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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:30 UTC
Update Date2021-09-14 15:46:38 UTC
HMDB IDHMDB0001980
Secondary Accession Numbers
  • HMDB0002781
  • HMDB01980
  • HMDB02781
Metabolite Identification
Common NameVasopressin
DescriptionVasopressin, also known as pitressin or ADH, 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. Vasopressin is a very strong basic compound (based on its pKa). In humans, vasopressin is involved in vasopressin regulation of water homeostasis. In other words, vasopressin is secreted in spite of the presence of hypoosmolality (hyponatremia) when the arterial blood volume is low.
Structure
Data?1582752221
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 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 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
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+307.06632859911
AllCCS[M-H]-285.49832859911
DeepCCS[M+H]+292.70630932474
DeepCCS[M-H]-291.05330932474
DeepCCS[M-2H]-325.08630932474
DeepCCS[M+Na]+298.86330932474
AllCCS[M+H]+307.132859911
AllCCS[M+H-H2O]+308.032859911
AllCCS[M+NH4]+306.232859911
AllCCS[M+Na]+305.932859911
AllCCS[M-H]-285.532859911
AllCCS[M+Na-2H]-290.732859911
AllCCS[M+HCOO]-296.432859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vasopressin 10V, Positive-QTOFsplash10-000i-9000000012-c61fa89acd0e2361ff332017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vasopressin 20V, Positive-QTOFsplash10-004i-9210000224-9c3d4939882c0b8cd77e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vasopressin 40V, Positive-QTOFsplash10-00dj-9400000110-96f55351a61faa794ab52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vasopressin 10V, Negative-QTOFsplash10-0udr-9000000003-326177c7b0d79b1dd2b62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vasopressin 20V, Negative-QTOFsplash10-0fkm-9030000113-30fa91c1f4e25ccb04122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vasopressin 40V, Negative-QTOFsplash10-0006-9110000010-6e88881169913f86b4ee2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vasopressin 10V, Negative-QTOFsplash10-0udi-9000000007-d44ac1ac85d9e90a363a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vasopressin 20V, Negative-QTOFsplash10-0udl-9000000037-82c2dffb92e922f16c912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vasopressin 40V, Negative-QTOFsplash10-002f-9400000343-3ebda2e8f118233bb7912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vasopressin 10V, Positive-QTOFsplash10-0a4i-9000000002-d99c2d72e8f1f49a8a592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vasopressin 20V, Positive-QTOFsplash10-052r-9100000016-406128407f4d42e8f2f32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vasopressin 40V, Positive-QTOFsplash10-002k-9800000114-6e168e682cc6466133902021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Locations
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Neuron
  • Pancreas
  • Platelet
  • Testis
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0000053 (0.0000046-0.0000062) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0000007 +/- 0.0000001 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0000025 +/- 0.0000004 uMAdult (>18 years old)BothMotor neuron disease (MND) details
Associated Disorders and Diseases
Disease References
Motor neuron disease
  1. Seckl JR, Lightman SL, Guiloff RJ: Elevated cerebrospinal fluid vasopressin in motor neuron disease. J Neurol Neurosurg Psychiatry. 1987 Jun;50(6):795-7. [PubMed:3612158 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022778
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00840
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVasopressin
METLIN ID6414
PubChem Compound53477739
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000360
Good Scents 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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:9888562 ]
  7. 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. [PubMed: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. [PubMed: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. [PubMed:12200202 ]

Only showing the first 10 proteins. There are 11 proteins in total.

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

Only showing the first 10 proteins. There are 11 proteins in total.