ENALAPRILAT

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Trade Names
Synonyms
Status
Molecule Category Mixture
UNII GV0O7ES0R3

Structure

InChI Key LZFZMUMEGBBDTC-QEJZJMRPSA-N
Smiles C[C@H](N[C@@H](CCc1ccccc1)C(=O)O)C(=O)N1CCC[C@H]1C(=O)O
InChI
InChI=1S/C18H24N2O5/c1-12(16(21)20-11-5-8-15(20)18(24)25)19-14(17(22)23)10-9-13-6-3-2-4-7-13/h2-4,6-7,12,14-15,19H,5,8-11H2,1H3,(H,22,23)(H,24,25)/t12-,14-,15-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H28N2O7
Molecular Weight 384.43
AlogP 1.13
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 8.0
Polar Surface Area 106.94
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 25.0

Bioactivity

Mechanism of Action Action Reference
Angiotensin-converting enzyme inhibitor INHIBITOR FDA
Protein: Angiotensin-converting enzyme
Description: Angiotensin-converting enzyme
Organism : Homo sapiens
P12821 ENSG00000159640
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Metallo protease Metallo protease MAE clan Metallo protease M2 family
- 1-3100 - 1 74
Assay Description Organism Bioactivity Reference
Inhibition of Angiotensin I converting enzyme from pig renal cortex, hippuryl-histidyl-leucine as substrate Sus scrofa 2.9 nM
In vitro inhibition of angiotensin I converting enzyme in rabbit lung with hippuryl-histidyl-leucine as substrate Oryctolagus cuniculus 4.3 nM
Evaluation of in vitro inhibitory activity against Angiotensin I converting enzyme Oryctolagus cuniculus 8.8 nM
In vitro activity against angiotensin I converting enzyme especially against Hip-His-Leu residues Oryctolagus cuniculus 1.2 nM
Inhibitory activity against rabbit lung Angiotensin I converting enzyme with 5 mM hippuryl-histidyl-leucine as substrate Oryctolagus cuniculus 5.7 nM
Inhibitory activity against rabbit lung angiotensin-1 converting enzyme Oryctolagus cuniculus 1.4 nM
Concentration required for 50% inhibition of rabbit lung Angiotensin I converting enzyme with 5 mM hippuryl-histidyl-leucine as substrate Oryctolagus cuniculus 5.7 nM
In vitro inhibition of Angiotensin I converting enzyme in rabbit lung Oryctolagus cuniculus 5.8 nM
In vivo inhibition of Angiotensin I converting enzyme in rabbit lung after (po) administration of a dose of 10(mg/kg) Oryctolagus cuniculus 74.0 %
In vitro inhibitory activity against angiotensin I converting enzyme of rats. None 4.0 nM
Compound was tested for inhibitory activity against angiotensin I converting enzyme None 0.95 nM
Inhibition of rat Angiotensin I converting enzyme (ACE), using Hip-Gly-Gly as synthetic substrate. None 2.3 nM
Binding affinity towards Angiotensin I converting enzyme of rat brain IgG immobilized enzyme. None 0.5 nM
Inhibition of angiotensin I converting enzyme in silico None 3.981 nM
In vitro inhibitory activity against Angiotensin I converting enzyme None 1.2 nM
Compound tested in vitro for inhibition of Angiotensin I converting enzyme None 2.6 nM
Compound was tested for its inhibitory potency against angiotensin I converting enzyme. None 3.1 nM
Inhibitory concentration against Angiotensin I converting enzyme None 1.2 nM
Inhibition of Angiotensin I converting enzyme None 1.2 nM
Inhibition of Angiotensin I converting enzyme (ACE) in Bothrops jararaca venom Bothrops jararaca 1.2 nM
Inhibition of guinea pig angiotensin I converting enzyme Cavia porcellus 2.4 nM
In vitro inhibition of Angiotensin I converting enzyme in Hog plasma Sus scrofa 1.2 nM
% Inhibition of angiotensin-I induced pressor response in normotensive rats after intravenous dosing of 0.015 umol/kg Rattus norvegicus 11.0 %
% Inhibition of angiotensin-I induced pressor response in normotensive rats after intravenous dosing of 0.05 umol/kg Rattus norvegicus 67.0 %
% Inhibition of angiotensin-I induced pressor response in normotensive rats after intravenous dosing of 0.15 umol/kg Rattus norvegicus 90.0 %
% Inhibition of angiotensin-I induced pressor response in normotensive rats after peroral dosing of 15 umol/kg Rattus norvegicus 85.0 %
% Inhibition of angiotensin-I induced pressor response in normotensive rats after peroral dosing of 5 umol/kg Rattus norvegicus 46.0 %
Maximum inhibitory effect on Angiotensin I induced pressor responses in anesthetized normotensive rats with 10 ug/kg dose of compound given intravenously Rattus norvegicus 54.5 %
Inhibition of Wistar rat plasma ACE Rattus norvegicus 9.6 nM
Inhibition of ob/ob mouse plasma ACE Mus musculus 11.5 nM
Inhibition of human plasma ACE Homo sapiens 2.5 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus -5.3 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 7.09 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 8.45 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 3.43 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 11.14 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 2.99 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 1.01 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -5.15 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 28.52 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 4.921 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.05 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.03 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.03 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.05 %

Cross References

Resources Reference
ChEBI 59877
ChEMBL CHEMBL3989406
FDA SRS GV0O7ES0R3
Guide to Pharmacology 6332
KEGG C11720
PDB EAL
PubChem 6917719
SureChEMBL SCHEMBL37288
ZINC ZINC03812851
ChEBI 4786
ChEMBL CHEMBL577
DrugBank DB09477
DrugCentral 1006
FDA SRS Q508Q118JM
Human Metabolome Database HMDB0041886
Guide to Pharmacology 6332
KEGG C11720
PDB EAL
PubChem 6917719
SureChEMBL SCHEMBL37289
ZINC ZINC000003812851
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