CHEBI:78539 - zofenopril

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name zofenopril
ChEBI ID CHEBI:78539
Definition A proline derivative that is 4-(phenylsulfanyl)-L-proline in which the amine proton is replaced by a (2S)-3-(benzoylsulfanyl)-2-methylpropanoyl group. A prodrug for zofenoprilat.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Toni Morrison
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C22H23NO4S2
Net Charge 0
Average Mass 429.55200
Monoisotopic Mass 429.107
InChI InChI=1S/C22H23NO4S2/c1-15(14-28-22(27)16-8-4-2-5-9-16)20(24)23-13-18(12-19(23)21(25)26)29-17-10-6-3-7-11-17/h2-11,15,18-19H,12-14H2,1H3,(H,25,26)/t15-,18+,19+/m1/s1
InChIKey IAIDUHCBNLFXEF-MNEFBYGVSA-N
SMILES C[C@H](CSC(=O)c1ccccc1)C(=O)N1C[C@H](C[C@H]1C(O)=O)Sc1ccccc1
Roles Classification
Chemical Role(s): 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).
apoptosis inhibitor
Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): anticonvulsant
A drug used to prevent seizures or reduce their severity.
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).
cardioprotective agent
Any protective agent that is able to prevent damage to the heart.
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.
vasodilator agent
A drug used to cause dilation of the blood vessels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing zofenopril (CHEBI:78539) has role anticonvulsant (CHEBI:35623)
zofenopril (CHEBI:78539) has role apoptosis inhibitor (CHEBI:68494)
zofenopril (CHEBI:78539) has role cardioprotective agent (CHEBI:77307)
zofenopril (CHEBI:78539) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
zofenopril (CHEBI:78539) has role prodrug (CHEBI:50266)
zofenopril (CHEBI:78539) has role vasodilator agent (CHEBI:35620)
zofenopril (CHEBI:78539) is a N-acyl-L-amino acid (CHEBI:21644)
zofenopril (CHEBI:78539) is a L-proline derivative (CHEBI:84186)
zofenopril (CHEBI:78539) is a aryl sulfide (CHEBI:35683)
zofenopril (CHEBI:78539) is a thioester (CHEBI:51277)
zofenopril (CHEBI:78539) is conjugate acid of zofenopril(1−) (CHEBI:82601)
Incoming zofenopril(1−) (CHEBI:82601) is conjugate base of zofenopril (CHEBI:78539)
IUPAC Name
(4S)-1-[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)-L-proline
INNs Sources
zofenopril KEGG DRUG
zofenopril WHO MedNet
zofénopril WHO MedNet
zofenoprilum ChemIDplus
Manual Xrefs Databases
2866 DrugCentral
D08688 KEGG DRUG
Zofenopril Wikipedia
View more database links
Registry Numbers Types Sources
6443047 Reaxys Registry Number Reaxys
81872-10-8 CAS Registry Number ChemIDplus
81872-10-8 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
21377823 PubMed citation Europe PMC
21394524 PubMed citation Europe PMC
21888941 PubMed citation Europe PMC
22090052 PubMed citation Europe PMC
22107891 PubMed citation Europe PMC
22162922 PubMed citation Europe PMC
22455094 PubMed citation Europe PMC
22707187 PubMed citation Europe PMC
23030285 PubMed citation Europe PMC
23096377 PubMed citation Europe PMC
23552127 PubMed citation Europe PMC
23582628 PubMed citation Europe PMC
23882152 PubMed citation Europe PMC
24211724 PubMed citation Europe PMC
24415271 PubMed citation Europe PMC
24501330 PubMed citation Europe PMC
24583202 PubMed citation Europe PMC
24935917 PubMed citation Europe PMC
Last Modified
22 February 2017