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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:51:32 UTC

Update Date

2022-03-07 02:55:25 UTC

HMDB ID

HMDB0037606

Secondary Accession Numbers

HMDB37606

Metabolite Identification

Common Name

13-Nor-6-eremophilene-8,11-dione

Description

13-Nor-6-eremophilene-8,11-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 13-Nor-6-eremophilene-8,11-dione.

Structure

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

HMDB0037606
     RDKit          3D
13-Nor-6-eremophilene-8,11-dione
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.4550    1.0956   -0.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7005    0.1756   -1.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -0.3724   -2.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -0.0392   -1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7060    0.5524   -0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254    0.3173   -0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231    1.1920   -1.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0060    0.8336    1.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1163    2.0018    1.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8089   -0.1837    2.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4114   -1.5108    2.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617   -2.0276    0.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1609   -1.0845   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -1.7112   -1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437   -0.9245   -2.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6540   -0.9819   -3.4971 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565    1.2850   -1.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9198    2.0707   -0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6591    0.6387    0.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3388    1.2045    0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7289    0.6741   -2.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0103    2.1681   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4871    1.3971   -0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0551    1.1896    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723    2.6837    0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234    1.6116    2.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6428    2.5417    2.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2783   -0.3235    2.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2539    0.2399    3.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5107   -1.5196    2.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0754   -2.2098    2.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2108   -2.2776    0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3990   -2.9831    0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860   -1.1036   -0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3985   -1.8819   -2.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -2.7381   -1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15  4  1  0
 13  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
M  END

  Mrv0541 05061309532D          

 16 17  0  0  0  0            999 V2000
    1.4289   -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
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    3.5724   -0.4125    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
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 11  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14  3  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15 10  2  0  0  0  0
 16 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037606

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCCC2CC(=O)C(=CC12C)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O2/c1-9-5-4-6-11-7-13(16)12(10(2)15)8-14(9,11)3/h8-9,11H,4-7H2,1-3H3

> <INCHI_KEY>
XNORMQKITMTNGH-UHFFFAOYSA-N

> <FORMULA>
C14H20O2

> <MOLECULAR_WEIGHT>
220.3074

> <EXACT_MASS>
220.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.137640606389528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-acetyl-4a,5-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
2.9894022016666666

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.42510089737361

> <JCHEM_PKA_STRONGEST_BASIC>
-6.923863902057177

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
64.4868

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-acetyl-4a,5-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037606
     RDKit          3D
13-Nor-6-eremophilene-8,11-dione
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.4550    1.0956   -0.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7005    0.1756   -1.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -0.3724   -2.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -0.0392   -1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7060    0.5524   -0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254    0.3173   -0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231    1.1920   -1.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0060    0.8336    1.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1163    2.0018    1.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8089   -0.1837    2.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4114   -1.5108    2.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617   -2.0276    0.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1609   -1.0845   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -1.7112   -1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437   -0.9245   -2.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6540   -0.9819   -3.4971 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565    1.2850   -1.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9198    2.0707   -0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6591    0.6387    0.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3388    1.2045    0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7289    0.6741   -2.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0103    2.1681   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4871    1.3971   -0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0551    1.1896    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723    2.6837    0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234    1.6116    2.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6428    2.5417    2.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2783   -0.3235    2.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2539    0.2399    3.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5107   -1.5196    2.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0754   -2.2098    2.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2108   -2.2776    0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3990   -2.9831    0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860   -1.1036   -0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3985   -1.8819   -2.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -2.7381   -1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15  4  1  0
 13  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   14                                                            
CONECT    4    5    6                                                       
CONECT    5    4    9                                                       
CONECT    6    4   11                                                       
CONECT    7   11   13                                                       
CONECT    8   12   14                                                       
CONECT    9    1    5   14                                                  
CONECT   10    2   12   15                                                  
CONECT   11    6    7   14                                                  
CONECT   12    8   10   13                                                  
CONECT   13    7   12   16                                                  
CONECT   14    3    8    9   11                                             
CONECT   15   10                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0037606
HETATM    1  C1  UNL     1       3.455   1.096  -0.886  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.701   0.176  -1.774  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.247  -0.372  -2.737  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.276  -0.039  -1.439  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.706   0.552  -0.408  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.725   0.317  -0.098  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.523   1.192  -1.065  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.006   0.834   1.280  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.116   2.002   1.654  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.809  -0.184   2.369  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.411  -1.511   2.109  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.862  -2.028   0.799  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.161  -1.084  -0.339  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.597  -1.711  -1.587  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.444  -0.925  -2.244  1.00  0.00           C  
HETATM   16  O2  UNL     1       0.654  -0.982  -3.497  1.00  0.00           O  
HETATM   17  H1  UNL     1       4.457   1.285  -1.331  1.00  0.00           H  
HETATM   18  H2  UNL     1       2.920   2.071  -0.787  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.659   0.639   0.116  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.339   1.205   0.181  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.729   0.674  -2.010  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.010   2.168  -1.202  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.487   1.397  -0.551  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.055   1.190   1.355  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.072   2.684   0.815  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.823   1.612   2.114  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.643   2.542   2.479  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.278  -0.323   2.591  1.00  0.00           H  
HETATM   29  H13 UNL     1      -1.254   0.240   3.298  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.511  -1.520   2.096  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.075  -2.210   2.894  1.00  0.00           H  
HETATM   32  H16 UNL     1       0.211  -2.278   0.881  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.399  -2.983   0.584  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.286  -1.104  -0.454  1.00  0.00           H  
HETATM   35  H19 UNL     1      -1.399  -1.882  -2.365  1.00  0.00           H  
HETATM   36  H20 UNL     1      -0.183  -2.738  -1.404  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3    4
CONECT    4    5    5   15
CONECT    5    6   20
CONECT    6    7    8   13
CONECT    7   21   22   23
CONECT    8    9   10   24
CONECT    9   25   26   27
CONECT   10   11   28   29
CONECT   11   12   30   31
CONECT   12   13   32   33
CONECT   13   14   34
CONECT   14   15   35   36
CONECT   15   16   16
END

HMDB0037606
     RDKit          3D
13-Nor-6-eremophilene-8,11-dione
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.4550    1.0956   -0.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7005    0.1756   -1.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -0.3724   -2.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -0.0392   -1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7060    0.5524   -0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254    0.3173   -0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231    1.1920   -1.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0060    0.8336    1.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1163    2.0018    1.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8089   -0.1837    2.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4114   -1.5108    2.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617   -2.0276    0.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1609   -1.0845   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -1.7112   -1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437   -0.9245   -2.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6540   -0.9819   -3.4971 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565    1.2850   -1.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9198    2.0707   -0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6591    0.6387    0.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3388    1.2045    0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7289    0.6741   -2.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0103    2.1681   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4871    1.3971   -0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0551    1.1896    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723    2.6837    0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234    1.6116    2.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6428    2.5417    2.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2783   -0.3235    2.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2539    0.2399    3.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5107   -1.5196    2.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0754   -2.2098    2.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2108   -2.2776    0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3990   -2.9831    0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860   -1.1036   -0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3985   -1.8819   -2.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -2.7381   -1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15  4  1  0
 13  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₂₀O₂

Average Molecular Weight

220.3074

Monoisotopic Molecular Weight

220.146329884

IUPAC Name

3-acetyl-4a,5-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one

Traditional Name

3-acetyl-4a,5-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-one

CAS Registry Number

348119-85-7

SMILES

CC1CCCC2CC(=O)C(=CC12C)C(C)=O

InChI Identifier

InChI=1S/C14H20O2/c1-9-5-4-6-11-7-13(16)12(10(2)15)8-14(9,11)3/h8-9,11H,4-7H2,1-3H3

InChI Key

XNORMQKITMTNGH-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: HMDB0037606)

Source

Endogenous

Endogenous (HMDB: HMDB0037606)

Plant

Plant (HMDB: HMDB0037606)

Animal

Animal (HMDB: HMDB0037606)

Exogenous

Food

Food (HMDB: HMDB0037606)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0037606)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037606)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037606)

Lipid metabolism pathway (HMDB: HMDB0037606)

Cellular process

Cell signaling (HMDB: HMDB0037606)

Biochemical process

Lipid transport (HMDB: HMDB0037606)

Role

Biological role

Energy source (HMDB: HMDB0037606)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037606)

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	0.092 g/L	ALOGPS
logP	2.75	ALOGPS
logP	2.99	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	18.43	ChemAxon
pKa (Strongest Basic)	-6.9	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	64.49 m³·mol⁻¹	ChemAxon
Polarizability	25.14 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]+	151.171	31661259
DarkChem	[M-H]-	147.742	31661259
DeepCCS	[M-2H]-	186.895	30932474
DeepCCS	[M+Na]+	162.947	30932474
AllCCS	[M+H]+	150.5	32859911
AllCCS	[M+H-H2O]+	146.6	32859911
AllCCS	[M+NH4]+	154.2	32859911
AllCCS	[M+Na]+	155.2	32859911
AllCCS	[M-H]-	158.0	32859911
AllCCS	[M+Na-2H]-	158.5	32859911
AllCCS	[M+HCOO]-	159.1	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.	7.24 minutes	32390414
Predicted by Siyang on May 30, 2022	16.848 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.34 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2348.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	520.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	200.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	288.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	375.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	671.8 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	781.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	75.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1403.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	475.9 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	1483.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	447.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	430.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	416.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	456.3 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	8.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
13-Nor-6-eremophilene-8,11-dione	CC1CCCC2CC(=O)C(=CC12C)C(C)=O	2341.4	Standard polar	33892256
13-Nor-6-eremophilene-8,11-dione	CC1CCCC2CC(=O)C(=CC12C)C(C)=O	1638.0	Standard non polar	33892256
13-Nor-6-eremophilene-8,11-dione	CC1CCCC2CC(=O)C(=CC12C)C(C)=O	1746.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
13-Nor-6-eremophilene-8,11-dione,1TMS,isomer #1	CC(=O)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C	1991.3	Semi standard non polar	33892256
13-Nor-6-eremophilene-8,11-dione,1TMS,isomer #1	CC(=O)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C	1754.2	Standard non polar	33892256
13-Nor-6-eremophilene-8,11-dione,1TMS,isomer #2	C=C(O[Si](C)(C)C)C1=CC2(C)C(C)CCCC2CC1=O	1992.3	Semi standard non polar	33892256
13-Nor-6-eremophilene-8,11-dione,1TMS,isomer #2	C=C(O[Si](C)(C)C)C1=CC2(C)C(C)CCCC2CC1=O	1821.5	Standard non polar	33892256
13-Nor-6-eremophilene-8,11-dione,2TMS,isomer #1	C=C(O[Si](C)(C)C)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C	2054.6	Semi standard non polar	33892256
13-Nor-6-eremophilene-8,11-dione,2TMS,isomer #1	C=C(O[Si](C)(C)C)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C	1914.6	Standard non polar	33892256
13-Nor-6-eremophilene-8,11-dione,1TBDMS,isomer #1	CC(=O)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C(C)(C)C	2232.5	Semi standard non polar	33892256
13-Nor-6-eremophilene-8,11-dione,1TBDMS,isomer #1	CC(=O)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C(C)(C)C	1972.2	Standard non polar	33892256
13-Nor-6-eremophilene-8,11-dione,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(C)CCCC2CC1=O	2237.8	Semi standard non polar	33892256
13-Nor-6-eremophilene-8,11-dione,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(C)CCCC2CC1=O	2066.5	Standard non polar	33892256
13-Nor-6-eremophilene-8,11-dione,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C(C)(C)C	2518.5	Semi standard non polar	33892256
13-Nor-6-eremophilene-8,11-dione,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C(C)(C)C	2305.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 13-Nor-6-eremophilene-8,11-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6u-1930000000-2ef2ca251c5d907b7950	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-Nor-6-eremophilene-8,11-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-Nor-6-eremophilene-8,11-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 - 13-Nor-6-eremophilene-8,11-dione 10V, Positive-QTOF	splash10-00di-0290000000-b3313219166b82100f34	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 20V, Positive-QTOF	splash10-00di-3950000000-703f3cda362bbddf0f96	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 40V, Positive-QTOF	splash10-05mo-7910000000-456ba727158f6c341e8e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 10V, Negative-QTOF	splash10-014i-0090000000-61a957fdc7b07681d3e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 20V, Negative-QTOF	splash10-014i-0190000000-be50c614e08e68205782	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 40V, Negative-QTOF	splash10-0h03-3920000000-80e43f5bc224bd141866	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 10V, Positive-QTOF	splash10-00di-0190000000-c84fe0fab83047027585	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 20V, Positive-QTOF	splash10-0a4l-5910000000-92335122ee40e3eeb7f9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 40V, Positive-QTOF	splash10-0006-9810000000-948ca7f16f6d09a1b743	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 10V, Negative-QTOF	splash10-014i-0090000000-b5ccca7192d7ca154168	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 20V, Negative-QTOF	splash10-014i-0090000000-8bd5034e70e2446446f1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 40V, Negative-QTOF	splash10-0i2c-1930000000-ee7c7892d15198f58c1e	2021-09-22	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

FDB016719

KNApSAcK ID

C00057359

Chemspider ID

35014444

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85288059

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 13-Nor-6-eremophilene-8,11-dione (HMDB0037606)

MOL for HMDB0037606 (13-Nor-6-eremophilene-8,11-dione)

3D MOL for HMDB0037606 (13-Nor-6-eremophilene-8,11-dione)

3D SDF for HMDB0037606 (13-Nor-6-eremophilene-8,11-dione)

3D-SDF for HMDB0037606 (13-Nor-6-eremophilene-8,11-dione)

PDB for HMDB0037606 (13-Nor-6-eremophilene-8,11-dione)

3D PDB for HMDB0037606 (13-Nor-6-eremophilene-8,11-dione)

SMILES for HMDB0037606 (13-Nor-6-eremophilene-8,11-dione)

INCHI for HMDB0037606 (13-Nor-6-eremophilene-8,11-dione)

Structure for HMDB0037606 (13-Nor-6-eremophilene-8,11-dione)

3D Structure for HMDB0037606 (13-Nor-6-eremophilene-8,11-dione)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra