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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-08 15:55:51 UTC

Update Date

2022-03-07 03:17:48 UTC

HMDB ID

HMDB0061850

Secondary Accession Numbers

HMDB61850

Metabolite Identification

Common Name

alpha-Bourbonene

Description

alpha-Bourbonene, also known as α-bourbonene or a-cis-bergamotene, 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 alpha-Bourbonene.

Structure

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

HMDB0061850
     RDKit          3D
alpha-Bourbonene
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.7560   -2.8924   -0.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9575   -1.4341   -0.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460   -0.9244   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9786    0.5415    0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8254    0.9459   -0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0503   -0.3435   -0.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1156    0.1363    0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3033    0.1957   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2439   -0.5317    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6578   -0.4529    0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8334   -1.9989    0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6758    1.6549   -0.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483    2.2529   -0.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527    1.5308   -0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0691    2.2643    1.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1527   -3.3457    0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7287   -3.4258   -0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2953   -3.0662   -1.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9039   -1.4995    0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550    0.8554    1.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9346    0.9373   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747    1.4560   -1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5476   -0.4232   -1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3388   -0.3555    1.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3979   -0.2471   -1.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1024   -0.1731    1.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6358   -0.4834   -0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1959    0.4282    0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2083   -1.3840    0.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9675   -2.1179    1.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6608   -2.6521    0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5111   -2.2388   -0.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.1096    0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4092    1.8264   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3932    3.3406   -0.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407    2.0187   -1.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1995    1.6270    2.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0034    2.8320    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2883    3.0368    1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  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
 14  7  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

  Mrv0541 02241212582D          

 15 17  0  0  0  0            999 V2000
   -2.5929   -0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073   -1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784   -1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3390   -0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0534   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0534   -1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3755   -1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3755   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907   -2.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0534   -0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9589   -2.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453   -3.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7557   -2.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  7  5  1  0  0  0  0
  5  4  1  0  0  0  0
  4  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7  8  1  0  0  0  0
  3 11  1  0  0  0  0
  7 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061850

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1CCC2(C)C3CC=C(C)C3C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)13(12)14(11)15/h5,9,11-14H,6-8H2,1-4H3

> <INCHI_KEY>
FAIMMSRDTUMTQR-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
25.967140029812626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dimethyl-10-(propan-2-yl)tricyclo[5.3.0.0²,⁶]dec-3-ene

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
4.0881301626666655

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
65.7679

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-isopropyl-3,7-dimethyltricyclo[5.3.0.0²,⁶]dec-3-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061850
     RDKit          3D
alpha-Bourbonene
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.7560   -2.8924   -0.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9575   -1.4341   -0.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460   -0.9244   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9786    0.5415    0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8254    0.9459   -0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0503   -0.3435   -0.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1156    0.1363    0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3033    0.1957   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2439   -0.5317    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6578   -0.4529    0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8334   -1.9989    0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6758    1.6549   -0.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483    2.2529   -0.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527    1.5308   -0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0691    2.2643    1.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1527   -3.3457    0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7287   -3.4258   -0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2953   -3.0662   -1.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9039   -1.4995    0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550    0.8554    1.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9346    0.9373   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747    1.4560   -1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5476   -0.4232   -1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3388   -0.3555    1.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3979   -0.2471   -1.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1024   -0.1731    1.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6358   -0.4834   -0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1959    0.4282    0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2083   -1.3840    0.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9675   -2.1179    1.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6608   -2.6521    0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5111   -2.2388   -0.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.1096    0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4092    1.8264   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3932    3.3406   -0.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407    2.0187   -1.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1995    1.6270    2.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0034    2.8320    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2883    3.0368    1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  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
 14  7  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 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      -4.840  -1.078   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.174  -1.848   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.174  -3.388   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.506  -3.388   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.506  -1.848   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.633  -1.078   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.966  -1.848   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.966  -3.388   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.701  -3.388   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.701  -1.848   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.263  -4.477   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.966  -0.308   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.790  -4.477   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.391  -5.965   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.277  -4.078   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    8                                                  
CONECT    5    1    7    4                                                  
CONECT    6    7   10                                                       
CONECT    7    5    6    8   12                                             
CONECT    8    4    9    7                                                  
CONECT    9    8   10   13                                                  
CONECT   10    6    9                                                       
CONECT   11    3                                                            
CONECT   12    7                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

COMPND    HMDB0061850
HETATM    1  C1  UNL     1      -1.756  -2.892  -0.765  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.957  -1.434  -0.572  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.046  -0.924  -0.009  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.979   0.542   0.053  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.825   0.946  -0.800  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.050  -0.344  -0.944  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.116   0.136   0.160  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.303   0.196  -0.294  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.244  -0.532   0.647  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.658  -0.453   0.163  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.833  -1.999   0.646  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.676   1.655  -0.428  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.348   2.253  -0.903  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.653   1.531  -0.035  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.069   2.264   1.193  1.00  0.00           C  
HETATM   16  H1  UNL     1      -1.153  -3.346   0.046  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.729  -3.426  -0.790  1.00  0.00           H  
HETATM   18  H3  UNL     1      -1.295  -3.066  -1.768  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.904  -1.499   0.372  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.855   0.855   1.122  1.00  0.00           H  
HETATM   21  H6  UNL     1      -3.935   0.937  -0.370  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.075   1.456  -1.739  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.548  -0.423  -1.927  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.339  -0.356   1.104  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.398  -0.247  -1.309  1.00  0.00           H  
HETATM   26  H11 UNL     1       2.102  -0.173   1.687  1.00  0.00           H  
HETATM   27  H12 UNL     1       3.636  -0.483  -0.950  1.00  0.00           H  
HETATM   28  H13 UNL     1       4.196   0.428   0.536  1.00  0.00           H  
HETATM   29  H14 UNL     1       4.208  -1.384   0.465  1.00  0.00           H  
HETATM   30  H15 UNL     1       0.967  -2.118   1.345  1.00  0.00           H  
HETATM   31  H16 UNL     1       2.661  -2.652   0.996  1.00  0.00           H  
HETATM   32  H17 UNL     1       1.511  -2.239  -0.389  1.00  0.00           H  
HETATM   33  H18 UNL     1       1.988   2.110   0.531  1.00  0.00           H  
HETATM   34  H19 UNL     1       2.409   1.826  -1.248  1.00  0.00           H  
HETATM   35  H20 UNL     1       0.393   3.341  -0.694  1.00  0.00           H  
HETATM   36  H21 UNL     1       0.241   2.019  -1.967  1.00  0.00           H  
HETATM   37  H22 UNL     1      -1.199   1.627   2.083  1.00  0.00           H  
HETATM   38  H23 UNL     1      -2.003   2.832   0.971  1.00  0.00           H  
HETATM   39  H24 UNL     1      -0.288   3.037   1.412  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    6
CONECT    3    4   19
CONECT    4    5   20   21
CONECT    5    6   14   22
CONECT    6    7   23
CONECT    7    8   14   24
CONECT    8    9   12   25
CONECT    9   10   11   26
CONECT   10   27   28   29
CONECT   11   30   31   32
CONECT   12   13   33   34
CONECT   13   14   35   36
CONECT   14   15
CONECT   15   37   38   39
END

HMDB0061850
     RDKit          3D
alpha-Bourbonene
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.7560   -2.8924   -0.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9575   -1.4341   -0.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460   -0.9244   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9786    0.5415    0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8254    0.9459   -0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0503   -0.3435   -0.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1156    0.1363    0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3033    0.1957   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2439   -0.5317    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6578   -0.4529    0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8334   -1.9989    0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6758    1.6549   -0.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483    2.2529   -0.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527    1.5308   -0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0691    2.2643    1.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1527   -3.3457    0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7287   -3.4258   -0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2953   -3.0662   -1.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9039   -1.4995    0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550    0.8554    1.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9346    0.9373   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747    1.4560   -1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5476   -0.4232   -1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3388   -0.3555    1.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3979   -0.2471   -1.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1024   -0.1731    1.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6358   -0.4834   -0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1959    0.4282    0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2083   -1.3840    0.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9675   -2.1179    1.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6608   -2.6521    0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5111   -2.2388   -0.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.1096    0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4092    1.8264   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3932    3.3406   -0.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407    2.0187   -1.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1995    1.6270    2.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0034    2.8320    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2883    3.0368    1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  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
 14  7  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 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
a-Bourbonene	Generator
Α-bourbonene	Generator
a-cis-Bergamotene	HMDB
Α-cis-bergamotene	HMDB

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.3511

Monoisotopic Molecular Weight

204.187800768

IUPAC Name

3,7-dimethyl-10-(propan-2-yl)tricyclo[5.3.0.0²,⁶]dec-3-ene

Traditional Name

10-isopropyl-3,7-dimethyltricyclo[5.3.0.0²,⁶]dec-3-ene

CAS Registry Number

Not Available

SMILES

CC(C)C1CCC2(C)C3CC=C(C)C3C12

InChI Identifier

InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)13(12)14(11)15/h5,9,11-14H,6-8H2,1-4H3

InChI Key

FAIMMSRDTUMTQR-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

Bourbonane 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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0061850)

Source

Endogenous

Endogenous (HMDB: HMDB0061850)

Animal

Animal (HMDB: HMDB0061850)

Exogenous

Food

Food (HMDB: HMDB0061850)

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)
Common oregano (FooDB: FOOD00124)

Exogenous (HMDB: HMDB0061850)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0061850)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0061850)

Lipid metabolism pathway (HMDB: HMDB0061850)

Cellular process

Cell signaling (HMDB: HMDB0061850)

Biochemical process

Lipid transport (HMDB: HMDB0061850)

Role

Biological role

Energy source (HMDB: HMDB0061850)

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	0.0018 g/L	ALOGPS
logP	3.85	ALOGPS
logP	4.09	ChemAxon
logS	-5	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	65.77 m³·mol⁻¹	ChemAxon
Polarizability	25.97 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]+	147.884	31661259
DarkChem	[M-H]-	144.419	31661259
DeepCCS	[M-2H]-	186.767	30932474
DeepCCS	[M+Na]+	162.076	30932474
AllCCS	[M+H]+	147.2	32859911
AllCCS	[M+H-H2O]+	143.3	32859911
AllCCS	[M+NH4]+	150.8	32859911
AllCCS	[M+Na]+	151.9	32859911
AllCCS	[M-H]-	158.3	32859911
AllCCS	[M+Na-2H]-	158.7	32859911
AllCCS	[M+HCOO]-	159.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Bourbonene	CC(C)C1CCC2(C)C3CC=C(C)C3C12	1579.0	Standard polar	33892256
alpha-Bourbonene	CC(C)C1CCC2(C)C3CC=C(C)C3C12	1374.9	Standard non polar	33892256
alpha-Bourbonene	CC(C)C1CCC2(C)C3CC=C(C)C3C12	1367.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Bourbonene GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-5900000000-9847e705c15174fceea6	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Bourbonene 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 - alpha-Bourbonene 10V, Positive-QTOF	splash10-0a4i-1390000000-3b5b314c577ce4b7ba77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bourbonene 20V, Positive-QTOF	splash10-0a4i-4960000000-e5546c599bde1ef4a8fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bourbonene 40V, Positive-QTOF	splash10-0pvi-9400000000-e17f23f8951b6dbd07d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bourbonene 10V, Negative-QTOF	splash10-0udi-0090000000-9fc6af0a86374be44980	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bourbonene 20V, Negative-QTOF	splash10-0udi-0190000000-c78ccaaa6c091faae3cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bourbonene 40V, Negative-QTOF	splash10-0f79-2910000000-876ac385a6bc4b1b4200	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bourbonene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bourbonene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bourbonene 40V, Negative-QTOF	splash10-0udi-0090000000-1ac141a9b7a368d60a94	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bourbonene 10V, Positive-QTOF	splash10-0a4i-1190000000-740c0d80a070abd745b4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bourbonene 20V, Positive-QTOF	splash10-00fr-4910000000-2289db2164eb019ea922	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bourbonene 40V, Positive-QTOF	splash10-004i-9100000000-bda24ee5de358a13426c	2021-09-24	Wishart Lab	View Spectrum

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

FDB005868

KNApSAcK ID

Not Available

Chemspider ID

462342

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

530816

PDB ID

Not Available

ChEBI ID

88649

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

Orav A, Raal A, Arak E: Essential oil composition of Pimpinella anisum L. fruits from various European countries. Nat Prod Res. 2008 Feb 15;22(3):227-32. doi: 10.1080/14786410701424667. [PubMed:18266152 ]
Schreier P, Drawert F, Junker A: [Sesquiterpene hydrocarbons from grapes (author's transl)]. Z Lebensm Unters Forsch. 1976;160(3):271-4. [PubMed:983335 ]
Roussis V, Vagias C, Tsitsimpikou C, Diamantopoulou N: Chemical variability of the volatile metabolites from the Caribbean corals of the genus Gorgonia. Z Naturforsch C. 2000 May-Jun;55(5-6):431-41. [PubMed:10928556 ]
Thoppil JE: Essential oil analysis of Eusteralis deccanensis Panigrahi (Lamiaceae). Boll Chim Farm. 2000 Jul-Aug;139(4):194-5. [PubMed:11059104 ]
Reza GH, Ebrahim S, Hossien H: Analysis by gas chromatography-mass spectrometry of essential oil from seeds and aerial parts of Ferulago angulata (Schlecht.) Boiss gathered in Nevakoh and Shahoo, Zagross mountain, West of Iran. Pak J Biol Sci. 2007 Mar 1;10(5):814-7. [PubMed:19069871 ]
Ozturk M, Tel G, Duru ME, Harmandar M, Topcu G: The effect of temperature on the essential oil components of Salvia potentillifolia obtained by various methods. Nat Prod Commun. 2009 Jul;4(7):1017-20. [PubMed:19731615 ]
Hajdari A, Mustafa B, Franz C, Novak J: Variability of essential oils of Betonica officinalis (Lamiaceae) from different wild populations in Kosovo. Nat Prod Commun. 2011 Sep;6(9):1343-6. [PubMed:21941911 ]
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.

Showing metabocard for alpha-Bourbonene (HMDB0061850)

MOL for HMDB0061850 (alpha-Bourbonene)

3D MOL for HMDB0061850 (alpha-Bourbonene)

3D SDF for HMDB0061850 (alpha-Bourbonene)

3D-SDF for HMDB0061850 (alpha-Bourbonene)

PDB for HMDB0061850 (alpha-Bourbonene)

3D PDB for HMDB0061850 (alpha-Bourbonene)

SMILES for HMDB0061850 (alpha-Bourbonene)

INCHI for HMDB0061850 (alpha-Bourbonene)

Structure for HMDB0061850 (alpha-Bourbonene)

3D Structure for HMDB0061850 (alpha-Bourbonene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra