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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-08 15:55:48 UTC

Update Date

2021-09-14 15:45:27 UTC

HMDB ID

HMDB0061848

Secondary Accession Numbers

HMDB0035816
HMDB35816
HMDB61848

Metabolite Identification

Common Name

beta-Elemene

Description

beta-Elemene belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. beta-Elemene can be found in herbs, spices, and root vegetables, which makes beta-elemene a potential biomarker for the consumption of these food products. It is a constituent of sweet flag, juniper oils, and Mentha species.

Structure

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

HMDB0061848
     RDKit          3D
beta-Elemene
 39 39  0  0  0  0  0  0  0  0999 V2000
   -1.7221   -0.8400    2.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9315   -1.3192    1.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935   -0.7780   -0.0196 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4243   -0.8761   -1.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2796   -1.7953   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -1.6617    0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4247   -0.3209    0.6539 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8805   -0.0389    0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686   -0.9472    0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3334    1.3111    1.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7413    0.7034   -0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7653    0.5934    0.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4533    1.5671   -0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806    2.5843   -0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    1.4610   -2.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2329   -1.2901    3.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0880   -0.0198    2.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6311   -2.1784    1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643   -0.0722   -0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9554   -1.8290   -0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0301   -1.0120   -2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6494   -2.8279   -0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2669   -1.7686   -1.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3622   -2.4936    0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8144   -1.7681   -0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0004   -0.2709    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8235   -0.6575    0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5814   -1.9356   -0.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    1.8263    1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8005    1.8504    0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339    1.1165    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0489    1.7015    0.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9546    0.5101   -1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    0.9755    1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1084    2.7302    0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    3.2944   -0.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4202    1.2329   -2.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1597    2.4521   -2.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6102    0.7909   -2.6854 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  1  0
  8  9  2  3
  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
  7 26  1  1
  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


  Mrv1652309272007312D          

 15 15  0  0  0  0            999 V2000
10006.833510006.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.548710006.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.833510007.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.408410007.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.694410008.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.122410007.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.408410004.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.694410004.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.122410004.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.407010006.9363    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10004.692110006.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.692110005.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.407010005.2853    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10006.122010005.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.122010006.5235    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  4  5  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15  1  1  6  0  0  0
 10  4  1  0  0  0  0
 10  6  1  6  0  0  0
 13  7  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0061848

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)[C@@H]1CC[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/h7,13-14H,1-2,4,8-10H2,3,5-6H3/t13-,14+,15-/m1/s1

> <INCHI_KEY>
OPFTUNCRGUEPRZ-QLFBSQMISA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.972700408875248

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.40

> <JCHEM_LOGP>
4.736980978333334

> <ALOGPS_LOGS>
-4.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
68.22619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-elemene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061848
     RDKit          3D
beta-Elemene
 39 39  0  0  0  0  0  0  0  0999 V2000
   -1.7221   -0.8400    2.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9315   -1.3192    1.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935   -0.7780   -0.0196 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4243   -0.8761   -1.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2796   -1.7953   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -1.6617    0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4247   -0.3209    0.6539 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8805   -0.0389    0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686   -0.9472    0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3334    1.3111    1.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7413    0.7034   -0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7653    0.5934    0.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4533    1.5671   -0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806    2.5843   -0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    1.4610   -2.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2329   -1.2901    3.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0880   -0.0198    2.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6311   -2.1784    1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643   -0.0722   -0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9554   -1.8290   -0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0301   -1.0120   -2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6494   -2.8279   -0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2669   -1.7686   -1.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3622   -2.4936    0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8144   -1.7681   -0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0004   -0.2709    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8235   -0.6575    0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5814   -1.9356   -0.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    1.8263    1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8005    1.8504    0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339    1.1165    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0489    1.7015    0.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9546    0.5101   -1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    0.9755    1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1084    2.7302    0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    3.2944   -0.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4202    1.2329   -2.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1597    2.4521   -2.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6102    0.7909   -2.6854 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  1  0
  8  9  2  3
  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
  7 26  1  1
  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                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8679.4238679.612   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8680.7578678.842   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8679.4238681.151   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8676.7628681.151   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8675.4308681.920   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8678.0958680.381   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8676.7628674.997   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8675.4308674.226   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8678.0958674.226   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8676.7608679.614   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8675.4258678.844   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8675.4258677.303   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8676.7608676.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8678.0948677.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8678.0948678.844   0.000  0.00  0.00           C+0
CONECT    1    2    3   15                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    5   10                                                       
CONECT    5    4                                                            
CONECT    6   10                                                            
CONECT    7    8    9   13                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10   11   15    4    6                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14    7                                                  
CONECT   14   13   15                                                       
CONECT   15   10   14    1                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0061848
HETATM    1  C1  UNL     1      -1.722  -0.840   2.394  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.931  -1.319   1.202  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.294  -0.778  -0.020  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.424  -0.876  -1.079  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.280  -1.795  -0.485  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.096  -1.662   0.057  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.425  -0.321   0.654  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.881  -0.039   0.691  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.769  -0.947   0.319  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.333   1.311   1.164  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.741   0.703  -0.257  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.765   0.593   0.064  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.453   1.567  -0.845  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.081   2.584  -0.283  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.441   1.461  -2.316  1.00  0.00           C  
HETATM   16  H1  UNL     1      -2.233  -1.290   3.286  1.00  0.00           H  
HETATM   17  H2  UNL     1      -1.088  -0.020   2.682  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.631  -2.178   1.131  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.164  -0.072  -0.938  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.955  -1.829  -0.841  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.030  -1.012  -2.086  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.649  -2.828  -0.224  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.267  -1.769  -1.609  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.362  -2.494   0.731  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.814  -1.768  -0.820  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.000  -0.271   1.666  1.00  0.00           H  
HETATM   27  H12 UNL     1       4.824  -0.658   0.377  1.00  0.00           H  
HETATM   28  H13 UNL     1       3.581  -1.936  -0.025  1.00  0.00           H  
HETATM   29  H14 UNL     1       2.464   1.826   1.591  1.00  0.00           H  
HETATM   30  H15 UNL     1       3.800   1.850   0.323  1.00  0.00           H  
HETATM   31  H16 UNL     1       4.034   1.116   2.009  1.00  0.00           H  
HETATM   32  H17 UNL     1       1.049   1.702   0.104  1.00  0.00           H  
HETATM   33  H18 UNL     1       0.955   0.510  -1.308  1.00  0.00           H  
HETATM   34  H19 UNL     1      -0.836   0.975   1.092  1.00  0.00           H  
HETATM   35  H20 UNL     1      -2.108   2.730   0.803  1.00  0.00           H  
HETATM   36  H21 UNL     1      -2.586   3.294  -0.942  1.00  0.00           H  
HETATM   37  H22 UNL     1      -2.420   1.233  -2.778  1.00  0.00           H  
HETATM   38  H23 UNL     1      -1.160   2.452  -2.799  1.00  0.00           H  
HETATM   39  H24 UNL     1      -0.610   0.791  -2.685  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   11   26
CONECT    8    9    9   10
CONECT    9   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

HMDB0061848
     RDKit          3D
beta-Elemene
 39 39  0  0  0  0  0  0  0  0999 V2000
   -1.7221   -0.8400    2.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9315   -1.3192    1.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935   -0.7780   -0.0196 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4243   -0.8761   -1.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2796   -1.7953   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -1.6617    0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4247   -0.3209    0.6539 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8805   -0.0389    0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686   -0.9472    0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3334    1.3111    1.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7413    0.7034   -0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7653    0.5934    0.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4533    1.5671   -0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806    2.5843   -0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    1.4610   -2.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2329   -1.2901    3.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0880   -0.0198    2.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6311   -2.1784    1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643   -0.0722   -0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9554   -1.8290   -0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0301   -1.0120   -2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6494   -2.8279   -0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2669   -1.7686   -1.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3622   -2.4936    0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8144   -1.7681   -0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0004   -0.2709    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8235   -0.6575    0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5814   -1.9356   -0.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    1.8263    1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8005    1.8504    0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339    1.1165    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0489    1.7015    0.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9546    0.5101   -1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    0.9755    1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1084    2.7302    0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    3.2944   -0.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4202    1.2329   -2.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1597    2.4521   -2.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6102    0.7909   -2.6854 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  1  0
  8  9  2  3
  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
  7 26  1  1
  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
(1S,2S,4R)-(-)-1-Methyl-1-vinyl-2,4-diisopropenylcyclohexane	ChEBI
(1S,2S,4R)-1-Methyl-2,4-di(prop-1-en-2-yl)-1-vinylcyclohexane	ChEBI
(1S,2S,4R)-2,4-Diisopropenyl-1-methyl-1-vinylcyclohexane	ChEBI
2,4-Diisopropenyl-1-methyl-1-vinylcyclohexane	ChEBI
beta-Elemen	ChEBI
Levo-beta-elemene	ChEBI
b-Elemen	Generator
Β-elemen	Generator
Levo-b-elemene	Generator
Levo-β-elemene	Generator
b-Elemene	Generator
Β-elemene	Generator
(-)-b-Elemene	HMDB
(-)-beta-Elemene	HMDB
beta-Elemene	ChEBI
(-)-β-Elemene	Generator
(1S,2S,4R)-1-Ethenyl-1-methyl-2,4-bis(1-methylethenyl)cyclohexane	PhytoBank
(±)-beta-Elemene	PhytoBank
(±)-β-Elemene	PhytoBank

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.3511

Monoisotopic Molecular Weight

204.187800768

IUPAC Name

(1S,2S,4R)-1-ethenyl-1-methyl-2,4-bis(prop-1-en-2-yl)cyclohexane

Traditional Name

β-elemene

CAS Registry Number

515-13-9

SMILES

CC(=C)[C@@H]1CC[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/h7,13-14H,1-2,4,8-10H2,3,5-6H3/t13-,14+,15-/m1/s1

InChI Key

OPFTUNCRGUEPRZ-QLFBSQMISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Elemane sesquiterpenoids

Alternative Parents

Substituents

Elemane sesquiterpenoid
Branched unsaturated hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

beta-elemene (CHEBI:62855 )

Ontology

Saliva (HMDB: HMDB0061848)

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0061848)

Source

Endogenous

Endogenous (HMDB: HMDB0061848)

Plant

Plant (HMDB: HMDB0061848)

Animal

Animal (HMDB: HMDB0061848)

Exogenous

Food

Food (HMDB: HMDB0061848)

Vegetable

Root vegetable

Tuber

Potato (FooDB: FOOD00175)

Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Tropical fruit

Tamarind (FooDB: FOOD00180)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0061848)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0061848)

Cellular process

Cell signaling (HMDB: HMDB0061848)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0061848)

Role

Biological role

Nutrient

Nutrient (HMDB: HMDB0061848)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0061848)

Emulsifier (HMDB: HMDB0061848)

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	0.004 g/L	ALOGPS
logP	5.4	ALOGPS
logP	4.74	ChemAxon
logS	-4.7	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	68.23 m³·mol⁻¹	ChemAxon
Polarizability	25.97 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
DarkChem	[M+H]+	152.046	31661259
DarkChem	[M-H]-	148.557	31661259
DeepCCS	[M+H]+	153.013	30932474
DeepCCS	[M-H]-	150.618	30932474
DeepCCS	[M-2H]-	184.388	30932474
DeepCCS	[M+Na]+	159.437	30932474
AllCCS	[M+H]+	147.6	32859911
AllCCS	[M+H-H2O]+	143.6	32859911
AllCCS	[M+NH4]+	151.2	32859911
AllCCS	[M+Na]+	152.2	32859911
AllCCS	[M-H]-	154.8	32859911
AllCCS	[M+Na-2H]-	155.6	32859911
AllCCS	[M+HCOO]-	156.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Elemene	CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C	1602.9	Standard polar	33892256
beta-Elemene	CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C	1406.3	Standard non polar	33892256
beta-Elemene	CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C	1409.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - beta-Elemene EI-B (Non-derivatized)	splash10-055f-9300000000-0289c8de75fe9d63ecbe	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - beta-Elemene EI-B (Non-derivatized)	splash10-0a5c-9300000000-5b0ee4d8b7869c2f1150	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - beta-Elemene EI-B (Non-derivatized)	splash10-055f-9300000000-0289c8de75fe9d63ecbe	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - beta-Elemene EI-B (Non-derivatized)	splash10-0a5c-9300000000-5b0ee4d8b7869c2f1150	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - beta-Elemene GC-EI-Q (Non-derivatized)	splash10-00kf-9500000000-bf13cd3bd5550f5ba5c9	2020-07-08	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Elemene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0080-5900000000-01235238c52dcbb6dd6b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Elemene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Elemene 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 - beta-Elemene 10V, Positive-QTOF	splash10-0a4i-1790000000-453c5a1555b65a45bbf6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Elemene 20V, Positive-QTOF	splash10-06ri-4910000000-01642b086e5ae7d47ddf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Elemene 40V, Positive-QTOF	splash10-0gb9-9300000000-8a8cfd7c816b632bb230	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Elemene 10V, Negative-QTOF	splash10-0udi-0090000000-c96ee5d6723e9d3e562c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Elemene 20V, Negative-QTOF	splash10-0udi-0190000000-650d4bfb37438f455f35	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Elemene 40V, Negative-QTOF	splash10-000i-1900000000-0f6b74b8fa42644d3cd0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Elemene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Elemene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Elemene 40V, Negative-QTOF	splash10-0zg0-0940000000-2cbeadbe4dfea2ed5383	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Elemene 10V, Positive-QTOF	splash10-059i-0910000000-4293e9b1be9fc1d09c27	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Elemene 20V, Positive-QTOF	splash10-05cr-9710000000-733055659972947a1171	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Elemene 40V, Positive-QTOF	splash10-00mo-9300000000-b061378f98f19194e1c5	2021-09-22	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6918391

PDB ID

Not Available

ChEBI ID

62855

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

Li Z, Wang K, Chen YR, Wu XY, Su CY: [Studies on metabolite of beta-elemene in rat bile]. Yao Xue Xue Bao. 2000 Nov;35(11):829-31. [PubMed:11218859 ]
Wang K, Su CY: [Pharmacokinetics and disposition of beta-elemene in rats]. Yao Xue Xue Bao. 2000 Oct;35(10):725-8. [PubMed:11372435 ]
Zou L, Liu W, Yu L: [beta-elemene induces apoptosis of K562 leukemia cells]. Zhonghua Zhong Liu Za Zhi. 2001 May;23(3):196-8. [PubMed:11783084 ]
Chen SL, You J, Wang GJ: [Supercritical fluid extraction of beta-elemene under lower pressure]. Se Pu. 2001 Mar;19(2):179-81. [PubMed:12541670 ]
Wang K, Li Z, Chen YR, Wu XY, Li SY, Su CY: [Excretion of beta-elemene from rat respiratory tracts]. Yao Xue Xue Bao. 2005 Jan;40(1):54-6. [PubMed:15881328 ]
Zhang BJ, Li WC, Liu XP: [The pharmacokinetics of long-circulating beta-elemene liposomes]. Zhong Yao Cai. 2012 Sep;35(9):1464-8. [PubMed:23451504 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
YUREN CHEN, 'BETA-ELEMENE, METHOD TO PREPARE THE SAME AND USES THEREOF.' U.S. Patent US20020155522, issued October 24, 2002. [Link]
Yuren Chen, 'Beta-elemene, method to prepare the same and uses thereof.' U.S. Patent US20030216605, issued November 20, 2003. [Link]
Lan Huang, 'Synthesis of beta-elemene, intermediates thereto, analogues and uses thereof.' U.S. Patent US20060014987, issued January 19, 2006. [Link]

Showing metabocard for beta-Elemene (HMDB0061848)

MOL for HMDB0061848 (beta-Elemene)

3D MOL for HMDB0061848 (beta-Elemene)

3D SDF for HMDB0061848 (beta-Elemene)

3D-SDF for HMDB0061848 (beta-Elemene)

PDB for HMDB0061848 (beta-Elemene)

3D PDB for HMDB0061848 (beta-Elemene)

SMILES for HMDB0061848 (beta-Elemene)

INCHI for HMDB0061848 (beta-Elemene)

Structure for HMDB0061848 (beta-Elemene)

3D Structure for HMDB0061848 (beta-Elemene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra