imidapril (CHEM043743)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:13:32 UTC
Update Date2026-04-14 18:23:00 UTC
Accession NumberCHEM043743
Identification
Common Nameimidapril
ClassSmall Molecule
DescriptionA member of the class of imidazolidines that is (4S)-1-methyl-2-oxoimidazolidine-4-carboxylic acid in which the hydrogen of the imidazolidine nitrogen has been substituted by (1S)-1-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}ethyl group. It is the prodrug for imidaprilat, an ACE inhibitor used for the treatment of chronic heart failure.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(4S)-1-Methyl-3-[(2S)-2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino]propionyl]-2-oxo-imidazolidine-4-carboxylic acidChEBI
(S)-3-(N-((S)-1-Ethoxycarbonyl-3-phenylpropyl)-L-alanyl)-1-methyl-2-oxoimidazoline-4-carboxylic acidChEBI
ImidaprilumChEBI
TanatrilChEBI
HiperteneKegg
(4S)-1-Methyl-3-[(2S)-2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino]propionyl]-2-oxo-imidazolidine-4-carboxylateGenerator
(S)-3-(N-((S)-1-Ethoxycarbonyl-3-phenylpropyl)-L-alanyl)-1-methyl-2-oxoimidazoline-4-carboxylateGenerator
Imidapril hydrochlorideHMDB
1-Methyl-3-(2-(N-(1-ethoxycarbonyl-3-phenylpropyl)amino)propionyl)-2-oxoimidazolidine-4-carboxylic acidHMDB
Imidapril HCLHMDB
Chemical FormulaC20H27N3O6
Average Molecular Mass405.445 g/mol
Monoisotopic Mass405.190 g/mol
CAS Registry Number89371-37-9
IUPAC Name(4S)-3-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1-methyl-2-oxoimidazolidine-4-carboxylic acid
Traditional Nameimidapril
SMILES[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(=O)OCC)C(=O)N1C(=O)N(C)C[C@@]1([H])C(O)=O
InChI IdentifierInChI=1S/C20H27N3O6/c1-4-29-19(27)15(11-10-14-8-6-5-7-9-14)21-13(2)17(24)23-16(18(25)26)12-22(3)20(23)28/h5-9,13,15-16,21H,4,10-12H2,1-3H3,(H,25,26)/t13-,15-,16-/m0/s1
InChI KeyKLZWOWYOHUKJIG-BPUTZDHNSA-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
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-acyl urea
  • Fatty acid ester
  • Ureide
  • Aralkylamine
  • Imidazolidinone
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Fatty acyl
  • Imidazolidine
  • Dicarboximide
  • Urea
  • Amino acid or derivatives
  • Carbonic acid derivative
  • Carboxylic acid ester
  • Amino acid
  • Azacycle
  • Carboxylic acid
  • Secondary aliphatic amine
  • Organoheterocyclic compound
  • Secondary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.45 g/LALOGPS
logP0.74ALOGPS
logP-0.23ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.49ChemAxon
pKa (Strongest Basic)5.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area116.25 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity103.2 m³·mol⁻¹ChemAxon
Polarizability42.29 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01p6-9522000000-2d7e7f1a0358d64215dcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-7241900000-0ce2e92e32cdaa7af929Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1921100000-878a2227f1ea45dfbc0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000w-3941000000-cceed7dc8ced154f2113Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9510000000-08814b58975d5d6aee3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-1209400000-a27bf200103880d38895Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9406100000-86bf514aaedd86bd92d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-86c474c83f5ed25c8bc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0012900000-b9b325c5937f93151a96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f7o-8459400000-7958547e61a017dc266dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6931000000-153ce8236213e6f390bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a59-0009600000-80e4ad1d81fc56802245Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0926100000-e3d515b76c571ca4b873Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02be-4900000000-ac1c34b70720f03a911fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB11783
HMDB IDHMDB0041907
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkImidapril
Chemspider ID4576628
ChEBI ID135654
PubChem Compound ID5464343
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17094051
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20364557
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23161146
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=28044266
5.
6. Hosoya K, Ishimitsu T: Protection of the cardiovascular system by imidapril, a versatile angiotensin-converting enzyme inhibitor. Cardiovasc Drug Rev. 2002 Summer;20(2):93-110. doi: 10.1111/j.1527-3466.2002.tb00185.x.
7. Robinson DM, Curran MP, Lyseng-Williamson KA: Imidapril: a review of its use in essential hypertension, Type 1 diabetic nephropathy and chronic heart failure. Drugs. 2007;67(9):1359-78. doi: 10.2165/00003495-200767090-00008.
8. Dolezal T: Imidapril in heart failure. J Renin Angiotensin Aldosterone Syst. 2006 Sep;7(3):146-54. doi: 10.3317/jraas.2006.024.