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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:25:48 UTC

Update Date

2022-03-07 02:55:38 UTC

HMDB ID

HMDB0038146

Secondary Accession Numbers

HMDB38146

Metabolite Identification

Common Name

Calacone

Description

Calacone belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a small amount of articles have been published on Calacone.

Structure

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

HMDB0038146
     RDKit          3D
Calacone
 40 40  0  0  0  0  0  0  0  0999 V2000
    2.7273    0.8385   -1.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9062    0.7128   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5389    1.8761    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5357   -0.5168    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4351   -0.3967    1.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    0.0069    0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589   -0.7638    0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528   -2.1457    1.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583   -3.1248   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682   -2.3061    2.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2379   -0.2836   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1016    0.6165   -1.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522    1.5789   -1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167    3.0181   -1.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0893    1.3519    0.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509    2.3529    0.5700 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0130    1.7121   -2.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2739    0.0151   -2.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154    1.8682    1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1765    2.7852   -0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6459    1.7851    0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3467   -1.3008   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4584   -0.8269    0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885    0.4441    1.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4119   -1.2708    1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0041   -2.5418    1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5720   -3.1518   -0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1576   -4.1367    0.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9990   -2.9311   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646   -2.5898    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6235   -3.1343    2.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0905   -1.3783    2.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7871    0.2122    0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8268   -1.1619   -0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585    0.0229   -2.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0311    1.2223   -1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3038    1.4609   -2.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5477    3.6501   -1.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3006    3.1805   -1.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6568    3.2506   -0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
M  END


  Mrv0541 05061310152D          

 16 16  0  0  0  0            999 V2000
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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    0.8250    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
    0.7145    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 10  6  1  0  0  0  0
 11  3  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038146

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=C(CCC(C)=C)C(=O)C(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-10(2)6-8-14-13(11(3)4)9-7-12(5)15(14)16/h11-12H,1,6-9H2,2-5H3

> <INCHI_KEY>
GPXJKVFRKZAYCC-UHFFFAOYSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.08414749121802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-methyl-2-(3-methylbut-3-en-1-yl)-3-(propan-2-yl)cyclohex-2-en-1-one

> <ALOGPS_LOGP>
4.36

> <JCHEM_LOGP>
4.672582835333333

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.831612782655072

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
69.83299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-isopropyl-6-methyl-2-(3-methylbut-3-en-1-yl)cyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038146
     RDKit          3D
Calacone
 40 40  0  0  0  0  0  0  0  0999 V2000
    2.7273    0.8385   -1.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9062    0.7128   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5389    1.8761    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5357   -0.5168    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4351   -0.3967    1.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    0.0069    0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589   -0.7638    0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528   -2.1457    1.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583   -3.1248   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682   -2.3061    2.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2379   -0.2836   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1016    0.6165   -1.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522    1.5789   -1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167    3.0181   -1.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0893    1.3519    0.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509    2.3529    0.5700 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0130    1.7121   -2.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2739    0.0151   -2.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154    1.8682    1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1765    2.7852   -0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6459    1.7851    0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3467   -1.3008   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4584   -0.8269    0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885    0.4441    1.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4119   -1.2708    1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0041   -2.5418    1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5720   -3.1518   -0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1576   -4.1367    0.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9990   -2.9311   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646   -2.5898    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6235   -3.1343    2.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0905   -1.3783    2.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7871    0.2122    0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8268   -1.1619   -0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585    0.0229   -2.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0311    1.2223   -1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3038    1.4609   -2.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5477    3.6501   -1.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3006    3.1805   -1.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6568    3.2506   -0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  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      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   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   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   11                                                            
CONECT    5   12                                                            
CONECT    6    8   10                                                       
CONECT    7    9   12                                                       
CONECT    8    6   14                                                       
CONECT    9    7   13                                                       
CONECT   10    1    2    6                                                  
CONECT   11    3    4   13                                                  
CONECT   12    5    7   15                                                  
CONECT   13    9   11   14                                                  
CONECT   14    8   13   15                                                  
CONECT   15   12   14   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0038146
HETATM    1  C1  UNL     1       2.727   0.839  -1.915  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.906   0.713  -0.592  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.539   1.876   0.127  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.536  -0.517   0.127  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.435  -0.397   1.127  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.127   0.007   0.582  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.959  -0.764   0.546  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.953  -2.146   1.067  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.458  -3.125  -0.012  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.968  -2.306   2.205  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.238  -0.284  -0.026  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.102   0.616  -1.203  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.952   1.579  -1.144  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.417   3.018  -1.128  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.089   1.352   0.042  1.00  0.00           C  
HETATM   16  O1  UNL     1       0.451   2.353   0.570  1.00  0.00           O  
HETATM   17  H1  UNL     1       3.013   1.712  -2.448  1.00  0.00           H  
HETATM   18  H2  UNL     1       2.274   0.015  -2.456  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.215   1.868   1.187  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.177   2.785  -0.359  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.646   1.785   0.097  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.347  -1.301  -0.636  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.458  -0.827   0.704  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.789   0.444   1.831  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.412  -1.271   1.802  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.004  -2.542   1.381  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.572  -3.152  -0.025  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.158  -4.137   0.335  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.999  -2.931  -0.978  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.965  -2.590   1.805  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.624  -3.134   2.867  1.00  0.00           H  
HETATM   32  H16 UNL     1      -2.090  -1.378   2.768  1.00  0.00           H  
HETATM   33  H17 UNL     1      -2.787   0.212   0.809  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.827  -1.162  -0.351  1.00  0.00           H  
HETATM   35  H19 UNL     1      -2.058   0.023  -2.141  1.00  0.00           H  
HETATM   36  H20 UNL     1      -3.031   1.222  -1.272  1.00  0.00           H  
HETATM   37  H21 UNL     1      -0.304   1.461  -2.036  1.00  0.00           H  
HETATM   38  H22 UNL     1      -0.548   3.650  -1.425  1.00  0.00           H  
HETATM   39  H23 UNL     1      -2.301   3.181  -1.777  1.00  0.00           H  
HETATM   40  H24 UNL     1      -1.657   3.251  -0.055  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3    4
CONECT    3   19   20   21
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7    7   15
CONECT    7    8   11
CONECT    8    9   10   26
CONECT    9   27   28   29
CONECT   10   30   31   32
CONECT   11   12   33   34
CONECT   12   13   35   36
CONECT   13   14   15   37
CONECT   14   38   39   40
CONECT   15   16   16
END

HMDB0038146
     RDKit          3D
Calacone
 40 40  0  0  0  0  0  0  0  0999 V2000
    2.7273    0.8385   -1.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9062    0.7128   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5389    1.8761    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5357   -0.5168    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4351   -0.3967    1.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    0.0069    0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589   -0.7638    0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528   -2.1457    1.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583   -3.1248   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682   -2.3061    2.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2379   -0.2836   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1016    0.6165   -1.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522    1.5789   -1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167    3.0181   -1.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0893    1.3519    0.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509    2.3529    0.5700 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0130    1.7121   -2.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2739    0.0151   -2.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154    1.8682    1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1765    2.7852   -0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6459    1.7851    0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3467   -1.3008   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4584   -0.8269    0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885    0.4441    1.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4119   -1.2708    1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0041   -2.5418    1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5720   -3.1518   -0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1576   -4.1367    0.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9990   -2.9311   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646   -2.5898    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6235   -3.1343    2.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0905   -1.3783    2.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7871    0.2122    0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8268   -1.1619   -0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585    0.0229   -2.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0311    1.2223   -1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3038    1.4609   -2.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5477    3.6501   -1.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3006    3.1805   -1.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6568    3.2506   -0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O

Average Molecular Weight

220.3505

Monoisotopic Molecular Weight

220.18271539

IUPAC Name

6-methyl-2-(3-methylbut-3-en-1-yl)-3-(propan-2-yl)cyclohex-2-en-1-one

Traditional Name

3-isopropyl-6-methyl-2-(3-methylbut-3-en-1-yl)cyclohex-2-en-1-one

CAS Registry Number

Not Available

SMILES

CC(C)C1=C(CCC(C)=C)C(=O)C(C)CC1

InChI Identifier

InChI=1S/C15H24O/c1-10(2)6-8-14-13(11(3)4)9-7-12(5)15(14)16/h11-12H,1,6-9H2,2-5H3

InChI Key

GPXJKVFRKZAYCC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038146)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038146)

Source

Endogenous

Endogenous (HMDB: HMDB0038146)

Plant

Plant (HMDB: HMDB0038146)

Animal

Animal (HMDB: HMDB0038146)

Exogenous

Food

Food (HMDB: HMDB0038146)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0038146)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0038146)

Cellular process

Cell signaling (HMDB: HMDB0038146)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0038146)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0038146)

Nutrient

Nutrient (HMDB: HMDB0038146)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038146)

Emulsifier (HMDB: HMDB0038146)

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	0.075 g/L	ALOGPS
logP	4.36	ALOGPS
logP	4.67	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.83 m³·mol⁻¹	ChemAxon
Polarizability	27.08 Å³	ChemAxon
Number of Rings	1	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]+	155.147	31661259
DarkChem	[M-H]-	150.233	31661259
DeepCCS	[M+H]+	161.987	30932474
DeepCCS	[M-H]-	159.629	30932474
DeepCCS	[M-2H]-	192.548	30932474
DeepCCS	[M+Na]+	168.08	30932474
AllCCS	[M+H]+	152.7	32859911
AllCCS	[M+H-H2O]+	148.9	32859911
AllCCS	[M+NH4]+	156.1	32859911
AllCCS	[M+Na]+	157.1	32859911
AllCCS	[M-H]-	159.6	32859911
AllCCS	[M+Na-2H]-	160.4	32859911
AllCCS	[M+HCOO]-	161.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Calacone	CC(C)C1=C(CCC(C)=C)C(=O)C(C)CC1	2074.8	Standard polar	33892256
Calacone	CC(C)C1=C(CCC(C)=C)C(=O)C(C)CC1	1657.2	Standard non polar	33892256
Calacone	CC(C)C1=C(CCC(C)=C)C(=O)C(C)CC1	1620.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Calacone,1TMS,isomer #1	C=C(C)CCC1=C(C(C)C)CCC(C)=C1O[Si](C)(C)C	1691.8	Semi standard non polar	33892256
Calacone,1TMS,isomer #1	C=C(C)CCC1=C(C(C)C)CCC(C)=C1O[Si](C)(C)C	1737.5	Standard non polar	33892256
Calacone,1TBDMS,isomer #1	C=C(C)CCC1=C(C(C)C)CCC(C)=C1O[Si](C)(C)C(C)(C)C	1914.5	Semi standard non polar	33892256
Calacone,1TBDMS,isomer #1	C=C(C)CCC1=C(C(C)C)CCC(C)=C1O[Si](C)(C)C(C)(C)C	1925.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Calacone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-4920000000-9e2bb2ecc228e7c7e640	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calacone 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 - Calacone 10V, Positive-QTOF	splash10-00di-0490000000-8a4a2b66420d2442c423	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calacone 20V, Positive-QTOF	splash10-06di-3920000000-bb7494ef181f929e028d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calacone 40V, Positive-QTOF	splash10-0aor-9400000000-31675d50f16b081268a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calacone 10V, Negative-QTOF	splash10-014i-0090000000-fa6ef1a62964ce29b6dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calacone 20V, Negative-QTOF	splash10-014i-0190000000-3b84c7858aefe9786307	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calacone 40V, Negative-QTOF	splash10-0w29-2920000000-a5eab7b069c0db41ac5e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calacone 10V, Positive-QTOF	splash10-00di-0910000000-1a760976d910ab4ca9aa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calacone 20V, Positive-QTOF	splash10-00xr-2910000000-07ee4a3b331db708c5c2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calacone 40V, Positive-QTOF	splash10-0006-9200000000-39684a895489aa9307cf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calacone 10V, Negative-QTOF	splash10-014i-0090000000-4af4c4ee1c4acef7e18b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calacone 20V, Negative-QTOF	splash10-014i-0090000000-c9aea3cc46ebcbd58e37	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calacone 40V, Negative-QTOF	splash10-01ot-1910000000-e3be646586430400e163	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB017374

KNApSAcK ID

C00020166

Chemspider ID

4474882

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5315607

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 Calacone (HMDB0038146)

MOL for HMDB0038146 (Calacone)

3D MOL for HMDB0038146 (Calacone)

3D SDF for HMDB0038146 (Calacone)

3D-SDF for HMDB0038146 (Calacone)

PDB for HMDB0038146 (Calacone)

3D PDB for HMDB0038146 (Calacone)

SMILES for HMDB0038146 (Calacone)

INCHI for HMDB0038146 (Calacone)

Structure for HMDB0038146 (Calacone)

3D Structure for HMDB0038146 (Calacone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra