Oxytocin (CED0001248)

Record Information
Version1.0
Creation Date2016-05-25 18:14:35 UTC
Update Date2026-04-13 20:28:21 UTC
Accession NumberCHEM021876
Identification
Common NameOxytocin
ClassSmall Molecule
Description
Oxytocin (C43H66N12O12S2) is a compound with an average molecular weight of 1,007 g/mol. With an average molecular weight of 1,007 g/mol, Oxytocin is a heavy molecule. Oxytocin belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. The compound is found in or released from 17 recorded sources. These include healthcare, pharmaceuticals, and veterinary products such as gynecologicals and posterior pituitary lobe hormones. It is also associated with food, food processing, and cookware, specifically food preservation, the preparation of vinegar, and fermentation processes for beer. Other recorded sources include building and construction materials like ceilings, as well as household cleaning and consumer products such as tobacco smoke filters, tobacco product cases, perfumes within detergents and soaps, and non electric simulated smoking devices. Additionally, it is linked to electrical and electronic equipment, including electrodes, fixed capacitors and their manufacture, discharge lamps, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for oxytocin include intramuscular, intravascular, intravenous, and topical administration. In terms of biological activity, the compound acts on four recorded protein targets. It serves as an agonist of the oxytocin receptor (OXTR) as well as the vasopressin V1a receptor (AVPR1A), vasopressin V1b receptor (AVPR1B), and vasopressin V2 receptor (AVPR2).
Contaminant TypeNot Available
Chemical Structure
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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01w0-7211090007-02ded9f4fb62188bcd1cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9100000102-9932076684dd100467c1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9842101200-f6f6d97cad6b1952b979Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dr-9012104006-d088f89ac80bb947ef8cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kj6-3011011009-145137bb0cf8acc97408Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001l-6970111341-f07368f08e3e4bb508d5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9000000002-0e271ec3ffcffeb3ba00Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4u-9001000015-43fe697177f713ba1ddeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9500024454-88f21ec58b7e9cd96f8aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9000000002-f636a43bb80aae6d594fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-4000000239-156bd2db8a73e819195eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9100002101-0b1da7f1f7e4c461135fNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
44.0Log mg/kg[20:78]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
329Posterior pituitary lobe hormonesHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Oxytocin receptor structureClick to view 3D structureOxytocin receptorP30559HumansPredicted (SEA)0.0778492
Vasopressin V1a receptor structureClick to view 3D structureVasopressin V1a receptorP37288HumansPredicted (SEA)0.0778492
Click to view 3D structureOxytocin-like receptorQ5D7U5Gallus gallusPredicted (SEA)0.0778492
Vasopressin V2 receptor structureClick to view 3D structureVasopressin V2 receptorP30518HumansPredicted (SEA)0.0778492
Click to view 3D structureVasopressin V1b receptorP47901HumansPredicted (SEA)0.0778492
Click to view 3D structureOxytocin receptorP70536Rattus norvegicusPredicted (SEA)0.389246
Click to view 3D structureVasopressin V2 receptorQ00788Rattus norvegicusPredicted (SEA)1.01204
Click to view 3D structureVasopressin V1a receptorP30560Rattus norvegicusPredicted (SEA)1.32344
Click to view 3D structureOxytocin receptorP97926Mus musculusPredicted (SEA)0.0778492
Click to view 3D structureVasopressin V1b receptorP48974Rattus norvegicusPredicted (SEA)1.55698
Click to view 3D structureVasopressin V2 receptorP48044Bos taurusPredicted (SEA)0.700643
Click to view 3D structureVasopressin V2 receptorP32307Sus scrofaPredicted (SEA)1.71268
Click to view 3D structureAlpha-amylaseP56634Tenebrio molitorPredicted (SEA)7.94062
Calcium and integrin-binding protein 1 structureClick to view 3D structureCalcium and integrin-binding protein 1Q99828HumansPredicted (SEA)9.73115
Prothrombin structureClick to view 3D structureProthrombinP00734HumansPredicted (SEA)67.651
Melanoma-associated antigen 4 structureClick to view 3D structureMelanoma-associated antigen 4P43358HumansPredicted (SEA)8.95266
Plasma kallikrein structureClick to view 3D structurePlasma kallikreinP03952HumansPredicted (SEA)44.6076
Plasminogen structureClick to view 3D structurePlasminogenP00747HumansPredicted (SEA)53.716
T-cell surface antigen CD2 structureClick to view 3D structureT-cell surface antigen CD2P06729HumansPredicted (SEA)8.79696
Kallikrein-7 structureClick to view 3D structureKallikrein-7P49862HumansPredicted (SEA)15.3363
Cathepsin G structureClick to view 3D structureCathepsin GP08311HumansPredicted (SEA)17.2047
Kallikrein-4 structureClick to view 3D structureKallikrein-4Q9Y5K2HumansPredicted (SEA)17.8275
Myeloblastin structureClick to view 3D structureMyeloblastinP24158HumansPredicted (SEA)10.5875
Click to view 3D structureKallikrein-14Q9P0G3HumansPredicted (SEA)19.5402
Kallikrein-5 structureClick to view 3D structureKallikrein-5Q9Y337HumansPredicted (SEA)20.3965
Concentrations
Not Available
External Links
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.