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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:52:41 UTC
Update Date2021-09-14 15:40:15 UTC
HMDB IDHMDB0042005
Secondary Accession Numbers
  • HMDB42005
Metabolite Identification
Common NameQuinaprilat
DescriptionQuinaprilat is the active metabolite of quinapril. Quinapril is a prodrug and is a long-acting, non-sulfhydryl angiotensin-converting enzyme (ACE) inhibitor used in the treatment of arterial hypertension or chronic heart failure (PMID: 19761414 ). Prodrugs are compounds that must be metabolized in the gut or liver before they can become active. Quinaprilat functions through blocking the conversion of angiotensin I to the vasoconstrictor angiotensin II, thereby inhibiting bradykinin degradation which reduces vascular oxidative stress and endothelial activity (PMID: 15223904 ). It is eliminated mainly in urine. It has no teratogenic, mutagenic or carcinogenic effect. Quinaprilat is only found in individuals who have taken or consumed the drug quinapril.
Structure
Data?1563863721
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 Weight410.4629
Monoisotopic Molecular Weight410.184171952
IUPAC Name(3S)-2-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
Traditional Namequinaprilat
CAS Registry Number82768-85-2
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 Identifier
InChI=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
Ontology
Disposition

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.036 g/LALOGPS
logP10(0.81) g/LALOGPS
logP10(0.3) g/LChemAxon
logS10(-4.1) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+193.60131661259
DarkChem[M-H]-189.33931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Quinaprilat[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1CC2=CC=CC=C2C[C@@]1([H])C(O)=O4863.0Standard polar33892256
Quinaprilat[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1CC2=CC=CC=C2C[C@@]1([H])C(O)=O3070.6Standard non polar33892256
Quinaprilat[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1CC2=CC=CC=C2C[C@@]1([H])C(O)=O3476.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Quinaprilat,1TMS,isomer #1C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O3284.0Semi standard non polar33892256
Quinaprilat,1TMS,isomer #2C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C3303.0Semi standard non polar33892256
Quinaprilat,1TMS,isomer #3C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C3293.6Semi standard non polar33892256
Quinaprilat,2TMS,isomer #1C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C3223.8Semi standard non polar33892256
Quinaprilat,2TMS,isomer #2C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3227.4Semi standard non polar33892256
Quinaprilat,2TMS,isomer #3C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C3211.1Semi standard non polar33892256
Quinaprilat,3TMS,isomer #1C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3223.7Semi standard non polar33892256
Quinaprilat,3TMS,isomer #1C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3210.5Standard non polar33892256
Quinaprilat,1TBDMS,isomer #1C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O3548.2Semi standard non polar33892256
Quinaprilat,1TBDMS,isomer #2C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3568.5Semi standard non polar33892256
Quinaprilat,1TBDMS,isomer #3C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C3578.0Semi standard non polar33892256
Quinaprilat,2TBDMS,isomer #1C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3721.7Semi standard non polar33892256
Quinaprilat,2TBDMS,isomer #2C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3764.8Semi standard non polar33892256
Quinaprilat,2TBDMS,isomer #3C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C3761.7Semi standard non polar33892256
Quinaprilat,3TBDMS,isomer #1C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3947.4Semi standard non polar33892256
Quinaprilat,3TBDMS,isomer #1C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3812.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Quinaprilat GC-MS (Non-derivatized) - 70eV, Positivesplash10-0403-2925000000-e4de4c2b1f51a90ebc342017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinaprilat GC-MS (2 TMS) - 70eV, Positivesplash10-000i-9642440000-3935bd20baf3ed736d1d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinaprilat GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinaprilat 10V, Positive-QTOFsplash10-03xu-0239400000-657f7ef4a13d754d60192017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinaprilat 20V, Positive-QTOFsplash10-0a4i-1953000000-6560d0372a2a1dd701712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinaprilat 40V, Positive-QTOFsplash10-03ec-2900000000-89636c81c5cbbdc3ef6d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinaprilat 10V, Negative-QTOFsplash10-0aor-0009500000-9c12c7c6c289ed26d1872017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinaprilat 20V, Negative-QTOFsplash10-0690-0529100000-5ebce1d9aed5907f8abf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinaprilat 40V, Negative-QTOFsplash10-02e9-1910000000-df2dae9a4c8d21668f202017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinaprilat 10V, Positive-QTOFsplash10-03di-0125900000-de537442df409f3872dc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinaprilat 20V, Positive-QTOFsplash10-014i-0319100000-0d99754c5f3bea7a6b302021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinaprilat 40V, Positive-QTOFsplash10-02u3-2900000000-67e4c42bed2130a5a52d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinaprilat 10V, Negative-QTOFsplash10-0a4i-0114900000-c3d294563f563dcc6f6d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinaprilat 20V, Negative-QTOFsplash10-057i-0911100000-7452d726559f5d57738a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinaprilat 40V, Negative-QTOFsplash10-0m0x-2910000000-ad031a0b0ef9b18dd3972021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID97106
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQuinaprilat
METLIN IDNot Available
PubChem Compound107994
PDB IDNot Available
ChEBI ID140296
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:19761414 ]
  2. 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. [PubMed:15223904 ]