CHEBI:30745 - phenylacetic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name phenylacetic acid
ChEBI ID CHEBI:30745
Definition A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:25977, CHEBI:44686, CHEBI:8085
Supplier Information eMolecules:495300, ZINC000000388462
Download Molfile XML SDF
more structures >>
Wikipedia License
Phenylacetic acid (conjugate base phenylacetate), also known by various synonyms, is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a strong honey-like odor. Endogenously, it is a catabolite of phenylalanine. As a commercial chemical, because it can be used in the illicit production of phenylacetone (used in the manufacture of substituted amphetamines), it is subject to controls in countries including the United States and China.
Read full article at Wikipedia
Formula C8H8O2
Net Charge 0
Average Mass 136.14792
Monoisotopic Mass 136.05243
InChI InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
InChIKey WLJVXDMOQOGPHL-UHFFFAOYSA-N
SMILES OC(=O)Cc1ccccc1
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Aspergillus niger (NCBI:txid5061) of strain var. Tieghem. See: Phytochemistry, 1988, 27(10), 3169-3173
Escherichia coli (NCBI:txid562) See: PubMed
Stachylidium (NCBI:txid796327) Marine derived fungus isolated from sponge Callyspongia sp. cf. C. flammea of strain 220 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): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
EC 6.4.1.1 (pyruvate carboxylase) inhibitor
An EC 6.4.1.* (carboxylase) inhibitor that interferes with the action of pyruvate carboxylase (EC 6.4.1.1).
toxin
Poisonous substance produced by a biological organism such as a microbe, animal or plant.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
plant growth retardant

allergen
A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
auxin
Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").
View more via ChEBI Ontology
ChEBI Ontology
Outgoing phenylacetic acid (CHEBI:30745) has functional parent acetic acid (CHEBI:15366)
phenylacetic acid (CHEBI:30745) has role Aspergillus metabolite (CHEBI:76956)
phenylacetic acid (CHEBI:30745) has role Escherichia coli metabolite (CHEBI:76971)
phenylacetic acid (CHEBI:30745) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
phenylacetic acid (CHEBI:30745) has role allergen (CHEBI:50904)
phenylacetic acid (CHEBI:30745) has role auxin (CHEBI:22676)
phenylacetic acid (CHEBI:30745) has role EC 6.4.1.1 (pyruvate carboxylase) inhibitor (CHEBI:90318)
phenylacetic acid (CHEBI:30745) has role human metabolite (CHEBI:77746)
phenylacetic acid (CHEBI:30745) has role plant growth retardant (CHEBI:35219)
phenylacetic acid (CHEBI:30745) has role plant metabolite (CHEBI:76924)
phenylacetic acid (CHEBI:30745) has role toxin (CHEBI:27026)
phenylacetic acid (CHEBI:30745) is a benzenes (CHEBI:22712)
phenylacetic acid (CHEBI:30745) is a monocarboxylic acid (CHEBI:25384)
phenylacetic acid (CHEBI:30745) is a phenylacetic acids (CHEBI:25978)
phenylacetic acid (CHEBI:30745) is conjugate acid of phenylacetate (CHEBI:18401)
Incoming α-sulfophenylacetic acid (CHEBI:225282) has functional parent phenylacetic acid (CHEBI:30745)
(2-nitrophenyl)acetic acid (CHEBI:187870) has functional parent phenylacetic acid (CHEBI:30745)
(3,4-dihydroxyphenyl)acetic acid (CHEBI:41941) has functional parent phenylacetic acid (CHEBI:30745)
(3,5-dihydroxyphenyl)acetic acid (CHEBI:131431) has functional parent phenylacetic acid (CHEBI:30745)
(3-bromo-4-hydroxy-5-nitrophenyl)acetyl azide (CHEBI:63481) has functional parent phenylacetic acid (CHEBI:30745)
(3S)-3,7-dimethyloct-7-en-1-yl phenylacetate (CHEBI:142274) has functional parent phenylacetic acid (CHEBI:30745)
(4-hydroxy-3-nitrophenyl)acetyl azide (CHEBI:58986) has functional parent phenylacetic acid (CHEBI:30745)
(4-nitrophenyl)acetic acid (CHEBI:40443) has functional parent phenylacetic acid (CHEBI:30745)
2-phenylacetamide (CHEBI:16562) has functional parent phenylacetic acid (CHEBI:30745)
5-[2-(2-oxoethoxy)ethoxy]-diclofenac (CHEBI:61752) has functional parent phenylacetic acid (CHEBI:30745)
N-ethylphenylacetamide (CHEBI:4737) has functional parent phenylacetic acid (CHEBI:30745)
antimycin A9 (CHEBI:65413) has functional parent phenylacetic acid (CHEBI:30745)
benzylpenilloaldehyde (CHEBI:60542) has functional parent phenylacetic acid (CHEBI:30745)
diclofenac (CHEBI:47381) has functional parent phenylacetic acid (CHEBI:30745)
gepinacin (CHEBI:82641) has functional parent phenylacetic acid (CHEBI:30745)
homogentisic acid (CHEBI:44747) has functional parent phenylacetic acid (CHEBI:30745)
hydratropic acid (CHEBI:48526) has functional parent phenylacetic acid (CHEBI:30745)
mandelamide (CHEBI:136824) has functional parent phenylacetic acid (CHEBI:30745)
methyl 3-cyano-2-phenylpropanoate (CHEBI:71185) has functional parent phenylacetic acid (CHEBI:30745)
phenylacetyl-CoA (CHEBI:15537) has functional parent phenylacetic acid (CHEBI:30745)
phenylacetate (CHEBI:18401) is conjugate base of phenylacetic acid (CHEBI:30745)
IUPAC Name
phenylacetic acid
Synonyms Sources
2-PHENYLACETIC ACID PDBeChem
2-Phenylethanoic acid HMDB
α-toluic acid NIST Chemistry WebBook
Benzeneacetic acid KEGG COMPOUND
benzeneacetic acid NIST Chemistry WebBook
Benzylformic acid KEGG COMPOUND
Omega-Phenylacetic acid HMDB
ω-phenylacetic acid HMDB
PA ChEBI
Phenylacetic acid KEGG COMPOUND
Manual Xrefs Databases
4624 DrugCentral
C00000750 KNApSAcK
C07086 KEGG COMPOUND
ECMDB04128 ECMDB
HMDB0000209 HMDB
PAC PDBeChem
PHENYLACETATE MetaCyc
Phenylacetic_acid Wikipedia
YMDB00891 YMDB
View more database links
Registry Numbers Types Sources
103-82-2 CAS Registry Number KEGG COMPOUND
103-82-2 CAS Registry Number NIST Chemistry WebBook
103-82-2 CAS Registry Number ChemIDplus
1099647 Reaxys Registry Number Reaxys
68976 Gmelin Registry Number Gmelin
Citations
Ariza A, Barrionuevo E, Mayorga C, Montañez MI, Perez-Inestrosa E, Ruiz-Sánchez A, Rodríguez-Guéant RM, Fernández TD, Guéant JL, Torres MJ, Blanca M (2014)
IgE to penicillins with different specificities can be identified by a multiepitope macromolecule: Bihaptenic penicillin structures and IgE specificities.
Journal of immunological methods 406, 43-50 [PubMed:24631718]
[show Abstract]
Abdulmalek E, Arumugam M, Mizan HN, Abdul Rahman MB, Basri M, Salleh AB (2014)
Chemoenzymatic epoxidation of alkenes and reusability study of the phenylacetic acid.
TheScientificWorldJournal 2014, 756418 [PubMed:24587751]
[show Abstract]
Scholze A, Jankowski V, Henning L, Haass W, Wittstock A, Suvd-Erdene S, Zidek W, Tepel M, Jankowski J (2007)
Phenylacetic acid and arterial vascular properties in patients with chronic kidney disease stage 5 on hemodialysis therapy.
Nephron. Clinical practice 107, c1-6 [PubMed:17622769]
[show Abstract]
Mangani G, Canestrari F, Berloni A, Maione M, Pagliarani S, Mangani F (2004)
Gas chromatographic--mass spectrometric determination of phenylacetic acid in human blood.
Annali di chimica 94, 715-719 [PubMed:15506622]
[show Abstract]
Kim Y, Cho JY, Kuk JH, Moon JH, Cho JI, Kim YC, Park KH (2004)
Identification and antimicrobial activity of phenylacetic acid produced by Bacillus licheniformis isolated from fermented soybean, Chungkook-Jang.
Current microbiology 48, 312-317 [PubMed:15057459]
[show Abstract]
Panoutsopoulos GI (2004)
Metabolism of 2-phenylethylamine to phenylacetic acid, via the intermediate phenylacetaldehyde, by freshly prepared and cryopreserved guinea pig liver slices.
In vivo (Athens, Greece) 18, 779-786 [PubMed:15646820]
[show Abstract]
Zhao Z, Baldo BA, Rimmer J (2002)
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 32, 1644-1650 [PubMed:12569987]
[show Abstract]
Liu YQ, Jetton TL, Leahy JL (2002)
beta-Cell adaptation to insulin resistance. Increased pyruvate carboxylase and malate-pyruvate shuttle activity in islets of nondiabetic Zucker fatty rats.
The Journal of biological chemistry 277, 39163-39168 [PubMed:12147706]
[show Abstract]
Moreno F, Blanca M, Mayorga C, Terrados S, Moya M, Pérez E, Suau R, Vega JM, García J, Miranda A (1995)
Studies of the specificities of IgE antibodies found in sera from subjects with allergic reactions to penicillins.
International archives of allergy and immunology 108, 74-81 [PubMed:7544181]
[show Abstract]
Mayorga C, Obispo T, Jimeno L, Blanca M, Moscoso del Prado J, Carreira J, Garcia JJ, Juarez C (1995)
Epitope mapping of beta-lactam antibiotics with the use of monoclonal antibodies.
Toxicology 97, 225-234 [PubMed:7716788]
[show Abstract]
Harle DG, Baldo BA (1990)
Drugs as allergens: an immunoassay for detecting IgE antibodies to cephalosporins.
International archives of allergy and applied immunology 92, 439-444 [PubMed:2083978]
[show Abstract]
Last Modified
28 April 2022