Vasopressin (CHEM035294)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:38:28 UTC
Update Date2016-11-09 01:21:17 UTC
Accession NumberCHEM035294
Identification
Common NameVasopressin
ClassSmall Molecule
DescriptionAntidiuretic hormone, also known commonly as vasopressin, is a nine amino acid peptide secreted from the posterior pituitary. Within hypothalamic neurons, the hormone is packaged in secretory vesicles with a carrier protein called neurophysin, and both are released upon hormone secretion.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-(Phenylalanine)-8-lysine oxytocinHMDB
8-L-Lysine vasopressinHMDB
ADHHMDB
Antidiuretic hormoneHMDB
DiapidHMDB
PitressinHMDB
Pitressin tannateHMDB
PressynHMDB
Lysine vasopressinHMDB
Vasopressin, lysylHMDB
Lys-vasopressinHMDB
Lysyl vasopressinHMDB
Vasopressin, lysineHMDB
Lys vasopressinHMDB
8-Lysine vasopressinHMDB
LypressinHMDB
8 Lysine vasopressinHMDB
PostactonHMDB
Vasopressin, 8-lysineHMDB
Chemical FormulaC46H65N13O12S2
Average Molecular Mass1056.218 g/mol
Monoisotopic Mass1055.432 g/mol
CAS Registry Number11000-17-2
IUPAC Name6-amino-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-13-benzyl-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)hexanamide
Traditional Name6-amino-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-13-benzyl-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)hexanamide
SMILESNCCCCC(NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CC2=CC=C(O)C=C2)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N1)C(=O)NCC(N)=O
InChI IdentifierInChI=1S/C46H65N13O12S2/c47-17-5-4-9-29(40(65)52-22-38(51)63)54-45(70)35-10-6-18-59(35)46(71)34-24-73-72-23-28(48)39(64)55-31(20-26-11-13-27(60)14-12-26)43(68)56-32(19-25-7-2-1-3-8-25)42(67)53-30(15-16-36(49)61)41(66)57-33(21-37(50)62)44(69)58-34/h1-3,7-8,11-14,28-35,60H,4-6,9-10,15-24,47-48H2,(H2,49,61)(H2,50,62)(H2,51,63)(H,52,65)(H,53,67)(H,54,70)(H,55,64)(H,56,68)(H,57,66)(H,58,69)/t28-,29?,30-,31-,32-,33-,34-,35-/m0/s1
InChI KeyBJFIDCADFRDPIO-ZCCHBGLBSA-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
  • 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 Solubility0.05 g/LALOGPS
logP-1.1ALOGPS
logP-6.8ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.43ChemAxon
pKa (Strongest Basic)10.26ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area425.55 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity266.77 m³·mol⁻¹ChemAxon
Polarizability107.34 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-000i-9000000012-c61fa89acd0e2361ff33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9210000224-9c3d4939882c0b8cd77eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dj-9400000110-96f55351a61faa794ab5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-9000000003-326177c7b0d79b1dd2b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fkm-9030000113-30fa91c1f4e25ccb0412Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9110000010-6e88881169913f86b4eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-9000000007-d44ac1ac85d9e90a363aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-9000000037-82c2dffb92e922f16c91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9400000343-3ebda2e8f118233bb791Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000002-d99c2d72e8f1f49a8a59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-9100000016-406128407f4d42e8f2f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002k-9800000114-6e168e682cc646613390Spectrum
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 IDHMDB0001980
FooDB IDFDB022778
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6414
PDB IDNot Available
Wikipedia LinkVasopressin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID53477739
Kegg Compound IDC00840
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Andres M, Pena A, Derick S, Raufaste D, Trojnar J, Wisniewski K, Trueba M, Serradeil-Le Gal C, Guillon G: Comparative pharmacology of bovine, human and rat vasopressin receptor isoforms. Eur J Pharmacol. 2004 Oct 6;501(1-3):59-69.
2. Brown CH, Bourque CW: Mechanisms of rhythmogenesis: insights from hypothalamic vasopressin neurons. Trends Neurosci. 2006 Feb;29(2):108-15. Epub 2005 Dec 5.
3. Cowley AW Jr, Mattson DL, Lu S, Roman RJ: The renal medulla and hypertension. Hypertension. 1995 Apr;25(4 Pt 2):663-73.
4. Guyader D, Patat A, Ellis-Grosse EJ, Orczyk GP: Pharmacodynamic effects of a nonpeptide antidiuretic hormone V2 antagonist in cirrhotic patients with ascites. Hepatology. 2002 Nov;36(5):1197-205.
5. Guillon G, Grazzini E, Andrez M, Breton C, Trueba M, Serradeil-LeGal C, Boccara G, Derick S, Chouinard L, Gallo-Payet N: Vasopressin : a potent autocrine/paracrine regulator of mammal adrenal functions. Endocr Res. 1998 Aug-Nov;24(3-4):703-10.
6. Cintra Ede A, Maciel JA Jr, Araujo S, Castro Md, Martins EF, Falcao AL, Sardinha LA, Terzi RG, Dragosavac D, Cardoso AP, Oliveira RA: Vasopressin serum levels in patients with severe brain lesions and in brain-dead patients. Arq Neuropsiquiatr. 2004 Jun;62(2A):226-32. Epub 2004 Jun 23.
7. Guillon G, Trueba M, Joubert D, Grazzini E, Chouinard L, Cote M, Payet MD, Manzoni O, Barberis C, Robert M, et al.: Vasopressin stimulates steroid secretion in human adrenal glands: comparison with angiotensin-II effect. Endocrinology. 1995 Mar;136(3):1285-95.
8. Scott LV, Dinan TG: Vasopressin as a target for antidepressant development: an assessment of the available evidence. J Affect Disord. 2002 Nov;72(2):113-24.
9. 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.