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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:48:44 UTC

Update Date

2021-09-26 22:50:41 UTC

HMDB ID

HMDB0243562

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-

Description

4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on 4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene. This compound has been identified in human blood as reported by (PMID: 31557052 ). Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1r,4e,9s)- is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0243562
     RDKit          3D
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.3470   -3.3745    0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3202   -2.0543    0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3971   -1.1232    0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986   -1.1645    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1590    0.2992   -0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3429    1.3425   -0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2593    2.5842   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921    1.7270    0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2530    1.1106    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8989    0.0282   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9816   -1.3171    0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555   -1.5903   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4309   -0.0677   -0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0442    0.3690    1.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292    0.4360   -1.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5868   -3.9219    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2790   -3.8987    0.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1277   -0.5519   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3034   -0.5275    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3124   -1.5340    1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1531   -1.7619   -0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2682    0.4181   -0.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323    2.7717    0.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7013    3.4773   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9163    2.3935   -1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7597    2.2180   -0.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0083    2.7021    0.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0392    1.9509    0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4179    1.0182    1.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6570   -0.0069   -1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1150   -1.1097    1.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0175   -2.1028    0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0102   -1.9448   -1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9528   -0.2135    1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3478    0.4689    1.8877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4393    1.4138    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6434   -0.0667   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9949    1.5065   -1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1626    0.0962   -1.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 11  2  1  0
 13 10  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END


  Mrv1533004171515232D          

 15 16  0  0  0  0            999 V2000
    5.6877    2.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0557    1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3378    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0557    0.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -0.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287   -0.1033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1162   -0.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984    0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734    0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734    1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3484    1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734    2.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984    1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287    1.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    2.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0243562

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CCCC(=C)C2CC(C)(C)C2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3

> <INCHI_KEY>
NPNUFJAVOOONJE-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.9302342227409

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

> <ALOGPS_LOGP>
5.35

> <JCHEM_LOGP>
4.519309391666669

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
67.4524

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0243562
     RDKit          3D
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.3470   -3.3745    0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3202   -2.0543    0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3971   -1.1232    0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986   -1.1645    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1590    0.2992   -0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3429    1.3425   -0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2593    2.5842   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921    1.7270    0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2530    1.1106    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8989    0.0282   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9816   -1.3171    0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555   -1.5903   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4309   -0.0677   -0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0442    0.3690    1.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292    0.4360   -1.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5868   -3.9219    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2790   -3.8987    0.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1277   -0.5519   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3034   -0.5275    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3124   -1.5340    1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1531   -1.7619   -0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2682    0.4181   -0.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323    2.7717    0.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7013    3.4773   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9163    2.3935   -1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7597    2.2180   -0.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0083    2.7021    0.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0392    1.9509    0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4179    1.0182    1.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6570   -0.0069   -1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1150   -1.1097    1.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0175   -2.1028    0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0102   -1.9448   -1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9528   -0.2135    1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3478    0.4689    1.8877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4393    1.4138    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6434   -0.0667   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9949    1.5065   -1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1626    0.0962   -1.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 11  2  1  0
 13 10  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      10.617   4.194   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.437   3.204   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.964   1.757   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.437   0.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.104  -0.460   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.587  -0.193   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.817  -1.526   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.597   0.987   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.057   0.987   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.057   2.527   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.517   2.527   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.057   4.067   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.597   2.527   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.587   3.707   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.104   3.974   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14    2                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0243639
HETATM    1  C1  UNL     1      -0.306  -3.225   0.199  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.022  -2.078  -0.359  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.445  -1.846  -0.737  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.273  -1.222   0.334  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.968  -0.005  -0.173  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.502   1.229  -0.056  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.281   2.400  -0.604  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.204   1.536   0.608  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.019   1.263  -0.307  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.780   0.169   0.298  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.974  -1.030  -0.618  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.298  -1.217   0.092  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.289   0.313   0.267  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.857   1.002  -0.926  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.875   0.709   1.580  1.00  0.00           C  
HETATM   16  H1  UNL     1       0.457  -3.967   0.369  1.00  0.00           H  
HETATM   17  H2  UNL     1      -1.332  -3.414   0.479  1.00  0.00           H  
HETATM   18  H3  UNL     1       1.470  -1.225  -1.676  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.854  -2.834  -1.046  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.081  -1.957   0.625  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.732  -1.037   1.286  1.00  0.00           H  
HETATM   22  H7  UNL     1       3.926  -0.133  -0.674  1.00  0.00           H  
HETATM   23  H8  UNL     1       4.372   2.240  -0.498  1.00  0.00           H  
HETATM   24  H9  UNL     1       3.063   2.584  -1.657  1.00  0.00           H  
HETATM   25  H10 UNL     1       3.028   3.300  -0.027  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.147   2.578   0.956  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.164   0.905   1.534  1.00  0.00           H  
HETATM   28  H13 UNL     1       0.360   1.049  -1.359  1.00  0.00           H  
HETATM   29  H14 UNL     1      -0.619   2.171  -0.385  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.494  -0.161   1.326  1.00  0.00           H  
HETATM   31  H16 UNL     1      -1.136  -0.757  -1.673  1.00  0.00           H  
HETATM   32  H17 UNL     1      -2.113  -1.649   1.096  1.00  0.00           H  
HETATM   33  H18 UNL     1      -3.122  -1.609  -0.492  1.00  0.00           H  
HETATM   34  H19 UNL     1      -3.099   2.060  -0.626  1.00  0.00           H  
HETATM   35  H20 UNL     1      -3.863   0.533  -1.130  1.00  0.00           H  
HETATM   36  H21 UNL     1      -2.225   0.962  -1.813  1.00  0.00           H  
HETATM   37  H22 UNL     1      -2.513  -0.008   2.355  1.00  0.00           H  
HETATM   38  H23 UNL     1      -2.497   1.704   1.896  1.00  0.00           H  
HETATM   39  H24 UNL     1      -3.977   0.668   1.537  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3   11
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6    6   22
CONECT    6    7    8
CONECT    7   23   24   25
CONECT    8    9   26   27
CONECT    9   10   28   29
CONECT   10   11   13   30
CONECT   11   12   31
CONECT   12   13   32   33
CONECT   13   14   15
CONECT   14   34   35   36
CONECT   15   37   38   39
END

HMDB0243562
     RDKit          3D
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.3470   -3.3745    0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3202   -2.0543    0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3971   -1.1232    0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986   -1.1645    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1590    0.2992   -0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3429    1.3425   -0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2593    2.5842   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921    1.7270    0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2530    1.1106    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8989    0.0282   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9816   -1.3171    0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555   -1.5903   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4309   -0.0677   -0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0442    0.3690    1.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292    0.4360   -1.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5868   -3.9219    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2790   -3.8987    0.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1277   -0.5519   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3034   -0.5275    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3124   -1.5340    1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1531   -1.7619   -0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2682    0.4181   -0.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323    2.7717    0.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7013    3.4773   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9163    2.3935   -1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7597    2.2180   -0.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0083    2.7021    0.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0392    1.9509    0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4179    1.0182    1.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6570   -0.0069   -1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1150   -1.1097    1.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0175   -2.1028    0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0102   -1.9448   -1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9528   -0.2135    1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3478    0.4689    1.8877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4393    1.4138    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6434   -0.0667   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9949    1.5065   -1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1626    0.0962   -1.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 11  2  1  0
 13 10  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 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
Caryophyllene, (R-(r,4Z,9S))-isomer	MeSH, HMDB
Caryophyllene, (S-(r,4Z,9S))-isomer	MeSH, HMDB
Caryophyllene, (S-(r,4E,9S))-isomer	MeSH, HMDB
beta-Caryophyllene	MeSH, HMDB
Isocaryophyllene	MeSH, HMDB
Caryophyllene, (r,4Z,9S)-(+-)-isomer	MeSH, HMDB
(e)-beta-Caryophyllene	MeSH, HMDB
Caryophyllene, (R-(r*,4E,9S))-isomer	MeSH, HMDB
trans-Caryophyllene	MeSH, HMDB
Caryophyllene	MeSH, HMDB

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.357

Monoisotopic Molecular Weight

204.187800773

IUPAC Name

4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

Traditional Name

4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

CAS Registry Number

Not Available

SMILES

CC1=CCCC(=C)C2CC(C)(C)C2CC1

InChI Identifier

InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3

InChI Key

NPNUFJAVOOONJE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Caryophyllane sesquiterpenoid
Sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

a sesquiterpenoid (CPD-8230 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

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
logP	5.35	ALOGPS
logP	4.52	ChemAxon
logS	-4.8	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	67.45 m³·mol⁻¹	ChemAxon
Polarizability	25.93 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
DeepCCS	[M+H]+	150.977	30932474
DeepCCS	[M-H]-	148.619	30932474
DeepCCS	[M-2H]-	183.052	30932474
DeepCCS	[M+Na]+	158.053	30932474
AllCCS	[M+H]+	147.3	32859911
AllCCS	[M+H-H2O]+	143.2	32859911
AllCCS	[M+NH4]+	151.0	32859911
AllCCS	[M+Na]+	152.1	32859911
AllCCS	[M-H]-	156.0	32859911
AllCCS	[M+Na-2H]-	156.4	32859911
AllCCS	[M+HCOO]-	157.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-	CC1=CCCC(=C)C2CC(C)(C)C2CC1	1444.4	Standard non polar	33892256
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-	CC1=CCCC(=C)C2CC(C)(C)C2CC1	1430.8	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 - Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2900000000-9339cba1034fc0050a98	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- 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 - Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- 10V, Positive-QTOF	splash10-0a4i-0190000000-e8e2a53e6c8a577cd2c4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- 20V, Positive-QTOF	splash10-052b-0940000000-4f0db568926789b82528	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- 40V, Positive-QTOF	splash10-052g-9700000000-24f3ae9730f7cfa936df	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- 40V, Negative-QTOF	splash10-0udi-0090000000-0b1ac00c3b3c6c0a73b9	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24520

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

26318

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- (HMDB0243562)

MOL for HMDB0243562 (Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-)

3D MOL for HMDB0243562 (Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-)

3D SDF for HMDB0243562 (Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-)

3D-SDF for HMDB0243562 (Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-)

PDB for HMDB0243562 (Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-)

3D PDB for HMDB0243562 (Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-)

SMILES for HMDB0243562 (Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-)

INCHI for HMDB0243562 (Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-)

Structure for HMDB0243562 (Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-)

3D Structure for HMDB0243562 (Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra