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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014604

Secondary Accession Numbers

HMDB14604

Metabolite Identification

Common Name

Nabumetone

Description

Nabumetone, also known as relafen or relif, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Nabumetone is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, nabumetone is involved in nabumetone action pathway. A methyl ketone that is 2-butanone in which one of the methyl hydrogens at position 4 is replaced by a 6-methoxy-2-naphthyl group. It is shown to have a slightly lower risk of gastrointestinal side effects than most other non-steroidal anti-inflammatory drugs. A prodrug that is converted to the active metabolite, 6-methoxy-2-naphthylacetic acid, following oral administration.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014604
     RDKit          3D
Nabumetone
 33 34  0  0  0  0  0  0  0  0999 V2000
   -6.1132   -0.1222    0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0460   -0.9267    0.7807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7245   -0.4675    0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4159    0.7681    0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1212    1.2361    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0991    0.4054    0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135    0.8415    0.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2173    0.0212    0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    0.5294    0.8003 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2239    0.0920   -0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5998    0.6372   -0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6025    0.1114    0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9305    1.5015   -1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9395   -1.2140    1.4362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693   -1.6324    1.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3948   -0.8318    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180   -1.2858    1.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9507    0.8821    0.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0202   -0.0150   -0.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0907   -0.5057    0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2323    1.3842   -0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8561    2.1991   -0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3906    1.8210    0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2471    0.1140    1.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    1.6297    0.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2826   -1.0029   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987    0.5157   -1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6241   -1.0011    0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6062    0.5638    0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2803    0.4808    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7241   -1.8702    1.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6383   -2.5992    1.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022   -2.2594    1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  8 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  3  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
M  END

461
  Mrv0541 02231214422D          

 17 18  0  0  0  0            999 V2000
    8.1336    1.2429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641   -1.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929   -0.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361    0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786   -0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216    1.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -0.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734    1.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209    0.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -0.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641   -0.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8496    0.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  1 17  1  0  0  0  0
  2 15  2  0  0  0  0
  3  4  1  0  0  0  0
  3  7  2  0  0  0  0
  3  9  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
  8 15  1  0  0  0  0
  9 10  2  0  0  0  0
 11 14  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014604

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C=C(CCC(C)=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O2/c1-11(16)3-4-12-5-6-14-10-15(17-2)8-7-13(14)9-12/h5-10H,3-4H2,1-2H3

> <INCHI_KEY>
BLXXJMDCKKHMKV-UHFFFAOYSA-N

> <FORMULA>
C15H16O2

> <MOLECULAR_WEIGHT>
228.2863

> <EXACT_MASS>
228.115029756

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.165625730820228

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(6-methoxynaphthalen-2-yl)butan-2-one

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
3.2169937839999996

> <ALOGPS_LOGS>
-5.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.591539825276776

> <JCHEM_PKA_STRONGEST_BASIC>
-4.826872761363677

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
68.43110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nabumetone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014604
     RDKit          3D
Nabumetone
 33 34  0  0  0  0  0  0  0  0999 V2000
   -6.1132   -0.1222    0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0460   -0.9267    0.7807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7245   -0.4675    0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4159    0.7681    0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1212    1.2361    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0991    0.4054    0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135    0.8415    0.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2173    0.0212    0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    0.5294    0.8003 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2239    0.0920   -0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5998    0.6372   -0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6025    0.1114    0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9305    1.5015   -1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9395   -1.2140    1.4362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693   -1.6324    1.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3948   -0.8318    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180   -1.2858    1.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9507    0.8821    0.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0202   -0.0150   -0.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0907   -0.5057    0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2323    1.3842   -0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8561    2.1991   -0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3906    1.8210    0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2471    0.1140    1.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    1.6297    0.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2826   -1.0029   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987    0.5157   -1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6241   -1.0011    0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6062    0.5638    0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2803    0.4808    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7241   -1.8702    1.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6383   -2.5992    1.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022   -2.2594    1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  8 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  3  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 461                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      15.183   2.320   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.413  -2.336   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.414  -0.027   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.080  -0.797   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.081  -0.027   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.081   1.513   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.747  -0.797   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747  -0.027   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.414   1.513   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.747   2.283   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.457  -0.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.457   2.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.852   1.545   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.852  -0.059   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.413  -0.797   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080  -0.027   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.519   1.555   0.000  0.00  0.00           C+0
CONECT    1   13   17                                                       
CONECT    2   15                                                            
CONECT    3    4    7    9                                                  
CONECT    4    3    8                                                       
CONECT    5    6    7   11                                                  
CONECT    6    5   10   12                                                  
CONECT    7    3    5                                                       
CONECT    8    4   15                                                       
CONECT    9    3   10                                                       
CONECT   10    6    9                                                       
CONECT   11    5   14                                                       
CONECT   12    6   13                                                       
CONECT   13    1   12   14                                                  
CONECT   14   11   13                                                       
CONECT   15    2    8   16                                                  
CONECT   16   15                                                            
CONECT   17    1                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0014604
HETATM    1  C1  UNL     1      -6.113  -0.122   0.327  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.046  -0.927   0.781  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.725  -0.467   0.691  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.416   0.768   0.162  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.121   1.236   0.066  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.099   0.405   0.530  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.214   0.842   0.448  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.217   0.021   0.905  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.619   0.529   0.800  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.224   0.092  -0.538  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.600   0.637  -0.579  1.00  0.00           C  
HETATM   12  C11 UNL     1       5.603   0.111   0.379  1.00  0.00           C  
HETATM   13  O2  UNL     1       4.931   1.502  -1.367  1.00  0.00           O  
HETATM   14  C12 UNL     1       0.939  -1.214   1.436  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.369  -1.632   1.509  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.395  -0.832   1.059  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.718  -1.286   1.146  1.00  0.00           C  
HETATM   18  H1  UNL     1      -5.951   0.882   0.770  1.00  0.00           H  
HETATM   19  H2  UNL     1      -6.020  -0.015  -0.751  1.00  0.00           H  
HETATM   20  H3  UNL     1      -7.091  -0.506   0.691  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.232   1.384  -0.189  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.856   2.199  -0.345  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.391   1.821   0.029  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.247   0.114   1.614  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.593   1.630   0.908  1.00  0.00           H  
HETATM   26  H9  UNL     1       3.283  -1.003  -0.596  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.599   0.516  -1.368  1.00  0.00           H  
HETATM   28  H11 UNL     1       5.624  -1.001   0.387  1.00  0.00           H  
HETATM   29  H12 UNL     1       6.606   0.564   0.232  1.00  0.00           H  
HETATM   30  H13 UNL     1       5.280   0.481   1.398  1.00  0.00           H  
HETATM   31  H14 UNL     1       1.724  -1.870   1.801  1.00  0.00           H  
HETATM   32  H15 UNL     1      -0.638  -2.599   1.919  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.902  -2.259   1.562  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   16
CONECT    7    8    8   23
CONECT    8    9   14
CONECT    9   10   24   25
CONECT   10   11   26   27
CONECT   11   12   13   13
CONECT   12   28   29   30
CONECT   14   15   15   31
CONECT   15   16   32
CONECT   16   17   17
CONECT   17   33
END

HMDB0014604
     RDKit          3D
Nabumetone
 33 34  0  0  0  0  0  0  0  0999 V2000
   -6.1132   -0.1222    0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0460   -0.9267    0.7807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7245   -0.4675    0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4159    0.7681    0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1212    1.2361    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0991    0.4054    0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135    0.8415    0.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2173    0.0212    0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    0.5294    0.8003 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2239    0.0920   -0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5998    0.6372   -0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6025    0.1114    0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9305    1.5015   -1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9395   -1.2140    1.4362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693   -1.6324    1.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3948   -0.8318    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180   -1.2858    1.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9507    0.8821    0.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0202   -0.0150   -0.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0907   -0.5057    0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2323    1.3842   -0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8561    2.1991   -0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3906    1.8210    0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2471    0.1140    1.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    1.6297    0.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2826   -1.0029   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987    0.5157   -1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6241   -1.0011    0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6062    0.5638    0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2803    0.4808    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7241   -1.8702    1.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6383   -2.5992    1.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022   -2.2594    1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  8 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  3  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(6-Methoxy-2-naphthalenyl)-2-butanone	ChEBI
4-(6-Methoxy-2-naphthyl)-2-butanone	ChEBI
Nabumetona	ChEBI
Nabumetonum	ChEBI
Relafen	ChEBI
Arthraxan	HMDB
Listran	HMDB
Nabumeton	HMDB
Apo-nabumetone	HMDB
Nabucox	HMDB
Relif	HMDB
Mebutan	HMDB
Rhoxal-nabumetone	HMDB
Gen-nabumetone	HMDB
Relifex	HMDB
Rhoxal nabumetone	HMDB
ApoNabumetone	HMDB

Chemical Formula

C₁₅H₁₆O₂

Average Molecular Weight

228.2863

Monoisotopic Molecular Weight

228.115029756

IUPAC Name

4-(6-methoxynaphthalen-2-yl)butan-2-one

Traditional Name

nabumetone

CAS Registry Number

42924-53-8

SMILES

COC1=CC2=C(C=C1)C=C(CCC(C)=O)C=C2

InChI Identifier

InChI=1S/C15H16O2/c1-11(16)3-4-12-5-6-14-10-15(17-2)8-7-13(14)9-12/h5-10H,3-4H2,1-2H3

InChI Key

BLXXJMDCKKHMKV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Anisole
Alkyl aryl ether
Ketone
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

methyl ketone (CHEBI:7443 )
methoxynaphthalene (CHEBI:7443 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0014604)
Membrane (HMDB: HMDB0014604)

Biofluid or Excreta

Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Nabumetone Action Pathway (PathBank: SMP0000114)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0019 g/L	Not Available
LogP	3.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0019 g/L	ALOGPS
logP	3.41	ALOGPS
logP	3.22	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	19.59	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.43 m³·mol⁻¹	ChemAxon
Polarizability	26.17 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	154.759	31661259
DarkChem	[M-H]-	154.4	31661259
DeepCCS	[M+H]+	159.082	30932474
DeepCCS	[M-H]-	156.724	30932474
DeepCCS	[M-2H]-	189.617	30932474
DeepCCS	[M+Na]+	165.175	30932474
AllCCS	[M+H]+	153.1	32859911
AllCCS	[M+H-H2O]+	149.1	32859911
AllCCS	[M+NH4]+	156.8	32859911
AllCCS	[M+Na]+	157.9	32859911
AllCCS	[M-H]-	158.5	32859911
AllCCS	[M+Na-2H]-	158.5	32859911
AllCCS	[M+HCOO]-	158.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nabumetone	COC1=CC2=C(C=C1)C=C(CCC(C)=O)C=C2	3001.9	Standard polar	33892256
Nabumetone	COC1=CC2=C(C=C1)C=C(CCC(C)=O)C=C2	1956.4	Standard non polar	33892256
Nabumetone	COC1=CC2=C(C=C1)C=C(CCC(C)=O)C=C2	2091.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nabumetone,1TMS,isomer #1	COC1=CC=C2C=C(CC=C(C)O[Si](C)(C)C)C=CC2=C1	2229.0	Semi standard non polar	33892256
Nabumetone,1TMS,isomer #1	COC1=CC=C2C=C(CC=C(C)O[Si](C)(C)C)C=CC2=C1	2150.5	Standard non polar	33892256
Nabumetone,1TMS,isomer #1	COC1=CC=C2C=C(CC=C(C)O[Si](C)(C)C)C=CC2=C1	2690.6	Standard polar	33892256
Nabumetone,1TMS,isomer #2	C=C(CCC1=CC=C2C=C(OC)C=CC2=C1)O[Si](C)(C)C	2134.4	Semi standard non polar	33892256
Nabumetone,1TMS,isomer #2	C=C(CCC1=CC=C2C=C(OC)C=CC2=C1)O[Si](C)(C)C	2133.9	Standard non polar	33892256
Nabumetone,1TMS,isomer #2	C=C(CCC1=CC=C2C=C(OC)C=CC2=C1)O[Si](C)(C)C	2694.1	Standard polar	33892256
Nabumetone,1TBDMS,isomer #1	COC1=CC=C2C=C(CC=C(C)O[Si](C)(C)C(C)(C)C)C=CC2=C1	2487.3	Semi standard non polar	33892256
Nabumetone,1TBDMS,isomer #1	COC1=CC=C2C=C(CC=C(C)O[Si](C)(C)C(C)(C)C)C=CC2=C1	2386.8	Standard non polar	33892256
Nabumetone,1TBDMS,isomer #1	COC1=CC=C2C=C(CC=C(C)O[Si](C)(C)C(C)(C)C)C=CC2=C1	2782.2	Standard polar	33892256
Nabumetone,1TBDMS,isomer #2	C=C(CCC1=CC=C2C=C(OC)C=CC2=C1)O[Si](C)(C)C(C)(C)C	2407.2	Semi standard non polar	33892256
Nabumetone,1TBDMS,isomer #2	C=C(CCC1=CC=C2C=C(OC)C=CC2=C1)O[Si](C)(C)C(C)(C)C	2341.0	Standard non polar	33892256
Nabumetone,1TBDMS,isomer #2	C=C(CCC1=CC=C2C=C(OC)C=CC2=C1)O[Si](C)(C)C(C)(C)C	2791.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nabumetone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7930000000-53550e3b73002ac9c671	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nabumetone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nabumetone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nabumetone LC-ESI-qTof , Positive-QTOF	splash10-00di-0900000000-af6f3d0d1c5f77f47279	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nabumetone LC-ESI-qTof , Positive-QTOF	splash10-00di-0900000000-6b7de93b51a79132630f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nabumetone LC-ESI-qTof , Positive-QTOF	splash10-004i-4910000000-a4f59053ed0ee04bb88f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nabumetone , positive-QTOF	splash10-00di-0900000000-6b7de93b51a79132630f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nabumetone , positive-QTOF	splash10-00di-0900000000-af6f3d0d1c5f77f47279	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nabumetone , positive-QTOF	splash10-00fr-2900000000-53d7d6dc809a154d16c2	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabumetone 10V, Positive-QTOF	splash10-01t9-0190000000-b864e89d948e8076c3fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabumetone 20V, Positive-QTOF	splash10-03fr-1290000000-657a908ca7f06b7711a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabumetone 40V, Positive-QTOF	splash10-0udi-3900000000-86bd2c983b81aa7bef16	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabumetone 10V, Negative-QTOF	splash10-004i-0090000000-4938674275db31bd9e41	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabumetone 20V, Negative-QTOF	splash10-004i-0290000000-7bbcedc9462b3b3aed77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabumetone 40V, Negative-QTOF	splash10-03dl-2940000000-3cfbcbe6458c3d4b1000	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabumetone 10V, Positive-QTOF	splash10-00di-0960000000-dc5e2e6a6aaebbe05161	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabumetone 20V, Positive-QTOF	splash10-00di-0930000000-76ec0fb1eac9f0347fa1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabumetone 40V, Positive-QTOF	splash10-05bo-0900000000-cbb1b90e5fe8c723de8c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabumetone 10V, Negative-QTOF	splash10-004i-0090000000-202799ccfbea13f5ad79	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabumetone 20V, Negative-QTOF	splash10-0a6r-5960000000-d4422601462c920c62ac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabumetone 40V, Negative-QTOF	splash10-014i-0900000000-63bc8342ce285796ade9	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Nabumetone Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00461	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00461	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00461

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4256

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nabumetone

METLIN ID

Not Available

PubChem Compound

4409

PDB ID

NBO

ChEBI ID

7443

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Myeloperoxidase

General function:: Involved in peroxidase activity
Specific function:: Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:: MPO
Uniprot ID:: P05164
Molecular weight:: 83867.71

References

Saleh TS, Calixto JB, Medeiros YS: Effects of anti-inflammatory drugs upon nitrate and myeloperoxidase levels in the mouse pleurisy induced by carrageenan. Peptides. 1999;20(8):949-56. [PubMed:10503773 ]

Enzyme Details

2. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Fackovcova D, Kristova V, Kriska M: Renal damage induced by the treatment with non-opioid analgesics--theoretical assumption or clinical significance. Bratisl Lek Listy. 2000;101(8):417-22. [PubMed:11153163 ]
Roy HK, Karolski WJ, Ratashak A: Distal bowel selectivity in the chemoprevention of experimental colon carcinogenesis by the non-steroidal anti-inflammatory drug nabumetone. Int J Cancer. 2001 May 15;92(4):609-15. [PubMed:11304699 ]
van Kraaij DJ, Hovestad-Witterland AH, de Metz M, Vollaard EJ: A comparison of the effects of nabumetone vs meloxicam on serum thromboxane B2 and platelet function in healthy volunteers. Br J Clin Pharmacol. 2002 Jun;53(6):644-7. [PubMed:12047490 ]
Hedner T, Samulesson O, Wahrborg P, Wadenvik H, Ung KA, Ekbom A: Nabumetone: therapeutic use and safety profile in the management of osteoarthritis and rheumatoid arthritis. Drugs. 2004;64(20):2315-43; discussion 2344-5. [PubMed:15456329 ]
Elliott SN, McKnight W, Cirino G, Wallace JL: A nitric oxide-releasing nonsteroidal anti-inflammatory drug accelerates gastric ulcer healing in rats. Gastroenterology. 1995 Aug;109(2):524-30. [PubMed:7615202 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Giuliano F, Ferraz JG, Pereira R, de Nucci G, Warner TD: Cyclooxygenase selectivity of non-steroid anti-inflammatory drugs in humans: ex vivo evaluation. Eur J Pharmacol. 2001 Aug 24;426(1-2):95-103. [PubMed:11525777 ]
Takeuchi K, Smale S, Premchand P, Maiden L, Sherwood R, Thjodleifsson B, Bjornsson E, Bjarnason I: Prevalence and mechanism of nonsteroidal anti-inflammatory drug-induced clinical relapse in patients with inflammatory bowel disease. Clin Gastroenterol Hepatol. 2006 Feb;4(2):196-202. [PubMed:16469680 ]
Cipollone F, Ganci A, Panara MR, Greco A, Cuccurullo F, Patrono C, Patrignani P: Effects of nabumetone on prostanoid biosynthesis in humans. Clin Pharmacol Ther. 1995 Sep;58(3):335-41. [PubMed:7554708 ]
Bensen W, Zizzo A: Newer, safer nonsteroidal anti-inflammatory drugs. Rational NSAID selection for arthritis. Can Fam Physician. 1998 Jan;44:101-2, 105-7. [PubMed:9481468 ]

Enzyme Details

4. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Turpeinen M, Hofmann U, Klein K, Murdter T, Schwab M, Zanger UM: A predominate role of CYP1A2 for the metabolism of nabumetone to the active metabolite, 6-methoxy-2-naphthylacetic acid, in human liver microsomes. Drug Metab Dispos. 2009 May;37(5):1017-24. doi: 10.1124/dmd.108.025700. Epub 2009 Feb 9. [PubMed:19204080 ]

Showing metabocard for Nabumetone (HMDB0014604)

MOL for HMDB0014604 (Nabumetone)

3D MOL for HMDB0014604 (Nabumetone)

3D SDF for HMDB0014604 (Nabumetone)

3D-SDF for HMDB0014604 (Nabumetone)

PDB for HMDB0014604 (Nabumetone)

3D PDB for HMDB0014604 (Nabumetone)

SMILES for HMDB0014604 (Nabumetone)

INCHI for HMDB0014604 (Nabumetone)

Structure for HMDB0014604 (Nabumetone)

3D Structure for HMDB0014604 (Nabumetone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References