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Record Information
Version3.6
Creation Date2006-05-22 15:12:15 UTC
Update Date2016-05-13 20:06:37 UTC
HMDB IDHMDB02865
Secondary Accession NumbersNone
Metabolite Identification
Common NameOxytocin
DescriptionOxytocin is a mammalian hormone that also acts as a neurotransmitter in the brain. In women, it is released mainly after distention of the cervix and vagina during labor, and after stimulation of the nipples, facilitating birth and breastfeeding, respectively. Oxytocin is released during orgasm in both sexes. In the brain, oxytocin is involved in social recognition and bonding, and might be involved in the formation of trust between people. -- Wikipedia; In the pituitary gland, oxytocin is packaged in large, dense-core vesicles, where it is bound to neurophysin as shown in the inset of the figure; neurophysin is a large peptide fragment of the giant precursor protein molecule from which oxytocin is derived by enzymatic cleavage. -- Wikipedia; Oxytocin is a peptide of nine amino acids (a nonapeptide). The sequence is cysteine - tyrosine - isoleucine - glutamine - asparagine - cysteine - proline - leucine - glycine (CYIQNCPLG). The cysteine residues form a sulfur bridge. Oxytocin has a molecular mass of 1007 daltons. One international unit (IU) of oxytocin is the equivalent of about 2 micrograms of pure peptide. -- Wikipedia; Oxytocin has peripheral (hormonal) actions, and also has actions in the brain. The actions of oxytocin are mediated by specific, high affinity oxytocin receptors. The oxytocin receptor is a G-protein-coupled receptor which requires Mg2+ and cholesterol. It belongs to the rhodopsin-type (class I) group of G-protein-coupled receptors. -- Wikipedia.
Structure
Thumb
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
Chemical FormulaC43H66N12O12S2
Average Molecular Weight1007.187
Monoisotopic Molecular Weight1006.436457016
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
CAS Registry Number50-56-6
SMILES
CC[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 Identifier
InChI=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 KeyInChIKey=XNOPRXBHLZRZKH-MQYCRUOZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCyclic peptides
Alternative Parents
Substituents
  • Cyclic alpha peptide
  • N-acyl-alpha amino acid or derivatives
  • Macrolactam
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • N-acylpyrrolidine
  • Phenol
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Fatty amide
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Cyclic alcohol
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Organic disulfide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.055 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity252.11 m3·mol-1ChemAxon
Polarizability102.58 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adrenal Gland
  • Adrenal Medulla
  • Cervical
  • Fibroblasts
  • Gonads
  • Hypothalamus
  • Muscle
  • Nerve Cells
  • Neuron
  • Ovary
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified5.1e-06 +/- 9e-07 uMNot SpecifiedBothNormal details
UrineDetected and Quantified0.0000009 +/- 0.0000001 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified9.2e-06 +/- 3.9e-06 uMNot SpecifiedNot SpecifiedPrader-Willi syndrome details
Cerebrospinal Fluid (CSF)Detected and Quantified9.2e-06 +/- 3.9e-06 uMNot SpecifiedNot SpecifiedPrader-Willi syndrome details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023075
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00746
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxytocin
NuGOwiki LinkHMDB02865
Metagene LinkHMDB02865
METLIN ID1691
PubChem Compound53477758
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceZhou, Yiming. Method for preparation of oxytocin by solid phase synthesis. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 20pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [2249637 ]
  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. [10027619 ]
  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. [15375538 ]
  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. [16634548 ]
  5. Lippert TH, Mueck AO, Seeger H, Pfaff A: Effects of oxytocin outside pregnancy. Horm Res. 2003;60(6):262-71. [14646403 ]
  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. [2851753 ]
  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. [10983343 ]
  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. [12802445 ]
  9. Arias F: Pharmacology of oxytocin and prostaglandins. Clin Obstet Gynecol. 2000 Sep;43(3):455-68. [10949750 ]
  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. [8827091 ]
  11. Nicholson HD, Pickering BT: Oxytocin, a male intragonadal hormone. Regul Pept. 1993 Apr 29;45(1-2):253-6. [8511352 ]
  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. [9665335 ]
  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. [9469276 ]
  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. [10949083 ]
  15. 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. [10834934 ]

Enzymes

General function:
Involved in neurohypophyseal hormone activity
Specific function:
Oxytocin causes contraction of the smooth muscle of the uterus and of the mammary gland
Gene Name:
OXT
Uniprot ID:
P01178
Molecular weight:
12721.5
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
General function:
Involved in proteolysis
Specific function:
Release of an N-terminal amino acid, cleaves before cysteine, leucine as well as other amino acids. Degrades peptide hormones such as oxytocin, vasopressin and angiotensin III, and plays a role in maintaining homeostasis during pregnancy. May be involved in the inactivation of neuronal peptides in the brain. Cleaves Met-enkephalin and dynorphin. Binds angiotensin IV and may be the angiotensin IV receptor in the brain
Gene Name:
LNPEP
Uniprot ID:
Q9UIQ6
Molecular weight:
117348.1
General function:
Involved in serine-type endopeptidase activity
Specific function:
Cleaves peptide bonds on the C-terminal side of prolyl residues within peptides that are up to approximately 30 amino acids long
Gene Name:
PREP
Uniprot ID:
P48147
Molecular weight:
80698.9
General function:
Involved in DNA binding
Specific function:
Interacts with the upstream promoter region of the oxytocin receptor gene. May be a transcriptional enhancer in the up-regulation of the oxytocin receptor gene at parturition. Since it lacks a putative transactivation domain, it may behave as a transcriptional repressor when it dimerize among himself. May also serve as a transcriptional activator by dimerizing with other (usually larger) basic-zipper proteins and recruiting them to specific DNA-binding sites. May be involved in the cellular stress response
Gene Name:
MAFF
Uniprot ID:
Q9ULX9
Molecular weight:
17760.2
General function:
Involved in oxytocin receptor activity
Specific function:
Not Available
Gene Name:
OXTR
Uniprot ID:
A0T1J2
Molecular weight:
10410.1
General function:
Involved in neurohypophyseal hormone activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q9UEW6
Molecular weight:
4312.0