FComEx: Ornithine (PC000009)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:17 UTC

Update date

2017-01-19 02:36:09 UTC

FoodComEx ID

PC000009

FoodDB Record

FDB003654

Chemical Information

Name

Ornithine

Description

A non-essential and nonprotein amino acid, ornithine is critical for the production of the body's proteins, enzymes and muscle tissue. Ornithine plays a central role in the urea cycle and is important for the disposal of excess nitrogen (ammonia). Ornithine is the starting point for the synthesis of many polyamines such as putrescine and spermine. Ornithine supplements are claimed to enhance the release of growth hormone and to burn excess body fat. Ornithine is necessary for proper immune function and good liver function.; AF112968; L-Ornithine is one of the products of the action of the enzyme arginase on L-arginine, creating urea. Therefore, ornithine is a central part of the urea cycle, which allows for the disposal of excess nitrogen. Ornithine is recycled and in a manner is a catalyst. First, ammonia is converted into carbamoyl phosphate (phosphate-CONH2), which creates one half of urea. Ornithine is converted into a urea derivative at the ? (terminal) nitrogen by carbamoyl phosphate. Another nitrogen is added from aspartate, producing the denitrogenated fumarate, and the resulting arginine (a guanidinium compound) is hydrolysed back to ornithine, producing urea. The nitrogens of urea come from the ammonia and aspartate, and the nitrogen in ornithine remains intact.; ORNT1). Mutations in the mitochondrial ornithine transporter result in hyperammonemia, hyperornithinemia, homocitrullinuria (HHH) syndrome, a disorder of the urea cycle. (PMID 16256388) The pathophysiology of the disease may involve diminished ornithine transport into mitochondria, resulting in ornithine accumulation in the cytoplasm and reduced ability to clear carbamoyl phosphate and ammonia loads. (OMIM 838970); Ornithine is an amino acid produced in the urea cycle by the splitting off of urea from arginine. It is a central part of the urea cycle, which allows for the disposal of excess nitrogen. L-Ornithine is also a precursor of citrulline and arginine. In order for ornithine produced in the cytosol to be converted to citrulline, it must first cross the inner mitochondrial membrane into the mitochondrial matrix where it is carbamylated by ornithine transcarbamylase. This transfer is mediated by the mitochondrial ornithine transporter (SLC25A15; Ornithine is an amino acid which plays a role in the urea cycle. Ornithine is found in many foods, some of which are soft-necked garlic, orange bell pepper, sunburst squash (pattypan squash), and cucumber.

CAS Number

3184-13-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(+)-s-ornithine	biospider
(2S)-2,5-diaminopentanoic acid	biospider
(S)-2,5-Diaminopentanoate	biospider
(S)-2,5-Diaminopentanoic acid	biospider
(S)-2,5-Diaminovalerate	Generator
(S)-2,5-diaminovaleric acid	biospider
(s)-a,d-diaminovalerate	biospider
(s)-a,d-diaminovaleric acid	biospider
(S)-a,delta-Diaminovalerate	Generator
(S)-a,delta-Diaminovaleric acid	Generator
(S)-a,δ-diaminovalerate	Generator
(S)-a,δ-diaminovaleric acid	Generator
(S)-alpha,delta-Diaminovalerate	Generator
(s)-alpha,delta-diaminovaleric acid	biospider
(s)-ornithine	biospider
(S)-α,δ-diaminovalerate	Generator
(S)-α,δ-diaminovaleric acid	Generator
2,5-diaminopentanoate	biospider
2,5-diaminopentanoic acid	biospider
2,5-diaminovaleric acid	biospider
5-amino-L-Norvaline	biospider
Alpha, delta-diaminovaleric acid	biospider
L-(-)-ornithine	biospider
L-Norvaline, 5-amino-	biospider
L-Ornithine	ChEBI
L-Ornithine (9CI)	biospider
Ornithine, L- (8CI)	biospider
Pentanoic acid, 2,5-diamino-, (S)-	biospider

Chemical Formula

C5H12N2O2

IUPAC name

2,5-diaminopentanoic acid

InChI Identifier

InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)

InChI Key

AHLPHDHHMVZTML-UHFFFAOYSA-N

Isomeric SMILES

NCCCC(N)C(O)=O

Average Molecular Weight

132.161

Monoisotopic Molecular Weight

132.089877638

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