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CHEBI:141522 - spiraprilat

ChEBI IDCHEBI:141522
ChEBI Namespiraprilat
Stars
DefinitionAn azaspiro compound that is spirapril in which the ethyl ester group has been hydrolysed to the corresponding carboxylic acid group. It is the active metabolite of the angiotensin-converting enzyme (ACE) inhibitor spirapril.
Last Modified3 August 2018
SubmitterBijay
DownloadsMolfile
FormulaC20H26N2O5S2
Net Charge0
Average Mass438.571
Monoisotopic Mass438.12831
SMILESC[C@H](N[C@@H](CCc1ccccc1)C(=O)O)C(=O)N1CC2(C[C@H]1C(=O)O)SCCS2
InChIInChI=1S/C20H26N2O5S2/c1-13(21-15(18(24)25)8-7-14-5-3-2-4-6-14)17(23)22-12-20(28-9-10-29-20)11-16(22)19(26)27/h2-6,13,15-16,21H,7-12H2,1H3,(H,24,25)(H,26,27)/t13-,15-,16-/m0/s1
InChIKeyFMMDBLMCSDRUPA-BPUTZDHNSA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor  An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).
Applications:
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor  An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
ChEBI Ontology
Outgoing Relation(s)
spiraprilat (CHEBI:141522) has role antihypertensive agent (CHEBI:35674)
spiraprilat (CHEBI:141522) has role drug metabolite (CHEBI:49103)
spiraprilat (CHEBI:141522) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
spiraprilat (CHEBI:141522) is a azaspiro compound (CHEBI:35624)
spiraprilat (CHEBI:141522) is a dicarboxylic acid (CHEBI:35692)
spiraprilat (CHEBI:141522) is a dipeptide (CHEBI:46761)
spiraprilat (CHEBI:141522) is a dithioketal (CHEBI:59800)
spiraprilat (CHEBI:141522) is a pyrrolidinecarboxylic acid (CHEBI:46767)
spiraprilat (CHEBI:141522) is a secondary amino compound (CHEBI:50995)
spiraprilat (CHEBI:141522) is a tertiary carboxamide (CHEBI:140326)
Incoming Relation(s)
spirapril (CHEBI:135756) has functional parent spiraprilat (CHEBI:141522)
IUPAC Name 
(8S)-7-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid
Synonyms  Source
SCH-33861SUBMITTER
7-[N-(1(S)-carboxy-3-phenylpropyl)-S-alanyl]-1,4-dithia-7-azaspiro[4.4]nonane-8(S)-carboxylic acidChEBI
SpiraprilateChemIDplus
SpiraprilatumChemIDplus
(8S)-7-((S)-N-((S)-1-Carboxy-3-phenylpropyl)alanyl)-1,4-dithia-7-azaspiro(4.4)nonane-8-carboxylic acidChemIDplus
Manual XrefsDatabases
3033702PubChem Compound
D03775KEGG DRUG
SpiraprilatWikipedia
Registry NumbersSources
Reaxys:4275869Reaxys
CAS:83602-05-5ChemIDplus
Citations