CHEBI:141522 - spiraprilat

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name spiraprilat
ChEBI ID CHEBI:141522
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Bijay
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C20H26N2O5S2
Net Charge 0
Average Mass 438.564
Monoisotopic Mass 438.12831
InChI InChI=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
InChIKey FMMDBLMCSDRUPA-BPUTZDHNSA-N
SMILES C([C@@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C)(=O)N2CC3(C[C@H]2C(=O)O)SCCS3
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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).
drug metabolite

Application(s): antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
(8S)-7-((S)-N-((S)-1-Carboxy-3-phenylpropyl)alanyl)-1,4-dithia-7-azaspiro(4.4)nonane-8-carboxylic acid ChemIDplus
7-[N-(1(S)-carboxy-3-phenylpropyl)-S-alanyl]-1,4-dithia-7-azaspiro[4.4]nonane-8(S)-carboxylic acid ChEBI
SCH-33861 SUBMITTER
Spiraprilate ChemIDplus
Spiraprilatum ChemIDplus
Manual Xrefs Databases
3033702 Pubchem accession
D03775 KEGG DRUG
Spiraprilat Wikipedia
View more database links
Registry Numbers Types Sources
4275869 Reaxys Registry Number Reaxys
83602-05-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1384174 PubMed citation Europe PMC
7505361 PubMed citation Europe PMC
8061850 PubMed citation Europe PMC
9269955 PubMed citation Europe PMC
Last Modified
03 August 2018