CHEBI:36090 - 4-coumaric acid

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ChEBI Name 4-coumaric acid
ChEBI ID CHEBI:36090
Definition A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:20348, CHEBI:20405
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Formula C9H8O3
Net Charge 0
Average Mass 164.15802
Monoisotopic Mass 164.047
InChI InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)
InChIKey NGSWKAQJJWESNS-UHFFFAOYSA-N
SMILES [H]C(=Cc1ccc(O)cc1)C(O)=O
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): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing 4-coumaric acid (CHEBI:36090) has role plant metabolite (CHEBI:76924)
4-coumaric acid (CHEBI:36090) is a coumaric acid (CHEBI:23401)
4-coumaric acid (CHEBI:36090) is conjugate acid of 4-coumarate (CHEBI:32373)
Incoming 2-(p-coumaroyl)malic acid (CHEBI:134253) has functional parent 4-coumaric acid (CHEBI:36090)
3-(2-methoxyphenyl)-2-propenoic acid (CHEBI:93692) has functional parent 4-coumaric acid (CHEBI:36090)
3-p-coumaroylquinic acid (CHEBI:75499) has functional parent 4-coumaric acid (CHEBI:36090)
4-O-β-D-glucosyl-4-coumaric acid (CHEBI:17335) has functional parent 4-coumaric acid (CHEBI:36090)
4-p-coumaroylquinic acid (CHEBI:1945) has functional parent 4-coumaric acid (CHEBI:36090)
4-coumaroyl-CoA (CHEBI:15499) has functional parent 4-coumaric acid (CHEBI:36090)
5-p-coumaroylquinic acid (CHEBI:75500) has functional parent 4-coumaric acid (CHEBI:36090)
7-O-(6-p-coumaroylglucosyl)chrysoeriol (CHEBI:75509) has functional parent 4-coumaric acid (CHEBI:36090)
p-coumaroylagmatine (CHEBI:32818) has functional parent 4-coumaric acid (CHEBI:36090)
p-coutaric acid (CHEBI:77439) has functional parent 4-coumaric acid (CHEBI:36090)
bisdemethoxycurcumin (CHEBI:71045) has functional parent 4-coumaric acid (CHEBI:36090)
cadabicine sulfate (CHEBI:132716) has functional parent 4-coumaric acid (CHEBI:36090)
spermidine hydroxycinnamic acid conjugate (CHEBI:61233) has functional parent 4-coumaric acid (CHEBI:36090)
tricoumaroyl spermidine (CHEBI:61514) has functional parent 4-coumaric acid (CHEBI:36090)
cis-4-coumaric acid (CHEBI:17450) is a 4-coumaric acid (CHEBI:36090)
trans-4-coumaric acid (CHEBI:32374) is a 4-coumaric acid (CHEBI:36090)
4-coumarate (CHEBI:32373) is conjugate base of 4-coumaric acid (CHEBI:36090)
IUPAC Name
3-(4-hydroxyphenyl)prop-2-enoic acid
Synonyms Sources
3-(4-hydroxyphenyl)-2-propenoic acid ChemIDplus
3-(4-hydroxyphenyl)acrylic acid ChEBI
4'-hydroxycinnamic acid NIST Chemistry WebBook
4-coumaric acid ChemIDplus
4-hydroxycinnamic acid ChemIDplus
β-[4-hydroxyphenyl]acrylic acid NIST Chemistry WebBook
p-coumaric acid ChemIDplus
p-hydroxycinnamic acid ChemIDplus
p-hydroxyphenylacrylic acid ChemIDplus
para-coumaric acid NIST Chemistry WebBook
Database Link Database
4-coumaric_acid Wikipedia
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Registry Numbers Types Sources
2207381 Beilstein Registry Number Beilstein
7400-08-0 CAS Registry Number NIST Chemistry WebBook
7400-08-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11684179 PubMed citation Europe PMC
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Last Modified
23 June 2017
General Comment
2011-02-28 May be regarded as a deaminated derivative of phenylalanine.