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Record Information
Version3.6
Creation Date2006-05-22 14:17:30 UTC
Update Date2016-02-11 01:05:11 UTC
HMDB IDHMDB01980
Secondary Accession Numbers
  • HMDB02781
Metabolite Identification
Common NameVasopressin
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.
Structure
Thumb
Synonyms
ValueSource
3-(Phenylalanine)-8-lysine oxytocinHMDB
8-L-Lysine vasopressinHMDB
ADHHMDB
Antidiuretic hormoneHMDB
DiapidHMDB
PitressinHMDB
Pitressin tannateHMDB
PressynHMDB
Chemical FormulaC46H65N13O12S2
Average Molecular Weight1056.218
Monoisotopic Molecular Weight1055.431705989
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
CAS Registry Number11000-17-2
SMILES
NCCCCC(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 Identifier
InChI=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 KeyInChIKey=BJFIDCADFRDPIO-ZCCHBGLBSA-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 Solubility0.05 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity266.77 m3·mol-1ChemAxon
Polarizability107.34 Å3ChemAxon
Number of Rings4ChemAxon
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
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Nerve Cells
  • Neuron
  • Pancreas
  • Platelet
  • Testes
  • Thyroid Gland
Pathways
NameSMPDB LinkKEGG Link
Angiotensin MetabolismSMP00587Not Available
Benazepril PathwaySMP00145Not Available
Candesartan Action PathwaySMP00158Not Available
Captopril PathwaySMP00146Not Available
Cilazapril PathwaySMP00147Not Available
Enalapril PathwaySMP00148Not Available
Eprosartan Action PathwaySMP00159Not Available
Forasartan Action PathwaySMP00160Not Available
Fosinopril PathwaySMP00149Not Available
Irbesartan Action PathwaySMP00161Not Available
Lisinopril PathwaySMP00150Not Available
Losartan Action PathwaySMP00162Not Available
Moexipril PathwaySMP00151Not Available
Olmesartan Action PathwaySMP00163Not Available
Perindopril PathwaySMP00152Not Available
Quinapril PathwaySMP00153Not Available
Ramipril PathwaySMP00154Not Available
Rescinnamine PathwaySMP00155Not Available
Spirapril PathwaySMP00156Not Available
Telmisartan Action PathwaySMP00164Not Available
Temocapril Action PathwaySMP00733Not Available
Trandolapril PathwaySMP00157Not Available
Valsartan Action PathwaySMP00165Not Available
Vasopressin Regulation of Water HomeostasisSMP00322Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0000053 (0.0000046-0.0000062) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified7e-07 +/- 1e-07 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified2.5e-06 +/- 4e-07 uMAdult (>18 years old)BothMotor neuron disease (MND) 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 IDFDB022778
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00840
BioCyc IDD-Heptoses
BiGG IDNot Available
Wikipedia LinkVasopressin
NuGOwiki LinkHMDB01980
Metagene LinkHMDB01980
METLIN ID6414
PubChem Compound53477739
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. 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. [15464063 ]
  3. Brown CH, Bourque CW: Mechanisms of rhythmogenesis: insights from hypothalamic vasopressin neurons. Trends Neurosci. 2006 Feb;29(2):108-15. Epub 2005 Dec 5. [16330104 ]
  4. Cowley AW Jr, Mattson DL, Lu S, Roman RJ: The renal medulla and hypertension. Hypertension. 1995 Apr;25(4 Pt 2):663-73. [7721413 ]
  5. 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. [12395330 ]
  6. 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. [9888562 ]
  7. Cintra Ede A, Maciel JA Jr, Araujo S, Castro M, 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. [15235722 ]
  8. 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. [7867583 ]
  9. 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. [12200202 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for arginine vasopressin. The activity of this receptor is mediated by G proteins which activate a phosphatidyl- inositol-calcium second messenger system. Has been involved in social behaviors, including affiliation and attachment
Gene Name:
AVPR1A
Uniprot ID:
P37288
Molecular weight:
46799.1
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for arginine vasopressin. The activity of this receptor is mediated by G proteins which activate adenylate cyclase
Gene Name:
AVPR2
Uniprot ID:
P30518
Molecular weight:
40278.6
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for arginine vasopressin. The activity of this receptor is mediated by G proteins which activate a phosphatidyl- inositol-calcium second messenger system
Gene Name:
AVPR1B
Uniprot ID:
P47901
Molecular weight:
46970.3
General function:
Involved in calcium channel activity
Specific function:
Core component of multiple SCF-like ECS (Elongin-Cullin 2/5-SOCS-box protein) E3 ubiquitin-protein ligase complexes, which mediate the ubiquitination and subsequent proteasomal degradation of target proteins. As a scaffold protein may contribute to catalysis through positioning of the substrate and the ubiquitin- conjugating enzyme. The functional specificity of the E3 ubiquitin-protein ligase complex depends on the variable substrate recognition component. ECS(SOCS1) seems to direct ubiquitination of JAk2. Seems to be involved poteosomal degradation of p53/TP53 stimulated by adenovirus E1B-55 kDa protein. May form a cell surface vasopressin receptor
Gene Name:
CUL5
Uniprot ID:
Q93034
Molecular weight:
90954.6
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 G-protein coupled receptor protein signaling pathway
Specific function:
May be active in signaling pathway in an autocrine or paracrine fashion in several tissues. Receptor for neuropeptide S, it may mediate its action, such as inhibitory effects, on cell growth. Involved in pathogenesis of asthma and other IgE-mediated diseases
Gene Name:
NPSR1
Uniprot ID:
Q6W5P4
Molecular weight:
42686.3
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 neurohypophyseal hormone activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q9UEW6
Molecular weight:
4312.0
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Not Available
Gene Name:
AVPR1
Uniprot ID:
Q3S2J4
Molecular weight:
46854.2
General function:
Involved in receptor activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q9UH72
Molecular weight:
1071.2
General function:
Involved in receptor activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q16271
Molecular weight:
1905.1