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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:30 UTC
Update Date2021-09-14 15:00:46 UTC
HMDB IDHMDB0012235
Secondary Accession Numbers
  • HMDB12235
Metabolite Identification
Common NameHydroxybupropion
DescriptionHydroxybupropion, also known as b.w.306u, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Hydroxybupropion has been detected, but not quantified in, several different foods, such as sparkleberries (Vaccinium arboreum), kai-lans (Brassica oleracea var. alboglabra), nopals (Opuntia cochenillifera), skunk currants (Ribes glandulosum), and hazelnuts (Corylus). This could make hydroxybupropion a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Hydroxybupropion.
Structure
Data?1582753031
Synonyms
ValueSource
4-Hydroxy bupropionHMDB
B.W.306uHMDB
BW-306UHMDB
BW 306UHMDB
BW-306-UHMDB
HydroxybupropionMeSH
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
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl 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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+157.26330932474
DeepCCS[M-H]-154.90530932474
DeepCCS[M-2H]-187.79430932474
DeepCCS[M+Na]+163.35630932474
AllCCS[M+H]+156.932859911
AllCCS[M+H-H2O]+153.432859911
AllCCS[M+NH4]+160.232859911
AllCCS[M+Na]+161.232859911
AllCCS[M-H]-160.232859911
AllCCS[M+Na-2H]-160.832859911
AllCCS[M+HCOO]-161.632859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hydroxybupropion,1TMS,isomer #1CC(NC(C)(C)CO[Si](C)(C)C)C(=O)C1=CC=CC(Cl)=C11933.7Semi standard non polar33892256
Hydroxybupropion,1TMS,isomer #1CC(NC(C)(C)CO[Si](C)(C)C)C(=O)C1=CC=CC(Cl)=C12033.7Standard non polar33892256
Hydroxybupropion,1TMS,isomer #1CC(NC(C)(C)CO[Si](C)(C)C)C(=O)C1=CC=CC(Cl)=C12270.1Standard polar33892256
Hydroxybupropion,1TMS,isomer #2CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)CO)[Si](C)(C)C1970.3Semi standard non polar33892256
Hydroxybupropion,1TMS,isomer #2CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)CO)[Si](C)(C)C2059.8Standard non polar33892256
Hydroxybupropion,1TMS,isomer #2CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)CO)[Si](C)(C)C2532.2Standard polar33892256
Hydroxybupropion,2TMS,isomer #1CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)CO[Si](C)(C)C)[Si](C)(C)C2042.1Semi standard non polar33892256
Hydroxybupropion,2TMS,isomer #1CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)CO[Si](C)(C)C)[Si](C)(C)C2147.4Standard non polar33892256
Hydroxybupropion,2TMS,isomer #1CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)CO[Si](C)(C)C)[Si](C)(C)C2216.8Standard polar33892256
Hydroxybupropion,1TBDMS,isomer #1CC(NC(C)(C)CO[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC(Cl)=C12168.1Semi standard non polar33892256
Hydroxybupropion,1TBDMS,isomer #1CC(NC(C)(C)CO[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC(Cl)=C12251.5Standard non polar33892256
Hydroxybupropion,1TBDMS,isomer #1CC(NC(C)(C)CO[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC(Cl)=C12408.0Standard polar33892256
Hydroxybupropion,1TBDMS,isomer #2CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)CO)[Si](C)(C)C(C)(C)C2263.3Semi standard non polar33892256
Hydroxybupropion,1TBDMS,isomer #2CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)CO)[Si](C)(C)C(C)(C)C2276.5Standard non polar33892256
Hydroxybupropion,1TBDMS,isomer #2CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)CO)[Si](C)(C)C(C)(C)C2577.0Standard polar33892256
Hydroxybupropion,2TBDMS,isomer #1CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2547.1Semi standard non polar33892256
Hydroxybupropion,2TBDMS,isomer #1CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2545.1Standard non polar33892256
Hydroxybupropion,2TBDMS,isomer #1CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2435.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxybupropion GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-7920000000-be56f464d785d223b4582017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxybupropion GC-MS (1 TMS) - 70eV, Positivesplash10-0079-4910000000-17e69cd1da4ca89365462017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxybupropion GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxybupropion 10V, Positive-QTOFsplash10-0a4r-0090000000-df8d674659496b37c9bd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxybupropion 20V, Positive-QTOFsplash10-000i-2290000000-8f8a9ceb3a4fe0946f852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxybupropion 40V, Positive-QTOFsplash10-006y-9510000000-cced4d9478cbf2a8183b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxybupropion 10V, Negative-QTOFsplash10-0udi-0090000000-52331e78990719b9a7592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxybupropion 20V, Negative-QTOFsplash10-0f79-1290000000-581579504e584625946f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxybupropion 40V, Negative-QTOFsplash10-07vr-5940000000-79b17466f2c269e0e4512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxybupropion 10V, Negative-QTOFsplash10-0udi-0090000000-04c26f716885b28d861f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxybupropion 20V, Negative-QTOFsplash10-001i-9350000000-913e15c3e3810b02e7e52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxybupropion 40V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxybupropion 10V, Positive-QTOFsplash10-0apr-0890000000-3ddcd3174aa3fe0486942021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxybupropion 20V, Positive-QTOFsplash10-014i-0900000000-2df04cfe6fb36f515c312021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxybupropion 40V, Positive-QTOFsplash10-03di-6900000000-1625be8c390576c82adc2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available