Quinaprilat (CHEM043948)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:28:27 UTC
Update Date2016-11-09 01:23:01 UTC
Accession NumberCHEM043948
Identification
Common NameQuinaprilat
ClassSmall Molecule
DescriptionA dicarboxylic acid resulting from the hydrolysis of the ethyl ester group of quinapril to give the corresponding dicarboxylic acid. The active angiotensin-converting enzyme inhibitor (ACE inhibitor) of the prodrug quinapril.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CI 928ChEBI
CI-928ChEBI
CI928ChEBI
CL-928ChEBI
QuinaprilateChEBI
QuinaprilatumChEBI
Quinaprilic acidGenerator
CI-928quinaprilatHMDB
2-(2-((1-Carboxy-3-phenylpropyl)amino)-1-oxopropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acidHMDB
Quinaprilat, (3S-(2(r*(r*)),3R*))-isomerHMDB
Chemical FormulaC23H26N2O5
Average Molecular Mass410.463 g/mol
Monoisotopic Mass410.184 g/mol
CAS Registry Number82768-85-2
IUPAC Name(3S)-2-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
Traditional Namequinaprilat
SMILES[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1CC2=CC=CC=C2C[C@@]1([H])C(O)=O
InChI IdentifierInChI=1S/C23H26N2O5/c1-15(24-19(22(27)28)12-11-16-7-3-2-4-8-16)21(26)25-14-18-10-6-5-9-17(18)13-20(25)23(29)30/h2-10,15,19-20,24H,11-14H2,1H3,(H,27,28)(H,29,30)/t15-,19-,20-/m0/s1
InChI KeyFLSLEGPOVLMJMN-YSSFQJQWSA-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
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Tetrahydroisoquinoline
  • L-alpha-amino acid
  • Aralkylamine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid
  • Secondary aliphatic amine
  • Secondary amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.036 g/LALOGPS
logP0.81ALOGPS
logP0.3ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
pKa (Strongest Basic)7.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.94 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity110.44 m³·mol⁻¹ChemAxon
Polarizability42.76 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0403-2925000000-e4de4c2b1f51a90ebc34Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000i-9642440000-3935bd20baf3ed736d1dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xu-0239400000-657f7ef4a13d754d6019Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1953000000-6560d0372a2a1dd70171Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ec-2900000000-89636c81c5cbbdc3ef6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aor-0009500000-9c12c7c6c289ed26d187Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0690-0529100000-5ebce1d9aed5907f8abfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02e9-1910000000-df2dae9a4c8d21668f20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0125900000-de537442df409f3872dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0319100000-0d99754c5f3bea7a6b30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02u3-2900000000-67e4c42bed2130a5a52dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0114900000-c3d294563f563dcc6f6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-0911100000-7452d726559f5d57738aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0m0x-2910000000-ad031a0b0ef9b18dd397Spectrum
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 IDNot Available
HMDB IDHMDB0042005
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkQuinaprilat
Chemspider ID97106
ChEBI ID140296
PubChem Compound ID107994
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=11300367
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11422007
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11824807
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12698173
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12808303
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15223904
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19016233
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=19135197
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19761414
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21083190
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24175935
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=9336392
13. Kieback AG, Felix SB, Reffelmann T: Quinaprilat: a review of its pharmacokinetics, pharmacodynamics, toxicological data and clinical application. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1337-47. doi: 10.1517/17425250903282773.
14. Steinhauff S, Pehlivanli S, Bakovic-Alt R, Meiser BM, Becker BF, von Scheidt W, Weis M: Beneficial effects of quinaprilat on coronary vasomotor function, endothelial oxidative stress, and endothelin activation after human heart transplantation. Transplantation. 2004 Jun 27;77(12):1859-65. doi: 10.1097/01.tp.0000131148.78203.b7.