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CHEBI:59204 - carbetocin

ChEBI IDCHEBI:59204
ChEBI Namecarbetocin
Stars
DefinitionOxytocin in which the hydrogen on the phenolic hydroxy group is substituted by methyl, the amino group on the cysteine residue is substituted by hydrogen, and the sulfur of the cysteine residue is replaced by a methylene group. A synthetic carba-analogue of oxytocin, it is used to control bleeding after giving birth. Like oxytocin, it causes contraction of the uterus.
Last Modified22 February 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC45H69N11O12S
Net Charge0
Average Mass988.179
Monoisotopic Mass987.48479
SMILES[H][C@@]1([C@@H](C)CC)NC(=O)[C@H](Cc2ccc(OC)cc2)NC(=O)CCCSC[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/C45H69N11O12S/c1-6-25(4)38-44(66)51-28(15-16-34(46)57)40(62)52-31(21-35(47)58)41(63)54-32(23-69-18-8-10-37(60)50-30(42(64)55-38)20-26-11-13-27(68-5)14-12-26)45(67)56-17-7-9-33(56)43(65)53-29(19-24(2)3)39(61)49-22-36(48)59/h11-14,24-25,28-33,38H,6-10,15-23H2,1-5H3,(H2,46,57)(H2,47,58)(H2,48,59)(H,49,61)(H,50,60)(H,51,66)(H,52,62)(H,53,65)(H,54,63)(H,55,64)/t25-,28-,29-,30-,31-,32-,33-,38-/m0/s1
InChIKeyNSTRIRCPWQHTIA-DTRKZRJBSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Application:
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).
ChEBI Ontology
Outgoing Relation(s)
carbetocin (CHEBI:59204) has role oxytocic (CHEBI:36063)
carbetocin (CHEBI:59204) is a heterodetic cyclic peptide (CHEBI:24533)
IUPAC Name 
1-{[(3R,6S,9S,12S,15S)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-[(2S)-butan-2-yl]-15-(4-methoxybenzyl)-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosan-3-yl]carbonyl}-L-prolyl-L-leucylglycinamide
INNs  Source
carbetocinChemIDplus
carbetocinoChemIDplus
carbetocinumChemIDplus
Synonyms  Source
1-butyric acid-2-(3-(p-methoxyphenyl)-L-alanine)oxytocinChemIDplus
1-butanoic acid-2-(O-methyl-L-tyrosine)-1-carbaoxytocinChEBI
deamino-2-O-methyltyrosine-1-carbaoxytocinChEBI
Manual XrefsDatabases
DB01282DrugBank
D07229KEGG DRUG
DE2732175Patent
C18365KEGG COMPOUND
495DrugCentral
1778VSDB
Registry NumbersSources
Beilstein:9985308Beilstein
CAS:37025-55-1ChemIDplus
CAS:37025-55-1KEGG DRUG
CAS:37025-55-1KEGG COMPOUND