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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:58:32 UTC

Update Date

2022-03-07 02:55:04 UTC

HMDB ID

HMDB0036799

Secondary Accession Numbers

HMDB36799

Metabolite Identification

Common Name

Cycloseychellene

Description

Rotenone, also known as derris or 5'beta-rotenone, belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. Thus, rotenone is considered to be a flavonoid lipid molecule. Rotenone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Rotenone has been detected, but not quantified in, jicama and pulses. This could make rotenone a potential biomarker for the consumption of these foods. Rotenone is an isoflavone compound that naturally occurs in the jicama vine plant as well as many Fabaceae plants.

Structure

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

HMDB0036799
     RDKit          3D
Cycloseychellene
 39 42  0  0  0  0  0  0  0  0999 V2000
    3.3818   -0.1992   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9962   -0.5278    0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4351   -1.6692   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0189   -1.7143   -0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7432   -0.4222   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7479   -0.3300   -1.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219    0.7926   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6252    1.1206   -1.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8579    1.8885   -0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7340    1.2008    0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9200    0.4538    1.8875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4903    0.8699    1.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1711    0.7029    0.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5033   -0.2569    0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7079   -1.1355    1.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3489    0.7702   -0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1396   -0.1052    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6855   -0.9687   -0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1859   -0.8314    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7473   -2.6194    0.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9563   -1.7462   -1.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2424   -2.2163   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5056   -2.4035    0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831   -1.2393   -1.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2434   -0.2460   -2.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4298    0.5273   -1.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5114    1.7517   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1858    1.6829   -2.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7676    0.1885   -2.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2701    2.7156    0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4472    2.2633   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7095    1.6155    1.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3124    0.2289    2.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0987    0.2930    2.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535    1.9354    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8366    1.6047    0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6218   -2.0898    0.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916   -0.5783    0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8770   -1.3069    2.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  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
 11 14  1  0
 14 15  1  0
 13  2  1  0
 14  5  1  0
 13  7  1  0
 14 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 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
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END


  Mrv0541 05061309202D          

 15 18  0  0  0  0            999 V2000
   -0.8246   -0.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1362    1.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8665    2.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0246    2.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6417    1.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1097    1.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5127    0.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676    0.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3086    0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5711    0.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1418    0.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4186    0.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6530    1.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7348    1.7857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6050    1.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  2  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14  3  1  0  0  0  0
 14  6  1  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036799

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2(C)C3(C)C4CC2(C)C1CC34

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-9-5-6-14(3)13(2)8-12-11(7-10(9)13)15(12,14)4/h9-12H,5-8H2,1-4H3

> <INCHI_KEY>
XPWRIXBORAHMCD-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
25.36127226895207

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,7,8,11-tetramethyltetracyclo[5.4.0.0³,⁵.0⁴,⁸]undecane

> <ALOGPS_LOGP>
4.47

> <JCHEM_LOGP>
3.740940651333333

> <ALOGPS_LOGS>
-5.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
62.8639

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.16e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,7,8,11-tetramethyltetracyclo[5.4.0.0³,⁵.0⁴,⁸]undecane

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036799
     RDKit          3D
Cycloseychellene
 39 42  0  0  0  0  0  0  0  0999 V2000
    3.3818   -0.1992   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9962   -0.5278    0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4351   -1.6692   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0189   -1.7143   -0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7432   -0.4222   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7479   -0.3300   -1.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219    0.7926   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6252    1.1206   -1.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8579    1.8885   -0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7340    1.2008    0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9200    0.4538    1.8875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4903    0.8699    1.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1711    0.7029    0.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5033   -0.2569    0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7079   -1.1355    1.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3489    0.7702   -0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1396   -0.1052    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6855   -0.9687   -0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1859   -0.8314    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7473   -2.6194    0.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9563   -1.7462   -1.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2424   -2.2163   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5056   -2.4035    0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831   -1.2393   -1.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2434   -0.2460   -2.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4298    0.5273   -1.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5114    1.7517   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1858    1.6829   -2.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7676    0.1885   -2.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2701    2.7156    0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4472    2.2633   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7095    1.6155    1.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3124    0.2289    2.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0987    0.2930    2.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535    1.9354    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8366    1.6047    0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6218   -2.0898    0.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916   -0.5783    0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8770   -1.3069    2.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  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
 11 14  1  0
 14 15  1  0
 13  2  1  0
 14  5  1  0
 13  7  1  0
 14 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 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
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  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      -1.539  -0.130   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.254   2.173   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.617   4.803   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.779   4.324   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.198   2.425   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.205   3.591   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.824   0.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.806   0.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.576   1.007   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.066   0.180   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.998   1.692   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.648   1.714   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.219   1.946   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.372   3.333   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.996   3.055   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    6    9                                                       
CONECT    6    5   14                                                       
CONECT    7   10   11                                                       
CONECT    8   12   13                                                       
CONECT    9    1    5   10                                                  
CONECT   10    7    9   13                                                  
CONECT   11    7   12   15                                                  
CONECT   12    8   11   15                                                  
CONECT   13    2    8   10   14                                             
CONECT   14    3    6   13   15                                             
CONECT   15    4   11   12   14                                             
MASTER        0    0    0    0    0    0    0    0   15    0   36    0
END

COMPND    HMDB0036799
HETATM    1  C1  UNL     1       3.382  -0.199  -0.080  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.996  -0.528   0.480  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.435  -1.669  -0.277  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.019  -1.714  -0.470  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.743  -0.422  -0.465  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.748  -0.330  -1.623  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.122   0.793  -0.548  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.625   1.121  -1.903  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.858   1.888  -0.109  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.734   1.201   0.909  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.920   0.454   1.887  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.490   0.870   1.844  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.171   0.703   0.515  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.503  -0.257   0.792  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.708  -1.136   1.026  1.00  0.00           C  
HETATM   16  H1  UNL     1       3.349   0.770  -0.647  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.140  -0.105   0.693  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.686  -0.969  -0.832  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.186  -0.831   1.553  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.747  -2.619   0.251  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.956  -1.746  -1.277  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.242  -2.216  -1.458  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.506  -2.404   0.283  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.383  -1.239  -1.542  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.243  -0.246  -2.594  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.430   0.527  -1.412  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.511   1.752  -1.885  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.186   1.683  -2.453  1.00  0.00           H  
HETATM   29  H14 UNL     1       0.768   0.189  -2.514  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.270   2.716   0.343  1.00  0.00           H  
HETATM   31  H16 UNL     1      -1.447   2.263  -0.975  1.00  0.00           H  
HETATM   32  H17 UNL     1      -2.710   1.615   1.169  1.00  0.00           H  
HETATM   33  H18 UNL     1      -1.312   0.229   2.918  1.00  0.00           H  
HETATM   34  H19 UNL     1       1.099   0.293   2.593  1.00  0.00           H  
HETATM   35  H20 UNL     1       0.553   1.935   2.212  1.00  0.00           H  
HETATM   36  H21 UNL     1       1.837   1.605   0.387  1.00  0.00           H  
HETATM   37  H22 UNL     1      -2.622  -2.090   0.462  1.00  0.00           H  
HETATM   38  H23 UNL     1      -3.592  -0.578   0.644  1.00  0.00           H  
HETATM   39  H24 UNL     1      -2.877  -1.307   2.101  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   13   19
CONECT    3    4   20   21
CONECT    4    5   22   23
CONECT    5    6    7   14
CONECT    6   24   25   26
CONECT    7    8    9   13
CONECT    8   27   28   29
CONECT    9   10   30   31
CONECT   10   11   14   32
CONECT   11   12   14   33
CONECT   12   13   34   35
CONECT   13   36
CONECT   14   15
CONECT   15   37   38   39
END

HMDB0036799
     RDKit          3D
Cycloseychellene
 39 42  0  0  0  0  0  0  0  0999 V2000
    3.3818   -0.1992   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9962   -0.5278    0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4351   -1.6692   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0189   -1.7143   -0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7432   -0.4222   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7479   -0.3300   -1.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219    0.7926   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6252    1.1206   -1.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8579    1.8885   -0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7340    1.2008    0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9200    0.4538    1.8875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4903    0.8699    1.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1711    0.7029    0.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5033   -0.2569    0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7079   -1.1355    1.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3489    0.7702   -0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1396   -0.1052    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6855   -0.9687   -0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1859   -0.8314    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7473   -2.6194    0.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9563   -1.7462   -1.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2424   -2.2163   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5056   -2.4035    0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831   -1.2393   -1.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2434   -0.2460   -2.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4298    0.5273   -1.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5114    1.7517   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1858    1.6829   -2.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7676    0.1885   -2.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2701    2.7156    0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4472    2.2633   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7095    1.6155    1.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3124    0.2289    2.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0987    0.2930    2.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535    1.9354    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8366    1.6047    0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6218   -2.0898    0.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916   -0.5783    0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8770   -1.3069    2.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  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
 11 14  1  0
 14 15  1  0
 13  2  1  0
 14  5  1  0
 13  7  1  0
 14 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 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
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-cis-Rotenone	ChEBI
(-)-Rotenone	ChEBI
5'beta-Rotenone	ChEBI
[2R-(2alpha,6Aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one	ChEBI
Barbasco	ChEBI
Canex	ChEBI
Dactinol	ChEBI
Derris	ChEBI
Noxfire	ChEBI
Paraderil	ChEBI
Tubatoxin	ChEBI
5'b-Rotenone	Generator
5'Β-rotenone	Generator
[2R-(2a,6Aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one	Generator
[2R-(2Α,6aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one	Generator
1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one, 9ci	HMDB
Derrin	HMDB
Derris, jmaf	HMDB
Dri-kil	HMDB
Nicouline	HMDB
Noxfish	HMDB
Tubotoxin	HMDB

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.3511

Monoisotopic Molecular Weight

204.187800768

IUPAC Name

4,7,8,11-tetramethyltetracyclo[5.4.0.0³,⁵.0⁴,⁸]undecane

Traditional Name

4,7,8,11-tetramethyltetracyclo[5.4.0.0³,⁵.0⁴,⁸]undecane

CAS Registry Number

52617-34-2

SMILES

CC1CCC2(C)C3(C)C4CC2(C)C1CC34

InChI Identifier

InChI=1S/C15H24/c1-9-5-6-14(3)13(2)8-12-11(7-10(9)13)15(12,14)4/h9-12H,5-8H2,1-4H3

InChI Key

XPWRIXBORAHMCD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Rotenoids

Direct Parent

Rotenones

Alternative Parents

Substituents

Rotenone or derivatives
8-prenylated isoflavanone
Isoflavanone
Isoflavan
Chromone
Chromane
1-benzopyran
Benzopyran
Coumaran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Benzenoid
Ketone
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound (CHEBI:28201 )
rotenones (CHEBI:28201 )
rotenones (C07593 )
Rotenoid flavonoids (C07593 )
Pesticides (C07593 )
Rotenoid flavonoids (LMPK12060007 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036799)
Cell membrane (HMDB: HMDB0036799)

Cellular substructure

Extracellular (HMDB: HMDB0036799)
Membrane (HMDB: HMDB0036799)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036799)

Source

Endogenous

Endogenous (HMDB: HMDB0036799)

Plant

Plant (HMDB: HMDB0036799)

Animal

Animal (HMDB: HMDB0036799)

Exogenous

Food

Food (HMDB: HMDB0036799)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036799)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036799)

Cellular process

Cell signaling (HMDB: HMDB0036799)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036799)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036799)

Nutrient

Nutrient (HMDB: HMDB0036799)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036799)

Emulsifier (HMDB: HMDB0036799)

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	0.00042 g/L	ALOGPS
logP	4.47	ALOGPS
logP	3.74	ChemAxon
logS	-5.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	62.86 m³·mol⁻¹	ChemAxon
Polarizability	25.36 Å³	ChemAxon
Number of Rings	4	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]+	150.248	31661259
DarkChem	[M-H]-	144.684	31661259
DeepCCS	[M-2H]-	187.699	30932474
DeepCCS	[M+Na]+	162.754	30932474
AllCCS	[M+H]+	147.5	32859911
AllCCS	[M+H-H2O]+	143.7	32859911
AllCCS	[M+NH4]+	151.1	32859911
AllCCS	[M+Na]+	152.1	32859911
AllCCS	[M-H]-	160.0	32859911
AllCCS	[M+Na-2H]-	160.1	32859911
AllCCS	[M+HCOO]-	160.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cycloseychellene	CC1CCC2(C)C3(C)C4CC2(C)C1CC34	1591.1	Standard polar	33892256
Cycloseychellene	CC1CCC2(C)C3(C)C4CC2(C)C1CC34	1439.7	Standard non polar	33892256
Cycloseychellene	CC1CCC2(C)C3(C)C4CC2(C)C1CC34	1411.0	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 - Cycloseychellene GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-3900000000-2b9c1013929c318bce4a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cycloseychellene 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 - Cycloseychellene 10V, Positive-QTOF	splash10-0a4i-0090000000-98b8e4eab8cd946d233c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloseychellene 20V, Positive-QTOF	splash10-0a4i-1490000000-7a725e3ea16e1b28ba40	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloseychellene 40V, Positive-QTOF	splash10-06te-3900000000-d72662a16adb4f83c184	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloseychellene 10V, Negative-QTOF	splash10-0udi-0090000000-d0fe5ed0bbcfa60c303c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloseychellene 20V, Negative-QTOF	splash10-0udi-0090000000-829ffa2a496cae88f4ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloseychellene 40V, Negative-QTOF	splash10-0fe0-1920000000-f32b62ce5cffd0ea4d7d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloseychellene 10V, Positive-QTOF	splash10-0a4i-0090000000-c084f3d998cc56a199d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloseychellene 20V, Positive-QTOF	splash10-0a4j-0590000000-e270a4e16b089b4c94c0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloseychellene 40V, Positive-QTOF	splash10-052b-0960000000-75a6df425fb300f2e2b2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloseychellene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloseychellene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloseychellene 40V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	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

DB11457

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Rotenone

METLIN ID

Not Available

PubChem Compound

6758

PDB ID

Not Available

ChEBI ID

28201

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 Cycloseychellene (HMDB0036799)

MOL for HMDB0036799 (Cycloseychellene)

3D MOL for HMDB0036799 (Cycloseychellene)

3D SDF for HMDB0036799 (Cycloseychellene)

3D-SDF for HMDB0036799 (Cycloseychellene)

PDB for HMDB0036799 (Cycloseychellene)

3D PDB for HMDB0036799 (Cycloseychellene)

SMILES for HMDB0036799 (Cycloseychellene)

INCHI for HMDB0036799 (Cycloseychellene)

Structure for HMDB0036799 (Cycloseychellene)

3D Structure for HMDB0036799 (Cycloseychellene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra