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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:44:51 UTC

Update Date

2022-03-07 02:54:58 UTC

HMDB ID

HMDB0036589

Secondary Accession Numbers

HMDB36589

Metabolite Identification

Common Name

1,2-Dehydro-alpha-cyperone

Description

1,2-Dehydro-alpha-cyperone 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 1,2-Dehydro-alpha-cyperone.

Structure

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

HMDB0036589
     RDKit          3D
1,2-Dehydro-alpha-cyperone
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.2654   -1.5661    0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7392   -0.3517    0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    0.7287    0.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3827   -0.1174   -0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8524   -1.3494   -0.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5053   -1.0422   -1.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4636   -0.7545   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5235   -1.9157    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8141   -0.5935   -0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4744    0.5286   -0.8763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095    1.6993   -0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5271    2.7938   -0.1363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    1.6150    0.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9263    2.7868    1.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460    0.4715    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4522    0.4064    0.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2619   -1.7357    0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639   -2.4389   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3035    1.0664    0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1141    0.2547    1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187    1.5880    1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245    0.6838   -1.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5606   -1.6831   -1.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7780   -2.1395   -0.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8606   -1.7957   -2.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3844   -0.0857   -2.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5941   -2.8706   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619   -1.8399    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850   -1.9804    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -1.4639   -1.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4904    0.6222   -1.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613    3.1706    0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6667    3.6275    1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5753    2.5586    2.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230    1.4093    1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3690   -0.2871    1.6449 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  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16  4  1  0
 15  7  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
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
M  END


  Mrv0541 05061309132D          

 16 17  0  0  0  0            999 V2000
    0.0000    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
    3.5724   -1.2375    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
    0.7145   -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
    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
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  5  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  2  0  0  0  0
 14  6  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 13  1  0  0  0  0
 16 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036589

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1CCC2(C)C=CC(=O)C(C)=C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O/c1-10(2)12-5-7-15(4)8-6-14(16)11(3)13(15)9-12/h6,8,12H,1,5,7,9H2,2-4H3

> <INCHI_KEY>
YFZICPBAKZACEG-UHFFFAOYSA-N

> <FORMULA>
C15H20O

> <MOLECULAR_WEIGHT>
216.3187

> <EXACT_MASS>
216.151415262

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.58071005255421

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4a-dimethyl-7-(prop-1-en-2-yl)-2,4a,5,6,7,8-hexahydronaphthalen-2-one

> <ALOGPS_LOGP>
4.28

> <JCHEM_LOGP>
3.806191695333334

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.967917743322635

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
68.9723

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4a-dimethyl-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036589
     RDKit          3D
1,2-Dehydro-alpha-cyperone
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.2654   -1.5661    0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7392   -0.3517    0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    0.7287    0.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3827   -0.1174   -0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8524   -1.3494   -0.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5053   -1.0422   -1.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4636   -0.7545   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5235   -1.9157    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8141   -0.5935   -0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4744    0.5286   -0.8763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095    1.6993   -0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5271    2.7938   -0.1363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    1.6150    0.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9263    2.7868    1.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460    0.4715    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4522    0.4064    0.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2619   -1.7357    0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639   -2.4389   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3035    1.0664    0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1141    0.2547    1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187    1.5880    1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245    0.6838   -1.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5606   -1.6831   -1.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7780   -2.1395   -0.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8606   -1.7957   -2.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3844   -0.0857   -2.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5941   -2.8706   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619   -1.8399    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850   -1.9804    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -1.4639   -1.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4904    0.6222   -1.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613    3.1706    0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6667    3.6275    1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5753    2.5586    2.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230    1.4093    1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3690   -0.2871    1.6449 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  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16  4  1  0
 15  7  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
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   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
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   15                                                            
CONECT    5    7   12                                                       
CONECT    6    8   14                                                       
CONECT    7    5   15                                                       
CONECT    8    6   15                                                       
CONECT    9   12   13                                                       
CONECT   10    1    2   12                                                  
CONECT   11    3   13   14                                                  
CONECT   12    5    9   10                                                  
CONECT   13    9   11   15                                                  
CONECT   14    6   11   16                                                  
CONECT   15    4    7    8   13                                             
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0036589
HETATM    1  C1  UNL     1       3.265  -1.566   0.135  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.739  -0.352   0.199  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.589   0.729   0.793  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.383  -0.117  -0.298  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.852  -1.349  -0.957  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.505  -1.042  -1.570  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.464  -0.755  -0.423  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.524  -1.916   0.546  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.814  -0.594  -0.964  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.474   0.529  -0.876  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.910   1.699  -0.234  1.00  0.00           C  
HETATM   12  O1  UNL     1      -3.527   2.794  -0.136  1.00  0.00           O  
HETATM   13  C12 UNL     1      -1.571   1.615   0.325  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.926   2.787   1.002  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.946   0.472   0.215  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.452   0.406   0.784  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.262  -1.736   0.503  1.00  0.00           H  
HETATM   18  H2  UNL     1       2.764  -2.439  -0.271  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.304   1.066   0.025  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.114   0.255   1.670  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.019   1.588   1.137  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.425   0.684  -1.074  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.561  -1.683  -1.723  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.778  -2.140  -0.183  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.861  -1.796  -2.266  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.384  -0.086  -2.118  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.594  -2.871  -0.024  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.462  -1.840   1.144  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.685  -1.980   1.228  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.257  -1.464  -1.452  1.00  0.00           H  
HETATM   31  H15 UNL     1      -4.490   0.622  -1.292  1.00  0.00           H  
HETATM   32  H16 UNL     1      -0.061   3.171   0.421  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.667   3.628   1.030  1.00  0.00           H  
HETATM   34  H18 UNL     1      -0.575   2.559   2.007  1.00  0.00           H  
HETATM   35  H19 UNL     1       0.823   1.409   1.054  1.00  0.00           H  
HETATM   36  H20 UNL     1       0.369  -0.287   1.645  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3    4
CONECT    3   19   20   21
CONECT    4    5   16   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8    9   15
CONECT    8   27   28   29
CONECT    9   10   10   30
CONECT   10   11   31
CONECT   11   12   12   13
CONECT   13   14   15   15
CONECT   14   32   33   34
CONECT   15   16
CONECT   16   35   36
END

HMDB0036589
     RDKit          3D
1,2-Dehydro-alpha-cyperone
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.2654   -1.5661    0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7392   -0.3517    0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    0.7287    0.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3827   -0.1174   -0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8524   -1.3494   -0.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5053   -1.0422   -1.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4636   -0.7545   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5235   -1.9157    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8141   -0.5935   -0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4744    0.5286   -0.8763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095    1.6993   -0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5271    2.7938   -0.1363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    1.6150    0.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9263    2.7868    1.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460    0.4715    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4522    0.4064    0.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2619   -1.7357    0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639   -2.4389   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3035    1.0664    0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1141    0.2547    1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187    1.5880    1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245    0.6838   -1.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5606   -1.6831   -1.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7780   -2.1395   -0.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8606   -1.7957   -2.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3844   -0.0857   -2.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5941   -2.8706   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619   -1.8399    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850   -1.9804    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -1.4639   -1.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4904    0.6222   -1.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613    3.1706    0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6667    3.6275    1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5753    2.5586    2.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230    1.4093    1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3690   -0.2871    1.6449 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  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16  4  1  0
 15  7  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
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Dehydro-a-cyperone	Generator
1,2-Dehydro-α-cyperone	Generator
(+)-Eudesma-1,4,11-trien-3-one	HMDB
(4AS-cis)-5,6,7,8-tetrahydro-1,4a-dimethyl-7-(1-methylethenyl)-2(4ah)-naphthalenone	HMDB
1,4,11-Eudesmatrien-3-one	HMDB
1,4,11-Selinatrien-3-one	HMDB

Chemical Formula

C₁₅H₂₀O

Average Molecular Weight

216.3187

Monoisotopic Molecular Weight

216.151415262

IUPAC Name

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

Traditional Name

1,4a-dimethyl-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalen-2-one

CAS Registry Number

17081-85-5

SMILES

CC(=C)C1CCC2(C)C=CC(=O)C(C)=C2C1

InChI Identifier

InChI=1S/C15H20O/c1-10(2)12-5-7-15(4)8-6-14(16)11(3)13(15)9-12/h6,8,12H,1,5,7,9H2,2-4H3

InChI Key

YFZICPBAKZACEG-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
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036589)
Cell membrane (HMDB: HMDB0036589)

Cellular substructure

Extracellular (HMDB: HMDB0036589)
Membrane (HMDB: HMDB0036589)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036589)

Source

Endogenous

Endogenous (HMDB: HMDB0036589)

Plant

Plant (HMDB: HMDB0036589)
Coffea (HMDB: HMDB0036589)

Animal

Animal (HMDB: HMDB0036589)

Exogenous

Food

Food (HMDB: HMDB0036589)

Tea

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036589)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036589)

Cellular process

Cell signaling (HMDB: HMDB0036589)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036589)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036589)

Nutrient

Nutrient (HMDB: HMDB0036589)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036589)

Emulsifier (HMDB: HMDB0036589)

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	2.88 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	0.054 g/L	ALOGPS
logP	4.28	ALOGPS
logP	3.81	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-5	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	1	ChemAxon
Refractivity	68.97 m³·mol⁻¹	ChemAxon
Polarizability	25.58 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	151.397	31661259
DarkChem	[M-H]-	148.322	31661259
DeepCCS	[M+H]+	152.751	30932474
DeepCCS	[M-H]-	150.393	30932474
DeepCCS	[M-2H]-	183.728	30932474
DeepCCS	[M+Na]+	158.844	30932474
AllCCS	[M+H]+	149.1	32859911
AllCCS	[M+H-H2O]+	145.1	32859911
AllCCS	[M+NH4]+	152.8	32859911
AllCCS	[M+Na]+	153.8	32859911
AllCCS	[M-H]-	157.3	32859911
AllCCS	[M+Na-2H]-	157.6	32859911
AllCCS	[M+HCOO]-	158.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2-Dehydro-alpha-cyperone	CC(=C)C1CCC2(C)C=CC(=O)C(C)=C2C1	2509.0	Standard polar	33892256
1,2-Dehydro-alpha-cyperone	CC(=C)C1CCC2(C)C=CC(=O)C(C)=C2C1	1742.1	Standard non polar	33892256
1,2-Dehydro-alpha-cyperone	CC(=C)C1CCC2(C)C=CC(=O)C(C)=C2C1	1787.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dehydro-alpha-cyperone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uel-1910000000-329add8ad291a6424dd5	2017-09-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dehydro-alpha-cyperone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dehydro-alpha-cyperone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydro-alpha-cyperone 10V, Positive-QTOF	splash10-014i-0690000000-ab6abafc77bbed80cc59	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydro-alpha-cyperone 20V, Positive-QTOF	splash10-014i-2930000000-614876051a26654914f0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydro-alpha-cyperone 40V, Positive-QTOF	splash10-0udl-8900000000-3b3151768bb2a06efe3b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydro-alpha-cyperone 10V, Negative-QTOF	splash10-014i-0090000000-71005072ad6282db9d4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydro-alpha-cyperone 20V, Negative-QTOF	splash10-014i-0290000000-282e11f38d01fb072ee4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydro-alpha-cyperone 40V, Negative-QTOF	splash10-0002-0900000000-9a8b066ef8d0f992ad98	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydro-alpha-cyperone 10V, Negative-QTOF	splash10-014i-0090000000-93c59166c81b3b7c46b8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydro-alpha-cyperone 20V, Negative-QTOF	splash10-014i-0090000000-27395fa42ed8c0e0fb8f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydro-alpha-cyperone 40V, Negative-QTOF	splash10-02aj-0920000000-838f1780ad56fd3839d4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydro-alpha-cyperone 10V, Positive-QTOF	splash10-016r-0960000000-a61db63e8791e82da776	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydro-alpha-cyperone 20V, Positive-QTOF	splash10-00s9-3900000000-f5d659b6059517dae891	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydro-alpha-cyperone 40V, Positive-QTOF	splash10-014i-9600000000-f9a769948974a2608719	2021-09-25	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

FDB015501

KNApSAcK ID

C00012761

Chemspider ID

35014166

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13192441

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1855811

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 1,2-Dehydro-alpha-cyperone (HMDB0036589)

MOL for HMDB0036589 (1,2-Dehydro-alpha-cyperone)

3D MOL for HMDB0036589 (1,2-Dehydro-alpha-cyperone)

3D SDF for HMDB0036589 (1,2-Dehydro-alpha-cyperone)

3D-SDF for HMDB0036589 (1,2-Dehydro-alpha-cyperone)

PDB for HMDB0036589 (1,2-Dehydro-alpha-cyperone)

3D PDB for HMDB0036589 (1,2-Dehydro-alpha-cyperone)

SMILES for HMDB0036589 (1,2-Dehydro-alpha-cyperone)

INCHI for HMDB0036589 (1,2-Dehydro-alpha-cyperone)

Structure for HMDB0036589 (1,2-Dehydro-alpha-cyperone)

3D Structure for HMDB0036589 (1,2-Dehydro-alpha-cyperone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra