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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-22 19:49:44 UTC

Update Date

2021-09-14 14:58:48 UTC

HMDB ID

HMDB0061129

Secondary Accession Numbers

HMDB61129

Metabolite Identification

Common Name

6-Methyl-griseofulvin

Description

6-Methyl-griseofulvin is a metabolite of griseofulvin. Griseofulvin (marketed under the proprietary name Grifulvin V by Orthoneutrogena Labs, according to FDA orange book) is an antifungal drug that is administered orally. It is used both in animals and in humans, to treat fungal infections of the skin (commonly known as ringworm) and nails. It is produced by culture of some strains of the mold Penicillium griseofulvum, from which it was isolated in 1939. (Wikipedia)

Structure

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

HMDB0061129
     RDKit          3D
6-Methyl-griseofulvin
 40 42  0  0  0  0  0  0  0  0999 V2000
    1.0732   -2.6115   -1.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1073   -1.2151   -1.6550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447   -0.3878   -0.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2378   -0.4284   -1.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1915    0.4218   -0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3397    0.6486   -0.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6682    0.9843    0.8814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3008    1.5551    0.5779 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4841    2.5846   -0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3486    0.4974    0.0857 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8465   -0.3079    1.1345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5306   -0.4647    1.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010   -1.3405    1.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7855   -2.4693    2.8791 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7540   -1.3300    1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6848   -2.2529    2.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2008   -0.4248    0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503    0.4373   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7884    1.3483   -1.1109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1553    1.4653   -1.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9769    0.4341    0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1408    1.2078   -0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0479    2.2161   -1.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3785   -3.1463   -1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318   -2.9543   -1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8359   -2.6808   -0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6270   -1.1075   -1.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6617    0.2552    1.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3381    1.8511    1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8411    2.0406    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574    2.1429   -1.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491    3.4816   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5421    2.9783   -0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1663   -2.9545    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5073   -1.7308    2.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0960   -2.8915    2.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2598   -0.4155    0.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4355    0.7389   -2.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8249    1.3421   -0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3764    2.4828   -1.8805 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  1
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  2  0
 10  3  1  0
 21 12  1  0
 22 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  1
  9 31  1  0
  9 32  1  0
  9 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
M  END


  Mrv0541 07221312492D          

 23 25  0  0  0  0            999 V2000
   -0.8100   -0.0929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2894   -0.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3638    0.5895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640    0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1844   -0.8339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4621   -0.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4116    0.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0927    0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8896    1.3252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0182   -0.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1047   -1.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -0.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1127    0.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4671   -0.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411    2.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8934   -0.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2402   -1.6465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456    0.4488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0623    1.6518    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2930   -0.2231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -2.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2938   -1.5564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5363    0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  1  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2 22  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  6  0  0  0
  6 12  1  0  0  0  0
  6  7  2  0  0  0  0
  7 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 15  1  0  0  0  0
 10 14  1  0  0  0  0
 12 16  2  0  0  0  0
 12 17  1  0  0  0  0
 13 18  2  0  0  0  0
 13 19  1  0  0  0  0
 14 20  2  0  0  0  0
 16 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061129

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(C)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H17ClO5/c1-8-5-11(21-3)13-15(14(8)18)23-17(16(13)20)9(2)6-10(19)7-12(17)22-4/h5,7,9H,6H2,1-4H3/t9-,17+/m1/s1

> <INCHI_KEY>
QNPINWFXONNRKM-XLFHBGCDSA-N

> <FORMULA>
C17H17ClO5

> <MOLECULAR_WEIGHT>
336.767

> <EXACT_MASS>
336.076451361

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.380928420970875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,6'R)-7-chloro-2',4-dimethoxy-6,6'-dimethyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
2.8432301133333335

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.688454981013308

> <JCHEM_PKA_STRONGEST_BASIC>
-4.444577871553183

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
86.42389999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,6'R)-7-chloro-2',4-dimethoxy-6,6'-dimethylspiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061129
     RDKit          3D
6-Methyl-griseofulvin
 40 42  0  0  0  0  0  0  0  0999 V2000
    1.0732   -2.6115   -1.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1073   -1.2151   -1.6550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447   -0.3878   -0.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2378   -0.4284   -1.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1915    0.4218   -0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3397    0.6486   -0.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6682    0.9843    0.8814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3008    1.5551    0.5779 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4841    2.5846   -0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3486    0.4974    0.0857 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8465   -0.3079    1.1345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5306   -0.4647    1.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010   -1.3405    1.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7855   -2.4693    2.8791 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7540   -1.3300    1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6848   -2.2529    2.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2008   -0.4248    0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503    0.4373   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7884    1.3483   -1.1109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1553    1.4653   -1.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9769    0.4341    0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1408    1.2078   -0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0479    2.2161   -1.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3785   -3.1463   -1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318   -2.9543   -1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8359   -2.6808   -0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6270   -1.1075   -1.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6617    0.2552    1.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3381    1.8511    1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8411    2.0406    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574    2.1429   -1.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491    3.4816   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5421    2.9783   -0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1663   -2.9545    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5073   -1.7308    2.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0960   -2.8915    2.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2598   -0.4155    0.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4355    0.7389   -2.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8249    1.3421   -0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3764    2.4828   -1.8805 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  1
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  2  0
 10  3  1  0
 21 12  1  0
 22 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  1
  9 31  1  0
  9 32  1  0
  9 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
M  END

HEADER    PROTEIN                                 22-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUL-13         0                                  
HETATM    1  C   UNK     0      -1.512  -0.173   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.540  -1.368   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.679   1.100   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.359   1.100   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.211  -1.557   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.863  -0.818   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.768   0.699   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.906   1.011   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.661   2.474   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.767  -1.641   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.062  -2.855   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.246  -1.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.077   1.537   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.605  -0.342   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.503   3.772   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.534  -0.679   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.315  -3.073   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.445   0.838   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       1.983   3.083   0.000  0.00  0.00          Cl+0
HETATM   20  O   UNK     0      -6.147  -0.416   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.693  -3.772   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.548  -2.905   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.734   1.680   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6   22                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8    9                                                  
CONECT    5    1   10   11                                                  
CONECT    6    2   12    7                                                  
CONECT    7    3    6   13                                                  
CONECT    8    4   14                                                       
CONECT    9    4   15                                                       
CONECT   10    5   14                                                       
CONECT   11    5                                                            
CONECT   12    6   16   17                                                  
CONECT   13    7   18   19                                                  
CONECT   14    8   10   20                                                  
CONECT   15    9                                                            
CONECT   16   12   18                                                       
CONECT   17   12   21                                                       
CONECT   18   13   16   23                                                  
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   17                                                            
CONECT   22    2                                                            
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0061129
HETATM    1  C1  UNL     1       1.073  -2.612  -1.337  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.107  -1.215  -1.655  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.945  -0.388  -0.919  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.238  -0.428  -1.149  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.191   0.422  -0.406  1.00  0.00           C  
HETATM    6  O2  UNL     1       5.340   0.649  -0.824  1.00  0.00           O  
HETATM    7  C5  UNL     1       3.668   0.984   0.881  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.301   1.555   0.578  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.484   2.585  -0.520  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.349   0.497   0.086  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.847  -0.308   1.134  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.531  -0.465   1.027  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.401  -1.340   1.695  1.00  0.00           C  
HETATM   14 CL1  UNL     1      -0.786  -2.469   2.879  1.00  0.00          CL  
HETATM   15  C11 UNL     1      -2.754  -1.330   1.433  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.685  -2.253   2.135  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.201  -0.425   0.493  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.350   0.437  -0.166  1.00  0.00           C  
HETATM   19  O4  UNL     1      -2.788   1.348  -1.111  1.00  0.00           O  
HETATM   20  C15 UNL     1      -4.155   1.465  -1.476  1.00  0.00           C  
HETATM   21  C16 UNL     1      -0.977   0.434   0.092  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.141   1.208  -0.433  1.00  0.00           C  
HETATM   23  O5  UNL     1       0.048   2.216  -1.143  1.00  0.00           O  
HETATM   24  H1  UNL     1       0.379  -3.146  -1.986  1.00  0.00           H  
HETATM   25  H2  UNL     1       2.132  -2.954  -1.437  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.836  -2.681  -0.253  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.627  -1.107  -1.909  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.662   0.255   1.692  1.00  0.00           H  
HETATM   29  H6  UNL     1       4.338   1.851   1.113  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.841   2.041   1.463  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.357   2.143  -1.527  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.849   3.482  -0.357  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.542   2.978  -0.498  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.166  -2.954   1.392  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.507  -1.731   2.639  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.096  -2.892   2.808  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.260  -0.415   0.287  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.436   0.739  -2.263  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.825   1.342  -0.580  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.376   2.483  -1.881  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   27
CONECT    5    6    6    7
CONECT    7    8   28   29
CONECT    8    9   10   30
CONECT    9   31   32   33
CONECT   10   11   22
CONECT   11   12
CONECT   12   13   13   21
CONECT   13   14   15
CONECT   15   16   17   17
CONECT   16   34   35   36
CONECT   17   18   37
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   38   39   40
CONECT   21   22
CONECT   22   23   23
END

HMDB0061129
     RDKit          3D
6-Methyl-griseofulvin
 40 42  0  0  0  0  0  0  0  0999 V2000
    1.0732   -2.6115   -1.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1073   -1.2151   -1.6550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447   -0.3878   -0.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2378   -0.4284   -1.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1915    0.4218   -0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3397    0.6486   -0.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6682    0.9843    0.8814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3008    1.5551    0.5779 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4841    2.5846   -0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3486    0.4974    0.0857 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8465   -0.3079    1.1345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5306   -0.4647    1.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010   -1.3405    1.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7855   -2.4693    2.8791 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7540   -1.3300    1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6848   -2.2529    2.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2008   -0.4248    0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503    0.4373   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7884    1.3483   -1.1109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1553    1.4653   -1.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9769    0.4341    0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1408    1.2078   -0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0479    2.2161   -1.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3785   -3.1463   -1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318   -2.9543   -1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8359   -2.6808   -0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6270   -1.1075   -1.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6617    0.2552    1.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3381    1.8511    1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8411    2.0406    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574    2.1429   -1.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491    3.4816   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5421    2.9783   -0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1663   -2.9545    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5073   -1.7308    2.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0960   -2.8915    2.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2598   -0.4155    0.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4355    0.7389   -2.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8249    1.3421   -0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3764    2.4828   -1.8805 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  1
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  2  0
 10  3  1  0
 21 12  1  0
 22 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  1
  9 31  1  0
  9 32  1  0
  9 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₇ClO₅

Average Molecular Weight

336.767

Monoisotopic Molecular Weight

336.076451361

IUPAC Name

(2S,6'R)-7-chloro-2',4-dimethoxy-6,6'-dimethyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

Traditional Name

(2S,6'R)-7-chloro-2',4-dimethoxy-6,6'-dimethylspiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(C)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC

InChI Identifier

InChI=1S/C17H17ClO5/c1-8-5-11(21-3)13-15(14(8)18)23-17(16(13)20)9(2)6-10(19)7-12(17)22-4/h5,7,9H,6H2,1-4H3/t9-,17+/m1/s1

InChI Key

QNPINWFXONNRKM-XLFHBGCDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Coumaran
Benzofuran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Cyclohexenone
Aryl chloride
Aryl halide
Benzenoid
Vinylogous ester
Ketone
Cyclic ketone
Ether
Oxacycle
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Liver (HMDB: HMDB0061129)
Kidney (HMDB: HMDB0061129)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061129)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061129)

Cellular substructure

Cytoplasm (HMDB: HMDB0061129)
Membrane (HMDB: HMDB0061129)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	2.55	ALOGPS
logP	2.84	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	17.69	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	86.42 m³·mol⁻¹	ChemAxon
Polarizability	33.38 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	180.345	30932474
DeepCCS	[M-H]-	177.987	30932474
DeepCCS	[M-2H]-	211.31	30932474
DeepCCS	[M+Na]+	186.54	30932474
AllCCS	[M+H]+	174.9	32859911
AllCCS	[M+H-H2O]+	171.6	32859911
AllCCS	[M+NH4]+	177.9	32859911
AllCCS	[M+Na]+	178.8	32859911
AllCCS	[M-H]-	181.1	32859911
AllCCS	[M+Na-2H]-	181.0	32859911
AllCCS	[M+HCOO]-	181.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Methyl-griseofulvin	COC1=CC(C)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC	3612.5	Standard polar	33892256
6-Methyl-griseofulvin	COC1=CC(C)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC	2615.0	Standard non polar	33892256
6-Methyl-griseofulvin	COC1=CC(C)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC	2666.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Methyl-griseofulvin,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(C)=CC(OC)=C1C2=O	2566.3	Semi standard non polar	33892256
6-Methyl-griseofulvin,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(C)=CC(OC)=C1C2=O	2488.8	Standard non polar	33892256
6-Methyl-griseofulvin,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(C)=CC(OC)=C1C2=O	3156.3	Standard polar	33892256
6-Methyl-griseofulvin,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(C)=CC(OC)=C1C2=O	2781.4	Semi standard non polar	33892256
6-Methyl-griseofulvin,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(C)=CC(OC)=C1C2=O	2700.3	Standard non polar	33892256
6-Methyl-griseofulvin,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(C)=CC(OC)=C1C2=O	3251.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Methyl-griseofulvin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00aj-9114000000-bf0baf8b7848bbcb6c72	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Methyl-griseofulvin 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-griseofulvin 10V, Positive-QTOF	splash10-000i-0309000000-006b63517dc08a1bb663	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-griseofulvin 20V, Positive-QTOF	splash10-00kk-4904000000-9f6ee5360372c4738e5b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-griseofulvin 40V, Positive-QTOF	splash10-06e9-3900000000-cf64f017d2e2ee4c8c31	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-griseofulvin 10V, Negative-QTOF	splash10-000i-0009000000-d09a1215bdc61824ce7f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-griseofulvin 20V, Negative-QTOF	splash10-000i-0029000000-e1a883edad5f62526719	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-griseofulvin 40V, Negative-QTOF	splash10-0a4r-9670000000-debd5bc9d6c57ffc0aa4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-griseofulvin 10V, Positive-QTOF	splash10-000i-0009000000-7e3bc2a475760b20d81e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-griseofulvin 20V, Positive-QTOF	splash10-000i-0149000000-48e439fda071ef1f621b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-griseofulvin 40V, Positive-QTOF	splash10-000i-4293000000-5a31c49499345019442a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-griseofulvin 10V, Negative-QTOF	splash10-000i-0009000000-cbf134e04b7e4a4f3e55	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-griseofulvin 20V, Negative-QTOF	splash10-000i-0229000000-395e16d8a9a9e5c91972	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-griseofulvin 40V, Negative-QTOF	splash10-008i-8965000000-fefa5cdae575b1bb2b34	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131770040

PDB ID

Not Available

ChEBI ID

Not Available

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

Showing metabocard for 6-Methyl-griseofulvin (HMDB0061129)

MOL for HMDB0061129 (6-Methyl-griseofulvin)

3D MOL for HMDB0061129 (6-Methyl-griseofulvin)

3D SDF for HMDB0061129 (6-Methyl-griseofulvin)

3D-SDF for HMDB0061129 (6-Methyl-griseofulvin)

PDB for HMDB0061129 (6-Methyl-griseofulvin)

3D PDB for HMDB0061129 (6-Methyl-griseofulvin)

SMILES for HMDB0061129 (6-Methyl-griseofulvin)

INCHI for HMDB0061129 (6-Methyl-griseofulvin)

Structure for HMDB0061129 (6-Methyl-griseofulvin)

3D Structure for HMDB0061129 (6-Methyl-griseofulvin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra