citrulline (CHEBI:18211)

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ChEBI Name	citrulline

ChEBI ID	CHEBI:18211

Definition	The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N⁵-position.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:3730, CHEBI:14002

Supplier Information	ChemicalBook:CB7478532, eMolecules:884088

Download	Molfile XML SDF

Wikipedia	License
The organic compound citrulline is an 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.
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Formula

C6H13N3O3

Net Charge

Average Mass

175.18584

Monoisotopic Mass

175.09569

InChI

InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)

InChIKey

RHGKLRLOHDJJDR-UHFFFAOYSA-N

SMILES

NC(CCCNC(N)=O)C(O)=O

Metabolite of Species	Details
Daphnia magna (NCBI:txid35525)	See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. hapten Any substance capable of eliciting an immune response only when attached to a large carrier such as a protein. Examples include dinitrophenols; oligosaccharides; peptides; and heavy metals.

ChEBI Ontology
Outgoing	citrulline (CHEBI:18211) has role Daphnia magna metabolite (CHEBI:83056) citrulline (CHEBI:18211) has role hapten (CHEBI:59174) citrulline (CHEBI:18211) is a citrullines (CHEBI:23324) citrulline (CHEBI:18211) is conjugate acid of citrullinate (CHEBI:66922)

Incoming	N-acetylcitrulline (CHEBI:49006) has functional parent citrulline (CHEBI:18211) D-citrulline (CHEBI:49007) is a citrulline (CHEBI:18211) L-citrulline (CHEBI:16349) is a citrulline (CHEBI:18211) citrullinate (CHEBI:66922) is conjugate base of citrulline (CHEBI:18211)

IUPAC Names

2-amino-5-(carbamoylamino)pentanoic acid

citrulline

N⁵-carbamoylornithine

Synonyms	Sources
2-Amino-5-uredovaleric acid	KEGG COMPOUND
Cit	IUPAC
citrulina	ChEBI
Citrullin	ChEBI
Citrulline	KEGG COMPOUND
DL-2-amino-5-ureidovaleric acid	ChemIDplus
dl-citrulline	NIST Chemistry WebBook
N⁵-(aminocarbonyl)-DL-ornithine	NIST Chemistry WebBook
N⁵-(aminocarbonyl)ornithine	ChEBI
N⁵-carbamoyl-DL-ornithine	NIST Chemistry WebBook

Citations

Last Modified

18 April 2024