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Showing NP-Card for Bupropion (NP0334587)

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Record Information
Version2.0
Created at2024-09-10 19:01:53 UTC
Updated at2024-09-10 19:01:54 UTC
NP-MRD IDNP0334587
Secondary Accession NumbersNone
Natural Product Identification
Common NameBupropion
DescriptionBupropion, also known as zyban or (+-)-bupropion, 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. An aromatic ketone that is propiophenone carrying a tert-butylamino group at position 2 and a chloro substituent at position 3 on the phenyl ring. Bupropion is a very strong basic compound (based on its pKa). Outside of the human body, Bupropion has been detected, but not quantified in, several different foods, such as soft-necked garlics, horseradish tree, flaxseeds, pepper (c. Baccatum), and black huckleberries. This could make bupropion a potential biomarker for the consumption of these foods. It was first documented in 1994 (PMID: 7834966). Bupropion is a potentially toxic compound (PMID: 16831112) (PMID: 14604466) (PMID: 12690637) (PMID: 11052334).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334587 (Bupropion)

1156
  Mrv0541 02231215172D          

 16 16  0  0  1  0            999 V2000
    1.6500   -2.4198    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955    2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205    0.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2 10  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
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3D MOL for NP0334587 (Bupropion)

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3D SDF for NP0334587 (Bupropion)
1156
  Mrv0541 02231215172D          

 16 16  0  0  1  0            999 V2000
    1.6500   -2.4198    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955    2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205    0.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2 10  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334587

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
SNPPWIUOZRMYNY-UHFFFAOYSA-N

> <FORMULA>
C13H18ClNO

> <MOLECULAR_WEIGHT>
239.741

> <EXACT_MASS>
239.10769191

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.925829770522174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
3.2661124519999998

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.28641838207084

> <JCHEM_PKA_STRONGEST_BASIC>
8.215779524538618

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
67.69940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bupropion

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0334587 (Bupropion)
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PDB for NP0334587 (Bupropion)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1156                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -4.517   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       4.414   0.873   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.081   2.413   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.415   3.183   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081   0.873   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.748   3.953   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.645   4.517   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.185   1.849   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415   0.103   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748   0.103   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -1.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -2.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -2.207   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -3.747   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -3.747   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -4.517   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   10                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6    7    8                                             
CONECT    5    3    9   10                                                  
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    2    5   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11   15                                                       
CONECT   14    1   12   16                                                  
CONECT   15   13   16                                                       
CONECT   16   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for NP0334587 (Bupropion)
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SMILES for NP0334587 (Bupropion)
CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1
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INCHI for NP0334587 (Bupropion)
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
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Synonyms
ValueSource
(+-)-BupropionHMDB
AmfebutamonaHMDB
AmfebutamoneHMDB
AmfebutamonumHMDB
WellbatrinHMDB
WellbutrinHMDB
ZybanHMDB
Bupropion hydrochlorideHMDB
Bupropion, (+-)-isomerHMDB
Glaxo wellcome brand 1 OF bupropion hydrochlorideHMDB
Glaxo wellcome brand 3 OF bupropion hydrochlorideHMDB
Zyban (anti-smoking)HMDB
GlaxoSmithKline brand 2 OF bupropion hydrochlorideHMDB
(+-)-1-(3-Chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanoneHMDB
Esteve brand OF bupropion hydrochlorideHMDB
Glaxo wellcome brand 2 OF bupropion hydrochlorideHMDB
Bupropion hydrochloride, (+-)-isomerHMDB
GlaxoSmithKline brand 1 OF bupropion hydrochlorideHMDB
QuomenHMDB
ZyntabacHMDB
Zyban (bupropion)HMDB
Chemical FormulaC13H18ClNO
Average Mass239.7410 Da
Monoisotopic Mass239.10769 Da
IUPAC Name2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
Traditional Namebupropion
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
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
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 RuleNoChemAxon
HMDB IDHMDB0001510  
DrugBank IDDB01156  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022664  
KNApSAcK IDNot Available
Chemspider ID431  
KEGG Compound IDC06860  
BioCyc IDCPD-3481  
BiGG IDNot Available
Wikipedia LinkBupropion  
METLIN ID1435  
PubChem Compound444  
PDB IDNot Available
ChEBI ID3219  
Good Scents IDNot Available
References
General References
  1. Mooney ME, Sofuoglu M: Bupropion for the treatment of nicotine withdrawal and craving. Expert Rev Neurother. 2006 Jul;6(7):965-81. doi: 10.1586/14737175.6.7.965. [PubMed:16831112  ] 
  2. Hesse LM, Sakai Y, Vishnuvardhan D, Li AP, von Moltke LL, Greenblatt DJ: Effect of bupropion on CYP2B6 and CYP3A4 catalytic activity, immunoreactive protein and mRNA levels in primary human hepatocytes: comparison with rifampicin. J Pharm Pharmacol. 2003 Sep;55(9):1229-39. doi: 10.1211/0022357021657. [PubMed:14604466  ] 
  3. Goodnick PJ: Pharmacokinetic optimisation of therapy with newer antidepressants. Clin Pharmacokinet. 1994 Oct;27(4):307-30. doi: 10.2165/00003088-199427040-00005. [PubMed:7834966  ] 
  4. Inoue T, Kitaichi Y, Koyama T: [Treatment strategy of refractory depression and its presynaptic mechanism of action]. Nihon Shinkei Seishin Yakurigaku Zasshi. 2003 Feb;23(1):11-20. [PubMed:12690637  ] 
  5. Hu KQ, Tiyyagura L, Kanel G, Redeker AG: Acute hepatitis induced by bupropion. Dig Dis Sci. 2000 Sep;45(9):1872-3. doi: 10.1023/a:1005553405313. [PubMed:11052334  ]