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Record Information
Version3.6
Creation Date2009-04-06 16:21:30 UTC
Update Date2016-02-11 01:24:00 UTC
HMDB IDHMDB12235
Secondary Accession NumbersNone
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
SynonymsNot Available
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 KeyInChIKey=AKOAEVOSDHIVFX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAcetophenones
Direct ParentAcetophenones
Alternative Parents
Substituents
  • Phenylpropane
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Alpha-aminoketone
  • Ketone
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.24 m3·mol-1ChemAxon
Polarizability26.74 Å3ChemAxon
Number of Rings1ChemAxon
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 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 LinkNot Available
NuGOwiki LinkHMDB12235
Metagene LinkHMDB12235
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