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CHEBI:78539 - zofenopril

ChEBI IDCHEBI:78539
ChEBI Namezofenopril
Stars
DefinitionA 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.
Last Modified22 February 2017
Submittertmorrison
DownloadsMolfile
FormulaC22H23NO4S2
Net Charge0
Average Mass429.563
Monoisotopic Mass429.10685
SMILESC[C@H](CSC(=O)c1ccccc1)C(=O)N1C[C@@H](Sc2ccccc2)C[C@H]1C(=O)O
InChIInChI=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
InChIKeyIAIDUHCBNLFXEF-MNEFBYGVSA-N
Wikipedia
Roles Classification
Chemical Role:
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).
apoptosis inhibitor  Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
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).
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.
anticonvulsant  A drug used to prevent seizures or reduce their severity.
cardioprotective agent  Any protective agent that is able to prevent damage to the heart.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
zofenoprilKEGG DRUG
zofenoprilumChemIDplus
zofenoprilWHO MedNet
zofénoprilWHO MedNet
Manual XrefsDatabases
D08688KEGG DRUG
ZofenoprilWikipedia
2866DrugCentral
Registry NumbersSources
Reaxys:6443047Reaxys
CAS:81872-10-8KEGG DRUG
CAS:81872-10-8ChemIDplus
Citations