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CHEBI:16349 - L-citrulline
| Formula | C6H13N3O3 |
| Net Charge | 0 |
| Average Mass | 175.188 |
| Monoisotopic Mass | 175.09569 |
| SMILES | NC(=O)NCCC[C@H](N)C(=O)O |
| 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 |
| Wikipedia |
|---|
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Homo sapiens (ncbitaxon:9606) | - | DOI (10.1038/nbt.2488) | |
| Escherichia coli (ncbitaxon:562) | |||
| - | PubMed (179975) | ||
| - | PubMed (21988831) | ||
| Arabidopsis thaliana (ncbitaxon:3702) | - | PubMed (8278506) | |
| Saccharomyces cerevisiae (ncbitaxon:4932) | - | PubMed (24678285) | Source: yeast.sf.net |
| Mus musculus (ncbitaxon:10090) | - | PubMed (19425150) | Source: BioModels - MODEL1507180067 |
| Roles Classification |
|---|
| Chemical Roles: | Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid). Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid). Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). |
| Biological Roles: | 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. 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. 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). 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. Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. |
| Applications: | 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. 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. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| 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 Relation(s) |
| 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 |
|---|
| L-citrulline |
| (2S)-2-amino-5-(carbamoylamino)pentanoic acid |
| N5-carbamoyl-L-ornithine |
| Synonyms | Source |
|---|---|
| L-Citrulline | KEGG COMPOUND |
| 2-Amino-5-ureidovaleric acid | KEGG COMPOUND |
| CITRULLINE | PDBeChem |
| Nδ-carbamylornithine | ChemIDplus |
| δ-ureidonorvaline | ChemIDplus |
| α-amino-δ-ureidovaleric acid | ChemIDplus |
| Manual Xrefs | Databases |
|---|---|
| C00327 | KEGG COMPOUND |
| CIR | PDBeChem |
| D07706 | KEGG DRUG |
| DB00155 | DrugBank |
| HMDB0000904 | HMDB |
| L-CITRULLINE | MetaCyc |
| Citrulline | Wikipedia |
| C00001348 | KNApSAcK |
| YMDB00060 | YMDB |
| ECMDB00904 | ECMDB |
| 3103 | DrugCentral |
| Registry Numbers | Sources |
|---|---|
| Beilstein:6055157 | Beilstein |
| Gmelin:774677 | Gmelin |
| Reaxys:1725416 | Reaxys |
| CAS:372-75-8 | KEGG COMPOUND |
| CAS:372-75-8 | ChemIDplus |
| Citations |
|---|