CHEBI:32374 - trans-4-coumaric acid

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ChEBI Name trans-4-coumaric acid
ChEBI ID CHEBI:32374
ChEBI ASCII Name trans-4-coumaric acid
Definition The trans-isomer of 4-coumaric acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43108, CHEBI:1812, CHEBI:15796, CHEBI:27061
Supplier Information ChemicalBook:CB5741946, eMolecules:474954, ZINC000012360703
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Formula C9H8O3
Net Charge 0
Average Mass 164.15802
Monoisotopic Mass 164.04734
InChI InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
InChIKey NGSWKAQJJWESNS-ZZXKWVIFSA-N
SMILES OC(=O)\C=C\c1ccc(O)cc1
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): food component
A physiological role played by any substance that is distributed in foodstuffs. It includes materials derived from plants or animals, such as vitamins or minerals, as well as environmental contaminants.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via 4-coumaric acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing trans-4-coumaric acid (CHEBI:32374) has role food component (CHEBI:78295)
trans-4-coumaric acid (CHEBI:32374) has role mouse metabolite (CHEBI:75771)
trans-4-coumaric acid (CHEBI:32374) has role plant metabolite (CHEBI:76924)
trans-4-coumaric acid (CHEBI:32374) is a 4-coumaric acid (CHEBI:36090)
trans-4-coumaric acid (CHEBI:32374) is conjugate acid of trans-4-coumarate (CHEBI:12876)
Incoming (2R,3S)-trans-coutaric acid (CHEBI:76095) has functional parent trans-4-coumaric acid (CHEBI:32374)
(E)-p-coumaroylagmatine (CHEBI:86080) has functional parent trans-4-coumaric acid (CHEBI:32374)
1-O-(4-coumaroyl)-β-D-glucose (CHEBI:71498) has functional parent trans-4-coumaric acid (CHEBI:32374)
3-β-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid (CHEBI:65663) has functional parent trans-4-coumaric acid (CHEBI:32374)
3-O-(trans-4-coumaroyl)-β-D-glucopyranose (CHEBI:76094) has functional parent trans-4-coumaric acid (CHEBI:32374)
3-O-trans-p-coumaroyl actinidic acid (CHEBI:65661) has functional parent trans-4-coumaric acid (CHEBI:32374)
4-acetoxycinnamic acid (CHEBI:86580) has functional parent trans-4-coumaric acid (CHEBI:32374)
6'-coumaroyl-1'-O-[2-(3,4-dihydroxyphenyl)ethyl]-β-D-glucopyranoside (CHEBI:65664) has functional parent trans-4-coumaric acid (CHEBI:32374)
6-O-(trans-4-coumaroyl)-α-D-glucopyranose (CHEBI:76092) has functional parent trans-4-coumaric acid (CHEBI:32374)
6-O-(trans-4-coumaroyl)-β-D-glucopyranose (CHEBI:76089) has functional parent trans-4-coumaric acid (CHEBI:32374)
N1,N5,N10-(E)-tri-p-coumaroylspermidine (CHEBI:232336) has functional parent trans-4-coumaric acid (CHEBI:32374)
N1,N8-bis(coumaroyl)spermidine (CHEBI:85530) has functional parent trans-4-coumaric acid (CHEBI:32374)
trans-4-coumaroyl-CoA (CHEBI:85531) has functional parent trans-4-coumaric acid (CHEBI:32374)
asprellic acid A (CHEBI:65455) has functional parent trans-4-coumaric acid (CHEBI:32374)
asprellic acid C (CHEBI:65456) has functional parent trans-4-coumaric acid (CHEBI:32374)
brevipolide A (CHEBI:65522) has functional parent trans-4-coumaric acid (CHEBI:32374)
coniferyl p-coumarate (CHEBI:86599) has functional parent trans-4-coumaric acid (CHEBI:32374)
cyanidin 3-O-(6-O-(E)-4-coumaroyl-β-D-glucoside) (CHEBI:29560) has functional parent trans-4-coumaric acid (CHEBI:32374)
cyanidin 3-O-{6-O-[6-O-(4-coumaroyl)-β-D-glucosyl]-2-O-β-D-xylosyl-β-D-galactoside} (CHEBI:71499) has functional parent trans-4-coumaric acid (CHEBI:32374)
delphinidin 3-O-(6-O-(E)-4-coumaroyl-β-D-glucoside) (CHEBI:75677) has functional parent trans-4-coumaric acid (CHEBI:32374)
isorhamnetin 3-O-α-L-[6''''-p-coumaroyl-β-D-glucopyranosyl-(1→2)-rhamnopyranoside] (CHEBI:66097) has functional parent trans-4-coumaric acid (CHEBI:32374)
kaempferol 3-O-α-L-[6'''-p-coumaroyl-β-D-glucopyranosyl-(1→2)-rhamnopyranoside] (CHEBI:66131) has functional parent trans-4-coumaric acid (CHEBI:32374)
kaempferol 3-O-α-L-[6'''-p-coumaroyl-β-D-glucopyranosyl-(1→2)-rhamnopyranoside]-7-O-β-D-glucopyranoside (CHEBI:66132) has functional parent trans-4-coumaric acid (CHEBI:32374)
kaempferol 3-O-[6-(4-coumaroyl)-β-D-glucosyl-(1→2)-β-D-glucosyl-(1→2)-β-D-glucoside] (CHEBI:31741) has functional parent trans-4-coumaric acid (CHEBI:32374)
kaempferol 7-O-(2,3-di-E-p-coumaroyl-α-L-rhamnopyranoside) (CHEBI:66133) has functional parent trans-4-coumaric acid (CHEBI:32374)
kaempferol 7-O-(2-E-p-coumaroyl-α-L-rhamnopyranoside) (CHEBI:66134) has functional parent trans-4-coumaric acid (CHEBI:32374)
leufolin A (CHEBI:66575) has functional parent trans-4-coumaric acid (CHEBI:32374)
leufolin B (CHEBI:66576) has functional parent trans-4-coumaric acid (CHEBI:32374)
luzonial A (CHEBI:66598) has functional parent trans-4-coumaric acid (CHEBI:32374)
malvidin 3-O-(6-O-(E)-4-coumaroyl-β-D-glucoside) (CHEBI:75693) has functional parent trans-4-coumaric acid (CHEBI:32374)
methyl 4-[(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl]coumarate (CHEBI:86586) has functional parent trans-4-coumaric acid (CHEBI:32374)
methyl p-coumarate acetate (CHEBI:86584) has functional parent trans-4-coumaric acid (CHEBI:32374)
myrciacitrin IV (CHEBI:66420) has functional parent trans-4-coumaric acid (CHEBI:32374)
myricetin 3-O-[(6-O-trans-4-coumaroyl-β-D-glucosyl)-(1→2)-α-L-rhamnoside] (CHEBI:145788) has functional parent trans-4-coumaric acid (CHEBI:32374)
pelargonidin 3-(6-p-coumaroyl)glucoside (CHEBI:80475) has functional parent trans-4-coumaric acid (CHEBI:32374)
peonidin 3-O-(6-O-(E)-4-coumaroyl-β-D-glucoside) (CHEBI:75707) has functional parent trans-4-coumaric acid (CHEBI:32374)
petunidin 3-O-(6-O-(E)-4-coumaroyl-β-D-glucoside) (CHEBI:75709) has functional parent trans-4-coumaric acid (CHEBI:32374)
quercetin 3-O-α-L-[6'''-p-coumaroyl-β-D-glucopyranosyl-(1→2)-rhamnopyranoside] (CHEBI:66285) has functional parent trans-4-coumaric acid (CHEBI:32374)
quercetin 3-O-α-L-[6'''-p-coumaroyl-β-D-glucopyranosyl-(1→2)-rhamnopyranoside]-7-O-β-D-glucopyranoside (CHEBI:66286) has functional parent trans-4-coumaric acid (CHEBI:32374)
tribuloside (CHEBI:80944) has functional parent trans-4-coumaric acid (CHEBI:32374)
trans-4-coumarate (CHEBI:12876) is conjugate base of trans-4-coumaric acid (CHEBI:32374)
IUPAC Name
(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
Note: (2004-07-26) The naturally occurring compound has (E) stereochemistry. Both (E) and (Z) isomers are available synthetically.
Synonyms Sources
(2E)-3-(4-hydroxyphenyl)acrylic acid ChEBI
(E)-3-(4-hydroxyphenyl)-2-propenoic acid ChemIDplus
(E)-p-coumaric acid NIST Chemistry WebBook
(E)-p-hydroxycinnamic acid ChemIDplus
4'-HYDROXYCINNAMIC ACID PDBeChem
4-Hydroxycinnamic acid KEGG COMPOUND
naringeninic acid NIST Chemistry WebBook
p-Coumaric acid KEGG COMPOUND
trans-4-hydroxycinnamic acid ChemIDplus
trans-p-coumaric acid NIST Chemistry WebBook
trans-p-coumarinic acid ChemIDplus
trans-p-Hydroxycinnamate KEGG COMPOUND
trans-p-hydroxycinnamic acid ChemIDplus
Manual Xrefs Databases
C00000152 KNApSAcK
C00000580 KNApSAcK
C00811 KEGG COMPOUND
HC4 PDBeChem
HMDB0002035 HMDB
P-Coumaric_acid Wikipedia
View more database links
Registry Numbers Types Sources
2207383 Reaxys Registry Number Reaxys
2245630 Gmelin Registry Number Gmelin
501-98-4 CAS Registry Number ChemIDplus
501-98-4 CAS Registry Number NIST Chemistry WebBook
7400-08-0 CAS Registry Number KEGG COMPOUND
Citations Types Sources
1057163 PubMed citation Europe PMC
12231735 PubMed citation Europe PMC
22511179 PubMed citation Europe PMC
Last Modified
22 October 2024