FComEx: 4-Aminohippuric acid (PC000523)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:08 UTC

Update date

2017-01-19 02:36:26 UTC

FoodComEx ID

PC000523

FoodDB Record

FDB022720

Chemical Information

Name

4-Aminohippuric acid

Description

4-Aminohippuric acid 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 Renal proximal tubules secrete various organic anions, including drugs and p-aminohippurate (PAH). Uptake of PAH from blood into tubule cells occurs by exchange with intracellular alpha-ketoglutarate and is mediated by the organic anion transporter 1. PAH exit into tubule lumen is species specific and may involve ATP-independent and -dependent transporters. (PMID 11443229) Enhanced secretion of p-aminohippuric acid occurs in Fanconi's syndrome (FS). FS is associated with numerous varieties of inherited and acquired conditions; FS is characterized by a generalized transport defect in the proximal tubules, leading to renal losses of glucose, phosphate, calcium, uric acid, amino acids, bicarbonates, and other organic compounds. (PMID 12552490) [HMDB]

CAS Number

61-78-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4-Aminohippate	Generator
4-Aminohippic acid	Generator
4-Aminohippurate	hmdb
Aminohippate	Generator
Aminohippic acid	Generator
Aminohippurate	hmdb
Aminohippuric acid	hmdb
Chlorphentermine	hmdb
N-(4-Aminobenzoyl)glycine	hmdb
N-(p-Aminobenzoyl)aminoacetate	hmdb
N-(p-Aminobenzoyl)aminoacetic acid	hmdb
N-(p-Aminobenzoyl)glycine	hmdb
N-(para-aminobenzoyl)glycine	hmdb
Nefrotest	hmdb
P-Aminohippate	Generator
P-Aminohippic acid	Generator
p-Aminohippurate	hmdb
p-Aminohippuric acid	hmdb
PAH	hmdb
Paha	hmdb
Para-aminohippate	Generator
Para-aminohippic acid	Generator
para-Aminohippurate	hmdb
para-Aminohippuric acid	hmdb
Paraaminohippate	Generator
Paraaminohippic acid	Generator
paraaminohippuric acid	hmdb

Chemical Formula

C9H10N2O3

IUPAC name

2-[(4-aminophenyl)formamido]acetic acid

InChI Identifier

InChI=1S/C9H10N2O3/c10-7-3-1-6(2-4-7)9(14)11-5-8(12)13/h1-4H,5,10H2,(H,11,14)(H,12,13)

InChI Key

HSMNQINEKMPTIC-UHFFFAOYSA-N

Isomeric SMILES

NC1=CC=C(C=C1)C(=O)NCC(O)=O

Average Molecular Weight

194.1873

Monoisotopic Molecular Weight

194.069142196

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hippuric acids

Alternative Parents