CHEBI:59204 - carbetocin

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ChEBI Name carbetocin
ChEBI ID CHEBI:59204
Definition Oxytocin 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C45H69N11O12S
Net Charge 0
Average Mass 988.16100
Monoisotopic Mass 987.48479
InChI InChI=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
InChIKey NSTRIRCPWQHTIA-DTRKZRJBSA-N
SMILES [H][C@]1(NC(=O)[C@H](Cc2ccc(OC)cc2)NC(=O)CCCSC[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
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
carbetocin ChemIDplus
carbetocino ChemIDplus
carbetocinum ChemIDplus
Synonyms Sources
1-butanoic acid-2-(O-methyl-L-tyrosine)-1-carbaoxytocin ChEBI
1-butyric acid-2-(3-(p-methoxyphenyl)-L-alanine)oxytocin ChemIDplus
deamino-2-O-methyltyrosine-1-carbaoxytocin ChEBI
Manual Xrefs Databases
1778 VSDB
495 DrugCentral
C18365 KEGG COMPOUND
D07229 KEGG DRUG
DB01282 DrugBank
DE2732175 Patent
View more database links
Registry Numbers Types Sources
37025-55-1 CAS Registry Number KEGG DRUG
37025-55-1 CAS Registry Number ChemIDplus
9985308 Beilstein Registry Number Beilstein
Last Modified
22 February 2017