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 175.096
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:10090) Source: BioModels - MODEL1507180067 See: PubMed
Arabidopsis thaliana (NCBI:3702) See: PubMed
Saccharomyces cerevisiae (NCBI:4932) Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:562) See: PubMed
Escherichia coli (NCBI:562) See: PubMed
Homo sapiens (NCBI:9606) See: DOI
Roles Classification
Chemical Role(s): 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.
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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)
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
Database Links 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 Beilstein Registry Number Beilstein
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 Types Sources
11862757 PubMed citation Europe PMC
17190852 PubMed citation Europe PMC
18022291 PubMed citation Europe PMC
19173225 PubMed citation Europe PMC
21067832 PubMed citation Europe PMC
21915076 PubMed citation Europe PMC
21955999 PubMed citation Europe PMC
22119809 PubMed citation Europe PMC
22345866 PubMed citation Europe PMC
22348173 PubMed citation Europe PMC
22387109 PubMed citation Europe PMC
22388927 PubMed citation Europe PMC
22402328 PubMed citation Europe PMC
22402472 PubMed citation Europe PMC
22512552 PubMed citation Europe PMC
Last Modified
18 August 2017