CHEBI:27386 - cinnamic acid

ChEBI IDCHEBI:27386
ChEBI Namecinnamic acid
Stars
DefinitionA monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.
Secondary ChEBI IDsCHEBI:3710, CHEBI:23250
Last Modified17 November 2016
DownloadsMolfile
FormulaC9H8O2
Net Charge0
Average Mass148.161
Monoisotopic Mass148.05243
SMILES[H]C(=Cc1ccccc1)C(=O)O
InChIInChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)
InChIKeyWBYWAXJHAXSJNI-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Cinnamomum aromaticum (ncbitaxon:119260) - PubMed (24868863)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
cinnamic acid (CHEBI:27386) has role plant metabolite (CHEBI:76924)
cinnamic acid (CHEBI:27386) is a cinnamic acids (CHEBI:23252)
cinnamic acid (CHEBI:27386) is a styrenes (CHEBI:26799)
cinnamic acid (CHEBI:27386) is conjugate acid of cinnamate (CHEBI:23248)
Incoming Relation(s)
(3E)-4-[3-(2-hydroxyethyl)-1H-indol-5-yl]but-3-en-2-one (CHEBI:210830) has functional parent cinnamic acid (CHEBI:27386)
(E)-1-Cinnamoylpyrrolidine (CHEBI:187055) has functional parent cinnamic acid (CHEBI:27386)
(E)-Herclavine (CHEBI:174123) has functional parent cinnamic acid (CHEBI:27386)
(E)-N-Cinnamoylpiperidine (CHEBI:157738) has functional parent cinnamic acid (CHEBI:27386)
1-(1-benzimidazolyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one (CHEBI:92061) has functional parent cinnamic acid (CHEBI:27386)
1-(2,4-dichlorophenyl)-5-(dimethylamino)-3-penta-1,4-dienone (CHEBI:115743) has functional parent cinnamic acid (CHEBI:27386)
1-(3-furanyl)-3-(4-methoxyphenyl)-2-propen-1-one (CHEBI:108249) has functional parent cinnamic acid (CHEBI:27386)
1-(3,4-dihydro-1H-isoquinolin-2-yl)-3-(4-methylphenyl)-2-propen-1-one (CHEBI:105723) has functional parent cinnamic acid (CHEBI:27386)
1-[(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoyl]piperidin-2-one (CHEBI:182908) has functional parent cinnamic acid (CHEBI:27386)
1-[1-oxo-3-(3,4,5-trimethoxyphenyl)prop-2-enyl]-2,3-dihydropyridin-6-one (CHEBI:92424) has functional parent cinnamic acid (CHEBI:27386)
1-[4-(3,4-dihydroxyphenyl)-6-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl]ethanone (CHEBI:112169) has functional parent cinnamic acid (CHEBI:27386)
1-Cinnamoylpyrrolidine (CHEBI:157709) has functional parent cinnamic acid (CHEBI:27386)
2-(1H-benzimidazol-2-yl)-3-(3-chloro-5-ethoxy-4-methoxyphenyl)-1-(4-morpholinyl)-2-propen-1-one (CHEBI:108116) has functional parent cinnamic acid (CHEBI:27386)
2,3-dihydroxycinnamic acid (CHEBI:48681) has functional parent cinnamic acid (CHEBI:27386)
3-(1,3-benzodioxol-5-yl)-1-(5-methyl-2-furanyl)-2-propen-1-one (CHEBI:116178) has functional parent cinnamic acid (CHEBI:27386)
3-(2-chlorophenyl)-1-(1H-pyrrol-2-yl)-2-propen-1-one (CHEBI:115516) has functional parent cinnamic acid (CHEBI:27386)
3-(2-chlorophenyl)-N-[[[(5-methyl-1H-pyrazol-3-yl)-oxomethyl]hydrazo]-sulfanylidenemethyl]-2-propenamide (CHEBI:113185) has functional parent cinnamic acid (CHEBI:27386)
3-(2,5-dimethoxyphenyl)-N-methyl-N-[2-(4-methylanilino)-2-oxoethyl]-2-propenamide (CHEBI:117129) has functional parent cinnamic acid (CHEBI:27386)
3-(3-bromo-4-methoxyphenyl)-N,N-di(propan-2-yl)-2-propenamide (CHEBI:123153) has functional parent cinnamic acid (CHEBI:27386)
3-(3,4-dichlorophenyl)-N-(4,5-dihydrothiazol-2-yl)-2-propenamide (CHEBI:95276) has functional parent cinnamic acid (CHEBI:27386)
3-(3,4-dimethoxyphenyl)-N-[[(1-oxo-2-thiophen-2-ylethyl)hydrazo]-sulfanylidenemethyl]-2-propenamide (CHEBI:120058) has functional parent cinnamic acid (CHEBI:27386)
3-(4-bromophenyl)-1-(2-methyl-5,6,7,8-tetrahydroquinolin-3-yl)-2-propen-1-one (CHEBI:115658) has functional parent cinnamic acid (CHEBI:27386)
3-(4-fluorophenyl)-N-[[[oxo(2-pyrazinyl)methyl]hydrazo]-sulfanylidenemethyl]-2-propenamide (CHEBI:107259) has functional parent cinnamic acid (CHEBI:27386)
3-(4-methoxyphenyl)-N-[[[oxo(thiophen-2-yl)methyl]hydrazo]-sulfanylidenemethyl]-2-propenamide (CHEBI:109605) has functional parent cinnamic acid (CHEBI:27386)
3-(4-tert-butylphenyl)-N-(4,5-dihydrothiazol-2-yl)-2-propenamide (CHEBI:112368) has functional parent cinnamic acid (CHEBI:27386)
3-[1-[(2,4-dichlorophenyl)methyl]-5-fluoro-3-methyl-7-indolyl]-N-[(4,5-dichloro-2-thiophenyl)sulfonyl]-2-propenamide (CHEBI:95012) has functional parent cinnamic acid (CHEBI:27386)
4-(1-naphthalenyl)-2-oxo-3-(2-quinolinyl)-3-butenoic acid (CHEBI:122033) has functional parent cinnamic acid (CHEBI:27386)
4-(3-chlorophenyl)-2-oxo-3-(2-quinolinyl)-3-butenoic acid (CHEBI:108030) has functional parent cinnamic acid (CHEBI:27386)
4-(3-Hydroxy-2-naphthyl)-2-oxobut-3-enoic acid (CHEBI:80381) has functional parent cinnamic acid (CHEBI:27386)
4-methoxycinnamic acid (CHEBI:48541) has functional parent cinnamic acid (CHEBI:27386)
4-oxo-3-(phenylmethylene)pentanoic acid (CHEBI:109554) has functional parent cinnamic acid (CHEBI:27386)
4,6-dimethyl-3-[1-oxo-3-(4-propan-2-ylphenyl)prop-2-enyl]-1H-pyridin-2-one (CHEBI:116930) has functional parent cinnamic acid (CHEBI:27386)
4,6-dimethyl-3-[3-(1-naphthalenyl)-1-oxoprop-2-enyl]-1H-pyridin-2-one (CHEBI:120966) has functional parent cinnamic acid (CHEBI:27386)
5-[3-(2-chlorophenyl)-1-oxoprop-2-enyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester (CHEBI:113036) has functional parent cinnamic acid (CHEBI:27386)
5-[3-(2-fluorophenyl)-1-oxoprop-2-enyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester (CHEBI:109377) has functional parent cinnamic acid (CHEBI:27386)
5-[3-(3-chlorophenyl)-1-oxoprop-2-enyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester (CHEBI:108020) has functional parent cinnamic acid (CHEBI:27386)
6,6,6-trifluoro-5-hydroxy-1,5-diphenyl-1-hexen-3-one (CHEBI:113014) has functional parent cinnamic acid (CHEBI:27386)
acetic acid [2-[2-(1-oxo-3-phenylprop-2-enyl)-3-phenyl-3,4-dihydropyrazol-5-yl]phenyl] ester (CHEBI:105087) has functional parent cinnamic acid (CHEBI:27386)
alkyl cinnamate (CHEBI:17958) has functional parent cinnamic acid (CHEBI:27386)
cadiolide B (CHEBI:188604) has functional parent cinnamic acid (CHEBI:27386)
cinepazide (CHEBI:135676) has functional parent cinnamic acid (CHEBI:27386)
Desmosdumotin C (CHEBI:185120) has functional parent cinnamic acid (CHEBI:27386)
ethyl p-methoxycinnamate (CHEBI:29015) has functional parent cinnamic acid (CHEBI:27386)
feruloylacetic acid (CHEBI:71303) has functional parent cinnamic acid (CHEBI:27386)
Hancockiamide A (CHEBI:221683) has functional parent cinnamic acid (CHEBI:27386)
Hancockiamide B (CHEBI:221688) has functional parent cinnamic acid (CHEBI:27386)
Hancockiamide C (CHEBI:221693) has functional parent cinnamic acid (CHEBI:27386)
Hancockiamide E (CHEBI:221702) has functional parent cinnamic acid (CHEBI:27386)
Hancockiamide G (CHEBI:221712) has functional parent cinnamic acid (CHEBI:27386)
Hancockiamide I (CHEBI:221721) has functional parent cinnamic acid (CHEBI:27386)
Lahorenoic acid A (CHEBI:200439) has functional parent cinnamic acid (CHEBI:27386)
Lahorenoic acid B (CHEBI:227177) has functional parent cinnamic acid (CHEBI:27386)
Linderone (CHEBI:178327) has functional parent cinnamic acid (CHEBI:27386)
LSM-24504 (CHEBI:113094) has functional parent cinnamic acid (CHEBI:27386)
LSM-31444 (CHEBI:120001) has functional parent cinnamic acid (CHEBI:27386)
LSM-36615 (CHEBI:125150) has functional parent cinnamic acid (CHEBI:27386)
LSM-36617 (CHEBI:125152) has functional parent cinnamic acid (CHEBI:27386)
LSM-36623 (CHEBI:125158) has functional parent cinnamic acid (CHEBI:27386)
LSM-4526 (CHEBI:93945) has functional parent cinnamic acid (CHEBI:27386)
LSM-4818 (CHEBI:94198) has functional parent cinnamic acid (CHEBI:27386)
LSM-4819 (CHEBI:94199) has functional parent cinnamic acid (CHEBI:27386)
LSM-4820 (CHEBI:94200) has functional parent cinnamic acid (CHEBI:27386)
LSM-4821 (CHEBI:94201) has functional parent cinnamic acid (CHEBI:27386)
LSM-4925 (CHEBI:94296) has functional parent cinnamic acid (CHEBI:27386)
LSM-6206 (CHEBI:94982) has functional parent cinnamic acid (CHEBI:27386)
LSM-6645 (CHEBI:95297) has functional parent cinnamic acid (CHEBI:27386)
LSM-6681 (CHEBI:95325) has functional parent cinnamic acid (CHEBI:27386)
Lucidone (CHEBI:183569) has functional parent cinnamic acid (CHEBI:27386)
methyl 4-hydroxy-2-oxo-4-phenyl-3-butenoate (CHEBI:137095) has functional parent cinnamic acid (CHEBI:27386)
N-(1-cinnamoylpyrrolidin-2-yl)cinnamamide (CHEBI:217917) has functional parent cinnamic acid (CHEBI:27386)
N-(2-methoxyethyl)-3-phenyl-N-[5-(3-pyridinyl)-1,3,4-thiadiazol-2-yl]-2-propenamide (CHEBI:115530) has functional parent cinnamic acid (CHEBI:27386)
N-(4,5-dihydrothiazol-2-yl)-3-(2,4-dimethoxyphenyl)-2-propenamide (CHEBI:125330) has functional parent cinnamic acid (CHEBI:27386)
N-(4,5-dihydrothiazol-2-yl)-3-(4-methylphenyl)-2-propenamide (CHEBI:95301) has functional parent cinnamic acid (CHEBI:27386)
N-(4,5-dihydrothiazol-2-yl)-3-(4-propan-2-ylphenyl)-2-propenamide (CHEBI:95278) has functional parent cinnamic acid (CHEBI:27386)
N-[[(1-oxo-2-thiophen-2-ylethyl)hydrazo]-sulfanylidenemethyl]-3-phenyl-2-propenamide (CHEBI:111379) has functional parent cinnamic acid (CHEBI:27386)
N-[[(4-methyl-2-pyridinyl)amino]-sulfanylidenemethyl]-3-phenyl-2-propenamide (CHEBI:121419) has functional parent cinnamic acid (CHEBI:27386)
N-[[[2-furanyl(oxo)methyl]hydrazo]-sulfanylidenemethyl]-3-(4-methoxyphenyl)-2-propenamide (CHEBI:114312) has functional parent cinnamic acid (CHEBI:27386)
N-[6-acetamido-3-(2-ethoxyethyl)-1,3-benzothiazol-2-ylidene]-3-(2-chlorophenyl)-2-propenamide (CHEBI:114912) has functional parent cinnamic acid (CHEBI:27386)
N-cyclohexyl-3-(3,4-dimethoxyphenyl)-N-(2-pyridinyl)-2-propenamide (CHEBI:116516) has functional parent cinnamic acid (CHEBI:27386)
N-cyclohexyl-3-(4-nitrophenyl)-N-(2-pyridinyl)-2-propenamide (CHEBI:107459) has functional parent cinnamic acid (CHEBI:27386)
N-hydroxy-3-[3-(phenylsulfamoyl)phenyl]-2-propenamide (CHEBI:94531) has functional parent cinnamic acid (CHEBI:27386)
N-methyl-3-(2-nitrophenyl)-N-(thiophen-2-ylmethyl)-2-propenamide (CHEBI:120404) has functional parent cinnamic acid (CHEBI:27386)
N-trans-cinnamoyl 2-amino-3a,4,5,6,7,8,9,10,11,12,13,13a-dodecahydrocyclododeca[d]oxazole (CHEBI:197880) has functional parent cinnamic acid (CHEBI:27386)
Swerilactone O (CHEBI:69299) has functional parent cinnamic acid (CHEBI:27386)
Syzygiol (CHEBI:137879) has functional parent cinnamic acid (CHEBI:27386)
Xenocockiamide B (CHEBI:221731) has functional parent cinnamic acid (CHEBI:27386)
Xenocockiamide C (CHEBI:221735) has functional parent cinnamic acid (CHEBI:27386)
Xenocockiamide D (CHEBI:221741) has functional parent cinnamic acid (CHEBI:27386)
cis-cinnamic acid (CHEBI:35699) is a cinnamic acid (CHEBI:27386)
trans-cinnamic acid (CHEBI:35697) is a cinnamic acid (CHEBI:27386)
cinnamate (CHEBI:23248) is conjugate base of cinnamic acid (CHEBI:27386)
IUPAC Name 
3-phenylprop-2-enoic acid
Synonyms  Source
Cinnamic acidKEGG COMPOUND
ZimtsäureChEBI
3-phenyl-2-propenoic acidNIST Chemistry WebBook
3-phenylacrylic acidNIST Chemistry WebBook
β-phenylacrylic acidNIST Chemistry WebBook
phenylacrylic acidNIST Chemistry WebBook
Manual XrefsDatabases
C10438KEGG COMPOUND
HMDB0000567HMDB
Cinnamic_acidWikipedia
Registry NumbersSources
Gmelin:328659Gmelin
Reaxys:507757Reaxys
CAS:621-82-9KEGG COMPOUND
CAS:621-82-9ChemIDplus
CAS:621-82-9NIST Chemistry WebBook
Citations