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L-citrulline
Sign in to saveAlso known as N5-carbamoylornithine, N(delta)-Carbamylornithine, (S)-2-Amino-5-ureidopentanoic acid, delta-Ureidonorvaline, N5-(Aminocarbonyl)ornithine, Cit, Citrulline, 2-Amino-5-ureidovaleric acid
The organic compound citrulline is a non-essential α-amino acid. Its name is derived from citrullus, the Latin word for watermelon. Although named and described by gastroenterologists since the late 19th century, it was first isolated from watermelon in 1914 by Japanese researchers Yatarō Koga (古賀彌太郎) and Ryō Ōtake (大嶽了) and further codified by Mitsunori Wada of Tokyo Imperial University in 1930. It has the formula H2NC(O)NH(CH2)3CH(NH2)CO2H. It is a key intermediate in the urea cycle, the pathway by which mammals excrete ammonia by converting it into urea. Citrulline is also produced as a byp
OverviewAI-generated
L-citrulline is a chemical compound with the formula C₆H₁₃N₃O₃. Its IUPAC name is (2S)-2-azaniumyl-5-(carbamoylamino)pentanoate. The substance has a mass of 175.096 and a weight of 175.19. It possesses a charge of 0, an xlogp of -3.6, and a topological polar surface area of 123. The molecule contains three hydrogen bond donors and three hydrogen bond acceptors.
The compound is identified by the NCI Thesaurus ID C53406 and the PubChem CID 6992098. Its canonical SMILES notation is C(CC(C(=O)O)N)CNC(=O)N, while its isomeric SMILES is N[C@@H](CCCNC(N)=O)C(O)=O. The InChIKey for L-citrulline is RHGKLRLOHDJJDR-BYPYZUCNSA-N.
In scientific literature, L-citrulline is the subject of 9,813 PubMed entries. The compound is also referenced by 180 other encyclopedia articles.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C6H13N3O3
- Molecular weight
- 175.19 g/mol
- IUPAC name
- (2S)-2-azaniumyl-5-(carbamoylamino)pentanoate
- SMILES
- C(C[C@@H](C(=O)[O-])[NH3+])CNC(=O)N
- InChIKey
- RHGKLRLOHDJJDR-BYPYZUCNSA-N
- XLogP
- -3.6
- Polar surface area
- 123 Ų
- H-bond donors
- 3
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
9,813 papersvia PubMed
~4 min read
Encyclopedic overview
5 sectionsContents
- Biosynthesis
- Function
- Commercial use
- See also
- References
The organic compound citrulline is a non-essential α-amino acid. Its name is derived from citrullus, the Latin word for watermelon. Although named and described by gastroenterologists since the late 19th century, it was first isolated from watermelon in 1914 by Japanese researchers Yatarō Koga (古賀彌太郎) and Ryō Ōtake (大嶽了) and further codified by Mitsunori Wada of Tokyo Imperial University in 1930. It has the formula H2NC(O)NH(CH2)3CH(NH2)CO2H. It is a key intermediate in the urea cycle, the pathway by which mammals excrete ammonia by converting it into urea. Citrulline is also produced as a byproduct of the enzymatic production of nitric oxide from the amino acid arginine, catalyzed by nitric oxide synthase.
==Biosynthesis== Citrulline can be derived from: from arginine via nitric oxide synthase, as a byproduct of the production of nitric oxide for signaling purposes from ornithine through the breakdown of proline or glutamine/glutamate from asymmetric dimethylarginine via DDAH
Excerpted from Wikipedia’s “L-citrulline” article, available under the CC BY-SA 4.0 licence.