Ramipril (CED0002565)

Record Information
Version1.0
Creation Date2016-05-22 03:45:47 UTC
Update Date2026-05-14 16:24:30 UTC
Accession NumberCHEM016861
Identification
Common NameRamipril
ClassSmall Molecule
Description
Ramipril is an organic compound with the formula C23H32N2O5 and an average molecular weight of 416.51 g/mol. Ramipril belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound is found in or released from two recorded sources: healthcare, pharmaceuticals & veterinary products, specifically as lipid modifying agents and ACE inhibitors. The recorded route of exposure is oral. Regarding its biological activity, ramipril interacts with two recorded protein targets, acting as an activator or inhibitor of the B1 bradykinin receptor (BDKRB1) and the angiotensin-converting enzyme (ACE).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S-(1(R*(r*)),2alpha,3abeta,6abeta))-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acidChEBI
AltaceChEBI
RamiprilumChEBI
TritaceChEBI
(2S-(1(R*(r*)),2a,3abeta,6abeta))-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylateGenerator
(2S-(1(R*(r*)),2a,3abeta,6abeta))-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acidGenerator
(2S-(1(R*(r*)),2alpha,3abeta,6abeta))-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylateGenerator
(2S-(1(R*(r*)),2α,3abeta,6abeta))-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylateGenerator
(2S-(1(R*(r*)),2α,3abeta,6abeta))-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acidGenerator
Almirall brand OF ramiprilHMDB
DelixHMDB
Hoechst brand OF ramiprilHMDB
Monarch brand OF ramiprilHMDB
ZabienHMDB
Aventis brand OF ramiprilHMDB
CaraselHMDB
HOE 498HMDB
HOE-498HMDB
TriatecHMDB
VesdilHMDB
Astra brand OF ramiprilHMDB
Promed brand OF ramiprilHMDB
AcovilHMDB
AstraZeneca brand OF ramiprilHMDB
Aventis pharma brand OF ramiprilHMDB
RamaceHMDB
Chemical FormulaC23H32N2O5
Average Molecular Mass416.511 g/mol
Monoisotopic Mass416.231 g/mol
CAS Registry Number87333-19-5
IUPAC Name(2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid
Traditional Nameramipril
SMILES[H][C@@]12CCC[C@]1([H])N([C@@H](C2)C(O)=O)C(=O)[C@H](C)N[C@@H](CCC1=CC=CC=C1)C(=O)OCC
InChI IdentifierInChI=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
InChI KeyHDACQVRGBOVJII-JBDAPHQKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Alpha-amino acid ester
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • N-acylpyrrolidine
  • Fatty acid ester
  • Aralkylamine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Fatty acyl
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid ester
  • Amino acid
  • Azacycle
  • Secondary aliphatic amine
  • Carboxylic acid
  • Organoheterocyclic compound
  • Secondary amine
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP0.92ALOGPS
logP1.47ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity111.19 m³·mol⁻¹ChemAxon
Polarizability44.78 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001i-9154000000-0fd268c0fd4553ce3ab0Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-014i-5111900000-7df272465d895b3cfd2bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-1897100000-b1c2f0fcf086f6260572Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-02ai-3951000000-05bdaffd016f2d5b5d42Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lr-3930000000-ea57777ac9a14b1e9083Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0300900000-971088f84d244b7183feNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0792400000-eb2eba23ddd5b9b9b1ceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0568900000-ddc98c0a9a0a339f0dd2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-053u-3982000000-245405250f246de18bfaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06r6-3910000000-a34aa1853535d9227376Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-1019400000-6df2aca7d66607a7a4e1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0i91-2529100000-4d27b82aeecd981101c1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udj-3911000000-0756695a4b95e60fd11cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014l-0339700000-452e8e2b82c270cd994fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-1978200000-050e9a36f1e4e960836aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-066u-5911000000-74a534a7b59ef1f2a03cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009700000-a71f2ed8451e5e6d162aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-016r-1889000000-8f9e12a4e55869c7da6fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-2931000000-820a55e837269565502bNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
5155.0Log mg/kg[2900:9200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
295ACE inhibitorsHealthcare, pharmaceuticals & veterinary productsNot Available
298Lipid modifying agentsHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
4 pathways
Ramipril Action Pathway
Ramipril Action Pathway
Ramipril Metabolism Pathway
Ramipril Metabolism Pathway
Ramipril ACE Inhibitor Action Pathway
Ramipril ACE Inhibitor Action Pathway
Ramipril Drug Metabolism Action Pathway
Ramipril Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Angiotensin-converting enzyme structureClick to view 3D structureAngiotensin-converting enzymeP12821HumansPredicted (SEA)0.700643
Click to view 3D structureAngiotensin-converting enzymeP47820Rattus norvegicusPredicted (SEA)0.778492
Click to view 3D structureAngiotensin-converting enzymeP12822Oryctolagus cuniculusPredicted (SEA)2.33548
Click to view 3D structureAngiotensin-converting enzyme 2Q5EGZ1Rattus norvegicusPredicted (SEA)0.934191
Click to view 3D structureNeprilysinP07861Rattus norvegicusPredicted (SEA)42.8949
Click to view 3D structureAngiotensin-converting enzymeP09470Mus musculusPredicted (SEA)4.98235
Click to view 3D structureNeprilysinP08049Oryctolagus cuniculusPredicted (SEA)77.5378
Renin structureClick to view 3D structureReninP00797HumansPredicted (SEA)122.145
Procathepsin L structureClick to view 3D structureProcathepsin LP07711HumansPredicted (SEA)224.284
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)161.771
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)252.231
Neprilysin structureClick to view 3D structureNeprilysinP08473HumansPredicted (SEA)101.36
Click to view 3D structureFK506 binding protein 12Q8QGU2Gallus gallusPredicted (SEA)6.69503
Cathepsin B structureClick to view 3D structureCathepsin BP07858HumansPredicted (SEA)232.458
Click to view 3D structureRhodesainQ95PM0Trypanosoma brucei rhodesiensePredicted (SEA)51.5362
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)1683.65
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)700.721
Click to view 3D structureSynaptic vesicular amine transporterQ01827Rattus norvegicusPredicted (SEA)18.9952
Click to view 3D structureTryptaseP27435Rattus norvegicusPredicted (SEA)13.3122
Click to view 3D structureTryptaseP15944Canis lupus familiarisPredicted (SEA)13.3122
Cruzipain structureClick to view 3D structureCruzipainP25779Trypanosoma cruziPredicted (SEA)114.361
Click to view 3D structureMu-type opioid receptorP33535Rattus norvegicusPredicted (SEA)414.703
Click to view 3D structureProlyl endopeptidaseP23687Sus scrofaPredicted (SEA)35.3435
Xaa-Pro aminopeptidase 1 structureClick to view 3D structureXaa-Pro aminopeptidase 1Q9NQW7HumansPredicted (SEA)55.5843
Delta-type opioid receptor structureClick to view 3D structureDelta-type opioid receptorP41143HumansPredicted (SEA)631.201
Concentrations
Not Available
External Links
DrugBank IDDB00178
HMDB IDHMDB0014324
FooDB IDFDB009079
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRamipril
Chemspider ID4514937
ChEBI ID8774
PubChem Compound ID5362129
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Cacciapuoti F, Capasso A, Mirra G, De Nicola A, Minicucci F, Gentile S: Prevention of left ventricular hypertrophy by ACE-inhibitor, ramipril in comparison with calcium-channel antagonist, felodipine. Int J Cardiol. 1998 Jan 31;63(2):175-8.
2. Kleinert S: HOPE for cardiovascular disease prevention with ACE-inhibitor ramipril. Heart Outcomes Prevention Evaluation. Lancet. 1999 Sep 4;354(9181):841.
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6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12768220
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15110900
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16144510
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16734081
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=17004100
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17192135
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=17496463
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=17903031
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=20122169
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22799880
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23557551
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23713675
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23747952
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23842688
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23842829
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23951921
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=24048485
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=24090393
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=24191305
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=24397981
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=24435506
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=24452090
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=24509355