Quinapril hydrochloride (CHEM016407)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:30:37 UTC
Update Date2016-11-09 01:15:23 UTC
Accession NumberCHEM016407
Identification
Common NameQuinapril hydrochloride
ClassSmall Molecule
DescriptionA hydrochloride resulting from the reaction of equimolar amounts of quinapril and hydrogen chloride. A prodrug for quinaprilat hydrochloride (by hydrolysis of the ethyl ester to the corresponding carboxylic acid), it is used as an angiotensin-converting enzyme inhibitor (ACE inhibitor) for the treatment of hypertension and congestive heart failure.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AccuprilChEBI
AccuprinChEBI
AccuproChEBI
AcequinChEBI
AcuitelChEBI
CI-906ChEBI
HemokvinChEBI
KorecChEBI
QuinazilChEBI
2-(2-((1-(Ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acidMeSH
QuinaprilMeSH
Chemical FormulaC25H31ClN2O5
Average Molecular Mass474.977 g/mol
Monoisotopic Mass474.192 g/mol
CAS Registry Number82586-55-8
IUPAC Name(3S)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride
Traditional Namequinapril hydrochloride
SMILESCl.[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(=O)OCC)C(=O)N1CC2=CC=CC=C2C[C@@]1([H])C(O)=O
InChI IdentifierInChI=1S/C25H30N2O5.ClH/c1-3-32-25(31)21(14-13-18-9-5-4-6-10-18)26-17(2)23(28)27-16-20-12-8-7-11-19(20)15-22(27)24(29)30;/h4-12,17,21-22,26H,3,13-16H2,1-2H3,(H,29,30);1H/t17-,21-,22-;/m0./s1
InChI KeyIBBLRJGOOANPTQ-JKVLGAQCSA-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
  • Tetrahydroisoquinoline
  • Fatty acid ester
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Tertiary carboxylic acid amide
  • Carboxylic acid ester
  • Carboxamide group
  • Amino acid
  • Amino acid or derivatives
  • Azacycle
  • Carboxylic acid
  • Secondary aliphatic amine
  • Organoheterocyclic compound
  • Secondary amine
  • Organic oxygen compound
  • Hydrochloride
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxide
  • 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
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 Solubility0.0085 g/LALOGPS
logP1.4ALOGPS
logP1.96ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)3.7ChemAxon
pKa (Strongest Basic)5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity119.96 m³·mol⁻¹ChemAxon
Polarizability47.33 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00lr-3931000000-18202ea00114e0253b97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000900000-4e399fc5bc8dd3464450Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000900000-4e399fc5bc8dd3464450Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0000900000-4e399fc5bc8dd3464450Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-fc63a21122b8e66b8135Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0000900000-fc63a21122b8e66b8135Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0000900000-fc63a21122b8e66b8135Spectrum
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 IDDBSALT000465
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkQuinapril
Chemspider IDNot Available
ChEBI ID8714
PubChem Compound ID54891
Kegg Compound IDC07340
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12749406
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16193811
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24081473
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=29310224
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=8959644