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Record Information
Version4.0
Creation Date2012-09-06 15:00:17 UTC
Update Date2017-09-27 08:27:26 UTC
HMDB IDHMDB0013872
Secondary Accession Numbers
  • HMDB13872
Metabolite Identification
Common NameThalidomide arene oxide
DescriptionThalidomide arene oxide is a metabolic intermediate of thalidomide which subsequently converts to 5-hydroxythalidomide. It belongs to the family of Isoindolones. These are aromatic polycyclic compounds that an isolindole bearing a ketone.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC13H10N2O5
Average Molecular Weight274.2289
Monoisotopic Molecular Weight274.05897144
IUPAC Name3-{3,5-dioxo-1aH,3H,4H,5H,6aH-oxireno[2,3-f]isoindol-4-yl}piperidine-2,6-dione
Traditional Name3-{3,5-dioxo-1aH,6aH-oxireno[2,3-f]isoindol-4-yl}piperidine-2,6-dione
CAS Registry Number1488-25-1
SMILES
O=C1N(C2CCC(=O)NC2=O)C(=O)C2=CC3OC3C=C12
InChI Identifier
InChI=1S/C13H10N2O5/c16-10-2-1-7(11(17)14-10)15-12(18)5-3-8-9(20-8)4-6(5)13(15)19/h3-4,7-9H,1-2H2,(H,14,16,17)
InChI KeyMNALUCRLHVMELD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassIsoindoles and derivatives
Direct ParentIsoindolones
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Isoindolone
  • Isoindole
  • Piperidinedione
  • Delta-lactam
  • Piperidinone
  • Carboxylic acid imide, n-substituted
  • Piperidine
  • N-alkylpyrrolidine
  • 2-pyrrolidone
  • Pyrrolidone
  • Carboxylic acid imide
  • Dicarboximide
  • Carboxylic acid imide, n-unsubstituted
  • Pyrrolidine
  • Lactam
  • Ether
  • Oxirane
  • Dialkyl ether
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Industrial application:

  Pharmaceutical industry:

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 Solubility9.74 g/LALOGPS
logP-0.2ALOGPS
logP-1.4ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)11.59ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area96.08 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.8 m³·mol⁻¹ChemAxon
Polarizability25.06 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-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00035
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 References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]