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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:49 UTC
HMDB IDHMDB0015019
Secondary Accession Numbers
  • HMDB15019
Metabolite Identification
Common NameQuinapril
DescriptionQuinapril, also known as accupril, 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. Quinapril is a very strong basic compound (based on its pKa). Quinapril inhibits angiotensin converting enzyme, an enzyme which catalyses the formation of angiotensin II from its precursor, angiotensin I. Angiotensin II is a powerful vasoconstrictor and increases blood pressure through a variety of mechanisms. In humans, quinapril is involved in quinapril action pathway. Use in pregnancy and breastfeeding is not recommended. Quinapril is a potentially toxic compound. In 2016 it was the 208th most prescribed medication in the United States with more than 2 million prescriptions. It is an ACE inhibitor and works by decreasing renin-angiotensin-aldosterone system activity. Due to reduced angiotensin production, plasma concentrations of aldosterone are also reduced, resulting in increased excretion of sodium in the urine and increased concentrations of potassium in the blood. It is available as a generic medication. In the United States the wholesale cost of this amount is about US$3.50.
Structure
Data?1582753248
Synonyms
ValueSource
(3S)-2-{N-[(2S)-1-ethoxycarbonyl-4-phenylbutan-2-yl]-L-alanyl}-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidChEBI
QuinaprilumChEBI
(3S)-2-{N-[(2S)-1-ethoxycarbonyl-4-phenylbutan-2-yl]-L-alanyl}-1,2,3,4-tetrahydroisoquinoline-3-carboxylateGenerator
AccuprilHMDB
Quinapril hydrochlorideHMDB
2-(2-((1-(Ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acidHMDB
Chemical FormulaC25H30N2O5
Average Molecular Weight438.5161
Monoisotopic Molecular Weight438.21547208
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
Traditional Namequinapril
CAS Registry Number85441-61-8
SMILES
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(O)=O
InChI Identifier
InChI=1S/C25H30N2O5/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)/t17-,21-,22-/m0/s1
InChI KeyJSDRRTOADPPCHY-HSQYWUDLSA-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
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid ester
  • Amino acid
  • Secondary aliphatic amine
  • Carboxylic acid
  • Secondary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point120 - 130 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0085 g/LNot Available
LogP3.2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0085 g/LALOGPS
logP1.39ALOGPS
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
Polarizability47.36 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]+199.10831661259
DarkChem[M-H]-195.35431661259
DeepCCS[M+H]+197.71230932474
DeepCCS[M-H]-195.31630932474
DeepCCS[M-2H]-228.230932474
DeepCCS[M+Na]+203.62430932474
AllCCS[M+H]+208.232859911
AllCCS[M+H-H2O]+206.032859911
AllCCS[M+NH4]+210.232859911
AllCCS[M+Na]+210.832859911
AllCCS[M-H]-201.632859911
AllCCS[M+Na-2H]-202.532859911
AllCCS[M+HCOO]-203.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
QuinaprilCCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(O)=O4791.8Standard polar33892256
QuinaprilCCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(O)=O2948.8Standard non polar33892256
QuinaprilCCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(O)=O3391.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Quinapril,1TMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C3316.6Semi standard non polar33892256
Quinapril,1TMS,isomer #2CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O)[Si](C)(C)C3304.9Semi standard non polar33892256
Quinapril,2TMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C)[Si](C)(C)C3286.0Semi standard non polar33892256
Quinapril,2TMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C)[Si](C)(C)C3212.8Standard non polar33892256
Quinapril,2TMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C)[Si](C)(C)C4115.1Standard polar33892256
Quinapril,1TBDMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3553.5Semi standard non polar33892256
Quinapril,1TBDMS,isomer #2CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C3554.3Semi standard non polar33892256
Quinapril,2TBDMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3747.9Semi standard non polar33892256
Quinapril,2TBDMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3619.2Standard non polar33892256
Quinapril,2TBDMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4210.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Quinapril GC-MS (1 TMS) - 70eV, Positivesplash10-000i-3121900000-0dcfc70437ccde433e9d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinapril GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-2419000000-dcbece099cf2c40cab652017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinapril GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinapril LC-ESI-qTof , Positive-QTOFsplash10-001r-0691700000-82303c3856cd6e62fe342017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinapril LC-ESI-qTof , Positive-QTOFsplash10-03di-0012900000-04b3b6ea3f77b8f1dc7f2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinapril 10V, Negative-QTOFsplash10-000f-1009500000-739119c71c43d2886da12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinapril 20V, Negative-QTOFsplash10-002g-2529200000-44c2b54cd17a4afaac8c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinapril 40V, Negative-QTOFsplash10-0032-3911000000-3b415cd9c843c9e15a8b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinapril 10V, Negative-QTOFsplash10-000i-0000900000-183d8231af4eb3b237582021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinapril 20V, Negative-QTOFsplash10-0170-1937400000-ce19e2460a1cf7114f0f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinapril 40V, Negative-QTOFsplash10-03di-0920000000-c0d6a91687c7a72591222021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinapril 10V, Positive-QTOFsplash10-000l-0344900000-464fabf7fdbf745a44ea2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinapril 20V, Positive-QTOFsplash10-001i-3893000000-a8c3960669fc104c7ad32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinapril 40V, Positive-QTOFsplash10-01po-2910000000-71a6777a3ae80c108ff82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinapril 10V, Positive-QTOFsplash10-000i-0023900000-6345f9403bef65cdcb1f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinapril 20V, Positive-QTOFsplash10-014u-0229200000-7e50a200d883930f550a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinapril 40V, Positive-QTOFsplash10-07cu-1900000000-54d41ad46f89d62881f12021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00881 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00881 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00881
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID49565
KEGG Compound IDC07398
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQuinapril
METLIN IDNot Available
PubChem Compound54892
PDB IDNot Available
ChEBI ID8713
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. Valles Prats M, Matas Serra M, Bronsoms Artero J, Mate Benito G, Torguet Escuder P, Mauri Nicolas JM: Quinapril ACE-inhibition effects on adrenergic parameters in moderate essential hypertension. Kidney Int Suppl. 1996 Jun;55:S104-6. [PubMed:8743525 ]
  2. Pitt B, O'Neill B, Feldman R, Ferrari R, Schwartz L, Mudra H, Bass T, Pepine C, Texter M, Haber H, Uprichard A, Cashin-Hemphill L, Lees RS: The QUinapril Ischemic Event Trial (QUIET): evaluation of chronic ACE inhibitor therapy in patients with ischemic heart disease and preserved left ventricular function. Am J Cardiol. 2001 May 1;87(9):1058-63. [PubMed:11348602 ]
  3. Yamada S, Muraoka I, Kato K, Hiromi Y, Takasu R, Seno H, Kawahara H, Nabeshima T: Elimination kinetics of quinaprilat and perindoprilat in hypertensive patients with renal failure on haemodialysis. Biol Pharm Bull. 2003 Jun;26(6):872-5. [PubMed:12808303 ]
  4. Tsikouris JP, Suarez JA, Meyerrose GE, Ziska M, Fike D, Smith J: Questioning a class effect: does ACE inhibitor tissue penetration influence the degree of fibrinolytic balance alteration following an acute myocardial infarction? J Clin Pharmacol. 2004 Feb;44(2):150-7. [PubMed:14747423 ]
  5. Khan BV, Sola S, Lauten WB, Natarajan R, Hooper WC, Menon RG, Lerakis S, Helmy T: Quinapril, an ACE inhibitor, reduces markers of oxidative stress in the metabolic syndrome. Diabetes Care. 2004 Jul;27(7):1712-5. [PubMed:15220251 ]
  6. Voors AA, van Geel PP, Oosterga M, Buikema H, van Veldhuisen DJ, van Gilst WH: Vascular effects of quinapril completely depend on ACE insertion/deletion polymorphism. J Renin Angiotensin Aldosterone Syst. 2004 Sep;5(3):130-4. [PubMed:15526248 ]
  7. 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 ]

Enzymes

General function:
Involved in metallopeptidase activity
Specific function:
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent vasodilator. Has also a glycosidase activity which releases GPI-anchored proteins from the membrane by cleaving the mannose linkage in the GPI moiety
Gene Name:
ACE
Uniprot ID:
P12821
Molecular weight:
149713.7
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Culy CR, Jarvis B: Quinapril: a further update of its pharmacology and therapeutic use in cardiovascular disorders. Drugs. 2002;62(2):339-85. [PubMed:11817979 ]
  3. Klutchko S, Blankley CJ, Fleming RW, Hinkley JM, Werner AE, Nordin I, Holmes A, Hoefle ML, Cohen DM, Essenburg AD, et al.: Synthesis of novel angiotensin converting enzyme inhibitor quinapril and related compounds. A divergence of structure-activity relationships for non-sulfhydryl and sulfhydryl types. J Med Chem. 1986 Oct;29(10):1953-61. [PubMed:3020249 ]
  4. Song JC, White CM: Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet. 2002;41(3):207-24. [PubMed:11929321 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular weight:
78805.3
References
  1. Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [PubMed:18713951 ]
General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular weight:
81782.8
References
  1. Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [PubMed:18713951 ]