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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:30 UTC
Update Date2017-10-23 19:06:01 UTC
HMDB IDHMDB0012235
Secondary Accession Numbers
  • HMDB12235
Metabolite Identification
Common NameHydroxybupropion
DescriptionHydroxybupropion is found in the bupropion degradation pathway. Bupropion reacts with NADPH and O2 to produce hydroxybupropion, with NADP+ and H2O as byproducts.
Structure
Thumb
Synonyms
ValueSource
4-Hydroxy bupropionMeSH
B.W.306uMeSH
BW-306UMeSH
BW 306UMeSH
BW-306-UMeSH
Chemical FormulaC13H18ClNO2
Average Molecular Weight255.741
Monoisotopic Molecular Weight255.102606532
IUPAC Name1-(3-chlorophenyl)-2-[(1-hydroxy-2-methylpropan-2-yl)amino]propan-1-one
Traditional Name1-(3-chlorophenyl)-2-[(1-hydroxy-2-methylpropan-2-yl)amino]propan-1-one
CAS Registry NumberNot Available
SMILES
CC(NC(C)(C)CO)C(=O)C1=CC(Cl)=CC=C1
InChI Identifier
InChI=1S/C13H18ClNO2/c1-9(15-13(2,3)8-16)12(17)10-5-4-6-11(14)7-10/h4-7,9,15-16H,8H2,1-3H3
InChI KeyAKOAEVOSDHIVFX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Phenylpropane
  • Benzoyl
  • Aryl alkyl ketone
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Alpha-aminoketone
  • 1,2-aminoalcohol
  • Secondary aliphatic amine
  • Secondary amine
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP1.98ALOGPS
logP2.22ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)14.79ChemAxon
pKa (Strongest Basic)7.65ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.24 m³·mol⁻¹ChemAxon
Polarizability26.74 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-000i-7920000000-be56f464d785d223b458View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-4910000000-17e69cd1da4ca8936546View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0090000000-df8d674659496b37c9bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2290000000-8f8a9ceb3a4fe0946f85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006y-9510000000-cced4d9478cbf2a8183bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-52331e78990719b9a759View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-1290000000-581579504e584625946fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07vr-5940000000-79b17466f2c269e0e451View 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 IDDBMET00277
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDFDB028878
      KNApSAcK IDNot Available
      Chemspider ID433
      KEGG Compound IDNot Available
      BioCyc IDCPD-3483
      BiGG IDNot Available
      Wikipedia LinkHydroxybupropion
      METLIN IDNot Available
      PubChem Compound446
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available