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:CB3750054, eMolecules:26755894, eMolecules:533030, ZINC000000083315

Download	Molfile XML SDF

Wikipedia	License
Tryptophan (symbol Trp or W) is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromatic beta carbon substituent. Tryptophan is also a precursor to the neurotransmitter serotonin, the hormone melatonin, and vitamin B3 (niacin). It is encoded by the codon UGG. Like other amino acids, tryptophan is a zwitterion at physiological pH where the amino group is protonated (–NH+3; pKa = 9.39) and the carboxylic acid is deprotonated ( –COO−; pKa = 2.38). Humans and many animals cannot synthesize tryptophan: they need to obtain it through their diet, making it an essential amino acid. Tryptophan is named after the digestive enzymes trypsin, which were used in its first isolation from casein proteins. It was assigned the one-letter symbol W based on the double ring being visually suggestive to the bulky letter.
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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

18 April 2024