Page last updated: 2024-11-05

methyl cinnamate

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

Description

methyl cinnamate: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

methyl cinnamate : A methyl ester resulting from the formal condensation of methyl cinnamic acid with methanol. It is found naturally in the essential oils of Alpinia and Basil leaf oil, and widely used in the flavor and perfume industries. [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]

methyl trans-cinnamate : The E (trans) isomer of methyl cinnamate. [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]

Cross-References

ID SourceID
PubMed CID637520
CHEMBL ID55060
CHEBI ID6857
CHEBI ID194138
SCHEMBL ID101530
MeSH IDM0084649

Synonyms (96)

Synonym
LS-13765
methyl 3-phenyl-2-propenoate
methyl 3-phenylacrylate
einecs 203-093-8
ai3-00579
methyl cinnamate (natural)
fema no. 2698
nsc-9411
wln: 1ov1u1r
methyl 3-phenylpropenoate
cinnamic acid, methyl ester
methyl cinnamylate
nsc9411
cinnamic acid methyl ester
2-propenoic acid, 3-phenyl-, methyl ester, (e)-
cinnamic acid, methyl ester, (e)-
103-26-4
C06358
3-phenyl-2-propenoic acid methyl
methyl cinnamate
methyl (e)-3-phenylprop-2-enoate
methyl (2e)-3-phenylacrylate
inchi=1/c10h10o2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8h,1h3/b8-7
1754-62-7
GHL.PD_MITSCHER_LEG0.369
methyl trans-cinnamate, >=98%, fcc, fg
methyl cinnamate, natural, >=98%, fcc, fg
methyl trans-cinnamate, 99%
methylcinnamate
methyl cinnamate, >=99.0% (gc)
trans-3-phenylacrylic acid methyl ester
methyl trans-3-phenylacrylate
chebi:6857 ,
CHEMBL55060
methyl 3-phenylprop-2-enoate
CHEBI:194138
methyl trans-cinnamate
(e)-methyl cinnamate
(e)-cinnamic acid methyl ester
(e)-3-phenylacrylic acid methyl ester
methyl (e)-3-phenylpropenoate
trans-methyl cinnamate
methyl (e)-cinnamate
methyl trans-3-phenyl-2-propenoate
trans-cinnamic acid methyl ester
trans-methyl 3-phenyl-2-propenoate
methyl (e)-3-phenyl-2-propenoate
methyl (2e)-3-phenylprop-2-enoate
NCGC00255910-01
dtxcid4022151
tox21_301384
cas-1754-62-7
dtxsid5044314 ,
methyl (2e)-3-phenylpropenoate
(e)-3-phenyl-2-propenoic acid methyl ester
(2e)-3-phenyl-2-propenoic acid methyl ester
trans-3-phenyl-2-propenoic acid methyl ester
unii-533cv2zcql
533cv2zcql ,
ec 203-093-8
semasorb 9815
AKOS015890136
S6221
methyl cinnamate, (e)-
cinnamic acid methyl ester [mi]
methyl cinnamate [fcc]
methyl cinnamate [fhfi]
SCHEMBL101530
methyl trans cinnamate
methyl-trans-cinnamate
methyl-3-phenylprop-2-enoate
NCGC00357235-01
dtxcid5028118
tox21_304025
cas-103-26-4
Q-100258
methyl (2e)-3-phenyl-2-propenoate #
2-propenoic acid, 3-phenyl-, methyl ester, (2e)-
mfcd00008458
J-522598
J-000917
methyl trans-cinnamate, analytical standard
methyl cinnamate, analytical reference material
Z19782655
J-011115
STL582416
DS-17838
Q204178
HY-W017212
CS-W017928
P16737
trans-3-phenyl-prop-2-enoic acid methyl ester
(e)-methyl ester 3-phenyl-2-propenoic acid
EN300-91678
methyl(e)-cinnamate
EN300-365971

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" To further investigate the effect of MC after the formation of neuropathic pain, MC at the dosage of 100 mg/kg was administrated on day 7-14 on CCI rats."( Methyl cinnamate alleviated CCI-induced upregualtion of spinal AMPA receptors and pain hypersensitivity by targeting AMPK.
Chen, L; Duan, S; Gui, Y; Li, A; Li, G; Tang, J, 2018
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
antibacterial agentA substance (or active part thereof) that kills or slows the growth of bacteria.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
fungal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
nematicideA substance used to destroy pests of the phylum Nematoda (roundworms).
[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 (1)

ClassDescription
methyl cinnamateA methyl ester resulting from the formal condensation of methyl cinnamic acid with methanol. It is found naturally in the essential oils of Alpinia and Basil leaf oil, and widely used in the flavor and perfume industries.
[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]

Pathways (1)

PathwayProteinsCompounds
volatile cinnamoic ester biosynthesis016
volatile cinnamoic ester biosynthesis216

Protein Targets (14)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LuciferasePhotinus pyralis (common eastern firefly)Potency64.63670.007215.758889.3584AID1224835
RAR-related orphan receptor gammaMus musculus (house mouse)Potency68.58960.006038.004119,952.5996AID1159521
GLI family zinc finger 3Homo sapiens (human)Potency25.58710.000714.592883.7951AID1259369; AID1259392
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency43.44880.001022.650876.6163AID1224838; AID1224839; AID1224893
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency30.88480.003041.611522,387.1992AID1159552; AID1159555
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency0.61130.001530.607315,848.9004AID1224841
farnesoid X nuclear receptorHomo sapiens (human)Potency0.17370.375827.485161.6524AID743217
estrogen nuclear receptor alphaHomo sapiens (human)Potency74.80630.000229.305416,493.5996AID1259244; AID1259248
thyroid stimulating hormone receptorHomo sapiens (human)Potency2.16900.001628.015177.1139AID1259385
Histone H2A.xCricetulus griseus (Chinese hamster)Potency126.79300.039147.5451146.8240AID1224845
Voltage-dependent calcium channel gamma-2 subunitMus musculus (house mouse)Potency76.95880.001557.789015,848.9004AID1259244
Glutamate receptor 2Rattus norvegicus (Norway rat)Potency76.95880.001551.739315,848.9004AID1259244
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Substance-P receptorCavia porcellus (domestic guinea pig)CD82.00000.90004.50009.8000AID144377
Quinone oxidoreductaseMus musculus (house mouse)CD82.00000.20002.74219.8000AID144377
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1191124Inhibition of Pseudomonas aeruginosa recombinant PqsD expressed in Escherichia coli BL21 (lambdaDE3) using ACoA/beta-ketodecanoic acid as substrate at 50 uM after 10 mins2015European journal of medicinal chemistry, Jan-27, Volume: 90Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD.
AID592088Antihemorrhagic activity in ddY mouse assessed as inhibition of Protobothrops flavoviridis venom-induced hemorrhage incubated with compound for 10 mins measured after 24 hrs2011Bioorganic & medicinal chemistry, Apr-01, Volume: 19, Issue:7
Contribution of cinnamic acid analogues in rosmarinic acid to inhibition of snake venom induced hemorrhage.
AID1191128Inhibition of Pseudomonas aeruginosa PA14 PqsH transposon mutant assessed as extracellular level of HHQ at 250 uM after 16 hrs2015European journal of medicinal chemistry, Jan-27, Volume: 90Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD.
AID1099186Antimicrobial activity against Athelia rolfsii assessed as growth inhibition at 100 ppm by agar dilution method1996Bioscience, biotechnology, and biochemistry, May, Volume: 60, Issue:5
Synthesis and antifungal activity of cinnamic acid esters.
AID1099189Antimicrobial activity against Pythium sp. assessed as growth inhibition at 100 ppm by agar dilution method1996Bioscience, biotechnology, and biochemistry, May, Volume: 60, Issue:5
Synthesis and antifungal activity of cinnamic acid esters.
AID1191126Binding affinity to Pseudomonas aeruginosa recombinant his6-tagged PqsD expressed in Escherichia coli BL21 (lambdaDE3) using AcoA as substrate at 250 to 500 uM incubated for 40 mins prior to compound addition followed by wash out for 30 mins by SPR analys2015European journal of medicinal chemistry, Jan-27, Volume: 90Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD.
AID174708Gastric cytoprotective activity in male wistar rat1997Journal of medicinal chemistry, Jun-06, Volume: 40, Issue:12
Structure-cytoprotective activity relationship of simple molecules containing an alpha,beta-unsaturated carbonyl system.
AID735814Antioxidant activity assessed as concentration required to 50 % ABTS radical scavenging activity absorbance at 734 nm2013Journal of natural products, Apr-26, Volume: 76, Issue:4
Dorsamin-A's, glycerolipids carrying a dehydrophenylalanine ester moiety from the seed-eating larvae of the bruchid beetle Bruchidius dorsalis.
AID144377Ability to induce NAD(P)H quinone reductase activity in cultured Hepa 1c1c7 murine hepatoma cells.1998Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26
Chemoprotective properties of phenylpropenoids, bis(benzylidene)cycloalkanones, and related Michael reaction acceptors: correlation of potencies as phase 2 enzyme inducers and radical scavengers.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (40)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (7.50)18.7374
1990's4 (10.00)18.2507
2000's6 (15.00)29.6817
2010's19 (47.50)24.3611
2020's8 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other39 (97.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]