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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 21:08:06 UTC

Update Date

2022-03-07 02:54:46 UTC

HMDB ID

HMDB0036065

Secondary Accession Numbers

HMDB36065

Metabolite Identification

Common Name

alpha-Farnesene

Description

alpha-Farnesene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (3E,6E)-alpha-Farnesene, also known as trans-alpha-Farnesene, is a sweet, bergamot, and citrus tasting flavouring ingredient. (3E,6E)-alpha-Farnesene is a constituent of the natural coating of apples and pears and other fruit. It has been identified in gingers, cottonseeds, common oregano, sweet oranges, spearmints, guava, pomes, and pears. This could make (3E,6E)-alpha-farnesene a potential biomarker for the consumption of these foods.

Structure

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

HMDB0036065
     RDKit          3D
alpha-Farnesene
 39 38  0  0  0  0  0  0  0  0999 V2000
   -6.0121    1.4697   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7869    1.7736   -0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7538    0.7392   -0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0994   -0.6511   -0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143    1.0142   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3905    0.0487   -1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3547    0.4969   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0769   -0.2396    0.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4571   -1.5539    1.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1446    0.2936    1.6490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804   -0.5739    1.6379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9639   -0.6763    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007   -0.2741   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990   -0.4139   -1.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080    0.2942    1.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7994    2.2464   -0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3706    0.4877   -0.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5638    2.7919   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7864   -0.5614    0.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2486   -1.2351    0.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6816   -1.1517   -1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3532    2.0757   -1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6928   -0.9802   -1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9269    0.1726   -2.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0738    1.4926   -0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5266   -2.1248    0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343   -2.1887    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4198   -1.6284    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342    0.4071    2.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4616    1.3028    1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690   -1.5720    2.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1139   -0.0902    2.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143   -1.1042   -0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044   -0.3396   -2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1769   -1.4248   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4848    0.3190   -1.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5028    1.1863    1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0959   -0.4373    1.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991    0.6088    0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  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
  6 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END


  Mrv1652309272007302D          

 15 14  0  0  0  0            999 V2000
 9998.0454 9998.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7603 9997.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.4735 9998.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.1888 9997.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9042 9998.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6174 9997.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.3328 9998.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9042 9999.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3309 9997.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6141 9998.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8996 9997.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1850 9998.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4705 9997.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1850 9999.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0454 9999.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  9  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036065

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC\C(C)=C\C\C=C(/C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9-10,12H,1,7-8,11H2,2-5H3/b14-10+,15-12+

> <INCHI_KEY>
CXENHBSYCFFKJS-VDQVFBMKSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.857514706649745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
5.138880741333333

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
73.2541

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.19e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
farnesene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036065
     RDKit          3D
alpha-Farnesene
 39 38  0  0  0  0  0  0  0  0999 V2000
   -6.0121    1.4697   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7869    1.7736   -0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7538    0.7392   -0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0994   -0.6511   -0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143    1.0142   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3905    0.0487   -1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3547    0.4969   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0769   -0.2396    0.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4571   -1.5539    1.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1446    0.2936    1.6490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804   -0.5739    1.6379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9639   -0.6763    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007   -0.2741   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990   -0.4139   -1.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080    0.2942    1.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7994    2.2464   -0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3706    0.4877   -0.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5638    2.7919   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7864   -0.5614    0.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2486   -1.2351    0.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6816   -1.1517   -1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3532    2.0757   -1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6928   -0.9802   -1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9269    0.1726   -2.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0738    1.4926   -0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5266   -2.1248    0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343   -2.1887    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4198   -1.6284    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342    0.4071    2.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4616    1.3028    1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690   -1.5720    2.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1139   -0.0902    2.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143   -1.1042   -0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044   -0.3396   -2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1769   -1.4248   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4848    0.3190   -1.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5028    1.1863    1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0959   -0.4373    1.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991    0.6088    0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  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
  6 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 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    8663.0188663.297   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.3528662.529   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.6848663.297   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8667.0198662.529   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8668.3558663.297   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8669.6868662.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8671.0218663.297   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.3558664.837   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.6848662.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8660.3468663.297   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8659.0138662.529   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8657.6798663.297   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8656.3458662.529   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8657.6798664.837   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.0188664.837   0.000  0.00  0.00           C+0
CONECT    1    2    9   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    1                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0036065
HETATM    1  C1  UNL     1      -6.012   1.470  -0.319  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.787   1.774  -0.676  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.754   0.739  -0.711  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.099  -0.651  -0.329  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.514   1.014  -1.070  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.391   0.049  -1.143  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.355   0.497  -0.233  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.077  -0.240   0.758  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.457  -1.554   1.006  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.145   0.294   1.649  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.380  -0.574   1.638  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.964  -0.676   0.273  1.00  0.00           C  
HETATM   13  C13 UNL     1       4.201  -0.274  -0.001  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.699  -0.414  -1.389  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.008   0.294   1.114  1.00  0.00           C  
HETATM   16  H1  UNL     1      -6.799   2.246  -0.289  1.00  0.00           H  
HETATM   17  H2  UNL     1      -6.371   0.488  -0.035  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.564   2.792  -0.939  1.00  0.00           H  
HETATM   19  H4  UNL     1      -4.786  -0.561   0.560  1.00  0.00           H  
HETATM   20  H5  UNL     1      -3.249  -1.235   0.042  1.00  0.00           H  
HETATM   21  H6  UNL     1      -4.682  -1.152  -1.126  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.353   2.076  -1.330  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.693  -0.980  -1.127  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.927   0.173  -2.186  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.074   1.493  -0.394  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.527  -2.125   0.057  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.234  -2.189   1.646  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.420  -1.628   1.511  1.00  0.00           H  
HETATM   29  H14 UNL     1       0.734   0.407   2.659  1.00  0.00           H  
HETATM   30  H15 UNL     1       1.462   1.303   1.315  1.00  0.00           H  
HETATM   31  H16 UNL     1       2.169  -1.572   2.046  1.00  0.00           H  
HETATM   32  H17 UNL     1       3.114  -0.090   2.316  1.00  0.00           H  
HETATM   33  H18 UNL     1       2.314  -1.104  -0.500  1.00  0.00           H  
HETATM   34  H19 UNL     1       3.904  -0.340  -2.143  1.00  0.00           H  
HETATM   35  H20 UNL     1       5.177  -1.425  -1.528  1.00  0.00           H  
HETATM   36  H21 UNL     1       5.485   0.319  -1.645  1.00  0.00           H  
HETATM   37  H22 UNL     1       4.503   1.186   1.516  1.00  0.00           H  
HETATM   38  H23 UNL     1       5.096  -0.437   1.959  1.00  0.00           H  
HETATM   39  H24 UNL     1       5.999   0.609   0.744  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3   18
CONECT    3    4    5    5
CONECT    4   19   20   21
CONECT    5    6   22
CONECT    6    7   23   24
CONECT    7    8    8   25
CONECT    8    9   10
CONECT    9   26   27   28
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   13   33
CONECT   13   14   15
CONECT   14   34   35   36
CONECT   15   37   38   39
END

HMDB0036065
     RDKit          3D
alpha-Farnesene
 39 38  0  0  0  0  0  0  0  0999 V2000
   -6.0121    1.4697   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7869    1.7736   -0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7538    0.7392   -0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0994   -0.6511   -0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143    1.0142   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3905    0.0487   -1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3547    0.4969   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0769   -0.2396    0.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4571   -1.5539    1.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1446    0.2936    1.6490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804   -0.5739    1.6379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9639   -0.6763    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007   -0.2741   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990   -0.4139   -1.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080    0.2942    1.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7994    2.2464   -0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3706    0.4877   -0.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5638    2.7919   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7864   -0.5614    0.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2486   -1.2351    0.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6816   -1.1517   -1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3532    2.0757   -1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6928   -0.9802   -1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9269    0.1726   -2.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0738    1.4926   -0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5266   -2.1248    0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343   -2.1887    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4198   -1.6284    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342    0.4071    2.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4616    1.3028    1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690   -1.5720    2.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1139   -0.0902    2.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143   -1.1042   -0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044   -0.3396   -2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1769   -1.4248   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4848    0.3190   -1.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5028    1.1863    1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0959   -0.4373    1.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991    0.6088    0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  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
  6 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 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
(3E,6E)-alpha-Farnesene	ChEBI
(3E,6E)-a-Farnesene	Generator
(3E,6E)-Α-farnesene	Generator
a-Farnesene	Generator
Α-farnesene	Generator
(E,E)-Farnesene	HMDB
trans-Farnesene	HMDB
3,7,11-Trimethyl-(E,E)-1,3,6,10-dodecatetraene	HMDB
alpha-trans,trans-Farnesene	HMDB
trans,trans-alpha-Farnesene	HMDB
alpha-Farnesene	MeSH
(3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraene	HMDB
(E,E)-alpha-Farnesene	HMDB
(E,E)-α-Farnesene	HMDB
3,7,11-Trimethyl-1,3,6,10-dodecatetraene	HMDB
Farnesene	HMDB
trans,trans-α-Farnesene	HMDB
trans-2,6,10-Trimethyl-2,6,9,11-dodecatetraene	HMDB
trans-3,7,11-Trimethyl-1,3,6,10-dodecatetraene	HMDB
trans-alpha-Farnesene	HMDB
trans-α-Farnesene	HMDB

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.3511

Monoisotopic Molecular Weight

204.187800768

IUPAC Name

(3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene

Traditional Name

farnesene

CAS Registry Number

502-61-4

SMILES

CC(C)=CCC\C(C)=C\C\C=C(/C)C=C

InChI Identifier

InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9-10,12H,1,7-8,11H2,2-5H3/b14-10+,15-12+

InChI Key

CXENHBSYCFFKJS-VDQVFBMKSA-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

Farsesane sesquiterpenoid
Sesquiterpenoid
Alkatetraene
Branched unsaturated hydrocarbon
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Acyclic olefin
Hydrocarbon
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha-farnesene (CHEBI:10280 )
Farnesenes (C09665 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Feces (PMID: 17314143)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036065)

Source

Exogenous

Food

Food (HMDB: HMDB0036065)

Fruit

Pome

Apple (FooDB: FOOD00105)
Asian pear (FooDB: FOOD00291)

Other fruit

Fig (FooDB: FOOD00081)

Herb and spice

Spice

Ginger (FooDB: FOOD00206)
Nutmeg (FooDB: FOOD00118)

Herb

Exogenous (HMDB: HMDB0036065)

Endogenous

Plant

Plant (HMDB: HMDB0036065)

Animal

Animal (HMDB: HMDB0036065)

Endogenous (HMDB: HMDB0036065)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036065)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036065)

Lipid metabolism pathway (HMDB: HMDB0036065)

Cellular process

Cell signaling (HMDB: HMDB0036065)

Biochemical process

Lipid transport (HMDB: HMDB0036065)

Role

Biological role

Energy source (HMDB: HMDB0036065)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036065)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	260.00 to 262.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.011 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.139 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0052 g/L	ALOGPS
logP	5.7	ALOGPS
logP	5.14	ChemAxon
logS	-4.6	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	73.25 m³·mol⁻¹	ChemAxon
Polarizability	26.86 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	154.307	31661259
DarkChem	[M-H]-	154.147	31661259
DeepCCS	[M+H]+	153.566	30932474
DeepCCS	[M-H]-	151.208	30932474
DeepCCS	[M-2H]-	184.946	30932474
DeepCCS	[M+Na]+	159.812	30932474
AllCCS	[M+H]+	152.8	32859911
AllCCS	[M+H-H2O]+	149.1	32859911
AllCCS	[M+NH4]+	156.3	32859911
AllCCS	[M+Na]+	157.3	32859911
AllCCS	[M-H]-	151.2	32859911
AllCCS	[M+Na-2H]-	152.1	32859911
AllCCS	[M+HCOO]-	153.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.97 minutes	32390414
Predicted by Siyang on May 30, 2022	21.8421 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.16 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	31.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3009.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	742.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	287.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	496.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	160.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	773.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	875.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	84.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1864.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	712.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1275.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	698.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	517.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	379.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	670.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Farnesene	CC(C)=CCC\C(C)=C\C\C=C(/C)C=C	1757.0	Standard polar	33892256
alpha-Farnesene	CC(C)=CCC\C(C)=C\C\C=C(/C)C=C	1488.9	Standard non polar	33892256
alpha-Farnesene	CC(C)=CCC\C(C)=C\C\C=C(/C)C=C	1514.6	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-Farnesene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0673-9800000000-2417bd57042b291e594e	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Farnesene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Farnesene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9300000000-3317cba9629f9379052f	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Farnesene 10V, Positive-QTOF	splash10-0a4i-3690000000-313b913d532cd4decec1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Farnesene 20V, Positive-QTOF	splash10-0pw9-9710000000-078e5a8d7e85822b7c0c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Farnesene 40V, Positive-QTOF	splash10-0uxr-9100000000-3d3f85f913cafb612d5c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Farnesene 10V, Negative-QTOF	splash10-0udi-0090000000-6d4cdcd69849df029e45	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Farnesene 20V, Negative-QTOF	splash10-0udi-0190000000-e363a25bab51e774a592	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Farnesene 40V, Negative-QTOF	splash10-0kg9-4900000000-b4cda282a594b52f2539	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Farnesene 10V, Negative-QTOF	splash10-0udi-0190000000-fa0c676eabe0c49e322b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Farnesene 20V, Negative-QTOF	splash10-0udi-0390000000-0d353a60a5a97cd9c1a3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Farnesene 40V, Negative-QTOF	splash10-014i-4900000000-9f5bab6c0c653c72230e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Farnesene 10V, Positive-QTOF	splash10-060s-7910000000-05be940f3488abb12fe8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Farnesene 20V, Positive-QTOF	splash10-0a7l-9300000000-a54209dd2c1271d1d7d7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Farnesene 40V, Positive-QTOF	splash10-05ru-9000000000-a7b8e3b259690a16a441	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details

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

Farnesene

METLIN ID

Not Available

PubChem Compound

5281516

PDB ID

Not Available

ChEBI ID

10280

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1044061

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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.

Showing metabocard for alpha-Farnesene (HMDB0036065)

MOL for HMDB0036065 (alpha-Farnesene)

3D MOL for HMDB0036065 (alpha-Farnesene)

3D SDF for HMDB0036065 (alpha-Farnesene)

3D-SDF for HMDB0036065 (alpha-Farnesene)

PDB for HMDB0036065 (alpha-Farnesene)

3D PDB for HMDB0036065 (alpha-Farnesene)

SMILES for HMDB0036065 (alpha-Farnesene)

INCHI for HMDB0036065 (alpha-Farnesene)

Structure for HMDB0036065 (alpha-Farnesene)

3D Structure for HMDB0036065 (alpha-Farnesene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra