EMBL-EBI | Chemical Biology | ChEBI
Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search
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 |
|---|---|---|---|
| Arabidopsis thaliana (ncbitaxon:3702) | - | PubMed (8278506) | |
| Escherichia coli (ncbitaxon:562) | |||
| - | PubMed (179975) | ||
| - | PubMed (21988831) | ||
| Homo sapiens (ncbitaxon:9606) | - | DOI (10.1038/nbt.2488) | |
| Mus musculus (ncbitaxon:10090) | - | PubMed (19425150) | Source: BioModels - MODEL1507180067 |
| Saccharomyces cerevisiae (ncbitaxon:4932) | - | PubMed (24678285) | Source: yeast.sf.net |
| 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: | human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). 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). Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). micronutrient Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions. Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. 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: | anti-anaemic agent A compound which increases either the number of red cells or the amount of haemoglobin in the blood. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. cardiovascular drug A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume. 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. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. antihypertensive agent Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism. anti-asthmatic agent Any compound that has anti-asthmatic effects. hypoglycemic agent A drug which lowers the blood glucose level. 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 anti-anaemic agent (CHEBI:75835) |
| L-citrulline (CHEBI:16349) has role anti-asthmatic agent (CHEBI:65023) |
| L-citrulline (CHEBI:16349) has role antihypertensive agent (CHEBI:35674) |
| L-citrulline (CHEBI:16349) has role antineoplastic agent (CHEBI:35610) |
| L-citrulline (CHEBI:16349) has role cardiovascular drug (CHEBI:35554) |
| L-citrulline (CHEBI:16349) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908) |
| L-citrulline (CHEBI:16349) has role geroprotector (CHEBI:176497) |
| L-citrulline (CHEBI:16349) has role human metabolite (CHEBI:77746) |
| L-citrulline (CHEBI:16349) has role hypoglycemic agent (CHEBI:35526) |
| 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 |
|---|
| (2S)-2-amino-5-(carbamoylamino)pentanoic acid |
| N5-carbamoyl-L-ornithine |
| L-citrulline |
| Synonyms | Source |
|---|---|
| 2-Amino-5-ureidovaleric acid | KEGG COMPOUND |
| Cit | ChemIDplus |
| Citrulline | KEGG COMPOUND |
| CITRULLINE | PDBeChem |
| N5-(aminocarbonyl)-L-ornithine | ChemIDplus |
| 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 |
| Registry Numbers | Sources |
|---|---|
| Reaxys:1725416 | Reaxys |
| Beilstein:6055157 | Beilstein |
| Gmelin:774677 | Gmelin |
| CAS:372-75-8 | KEGG COMPOUND |
| CAS:372-75-8 | ChemIDplus |
| Citations |
|---|