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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 17:07:18 UTC
Update Date2021-09-14 14:59:04 UTC
HMDB IDHMDB0060582
Secondary Accession Numbers
  • HMDB60582
Metabolite Identification
Common NameBenazeprilat
DescriptionBenazeprilat, also known as benazepril diacid or CGS 14831, 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. Benazeprilat is a very strong basic compound (based on its pKa). Upon cleavage of its ester group by the liver, benazepril is converted into its active form benazeprilat, a non-sulfhydryl angiotensin-converting enzyme (ACE) inhibitor. In humans, benazeprilat is involved in benazepril metabolism pathway. Benazeprilat is a metabolite of benazepril. Benazepril, brand name Lotensin, is a medication used to treat high blood pressure, congestive heart failure, and chronic renal failure.
Structure
Data?1563866078
Synonyms
ValueSource
(3S)-3-(((1S)-1-Carboxy-3-phenylpropyl)amino)-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acidChEBI
Benazepril diacidChEBI
BenazeprilateChEBI
BenazeprilatumChEBI
CGS 14831ChEBI
(3S)-3-(((1S)-1-Carboxy-3-phenylpropyl)amino)-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetateGenerator
Benazeprilic acidGenerator
BenezaprilatHMDB
Chemical FormulaC22H24N2O5
Average Molecular Weight396.4364
Monoisotopic Molecular Weight396.168521888
IUPAC Name(2S)-2-{[(3S)-1-(carboxymethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-4-phenylbutanoic acid
Traditional Namebenazeprilat
CAS Registry NumberNot Available
SMILES
OC(=O)CN1C2=CC=CC=C2CC[C@H](N[C@@H](CCC2=CC=CC=C2)C(O)=O)C1=O
InChI Identifier
InChI=1S/C22H24N2O5/c25-20(26)14-24-19-9-5-4-8-16(19)11-13-17(21(24)27)23-18(22(28)29)12-10-15-6-2-1-3-7-15/h1-9,17-18,23H,10-14H2,(H,25,26)(H,28,29)/t17-,18-/m0/s1
InChI KeyMADRIHWFJGRSBP-ROUUACIJSA-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
  • Benzazepine
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Azepine
  • Aralkylamine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Amino acid
  • Amino acid or derivatives
  • Lactam
  • Carboxamide group
  • Organoheterocyclic compound
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

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 Solubility0.028 g/LALOGPS
logP0.62ALOGPS
logP0.15ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.08ChemAxon
pKa (Strongest Basic)7.96ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.94 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity105.71 m³·mol⁻¹ChemAxon
Polarizability41.41 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]+192.42531661259
DarkChem[M-H]-187.13831661259
DeepCCS[M+H]+186.78330932474
DeepCCS[M-H]-184.42530932474
DeepCCS[M-2H]-217.7330932474
DeepCCS[M+Na]+192.95930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenazeprilatOC(=O)CN1C2=CC=CC=C2CC[C@H](N[C@@H](CCC2=CC=CC=C2)C(O)=O)C1=O5270.8Standard polar33892256
BenazeprilatOC(=O)CN1C2=CC=CC=C2CC[C@H](N[C@@H](CCC2=CC=CC=C2)C(O)=O)C1=O2520.8Standard non polar33892256
BenazeprilatOC(=O)CN1C2=CC=CC=C2CC[C@H](N[C@@H](CCC2=CC=CC=C2)C(O)=O)C1=O3422.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benazeprilat,1TMS,isomer #1C[Si](C)(C)OC(=O)CN1C(=O)[C@@H](N[C@@H](CCC2=CC=CC=C2)C(=O)O)CCC2=CC=CC=C213294.0Semi standard non polar33892256
Benazeprilat,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCC2=CC=CC=C2N(CC(=O)O)C1=O3248.1Semi standard non polar33892256
Benazeprilat,1TMS,isomer #3C[Si](C)(C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[C@H]1CCC2=CC=CC=C2N(CC(=O)O)C1=O3337.1Semi standard non polar33892256
Benazeprilat,2TMS,isomer #1C[Si](C)(C)OC(=O)CN1C(=O)[C@@H](N[C@@H](CCC2=CC=CC=C2)C(=O)O[Si](C)(C)C)CCC2=CC=CC=C213189.0Semi standard non polar33892256
Benazeprilat,2TMS,isomer #2C[Si](C)(C)OC(=O)CN1C(=O)[C@@H](N([C@@H](CCC2=CC=CC=C2)C(=O)O)[Si](C)(C)C)CCC2=CC=CC=C213252.2Semi standard non polar33892256
Benazeprilat,2TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCC2=CC=CC=C2N(CC(=O)O)C1=O)[Si](C)(C)C3255.8Semi standard non polar33892256
Benazeprilat,3TMS,isomer #1C[Si](C)(C)OC(=O)CN1C(=O)[C@@H](N([C@@H](CCC2=CC=CC=C2)C(=O)O[Si](C)(C)C)[Si](C)(C)C)CCC2=CC=CC=C213230.4Semi standard non polar33892256
Benazeprilat,3TMS,isomer #1C[Si](C)(C)OC(=O)CN1C(=O)[C@@H](N([C@@H](CCC2=CC=CC=C2)C(=O)O[Si](C)(C)C)[Si](C)(C)C)CCC2=CC=CC=C213195.5Standard non polar33892256
Benazeprilat,3TMS,isomer #1C[Si](C)(C)OC(=O)CN1C(=O)[C@@H](N([C@@H](CCC2=CC=CC=C2)C(=O)O[Si](C)(C)C)[Si](C)(C)C)CCC2=CC=CC=C214053.5Standard polar33892256
Benazeprilat,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN1C(=O)[C@@H](N[C@@H](CCC2=CC=CC=C2)C(=O)O)CCC2=CC=CC=C213561.2Semi standard non polar33892256
Benazeprilat,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCC2=CC=CC=C2N(CC(=O)O)C1=O3516.5Semi standard non polar33892256
Benazeprilat,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[C@H]1CCC2=CC=CC=C2N(CC(=O)O)C1=O3557.4Semi standard non polar33892256
Benazeprilat,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN1C(=O)[C@@H](N[C@@H](CCC2=CC=CC=C2)C(=O)O[Si](C)(C)C(C)(C)C)CCC2=CC=CC=C213667.4Semi standard non polar33892256
Benazeprilat,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CN1C(=O)[C@@H](N([C@@H](CCC2=CC=CC=C2)C(=O)O)[Si](C)(C)C(C)(C)C)CCC2=CC=CC=C213737.6Semi standard non polar33892256
Benazeprilat,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=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)C3719.5Semi standard non polar33892256
Benazeprilat,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN1C(=O)[C@@H](N([C@@H](CCC2=CC=CC=C2)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCC2=CC=CC=C213904.3Semi standard non polar33892256
Benazeprilat,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN1C(=O)[C@@H](N([C@@H](CCC2=CC=CC=C2)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCC2=CC=CC=C213800.5Standard non polar33892256
Benazeprilat,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN1C(=O)[C@@H](N([C@@H](CCC2=CC=CC=C2)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCC2=CC=CC=C214189.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benazeprilat GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-5339000000-79f0d1358b75a224dae52017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benazeprilat GC-MS (2 TMS) - 70eV, Positivesplash10-00di-4101910000-8b1339e1a13e7ad422492017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benazeprilat 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 - Benazeprilat 10V, Positive-QTOFsplash10-0f92-0009000000-d1319ee37edec27e11482017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazeprilat 20V, Positive-QTOFsplash10-0zfr-3229000000-0dc516b7bcc139e1a83d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazeprilat 40V, Positive-QTOFsplash10-0apl-3921000000-0762176b089f4d89288b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazeprilat 10V, Negative-QTOFsplash10-0f6t-0009000000-0cfaafdb759ca6c4922f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazeprilat 20V, Negative-QTOFsplash10-0f9t-0129000000-fcbfafbc2f2114ad0a1f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazeprilat 40V, Negative-QTOFsplash10-0629-2911000000-7200a52de7d82e2d18562017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazeprilat 10V, Positive-QTOFsplash10-0f6t-0009000000-10c2002d627e732a820c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazeprilat 20V, Positive-QTOFsplash10-1000-0709000000-a5b9f077616bf86c3dc42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazeprilat 40V, Positive-QTOFsplash10-01bc-1911000000-7820a2391cb1f258a53e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazeprilat 10V, Negative-QTOFsplash10-0002-0009000000-3efd2767e682bcb02a2c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazeprilat 20V, Negative-QTOFsplash10-0zfs-0319000000-109ed32b6122065eadce2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benazeprilat 40V, Negative-QTOFsplash10-05fu-2920000000-8250905e19b220ccd5542021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenazepril
METLIN IDNot Available
PubChem Compound5463984
PDB IDNot Available
ChEBI ID88200
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 ReferencesNot Available