Showing metabocard for Bupropion (BMDB0001510)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:46:59 UTC
Update Date2020-05-11 20:22:36 UTC
BMDB IDBMDB0001510
Secondary Accession Numbers
  • BMDB01510
Metabolite Identification
Common NameBupropion
Descriptionbupropion 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. Based on a literature review a significant number of articles have been published on bupropion.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-BupropionHMDB
AmfebutamonaHMDB
AmfebutamoneHMDB, MeSH
AmfebutamonumHMDB
WellbatrinHMDB
WellbutrinHMDB, MeSH
ZybanHMDB
Bupropion hydrochlorideMeSH, HMDB
Bupropion, (+-)-isomerMeSH, HMDB
glaxo Wellcome brand 1 OF bupropion hydrochlorideMeSH, HMDB
glaxo Wellcome brand 3 OF bupropion hydrochlorideMeSH, HMDB
Zyban (anti-smoking)MeSH, HMDB
GlaxoSmithKline brand 2 OF bupropion hydrochlorideMeSH, HMDB
(+-)-1-(3-Chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanoneMeSH, HMDB
Esteve brand OF bupropion hydrochlorideMeSH, HMDB
glaxo Wellcome brand 2 OF bupropion hydrochlorideMeSH, HMDB
Bupropion hydrochloride, (+-)-isomerMeSH, HMDB
GlaxoSmithKline brand 1 OF bupropion hydrochlorideMeSH, HMDB
QuomenMeSH, HMDB
ZyntabacMeSH, HMDB
Zyban (bupropion)MeSH, HMDB
Chemical FormulaC13H18ClNO
Average Molecular Weight239.741
Monoisotopic Molecular Weight239.10769191
IUPAC Name2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
Traditional Namebupropion
CAS Registry Number34841-39-9
SMILES
CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1
InChI Identifier
InChI=1S/C13H18ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,15H,1-4H3
InChI KeySNPPWIUOZRMYNY-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
  • Secondary aliphatic amine
  • Secondary amine
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.28ALOGPS
logP3.27ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)18.29ChemAxon
pKa (Strongest Basic)8.22ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.7 m³·mol⁻¹ChemAxon
Polarizability25.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-000l-5900000000-1b5fb2e947791614a61dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001i-0910000000-fa2592b7296c7561333cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-c10af1c8e3619fe0bffcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0490000000-55448af4d9a8ce866a88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-2883ba18321a8b8228a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0159-0900000000-7d6cad849706146ddab3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0159-0900000000-0fca8999746b69ee4fc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-b64f8d2b50bede574f63View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-2edefa63d5f6f1b08db7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0490000000-b8ea1de058a84547700dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0910000000-6f471b9150fb1b7f6fccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0159-0900000000-cc966137ee3283828af7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00lr-0900000000-7f86f38f740aa41b244bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-e7f2cfdbabbd35a9b643View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-4daf0e10db1e5f2750bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-f77a450be176593153d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00m0-0910000000-d2eb7265b058766459c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0910000000-fa2592b7296c7561333cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-0900000000-4d831e97d7e7dfff141bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-00lr-0900000000-65c6a707c92719eb037bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0290000000-f40e79f27fd0f3448f9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-2950000000-e144eddb8d64cdf24711View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9500000000-9c44a89baee334f5ce9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-f90eefcb5d4049067bbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2490000000-afd91ae0bad53e4c5c9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02mi-6930000000-94751c5f94b6dd91d63eView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Brain
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID431
KEGG Compound IDC06860
BioCyc IDCPD-3481
BiGG IDNot Available
Wikipedia LinkBupropion
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID3219
References
Synthesis ReferenceXia, Min; Xu, Bao-feng. Study on synthesis of the amfebutamone hydrochloride. Shandong Huagong (2003), 32(3), 3-5.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available