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Showing Compound Oxytocin (FDB023075)

Record Information
Version1.0
Creation date2011-09-21 00:24:18 UTC
Update date2015-10-09 22:33:19 UTC
Primary IDFDB023075
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 [HMDB]
CAS Number50-56-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
(Arg8)-Vasopressinhmdb
(Arg8)-Vasotocinhmdb
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
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
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
Chemical FormulaC43H66N12O12S2
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
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
Isomeric 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
Average Molecular Weight1007.187
Monoisotopic Molecular Weight1006.436457016
Classification
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
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01w0-7211090007-02ded9f4fb62188bcd1c2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100000102-9932076684dd100467c12016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9842101200-f6f6d97cad6b1952b9792016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-9012104006-d088f89ac80bb947ef8c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kj6-3011011009-145137bb0cf8acc974082016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-6970111341-f07368f08e3e4bb508d52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000002-0e271ec3ffcffeb3ba002021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4u-9001000015-43fe697177f713ba1dde2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500024454-88f21ec58b7e9cd96f8a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000002-f636a43bb80aae6d594f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-4000000239-156bd2db8a73e819195e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100002101-0b1da7f1f7e4c461135f2021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC00746
Pubchem Compound ID53477758
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02865
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDOxytocin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Oxytocin-neurophysin 1OXTP01178
Prolyl endopeptidasePREPP48147
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference