CHEBI:16349 - L-citrulline

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ChEBI Name L-citrulline
ChEBI ID CHEBI:16349
ChEBI ASCII Name L-citrulline
Definition The L-enantiomer of citrulline.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41489, CHEBI:6203, CHEBI:13092, CHEBI:21257
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Formula C6H13N3O3
Net Charge 0
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)/t4-/m0/s1
InChIKey RHGKLRLOHDJJDR-BYPYZUCNSA-N
SMILES N[C@@H](CCCNC(N)=O)C(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Arabidopsis thaliana (NCBI:txid3702) See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
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): Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
micronutrient
Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
EC 1.14.13.39 (nitric oxide synthase) inhibitor
An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
(via citrulline )
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.
(via citrulline )
Application(s): nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
protective agent
Synthetic or natural substance which is given to prevent a disease or disorder or are used in the process of treating a disease or injury due to a poisonous agent.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing L-citrulline (CHEBI:16349) has role Escherichia coli metabolite (CHEBI:76971)
L-citrulline (CHEBI:16349) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
L-citrulline (CHEBI:16349) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
L-citrulline (CHEBI:16349) has role human metabolite (CHEBI:77746)
L-citrulline (CHEBI:16349) has role micronutrient (CHEBI:27027)
L-citrulline (CHEBI:16349) has role mouse metabolite (CHEBI:75771)
L-citrulline (CHEBI:16349) has role nutraceutical (CHEBI:50733)
L-citrulline (CHEBI:16349) has role protective agent (CHEBI:50267)
L-citrulline (CHEBI:16349) is a citrulline (CHEBI:18211)
L-citrulline (CHEBI:16349) is enantiomer of D-citrulline (CHEBI:49007)
L-citrulline (CHEBI:16349) is tautomer of L-citrulline zwitterion (CHEBI:57743)
Incoming N-acetyl-L-citrulline (CHEBI:49002) has functional parent L-citrulline (CHEBI:16349)
N2-succinyl-L-citrulline (CHEBI:51309) has functional parent L-citrulline (CHEBI:16349)
L-citrulline-d2 (CHEBI:192078) is a L-citrulline (CHEBI:16349)
D-citrulline (CHEBI:49007) is enantiomer of L-citrulline (CHEBI:16349)
L-citrulline residue (CHEBI:83397) is substituent group from L-citrulline (CHEBI:16349)
L-citrulline zwitterion (CHEBI:57743) is tautomer of L-citrulline (CHEBI:16349)
IUPAC Names
(2S)-2-amino-5-(carbamoylamino)pentanoic acid
L-citrulline
N5-carbamoyl-L-ornithine
Synonyms Sources
(S)-2-Amino-5-ureidopentanoic acid HMDB
2-Amino-5-ureidovaleric acid KEGG COMPOUND
α-amino-δ-ureidovaleric acid ChemIDplus
Cit ChemIDplus
CITRULLINE PDBeChem
Citrulline KEGG COMPOUND
δ-ureidonorvaline ChemIDplus
L-2-Amino-5-ureidovaleric acid HMDB
L-Citrulline KEGG COMPOUND
N5-(aminocarbonyl)-L-ornithine ChemIDplus
N5-(Aminocarbonyl)ornithine DrugBank
N5-carbamoylornithine DrugBank
Nδ-carbamylornithine ChemIDplus
Manual Xrefs Databases
3103 DrugCentral
C00001348 KNApSAcK
C00327 KEGG COMPOUND
CIR PDBeChem
Citrulline Wikipedia
D07706 KEGG DRUG
DB00155 DrugBank
ECMDB00904 ECMDB
HMDB0000904 HMDB
L-CITRULLINE MetaCyc
YMDB00060 YMDB
View more database links
Registry Numbers Types Sources
1725416 Reaxys Registry Number Reaxys
372-75-8 CAS Registry Number ChemIDplus
6055157 Beilstein Registry Number Beilstein
774677 Gmelin Registry Number Gmelin
Citations Waiting for Citations
Last Modified
18 August 2017