RAMIPRIL

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Synonyms
Status
Molecule Category Free-form
ATC C09AA05
UNII L35JN3I7SJ
EPA CompTox DTXSID8023551

Structure

InChI Key HDACQVRGBOVJII-JBDAPHQKSA-N
Smiles CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]21
InChI
InChI=1S/C23H32N2O5/c1-3-30-23(29)18(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-19-11-7-10-17(19)14-20(25)22(27)28/h4-6,8-9,15,17-20,24H,3,7,10-14H2,1-2H3,(H,27,28)/t15-,17-,18-,19-,20-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H32N2O5
Molecular Weight 416.52
AlogP 2.38
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 9.0
Polar Surface Area 95.94
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 30.0

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
- 253-253 - - -
Assay Description Organism Bioactivity Reference
Inhibitory activity against angiotensin I converting enzyme (ACE) None 4.0 nM
Inhibition of rabbit lung ACE assessed as hydrolysis of hippuryl-histidyl-leucine to hippuric acid and histidyl-leucine after 30 mins Oryctolagus cuniculus 253.0 nM
Inhibition of rabbit lung ACE assessed as hippuryl-histidyl-leucine hydrolysis after 30 mins by colorimetric method Oryctolagus cuniculus 253.0 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 17.44 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 1.83 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 20.74 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 53.62 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 26.7 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 1.9 %
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 -1.7 %
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 1.34 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 7.53 %
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 -0.08 % 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 -0.08 %
Inhibition of ACE (unknown origin) Homo sapiens 25.12 nM

Environmental Exposure

Environmental Exposure Map
Countries
Slovenia

Cross References

Resources Reference
ChEBI 8774
ChEMBL CHEMBL1168
DrugBank DB00178
DrugCentral 2356
FDA SRS L35JN3I7SJ
Human Metabolome Database HMDB0014324
Guide to Pharmacology 6339
PharmGKB PA451223
SureChEMBL SCHEMBL16059
ZINC ZINC000003798757
CONTENTS