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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:48 UTC
Update Date2017-10-23 19:06:15 UTC
HMDB IDHMDB0014260
Secondary Accession Numbers
  • HMDB14260
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
1-desamino-8-D-Arginine vasopressinHMDB
1-deamino-8-D-Arginine vasopressinMeSH
Acetate, desmopressinMeSH
AdiuretinMeSH
DesmogalenMeSH
Desmopressin acetateMeSH
Desmopressine ferringMeSH
Ferring brand 2 OF desmopressin acetateMeSH
IQFA brand OF desmopressin acetateMeSH
MinirinMeSH
MinurinMeSH
Vasopressin, 1-deamino-8-D-arginineMeSH
Vasopressin, deamino arginineMeSH
Adiuretin SDMeSH
Apotex brand OF deamino arginine vasopressinMeSH
DDAVPMeSH
deamino Arginine vasopressinMeSH
Desmopressin monoacetate, trihydrateMeSH
DesmosprayMeSH
DesmotabsMeSH
Monoacetate, trihydrate desmopressinMeSH
Vasopressin, 1-desamino-8-arginineMeSH
apo-DesmopressinMeSH
OctostimMeSH
Trihydrate desmopressin monoacetateMeSH
1-desamino-8-Arginine vasopressinMeSH
Arginine vasopressin, deaminoMeSH
Desmopressin monoacetateMeSH
Ferring brand 1 OF desmopressin acetateMeSH
Ferring, desmopressineMeSH
Galen brand OF desmopressin acetateMeSH
Hoyer brand OF desmopressin acetateMeSH
Monoacetate, desmopressinMeSH
NocutilMeSH
Norgine brand OF desmopressin acetateMeSH
OctimMeSH
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 KeyNFLWUMRGJYTJIN-NXBWRCJVSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Cyclic alpha peptide
  • Arginine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Proline or derivatives
  • Macrolactam
  • 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
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Organic disulfide
  • Guanidine
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidamide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Imine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.11 g/LNot Available
LogP-4.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity279.78 m³·mol⁻¹ChemAxon
Polarizability106.19 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-9011031000-1d6802a7b18080efdaebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9010000000-c5fdb0c4c4cf6d1cfafcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-8952211020-3a2efe5f548886dadf6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aba-9000003002-4cf0ccd456fee85d2b71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pcd-9010113003-c0ade215a530007b5989View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056u-9344010102-0406e167780abef3e26dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00035 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00035 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
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. doi: 10.1016/j.bcp.2008.08.004. Epub 2008 Aug 12. [PubMed: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. [PubMed:16333859 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed: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. [PubMed: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. [PubMed: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. doi: 10.1016/S0079-6123(08)00440-8. [PubMed:18655906 ]