CHEBI:7872 - oxytocin

Main ChEBI Ontology Automatic Xrefs
ChEBI Name oxytocin
ChEBI ID CHEBI:7872
Definition A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C43H66N12O12S2
Net Charge 0
Average Mass 1007.18982
InChI InChI=1S/C43H66N12O12S2/c1-5-22(4)35-42(66)49-26(12-13-32(45)57)38(62)51-29(17-33(46)58)39(63)53-30(20-69-68-19-25(44)36(60)50-28(40(64)54-35)16-23-8-10-24(56)11-9-23)43(67)55-14-6-7-31(55)41(65)52-27(15-21(2)3)37(61)48-18-34(47)59/h8-11,21-22,25-31,35,56H,5-7,12-20,44H2,1-4H3,(H2,45,57)(H2,46,58)(H2,47,59)(H,48,61)(H,49,66)(H,50,60)(H,51,62)(H,52,65)(H,53,63)(H,54,64)/t22-,25-,26-,27-,28-,29-,30-,31-,35-/m0/s1
InChIKey XNOPRXBHLZRZKH-DSZYJQQASA-N
SMILES [H][C@]1(NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](N)CSSC[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)[C@@H](C)CC
Roles Classification
Biological Role(s): hormone
Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.
(via peptide hormone )
Application(s): oxytocic
A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients).
vasodilator agent
A drug used to cause dilation of the blood vessels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing oxytocin (CHEBI:7872) has role oxytocic (CHEBI:36063)
oxytocin (CHEBI:7872) has role vasodilator agent (CHEBI:35620)
oxytocin (CHEBI:7872) is a heterodetic cyclic peptide (CHEBI:24533)
oxytocin (CHEBI:7872) is a peptide hormone (CHEBI:25905)
IUPAC Name
1-({(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-(4-hydroxybenzyl)-13-[(1S)-1-methylpropyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl}carbonyl)-L-prolyl-L-leucylglycinamide
INNs Sources
oxitocina ChemIDplus
oxytocin ChemIDplus
oxytocine ChemIDplus
oxytocinum ChemIDplus
Synonyms Sources
(1-Hemicystine)oxytocin ChemIDplus
3-Isoleucine-8-leucine vasopressin ChemIDplus
Endopituitrina ChemIDplus
L-Cysteinyl-L-tyrosyl-L-isoleucyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-L-leucylglycinamide cyclic(1-6)-disulfide ChemIDplus
Ocytocin KEGG COMPOUND
OT KEGG COMPOUND
OXT KEGG COMPOUND
Oxytocin KEGG COMPOUND
Brand Names Sources
Orasthin ChemIDplus
Pitocin DrugBank
Piton S ChemIDplus
Syntocinon ChemIDplus
Syntocinon DrugBank
Database Links Databases
C00746 KEGG COMPOUND
D00089 KEGG DRUG
DB00107 DrugBank
HMDB02865 HMDB
Oxytocin Wikipedia
US2938891 Patent
US3076797 Patent
View more database links
Registry Numbers Types Sources
3586108 Beilstein Registry Number Beilstein
50-56-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11134819 PubMed citation CiteXplore
13305558 PubMed citation CiteXplore
15815422 PubMed citation CiteXplore
18593851 PubMed citation CiteXplore
18988842 PubMed citation CiteXplore
19104313 PubMed citation CiteXplore
19369205 PubMed citation CiteXplore
19482229 PubMed citation CiteXplore
24706799 PubMed citation CiteXplore
25209411 PubMed citation CiteXplore
Last Modified
28 Ноябрь 2014