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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 18:11:37 UTC

Update Date

2021-09-23 18:11:39 UTC

HMDB ID

HMDB0302493

Secondary Accession Numbers

None

Metabolite Identification

Common Name

gamma-Elemene

Description

Gamma-Elemene, also known as g-elemene, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenoids 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-erythritol-phosphate (MEP) pathway in the cytosol. 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. More formally, gamma-elemene is a cyclohexane substituted at positions 1, 1, 2, and 4 by methyl, vinyl, isopropenyl and isopropylidene groups, respectively. There are four known elemene isomers including ≈í¬±-, ≈í‚â§-, ≈í‚â•-, and ≈í¬•-elemene. The elemenes contribute to the floral aromas of some plants and are used as pheromones by some insects. Gamma-elemene is found in many essential plant oils including wormwood leaf oil, peppermint oil, pepper tree leaf oil, parsley leaf oil, orange peel oil, lime oil, juniper berry oil, hinoki leaf oil, angelica root oil, and angelica seed oil. Gamma-elemene has been shown to exhibit good insecticidal activity against the crop pest Spodoptera litura (tobacco cutworm or cotton leafworm) and could be useful as an eco-friendly biopesticide (PMID:28634795 ).

Structure

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

HMDB0302493
     RDKit          3D
gamma-Elemene
 39 39  0  0  0  0  0  0  0  0999 V2000
   -2.2025   -1.7580    2.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3838   -1.1501    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2769   -0.7265    0.0001 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7911   -0.6058   -1.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312   -1.8288    0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942   -1.5791   -0.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4849   -0.2538   -0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7833   -0.1163   -0.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6645   -1.2887   -0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3793    1.1912   -0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5494    0.8762   -0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6442    0.5336    0.4880 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5063    1.7030    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6940    2.2880    1.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2087    2.3214   -0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547   -2.0357    2.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304   -2.0058    2.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3951   -0.9453    0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0073   -1.6195   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7549   -0.0590   -1.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991   -0.1801   -2.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2459   -1.7808    1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6670   -2.8276   -0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5907   -1.5894   -1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457   -2.3586   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4784   -1.7332   -1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197   -0.9945   -0.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4425   -2.0835    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1654    1.3893    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559    2.0149   -0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4861    1.1737   -0.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2377    1.2832   -1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0960    1.6864    0.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2256    0.3289    1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2245    1.9202    2.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3167    3.1645    1.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6542    2.0718   -1.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0779    3.4374   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2735    2.1365   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 13 15  1  0
 12  3  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  4 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  1
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

6432312
  Mrv1652303202018592D          

 15 15  0  0  1  0            999 V2000
    3.7935    1.0313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0790    0.6188    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  7  1  1  0  0  0
  1  9  1  0  0  0  0
  2  4  1  0  0  0  0
  2  8  1  1  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  6 10  2  0  0  0  0
  8 11  1  0  0  0  0
  8 12  2  0  0  0  0
  9 13  2  0  0  0  0
 10 14  1  0  0  0  0
 10 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302493

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=C1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,14H,1,4,8-10H2,2-3,5-6H3/t14-,15+/m0/s1

> <INCHI_KEY>
BQSLMQNYHVFRDT-LSDHHAIUSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.80273333793611

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S)-1-ethenyl-1-methyl-2-(prop-1-en-2-yl)-4-(propan-2-ylidene)cyclohexane

> <ALOGPS_LOGP>
5.09

> <JCHEM_LOGP>
4.6353894833333324

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
69.0321

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S)-1-ethenyl-1-methyl-2-(prop-1-en-2-yl)-4-(propan-2-ylidene)cyclohexane

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302493
     RDKit          3D
gamma-Elemene
 39 39  0  0  0  0  0  0  0  0999 V2000
   -2.2025   -1.7580    2.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3838   -1.1501    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2769   -0.7265    0.0001 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7911   -0.6058   -1.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312   -1.8288    0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942   -1.5791   -0.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4849   -0.2538   -0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7833   -0.1163   -0.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6645   -1.2887   -0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3793    1.1912   -0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5494    0.8762   -0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6442    0.5336    0.4880 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5063    1.7030    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6940    2.2880    1.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2087    2.3214   -0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547   -2.0357    2.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304   -2.0058    2.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3951   -0.9453    0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0073   -1.6195   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7549   -0.0590   -1.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991   -0.1801   -2.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2459   -1.7808    1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6670   -2.8276   -0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5907   -1.5894   -1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457   -2.3586   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4784   -1.7332   -1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197   -0.9945   -0.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4425   -2.0835    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1654    1.3893    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559    2.0149   -0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4861    1.1737   -0.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2377    1.2832   -1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0960    1.6864    0.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2256    0.3289    1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2245    1.9202    2.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3167    3.1645    1.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6542    2.0718   -1.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0779    3.4374   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2735    2.1365   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 13 15  1  0
 12  3  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  4 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  1
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 6432312                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       7.081   1.925   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.747   1.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.415   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.747  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.415  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081  -1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.311   3.259   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   1.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.851   3.259   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -2.695   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080   1.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   3.465   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.391   3.259   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415  -3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.747  -3.465   0.000  0.00  0.00           C+0
CONECT    1    2    3    7    9                                             
CONECT    2    1    4    8                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   10                                                  
CONECT    7    1                                                            
CONECT    8    2   11   12                                                  
CONECT    9    1   13                                                       
CONECT   10    6   14   15                                                  
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15   10                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0302493
HETATM    1  C1  UNL     1      -2.202  -1.758   2.057  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.384  -1.150   0.898  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.277  -0.727   0.000  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.791  -0.606  -1.412  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.231  -1.829   0.055  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.894  -1.579  -0.921  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.485  -0.254  -0.551  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.783  -0.116  -0.380  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.665  -1.289  -0.555  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.379   1.191  -0.014  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.549   0.876  -0.391  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.644   0.534   0.488  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.506   1.703   0.536  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.694   2.288   1.717  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.209   2.321  -0.612  1.00  0.00           C  
HETATM   16  H1  UNL     1      -3.055  -2.036   2.655  1.00  0.00           H  
HETATM   17  H2  UNL     1      -1.230  -2.006   2.464  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.395  -0.945   0.578  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.007  -1.620  -1.847  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.755  -0.059  -1.470  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.999  -0.180  -2.048  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.246  -1.781   1.078  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.667  -2.828  -0.072  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.591  -1.589  -1.963  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.646  -2.359  -0.763  1.00  0.00           H  
HETATM   26  H11 UNL     1       3.478  -1.733  -1.559  1.00  0.00           H  
HETATM   27  H12 UNL     1       4.720  -0.995  -0.508  1.00  0.00           H  
HETATM   28  H13 UNL     1       3.442  -2.083   0.187  1.00  0.00           H  
HETATM   29  H14 UNL     1       3.165   1.389   1.057  1.00  0.00           H  
HETATM   30  H15 UNL     1       2.956   2.015  -0.632  1.00  0.00           H  
HETATM   31  H16 UNL     1       4.486   1.174  -0.166  1.00  0.00           H  
HETATM   32  H17 UNL     1       0.238   1.283  -1.360  1.00  0.00           H  
HETATM   33  H18 UNL     1       1.096   1.686   0.149  1.00  0.00           H  
HETATM   34  H19 UNL     1      -0.226   0.329   1.487  1.00  0.00           H  
HETATM   35  H20 UNL     1      -1.225   1.920   2.644  1.00  0.00           H  
HETATM   36  H21 UNL     1      -2.317   3.165   1.865  1.00  0.00           H  
HETATM   37  H22 UNL     1      -1.654   2.072  -1.542  1.00  0.00           H  
HETATM   38  H23 UNL     1      -2.078   3.437  -0.498  1.00  0.00           H  
HETATM   39  H24 UNL     1      -3.273   2.136  -0.653  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3   18
CONECT    3    4    5   12
CONECT    4   19   20   21
CONECT    5    6   22   23
CONECT    6    7   24   25
CONECT    7    8    8   11
CONECT    8    9   10
CONECT    9   26   27   28
CONECT   10   29   30   31
CONECT   11   12   32   33
CONECT   12   13   34
CONECT   13   14   14   15
CONECT   14   35   36
CONECT   15   37   38   39
END

HMDB0302493
     RDKit          3D
gamma-Elemene
 39 39  0  0  0  0  0  0  0  0999 V2000
   -2.2025   -1.7580    2.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3838   -1.1501    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2769   -0.7265    0.0001 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7911   -0.6058   -1.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312   -1.8288    0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942   -1.5791   -0.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4849   -0.2538   -0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7833   -0.1163   -0.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6645   -1.2887   -0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3793    1.1912   -0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5494    0.8762   -0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6442    0.5336    0.4880 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5063    1.7030    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6940    2.2880    1.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2087    2.3214   -0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547   -2.0357    2.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304   -2.0058    2.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3951   -0.9453    0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0073   -1.6195   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7549   -0.0590   -1.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991   -0.1801   -2.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2459   -1.7808    1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6670   -2.8276   -0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5907   -1.5894   -1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457   -2.3586   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4784   -1.7332   -1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197   -0.9945   -0.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4425   -2.0835    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1654    1.3893    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559    2.0149   -0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4861    1.1737   -0.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2377    1.2832   -1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0960    1.6864    0.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2256    0.3289    1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2245    1.9202    2.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3167    3.1645    1.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6542    2.0718   -1.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0779    3.4374   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2735    2.1365   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 13 15  1  0
 12  3  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  4 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  1
 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
(+)-gamma-Elemene	ChEBI
(+)-g-Elemene	Generator
(+)-Γ-elemene	Generator
g-Elemene	Generator
Γ-elemene	Generator

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.357

Monoisotopic Molecular Weight

204.187800773

IUPAC Name

(1S,2S)-1-ethenyl-1-methyl-2-(prop-1-en-2-yl)-4-(propan-2-ylidene)cyclohexane

Traditional Name

(1S,2S)-1-ethenyl-1-methyl-2-(prop-1-en-2-yl)-4-(propan-2-ylidene)cyclohexane

CAS Registry Number

Not Available

SMILES

CC(C)=C1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C

InChI Identifier

InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,14H,1,4,8-10H2,2-3,5-6H3/t14-,15+/m0/s1

InChI Key

BQSLMQNYHVFRDT-LSDHHAIUSA-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
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Milk and milk product

Fermented milk product

Cheese (FooDB: FOOD00617)

Herb and spice

Herb

Spice

Caraway (FooDB: FOOD00043)

Fruit

Citrus

Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

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	5.09	ALOGPS
logP	4.64	ChemAxon
logS	-4.4	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.03 m³·mol⁻¹	ChemAxon
Polarizability	25.8 Å³	ChemAxon
Number of Rings	1	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]+	146.772	32859911
AllCCS	[M+H-H2O]+	142.868	32859911
AllCCS	[M+Na]+	151.451	32859911
AllCCS	[M+NH4]+	150.404	32859911
AllCCS	[M-H]-	154.586	32859911
AllCCS	[M+Na-2H]-	155.288	32859911
AllCCS	[M+HCOO]-	156.16	32859911
DeepCCS	[M+H]+	155.924	30932474
DeepCCS	[M-H]-	153.566	30932474
DeepCCS	[M-2H]-	186.452	30932474
DeepCCS	[M+Na]+	162.018	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Elemene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0019-4900000000-fb790115baaf4a3d1616	2017-07-27	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 - gamma-Elemene 10V, Negative-QTOF	splash10-0udi-0090000000-6bfd709831d5599e9c1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Elemene 20V, Negative-QTOF	splash10-0udi-0290000000-b951c20dccfd334852ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Elemene 40V, Negative-QTOF	splash10-000i-1900000000-9c9cef0e084401e873e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Elemene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Elemene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Elemene 40V, Negative-QTOF	splash10-0zg0-0940000000-75fae33c5b380ac99591	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Elemene 10V, Positive-QTOF	splash10-0a4i-1890000000-450e146224ccff06d617	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Elemene 20V, Positive-QTOF	splash10-07br-3910000000-61daee527832bc181130	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Elemene 40V, Positive-QTOF	splash10-0gb9-9300000000-84044dadf41caec7632f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Elemene 10V, Positive-QTOF	splash10-022i-0900000000-b8727734b8bc280cd807	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Elemene 20V, Positive-QTOF	splash10-053r-9710000000-8f184d721121df33f4dc	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Elemene 40V, Positive-QTOF	splash10-069u-9300000000-dc6712d7b870be6f2b3a	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

FDB004787

KNApSAcK ID

C00012012

Chemspider ID

4937571

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

132656

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

Benelli G, Govindarajan M, AlSalhi MS, Devanesan S, Maggi F: High toxicity of camphene and gamma-elemene from Wedelia prostrata essential oil against larvae of Spodoptera litura (Lepidoptera: Noctuidae). Environ Sci Pollut Res Int. 2018 Apr;25(11):10383-10391. doi: 10.1007/s11356-017-9490-7. Epub 2017 Jun 20. [PubMed:28634795 ]

Showing metabocard for gamma-Elemene (HMDB0302493)

MOL for HMDB0302493 (gamma-Elemene)

3D MOL for HMDB0302493 (gamma-Elemene)

3D SDF for HMDB0302493 (gamma-Elemene)

3D-SDF for HMDB0302493 (gamma-Elemene)

PDB for HMDB0302493 (gamma-Elemene)

3D PDB for HMDB0302493 (gamma-Elemene)

SMILES for HMDB0302493 (gamma-Elemene)

INCHI for HMDB0302493 (gamma-Elemene)

Structure for HMDB0302493 (gamma-Elemene)

3D Structure for HMDB0302493 (gamma-Elemene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra