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CHEBI:59204 - carbetocin

Default Structure
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).
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).
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
carbetocin (CHEBI:59204) has role antineoplastic agent (CHEBI:35610)
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
carbetocinaWHO MedNet
carbetocineWHO MedNet
carbetocinoChemIDplus
carbetocinumChemIDplus
Synonyms  Source
1-butanoic acid-2-(O-methyl-L-tyrosine)-1-carbaoxytocinChEBI
1-butyric acid-2-(3-(p-methoxyphenyl)-L-alanine)oxytocinChemIDplus
deamino-2-O-methyltyrosine-1-carbaoxytocinChEBI
FE 992097ChEMBL
FE-992097ChEMBL
LV-101ChEMBL
Brand Name  Source
Duratocin long actingChEMBL
Manual XrefsDatabases
1778VSDB
495DrugCentral
C18365KEGG COMPOUND
D07229KEGG DRUG
DB01282DrugBank
DE2732175Patent
Registry NumbersSources
Beilstein:9985308Beilstein
CAS:37025-55-1ChemIDplus
CAS:37025-55-1KEGG COMPOUND
CAS:37025-55-1KEGG DRUG
Citations