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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:50 UTC

Update Date

2022-03-07 02:52:33 UTC

HMDB ID

HMDB0030446

Secondary Accession Numbers

HMDB30446

Metabolite Identification

Common Name

Grifolin

Description

Grifolin belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on Grifolin.

Structure

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

HMDB0030446
     RDKit          3D
Grifolin
 56 56  0  0  0  0  0  0  0  0999 V2000
   -6.4699   -1.0769   -1.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0864   -0.7392   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4789   -1.1509    0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4112   -0.0835    0.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0135    0.3275    0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0498   -0.2660    1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6697    0.2383    1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4455    1.6923    1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441   -0.6270    0.8983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3688   -0.4527    0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2563    0.8955    0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6994    0.7367   -0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5460   -0.1418    0.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1032    1.3540   -1.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    1.3597   -1.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4940    0.5768   -1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6344   -0.7886   -1.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6187   -1.4833   -2.0823 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7489   -1.4391   -0.9809 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7785   -0.7775   -0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9716   -1.5352    0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6428    0.5748   -0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5376    1.2460   -0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274    2.6248   -0.4632 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  4  2  3
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 18 50  1  0
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 22 55  1  0
 24 56  1  0
M  END


  Mrv0541 05061305142D          

 24 24  0  0  0  0            999 V2000
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0  0  0  0
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 10  7  1  0  0  0  0
 11  7  1  0  0  0  0
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 17 10  2  0  0  0  0
 18  4  1  0  0  0  0
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 22 15  2  0  0  0  0
 22 20  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030446

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC1=C(O)C=C(C)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O2/c1-16(2)8-6-9-17(3)10-7-11-18(4)12-13-20-21(23)14-19(5)15-22(20)24/h8,10,12,14-15,23-24H,6-7,9,11,13H2,1-5H3/b17-10+,18-12+

> <INCHI_KEY>
PZHNKNRPGLTZPO-VZRGJMDUSA-N

> <FORMULA>
C22H32O2

> <MOLECULAR_WEIGHT>
328.4883

> <EXACT_MASS>
328.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
40.436953676312626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyl-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzene-1,3-diol

> <ALOGPS_LOGP>
6.69

> <JCHEM_LOGP>
6.927532111333333

> <ALOGPS_LOGS>
-5.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.647277968375189

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.19301081602902

> <JCHEM_PKA_STRONGEST_BASIC>
-5.715809105897486

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
106.90899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methyl-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030446
     RDKit          3D
Grifolin
 56 56  0  0  0  0  0  0  0  0999 V2000
   -6.4699   -1.0769   -1.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0864   -0.7392   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4789   -1.1509    0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4112   -0.0835    0.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0135    0.3275    0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0498   -0.2660    1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6697    0.2383    1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4455    1.6923    1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3688   -0.4527    0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7489   -1.4391   -0.9809 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1355    3.1718   -0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
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  5  6  1  0
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  6 35  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 18 50  1  0
 19 51  1  0
 21 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 24 56  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   19                                                            
CONECT    6    8    9                                                       
CONECT    7   10   11                                                       
CONECT    8    6   16                                                       
CONECT    9    6   17                                                       
CONECT   10    7   17                                                       
CONECT   11    7   18                                                       
CONECT   12   13   18                                                       
CONECT   13   12   20                                                       
CONECT   14   19   21                                                       
CONECT   15   19   22                                                       
CONECT   16    1    2    8                                                  
CONECT   17    3    9   10                                                  
CONECT   18    4   11   12                                                  
CONECT   19    5   14   15                                                  
CONECT   20   13   21   22                                                  
CONECT   21   14   20   23                                                  
CONECT   22   15   20   24                                                  
CONECT   23   21                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0030446
HETATM    1  C1  UNL     1      -6.470  -1.077  -1.328  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.086  -0.739  -0.031  1.00  0.00           C  
HETATM    3  C3  UNL     1      -8.479  -1.151   0.235  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.411  -0.084   0.873  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.013   0.328   0.600  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.050  -0.266   1.610  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.670   0.238   1.207  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.445   1.692   1.161  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.744  -0.627   0.898  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.369  -0.453   0.489  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.256   0.895   0.487  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.699   0.737  -0.029  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.546  -0.142   0.784  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.103   1.354  -1.102  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.388   1.360  -1.768  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.494   0.577  -1.286  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.634  -0.789  -1.444  1.00  0.00           C  
HETATM   18  O1  UNL     1       3.619  -1.483  -2.082  1.00  0.00           O  
HETATM   19  C18 UNL     1       5.749  -1.439  -0.981  1.00  0.00           C  
HETATM   20  C19 UNL     1       6.779  -0.777  -0.342  1.00  0.00           C  
HETATM   21  C20 UNL     1       7.972  -1.535   0.143  1.00  0.00           C  
HETATM   22  C21 UNL     1       6.643   0.575  -0.184  1.00  0.00           C  
HETATM   23  C22 UNL     1       5.538   1.246  -0.638  1.00  0.00           C  
HETATM   24  O2  UNL     1       5.427   2.625  -0.463  1.00  0.00           O  
HETATM   25  H1  UNL     1      -6.195  -0.097  -1.818  1.00  0.00           H  
HETATM   26  H2  UNL     1      -5.565  -1.725  -1.203  1.00  0.00           H  
HETATM   27  H3  UNL     1      -7.184  -1.549  -2.034  1.00  0.00           H  
HETATM   28  H4  UNL     1      -9.039  -0.216   0.530  1.00  0.00           H  
HETATM   29  H5  UNL     1      -8.584  -1.832   1.106  1.00  0.00           H  
HETATM   30  H6  UNL     1      -8.998  -1.533  -0.666  1.00  0.00           H  
HETATM   31  H7  UNL     1      -6.892   0.160   1.838  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.734  -0.044  -0.404  1.00  0.00           H  
HETATM   33  H9  UNL     1      -4.919   1.443   0.604  1.00  0.00           H  
HETATM   34  H10 UNL     1      -4.084  -1.367   1.611  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.327   0.142   2.602  1.00  0.00           H  
HETATM   36  H12 UNL     1      -3.346   2.211   1.645  1.00  0.00           H  
HETATM   37  H13 UNL     1      -1.606   2.062   1.725  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.442   2.000   0.081  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.093  -1.706   0.967  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.268  -1.103   1.192  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.164  -0.957  -0.518  1.00  0.00           H  
HETATM   42  H18 UNL     1      -0.183   1.659  -0.129  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.459   1.225   1.561  1.00  0.00           H  
HETATM   44  H20 UNL     1       2.114  -0.256   1.832  1.00  0.00           H  
HETATM   45  H21 UNL     1       3.548   0.252   0.976  1.00  0.00           H  
HETATM   46  H22 UNL     1       2.570  -1.201   0.429  1.00  0.00           H  
HETATM   47  H23 UNL     1       1.294   1.988  -1.579  1.00  0.00           H  
HETATM   48  H24 UNL     1       3.270   1.095  -2.877  1.00  0.00           H  
HETATM   49  H25 UNL     1       3.707   2.456  -1.864  1.00  0.00           H  
HETATM   50  H26 UNL     1       2.795  -1.030  -2.429  1.00  0.00           H  
HETATM   51  H27 UNL     1       5.873  -2.518  -1.098  1.00  0.00           H  
HETATM   52  H28 UNL     1       8.535  -0.849   0.812  1.00  0.00           H  
HETATM   53  H29 UNL     1       7.651  -2.446   0.722  1.00  0.00           H  
HETATM   54  H30 UNL     1       8.563  -1.851  -0.737  1.00  0.00           H  
HETATM   55  H31 UNL     1       7.465   1.095   0.325  1.00  0.00           H  
HETATM   56  H32 UNL     1       6.135   3.172  -0.008  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4    4
CONECT    3   28   29   30
CONECT    4    5   31
CONECT    5    6   32   33
CONECT    6    7   34   35
CONECT    7    8    9    9
CONECT    8   36   37   38
CONECT    9   10   39
CONECT   10   11   40   41
CONECT   11   12   42   43
CONECT   12   13   14   14
CONECT   13   44   45   46
CONECT   14   15   47
CONECT   15   16   48   49
CONECT   16   17   17   23
CONECT   17   18   19
CONECT   18   50
CONECT   19   20   20   51
CONECT   20   21   22
CONECT   21   52   53   54
CONECT   22   23   23   55
CONECT   23   24
CONECT   24   56
END

HMDB0030446
     RDKit          3D
Grifolin
 56 56  0  0  0  0  0  0  0  0999 V2000
   -6.4699   -1.0769   -1.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0864   -0.7392   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4789   -1.1509    0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4112   -0.0835    0.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0135    0.3275    0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0498   -0.2660    1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6697    0.2383    1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4455    1.6923    1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441   -0.6270    0.8983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3688   -0.4527    0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2563    0.8955    0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6994    0.7367   -0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5460   -0.1418    0.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1032    1.3540   -1.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    1.3597   -1.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4940    0.5768   -1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6344   -0.7886   -1.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6187   -1.4833   -2.0823 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7489   -1.4391   -0.9809 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7785   -0.7775   -0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9716   -1.5352    0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6428    0.5748   -0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5376    1.2460   -0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274    2.6248   -0.4632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1951   -0.0967   -1.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5654   -1.7248   -1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1844   -1.5485   -2.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0393   -0.2161    0.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5840   -1.8318    1.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9982   -1.5328   -0.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8917    0.1599    1.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7344   -0.0442   -0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9187    1.4433    0.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0842   -1.3667    1.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3274    0.1424    2.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3456    2.2112    1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6061    2.0618    1.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4424    2.0003    0.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0932   -1.7060    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2678   -1.1027    1.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1645   -0.9570   -0.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1832    1.6585   -0.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4591    1.2252    1.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141   -0.2564    1.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5479    0.2515    0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5701   -1.2007    0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2945    1.9883   -1.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2697    1.0952   -2.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7075    2.4561   -1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -1.0295   -2.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8735   -2.5180   -1.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5350   -0.8492    0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6514   -2.4463    0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5632   -1.8513   -0.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4647    1.0950    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1355    3.1718   -0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 23 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 18 50  1  0
 19 51  1  0
 21 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 24 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,8,12-Trimethyl-5,7,11-tridecatriene-3,4-diol	MeSH
2-Farnesyl-5-methylresorcinol	HMDB
5-Methyl-2-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-1,3-benzenediol, 9ci	HMDB
Ammonium, hexadecyltrimethyl-, pentachlorophenol	HMDB
Ammonium, hexadecyltrimethyl-, pentachlorophenoxide	HMDB
Ammonium, hexadecyltrimethyl-, pentachlorophenoxide (8ci)	HMDB
e,e,5-Methyl-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-1,3-benzenediol	HMDB
Hexadecyltrimethylammonium pentachlorophenol	HMDB
Hexadecyltrimethylammonium pentachlorophenoxide (6ci,7ci)	HMDB
Trimethylcetylammonium pentachlorophenate	HMDB
Grifolin	MeSH

Chemical Formula

C₂₂H₃₂O₂

Average Molecular Weight

328.4883

Monoisotopic Molecular Weight

328.240230268

IUPAC Name

5-methyl-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzene-1,3-diol

Traditional Name

5-methyl-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzene-1,3-diol

CAS Registry Number

6903-07-7

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC1=C(O)C=C(C)C=C1O

InChI Identifier

InChI=1S/C22H32O2/c1-16(2)8-6-9-17(3)10-7-11-18(4)12-13-20-21(23)14-19(5)15-22(20)24/h8,10,12,14-15,23-24H,6-7,9,11,13H2,1-5H3/b17-10+,18-12+

InChI Key

PZHNKNRPGLTZPO-VZRGJMDUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Resorcinol
M-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030446)

Source

Endogenous

Endogenous (HMDB: HMDB0030446)

Plant

Plant (HMDB: HMDB0030446)

Animal

Animal (HMDB: HMDB0030446)

Exogenous

Food

Food (HMDB: HMDB0030446)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0030446)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0030446)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0030446)

Lipid metabolism pathway (HMDB: HMDB0030446)

Cellular process

Cell signaling (HMDB: HMDB0030446)

Biochemical process

Lipid transport (HMDB: HMDB0030446)

Role

Biological role

Energy source (HMDB: HMDB0030446)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030446)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	43 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0017 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	6.69	ALOGPS
logP	6.93	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	106.91 m³·mol⁻¹	ChemAxon
Polarizability	40.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	183.622	31661259
DarkChem	[M-H]-	182.186	31661259
DeepCCS	[M+H]+	184.871	30932474
DeepCCS	[M-H]-	182.513	30932474
DeepCCS	[M-2H]-	216.256	30932474
DeepCCS	[M+Na]+	191.609	30932474
AllCCS	[M+H]+	188.0	32859911
AllCCS	[M+H-H2O]+	185.0	32859911
AllCCS	[M+NH4]+	190.8	32859911
AllCCS	[M+Na]+	191.6	32859911
AllCCS	[M-H]-	183.4	32859911
AllCCS	[M+Na-2H]-	183.9	32859911
AllCCS	[M+HCOO]-	184.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	10.39 minutes	32390414
Predicted by Siyang on May 30, 2022	21.1014 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.17 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3302.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	540.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	259.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	280.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	196.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	952.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	867.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1927.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	805.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1379.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	664.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	514.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	260.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	395.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Grifolin	CC(C)=CCC\C(C)=C\CC\C(C)=C\CC1=C(O)C=C(C)C=C1O	3669.9	Standard polar	33892256
Grifolin	CC(C)=CCC\C(C)=C\CC\C(C)=C\CC1=C(O)C=C(C)C=C1O	2519.8	Standard non polar	33892256
Grifolin	CC(C)=CCC\C(C)=C\CC\C(C)=C\CC1=C(O)C=C(C)C=C1O	2686.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Grifolin,1TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC1=C(O)C=C(C)C=C1O[Si](C)(C)C	2602.2	Semi standard non polar	33892256
Grifolin,2TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC1=C(O[Si](C)(C)C)C=C(C)C=C1O[Si](C)(C)C	2579.3	Semi standard non polar	33892256
Grifolin,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC1=C(O)C=C(C)C=C1O[Si](C)(C)C(C)(C)C	2851.4	Semi standard non polar	33892256
Grifolin,2TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC1=C(O[Si](C)(C)C(C)(C)C)C=C(C)C=C1O[Si](C)(C)C(C)(C)C	3033.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Grifolin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bvj-3942000000-2bee1b20893cdc0d8a08	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grifolin GC-MS (2 TMS) - 70eV, Positive	splash10-0a4r-5506900000-80b9eb2eee557fe0c2f2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grifolin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grifolin 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 - Grifolin 10V, Positive-QTOF	splash10-004i-0549000000-43065ed9c2de04617841	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grifolin 20V, Positive-QTOF	splash10-05tr-1920000000-743b2ca32fcdb3c3bddc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grifolin 40V, Positive-QTOF	splash10-0gbi-8900000000-5748a3a70df6e1f653eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grifolin 10V, Negative-QTOF	splash10-004i-0009000000-5761757dcee8ed7bbe30	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grifolin 20V, Negative-QTOF	splash10-004i-0219000000-45ec07490ddb6554caa7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grifolin 40V, Negative-QTOF	splash10-0229-2932000000-af2aa9395deb57466368	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grifolin 10V, Negative-QTOF	splash10-004i-0109000000-55ca267c88fd3e767cac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grifolin 20V, Negative-QTOF	splash10-004r-0927000000-3b2c61b285bed01d3901	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grifolin 40V, Negative-QTOF	splash10-00vm-1930000000-78c42ae7f2bffb8b11db	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grifolin 10V, Positive-QTOF	splash10-004i-1935000000-3e05ade6d1af2b95f7e0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grifolin 20V, Positive-QTOF	splash10-052r-2900000000-798a02baa2ee48984578	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grifolin 40V, Positive-QTOF	splash10-0a4r-3900000000-367bc194ef877b30082b	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB002311

KNApSAcK ID

C00023937

Chemspider ID

4522608

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Grifolin

METLIN ID

Not Available

PubChem Compound

5372312

PDB ID

Not Available

ChEBI ID

544843

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1820021

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Luo XJ, Li LL, Deng QP, Yu XF, Yang LF, Luo FJ, Xiao LB, Chen XY, Ye M, Liu JK, Cao Y: Grifolin, a potent antitumour natural product upregulates death-associated protein kinase 1 DAPK1 via p53 in nasopharyngeal carcinoma cells. Eur J Cancer. 2011 Jan;47(2):316-25. doi: 10.1016/j.ejca.2010.09.021. Epub 2010 Oct 11. [PubMed:20943371 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Grifolin (HMDB0030446)

MOL for HMDB0030446 (Grifolin)

3D MOL for HMDB0030446 (Grifolin)

3D SDF for HMDB0030446 (Grifolin)

3D-SDF for HMDB0030446 (Grifolin)

PDB for HMDB0030446 (Grifolin)

3D PDB for HMDB0030446 (Grifolin)

SMILES for HMDB0030446 (Grifolin)

INCHI for HMDB0030446 (Grifolin)

Structure for HMDB0030446 (Grifolin)

3D Structure for HMDB0030446 (Grifolin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra