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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 17:07:22 UTC
Update Date2019-07-23 07:14:38 UTC
HMDB IDHMDB0060583
Secondary Accession Numbers
  • HMDB60583
Metabolite Identification
Common NameTrandolaprilat
DescriptionTrandolaprilat 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. It is marketed by Abbott Laboratories with the brand name Mavik. Trandolaprilat is a very strong basic compound (based on its pKa). In humans, trandolaprilat is involved in trandolapril metabolism pathway. Trandolapril is an ACE inhibitor used to treat high blood pressure, it may also be used to treat other conditions. Trandolaprilat is a metabolite of trandolapril.
Structure
Data?1563866078
Synonyms
ValueSource
1-(2-((1-Carboxy-3-phenylpropyl)amino)-1-oxopropyl)octahydro-1H-indole-2-carboxylic acidHMDB
Trandolaprilat, (2S-(1R*(r*)),2alpha,3aalpha,7abeta)-isomerHMDB
TrandolaprilateHMDB
Trandolaprilat, (2S-(1(s*(r*)),2alpha,3aalpha,7abeta))-isomerHMDB
Trandolaprilat, (2S-(1(r*(r*)),2alpha,3abeta,7abeta))-isomerHMDB
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
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
  • 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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity106.27 m³·mol⁻¹ChemAxon
Polarizability42.91 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-9527000000-a643d41bd64e07adba5aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00su-9222430000-0069ccf8184bd033698cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0k9i-0239400000-ab8bb14e56c9f83e8e16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1953000000-fdf35cfce0f13a2da0faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08ml-3910000000-249f7038306c9dfa5c02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0009500000-926c6ad77a5d3f549f5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0rl0-0519100000-4bede66895662526d830Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01b9-1900000000-99dcb0b8ac33262690fdSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound5464097
      PDB IDX93
      ChEBI IDNot Available
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available