CHEBI:4450 - desmopressin

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ChEBI Name desmopressin
ChEBI ID CHEBI:4450
Definition A synthetic analogue of vasopressin in which 3-mercaptopropionic acid replaces the cysteine residue at position 1 and D-arginine replaces the residue at position 8. An antidiuretic, it increases urine concentration and decreases urine production, and is used (usually as the trihydrate of the acetic acid salt) to prevent and control excessive thirst, urination, and dehydration caused by injury, surgery, and certain medical conditions. It is also used in the diagnosis and treatment of cranial diabetes insipidus and in tests of renal function.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C46H64N14O12S2
Net Charge 0
Average Mass 1069.21700
Monoisotopic Mass 1068.427
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)/t28-,29+,30+,31+,32+,33+,34+/m1/s1
InChIKey NFLWUMRGJYTJIN-PNIOQBSNSA-N
SMILES NC(=N)NCCC[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSCCC(=O)N[C@@H](Cc2ccc(O)cc2)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N1)C(=O)NCC(N)=O
Roles Classification
Biological Role(s): vasopressin receptor agonist
Any drug which binds to vasopressin receptors and triggers a response.
Application(s): vasopressin receptor agonist
Any drug which binds to vasopressin receptors and triggers a response.
renal agent
A drug used for its effect on the kidneys' regulation of body fluid composition and volume.
diagnostic agent
A substance administered to aid diagnosis of a disease.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing desmopressin (CHEBI:4450) has role diagnostic agent (CHEBI:33295)
desmopressin (CHEBI:4450) has role renal agent (CHEBI:35846)
desmopressin (CHEBI:4450) has role vasopressin receptor agonist (CHEBI:59727)
desmopressin (CHEBI:4450) is a heterodetic cyclic peptide (CHEBI:24533)
Incoming desmopressin acetate (anhydrous) (CHEBI:59726) has part desmopressin (CHEBI:4450)
IUPAC Name
1-{[(4R,7S,10S,13S,16S)-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-L-prolyl-D-arginylglycinamide
INNs Sources
desmopresina ChemIDplus
desmopressin ChemIDplus
desmopressine ChemIDplus
desmopressinum ChemIDplus
Synonyms Sources
1-(3-mercaptopropionic acid)-8-D-arginine-vasopressin ChEBI
1-deamino-8-D-arginine vasopressin ChemIDplus
1-desamino-8-D-arginine vasopressin ChemIDplus
DDAVP DrugBank
Database Links Databases
817 DrugCentral
C06944 KEGG COMPOUND
D00291 KEGG DRUG
DB00035 DrugBank
View more database links
Registry Numbers Types Sources
16679-58-6 CAS Registry Number KEGG COMPOUND
16679-58-6 CAS Registry Number ChemIDplus
4651966 Beilstein Registry Number Beilstein
Last Modified
22 February 2017