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CHEBI:4450 - desmopressin

ChEBI IDCHEBI:4450
ChEBI Namedesmopressin
Stars
DefinitionA 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.
Last Modified22 February 2017
DownloadsMolfile
FormulaC46H64N14O12S2
Net Charge0
Average Mass1069.238
Monoisotopic Mass1068.42696
SMILESN=C(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
InChIInChI=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
InChIKeyNFLWUMRGJYTJIN-PNIOQBSNSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
vasopressin receptor agonist  Any drug which binds to vasopressin receptors and triggers a response.
Applications:
diagnostic agent  A substance administered to aid diagnosis of a disease.
renal agent  A drug used for its effect on the kidneys' regulation of body fluid composition and volume.
vasopressin receptor agonist  Any drug which binds to vasopressin receptors and triggers a response.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
desmopresinaChemIDplus
desmopressinumChemIDplus
desmopressineChemIDplus
desmopressinChemIDplus
Synonyms  Source
1-deamino-8-D-arginine vasopressinChemIDplus
1-desamino-8-D-arginine vasopressinChemIDplus
1-(3-mercaptopropionic acid)-8-D-arginine-vasopressinChEBI
DDAVPDrugBank
Manual XrefsDatabases
C06944KEGG COMPOUND
D00291KEGG DRUG
DB00035DrugBank
817DrugCentral
Registry NumbersSources
Beilstein:4651966Beilstein
CAS:16679-58-6KEGG COMPOUND
CAS:16679-58-6ChemIDplus