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Record Information
Version3.6
Creation Date2012-09-06 15:16:48 UTC
Update Date2016-02-11 01:28:01 UTC
HMDB IDHMDB14260
Secondary Accession NumbersNone
Metabolite Identification
Common NameDesmopressin
DescriptionDesmopressin is a chemical that is similar to Antidiuretic Hormone (ADH) which is found naturally in the body. It increases urine concentration and decreases urine production. Desmopressin is used to prevent and control excessive thirst, urination, and dehydration caused by injury, surgery, and certain medical conditions, allowing you to sleep through the night without awakening to urinate. It is also used to treat specific types of diabetes insipidus and conditions after head injury or pituitary surgery.
Structure
Thumb
Synonyms
ValueSource
MinirinChEMBL
StimateChEMBL
Stimic acidGenerator
1-desamino-8-D-Arginine vasopressinHMDB
Chemical FormulaC46H64N14O12S2
Average Molecular Weight1069.217
Monoisotopic Molecular Weight1068.426954962
IUPAC Name(2S)-2-{[(2S)-1-[(4R,7S,10S,13S,16S)-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}-5-carbamimidamido-N-(carbamoylmethyl)pentanamide
Traditional Namedesmopressin
CAS Registry Number16679-58-6
SMILES
NC(=O)CC[C@@H]1NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)CCSSC[C@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(N)=O
InChI Identifier
InChI=1S/C46H64N14O12S2/c47-35(62)15-14-29-40(67)58-32(22-36(48)63)43(70)59-33(45(72)60-18-5-9-34(60)44(71)56-28(8-4-17-52-46(50)51)39(66)53-23-37(49)64)24-74-73-19-16-38(65)54-30(21-26-10-12-27(61)13-11-26)41(68)57-31(42(69)55-29)20-25-6-2-1-3-7-25/h1-3,6-7,10-13,28-34,61H,4-5,8-9,14-24H2,(H2,47,62)(H2,48,63)(H2,49,64)(H,53,66)(H,54,65)(H,55,69)(H,56,71)(H,57,68)(H,58,67)(H,59,70)(H4,50,51,52)/t28-,29-,30-,31-,32-,33-,34-/m0/s1
InChI KeyInChIKey=NFLWUMRGJYTJIN-NXBWRCJVSA-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
  • 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
  • Guanidine
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidamide
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antidiuretic Agents
  • Hemostatics
  • Renal Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.10e-01 g/LNot Available
LogP-4.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 mg/mLALOGPS
logP-1ALOGPS
logP-6.1ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)11.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area435.41 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity279.78 m3·mol-1ChemAxon
Polarizability106.19 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00035
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00035
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00035
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10481973
KEGG Compound IDC06944
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDesmopressin
NuGOwiki LinkHMDB14260
Metagene LinkHMDB14260
METLIN IDNot Available
PubChem Compound16051933
PDB IDNot Available
ChEBI ID466861
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Leissinger C, Becton D, Cornell C Jr, Cox Gill J: High-dose DDAVP intranasal spray (Stimate) for the prevention and treatment of bleeding in patients with mild haemophilia A, mild or moderate type 1 von Willebrand disease and symptomatic carriers of haemophilia A. Haemophilia. 2001 May;7(3):258-66. [11380629 ]
  2. Sequence Information [Link]

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Kotnik P, Nielsen J, Kwon TH, Krzisnik C, Frokiaer J, Nielsen S: Altered expression of COX-1, COX-2, and mPGES in rats with nephrogenic and central diabetes insipidus. Am J Physiol Renal Physiol. 2005 May;288(5):F1053-68. Epub 2005 Jan 11. [15644490 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Kotnik P, Nielsen J, Kwon TH, Krzisnik C, Frokiaer J, Nielsen S: Altered expression of COX-1, COX-2, and mPGES in rats with nephrogenic and central diabetes insipidus. Am J Physiol Renal Physiol. 2005 May;288(5):F1053-68. Epub 2005 Jan 11. [15644490 ]
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
References
  1. Loichot C, Cazaubon C, De Jong W, Helwig JJ, Nisato D, Imbs JL, Barthelmebs M: Nitric oxide, but not vasopressin V2 receptor-mediated vasodilation, modulates vasopressin-induced renal vasoconstriction in rats. Naunyn Schmiedebergs Arch Pharmacol. 2000 Mar;361(3):319-26. [10731046 ]
  2. Mechaly I, Laurent F, Portet K, Serrano J, Cros G: Vasopressin V2 (SR121463A) and V1a (SR49059) receptor antagonists both inhibit desmopressin vasorelaxing activity. Eur J Pharmacol. 1999 Nov 3;383(3):287-90. [10594321 ]
  3. Barthelmebs M, Krieger JP, Grima M, Nisato D, Imbs JL: Vascular effects of [Arg8]vasopressin in the isolated perfused rat kidney. Eur J Pharmacol. 1996 Oct 31;314(3):325-32. [8957254 ]
  4. Pequeux C, Keegan BP, Hagelstein MT, Geenen V, Legros JJ, North WG: Oxytocin- and vasopressin-induced growth of human small-cell lung cancer is mediated by the mitogen-activated protein kinase pathway. Endocr Relat Cancer. 2004 Dec;11(4):871-85. [15613460 ]
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
References
  1. Del Tredici AL, Vanover KE, Knapp AE, Bertozzi SM, Nash NR, Burstein ES, Lameh J, Currier EA, Davis RE, Brann MR, Mohell N, Olsson R, Piu F: Identification of novel selective V2 receptor non-peptide agonists. Biochem Pharmacol. 2008 Oct 30;76(9):1134-41. Epub 2008 Aug 12. [18761325 ]
  2. Slusarz MJ, Slusarz R, Ciarkowski J: Investigation of mechanism of desmopressin binding in vasopressin V2 receptor versus vasopressin V1a and oxytocin receptors: molecular dynamics simulation of the agonist-bound state in the membrane-aqueous system. Biopolymers. 2006 Apr 5;81(5):321-38. [16333859 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
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
References
  1. Pequeux C, Keegan BP, Hagelstein MT, Geenen V, Legros JJ, North WG: Oxytocin- and vasopressin-induced growth of human small-cell lung cancer is mediated by the mitogen-activated protein kinase pathway. Endocr Relat Cancer. 2004 Dec;11(4):871-85. [15613460 ]
  2. Dinan TG, O'Brien S, Lavelle E, Scott LV: Further neuroendocrine evidence of enhanced vasopressin V3 receptor responses in melancholic depression. Psychol Med. 2004 Jan;34(1):169-72. [14971638 ]
  3. Craighead M, Milne R, Campbell-Wan L, Watson L, Presland J, Thomson FJ, Marston HM, Macsweeney CP: Characterization of a novel and selective V1B receptor antagonist. Prog Brain Res. 2008;170:527-35. [18655906 ]