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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:42 UTC
HMDB IDHMDB0014682
Secondary Accession Numbers
  • HMDB14682
Metabolite Identification
Common NameBenazepril
DescriptionBenazepril, also known as benazepril sandoz or forteekor, 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. Benazepril is a very strong basic compound (based on its pKa). In humans, benazepril is involved in benazepril action pathway.
Structure
Data?1582753208
Synonyms
ValueSource
BenazeprilumChEBI
Benazepril sandozKegg
ForteekorKegg
CGS-14824-aHMDB
LotensinHMDB
BriemHMDB
CibacèneHMDB
LabopalHMDB
CibacenHMDB
BenazaprilHMDB
Benazepril hydrochlorideHMDB
BenzazeprilHMDB
Chemical FormulaC24H28N2O5
Average Molecular Weight424.4895
Monoisotopic Molecular Weight424.199822016
IUPAC Name2-[(3S)-3-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]acetic acid
Traditional Namebenazepril
CAS Registry Number86541-75-5
SMILES
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCC2=CC=CC=C2N(CC(O)=O)C1=O
InChI Identifier
InChI=1S/C24H28N2O5/c1-2-31-24(30)20(14-12-17-8-4-3-5-9-17)25-19-15-13-18-10-6-7-11-21(18)26(23(19)29)16-22(27)28/h3-11,19-20,25H,2,12-16H2,1H3,(H,27,28)/t19-,20-/m0/s1
InChI KeyXPCFTKFZXHTYIP-PMACEKPBSA-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
  • Benzazepine
  • Alpha-amino acid or derivatives
  • Azepine
  • Fatty acid ester
  • Aralkylamine
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Amino acid
  • Lactam
  • Carboxamide group
  • Carboxylic acid
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point148 - 149 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.01 g/LNot Available
LogP3.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP1.14ALOGPS
logP1.54ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)5.36ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity115.23 m³·mol⁻¹ChemAxon
Polarizability44.98 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]+196.27331661259
DarkChem[M-H]-192.13431661259
DeepCCS[M+H]+194.82430932474
DeepCCS[M-H]-192.42930932474
DeepCCS[M-2H]-225.31130932474
DeepCCS[M+Na]+200.73730932474
AllCCS[M+H]+202.432859911
AllCCS[M+H-H2O]+200.032859911
AllCCS[M+NH4]+204.532859911
AllCCS[M+Na]+205.132859911
AllCCS[M-H]-198.332859911
AllCCS[M+Na-2H]-199.032859911
AllCCS[M+HCOO]-199.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenazeprilCCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCC2=CC=CC=C2N(CC(O)=O)C1=O5217.7Standard polar33892256
BenazeprilCCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCC2=CC=CC=C2N(CC(O)=O)C1=O2555.0Standard non polar33892256
BenazeprilCCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCC2=CC=CC=C2N(CC(O)=O)C1=O3334.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benazepril,1TMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCC2=CC=CC=C2N(CC(=O)O[Si](C)(C)C)C1=O3307.7Semi standard non polar33892256
Benazepril,1TMS,isomer #2CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCC2=CC=CC=C2N(CC(=O)O)C1=O)[Si](C)(C)C3349.3Semi standard non polar33892256
Benazepril,2TMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCC2=CC=CC=C2N(CC(=O)O[Si](C)(C)C)C1=O)[Si](C)(C)C3296.1Semi standard non polar33892256
Benazepril,2TMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCC2=CC=CC=C2N(CC(=O)O[Si](C)(C)C)C1=O)[Si](C)(C)C3188.3Standard non polar33892256
Benazepril,2TMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCC2=CC=CC=C2N(CC(=O)O[Si](C)(C)C)C1=O)[Si](C)(C)C4308.9Standard polar33892256
Benazepril,1TBDMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCC2=CC=CC=C2N(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O3548.4Semi standard non polar33892256
Benazepril,1TBDMS,isomer #2CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCC2=CC=CC=C2N(CC(=O)O)C1=O)[Si](C)(C)C(C)(C)C3550.3Semi standard non polar33892256
Benazepril,2TBDMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCC2=CC=CC=C2N(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C3734.9Semi standard non polar33892256
Benazepril,2TBDMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCC2=CC=CC=C2N(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C3585.4Standard non polar33892256
Benazepril,2TBDMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCC2=CC=CC=C2N(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C4371.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benazepril GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2009000000-19c2bb5c2c0344b51b242017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benazepril GC-MS (1 TMS) - 70eV, Positivesplash10-00di-3002900000-85952764d74c570979282017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benazepril GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benazepril 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 - Benazepril , positive-QTOFsplash10-0ufu-0917700000-5f1f2ae9b1d7afc6eee52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benazepril 35V, Negative-QTOFsplash10-00di-0510900000-aef2e71e3edc278d21812021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benazepril 35V, Positive-QTOFsplash10-0ufu-0906300000-967f2d700778895024c22021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazepril 10V, Positive-QTOFsplash10-004i-0117900000-5f064fedfa50b268135b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazepril 20V, Positive-QTOFsplash10-004i-3329200000-a339e2329a1813e9c0562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazepril 40V, Positive-QTOFsplash10-05uu-2910000000-1a808fc7adec9b057f0b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazepril 10V, Negative-QTOFsplash10-00fr-1009600000-5a58d6a23289daee98012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazepril 20V, Negative-QTOFsplash10-00ba-3139300000-7836712c89121ae2cdd42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazepril 40V, Negative-QTOFsplash10-00kb-7941000000-d9aa7d72e1bd3d7292ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazepril 10V, Negative-QTOFsplash10-00di-0001900000-9d13e519742f1a70650d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazepril 20V, Negative-QTOFsplash10-00di-2449400000-8c87c62f9d64b50b65b52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazepril 40V, Negative-QTOFsplash10-0603-3982000000-8f24ae77915ed4d4bb862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazepril 10V, Positive-QTOFsplash10-004i-0004900000-245f5166b211af2a37ea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazepril 20V, Positive-QTOFsplash10-004i-0309300000-5d9f8f58556e7d05a3d92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazepril 40V, Positive-QTOFsplash10-0api-2920000000-cf196d3de0f43915f5f62021-09-22Wishart 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 DB00542 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00542 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00542
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4514935
KEGG Compound IDC06843
BioCyc IDCPD-15329
BiGG IDNot Available
Wikipedia LinkBenazepril
METLIN IDNot Available
PubChem Compound5362124
PDB IDNot Available
ChEBI ID3011
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. Hou FF, Zhang X, Zhang GH, Xie D, Chen PY, Zhang WR, Jiang JP, Liang M, Wang GB, Liu ZR, Geng RW: Efficacy and safety of benazepril for advanced chronic renal insufficiency. N Engl J Med. 2006 Jan 12;354(2):131-40. [PubMed:16407508 ]
  2. De Feo P, Torlone E, Perriello G, Fanelli C, Epifano L, Di Vincenzo A, Modarelli F, Motolese M, Brunetti P, Bolli GB: Short-term metabolic effects of the ACE-inhibitor benazepril in type 2 diabetes mellitus associated with arterial hypertension. Diabete Metab. 1992 Jul-Aug;18(4):283-8. [PubMed:1459316 ]
  3. MacNab M, Mallows S: Safety profile of benazepril in essential hypertension. Clin Cardiol. 1991 Aug;14(8 Suppl 4):IV33-7; discussion IV51-5. [PubMed:1893640 ]
  4. Gengo FM, Brady E: The pharmacokinetics of benazepril relative to other ACE inhibitors. Clin Cardiol. 1991 Aug;14(8 Suppl 4):IV44-50; discussion IV51-5. [PubMed:1893642 ]
  5. Chan KK, Buch A, Glazer RD, John VA, Barr WH: Site-differential gastrointestinal absorption of benazepril hydrochloride in healthy volunteers. Pharm Res. 1994 Mar;11(3):432-7. [PubMed:8008712 ]
  6. Szekacs B, Vajo Z, Dachman W: Effect of ACE inhibition by benazepril, enalapril and captopril on chronic and post exercise proteinuria. Acta Physiol Hung. 1996;84(4):361-7. [PubMed:9328608 ]
  7. Ishimitsu T, Akashiba A, Kameda T, Takahashi T, Ohta S, Yoshii M, Minami J, Ono H, Numabe A, Matsuoka H: Benazepril slows progression of renal dysfunction in patients with non-diabetic renal disease. Nephrology (Carlton). 2007 Jun;12(3):294-8. [PubMed:17498126 ]

Enzymes

General function:
Involved in methylenetetrahydrofolate reductase (NADPH) activity
Specific function:
Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co-substrate for homocysteine remethylation to methionine.
Gene Name:
MTHFR
Uniprot ID:
P42898
Molecular weight:
74595.895
References
  1. Jiang S, Yu Y, Venners SA, Zhang Y, Xing H, Wang X, Xu X: Effects of MTHFR and MS gene polymorphisms on baseline blood pressure and Benazepril effectiveness in Chinese hypertensive patients. J Hum Hypertens. 2011 Mar;25(3):172-7. doi: 10.1038/jhh.2010.50. Epub 2010 May 6. [PubMed:20445573 ]
  2. Jiang S, Hsu YH, Niu T, Xu X, Xing H, Chen C, Wang X, Zhang Y, Peng S, Xu X: A common haplotype on methylenetetrahydrofolate reductase gene modifies the effect of angiotensin-converting enzyme inhibitor on blood pressure in essential hypertension patients--a family-based association study. Clin Exp Hypertens. 2005 Aug;27(6):509-21. [PubMed:16081343 ]
  3. Jiang S, Hsu YH, Xu X, Xing H, Chen C, Niu T, Zhang Y, Peng S, Xu X: The C677T polymorphism of the methylenetetrahydrofolate reductase gene is associated with the level of decrease on diastolic blood pressure in essential hypertension patients treated by angiotensin-converting enzyme inhibitor. Thromb Res. 2004;113(6):361-9. [PubMed:15226090 ]
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. 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 ]