desmopressin   Click here for help

GtoPdb Ligand ID: 2182

Synonyms: 1-deamino,D-AVP | [deamino-Cys1,D-Arg8]vasopressin | dDAVP | Noctiva®
Approved drug
desmopressin is an approved drug (FDA (1978))
Comment: Synthetic analogue of AVP. As is the case with many peptide molecules, there is ambiguity in the stereochemistry of the chemical structure of desmopressin. The structure shown here does not specify stereochemistry and so may vary from the representations shown on other resources linked to from the table above. PubChem also includes the following structures for desmopressin: (CID 16051933 and CID 5311065).
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2D Structure
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Canonical SMILES NC(=O)CC1NC(=O)C(CCC(=O)N)NC(=O)C(Cc2ccccc2)NC(=O)C(NC(=O)CCSSCC(NC1=O)C(=O)N1CCCC1C(=O)NC(C(=O)NCC(=O)N)CCCN=C(N)N)Cc1ccc(cc1)O
Isomeric SMILES NC(=O)CC1NC(=O)C(CCC(=O)N)NC(=O)C(Cc2ccccc2)NC(=O)C(NC(=O)CCSSCC(NC1=O)C(=O)N1CCCC1C(=O)NC(C(=O)NCC(=O)N)CCCN=C(N)N)Cc1ccc(cc1)O
InChI 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)
1. Cheng LL, Stoev S, Manning M, Derick S, Pena A, Mimoun MB, Guillon G. (2004)
Design of potent and selective agonists for the human vasopressin V1b receptor based on modifications of [deamino-cys1]arginine vasopressin at position 4.
J Med Chem, 47: 2375-2388. [PMID:15084136]
2. Chini B, Mouillac B, Ala Y, Balestre MN, Trumpp-Kallmeyer S, Hoflack J, Elands J, Hibert M, Manning M, Jard S et al.. (1995)
Tyr115 is the key residue for determining agonist selectivity in the V1a vasopressin receptor.
EMBO J, 14 (10): 2176-82. [PMID:7774575]
3. Cotte N, Balestre MN, Phalipou S, Hibert M, Manning M, Barberis C, Mouillac B. (1998)
Identification of residues responsible for the selective binding of peptide antagonists and agonists in the V2 vasopressin receptor.
J Biol Chem, 273 (45): 29462-8. [PMID:9792651]
4. Jasper JR, Harrell CM, O'Brien JA, Pettibone DJ. (1995)
Characterization of the human oxytocin receptor stably expressed in 293 human embryonic kidney cells.
Life Sci, 57 (24): 2253-61. [PMID:7475979]
5. Nakamura S, Yamamura Y, Itoh S, Hirano T, Tsujimae K, Aoyama M, Kondo K, Ogawa H, Shinohara T, Kan K et al.. (2000)
Characterization of a novel nonpeptide vasopressin V(2)-agonist, OPC-51803, in cells transfected human vasopressin receptor subtypes.
Br J Pharmacol, 129 (8): 1700-6. [PMID:10780976]
6. Phalipou S, Cotte N, Carnazzi E, Seyer R, Mahe E, Jard S, Barberis C, Mouillac B. (1997)
Mapping peptide-binding domains of the human V1a vasopressin receptor with a photoactivatable linear peptide antagonist.
J Biol Chem, 272 (42): 26536-44. [PMID:9334232]
7. Saito M, Tahara A, Sugimoto T. (1997)
1-desamino-8-D-arginine vasopressin (DDAVP) as an agonist on V1b vasopressin receptor.
Biochem Pharmacol, 53: 1711-1717. [PMID:9264324]
8. Serradeil-Le Gal C, Raufaste D, Double-Cazanave E, Guillon G, Garcia C, Pascal M, Maffrand JP. (2000)
Binding properties of a selective tritiated vasopressin V2 receptor antagonist, [H]-SR 121463.
Kidney Int, 58 (4): 1613-22. [PMID:11012895]
9. Tahara A, Saito M, Sugimoto T, Tomura Y, Wada K, Kusayama T, Tsukada J, Ishii N, Yatsu T, Uchida W et al.. (1998)
Pharmacological characterization of the human vasopressin receptor subtypes stably expressed in Chinese hamster ovary cells.
Br J Pharmacol, 125 (7): 1463-70. [PMID:9884074]
10. Thibonnier M, Preston JA, Dulin N, Wilkins PL, Berti-Mattera LN, Mattera R. (1997)
The human V3 pituitary vasopressin receptor: ligand binding profile and density-dependent signaling pathways.
Endocrinology, 138 (10): 4109-22. [PMID:9322919]