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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:21:41 UTC

Update Date

2022-03-07 02:56:44 UTC

HMDB ID

HMDB0040778

Secondary Accession Numbers

HMDB40778

Metabolite Identification

Common Name

Eremopetasidione

Description

Eremopetasidione 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 Eremopetasidione.

Structure

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

HMDB0040778
     RDKit          3D
Eremopetasidione
 37 38  0  0  0  0  0  0  0  0999 V2000
    4.3356    0.6516   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0869    0.8688    0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0280    1.6723    1.7136 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8768    0.0935    0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7528    0.2579    1.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4930   -0.4616    0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8760   -1.1751    2.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4476   -1.4488   -0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454   -1.6101   -1.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2692   -0.3223   -1.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7933    0.8901   -0.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180    1.9463   -0.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5673    0.5971    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1478    1.9055    1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729   -1.2820   -1.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9254   -0.8434   -0.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0156   -1.2780   -1.1286 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0840    1.3940    0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1318    0.7771   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7483   -0.3497    0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7356    0.9629    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980   -1.9730    1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0078   -1.6928    2.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3946   -0.4952    2.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717   -2.4675    0.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5132   -2.1232   -0.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5330   -2.2798   -1.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3750   -0.3458   -1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0316   -0.1808   -2.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8401    1.2725   -1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2905    2.7879   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4944    0.2816    1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    1.8600    2.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9740    2.6327    0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483    2.3187    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4288   -0.5778   -2.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8599   -2.2638   -1.8563 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 16  4  1  0
 13  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
M  END


  Mrv0541 05061312072D          

 17 18  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
    1.4289    0.0000    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
    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
    0.7145   -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
    0.0000   -1.6500    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
  8  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  0  0  0  0
 13 11  1  0  0  0  0
 14  3  1  0  0  0  0
 14  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040778

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C(O)CCC2CC(=O)C(=CC12C)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O3/c1-8-12(16)5-4-10-6-13(17)11(9(2)15)7-14(8,10)3/h7-8,10,12,16H,4-6H2,1-3H3

> <INCHI_KEY>
ZKOZDFWTXYIUDZ-UHFFFAOYSA-N

> <FORMULA>
C14H20O3

> <MOLECULAR_WEIGHT>
236.3068

> <EXACT_MASS>
236.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.01489825390499

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
1.6806374046666674

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.30113264552566

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.41984677827395

> <JCHEM_PKA_STRONGEST_BASIC>
-0.917484170693699

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
66.0793

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.96e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040778
     RDKit          3D
Eremopetasidione
 37 38  0  0  0  0  0  0  0  0999 V2000
    4.3356    0.6516   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0869    0.8688    0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0280    1.6723    1.7136 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8768    0.0935    0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7528    0.2579    1.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4930   -0.4616    0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8760   -1.1751    2.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4476   -1.4488   -0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454   -1.6101   -1.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2692   -0.3223   -1.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7933    0.8901   -0.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180    1.9463   -0.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5673    0.5971    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1478    1.9055    1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729   -1.2820   -1.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9254   -0.8434   -0.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0156   -1.2780   -1.1286 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0840    1.3940    0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1318    0.7771   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7483   -0.3497    0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7356    0.9629    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980   -1.9730    1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0078   -1.6928    2.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3946   -0.4952    2.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717   -2.4675    0.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5132   -2.1232   -0.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5330   -2.2798   -1.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3750   -0.3458   -1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0316   -0.1808   -2.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8401    1.2725   -1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2905    2.7879   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4944    0.2816    1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    1.8600    2.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9740    2.6327    0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483    2.3187    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4288   -0.5778   -2.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8599   -2.2638   -1.8563 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 16  4  1  0
 13  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 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       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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   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       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       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   14                                                            
CONECT    4    5   10                                                       
CONECT    5    4   12                                                       
CONECT    6   10   13                                                       
CONECT    7   11   14                                                       
CONECT    8    1   12   14                                                  
CONECT    9    2   11   15                                                  
CONECT   10    4    6   14                                                  
CONECT   11    7    9   13                                                  
CONECT   12    5    8   16                                                  
CONECT   13    6   11   17                                                  
CONECT   14    3    7    8   10                                             
CONECT   15    9                                                            
CONECT   16   12                                                            
CONECT   17   13                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0040778
HETATM    1  C1  UNL     1       4.336   0.652  -0.010  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.087   0.869   0.764  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.028   1.672   1.714  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.877   0.093   0.380  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.753   0.258   1.042  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.493  -0.462   0.737  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.876  -1.175   2.052  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.448  -1.449  -0.359  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.745  -1.610  -1.114  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.269  -0.322  -1.673  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.793   0.890  -0.922  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.718   1.946  -0.978  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.567   0.597   0.550  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.148   1.906   1.174  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.673  -1.282  -1.354  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.925  -0.843  -0.719  1.00  0.00           C  
HETATM   17  O3  UNL     1       3.016  -1.278  -1.129  1.00  0.00           O  
HETATM   18  H1  UNL     1       5.084   1.394   0.342  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.132   0.777  -1.106  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.748  -0.350   0.228  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.736   0.963   1.860  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.598  -1.973   1.743  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.008  -1.693   2.488  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.395  -0.495   2.732  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.272  -2.467   0.106  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.513  -2.123  -0.500  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.533  -2.280  -1.973  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.375  -0.346  -1.581  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.032  -0.181  -2.742  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.840   1.273  -1.331  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.291   2.788  -1.295  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.494   0.282   1.024  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.052   1.860   2.266  1.00  0.00           H  
HETATM   34  H17 UNL     1      -1.974   2.633   0.955  1.00  0.00           H  
HETATM   35  H18 UNL     1      -0.248   2.319   0.662  1.00  0.00           H  
HETATM   36  H19 UNL     1       0.429  -0.578  -2.175  1.00  0.00           H  
HETATM   37  H20 UNL     1       0.860  -2.264  -1.856  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3    4
CONECT    4    5    5   16
CONECT    5    6   21
CONECT    6    7    8   13
CONECT    7   22   23   24
CONECT    8    9   15   25
CONECT    9   10   26   27
CONECT   10   11   28   29
CONECT   11   12   13   30
CONECT   12   31
CONECT   13   14   32
CONECT   14   33   34   35
CONECT   15   16   36   37
CONECT   16   17   17
END

HMDB0040778
     RDKit          3D
Eremopetasidione
 37 38  0  0  0  0  0  0  0  0999 V2000
    4.3356    0.6516   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0869    0.8688    0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0280    1.6723    1.7136 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8768    0.0935    0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7528    0.2579    1.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4930   -0.4616    0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8760   -1.1751    2.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4476   -1.4488   -0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454   -1.6101   -1.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2692   -0.3223   -1.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7933    0.8901   -0.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180    1.9463   -0.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5673    0.5971    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1478    1.9055    1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729   -1.2820   -1.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9254   -0.8434   -0.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0156   -1.2780   -1.1286 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0840    1.3940    0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1318    0.7771   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7483   -0.3497    0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7356    0.9629    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980   -1.9730    1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0078   -1.6928    2.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3946   -0.4952    2.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717   -2.4675    0.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5132   -2.1232   -0.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5330   -2.2798   -1.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3750   -0.3458   -1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0316   -0.1808   -2.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8401    1.2725   -1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2905    2.7879   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4944    0.2816    1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    1.8600    2.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9740    2.6327    0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483    2.3187    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4288   -0.5778   -2.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8599   -2.2638   -1.8563 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 16  4  1  0
 13  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Eremopetasidione	MeSH

Chemical Formula

C₁₄H₂₀O₃

Average Molecular Weight

236.3068

Monoisotopic Molecular Weight

236.141244506

IUPAC Name

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

Traditional Name

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

CAS Registry Number

163135-94-2

SMILES

CC1C(O)CCC2CC(=O)C(=CC12C)C(C)=O

InChI Identifier

InChI=1S/C14H20O3/c1-8-12(16)5-4-10-6-13(17)11(9(2)15)7-14(8,10)3/h7-8,10,12,16H,4-6H2,1-3H3

InChI Key

ZKOZDFWTXYIUDZ-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 alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0040778)

Cellular substructure

Extracellular (HMDB: HMDB0040778)
Cytoplasm (HMDB: HMDB0040778)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040778)

Source

Endogenous

Endogenous (HMDB: HMDB0040778)

Plant

Plant (HMDB: HMDB0040778)

Animal

Animal (HMDB: HMDB0040778)

Exogenous

Food

Food (HMDB: HMDB0040778)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0040778)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0040778)

Cellular process

Cell signaling (HMDB: HMDB0040778)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0040778)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0040778)

Nutrient

Nutrient (HMDB: HMDB0040778)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040778)

Emulsifier (HMDB: HMDB0040778)

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	5178 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	0.5 g/L	ALOGPS
logP	1.69	ALOGPS
logP	1.68	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	18.42	ChemAxon
pKa (Strongest Basic)	-0.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.08 m³·mol⁻¹	ChemAxon
Polarizability	26.01 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	155.818	31661259
DarkChem	[M-H]-	154.371	31661259
DeepCCS	[M-2H]-	186.382	30932474
DeepCCS	[M+Na]+	161.381	30932474
AllCCS	[M+H]+	154.6	32859911
AllCCS	[M+H-H2O]+	150.8	32859911
AllCCS	[M+NH4]+	158.1	32859911
AllCCS	[M+Na]+	159.1	32859911
AllCCS	[M-H]-	160.4	32859911
AllCCS	[M+Na-2H]-	160.7	32859911
AllCCS	[M+HCOO]-	161.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Eremopetasidione	CC1C(O)CCC2CC(=O)C(=CC12C)C(C)=O	2928.9	Standard polar	33892256
Eremopetasidione	CC1C(O)CCC2CC(=O)C(=CC12C)C(C)=O	1800.3	Standard non polar	33892256
Eremopetasidione	CC1C(O)CCC2CC(=O)C(=CC12C)C(C)=O	1977.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Eremopetasidione,1TMS,isomer #1	CC(=O)C1=CC2(C)C(CCC(O[Si](C)(C)C)C2C)CC1=O	2101.0	Semi standard non polar	33892256
Eremopetasidione,1TMS,isomer #2	CC(=O)C1=CC2(C)C(C=C1O[Si](C)(C)C)CCC(O)C2C	2194.2	Semi standard non polar	33892256
Eremopetasidione,1TMS,isomer #3	C=C(O[Si](C)(C)C)C1=CC2(C)C(CCC(O)C2C)CC1=O	2186.3	Semi standard non polar	33892256
Eremopetasidione,2TMS,isomer #1	CC(=O)C1=CC2(C)C(C=C1O[Si](C)(C)C)CCC(O[Si](C)(C)C)C2C	2159.7	Semi standard non polar	33892256
Eremopetasidione,2TMS,isomer #1	CC(=O)C1=CC2(C)C(C=C1O[Si](C)(C)C)CCC(O[Si](C)(C)C)C2C	1995.6	Standard non polar	33892256
Eremopetasidione,2TMS,isomer #2	C=C(O[Si](C)(C)C)C1=CC2(C)C(CCC(O[Si](C)(C)C)C2C)CC1=O	2140.2	Semi standard non polar	33892256
Eremopetasidione,2TMS,isomer #2	C=C(O[Si](C)(C)C)C1=CC2(C)C(CCC(O[Si](C)(C)C)C2C)CC1=O	2037.9	Standard non polar	33892256
Eremopetasidione,2TMS,isomer #3	C=C(O[Si](C)(C)C)C1=CC2(C)C(C=C1O[Si](C)(C)C)CCC(O)C2C	2220.4	Semi standard non polar	33892256
Eremopetasidione,2TMS,isomer #3	C=C(O[Si](C)(C)C)C1=CC2(C)C(C=C1O[Si](C)(C)C)CCC(O)C2C	2137.8	Standard non polar	33892256
Eremopetasidione,3TMS,isomer #1	C=C(O[Si](C)(C)C)C1=CC2(C)C(C=C1O[Si](C)(C)C)CCC(O[Si](C)(C)C)C2C	2190.7	Semi standard non polar	33892256
Eremopetasidione,3TMS,isomer #1	C=C(O[Si](C)(C)C)C1=CC2(C)C(C=C1O[Si](C)(C)C)CCC(O[Si](C)(C)C)C2C	2115.4	Standard non polar	33892256
Eremopetasidione,1TBDMS,isomer #1	CC(=O)C1=CC2(C)C(CCC(O[Si](C)(C)C(C)(C)C)C2C)CC1=O	2361.5	Semi standard non polar	33892256
Eremopetasidione,1TBDMS,isomer #2	CC(=O)C1=CC2(C)C(C=C1O[Si](C)(C)C(C)(C)C)CCC(O)C2C	2429.8	Semi standard non polar	33892256
Eremopetasidione,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(CCC(O)C2C)CC1=O	2433.9	Semi standard non polar	33892256
Eremopetasidione,2TBDMS,isomer #1	CC(=O)C1=CC2(C)C(C=C1O[Si](C)(C)C(C)(C)C)CCC(O[Si](C)(C)C(C)(C)C)C2C	2619.7	Semi standard non polar	33892256
Eremopetasidione,2TBDMS,isomer #1	CC(=O)C1=CC2(C)C(C=C1O[Si](C)(C)C(C)(C)C)CCC(O[Si](C)(C)C(C)(C)C)C2C	2416.4	Standard non polar	33892256
Eremopetasidione,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(CCC(O[Si](C)(C)C(C)(C)C)C2C)CC1=O	2612.0	Semi standard non polar	33892256
Eremopetasidione,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(CCC(O[Si](C)(C)C(C)(C)C)C2C)CC1=O	2473.5	Standard non polar	33892256
Eremopetasidione,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(C=C1O[Si](C)(C)C(C)(C)C)CCC(O)C2C	2702.6	Semi standard non polar	33892256
Eremopetasidione,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(C=C1O[Si](C)(C)C(C)(C)C)CCC(O)C2C	2532.3	Standard non polar	33892256
Eremopetasidione,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(C=C1O[Si](C)(C)C(C)(C)C)CCC(O[Si](C)(C)C(C)(C)C)C2C	2894.9	Semi standard non polar	33892256
Eremopetasidione,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(C=C1O[Si](C)(C)C(C)(C)C)CCC(O[Si](C)(C)C(C)(C)C)C2C	2674.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Eremopetasidione GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1950000000-4c47778cd5a65b5befa5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eremopetasidione GC-MS (1 TMS) - 70eV, Positive	splash10-004l-4590000000-aa7a846332de724c07e4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eremopetasidione 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 - Eremopetasidione 10V, Positive-QTOF	splash10-014r-0090000000-328dda00bf74e923b291	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremopetasidione 20V, Positive-QTOF	splash10-0gbi-0890000000-21b9f37333ca3d2d183e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremopetasidione 40V, Positive-QTOF	splash10-014s-6900000000-4fd5d2cf073bcaa8951e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremopetasidione 10V, Negative-QTOF	splash10-000i-0090000000-c9a989d8ad9a29363c01	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremopetasidione 20V, Negative-QTOF	splash10-000i-0190000000-b5aac5277d0e8d5c40cd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremopetasidione 40V, Negative-QTOF	splash10-002f-2950000000-6b8e095bfeb18ee62451	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremopetasidione 10V, Positive-QTOF	splash10-00kr-0190000000-16911a2112cd3c90a405	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremopetasidione 20V, Positive-QTOF	splash10-0a6r-1910000000-0313a2eb14b3ba08b6e7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremopetasidione 40V, Positive-QTOF	splash10-014i-8900000000-4d2854863342440c6619	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremopetasidione 10V, Negative-QTOF	splash10-000i-0090000000-0e0b07ef47a35db161f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremopetasidione 20V, Negative-QTOF	splash10-000i-0090000000-9240b0ce95c05ff0c704	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremopetasidione 40V, Negative-QTOF	splash10-0gbi-1970000000-2df5067eefa221030dbc	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB020594

KNApSAcK ID

Not Available

Chemspider ID

35015025

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72755911

PDB ID

Not Available

ChEBI ID

174214

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1886311

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 Eremopetasidione (HMDB0040778)

MOL for HMDB0040778 (Eremopetasidione)

3D MOL for HMDB0040778 (Eremopetasidione)

3D SDF for HMDB0040778 (Eremopetasidione)

3D-SDF for HMDB0040778 (Eremopetasidione)

PDB for HMDB0040778 (Eremopetasidione)

3D PDB for HMDB0040778 (Eremopetasidione)

SMILES for HMDB0040778 (Eremopetasidione)

INCHI for HMDB0040778 (Eremopetasidione)

Structure for HMDB0040778 (Eremopetasidione)

3D Structure for HMDB0040778 (Eremopetasidione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra