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CHEBI:7872 - oxytocin

ChEBI IDCHEBI:7872
ChEBI Nameoxytocin
Stars
DefinitionA 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.
Last Modified27 November 2020
DownloadsMolfile
FormulaC43H66N12O12S2
Net Charge0
Average Mass1007.207
Monoisotopic Mass1006.43646
SMILES[H][C@@]1([C@@H](C)CC)NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](N)CSSC[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O
InChIInChI=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
InChIKeyXNOPRXBHLZRZKH-DSZYJQQASA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
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.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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)
Incoming Relation(s)
demoxytocin (CHEBI:135900) has functional parent oxytocin (CHEBI:7872)
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  Source
oxitocinaChemIDplus
oxytocinChemIDplus
oxytocineChemIDplus
oxytocinumChemIDplus
Synonyms  Source
(1-Hemicystine)oxytocinChemIDplus
3-Isoleucine-8-leucine vasopressinChemIDplus
EndopituitrinaChemIDplus
L-Cysteinyl-L-tyrosyl-L-isoleucyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-L-leucylglycinamide cyclic(1-6)-disulfideChemIDplus
OcytocinKEGG COMPOUND
OTKEGG COMPOUND
Brand Names  Source
OrasthinChemIDplus
PitocinDrugBank
Piton SChemIDplus
SyntocinonChemIDplus
SyntocinonDrugBank
Manual XrefsDatabases
2042DrugCentral
C00746KEGG COMPOUND
D00089KEGG DRUG
DB00107DrugBank
HMDB0002865HMDB
OxytocinWikipedia
US2938891Patent
US3076797Patent
Registry NumbersSources
Beilstein:3586108Beilstein
CAS:50-56-6ChemIDplus
Citations