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CHEBI:116962 - fosinoprilat

Default Structure
ChEBI IDCHEBI:116962
ChEBI Namefosinoprilat
Stars
DefinitionA phosphinic acid-containing N-acyl derivative of (4S)-cyclohexyl-L-proline. An inhibitor of angiotensin converting enzyme (ACE), it is used as the phosphinate ester pro-drug fosinopril for treatment of hypertension and chronic heart failure.
Last Modified7 January 2015
DownloadsMolfile
FormulaC23H34NO5P
Net Charge0
Average Mass435.501
Monoisotopic Mass435.21746
SMILES[H][C@@]1(C2CCCCC2)C[C@@H](C(=O)O)N(C(=O)CP(=O)(O)CCCCc2ccccc2)C1
InChIInChI=1S/C23H34NO5P/c25-22(17-30(28,29)14-8-7-11-18-9-3-1-4-10-18)24-16-20(15-21(24)23(26)27)19-12-5-2-6-13-19/h1,3-4,9-10,19-21H,2,5-8,11-17H2,(H,26,27)(H,28,29)/t20-,21+/m1/s1
InChIKeyWOIWWYDXDVSWAZ-RTWAWAEBSA-N
Roles Classification
Biological Role:
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)
fosinoprilat (CHEBI:116962) has role antihypertensive agent (CHEBI:35674)
fosinoprilat (CHEBI:116962) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
fosinoprilat (CHEBI:116962) is a L-proline derivative (CHEBI:84186)
fosinoprilat (CHEBI:116962) is a phosphinic acids (CHEBI:26044)
Incoming Relation(s)
fosinopril (CHEBI:5163) has functional parent fosinoprilat (CHEBI:116962)
IUPAC Name 
(4S)-4-cyclohexyl-1-{[hydroxy(4-phenylbutyl)phosphoryl]acetyl}-L-proline
INNs  Source
fosinoprilatWHO MedNet
fosinoprilatWHO MedNet
fosinoprilatChemIDplus
fosinoprilatumChemIDplus
Synonyms  Source
(2S,4S)-4-cyclohexyl-1-{2-[hydroxy-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acidChEBI
(2S,4S)-4-cyclohexyl-1-{2-[hydroxy(4-phenylbutyl)phosphoryl]acetyl}pyrrolidine-2-carboxylic acidChEBI
4-Cyclohexyl-1-{2-[hydroxy-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acidChEMBL
(4S)-4-cyclohexyl-1-((hydroxy(4-phenylbutyl)phosphinyl)acetyl)-L-prolineChemIDplus
fosinopril diacidChemIDplus
fosinoprilic acidChemIDplus
Manual XrefsDatabases
D03772KEGG DRUG
Registry NumbersSources
Reaxys:6492772Reaxys
CAS:95399-71-6ChemIDplus
CAS:95399-71-6KEGG DRUG
Citations