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L-Citrulline

Catalog No. DB00155 Name DrugBank
CAS Number 372-75-8 Website http://www.ualberta.ca/
M. F. C6H13N3O3 Telephone (780) 492-3111
M. W. 175.18572 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 41

SYNONYMS

IUPAC name
(2S)-2-amino-5-(carbamoylamino)pentanoic acid
IUPAC Traditional name
L-citrulline
Synonyms
N5-carbamylornithine
N5-(Aminocarbonyl)ornithine
N5-Carbamoyl-L-ornithine
Sitrulline
2-Amino-5-uredovaleric acid
Citrulline
delta-Ureidonorvaline
N5-carbamoylornithine

DATABASE IDS

PubChem CID 9750
PubChem SID 46506583
CAS Number 372-75-8

PROPERTIES

Hydrophobicity(logP) -3.9
Solubility 200 g/L (at 20 oC)

DETAILS

Description (English)
Item Information
Drug Groups approved; nutraceutical
Description Citrulline is an amino acid. It is made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family. Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolated.
Indication Used for nutritional supplementation, also for treating dietary shortage or imbalance.
Pharmacology A non-essential amino acid and a precursor of arginine. Citrulline supplements have been claimed to promote energy levels, stimulate the immune system and help detoxify ammonia (a cell toxin). L-citrulline is made from L-ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from L-arginine as a by-product of the reaction catalyzed by the enzyme NO synthase. L-citrulline, while being an amino acid, is not involved in protein synthesis and is not one of the amino acids coded for by DNA. Although citrulline cannot be incorporated in proteins during protein synthesis, several proteins are known to contain citrulline as an amino acid. These citrulline residues are generated by a family of enzymes called peptidylarginine deiminases (PADs), which convert the amino acid arginine into citrulline. Proteins that contain citrulline residues include myelin basic protein (MBP), fillagrin and several histone proteins.
Affected Organisms
Humans and other mammals

REFERENCES