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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-08 15:55:55 UTC

Update Date

2022-03-07 03:17:48 UTC

HMDB ID

HMDB0061853

Secondary Accession Numbers

HMDB61853

Metabolite Identification

Common Name

beta-Cubebene

Description

beta-Cubebene, also known as β-cubebene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on beta-Cubebene.

Structure

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

HMDB0061853
     RDKit          3D
beta-Cubebene
 39 41  0  0  0  0  0  0  0  0999 V2000
    2.1261    2.8671   -0.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9766    1.6982   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7028    1.2576    1.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7409    0.3143    1.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9318   -0.3139    0.5906 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0765    0.6295   -0.5939 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2336    0.3864    0.1320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2497   -0.3736   -0.6439 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6119    0.2825   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9792    0.2596    1.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6907    1.6509   -0.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3716   -1.8146   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1224   -2.5317    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0973   -1.7443    0.2626 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0765   -1.8420   -0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8152    3.5861   -0.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    3.1291   -1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9630    2.1192    1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6849    0.7762    0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0587    0.9158    2.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2899   -0.4549    2.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2026    0.2006   -1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5633    1.2873    0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0663   -0.2704   -1.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3563   -0.3639   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2024    1.2777    1.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8816   -0.3627    1.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1666   -0.1430    1.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1164    2.3295   -0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313    2.0546   -1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4288    1.7039   -1.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521   -2.3047   -1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743   -1.8644    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0919   -3.2255   -0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119   -3.2472    0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719   -2.2073    1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8437   -1.0504   -0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5732   -1.8039   -1.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6177   -2.8077   -0.8369 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
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  6  2  1  0
  7  5  1  0
 14  5  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
  6 22  1  6
  7 23  1  1
  8 24  1  6
  9 25  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  1
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END


  Mrv0541 02241220572D          

 15 17  0  0  1  0            999 V2000
    0.2017   -1.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -0.3210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4033   -0.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7810    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3346    1.1460    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5106    1.1063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1329    0.3728    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3135    1.0666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1113    0.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7502    1.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1579    0.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3890   -0.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7122    1.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2658    2.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5363    1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  2  1  0  0  0  0
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  6  0  0  0
  5 13  1  6  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061853

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)[C@@H]1CC[C@@H](C)[C@@]23CCC(=C)[C@@H]2[C@@H]13

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-9(2)12-6-5-11(4)15-8-7-10(3)13(15)14(12)15/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12+,13-,14-,15+/m1/s1

> <INCHI_KEY>
FSRZGYRCMPZNJF-KHMAMNHCSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
26.111464184212245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5S,6R,7S,10R)-10-methyl-4-methylidene-7-(propan-2-yl)tricyclo[4.4.0.0¹,⁵]decane

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
4.1460638329999995

> <ALOGPS_LOGS>
-4.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
64.6954

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.45e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-β-cubebene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061853
     RDKit          3D
beta-Cubebene
 39 41  0  0  0  0  0  0  0  0999 V2000
    2.1261    2.8671   -0.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9766    1.6982   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7028    1.2576    1.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7409    0.3143    1.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9318   -0.3139    0.5906 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0765    0.6295   -0.5939 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2336    0.3864    0.1320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2497   -0.3736   -0.6439 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6119    0.2825   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9792    0.2596    1.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6907    1.6509   -0.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3716   -1.8146   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1224   -2.5317    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0973   -1.7443    0.2626 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0765   -1.8420   -0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8152    3.5861   -0.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    3.1291   -1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9630    2.1192    1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6849    0.7762    0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0587    0.9158    2.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2899   -0.4549    2.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2026    0.2006   -1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5633    1.2873    0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0663   -0.2704   -1.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3563   -0.3639   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2024    1.2777    1.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8816   -0.3627    1.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1666   -0.1430    1.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1164    2.3295   -0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313    2.0546   -1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4288    1.7039   -1.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521   -2.3047   -1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743   -1.8644    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0919   -3.2255   -0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119   -3.2472    0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719   -2.2073    1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8437   -1.0504   -0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5732   -1.8039   -1.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6177   -2.8077   -0.8369 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
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  6  2  1  0
  7  5  1  0
 14  5  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
  6 22  1  6
  7 23  1  1
  8 24  1  6
  9 25  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  1
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.377  -1.968   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.081  -0.599   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.619  -0.525   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.325   0.844   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.491   2.139   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.953   2.065   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.248   0.696   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.585   1.991   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.074   1.599   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.267   2.573   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.161   0.061   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.726  -0.497   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.196   3.508   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.363   4.803   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.734   3.583   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2    8   12                                             
CONECT    8    7    6    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    7                                                       
CONECT   13    5   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

COMPND    HMDB0061853
HETATM    1  C1  UNL     1       2.126   2.867  -0.728  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.977   1.698  -0.149  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.703   1.258   1.068  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.741   0.314   1.710  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.932  -0.314   0.591  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.077   0.630  -0.594  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.234   0.386   0.132  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.250  -0.374  -0.644  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.612   0.283  -0.400  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.979   0.260   1.065  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.691   1.651  -0.993  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.372  -1.815  -0.275  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.122  -2.532   0.009  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.097  -1.744   0.263  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.076  -1.842  -0.917  1.00  0.00           C  
HETATM   16  H1  UNL     1       2.815   3.586  -0.322  1.00  0.00           H  
HETATM   17  H2  UNL     1       1.569   3.129  -1.611  1.00  0.00           H  
HETATM   18  H3  UNL     1       2.963   2.119   1.717  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.685   0.776   0.813  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.059   0.916   2.365  1.00  0.00           H  
HETATM   21  H6  UNL     1       2.290  -0.455   2.273  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.203   0.201  -1.602  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.563   1.287   0.721  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.066  -0.270  -1.734  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.356  -0.364  -0.925  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.202   1.278   1.457  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.882  -0.363   1.268  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.167  -0.143   1.706  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.116   2.329  -0.202  1.00  0.00           H  
HETATM   30  H15 UNL     1      -1.731   2.055  -1.342  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.429   1.704  -1.831  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.952  -2.305  -1.101  1.00  0.00           H  
HETATM   33  H18 UNL     1      -2.074  -1.864   0.609  1.00  0.00           H  
HETATM   34  H19 UNL     1       0.092  -3.225  -0.859  1.00  0.00           H  
HETATM   35  H20 UNL     1      -0.312  -3.247   0.864  1.00  0.00           H  
HETATM   36  H21 UNL     1       1.672  -2.207   1.121  1.00  0.00           H  
HETATM   37  H22 UNL     1       2.844  -1.050  -0.806  1.00  0.00           H  
HETATM   38  H23 UNL     1       1.573  -1.804  -1.879  1.00  0.00           H  
HETATM   39  H24 UNL     1       2.618  -2.808  -0.837  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3    6
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6    7   14
CONECT    6    7   22
CONECT    7    8   23
CONECT    8    9   12   24
CONECT    9   10   11   25
CONECT   10   26   27   28
CONECT   11   29   30   31
CONECT   12   13   32   33
CONECT   13   14   34   35
CONECT   14   15   36
CONECT   15   37   38   39
END

HMDB0061853
     RDKit          3D
beta-Cubebene
 39 41  0  0  0  0  0  0  0  0999 V2000
    2.1261    2.8671   -0.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9766    1.6982   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7028    1.2576    1.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7409    0.3143    1.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9318   -0.3139    0.5906 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0765    0.6295   -0.5939 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2336    0.3864    0.1320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2497   -0.3736   -0.6439 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6119    0.2825   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9792    0.2596    1.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6907    1.6509   -0.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3716   -1.8146   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1224   -2.5317    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0973   -1.7443    0.2626 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0765   -1.8420   -0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8152    3.5861   -0.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    3.1291   -1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9630    2.1192    1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6849    0.7762    0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0587    0.9158    2.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2899   -0.4549    2.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2026    0.2006   -1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5633    1.2873    0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0663   -0.2704   -1.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3563   -0.3639   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2024    1.2777    1.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8816   -0.3627    1.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1666   -0.1430    1.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1164    2.3295   -0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313    2.0546   -1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4288    1.7039   -1.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521   -2.3047   -1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743   -1.8644    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0919   -3.2255   -0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119   -3.2472    0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719   -2.2073    1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8437   -1.0504   -0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5732   -1.8039   -1.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6177   -2.8077   -0.8369 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
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  6  2  1  0
  7  5  1  0
 14  5  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
  6 22  1  6
  7 23  1  1
  8 24  1  6
  9 25  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  1
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-beta-Cubebene	ChEBI
(3AS-(3aalpha,3bbata,4beta,7alpha,7as*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzene	ChEBI
(-)-b-Cubebene	Generator
(-)-Β-cubebene	Generator
(3AS-(3aalpha,3bbata,4b,7a,7as*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzene	Generator
(3AS-(3aalpha,3bbata,4β,7α,7as*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzene	Generator
b-Cubebene	Generator
Β-cubebene	Generator
(3AS-(3aalpha,3bbata,4b,7a,7aa*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzene	HMDB
(3AS-(3aalpha,3bbata,4S,7R,7as*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1H-cyclopenta(1,3)cyclopropa(1,2)benzene	HMDB

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.3511

Monoisotopic Molecular Weight

204.187800768

IUPAC Name

(1R,5S,6R,7S,10R)-10-methyl-4-methylidene-7-(propan-2-yl)tricyclo[4.4.0.0¹,⁵]decane

Traditional Name

(-)-β-cubebene

CAS Registry Number

13744-15-5

SMILES

CC(C)[C@@H]1CC[C@@H](C)[C@@]23CCC(=C)[C@@H]2[C@@H]13

InChI Identifier

InChI=1S/C15H24/c1-9(2)12-6-5-11(4)15-8-7-10(3)13(15)14(12)15/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12+,13-,14-,15+/m1/s1

InChI Key

FSRZGYRCMPZNJF-KHMAMNHCSA-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

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

carbotricyclic compound (CHEBI:10363 )
sesquiterpene (CHEBI:10363 )
Cubebane and ivaxillarane sesquiterpenoids (C09648 )
Sesquiterpenoids (C15) (C09648 )

Ontology

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
Water Solubility	0.0024 g/L	ALOGPS
logP	3.49	ALOGPS
logP	4.15	ChemAxon
logS	-4.9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.7 m³·mol⁻¹	ChemAxon
Polarizability	26.11 Å³	ChemAxon
Number of Rings	3	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]+	151.24	31661259
DarkChem	[M-H]-	149.139	31661259
DeepCCS	[M-2H]-	195.834	30932474
DeepCCS	[M+Na]+	171.069	30932474
AllCCS	[M+H]+	148.0	32859911
AllCCS	[M+H-H2O]+	144.1	32859911
AllCCS	[M+NH4]+	151.6	32859911
AllCCS	[M+Na]+	152.6	32859911
AllCCS	[M-H]-	157.9	32859911
AllCCS	[M+Na-2H]-	158.3	32859911
AllCCS	[M+HCOO]-	158.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.39 minutes	32390414
Predicted by Siyang on May 30, 2022	20.8271 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.22 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2662.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	760.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	271.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	426.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	460.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	858.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	915.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	168.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1652.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	559.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1698.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	573.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	526.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	499.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	669.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Cubebene	CC(C)[C@@H]1CC[C@@H](C)[C@@]23CCC(=C)[C@@H]2[C@@H]13	1621.4	Standard polar	33892256
beta-Cubebene	CC(C)[C@@H]1CC[C@@H](C)[C@@]23CCC(=C)[C@@H]2[C@@H]13	1409.8	Standard non polar	33892256
beta-Cubebene	CC(C)[C@@H]1CC[C@@H](C)[C@@]23CCC(=C)[C@@H]2[C@@H]13	1412.9	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Piper cubeba

METLIN ID

Not Available

PubChem Compound

93081

PDB ID

Not Available

ChEBI ID

10363

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1454791

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Debrauwere J, Verzele M: Constituents of peppers: IV. The hydrocarbons of pepper essential oil. J Chromatogr Sci. 1976 Jun;14(6):296-8. [PubMed:1270568 ]
Kasali AA, Ekundayo O, Paul C, Konig WA: epi-Cubebanes from Solidago canadensis. Phytochemistry. 2002 Apr;59(8):805-10. [PubMed:11937158 ]
Sajjadi SE, Ghannadi A, Sajjadi SE, Ghannadi A: Volatile oil composition of the aerial parts of Ajuga orientalis L. from Iran. Z Naturforsch C. 2004 Mar-Apr;59(3-4):166-8. [PubMed:15241917 ]
Nickavar B, Amin G, Yosefi M: Volatile constituents of the flower and fruit oils of Pittosporum tobira (Thunb.) Ait. grown in Iran. Z Naturforsch C. 2004 Mar-Apr;59(3-4):174-6. [PubMed:15241919 ]
Skalicka-Wozniak K, Ludwiczuk A, Widelski J, Filipe JJ, Asakawa Y, Glowniak K: Volatile constituents of Ocimum minimum herb cultivated in Portugal. Nat Prod Commun. 2009 Oct;4(10):1383-6. [PubMed:19911576 ]
Park SY, Park SJ, Park NJ, Joo WH, Lee SJ, Choi YW: alpha-Iso-cubebene exerts neuroprotective effects in amyloid beta stimulated microglia activation. Neurosci Lett. 2013 Oct 25;555:143-8. doi: 10.1016/j.neulet.2013.09.053. Epub 2013 Sep 30. [PubMed:24090820 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
Wikipedia [Link]
MetaCyc: beta-cubebene biosynthesis [Link]
UniProt B3TPQ6 : Beta-cubebene synthase [Link]

Showing metabocard for beta-Cubebene (HMDB0061853)

MOL for HMDB0061853 (beta-Cubebene)

3D MOL for HMDB0061853 (beta-Cubebene)

3D SDF for HMDB0061853 (beta-Cubebene)

3D-SDF for HMDB0061853 (beta-Cubebene)

PDB for HMDB0061853 (beta-Cubebene)

3D PDB for HMDB0061853 (beta-Cubebene)

SMILES for HMDB0061853 (beta-Cubebene)

INCHI for HMDB0061853 (beta-Cubebene)

Structure for HMDB0061853 (beta-Cubebene)

3D Structure for HMDB0061853 (beta-Cubebene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized