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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:18:40 UTC

Update Date

2021-09-23 16:18:43 UTC

HMDB ID

HMDB0302249

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(E)-alpha-Bergamotene

Description

≈í¬±-cis-bergamotene belongs to the class of organic compounds known as bicyclic sesquiterpenoids. These are sesquiterpenoids containing exactly two rings, which are fused together. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpene as it is synthesized via isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are four known Bergamotene isomers including ≈í¬±-cis-, ≈í¬±-trans-, ≈í‚â§-cis- and ≈í‚â§-trans-bergamotene. ≈í¬±-cis-Bergamotene is found in the oils of carrot, bergamot, lime, citron, cottonseed, and kumquat. Isomers of bergamotene have a function as pheromones for some insect species. Evidence suggests that plants under attack by herbivore insects are able to release specific amounts of bergamotene to attract natural enemies of the herbivores, using these sesquiterpenes as a defense mechanism (PMID: 16418295 ).

Structure

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

HMDB0302249
     RDKit          3D
(E)-alpha-Bergamotene
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.1481   -0.8755    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950   -0.3315   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7105    1.0752   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6983   -1.0666   -0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735   -0.4863   -0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5120   -0.5594    0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693   -0.0534    0.6021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5649   -0.2286    1.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700    1.3516    0.1136 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4244    1.9074    0.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4763    0.9831    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1576   -0.2745   -0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0984   -1.4092   -0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7180   -0.5048   -0.5608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3290    0.7643   -1.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2527   -0.9642    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2013   -1.9263   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9482   -0.2996   -0.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311    1.1629   -1.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7160    1.5409   -0.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917    1.6979   -0.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8135   -2.0953    0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0128   -1.0402   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5346    0.6096   -0.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4534   -1.6413    1.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0185   -0.0504    1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910    0.6278    2.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6270   -0.4387    1.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0993   -1.1352    2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2349    2.0370    0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4058    2.0466    1.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5481    2.8694    0.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4785    1.3235   -0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6005   -1.5401   -1.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8242   -1.2893    0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976   -2.3245    0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4994   -1.4511   -1.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024    1.2544   -1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4944    0.7343   -1.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  7  6  1  1
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14  7  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 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  6
 10 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  6
 15 38  1  0
 15 39  1  0
M  END


  Mrv1652303202019022D          

 15 16  0  0  0  0            999 V2000
   -2.9188    2.0331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2044    1.6205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2044    0.7955    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9188    0.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6333    0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6333    1.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2044    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4899    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7754    1.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0610    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6535    1.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3680    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6535    0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9188    1.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  7  1  6  0  0  0
  2  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  3 14  1  1  0  0  0
  1 14  1  1  0  0  0
  6 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302249

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC[C@@]1(C)[C@H]2C[C@@H]1C(C)=CC2

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6-7,13-14H,5,8-10H2,1-4H3/t13-,14-,15+/m1/s1

> <INCHI_KEY>
YMBFCQPIMVLNIU-KFWWJZLASA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.576364696354496

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene

> <ALOGPS_LOGP>
5.91

> <JCHEM_LOGP>
4.461375721333334

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
68.5249

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302249
     RDKit          3D
(E)-alpha-Bergamotene
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.1481   -0.8755    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950   -0.3315   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7105    1.0752   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6983   -1.0666   -0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735   -0.4863   -0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5120   -0.5594    0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693   -0.0534    0.6021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5649   -0.2286    1.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700    1.3516    0.1136 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4244    1.9074    0.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4763    0.9831    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1576   -0.2745   -0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0984   -1.4092   -0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7180   -0.5048   -0.5608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3290    0.7643   -1.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2527   -0.9642    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2013   -1.9263   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9482   -0.2996   -0.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311    1.1629   -1.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7160    1.5409   -0.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917    1.6979   -0.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8135   -2.0953    0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0128   -1.0402   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5346    0.6096   -0.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4534   -1.6413    1.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0185   -0.0504    1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910    0.6278    2.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6270   -0.4387    1.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0993   -1.1352    2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2349    2.0370    0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4058    2.0466    1.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5481    2.8694    0.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4785    1.3235   -0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6005   -1.5401   -1.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8242   -1.2893    0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976   -2.3245    0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4994   -1.4511   -1.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024    1.2544   -1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4944    0.7343   -1.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  7  6  1  1
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14  7  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 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  6
 10 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  6
 15 38  1  0
 15 39  1  0
M  END

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      -5.448   3.795   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.115   3.025   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.115   1.485   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.448   0.715   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.782   1.485   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.782   3.025   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.115   4.565   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.781   3.795   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.447   3.025   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.114   3.795   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.220   3.025   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.554   3.795   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.220   1.485   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.448   2.255   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.116   3.795   0.000  0.00  0.00           C+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3    7    8                                             
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5   15                                                  
CONECT    7    2                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    3    1                                                       
CONECT   15    6                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0302249
HETATM    1  C1  UNL     1       5.148  -0.875   0.096  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.795  -0.332  -0.249  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.710   1.075  -0.705  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.698  -1.067  -0.157  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.373  -0.486  -0.510  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.512  -0.559   0.685  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.869  -0.053   0.602  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.565  -0.229   1.957  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.070   1.352   0.114  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.424   1.907   0.563  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.476   0.983   0.089  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.158  -0.274  -0.146  1.00  0.00           C  
HETATM   13  C13 UNL     1      -4.098  -1.409  -0.026  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.718  -0.505  -0.561  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.329   0.764  -1.275  1.00  0.00           C  
HETATM   16  H1  UNL     1       5.253  -0.964   1.190  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.201  -1.926  -0.311  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.948  -0.300  -0.369  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.231   1.163  -1.707  1.00  0.00           H  
HETATM   20  H5  UNL     1       4.716   1.541  -0.750  1.00  0.00           H  
HETATM   21  H6  UNL     1       3.092   1.698  -0.002  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.813  -2.095   0.183  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.013  -1.040  -1.389  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.535   0.610  -0.730  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.453  -1.641   1.004  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.019  -0.050   1.537  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.291   0.628   2.599  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.627  -0.439   1.883  1.00  0.00           H  
HETATM   29  H14 UNL     1      -1.099  -1.135   2.421  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.235   2.037   0.185  1.00  0.00           H  
HETATM   31  H16 UNL     1      -2.406   2.047   1.651  1.00  0.00           H  
HETATM   32  H17 UNL     1      -2.548   2.869   0.024  1.00  0.00           H  
HETATM   33  H18 UNL     1      -4.479   1.324  -0.062  1.00  0.00           H  
HETATM   34  H19 UNL     1      -4.601  -1.540  -1.017  1.00  0.00           H  
HETATM   35  H20 UNL     1      -4.824  -1.289   0.791  1.00  0.00           H  
HETATM   36  H21 UNL     1      -3.498  -2.325   0.153  1.00  0.00           H  
HETATM   37  H22 UNL     1      -1.499  -1.451  -1.026  1.00  0.00           H  
HETATM   38  H23 UNL     1      -2.202   1.254  -1.797  1.00  0.00           H  
HETATM   39  H24 UNL     1      -0.494   0.734  -1.961  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4    4
CONECT    3   19   20   21
CONECT    4    5   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8    9   14
CONECT    8   27   28   29
CONECT    9   10   15   30
CONECT   10   11   31   32
CONECT   11   12   12   33
CONECT   12   13   14
CONECT   13   34   35   36
CONECT   14   15   37
CONECT   15   38   39
END

HMDB0302249
     RDKit          3D
(E)-alpha-Bergamotene
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.1481   -0.8755    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950   -0.3315   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7105    1.0752   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6983   -1.0666   -0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735   -0.4863   -0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5120   -0.5594    0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693   -0.0534    0.6021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5649   -0.2286    1.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700    1.3516    0.1136 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4244    1.9074    0.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4763    0.9831    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1576   -0.2745   -0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0984   -1.4092   -0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7180   -0.5048   -0.5608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3290    0.7643   -1.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2527   -0.9642    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2013   -1.9263   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9482   -0.2996   -0.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311    1.1629   -1.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7160    1.5409   -0.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917    1.6979   -0.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8135   -2.0953    0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0128   -1.0402   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5346    0.6096   -0.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4534   -1.6413    1.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0185   -0.0504    1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910    0.6278    2.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6270   -0.4387    1.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0993   -1.1352    2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2349    2.0370    0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4058    2.0466    1.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5481    2.8694    0.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4785    1.3235   -0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6005   -1.5401   -1.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8242   -1.2893    0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976   -2.3245    0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4994   -1.4511   -1.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024    1.2544   -1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4944    0.7343   -1.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  7  6  1  1
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14  7  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 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  6
 10 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  6
 15 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-a-Bergamotene	Generator
(e)-Α-bergamotene	Generator

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.3511

Monoisotopic Molecular Weight

204.187800768

IUPAC Name

(1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene

Traditional Name

(1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene

CAS Registry Number

Not Available

SMILES

CC(C)=CCC[C@@]1(C)[C@H]2C[C@@H]1C(C)=CC2

InChI Identifier

InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6-7,13-14H,5,8-10H2,1-4H3/t13-,14-,15+/m1/s1

InChI Key

YMBFCQPIMVLNIU-KFWWJZLASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Pinane monoterpenoid
Bicyclic monoterpenoid
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

Not Available

Lime (FooDB: FOOD00053)

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	5.91	ALOGPS
logP	4.46	ChemAxon
logS	-4.5	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.52 m³·mol⁻¹	ChemAxon
Polarizability	26.58 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
AllCCS	[M+H]+	148.842	32859911
AllCCS	[M+H-H2O]+	144.979	32859911
AllCCS	[M+Na]+	153.471	32859911
AllCCS	[M+NH4]+	152.436	32859911
AllCCS	[M-H]-	158.308	32859911
AllCCS	[M+Na-2H]-	158.871	32859911
AllCCS	[M+HCOO]-	159.598	32859911
DeepCCS	[M+H]+	152.126	30932474
DeepCCS	[M-H]-	149.73	30932474
DeepCCS	[M-2H]-	182.794	30932474
DeepCCS	[M+Na]+	158.129	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-alpha-Bergamotene 10V, Positive-QTOF	splash10-0a4i-1390000000-d6a0ba11c5a26587cd86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-alpha-Bergamotene 20V, Positive-QTOF	splash10-0aor-4940000000-9dc882467486d9fdf061	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-alpha-Bergamotene 40V, Positive-QTOF	splash10-014i-5900000000-ea9024d4d9b8c46f7756	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-alpha-Bergamotene 10V, Negative-QTOF	splash10-0udi-0090000000-1d073790940a713722d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-alpha-Bergamotene 20V, Negative-QTOF	splash10-0udi-0090000000-de5ae459f3052d9744b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-alpha-Bergamotene 40V, Negative-QTOF	splash10-0fy9-3910000000-729cba2ca70dcf19f20f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-alpha-Bergamotene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-alpha-Bergamotene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-alpha-Bergamotene 40V, Negative-QTOF	splash10-0uxr-0790000000-5f2697dd150bf0825ae5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-alpha-Bergamotene 10V, Positive-QTOF	splash10-060r-2920000000-b37f23a73e76ccb77633	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-alpha-Bergamotene 20V, Positive-QTOF	splash10-00di-3900000000-bdedd611b0ff9d625863	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-alpha-Bergamotene 40V, Positive-QTOF	splash10-069r-9000000000-b2a695a52a29c98c4260	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003887

KNApSAcK ID

Not Available

Chemspider ID

10250932

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13889654

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

Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]
Schnee C, Kollner TG, Held M, Turlings TC, Gershenzon J, Degenhardt J: The products of a single maize sesquiterpene synthase form a volatile defense signal that attracts natural enemies of maize herbivores. Proc Natl Acad Sci U S A. 2006 Jan 24;103(4):1129-34. doi: 10.1073/pnas.0508027103. Epub 2006 Jan 17. [PubMed:16418295 ]

Showing metabocard for (E)-alpha-Bergamotene (HMDB0302249)

MOL for HMDB0302249 ((E)-alpha-Bergamotene)

3D MOL for HMDB0302249 ((E)-alpha-Bergamotene)

3D SDF for HMDB0302249 ((E)-alpha-Bergamotene)

3D-SDF for HMDB0302249 ((E)-alpha-Bergamotene)

PDB for HMDB0302249 ((E)-alpha-Bergamotene)

3D PDB for HMDB0302249 ((E)-alpha-Bergamotene)

SMILES for HMDB0302249 ((E)-alpha-Bergamotene)

INCHI for HMDB0302249 ((E)-alpha-Bergamotene)

Structure for HMDB0302249 ((E)-alpha-Bergamotene)

3D Structure for HMDB0302249 ((E)-alpha-Bergamotene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra