FComEx: Pyrrole-2-carboxylic acid (PC000888)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:14 UTC

Update date

2017-01-19 02:36:40 UTC

FoodComEx ID

PC000888

FoodDB Record

FDB023340

Chemical Information

Name

Pyrrole-2-carboxylic acid

Description

Pyrrole-2-carboxylic acid was synthesized over a century ago, but its history as a compound of biological origin is rather recent. It was first identified as a degradation product of sialic acids, then as a derivative of the oxidation of the D-hydroxyproline isomers by mammalian D-amino acid oxidase. The latter relationship results from the lability of the direct oxidation product, A'-pyrroline-4-hydroxy-2-carboxylic acid, which loses water spontaneously to form the pyrrole. A similar reaction is catalyzed by the more specific allohydroxy-D-proline oxidase of Pseudomonas. In whole animal observations, pyrrole-2-carboxylate (PCA) ' was identified in rat or human urine after administration of the D-isomers of hydroxyproline, a finding ascribable to the action of D-amino acid oxidase. (PMID: 4430715) Urinary excretion of N-(pyrrole-2-carboxyl) glycine has been reported in a 5-year-old affected with type II hyperprolinemia; The child has mild developmental delay, recurrent seizures of the grand mal type and EEG alterations. The urinary excretion of the conjugate is stressed, since it appears that only one previous report in the literature described this compound in the urine of two patients affected by this disturbance. (PMID 2383933) [HMDB]

CAS Number

634-97-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1H-Pyrrole-2-carboxylic acid	hmdb
1H-Pyrrole-2-carboxylic acid (9CI)	hmdb
2-Minaline	hmdb
2-Pyrrolecarboxylate	Generator
2-Pyrrolecarboxylic acid	hmdb
Minalin	hmdb
Minaline	hmdb
PCA	hmdb
PYC	hmdb
Pyrrole-2-carboxylate	hmdb
Pyrrole-2-carboxylic acid	hmdb

Chemical Formula

C5H5NO2

IUPAC name

1H-pyrrole-2-carboxylic acid

InChI Identifier

InChI=1S/C5H5NO2/c7-5(8)4-2-1-3-6-4/h1-3,6H,(H,7,8)

InChI Key

WRHZVMBBRYBTKZ-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C1=CC=CN1

Average Molecular Weight

111.0987

Monoisotopic Molecular Weight

111.032028409

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrole 2-carboxylic acids. These are pyrrole carboxylic acids where the carboxyl group is attached at position C2.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroles

Sub Class

Pyrrole carboxylic acids and derivatives

Direct Parent

Pyrrole 2-carboxylic acids

Alternative Parents