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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:50:50 UTC

Update Date

2022-03-07 02:55:01 UTC

HMDB ID

HMDB0036680

Secondary Accession Numbers

HMDB36680

Metabolite Identification

Common Name

Cyperolone

Description

Cyperolone belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. Cyperolone has been detected, but not quantified in, root vegetables. This could make cyperolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cyperolone.

Structure

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

HMDB0036680
     RDKit          3D
Cyperolone
 41 42  0  0  0  0  0  0  0  0999 V2000
    3.1730   -1.6068    1.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6156   -0.4195    1.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9856    0.6886    2.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5887   -0.1067    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3176   -1.3779   -0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1494   -1.2764   -1.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983   -0.0590   -1.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2931    0.9603   -2.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1073   -0.5100   -1.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160   -1.3258   -0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7778   -0.8033    0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6784   -0.4171    1.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8934    0.3429    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5540    1.6352    0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0552    2.9494   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6075    1.6545    0.9589 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396    0.3196    1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9578   -2.4509    0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9097   -1.7481    2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9881    0.4712    2.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1955    0.7183    3.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0559    1.6300    1.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0433    0.6931   -0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403   -1.7653   -0.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0359   -2.1471    0.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5696   -1.2691   -2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4499   -2.2182   -1.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0770    1.7558   -2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191    1.3571   -2.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3076    0.4175   -3.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7145    0.3990   -1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0316   -1.0671   -2.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6348   -1.2227   -0.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3600   -2.4277   -0.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1747   -1.6342    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8701   -1.1408    2.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879    2.9332   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0349    3.7051    0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7699    3.4011   -0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5644    1.3250    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2447   -0.3635    1.8807 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  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 17  1  0
 17  4  1  0
 13  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
M  END

  Mrv0541 05061309162D          

 17 18  0  0  0  0            999 V2000
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1457   -1.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4782    1.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7245   -1.1560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949   -0.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  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  6  1  0  0  0  0
 14  4  1  0  0  0  0
 14  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  2  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036680

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1CCC2(C)CCC(O)C2(C1)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-10(2)12-5-7-14(4)8-6-13(17)15(14,9-12)11(3)16/h12-13,17H,1,5-9H2,2-4H3

> <INCHI_KEY>
YALFFHSIVPCNLF-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.298693207548958

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[3-hydroxy-7a-methyl-5-(prop-1-en-2-yl)-octahydro-1H-inden-3a-yl]ethan-1-one

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
2.783855286333334

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.520698789163767

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.517438856977957

> <JCHEM_PKA_STRONGEST_BASIC>
-3.009829822163754

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
68.7117

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[3-hydroxy-7a-methyl-5-(prop-1-en-2-yl)-hexahydro-1H-inden-3a-yl]ethanone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036680
     RDKit          3D
Cyperolone
 41 42  0  0  0  0  0  0  0  0999 V2000
    3.1730   -1.6068    1.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6156   -0.4195    1.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9856    0.6886    2.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5887   -0.1067    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3176   -1.3779   -0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1494   -1.2764   -1.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983   -0.0590   -1.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2931    0.9603   -2.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1073   -0.5100   -1.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160   -1.3258   -0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7778   -0.8033    0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6784   -0.4171    1.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8934    0.3429    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5540    1.6352    0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0552    2.9494   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6075    1.6545    0.9589 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396    0.3196    1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9578   -2.4509    0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9097   -1.7481    2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9881    0.4712    2.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1955    0.7183    3.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0559    1.6300    1.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0433    0.6931   -0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403   -1.7653   -0.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0359   -2.1471    0.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5696   -1.2691   -2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4499   -2.2182   -1.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0770    1.7558   -2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191    1.3571   -2.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3076    0.4175   -3.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7145    0.3990   -1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0316   -1.0671   -2.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6348   -1.2227   -0.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3600   -2.4277   -0.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1747   -1.6342    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8701   -1.1408    2.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879    2.9332   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0349    3.7051    0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7699    3.4011   -0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5644    1.3250    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2447   -0.3635    1.8807 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  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 17  1  0
 17  4  1  0
 13  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 17 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      10.122   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.788  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.872  -2.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.626   3.072   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.626  -1.532   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.219  -2.158   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.417  -1.722   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   14                                                            
CONECT    5    7   12                                                       
CONECT    6    8   13                                                       
CONECT    7    5   14                                                       
CONECT    8    6   14                                                       
CONECT    9   12   15                                                       
CONECT   10    1    2   12                                                  
CONECT   11    3   15   16                                                  
CONECT   12    5    9   10                                                  
CONECT   13    6   15   17                                                  
CONECT   14    4    7    8   15                                             
CONECT   15    9   11   13   14                                             
CONECT   16   11                                                            
CONECT   17   13                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0036680
HETATM    1  C1  UNL     1       3.173  -1.607   1.433  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.616  -0.419   1.318  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.986   0.689   2.243  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.589  -0.107   0.272  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.318  -1.378  -0.496  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.149  -1.276  -1.413  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.698  -0.059  -1.274  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.293   0.960  -2.266  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.107  -0.510  -1.733  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.516  -1.326  -0.551  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.778  -0.803   0.632  1.00  0.00           C  
HETATM   12  O1  UNL     1      -2.678  -0.417   1.588  1.00  0.00           O  
HETATM   13  C12 UNL     1      -0.893   0.343   0.138  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.554   1.635   0.355  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.055   2.949  -0.096  1.00  0.00           C  
HETATM   16  O2  UNL     1      -2.608   1.655   0.959  1.00  0.00           O  
HETATM   17  C15 UNL     1       0.340   0.320   1.004  1.00  0.00           C  
HETATM   18  H1  UNL     1       2.958  -2.451   0.805  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.910  -1.748   2.224  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.988   0.471   2.661  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.196   0.718   3.029  1.00  0.00           H  
HETATM   22  H5  UNL     1       3.056   1.630   1.667  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.043   0.693  -0.337  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.240  -1.765  -0.973  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.036  -2.147   0.285  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.570  -1.269  -2.463  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.450  -2.218  -1.387  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.077   1.756  -2.437  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.719   1.357  -2.203  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.308   0.418  -3.266  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.714   0.399  -1.789  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.032  -1.067  -2.671  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.635  -1.223  -0.452  1.00  0.00           H  
HETATM   34  H17 UNL     1      -2.360  -2.428  -0.701  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.175  -1.634   1.054  1.00  0.00           H  
HETATM   36  H19 UNL     1      -2.870  -1.141   2.236  1.00  0.00           H  
HETATM   37  H20 UNL     1      -0.088   2.933  -0.600  1.00  0.00           H  
HETATM   38  H21 UNL     1      -1.035   3.705   0.719  1.00  0.00           H  
HETATM   39  H22 UNL     1      -1.770   3.401  -0.848  1.00  0.00           H  
HETATM   40  H23 UNL     1       0.564   1.325   1.454  1.00  0.00           H  
HETATM   41  H24 UNL     1       0.245  -0.363   1.881  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3    4
CONECT    3   20   21   22
CONECT    4    5   17   23
CONECT    5    6   24   25
CONECT    6    7   26   27
CONECT    7    8    9   13
CONECT    8   28   29   30
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   13   35
CONECT   12   36
CONECT   13   14   17
CONECT   14   15   16   16
CONECT   15   37   38   39
CONECT   17   40   41
END

HMDB0036680
     RDKit          3D
Cyperolone
 41 42  0  0  0  0  0  0  0  0999 V2000
    3.1730   -1.6068    1.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6156   -0.4195    1.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9856    0.6886    2.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5887   -0.1067    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3176   -1.3779   -0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1494   -1.2764   -1.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983   -0.0590   -1.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2931    0.9603   -2.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1073   -0.5100   -1.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160   -1.3258   -0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7778   -0.8033    0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6784   -0.4171    1.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8934    0.3429    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5540    1.6352    0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0552    2.9494   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6075    1.6545    0.9589 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396    0.3196    1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9578   -2.4509    0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9097   -1.7481    2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9881    0.4712    2.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1955    0.7183    3.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0559    1.6300    1.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0433    0.6931   -0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403   -1.7653   -0.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0359   -2.1471    0.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5696   -1.2691   -2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4499   -2.2182   -1.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0770    1.7558   -2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191    1.3571   -2.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3076    0.4175   -3.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7145    0.3990   -1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0316   -1.0671   -2.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6348   -1.2227   -0.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3600   -2.4277   -0.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1747   -1.6342    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8701   -1.1408    2.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879    2.9332   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0349    3.7051    0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7699    3.4011   -0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5644    1.3250    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2447   -0.3635    1.8807 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  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 17  1  0
 17  4  1  0
 13  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.3499

Monoisotopic Molecular Weight

236.177630012

IUPAC Name

1-[3-hydroxy-7a-methyl-5-(prop-1-en-2-yl)-octahydro-1H-inden-3a-yl]ethan-1-one

Traditional Name

1-[3-hydroxy-7a-methyl-5-(prop-1-en-2-yl)-hexahydro-1H-inden-3a-yl]ethanone

CAS Registry Number

13741-46-3

SMILES

CC(=C)C1CCC2(C)CCC(O)C2(C1)C(C)=O

InChI Identifier

InChI=1S/C15H24O2/c1-10(2)12-5-7-14(4)8-6-13(17)15(14,9-12)11(3)16/h12-13,17H,1,5-9H2,2-4H3

InChI Key

YALFFHSIVPCNLF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclic alcohols and derivatives

Alternative Parents

Substituents

Cyclic alcohol
Secondary alcohol
Ketone
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036680)

Source

Endogenous

Endogenous (HMDB: HMDB0036680)

Plant

Plant (HMDB: HMDB0036680)

Exogenous

Food

Food (HMDB: HMDB0036680)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Exogenous (HMDB: HMDB0036680)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036680)

Role

Biological role

Energy source (HMDB: HMDB0036680)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036680)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	41 - 42 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	345 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	0.19 g/L	ALOGPS
logP	2.76	ALOGPS
logP	2.78	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	14.52	ChemAxon
pKa (Strongest Basic)	-3	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	2	ChemAxon
Refractivity	68.71 m³·mol⁻¹	ChemAxon
Polarizability	27.3 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]+	155.933	31661259
DarkChem	[M-H]-	149.952	31661259
DeepCCS	[M+H]+	157.115	30932474
DeepCCS	[M-H]-	154.757	30932474
DeepCCS	[M-2H]-	188.71	30932474
DeepCCS	[M+Na]+	164.176	30932474
AllCCS	[M+H]+	156.8	32859911
AllCCS	[M+H-H2O]+	153.2	32859911
AllCCS	[M+NH4]+	160.2	32859911
AllCCS	[M+Na]+	161.1	32859911
AllCCS	[M-H]-	161.9	32859911
AllCCS	[M+Na-2H]-	162.4	32859911
AllCCS	[M+HCOO]-	163.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyperolone	CC(=C)C1CCC2(C)CCC(O)C2(C1)C(C)=O	2521.3	Standard polar	33892256
Cyperolone	CC(=C)C1CCC2(C)CCC(O)C2(C1)C(C)=O	1706.6	Standard non polar	33892256
Cyperolone	CC(=C)C1CCC2(C)CCC(O)C2(C1)C(C)=O	1830.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyperolone,1TMS,isomer #1	C=C(C)C1CCC2(C)CCC(O[Si](C)(C)C)C2(C(C)=O)C1	1833.6	Semi standard non polar	33892256
Cyperolone,1TMS,isomer #2	C=C(C)C1CCC2(C)CCC(O)C2(C(=C)O[Si](C)(C)C)C1	1804.8	Semi standard non polar	33892256
Cyperolone,2TMS,isomer #1	C=C(C)C1CCC2(C)CCC(O[Si](C)(C)C)C2(C(=C)O[Si](C)(C)C)C1	1854.9	Semi standard non polar	33892256
Cyperolone,2TMS,isomer #1	C=C(C)C1CCC2(C)CCC(O[Si](C)(C)C)C2(C(=C)O[Si](C)(C)C)C1	1854.7	Standard non polar	33892256
Cyperolone,1TBDMS,isomer #1	C=C(C)C1CCC2(C)CCC(O[Si](C)(C)C(C)(C)C)C2(C(C)=O)C1	2094.0	Semi standard non polar	33892256
Cyperolone,1TBDMS,isomer #2	C=C(C)C1CCC2(C)CCC(O)C2(C(=C)O[Si](C)(C)C(C)(C)C)C1	2056.3	Semi standard non polar	33892256
Cyperolone,2TBDMS,isomer #1	C=C(C)C1CCC2(C)CCC(O[Si](C)(C)C(C)(C)C)C2(C(=C)O[Si](C)(C)C(C)(C)C)C1	2357.0	Semi standard non polar	33892256
Cyperolone,2TBDMS,isomer #1	C=C(C)C1CCC2(C)CCC(O[Si](C)(C)C(C)(C)C)C2(C(=C)O[Si](C)(C)C(C)(C)C)C1	2310.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cyperolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9340000000-a9f1b28e38d7d470c12e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyperolone GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9180000000-15da31a2e12d9aae7831	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyperolone 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 - Cyperolone 10V, Positive-QTOF	splash10-014r-0190000000-203aeaed606039e66021	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperolone 20V, Positive-QTOF	splash10-0170-3790000000-3157241ab300ad7e9857	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperolone 40V, Positive-QTOF	splash10-0uxr-9210000000-901409c4d13083e5ed29	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperolone 10V, Negative-QTOF	splash10-000i-0090000000-a8e431257abb19d562b1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperolone 20V, Negative-QTOF	splash10-000i-0190000000-b7ff6ba48935009f55dd	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperolone 40V, Negative-QTOF	splash10-00ou-1950000000-603522b4b59d47cd845b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperolone 10V, Positive-QTOF	splash10-014r-0390000000-c9bba3055be2b6ed2e4f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperolone 20V, Positive-QTOF	splash10-004u-0930000000-68b82ac853e6eb5b7c43	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperolone 40V, Positive-QTOF	splash10-0006-9500000000-77856d957411b81d28fe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperolone 10V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperolone 20V, Negative-QTOF	splash10-000i-0290000000-470ab3bcfca794783ae3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperolone 40V, Negative-QTOF	splash10-002f-3940000000-29a1bcb0f6eb4456ca4d	2021-09-24	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12308852

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1856401

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Cyperolone (HMDB0036680)

MOL for HMDB0036680 (Cyperolone)

3D MOL for HMDB0036680 (Cyperolone)

3D SDF for HMDB0036680 (Cyperolone)

3D-SDF for HMDB0036680 (Cyperolone)

PDB for HMDB0036680 (Cyperolone)

3D PDB for HMDB0036680 (Cyperolone)

SMILES for HMDB0036680 (Cyperolone)

INCHI for HMDB0036680 (Cyperolone)

Structure for HMDB0036680 (Cyperolone)

3D Structure for HMDB0036680 (Cyperolone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra