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
Supplier Information ChemicalBook:CB6275334, ChemicalBook:CB1111051, eMolecules:531533, ZINC000001532734
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Spermine is a polyamine involved in cellular metabolism that is found in all eukaryotic cells. The precursor for synthesis of spermine is the amino acid ornithine. It is an essential growth factor in some bacteria as well. It is found as a polycation at physiological pH. Spermine is associated with nucleic acids and is thought to stabilize helical structure, particularly in viruses. It functions as an intracellular free radical scavenger to protect DNA from free radical attack. Spermine is the chemical primarily responsible for the characteristic odor of semen. Antonie van Leeuwenhoek first described crystals of spermine phosphate in human semen in 1678. The name spermin was first used by the German chemists Ladenburg and Abel in 1888, and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling) and Germany (by Wrede et al.).
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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)
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-coumaric acid methyl ester (CHEBI:86904) 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)
N1,N5,N10-tri-p-coumaroyl spermidine (CHEBI:61514) 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)
Pestalotiopisorin A (CHEBI:207973) has functional parent 4-coumaric acid (CHEBI:36090)
spermidine hydroxycinnamic acid conjugate (CHEBI:61233) 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
Manual Xref Database
4-coumaric_acid Wikipedia
View more database links
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 Types Sources
11684179 PubMed citation Europe PMC
19089825 PubMed citation Europe PMC
19930809 PubMed citation Europe PMC
22447332 PubMed citation Europe PMC
22585412 PubMed citation Europe PMC
22923003 PubMed citation Europe PMC
23178520 PubMed citation Europe PMC
23420453 PubMed citation Europe PMC
23485470 PubMed citation Europe PMC
23669407 PubMed citation Europe PMC
23684599 PubMed citation Europe PMC
23810795 PubMed citation Europe PMC
23857900 PubMed citation Europe PMC
23892112 PubMed citation Europe PMC
24927550 PubMed citation Europe PMC
7285584 PubMed citation Europe PMC
Last Modified
24 June 2021
General Comment
2011-02-28 May be regarded as a deaminated derivative of phenylalanine.