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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-03-02 21:33:55 UTC
HMDB IDHMDB15402
Secondary Accession NumbersNone
Metabolite Identification
Common NameCarbetocin
DescriptionCarbetocin is only found in individuals that have used or taken this drug. It is a drug used to control postpartum hemorrhage, bleeding after giving birth. It is an analogue of oxytocin, and its action is similar to that of oxytocin, it causes contraction of the uterus.Carbetocin binds to oxytocin receptors present on the smooth musculature of the uterus, resulting in rhythmic contractions of the uterus, increased frequency of existing contractions, and increased uterine tone. The oxytocin receptor content of the uterus is very low in the non-pregnant state, and increases during pregnancy, reaching a peak at the time of delivery.
Structure
Thumb
Synonyms
ValueSource
1-Butanoic acid-2-(O-methyl-L-tyrosine)-1-carbaoxytocinChEBI
1-Butyric acid-2-(3-(P-methoxyphenyl)-L-alanine)oxytocinChEBI
CarbetocinoChEBI
CarbetocinumChEBI
deamino-2-O-Methyltyrosine-1-carbaoxytocinChEBI
1-Butanoate-2-(O-methyl-L-tyrosine)-1-carbaoxytocinGenerator
1-Butyrate-2-(3-(P-methoxyphenyl)-L-alanine)oxytocinGenerator
1-deamino-1-Monocarba-2-(tyr(ome))-oxytocinMeSH
DepotocinMeSH
DcomotMeSH
Chemical FormulaC45H69N11O12S
Average Molecular Weight988.161
Monoisotopic Molecular Weight987.484787417
IUPAC Name(2S)-2-{[(2S)-1-[(3R,6S,9S,12S,15S)-12-[(2S)-butan-2-yl]-9-(2-carbamoylethyl)-6-(carbamoylmethyl)-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosane-3-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)-4-methylpentanamide
Traditional Namecarbetocino
CAS Registry Number37025-55-1
SMILES
[H][C@]1(NC(=O)[C@H](CC2=CC=C(OC)C=C2)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
InChI Identifier
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
InChI KeyNSTRIRCPWQHTIA-DTRKZRJBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Cyclic alpha peptide
  • Leucine or derivatives
  • Macrolactam
  • Proline or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Phenoxy compound
  • Anisole
  • N-acylpyrrolidine
  • Phenol ether
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Methoxybenzene
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Fatty acyl
  • Fatty amide
  • Benzenoid
  • N-acyl-amine
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Primary carboxylic acid amide
  • Lactam
  • Thioether
  • Dialkylthioether
  • Organoheterocyclic compound
  • Ether
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-tocolytic Agents
  • Labor Induction Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.65e-02 g/LNot Available
LogP-2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.026 mg/mLALOGPS
logP0.14ALOGPS
logP-3.6ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)11.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area362.51 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity250.18 m3·mol-1ChemAxon
Polarizability101 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01282
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01282
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01282
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID16736854
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarbetocin
NuGOwiki LinkHMDB15402
Metagene LinkHMDB15402
METLIN IDNot Available
PubChem Compound16681432
PDB IDNot Available
ChEBI ID59204
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for oxytocin. The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol- calcium second messenger system
Gene Name:
OXTR
Uniprot ID:
P30559
Molecular weight:
42771.0
References
  1. Engstrom T, Barth T, Melin P, Vilhardt H: Oxytocin receptor binding and uterotonic activity of carbetocin and its metabolites following enzymatic degradation. Eur J Pharmacol. 1998 Aug 21;355(2-3):203-10. [PubMed:9760035 ]
  2. Gimpl G, Postina R, Fahrenholz F, Reinheimer T: Binding domains of the oxytocin receptor for the selective oxytocin receptor antagonist barusiban in comparison to the agonists oxytocin and carbetocin. Eur J Pharmacol. 2005 Mar 7;510(1-2):9-16. [PubMed:15740719 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]