Oxytocin (CHEM021876)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:14:35 UTC
Update Date2016-11-09 01:17:23 UTC
Accession NumberCHEM021876
Identification
Common NameOxytocin
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(Arg8)-vasopressinHMDB
(Arg8)-vasotocinHMDB
alpha-HypophamineHMDB
ArgipressinHMDB
Argpressin acetateHMDB
Biotinyl-(arg8)-vasopressinHMDB
Cys-tyr-ile-GLN-asn-cys-pro-arg-gly-NH2HMDB
Cys-tyr-ile-GLN-asn-cys-pro-leu-gly-NH2HMDB
Cys-tyr-ile-THR-asn-cys-gly-leu-gly-NH2HMDB
Cys-tyr-phe-GLN-asn-cys-pro-arg-gly-NH2HMDB
Cys-tyr-phe-GLN-asn-cys-pro-lys-gly-NH2HMDB
Disulfide bridge cys1-cys6HMDB
Gly-leu-pro-cHMDB
OcytocinHMDB
OXTHMDB
Oxytocin 10 usp units in dextrose 5%HMDB
Oxytocin 20 usp units in dextrose 5%HMDB
Oxytocin 5 usp units in dextrose 5%HMDB
Oxytocin acetateHMDB
Oxytocin injectionHMDB
PitocinHMDB
SyntocinonHMDB
(2S)-2-[({1-[(4R,7S,10S,13S,16S,19R)-19-amino-13-[(2S)-butan-2-yl]-6,9,12,15,18-pentahydroxy-10-[2-(C-hydroxycarbonimidoyl)ethyl]-7-[(C-hydroxycarbonimidoyl)methyl]-16-[(4-hydroxyphenyl)methyl]-1,2-dithia-5,8,11,14,17-pentaazacycloicosa-5,8,11,14,17-pentaene-4-carbonyl]pyrrolidin-2-yl}(hydroxy)methylidene)amino]-N-[(C-hydroxycarbonimidoyl)methyl]-4-methylpentanimidateHMDB
Chemical FormulaC43H66N12O12S2
Average Molecular Mass1007.187 g/mol
Monoisotopic Mass1006.436 g/mol
CAS Registry Number50-56-6
IUPAC Name(2S)-2-({1-[(4R,7S,10S,13S,16S,19R)-19-amino-13-[(2S)-butan-2-yl]-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl}formamido)-N-(carbamoylmethyl)-4-methylpentanamide
Traditional Name(2S)-2-({1-[(4R,7S,10S,13S,16S,19R)-19-amino-13-[(2S)-butan-2-yl]-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl}formamido)-N-(carbamoylmethyl)-4-methylpentanamide
SMILESCC[C@H](C)[C@@H]1NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)[C@@H](N)CSSC[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O)C(=O)N1CCCC1C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O
InChI IdentifierInChI=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
InChI KeyXNOPRXBHLZRZKH-MQYCRUOZSA-N
Chemical Taxonomy
Description 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
  • Proline or derivatives
  • Macrolactam
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Benzenoid
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Organic disulfide
  • Amino acid or derivatives
  • Primary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Primary aliphatic amine
  • Carbonyl group
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.055 g/LALOGPS
logP-0.69ALOGPS
logP-5ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)7.65ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area399.53 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity252.11 m³·mol⁻¹ChemAxon
Polarizability102.58 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01w0-7211090007-02ded9f4fb62188bcd1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100000102-9932076684dd100467c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9842101200-f6f6d97cad6b1952b979Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-9012104006-d088f89ac80bb947ef8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kj6-3011011009-145137bb0cf8acc97408Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-6970111341-f07368f08e3e4bb508d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000002-0e271ec3ffcffeb3ba00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4u-9001000015-43fe697177f713ba1ddeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500024454-88f21ec58b7e9cd96f8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000002-f636a43bb80aae6d594fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-4000000239-156bd2db8a73e819195eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100002101-0b1da7f1f7e4c461135fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002865
FooDB IDFDB023075
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID1691
PDB IDNot Available
Wikipedia LinkOxytocin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID53477758
Kegg Compound IDC00746
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Zhou, Yiming. Method for preparation of oxytocin by solid phase synthesis. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 20pp.
2. Wildt L, Kissler S, Licht P, Becker W: Sperm transport in the human female genital tract and its modulation by oxytocin as assessed by hysterosalpingoscintigraphy, hysterotonography, electrohysterography and Doppler sonography. Hum Reprod Update. 1998 Sep-Oct;4(5):655-66.
3. Cassoni P, Marrocco T, Sapino A, Allia E, Bussolati G: Evidence of oxytocin/oxytocin receptor interplay in human prostate gland and carcinomas. Int J Oncol. 2004 Oct;25(4):899-904.
4. Shimo T, Nishiike S, Masuoka M, Seki S, Tsuchida H: [Intraoperative anaphylactic shock induced by methylergometrine and oxytocin]. Masui. 2006 Apr;55(4):447-50.
5. Lippert TH, Mueck AO, Seeger H, Pfaff A: Effects of oxytocin outside pregnancy. Horm Res. 2003;60(6):262-71.
6. Legros JJ, Chiodera P, Geenen V: Inhibitory action of exogenous oxytocin on plasma cortisol in normal human subjects: evidence of action at the adrenal level. Neuroendocrinology. 1988 Aug;48(2):204-6.
7. Gavrilenko VG, Stadnikov AA, Esipov VK, Mit'kin AF: [The use of oxytocin in the combined treatment of suppurative-necrotic lesions of the feet in diabetic patients]. Vestn Khir Im I I Grek. 2000;159(3):59-62.
8. Ailamazyan EK, Petrishchev NN, Vivulanets EV, Maryutina LV, Mindukshev IV, Khachaturyan AR: Effects of oxytocin and prostaglandin F(2alpha) (enzaprost) on platelet aggregation. Bull Exp Biol Med. 2002 Nov;134(5):439-41.
9. Arias F: Pharmacology of oxytocin and prostaglandins. Clin Obstet Gynecol. 2000 Sep;43(3):455-68.
10. Uvnas-Moberg K, Eriksson M: Breastfeeding: physiological, endocrine and behavioural adaptations caused by oxytocin and local neurogenic activity in the nipple and mammary gland. Acta Paediatr. 1996 May;85(5):525-30.
11. Nicholson HD, Pickering BT: Oxytocin, a male intragonadal hormone. Regul Pept. 1993 Apr 29;45(1-2):253-6.
12. Frayne J, Nicholson HD: Localization of oxytocin receptors in the human and macaque monkey male reproductive tracts: evidence for a physiological role of oxytocin in the male. Mol Hum Reprod. 1998 Jun;4(6):527-32.
13. Gazvani MR, Luckas MJ, Drakeley AJ, Emery SJ, Alfirevic Z, Walkinshaw SA: Intraumbilical oxytocin for the management of retained placenta: a randomized controlled trial. Obstet Gynecol. 1998 Feb;91(2):203-7.
14. El Majdoubi M, Poulain DA, Theodosis DT: Activity-dependent morphological synaptic plasticity in an adult neurosecretory system: magnocellular oxytocin neurons of the hypothalamus. Biochem Cell Biol. 2000;78(3):317-27.
15. Ivell R, Furuya K, Brackmann B, Dawood Y, Khan-Dawood F: Expression of the oxytocin and vasopressin genes in human and baboon gonadal tissues. Endocrinology. 1990 Dec;127(6):2990-6.
16. Jagla W, Wiede A, Dietzmann K, Rutkowski K, Hoffmann W: Co-localization of TFF3 peptide and oxytocin in the human hypothalamus. FASEB J. 2000 Jun;14(9):1126-31.