: 2024-08-01 12:48:47

phenylethyl 3-methylcaffeate

Description

phenylethyl 3-methylcaffeate: a caffeic acid ester present in propolis, a natural resin produced by honey bees; structure given in first source [MeSH]

Cross-References

ID SourceID
PubMed CID5284444
CHEMBL ID442022
SCHEMBL ID14259660
MeSH IDM0247227

Synonyms (43)

Synonym
3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid phenethyl ester
bdbm50029216
(e)-3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid phenethyl ester
phenethyl 3-(4-hydroxy-3-methoxyphenyl)acrylate
phenethyl (e)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoate
nsc666255
.beta.-phenylethyl 4-hydroxy-3-methoxycinnamate
phenylethyl-3-methylcaffeate
2-phenylethyl (2e)-3-[4-hydroxy-3-(methyloxy)phenyl]prop-2-enoate
nsc-671193
nsc-666255
nsc671193
phenylethyl 3-methylcaffeate
2-phenylethyl 3-(4-hydroxy-3-methoxyphenyl)-2-propenoate
ccris 7791
phenyethyl 3-methylcaffeate
2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, 2-phenylethyl ester
CHEMBL442022 ,
caffeic acid 3-methyl phenethyl ester
AKOS015966757
b49b43355j ,
phenylethyl ferulate
3-methylcaffeic acid phenylethyl ester
unii-b49b43355j
2-phenylethyl ferulate
ferulic acid phenethyl ester
phenethyl ferulate
SCHEMBL14259660
2-phenylethyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
caffeicacid,3-methylphenethylester
DTXSID8021143
mfcd18385026
Q27464606
2-phenylethyl (e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
MS-24287
CS-W009964
HY-W009248
phenethyl-trans-ferulate
beta-phenethyl ferulate
132335-98-9
2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, 2-phenylethyl ester, (2e)-
AKOS040760769
phenethyl (e)-3-(4-hydroxy-3-methoxyphenyl)acrylate

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Integrase Human immunodeficiency virus 1IC50100.0000AID91430; AID91579

Activation Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
TransthyretinHomo sapiens (human)EC507.9000AID1169291

Bioassays (14)

Assay IDTitleYearJournalArticle
AID339080Toxicity in hen chorioallantoic membrane assessed as maximum tolerable concentration causing no morphological changes1992Journal of natural products, Mar, Volume: 55, Issue:3
ISSN: 0163-3864		Anti-influenza virus effect of some propolis constituents and their analogues (esters of substituted cinnamic acids).
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
ISSN: 0163-3864		Anti-influenza virus effect of some propolis constituents and their analogues (esters of substituted cinnamic acids).
AID91579Inhibitory activity against HIV-1 Integrase (HIV-1-IN)2002Journal of medicinal chemistry, Feb-14, Volume: 45, Issue:4
ISSN: 0022-2623		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.
AID91430In vitro inhibitory activity against HIV-1 integrase.1995Journal of medicinal chemistry, Oct-13, Volume: 38, Issue:21
ISSN: 0022-2623		Hydroxylated aromatic inhibitors of HIV-1 integrase.
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
ISSN: 1520-4804		Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
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
ISSN: 1520-4804		Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
AID1169300Displacement of ANS from TTR V30M mutant (unknown origin) expressed in Escherichia coli at 1 to 50 uM after 5 mins by fluorescence assay2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
ISSN: 1520-4804		Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
AID1446872Inhibition of recombinant HIV-1 group M subtype B RT-RNase H activity expressed in Escherichia coli M15 using 18-nucleotide 3'-fluorescein-labeled RNA annealed to a complementary 18-nucleotide 5'-dabsyl-labeled DNA as substrate measured after 1 hr2017European journal of medicinal chemistry, Apr-21, Volume: 130ISSN: 1768-3254Natural product-inspired esters and amides of ferulic and caffeic acid as dual inhibitors of HIV-1 reverse transcriptase.
AID1169294Inhibition of TTR V30M mutant (unknown origin) expressed in Escherichia coli assessed as inhibition of amyloid fibril formation at 20 uM by fluorescence assay2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
ISSN: 1520-4804		Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
AID1718341Growth inhibition of human KMM-1 cells at 10 uM after 48 hrs by PrestoBlue cell viability assay relative to control2020Journal of natural products, 12-24, Volume: 83, Issue:12
ISSN: 1520-6025		Antimyeloma Potential of Caffeic Acid Phenethyl Ester and Its Analogues through Sp1 Mediated Downregulation of IKZF1-IRF4-MYC Axis.
AID1446873Inhibition of wild-type HIV1 RT associated RNA dependent DNA polymerase activity using poly(A) template/oligo(dT) primer after 30 mins by picogreen staining based method2017European journal of medicinal chemistry, Apr-21, Volume: 130ISSN: 1768-3254Natural product-inspired esters and amides of ferulic and caffeic acid as dual inhibitors of HIV-1 reverse transcriptase.
AID1169301Inhibition of acid-mediated dissociation of TTR V30M mutant (unknown origin) expressed in Escherichia coli after 30 mins by SDS-PAGE2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
ISSN: 1520-4804		Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
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
ISSN: 0163-3864		Anti-influenza virus effect of some propolis constituents and their analogues (esters of substituted cinnamic acids).
AID1524671Covalent inhibition of purified Sporosarcinia pasteurii urease by phenol red based method2019Bioorganic & medicinal chemistry letters, 05-01, Volume: 29, Issue:9
ISSN: 1464-3405

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (40.00)18.2507
2000's2 (20.00)29.6817
2010's3 (30.00)24.3611
2020's1 (10.00)2.80

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%
Other10 (100.00%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
vanillin
1
benzaldehydes;
monomethoxybenzene;
phenols		anti-inflammatory agent;
anticonvulsant;
antioxidant;
flavouring agent;
plant metabolite		201720177.0low000010
diflunisal
1
monohydroxybenzoic acid;
organofluorine compound		non-narcotic analgesic;
non-steroidal anti-inflammatory drug		2014201410.0low000010
masoprocol
1
catechols;
lignan;
tetrol		antioxidant;
ferroptosis inhibitor;
geroprotector;
plant metabolite		2014201410.0low000010
oleanolic acid
1
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite201720177.0low000010
efavirenz
1
acetylenic compound;
benzoxazine;
cyclopropanes;
organochlorine compound;
organofluorine compound		antiviral drug;
HIV-1 reverse transcriptase inhibitor		201720177.0low000010
ursolic acid
1
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		geroprotector;
plant metabolite		201720177.0low000010
betulinic acid
1
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-HIV agent;
anti-inflammatory agent;
antimalarial;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
plant metabolite		201720177.0low000010
sesamin
1
benzodioxoles;
furofuran;
lignan		antineoplastic agent;
neuroprotective agent;
plant metabolite		2014201410.0low000010
matairesinol
1
gamma-lactone;
lignan;
polyphenol		angiogenesis inhibitor;
anti-asthmatic agent;
phytoestrogen;
plant metabolite		2014201410.0low000010
pomalidomide
1
aromatic amine;
dicarboximide;
isoindoles;
piperidones		angiogenesis inhibitor;
antineoplastic agent;
immunomodulator		202020204.0low000010
dihydroguaiaretic acid
1
2014201410.0low000010
lenalidomide
1
aromatic amine;
dicarboximide;
isoindoles;
piperidones		angiogenesis inhibitor;
antineoplastic agent;
immunomodulator		202020204.0low000010
pomolic acid
1
triterpenoidmetabolite201720177.0low000010
ferulic acid
1
ferulic acidsanti-inflammatory agent;
antioxidant;
apoptosis inhibitor;
cardioprotective agent;
MALDI matrix material;
plant metabolite		201720177.0low000010
isoliquiritigenin
1
chalconesantineoplastic agent;
biological pigment;
EC 1.14.18.1 (tyrosinase) inhibitor;
GABA modulator;
geroprotector;
metabolite;
NMDA receptor antagonist		2002200222.0low000100
caffeic acid
2
caffeic acidgeroprotector;
mouse metabolite		201420207.0low000020
methyl caffeate
3
alkyl caffeate ester;
methyl ester		1995201420.3low001110
ethyl ferulate
1
201720177.0low000010
capsaicin
1
capsaicinoidnon-narcotic analgesic;
TRPV1 agonist;
voltage-gated sodium channel blocker		2014201410.0low000010
cyqualon
1
2002200222.0low000100
chlorogenic acid
1
cinnamate ester;
tannin		food component;
plant metabolite		2014201410.0low000010
coniferaldehyde
1
cinnamaldehydes;
guaiacols;
phenylpropanoid		antifungal agent;
plant metabolite		201720177.0low000010
stigmasterol
1
3beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
phytosterols;
stigmastane sterol		plant metabolite201720177.0low000010
butein
1
chalcones;
polyphenol		antineoplastic agent;
antioxidant;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
geroprotector;
hypoglycemic agent;
plant metabolite;
radiosensitizing agent;
tyrosine kinase inhibitor		2002200222.0low000100
geranylgeraniol
1
geranylgeraniol201720177.0low000010
caffeic acid phenethyl ester
5
alkyl caffeate esteranti-inflammatory agent;
antibacterial agent;
antineoplastic agent;
antioxidant;
antiviral agent;
immunomodulator;
metabolite;
neuroprotective agent		1992202019.4low002120
1,1-dimethylallyl caffeic acid ester
1
hydroxycinnamic acid2014201410.0medium000010
rosmarinic acid
1
rosmarinic acidgeroprotector;
plant metabolite		2014201410.0low000010
oleyl alcohol
1
fatty alcohol 18:1;
long-chain primary fatty alcohol		metabolite;
nonionic surfactant		201720177.0low000010
bisdemethoxycurcumin
1
beta-diketone;
diarylheptanoid;
enone;
polyphenol		EC 3.2.1.1 (alpha-amylase) inhibitor;
metabolite		2002200222.0low000100
ethyl caffeate
3
alkyl caffeate ester;
ethyl ester;
hydroxycinnamic acid		anti-inflammatory agent;
antineoplastic agent;
metabolite		1995201420.3medium001110
ag 99
1
1995199529.0low001000
2-Phenylethyl 3-phenyl-2-propenoate
1
cinnamate ester2014201410.0medium000010
benzyl caffeate
4
1992201423.2high002110
hylin
1
2002200222.0low000100
octyl caffeate
1
2014201410.0medium000010
2,3-bis(3'-hydroxybenzyl)butyrolactone, (trans)-isomer
1
2014201410.0high000010
ks370g
1
202020204.0low000010
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
glycine
1
alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid		EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical		2008200816.0low000100
phenylethyl alcohol
1
benzenes;
primary alcohol		Aspergillus metabolite;
fragrance;
plant growth retardant;
plant metabolite;
Saccharomyces cerevisiae metabolite		2014201410.0low000010
1,3-xylenediamine
1
2008200816.0low000100
azoxymethane
2
1995199728.0low002000
masoprocol
1
nordihydroguaiaretic acidantineoplastic agent;
hypoglycemic agent;
lipoxygenase inhibitor;
metabolite		2014201410.0low000010
6-phenylhexyl isothiocyanate
1
1997199727.0low001000
curcumin
1
aromatic ether;
beta-diketone;
diarylheptanoid;
enone;
polyphenol		anti-inflammatory agent;
antifungal agent;
antineoplastic agent;
biological pigment;
contraceptive drug;
dye;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor;
EC 1.8.1.9 (thioredoxin reductase) inhibitor;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor;
EC 3.5.1.98 (histone deacetylase) inhibitor;
flavouring agent;
food colouring;
geroprotector;
hepatoprotective agent;
immunomodulator;
iron chelator;
ligand;
lipoxygenase inhibitor;
metabolite;
neuroprotective agent;
nutraceutical;
radical scavenger		1997199727.0low001000
sulindac
1
monocarboxylic acid;
organofluorine compound;
sulfoxide		analgesic;
antineoplastic agent;
antipyretic;
apoptosis inducer;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
prodrug;
tocolytic agent		1997199727.0low001000
caffeic acid phenethyl ester
1
alkyl caffeate esteranti-inflammatory agent;
antibacterial agent;
antineoplastic agent;
antioxidant;
antiviral agent;
immunomodulator;
metabolite;
neuroprotective agent		2014201410.0low000010
amyloid beta-peptides
1
2008200816.0low000100
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Adenocarcinoma0
1
1997199727.0low001000
Adenocarcinoma, Basal Cell0
1
1997199727.0low001000
Amyloid Neuropathies, Familial0
1
2014201410.0low000010
Amyloid Neuropathy Type 10
1
2014201410.0low000010
Amyloidosis0
1
2014201410.0low000010
Body Weight0
1
1995199529.0low001000
Cancer of Colon0
2
1995199728.0medium002000
Colonic Neoplasms0
2
1995199728.0medium002000
HIV0
1
1995199529.0low001000
Infections, Orthomyxoviridae0
1
1992199232.0low001000
Kahler Disease0
1
202020204.0low000010
Multiple Myeloma0
1
202020204.0low000010
Orthomyxoviridae Infections0
1
1992199232.0low001000

Long-term Use (1)

ArticleYear
Modulation of apoptosis by sulindac, curcumin, phenylethyl-3-methylcaffeate, and 6-phenylhexyl isothiocyanate: apoptotic index as a biomarker in colon cancer chemoprevention and promotion.
Cancer research, , Apr-01, Volume: 57, Issue:7		1997