Benazeprilat (CHEM043943)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:28:02 UTC
Update Date2016-11-09 01:23:01 UTC
Accession NumberCHEM043943
Identification
Common NameBenazeprilat
ClassSmall Molecule
DescriptionA benzazepine that is 1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in which the hydrogen attached to the nitrogen is replaced by a carboxy methyl group and in which the 3-pro-S hydrogen is replaced by the amino group of (2S)-2-amino-4-phenylbutanoic acid. An angiotensin-converting enzyme inhibitor, it is used as its monoester prodrug benazepril in the treatment of hypertension and heart failure.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass396.436 g/mol
Monoisotopic Mass396.169 g/mol
CAS Registry Number86541-78-8
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
SMILESOC(=O)CN1C2=CC=CC=C2CC[C@H](N[C@@H](CCC2=CC=CC=C2)C(O)=O)C1=O
InChI IdentifierInChI=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
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 Solubility0.028 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
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, Positivesplash10-0f6x-5339000000-79f0d1358b75a224dae5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-4101910000-8b1339e1a13e7ad42249Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f92-0009000000-d1319ee37edec27e1148Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-3229000000-0dc516b7bcc139e1a83dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apl-3921000000-0762176b089f4d89288bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0009000000-0cfaafdb759ca6c4922fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f9t-0129000000-fcbfafbc2f2114ad0a1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0629-2911000000-7200a52de7d82e2d1856Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-0009000000-10c2002d627e732a820cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-1000-0709000000-a5b9f077616bf86c3dc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-1911000000-7820a2391cb1f258a53eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-3efd2767e682bcb02a2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfs-0319000000-109ed32b6122065eadceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-2920000000-8250905e19b220ccd554Spectrum
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 IDHMDB0060582
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenazepril
Chemspider IDNot Available
ChEBI ID88200
PubChem Compound ID5463984
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available