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

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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

Last Modified

23 December 2018