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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H13N3O3.ClH
Molecular Weight 211.647
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CITRULLINE HYDROCHLORIDE

SMILES

Cl.N[C@@H](CCCNC(N)=O)C(O)=O

InChI

InChIKey=RSQCFPZQHNPAAZ-WCCKRBBISA-N
InChI=1S/C6H13N3O3.ClH/c7-4(5(10)11)2-1-3-9-6(8)12;/h4H,1-3,7H2,(H,10,11)(H3,8,9,12);1H/t4-;/m0./s1

HIDE SMILES / InChI

Description

Citrulline (name derived from citrullus, the Latin word for watermelon, from which it was first isolated) 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 nitric oxide synthase (NOS) family. Citrulline supplements have been claimed to promote energy levels, stimulate the immune system and help detoxify ammonia (a cell toxin). Citrulline is not involved in protein synthesis. Several pharmacokinetic studies have confirmed that citrulline is efficiently absorbed when administered orally. Oral citrulline could be used to deliver arginine to the systemic circulation or as a protein anabolic agent in specific clinical situations (for example in case of malnourishment), because recent data have suggested that citrulline, although not a component of proteins, stimulates protein synthesis in skeletal muscle through the mammalian target of rapamycin signaling pathway. Citrulline is converted to L-arginine by argininosuccinate synthase. L-arginine is in turn responsible for citrulline's therapeutic effects. Many of L-arginine's activities, including its possible anti-atherogenic actions, may be accounted for by its role as the precursor to nitric oxide (NO).

Approval Year

PubMed