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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:23:30 UTC

Update Date

2022-03-07 02:54:29 UTC

HMDB ID

HMDB0035412

Secondary Accession Numbers

HMDB35412

Metabolite Identification

Common Name

1(10),11-Eremophiladiene-2,9-dione

Description

1(10),11-Eremophiladiene-2,9-dione belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review a small amount of articles have been published on 1(10),11-Eremophiladiene-2,9-dione.

Structure

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

HMDB0035412
     RDKit          3D
1(10),11-Eremophiladiene-2,9-dione
 37 38  0  0  0  0  0  0  0  0999 V2000
    2.9438    1.6745    0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7451    0.4077    0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9479   -0.4121    1.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4336   -0.2225    0.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5627   -1.4904   -0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2508   -2.1915   -0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2221   -3.3926   -0.6761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9465   -1.4093   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9803   -2.0586    0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1922   -1.3070    0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3244   -1.7928    0.6376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9855    0.1184    1.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0989    0.8163    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7921    2.1741    0.6085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9034    0.0324   -0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8917    0.1142   -1.9430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655    0.6891    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1465    2.3326    0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9294    2.1565    0.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6635    0.2371    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4177   -0.7728    0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6598   -1.2326    1.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2105   -0.5965    1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895   -1.3124   -1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2547   -2.1876    0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9576   -3.1338    0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4928    0.2351    2.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9556    0.6518    1.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8022    1.0206   -0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7585    2.7607    0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6122    2.1207    1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0599    2.7598    0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9312    0.2002   -2.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4398   -0.7674   -2.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3808    1.0689   -2.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874    1.3361    0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750    1.3729   -0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17  4  1  0
 15  8  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
M  END

  Mrv0541 05061308262D          

 17 18  0  0  0  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  2  0  0  0  0
 14  6  1  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  2  0  0  0  0
 17 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035412

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC(=O)C=C2C(=O)CC(CC12C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O2/c1-9(2)11-6-14(17)13-7-12(16)5-10(3)15(13,4)8-11/h7,10-11H,1,5-6,8H2,2-4H3

> <INCHI_KEY>
CEDQTRQWBOXWOT-UHFFFAOYSA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.3181

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.38502999404999

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4a,5-dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,7-dione

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
3.032553451333334

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.618221091871996

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
68.7637

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6-tetrahydro-2H-naphthalene-1,7-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0035412
     RDKit          3D
1(10),11-Eremophiladiene-2,9-dione
 37 38  0  0  0  0  0  0  0  0999 V2000
    2.9438    1.6745    0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7451    0.4077    0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9479   -0.4121    1.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4336   -0.2225    0.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5627   -1.4904   -0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2508   -2.1915   -0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2221   -3.3926   -0.6761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9465   -1.4093   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9803   -2.0586    0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1922   -1.3070    0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3244   -1.7928    0.6376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9855    0.1184    1.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0989    0.8163    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7921    2.1741    0.6085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9034    0.0324   -0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8917    0.1142   -1.9430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655    0.6891    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1465    2.3326    0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9294    2.1565    0.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6635    0.2371    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4177   -0.7728    0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6598   -1.2326    1.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2105   -0.5965    1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895   -1.3124   -1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2547   -2.1876    0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9576   -3.1338    0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4928    0.2351    2.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9556    0.6518    1.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8022    1.0206   -0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7585    2.7607    0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6122    2.1207    1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0599    2.7598    0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9312    0.2002   -2.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4398   -0.7674   -2.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3808    1.0689   -2.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874    1.3361    0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750    1.3729   -0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17  4  1  0
 15  8  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  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       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   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   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   15                                                            
CONECT    5   10   12                                                       
CONECT    6   11   14                                                       
CONECT    7   12   13                                                       
CONECT    8   11   15                                                       
CONECT    9    1    2   11                                                  
CONECT   10    3    5   15                                                  
CONECT   11    6    8    9                                                  
CONECT   12    5    7   16                                                  
CONECT   13    7   14   15                                                  
CONECT   14    6   13   17                                                  
CONECT   15    4    8   10   13                                             
CONECT   16   12                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0035412
HETATM    1  C1  UNL     1       2.944   1.674   0.389  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.745   0.408   0.621  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.948  -0.412   1.008  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.434  -0.222   0.511  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.563  -1.490  -0.299  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.251  -2.191  -0.380  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.222  -3.393  -0.676  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.946  -1.409  -0.101  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.980  -2.059   0.388  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.192  -1.307   0.680  1.00  0.00           C  
HETATM   11  O2  UNL     1      -4.324  -1.793   0.638  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.986   0.118   1.043  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.099   0.816   0.024  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.792   2.174   0.608  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.903   0.032  -0.398  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.892   0.114  -1.943  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.366   0.689   0.091  1.00  0.00           C  
HETATM   18  H1  UNL     1       2.147   2.333   0.109  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.929   2.156   0.462  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.663   0.237   1.554  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.418  -0.773   0.076  1.00  0.00           H  
HETATM   22  H5  UNL     1       3.660  -1.233   1.697  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.210  -0.596   1.569  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.990  -1.312  -1.303  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.255  -2.188   0.212  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.958  -3.134   0.577  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.493   0.235   2.026  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.956   0.652   1.046  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.802   1.021  -0.843  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.758   2.761   0.553  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.612   2.121   1.721  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.060   2.760   0.060  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.931   0.200  -2.326  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.440  -0.767  -2.387  1.00  0.00           H  
HETATM   35  H18 UNL     1      -0.381   1.069  -2.228  1.00  0.00           H  
HETATM   36  H19 UNL     1       0.087   1.336   0.948  1.00  0.00           H  
HETATM   37  H20 UNL     1       0.675   1.373  -0.728  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3    4
CONECT    3   20   21   22
CONECT    4    5   17   23
CONECT    5    6   24   25
CONECT    6    7    7    8
CONECT    8    9    9   15
CONECT    9   10   26
CONECT   10   11   11   12
CONECT   12   13   27   28
CONECT   13   14   15   29
CONECT   14   30   31   32
CONECT   15   16   17
CONECT   16   33   34   35
CONECT   17   36   37
END

HMDB0035412
     RDKit          3D
1(10),11-Eremophiladiene-2,9-dione
 37 38  0  0  0  0  0  0  0  0999 V2000
    2.9438    1.6745    0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7451    0.4077    0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9479   -0.4121    1.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4336   -0.2225    0.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5627   -1.4904   -0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2508   -2.1915   -0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2221   -3.3926   -0.6761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9465   -1.4093   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9803   -2.0586    0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1922   -1.3070    0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3244   -1.7928    0.6376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9855    0.1184    1.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0989    0.8163    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7921    2.1741    0.6085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9034    0.0324   -0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8917    0.1142   -1.9430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655    0.6891    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1465    2.3326    0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9294    2.1565    0.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6635    0.2371    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4177   -0.7728    0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6598   -1.2326    1.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2105   -0.5965    1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895   -1.3124   -1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2547   -2.1876    0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9576   -3.1338    0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4928    0.2351    2.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9556    0.6518    1.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8022    1.0206   -0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7585    2.7607    0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6122    2.1207    1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0599    2.7598    0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9312    0.2002   -2.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4398   -0.7674   -2.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3808    1.0689   -2.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874    1.3361    0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750    1.3729   -0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17  4  1  0
 15  8  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₂

Average Molecular Weight

232.3181

Monoisotopic Molecular Weight

232.146329884

IUPAC Name

4a,5-dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,7-dione

Traditional Name

4a,5-dimethyl-3-(prop-1-en-2-yl)-3,4,5,6-tetrahydro-2H-naphthalene-1,7-dione

CAS Registry Number

Not Available

SMILES

CC1CC(=O)C=C2C(=O)CC(CC12C)C(C)=C

InChI Identifier

InChI=1S/C15H20O2/c1-9(2)11-6-14(17)13-7-12(16)5-10(3)15(13,4)8-11/h7,10-11H,1,5-6,8H2,2-4H3

InChI Key

CEDQTRQWBOXWOT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035412)

Source

Endogenous

Endogenous (HMDB: HMDB0035412)

Plant

Plant (HMDB: HMDB0035412)

Animal

Animal (HMDB: HMDB0035412)

Exogenous

Food

Food (HMDB: HMDB0035412)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Exogenous (HMDB: HMDB0035412)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035412)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035412)

Lipid metabolism pathway (HMDB: HMDB0035412)

Cellular process

Cell signaling (HMDB: HMDB0035412)

Biochemical process

Lipid transport (HMDB: HMDB0035412)

Role

Biological role

Energy source (HMDB: HMDB0035412)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035412)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	71 - 72.5 °C	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	0.11 g/L	ALOGPS
logP	2.02	ALOGPS
logP	3.03	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.76 m³·mol⁻¹	ChemAxon
Polarizability	26.39 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]+	156.459	31661259
DarkChem	[M-H]-	153.657	31661259
DeepCCS	[M-2H]-	188.215	30932474
DeepCCS	[M+Na]+	163.781	30932474
AllCCS	[M+H]+	153.7	32859911
AllCCS	[M+H-H2O]+	149.9	32859911
AllCCS	[M+NH4]+	157.2	32859911
AllCCS	[M+Na]+	158.2	32859911
AllCCS	[M-H]-	161.1	32859911
AllCCS	[M+Na-2H]-	161.4	32859911
AllCCS	[M+HCOO]-	161.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1(10),11-Eremophiladiene-2,9-dione	CC1CC(=O)C=C2C(=O)CC(CC12C)C(C)=C	2583.6	Standard polar	33892256
1(10),11-Eremophiladiene-2,9-dione	CC1CC(=O)C=C2C(=O)CC(CC12C)C(C)=C	1742.1	Standard non polar	33892256
1(10),11-Eremophiladiene-2,9-dione	CC1CC(=O)C=C2C(=O)CC(CC12C)C(C)=C	1886.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1(10),11-Eremophiladiene-2,9-dione,1TMS,isomer #1	C=C(C)C1CC(=O)C2=CC(O[Si](C)(C)C)=CC(C)C2(C)C1	2036.3	Semi standard non polar	33892256
1(10),11-Eremophiladiene-2,9-dione,1TMS,isomer #1	C=C(C)C1CC(=O)C2=CC(O[Si](C)(C)C)=CC(C)C2(C)C1	1822.3	Standard non polar	33892256
1(10),11-Eremophiladiene-2,9-dione,1TMS,isomer #2	C=C(C)C1C=C(O[Si](C)(C)C)C2=CC(=O)CC(C)C2(C)C1	2032.5	Semi standard non polar	33892256
1(10),11-Eremophiladiene-2,9-dione,1TMS,isomer #2	C=C(C)C1C=C(O[Si](C)(C)C)C2=CC(=O)CC(C)C2(C)C1	1881.0	Standard non polar	33892256
1(10),11-Eremophiladiene-2,9-dione,2TMS,isomer #1	C=C(C)C1C=C(O[Si](C)(C)C)C2=CC(O[Si](C)(C)C)=CC(C)C2(C)C1	2076.6	Semi standard non polar	33892256
1(10),11-Eremophiladiene-2,9-dione,2TMS,isomer #1	C=C(C)C1C=C(O[Si](C)(C)C)C2=CC(O[Si](C)(C)C)=CC(C)C2(C)C1	1957.7	Standard non polar	33892256
1(10),11-Eremophiladiene-2,9-dione,1TBDMS,isomer #1	C=C(C)C1CC(=O)C2=CC(O[Si](C)(C)C(C)(C)C)=CC(C)C2(C)C1	2317.7	Semi standard non polar	33892256
1(10),11-Eremophiladiene-2,9-dione,1TBDMS,isomer #1	C=C(C)C1CC(=O)C2=CC(O[Si](C)(C)C(C)(C)C)=CC(C)C2(C)C1	2050.0	Standard non polar	33892256
1(10),11-Eremophiladiene-2,9-dione,1TBDMS,isomer #2	C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C2=CC(=O)CC(C)C2(C)C1	2296.8	Semi standard non polar	33892256
1(10),11-Eremophiladiene-2,9-dione,1TBDMS,isomer #2	C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C2=CC(=O)CC(C)C2(C)C1	2086.5	Standard non polar	33892256
1(10),11-Eremophiladiene-2,9-dione,2TBDMS,isomer #1	C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C2=CC(O[Si](C)(C)C(C)(C)C)=CC(C)C2(C)C1	2554.8	Semi standard non polar	33892256
1(10),11-Eremophiladiene-2,9-dione,2TBDMS,isomer #1	C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C2=CC(O[Si](C)(C)C(C)(C)C)=CC(C)C2(C)C1	2342.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1(10),11-Eremophiladiene-2,9-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-2930000000-6a544b52c030c6646896	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1(10),11-Eremophiladiene-2,9-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1(10),11-Eremophiladiene-2,9-dione 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 - 1(10),11-Eremophiladiene-2,9-dione 10V, Positive-QTOF	splash10-001i-0290000000-864b8aa3aa7f8905dd63	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1(10),11-Eremophiladiene-2,9-dione 20V, Positive-QTOF	splash10-00m0-3960000000-f61e547c3e3e3b415c94	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1(10),11-Eremophiladiene-2,9-dione 40V, Positive-QTOF	splash10-014i-9600000000-2aa304d38aa9b2ef51fd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1(10),11-Eremophiladiene-2,9-dione 10V, Negative-QTOF	splash10-001i-0090000000-18f559eebb3889fd82a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1(10),11-Eremophiladiene-2,9-dione 20V, Negative-QTOF	splash10-001i-0090000000-a900567806e9c7da6ced	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1(10),11-Eremophiladiene-2,9-dione 40V, Negative-QTOF	splash10-02tl-3960000000-21cc64dd06c1f7cc8235	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1(10),11-Eremophiladiene-2,9-dione 10V, Positive-QTOF	splash10-001i-0090000000-b2e20fdf59c5262e7fa1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1(10),11-Eremophiladiene-2,9-dione 20V, Positive-QTOF	splash10-00lr-1960000000-a7f4fda04d0a68026ea9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1(10),11-Eremophiladiene-2,9-dione 40V, Positive-QTOF	splash10-00r6-7920000000-937f2c9c1ea69c61488c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1(10),11-Eremophiladiene-2,9-dione 10V, Negative-QTOF	splash10-001i-0090000000-403b175a8d75af9b9dc4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1(10),11-Eremophiladiene-2,9-dione 20V, Negative-QTOF	splash10-001i-0090000000-b84c33fcb6412471e3f2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1(10),11-Eremophiladiene-2,9-dione 40V, Negative-QTOF	splash10-00b9-0980000000-1dd74a1e93e6ecb2ffa7	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB014089

KNApSAcK ID

Not Available

Chemspider ID

35013925

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751741

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

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 1(10),11-Eremophiladiene-2,9-dione (HMDB0035412)

MOL for HMDB0035412 (1(10),11-Eremophiladiene-2,9-dione)

3D MOL for HMDB0035412 (1(10),11-Eremophiladiene-2,9-dione)

3D SDF for HMDB0035412 (1(10),11-Eremophiladiene-2,9-dione)

3D-SDF for HMDB0035412 (1(10),11-Eremophiladiene-2,9-dione)

PDB for HMDB0035412 (1(10),11-Eremophiladiene-2,9-dione)

3D PDB for HMDB0035412 (1(10),11-Eremophiladiene-2,9-dione)

SMILES for HMDB0035412 (1(10),11-Eremophiladiene-2,9-dione)

INCHI for HMDB0035412 (1(10),11-Eremophiladiene-2,9-dione)

Structure for HMDB0035412 (1(10),11-Eremophiladiene-2,9-dione)

3D Structure for HMDB0035412 (1(10),11-Eremophiladiene-2,9-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra