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Record Information
Version3.6
Creation Date2013-07-22 19:52:47 UTC
Update Date2016-02-11 08:19:51 UTC
HMDB IDHMDB61178
Secondary Accession NumbersNone
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=1/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-/s2
InChI KeyInChIKey=AKUCMKAPHCGRFV-LSLYOTEVNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid esters
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • Phenylpropylamine
  • Indole or derivatives
  • 2,5-dioxopiperazine
  • Dioxopiperazine
  • N-alkylpiperazine
  • Fatty acid ester
  • Fatty acyl
  • Benzenoid
  • Piperazine
  • 1,4-diazinane
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Tertiary amine
  • Lactam
  • Carboxylic acid ester
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • 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
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity112.71 m3·mol-1ChemAxon
Polarizability46.32 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB61178
Metagene LinkHMDB61178
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