FComEx: L-Proline (PC000081)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:03 UTC

Update date

2017-01-19 02:36:12 UTC

FoodComEx ID

PC000081

FoodDB Record

FDB000570

Chemical Information

Name

L-Proline

Description

Proline or L-proline abbreviated Pro or is one of the twenty amino acids used in living organisms as the building blocks of proteins. Proline is sometimes called an imino acid, although the IUPAC definition of an imine requires a carbon-nitrogen double bond. Proline is a non-essential amino acid that is largely synthesized from glutamic acid. While proline biosynthetic pathways exist from eubacteria to eukaryotes, in the most prevalent pathway, proline is cyclized from glutamate. First glutamate is phosphorylated to gamma-glutamyl phosphate by gamma-glutamyl kinase, then second, reduced to gamma-glutamyl semialdehyde by gamma-glutamyl phosphate reductase, then third, cyclized spontaneously to delta(1)-pyrroline-5-carboxylate and fourth, reduced to proline by delta(1)-pyrroline-5-carboxylate reductase. In higher plants and animals, the first two steps are catalysed by a bi-functional delta(1) -pyrroline-5-carboxylate synthase. Alternative pathways of proline formation use the initial steps of the arginine biosynthetic pathway to ornithine, which can be converted to delta(1)-pyrroline-5-carboxylate by ornithine aminotransferase and then reduced to proline or converted directly to proline by ornithine cyclodeaminase (PMID: 25367752). Proline is an essential component of collagen and is important for proper functioning of joints and tendons. It is a potential endogenous excitotoxin/neurotoxin, which causes damage to nerve cells and nerve tissues. Proline, when injected into the brains of rats, non-selectively destroyed pyramidal and granule cells (PMID: 3409032) suggesting that it can act as a neurotoxin. Proline can also be a metabotoxin which is an endogenously produced metabolite that causes adverse health effects at chronically high levels. At least five inborn errors of metabolism, including hyperprolinemia type I, hyperprolinemia type II, iminoglycinuria, prolinemia type II, and pyruvate carboxylase deficiency are associated with chronically high levels of proline (PMID: 18806117). Hyperprolinemia I and II are caused by deficiencies in the enzymatic activities of proline dehydrogenase and Delta-1-pyrroline-5-carboxylate reductase, respectively.

CAS Number

147-85-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(-)-(S)-Proline	biospider
(-)-2-Pyrrolidinecarboxylate	biospider
(-)-2-Pyrrolidinecarboxylic acid	biospider
(-)-Proline	biospider
(2S)-Pyrrolidine-2-carboxylate	Generator
(2S)-Pyrrolidine-2-carboxylic acid	biospider
(L)-Proline	biospider
(S)-(-)-Proline	biospider
(S)-(-)-Pyrrolidine-2-carboxylate	biospider
(S)-(-)-Pyrrolidine-2-carboxylic acid	biospider
(S)-2-Carboxypyrrolidine	biospider
(S)-2-Pyrralidinecarboxylate	biospider
(S)-2-Pyrralidinecarboxylic acid	biospider
(S)-2-Pyrrolidinecarboxylate	biospider
(S)-2-Pyrrolidinecarboxylic acid	biospider
(S)-Proline	biospider
(S)-Pyrrolidine-2-carboxylate	Generator
(S)-Pyrrolidine-2-carboxylic acid	biospider
2-Pyrralidinecarboxylic acid, (S)-	biospider
2-Pyrrolidinecarboxylate	Generator
2-Pyrrolidinecarboxylic acid	ChEBI
2-Pyrrolidinecarboxylic acid, (S)-	biospider
FEMA 3319	db_source
L-(-)-Proline	biospider
L-a-Pyrrolidinecarboxylate	Generator
L-a-Pyrrolidinecarboxylic acid	Generator
L-alpha-Pyrrolidinecarboxylate	Generator
L-alpha-Pyrrolidinecarboxylic acid	biospider
L-Prolin	ChEBI
L-Proline	biospider
L-Pyrrolidine-2-carboxylate	Generator
L-Pyrrolidine-2-carboxylic acid	ChEBI
L-α-pyrrolidinecarboxylate	Generator
L-α-pyrrolidinecarboxylic acid	Generator
P	ChEBI
Prolina	ChEBI
PROLINE	ChEBI
Proline, 9CI; L-form	db_source
Prolinum	ChEBI

Chemical Formula

C5H9NO2

IUPAC name

(2S)-pyrrolidine-2-carboxylic acid

InChI Identifier

InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1

InChI Key

ONIBWKKTOPOVIA-BYPYZUCNSA-N

Isomeric SMILES

OC(=O)[C@@H]1CCCN1

Average Molecular Weight

115.1305

Monoisotopic Molecular Weight

115.063328537

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents