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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:51:03 UTC

Update Date

2022-03-07 02:54:39 UTC

HMDB ID

HMDB0035827

Secondary Accession Numbers

HMDB35827

Metabolite Identification

Common Name

Aubergenone

Description

Aubergenone belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Based on a literature review a small amount of articles have been published on Aubergenone.

Structure

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

HMDB0035827
     RDKit          3D
Aubergenone
 41 42  0  0  0  0  0  0  0  0999 V2000
   -1.9120    2.1961    1.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8630    1.4548   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2118    1.0035   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066    1.7030   -0.4719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -0.2835   -1.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5221   -1.2523   -1.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584   -1.0152   -0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1108   -1.1122    1.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3469   -2.0416   -0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9801   -1.4266   -0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3621   -0.3919    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7005    0.2211    0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7914   -0.8248    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7246    0.9770   -1.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126    1.1333    1.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2805    0.6376    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8444    0.3379   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900    2.5876    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441    1.6142    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5447    3.1082    0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5729    2.2445   -1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547   -0.4609   -2.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169   -2.2030   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0945   -0.5998    1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3057   -2.1560    1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4707   -0.6076    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2683   -2.6734    0.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6221   -2.7177   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387   -2.2552   -0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0655   -1.0770   -1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954   -0.9566    1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4317   -1.7608    0.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0699   -1.1072   -0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7298   -0.4544    0.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1990    1.9627   -1.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162    0.3923   -1.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8041    1.2509   -1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6281    1.8244    0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0364    0.7939    1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7266    1.6164    0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3998    0.3184   -1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  1  0
 16 17  1  0
 17  2  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
M  END

  Mrv0541 05061308442D          

 17 18  0  0  0  0            999 V2000
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.1270    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    3.5724    1.2375    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   -0.4125    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
    4.2868    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 10  1  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14 11  1  0  0  0  0
 15  4  1  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035827

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CC(CCC2(C)C=CC1=O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-10-12-9-11(14(2,3)17)5-7-15(12,4)8-6-13(10)16/h6,8,10-12,17H,5,7,9H2,1-4H3

> <INCHI_KEY>
MSSWKGZMPUXALD-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.65555525310669

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
2.9539466753333325

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.24787634115214

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9407363492797732

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
70.34459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0035827
     RDKit          3D
Aubergenone
 41 42  0  0  0  0  0  0  0  0999 V2000
   -1.9120    2.1961    1.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8630    1.4548   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2118    1.0035   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066    1.7030   -0.4719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -0.2835   -1.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5221   -1.2523   -1.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584   -1.0152   -0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1108   -1.1122    1.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3469   -2.0416   -0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9801   -1.4266   -0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3621   -0.3919    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7005    0.2211    0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7914   -0.8248    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7246    0.9770   -1.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126    1.1333    1.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2805    0.6376    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8444    0.3379   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900    2.5876    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441    1.6142    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5447    3.1082    0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5729    2.2445   -1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547   -0.4609   -2.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169   -2.2030   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0945   -0.5998    1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3057   -2.1560    1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4707   -0.6076    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2683   -2.6734    0.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6221   -2.7177   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387   -2.2552   -0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0655   -1.0770   -1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954   -0.9566    1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4317   -1.7608    0.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0699   -1.1072   -0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7298   -0.4544    0.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1990    1.9627   -1.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162    0.3923   -1.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8041    1.2509   -1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6281    1.8244    0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0364    0.7939    1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7266    1.6164    0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3998    0.3184   -1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  1  0
 16 17  1  0
 17  2  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.104  -2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.564   0.564   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    7   11                                                       
CONECT    6    8   13                                                       
CONECT    7    5   15                                                       
CONECT    8    6   15                                                       
CONECT    9   11   12                                                       
CONECT   10    1   12   13                                                  
CONECT   11    5    9   14                                                  
CONECT   12    9   10   15                                                  
CONECT   13    6   10   16                                                  
CONECT   14    2    3   11   17                                             
CONECT   15    4    7    8   12                                             
CONECT   16   13                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0035827
HETATM    1  C1  UNL     1      -1.912   2.196   1.028  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.863   1.455  -0.298  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.212   1.003  -0.693  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.207   1.703  -0.472  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.360  -0.284  -1.352  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.522  -1.252  -1.053  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.458  -1.015  -0.064  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.111  -1.112   1.305  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.347  -2.042  -0.206  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.980  -1.427  -0.535  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.362  -0.392   0.503  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.701   0.221   0.186  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.791  -0.825   0.156  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.725   0.977  -1.099  1.00  0.00           C  
HETATM   15  O2  UNL     1       3.013   1.133   1.212  1.00  0.00           O  
HETATM   16  C14 UNL     1       0.281   0.638   0.661  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.844   0.338  -0.292  1.00  0.00           C  
HETATM   18  H1  UNL     1      -0.890   2.588   1.239  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.344   1.614   1.840  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.545   3.108   0.829  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.573   2.245  -1.054  1.00  0.00           H  
HETATM   22  H5  UNL     1      -4.155  -0.461  -2.090  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.617  -2.203  -1.528  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.095  -0.600   1.299  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.306  -2.156   1.597  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.471  -0.608   2.070  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.268  -2.673   0.704  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.622  -2.718  -1.039  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.739  -2.255  -0.417  1.00  0.00           H  
HETATM   30  H13 UNL     1       1.066  -1.077  -1.563  1.00  0.00           H  
HETATM   31  H14 UNL     1       1.495  -0.957   1.464  1.00  0.00           H  
HETATM   32  H15 UNL     1       3.432  -1.761   0.640  1.00  0.00           H  
HETATM   33  H16 UNL     1       4.070  -1.107  -0.884  1.00  0.00           H  
HETATM   34  H17 UNL     1       4.730  -0.454   0.634  1.00  0.00           H  
HETATM   35  H18 UNL     1       2.199   1.963  -1.051  1.00  0.00           H  
HETATM   36  H19 UNL     1       2.416   0.392  -1.974  1.00  0.00           H  
HETATM   37  H20 UNL     1       3.804   1.251  -1.287  1.00  0.00           H  
HETATM   38  H21 UNL     1       3.628   1.824   0.881  1.00  0.00           H  
HETATM   39  H22 UNL     1      -0.036   0.794   1.700  1.00  0.00           H  
HETATM   40  H23 UNL     1       0.727   1.616   0.316  1.00  0.00           H  
HETATM   41  H24 UNL     1      -0.400   0.318  -1.315  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   17   21
CONECT    3    4    4    5
CONECT    5    6    6   22
CONECT    6    7   23
CONECT    7    8    9   17
CONECT    8   24   25   26
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   12   16   31
CONECT   12   13   14   15
CONECT   13   32   33   34
CONECT   14   35   36   37
CONECT   15   38
CONECT   16   17   39   40
CONECT   17   41
END

HMDB0035827
     RDKit          3D
Aubergenone
 41 42  0  0  0  0  0  0  0  0999 V2000
   -1.9120    2.1961    1.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8630    1.4548   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2118    1.0035   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066    1.7030   -0.4719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -0.2835   -1.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5221   -1.2523   -1.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584   -1.0152   -0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1108   -1.1122    1.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3469   -2.0416   -0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9801   -1.4266   -0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3621   -0.3919    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7005    0.2211    0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7914   -0.8248    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7246    0.9770   -1.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126    1.1333    1.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2805    0.6376    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8444    0.3379   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900    2.5876    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441    1.6142    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5447    3.1082    0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5729    2.2445   -1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547   -0.4609   -2.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169   -2.2030   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0945   -0.5998    1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3057   -2.1560    1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4707   -0.6076    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2683   -2.6734    0.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6221   -2.7177   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387   -2.2552   -0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0655   -1.0770   -1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954   -0.9566    1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4317   -1.7608    0.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0699   -1.1072   -0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7298   -0.4544    0.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1990    1.9627   -1.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162    0.3923   -1.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8041    1.2509   -1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6281    1.8244    0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0364    0.7939    1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7266    1.6164    0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3998    0.3184   -1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  1  0
 16 17  1  0
 17  2  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Mangeudesmenone	HMDB
[1R-(1alpha,4Aalpha,7alpha,8abeta)]-4a,5,6,7,8,8a-hexahydro-7-(1-hydroxy-1-methylethyl)-1,4a-dimethyl-2(1H)-naphthalenone	HMDB

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.3499

Monoisotopic Molecular Weight

236.177630012

IUPAC Name

7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one

Traditional Name

7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-one

CAS Registry Number

69427-35-6

SMILES

CC1C2CC(CCC2(C)C=CC1=O)C(C)(C)O

InChI Identifier

InChI=1S/C15H24O2/c1-10-12-9-11(14(2,3)17)5-7-15(12,4)8-6-13(10)16/h6,8,10-12,17H,5,7,9H2,1-4H3

InChI Key

MSSWKGZMPUXALD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Cyclohexenone
Tertiary alcohol
Cyclic ketone
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

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035827)

Source

Endogenous

Endogenous (HMDB: HMDB0035827)

Plant

Plant (HMDB: HMDB0035827)

Animal

Animal (HMDB: HMDB0035827)

Exogenous

Food

Food (HMDB: HMDB0035827)

Vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0035827)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035827)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035827)

Lipid metabolism pathway (HMDB: HMDB0035827)

Cellular process

Cell signaling (HMDB: HMDB0035827)

Biochemical process

Lipid transport (HMDB: HMDB0035827)

Role

Biological role

Energy source (HMDB: HMDB0035827)
Phytoalexin (HMDB: HMDB0035827)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035827)

Agriculture

Pesticide (HMDB: HMDB0035827)

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	0.078 g/L	ALOGPS
logP	2.93	ALOGPS
logP	2.95	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	19.25	ChemAxon
pKa (Strongest Basic)	-0.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.34 m³·mol⁻¹	ChemAxon
Polarizability	27.66 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]+	157.129	31661259
DarkChem	[M-H]-	153.953	31661259
DeepCCS	[M+H]+	163.54	30932474
DeepCCS	[M-H]-	161.182	30932474
DeepCCS	[M-2H]-	194.094	30932474
DeepCCS	[M+Na]+	169.633	30932474
AllCCS	[M+H]+	155.1	32859911
AllCCS	[M+H-H2O]+	151.4	32859911
AllCCS	[M+NH4]+	158.6	32859911
AllCCS	[M+Na]+	159.6	32859911
AllCCS	[M-H]-	163.3	32859911
AllCCS	[M+Na-2H]-	163.8	32859911
AllCCS	[M+HCOO]-	164.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aubergenone	CC1C2CC(CCC2(C)C=CC1=O)C(C)(C)O	2573.5	Standard polar	33892256
Aubergenone	CC1C2CC(CCC2(C)C=CC1=O)C(C)(C)O	1846.2	Standard non polar	33892256
Aubergenone	CC1C2CC(CCC2(C)C=CC1=O)C(C)(C)O	1891.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aubergenone,1TMS,isomer #1	CC1C(=O)C=CC2(C)CCC(C(C)(C)O[Si](C)(C)C)CC12	2064.2	Semi standard non polar	33892256
Aubergenone,1TMS,isomer #2	CC1=C(O[Si](C)(C)C)C=CC2(C)CCC(C(C)(C)O)CC12	2124.2	Semi standard non polar	33892256
Aubergenone,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C=CC2(C)CCC(C(C)(C)O[Si](C)(C)C)CC12	2121.1	Semi standard non polar	33892256
Aubergenone,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C=CC2(C)CCC(C(C)(C)O[Si](C)(C)C)CC12	2041.5	Standard non polar	33892256
Aubergenone,1TBDMS,isomer #1	CC1C(=O)C=CC2(C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)CC12	2333.0	Semi standard non polar	33892256
Aubergenone,1TBDMS,isomer #2	CC1=C(O[Si](C)(C)C(C)(C)C)C=CC2(C)CCC(C(C)(C)O)CC12	2362.5	Semi standard non polar	33892256
Aubergenone,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C=CC2(C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)CC12	2577.0	Semi standard non polar	33892256
Aubergenone,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C=CC2(C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)CC12	2522.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Aubergenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-3950000000-f6a32864344582bb94e4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aubergenone GC-MS (1 TMS) - 70eV, Positive	splash10-003l-5590000000-392d36b59728e6f9ed3d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aubergenone 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 - Aubergenone 10V, Positive-QTOF	splash10-014r-0290000000-03816e1c3e313355b05e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aubergenone 20V, Positive-QTOF	splash10-00p0-1940000000-817dcda0076697396ca5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aubergenone 40V, Positive-QTOF	splash10-0gc1-9710000000-c4b96a33197de6a924cf	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aubergenone 10V, Negative-QTOF	splash10-000i-0090000000-7586dd0d73ed89677ad2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aubergenone 20V, Negative-QTOF	splash10-002r-0390000000-022a7378257ac0859d48	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aubergenone 40V, Negative-QTOF	splash10-02vi-2960000000-879779dbdcb4ca6510f3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aubergenone 10V, Positive-QTOF	splash10-0gbi-0390000000-87fe8281248f42496d53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aubergenone 20V, Positive-QTOF	splash10-000i-3930000000-72b9a28b8aebb761a4fd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aubergenone 40V, Positive-QTOF	splash10-008c-9400000000-cf776e3f7223796666fb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aubergenone 10V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aubergenone 20V, Negative-QTOF	splash10-000i-0090000000-429531043a4aef925aee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aubergenone 40V, Negative-QTOF	splash10-067r-0290000000-9685bb5bcc173b218df9	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

FDB014591

KNApSAcK ID

C00012854

Chemspider ID

35014028

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15601417

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 Aubergenone (HMDB0035827)

MOL for HMDB0035827 (Aubergenone)

3D MOL for HMDB0035827 (Aubergenone)

3D SDF for HMDB0035827 (Aubergenone)

3D-SDF for HMDB0035827 (Aubergenone)

PDB for HMDB0035827 (Aubergenone)

3D PDB for HMDB0035827 (Aubergenone)

SMILES for HMDB0035827 (Aubergenone)

INCHI for HMDB0035827 (Aubergenone)

Structure for HMDB0035827 (Aubergenone)

3D Structure for HMDB0035827 (Aubergenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra