You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2013-07-22 19:52:47 UTC
Update Date2017-09-27 08:44:03 UTC
HMDB IDHMDB0061178
Secondary Accession Numbers
  • HMDB61178
Metabolite Identification
Common NameTrandolapril-d5 Diketopiperazine
DescriptionTrandolapril-d5 Diketopiperazine 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
SynonymsNot Available
Chemical FormulaC24H32N2O4
Average Molecular Weight412.5219
Monoisotopic Molecular Weight412.236207522
IUPAC Nameethyl (2R)-2-[(3S,5aS,9aR,10aS)-3-methyl-1,4-dioxo-dodecahydropiperazino[1,2-a]indol-2-yl]-4-phenylbutanoate
Traditional Nameethyl (2R)-2-[(3S,5aS,9aR,10aS)-3-methyl-1,4-dioxo-octahydro-3H-piperazino[1,2-a]indol-2-yl]-4-phenylbutanoate
CAS Registry NumberNot Available
SMILES
[H][C@@]12C[C@]3([H])N(C(=O)[C@H](C)N([C@H](CCC4=CC=CC=C4)C(=O)OCC)C3=O)[C@@]1([H])CCCC2
InChI Identifier
InChI=1S/C24H32N2O4/c1-3-30-24(29)20(14-13-17-9-5-4-6-10-17)25-16(2)22(27)26-19-12-8-7-11-18(19)15-21(26)23(25)28/h4-6,9-10,16,18-21H,3,7-8,11-15H2,1-2H3/t16-,18+,19-,20+,21-/m0/s1
InChI KeyAKUCMKAPHCGRFV-OSTWSGHESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAlpha amino acid esters
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • Indole or derivatives
  • Dioxopiperazine
  • 2,5-dioxopiperazine
  • Fatty acid ester
  • N-alkylpiperazine
  • Monocyclic benzene moiety
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • Fatty acyl
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Carboxamide group
  • Lactam
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

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 Solubility0.091 g/LALOGPS
logP2.97ALOGPS
logP3.36ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)19.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.92 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity112.71 m³·mol⁻¹ChemAxon
Polarizability46.32 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00nf-9807000000-75db03bb966150a9dfbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0003900000-33bb7d7761b6aa0e20d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3339100000-d1d882cce077dd869bceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00e9-9811000000-150f94604cea84202cf2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-1108900000-44aeef12fe21c4f7feb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-044s-4694200000-8ee33fd2700ef38bc4f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fdy-8940000000-5a01020b837b063d6d6aView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDDBMET00840
      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
      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