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Record Information
Version3.6
Creation Date2013-06-15 17:07:22 UTC
Update Date2017-08-18 12:44:15 UTC
HMDB IDHMDB0060583
Secondary Accession Numbers
  • HMDB60583
Metabolite Identification
Common NameTrandolaprilat
DescriptionTrandolaprilat is a metabolite of trandolapril. Trandolapril is an ACE inhibitor used to treat high blood pressure, it may also be used to treat other conditions. It is marketed by Abbott Laboratories with the brand name Mavik. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
1-(2-((1-Carboxy-3-phenylpropyl)amino)-1-oxopropyl)octahydro-1H-indole-2-carboxylic acidMeSH
Trandolaprilat, (2S-(1R*(r*)),2alpha,3aalpha,7abeta)-isomerMeSH
TrandolaprilateMeSH
Trandolaprilat, (2S-(1(s*(r*)),2alpha,3aalpha,7abeta))-isomerMeSH
Trandolaprilat, (2S-(1(r*(r*)),2alpha,3abeta,7abeta))-isomerMeSH
Chemical FormulaC22H30N2O5
Average Molecular Weight402.484
Monoisotopic Molecular Weight402.21547208
IUPAC Name(2S,3aR,7aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid
Traditional Name(2S,3aR,7aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydroindole-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
C[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1[C@H]2CCCC[C@@H]2C[C@H]1C(O)=O
InChI Identifier
InChI=1S/C22H30N2O5/c1-14(23-17(21(26)27)12-11-15-7-3-2-4-8-15)20(25)24-18-10-6-5-9-16(18)13-19(24)22(28)29/h2-4,7-8,14,16-19,23H,5-6,9-13H2,1H3,(H,26,27)(H,28,29)/t14-,16+,17-,18-,19-/m0/s1
InChI KeyAHYHTSYNOHNUSH-HXFGRODQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Indole or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary amine
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Amine
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.083 mg/mLALOGPS
logP0.77ALOGPS
logP0.19ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
pKa (Strongest Basic)8.04ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.94 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity106.27 m3·mol-1ChemAxon
Polarizability42.91 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET01014
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB0060583
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available