FComEx: Phenylacetylglycine (PC000576)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:20 UTC

Update date

2017-01-19 02:36:28 UTC

FoodComEx ID

PC000576

FoodDB Record

FDB022266

Chemical Information

Name

Phenylacetylglycine

Description

Phenylacetylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine Phenylacetylglycine or PAG is a glycine conjugate of phenylacetic acid. Phenylacetic acid may arise from exposure to styrene (plastic) or through the consumption of fruits and vegetables. Phenylacetic acid is used in some perfumes, possessing a honey-like odour in low concentrations, and is also used in penicillin G production. PAG is a putative biomarker of phospholipidosis. Urinary PAG is elevated in animals exhibiting abnormal phospholipid accumulation in many tissues and may thus be useful as a surrogate biomarker for phospholipidosis. (PMID: 15764292) [HMDB]

CAS Number

500-98-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
((phenylacetyl)amino)acetic acid	hmdb
[(Phenylacetyl)amino]acetate	hmdb
[(Phenylacetyl)amino]acetic acid	hmdb
N-(phenylacetyl)-Glycine	hmdb
N-(Phenylacetyl)glycine	hmdb
N-Phenacetylglycine	hmdb
N-Phenylacetylglycine	hmdb
PAA	hmdb
PAG	hmdb
Phenacetate	Generator
Phenacetic acid	Generator
Phenaceturate	hmdb
Phenaceturic acid	hmdb
Phenacetylglycine	hmdb
phenylacetyl glycine	hmdb

Chemical Formula

C10H11NO3

IUPAC name

2-(2-phenylacetamido)acetic acid

InChI Identifier

InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)

InChI Key

UTYVDVLMYQPLQB-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CNC(=O)CC1=CC=CC=C1

Average Molecular Weight

193.1992

Monoisotopic Molecular Weight

193.073893223

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents