FComEx: Pipecolic acid (PC000042)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:39 UTC

Update date

2017-01-19 02:36:11 UTC

FoodComEx ID

PC000042

FoodDB Record

FDB000545

Chemical Information

Name

Pipecolic acid

Description

Pipecolic acid is a metabolite of lysine found in human physiological fluids such as urine, plasma and CSF. However, it is uncertain if pipecolic acid originates directly from food intake or from mammalian or intestinal bacterial enzyme metabolism. Recent studies suggest that plasma pipecolic acid, particularly the D-isomer, originates mainly from the catabolism of dietary lysine by intestinal bacteria rather than by direct food intake. In classic Zellweger syndrome (a cerebro-hepato-renal genetic disorder, OMIM 214100) pipecolic acid accumulate in the plasma of the patients. It is known that plasma pipecolic acid levels are also elevated in patients with chronic liver diseases. Pipecolic acid is moderately elevated in patients with pyridoxine-dependent seizures and might therefore be a possible biochemical marker for selecting candidates for pyridoxine therapy (Plecko et al 2000). Pipecolic acid was also elevated in CSF in these vitamin B6-responsive patients. (PMID 12705501) [HMDB]. Pipecolic acid is a biomarker for the consumption of dried and cooked beans.

CAS Number

535-75-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
.alpha.-pipecolinic acid	HMDB
(.+/-.)-2-piperidinecarboxylic acid	HMDB
()-Piperidine-2-carboxylic acid	HMDB
(+/-)-2-piperidinecarboxylate	HMDB
(+/-)-2-piperidinecarboxylic acid	HMDB
(+/-)-pipecolate	HMDB
(+/-)-pipecolic acid	HMDB
(+/-)-pipecolinate	HMDB
(+/-)-pipecolinic acid	HMDB
(RS)-2-piperidinecarboxylate	HMDB
(RS)-2-piperidinecarboxylic acid	HMDB
2-Carboxypiperidine	HMDB
2-Pipecolinic acid	HMDB
2-Piperidinecarboxylate	Generator
2-Piperidinecarboxylic acid	ChEBI
2-Piperidinylcarboxylic acid	HMDB
a-Pipecolinate	HMDB
a-Pipecolinic acid	HMDB
Acide pipecolique	HMDB
Acide piperidine-carboxylique-2	HMDB
alpha-Pipecolinate	HMDB
alpha-Pipecolinic acid	HMDB
Dihydrobaikiane	HMDB
DL-2-Piperidinecarboxylate	HMDB
DL-2-Piperidinecarboxylic acid	HMDB
DL-Homoproline	HMDB
DL-Pipecolate	HMDB
DL-Pipecolic acid	HMDB
DL-Pipecolinate	HMDB
DL-Pipecolinic acid	HMDB
hexahydro-2-Picolinate	HMDB
hexahydro-2-Picolinic acid	HMDB
Hexahydropicolinate	HMDB
Hexahydropicolinic acid	db_source
Homoproline?	db_source
Pipecolate	HMDB
Pipecolic acid	db_source
Pipecolic acid free base	HMDB
Pipecolinate	Generator
Pipecolinic acid	db_source
Piperidine-2-carboxylic acid	HMDB
Piperolinate	HMDB
Piperolinic acid	HMDB

Chemical Formula

C6H11NO2

IUPAC name

piperidine-2-carboxylic acid

InChI Identifier

InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)

InChI Key

HXEACLLIILLPRG-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C1CCCCN1

Average Molecular Weight

129.157

Monoisotopic Molecular Weight

129.078978601

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents