CHEBI:135756 - spirapril

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name spirapril
ChEBI ID CHEBI:135756
Definition An azaspiro compound resulting from the formal condensation of the amino group of (8S)-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid with the carboxy group of N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanine. It is a prodrug for the antihypertensive drug spiraprilat.
Stars This entity has been manually annotated by a third party.
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C22H30N2O5S2
Net Charge 0
Average Mass 466.617
Monoisotopic Mass 466.15961
InChI InChI=1S/C22H30N2O5S2/c1-3-29-21(28)17(10-9-16-7-5-4-6-8-16)23-15(2)19(25)24-14-22(30-11-12-31-22)13-18(24)20(26)27/h4-8,15,17-18,23H,3,9-14H2,1-2H3,(H,26,27)/t15-,17-,18-/m0/s1
InChIKey HRWCVUIFMSZDJS-SZMVWBNQSA-N
SMILES C([C@@H](N[C@@H](CCC1=CC=CC=C1)C(OCC)=O)C)(=O)N2CC3(C[C@H]2C(=O)O)SCCS3
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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).
Application(s): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing spirapril (CHEBI:135756) has functional parent spiraprilat (CHEBI:141522)
spirapril (CHEBI:135756) has role antihypertensive agent (CHEBI:35674)
spirapril (CHEBI:135756) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
spirapril (CHEBI:135756) has role prodrug (CHEBI:50266)
spirapril (CHEBI:135756) is a azaspiro compound (CHEBI:35624)
spirapril (CHEBI:135756) is a dicarboxylic acid monoester (CHEBI:36244)
spirapril (CHEBI:135756) is a dipeptide (CHEBI:46761)
spirapril (CHEBI:135756) is a dithioketal (CHEBI:59800)
spirapril (CHEBI:135756) is a ethyl ester (CHEBI:23990)
spirapril (CHEBI:135756) is a pyrrolidinecarboxylic acid (CHEBI:46767)
spirapril (CHEBI:135756) is a secondary amino compound (CHEBI:50995)
spirapril (CHEBI:135756) is a tertiary carboxamide (CHEBI:140326)
IUPAC Name
(8S)-7-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid
Manual Xrefs Databases
2474 DrugCentral
D08529 KEGG DRUG
DB01348 DrugBank
HMDB0015438 HMDB
Spirapril Wikipedia
View more database links
Registry Numbers Types Sources
4277924 Reaxys Registry Number Reaxys
83647-97-6 CAS Registry Number DrugCentral
83647-97-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10499560 PubMed citation Europe PMC
10499561 PubMed citation Europe PMC
12613273 PubMed citation Europe PMC
8638865 PubMed citation Europe PMC
9345854 PubMed citation Europe PMC
Last Modified
03 August 2018