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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (29)transporters (1) Show 30 proteins XML

enzymes (29)transporters (1) Show 30 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-07-07 20:54:00 UTC

HMDB ID

HMDB0000162

Secondary Accession Numbers

HMDB00162

Metabolite Identification

Common Name

Proline

Description

Proline (Pro), also known as L-proline is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. Proline is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Proline is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid. 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 synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. Proline is derived from the amino acid L-glutamate in which glutamate-5-semialdehyde is first formed by glutamate 5-kinase and glutamate-5-semialdehyde dehydrogenase (which requires NADH or NADPH). This semialdehyde can then either spontaneously cyclize to form 1-pyrroline-5-carboxylic acid, which is reduced to proline by pyrroline-5-carboxylate reductase, or turned into ornithine by ornithine aminotransferase, followed by cyclization by ornithine cyclodeaminase to form proline. L-Proline has been found to act as a weak agonist of the glycine receptor and of both NMDA and non-NMDA ionotropic glutamate receptors. It has been proposed to be a potential endogenous excitotoxin/neurotoxin. Studies in rats have shown that when injected into the brain, proline non-selectively destroys pyramidal and granule cells (PMID: 3409032 ). Therefore, under certain conditions proline can act as a neurotoxin and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of proline are associated with at least five inborn errors of metabolism, including hyperprolinemia type I, hyperprolinemia type II, iminoglycinuria, prolinemia type II, and pyruvate carboxylase deficiency. People with hyperprolinemia type I often do not show any symptoms even though they have proline levels in their blood between 3 and 10 times the normal level. Some individuals with hyperprolinemia type I exhibit seizures, intellectual disability, or other neurological or psychiatric problems. Hyperprolinemia type II results in proline levels in the blood between 10 and 15 times higher than normal, and high levels of a related compound called pyrroline-5-carboxylate. Hyperprolinemia type II has signs and symptoms that vary in severity and is more likely than type I to involve seizures or intellectual disability.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-(S)-Proline	ChEBI
(-)-2-Pyrrolidinecarboxylic acid	ChEBI
(-)-Proline	ChEBI
(2S)-Pyrrolidine-2-carboxylic acid	ChEBI
(S)-2-Carboxypyrrolidine	ChEBI
(S)-2-Pyrrolidinecarboxylic acid	ChEBI
(S)-Pyrrolidine-2-carboxylic acid	ChEBI
2-Pyrrolidinecarboxylic acid	ChEBI
L-(-)-Proline	ChEBI
L-alpha-Pyrrolidinecarboxylic acid	ChEBI
L-Prolin	ChEBI
L-Pyrrolidine-2-carboxylic acid	ChEBI
P	ChEBI
Prolina	ChEBI
PROLINE	ChEBI
Prolinum	ChEBI
(-)-2-Pyrrolidinecarboxylate	Generator
(2S)-Pyrrolidine-2-carboxylate	Generator
(S)-2-Pyrrolidinecarboxylate	Generator
(S)-Pyrrolidine-2-carboxylate	Generator
2-Pyrrolidinecarboxylate	Generator
L-a-Pyrrolidinecarboxylate	Generator
L-a-Pyrrolidinecarboxylic acid	Generator
L-alpha-Pyrrolidinecarboxylate	Generator
L-Α-pyrrolidinecarboxylate	Generator
L-Α-pyrrolidinecarboxylic acid	Generator
L-Pyrrolidine-2-carboxylate	Generator
(S)-(-)-Proline	HMDB
(S)-(-)-Pyrrolidine-2-carboxylate	HMDB
(S)-(-)-Pyrrolidine-2-carboxylic acid	HMDB
(S)-2-Pyrralidinecarboxylate	HMDB
(S)-2-Pyrralidinecarboxylic acid	HMDB
(S)-Proline	HMDB
L Proline	HMDB

Chemical Formula

C₅H₉NO₂

Average Molecular Weight

115.1305

Monoisotopic Molecular Weight

115.063328537

IUPAC Name

(2S)-pyrrolidine-2-carboxylic acid

Traditional Name

L-proline

CAS Registry Number

147-85-3

SMILES

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

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

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.

Showing metabocard for Proline (HMDB0000162)

MOL for HMDB0000162 (Proline)

3D MOL for HMDB0000162 (Proline)

3D SDF for HMDB0000162 (Proline)

3D-SDF for HMDB0000162 (Proline)

PDB for HMDB0000162 (Proline)

3D PDB for HMDB0000162 (Proline)

SMILES for HMDB0000162 (Proline)

INCHI for HMDB0000162 (Proline)

Structure for HMDB0000162 (Proline)

3D Structure for HMDB0000162 (Proline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra