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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 05:56:49 UTC

Update Date

2021-09-24 05:56:49 UTC

HMDB ID

HMDB0303953

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2-trans-6-trans)-farnesoate

Description

(2-trans-6-trans)-farnesoate, also known as (2e,6e)-farnesoic acid or trans,trans-farnesoic acid, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units (2-trans-6-trans)-farnesoate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (2-trans-6-trans)-farnesoate can be found in a number of food items such as chinese water chestnut, wasabi, adzuki bean, and garden onion (variety), which makes (2-trans-6-trans)-farnesoate a potential biomarker for the consumption of these food products.

Structure

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

HMDB0303953
     RDKit          3D
(2-trans-6-trans)-farnesoate
 40 39  0  0  0  0  0  0  0  0999 V2000
   -4.7622    1.3917    0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8298   -0.0760    0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1877   -0.6671    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7339   -0.8083    0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734   -0.2392    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6383   -0.5079   -0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2508    0.0525   -0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0913    1.4888   -0.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7561   -0.7916   -0.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1448   -0.2685   -0.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8923   -0.9441    0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2640   -0.3986    0.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1919   -0.5234   -0.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5994    0.2016    1.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9075    0.7741    1.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1980    1.3312    2.8887 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8460    0.7091    0.8094 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.7616    1.8152    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3815    1.9217   -0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0636    1.6229    1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6160   -0.2741   -0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7795   -0.3907    1.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0872   -1.7808    0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154   -1.8697    0.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3578    0.8182    0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8574   -0.7845    1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1963    0.0076   -1.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6505   -1.5780   -1.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    1.6289    0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0646    2.0070   -0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5911    1.9925   -1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5571   -1.8357   -1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1860    0.8201   -0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6586   -0.5785   -1.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3430   -0.8623    1.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9001   -2.0341    0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1040   -1.1160   -0.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4825    0.4758   -1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6357   -1.0050   -1.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8816    0.2752    2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
M  CHG  1  17  -1
M  END


  Mrv1533007131514022D          

 19 18  0  0  0  0            999 V2000
   -5.3625   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9500   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  6  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  7  2  0  0  0  0
 13  3  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14  4  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  2  0  0  0  0
 15 11  1  0  0  0  0
 16 15  2  0  0  0  0
 17 15  1  0  0  0  0
 18  9  1  0  0  0  0
 19 11  1  0  0  0  0
M  CHG  1  17  -1
M  END
> <DATABASE_ID>
HMDB0303953

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CC\C(C)=C(/[H])C([O-])=O)=C(\C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-12(2)7-5-8-13(3)9-6-10-14(4)11-15(16)17/h7,9,11H,5-6,8,10H2,1-4H3,(H,16,17)/p-1/b13-9+,14-11+

> <INCHI_KEY>
WJHFZYAELPOJIV-IJFRVEDASA-M

> <FORMULA>
C15H23O2

> <MOLECULAR_WEIGHT>
235.348

> <EXACT_MASS>
235.170353561

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.298321994780522

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoate

> <ALOGPS_LOGP>
4.99

> <JCHEM_LOGP>
4.482372109

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.12157483965426

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
85.6892

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303953
     RDKit          3D
(2-trans-6-trans)-farnesoate
 40 39  0  0  0  0  0  0  0  0999 V2000
   -4.7622    1.3917    0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8298   -0.0760    0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1877   -0.6671    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7339   -0.8083    0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734   -0.2392    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6383   -0.5079   -0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2508    0.0525   -0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0913    1.4888   -0.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7561   -0.7916   -0.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1448   -0.2685   -0.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8923   -0.9441    0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2640   -0.3986    0.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1919   -0.5234   -0.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5994    0.2016    1.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9075    0.7741    1.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1980    1.3312    2.8887 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8460    0.7091    0.8094 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.7616    1.8152    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3815    1.9217   -0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0636    1.6229    1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6160   -0.2741   -0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7795   -0.3907    1.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0872   -1.7808    0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154   -1.8697    0.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3578    0.8182    0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8574   -0.7845    1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1963    0.0076   -1.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6505   -1.5780   -1.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    1.6289    0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0646    2.0070   -0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5911    1.9925   -1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5571   -1.8357   -1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1860    0.8201   -0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6586   -0.5785   -1.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3430   -0.8623    1.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9001   -2.0341    0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1040   -1.1160   -0.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4825    0.4758   -1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6357   -1.0050   -1.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8816    0.2752    2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
M  CHG  1  17  -1
M  END

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0     -10.010  -6.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.010  -4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.390  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.930  -4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.700  -5.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.390  -4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.240  -5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.620  -2.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O-1
HETATM   18  H   UNK     0      -2.310  -4.001   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.310  -1.334   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5    7    8                                                       
CONECT    6    9   10                                                       
CONECT    7    5   12                                                       
CONECT    8    5   13                                                       
CONECT    9    6   13   18                                                  
CONECT   10    6   14                                                       
CONECT   11   14   15   19                                                  
CONECT   12    1    2    7                                                  
CONECT   13    3    8    9                                                  
CONECT   14    4   10   11                                                  
CONECT   15   11   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    9                                                            
CONECT   19   11                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0303953
HETATM    1  C1  UNL     1      -4.762   1.392   0.699  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.830  -0.076   0.427  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.188  -0.667   0.267  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.734  -0.808   0.335  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.373  -0.239   0.490  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.638  -0.508  -0.820  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.251   0.052  -0.710  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.091   1.489  -0.462  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.756  -0.792  -0.843  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.145  -0.269  -0.739  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.892  -0.944   0.408  1.00  0.00           C  
HETATM   12  C12 UNL     1       4.264  -0.399   0.481  1.00  0.00           C  
HETATM   13  C13 UNL     1       5.192  -0.523  -0.647  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.599   0.202   1.618  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.908   0.774   1.813  1.00  0.00           C  
HETATM   16  O1  UNL     1       6.198   1.331   2.889  1.00  0.00           O  
HETATM   17  O2  UNL     1       6.846   0.709   0.809  1.00  0.00           O1-
HETATM   18  H1  UNL     1      -5.762   1.815   0.923  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.381   1.922  -0.199  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.064   1.623   1.528  1.00  0.00           H  
HETATM   21  H4  UNL     1      -6.616  -0.274  -0.677  1.00  0.00           H  
HETATM   22  H5  UNL     1      -6.779  -0.391   1.157  1.00  0.00           H  
HETATM   23  H6  UNL     1      -6.087  -1.781   0.210  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.815  -1.870   0.137  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.358   0.818   0.758  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.857  -0.784   1.331  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.196   0.008  -1.622  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.650  -1.578  -1.032  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.359   1.629   0.555  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.065   2.007  -0.555  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.591   1.992  -1.175  1.00  0.00           H  
HETATM   32  H15 UNL     1       0.557  -1.836  -1.024  1.00  0.00           H  
HETATM   33  H16 UNL     1       2.186   0.820  -0.691  1.00  0.00           H  
HETATM   34  H17 UNL     1       2.659  -0.578  -1.672  1.00  0.00           H  
HETATM   35  H18 UNL     1       2.343  -0.862   1.353  1.00  0.00           H  
HETATM   36  H19 UNL     1       2.900  -2.034   0.143  1.00  0.00           H  
HETATM   37  H20 UNL     1       6.104  -1.116  -0.422  1.00  0.00           H  
HETATM   38  H21 UNL     1       5.482   0.476  -1.063  1.00  0.00           H  
HETATM   39  H22 UNL     1       4.636  -1.005  -1.502  1.00  0.00           H  
HETATM   40  H23 UNL     1       3.882   0.275   2.442  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4    4
CONECT    3   21   22   23
CONECT    4    5   24
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8    9    9
CONECT    8   29   30   31
CONECT    9   10   32
CONECT   10   11   33   34
CONECT   11   12   35   36
CONECT   12   13   14   14
CONECT   13   37   38   39
CONECT   14   15   40
CONECT   15   16   16   17
END

HMDB0303953
     RDKit          3D
(2-trans-6-trans)-farnesoate
 40 39  0  0  0  0  0  0  0  0999 V2000
   -4.7622    1.3917    0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8298   -0.0760    0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1877   -0.6671    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7339   -0.8083    0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734   -0.2392    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6383   -0.5079   -0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2508    0.0525   -0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0913    1.4888   -0.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7561   -0.7916   -0.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1448   -0.2685   -0.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8923   -0.9441    0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2640   -0.3986    0.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1919   -0.5234   -0.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5994    0.2016    1.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9075    0.7741    1.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1980    1.3312    2.8887 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8460    0.7091    0.8094 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.7616    1.8152    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3815    1.9217   -0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0636    1.6229    1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6160   -0.2741   -0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7795   -0.3907    1.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0872   -1.7808    0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154   -1.8697    0.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3578    0.8182    0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8574   -0.7845    1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1963    0.0076   -1.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6505   -1.5780   -1.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    1.6289    0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0646    2.0070   -0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5911    1.9925   -1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5571   -1.8357   -1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1860    0.8201   -0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6586   -0.5785   -1.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3430   -0.8623    1.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9001   -2.0341    0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1040   -1.1160   -0.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4825    0.4758   -1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6357   -1.0050   -1.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8816    0.2752    2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
M  CHG  1  17  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E,6E)-Farnesoic acid	Generator
(2-trans-6-trans)-Farnesoate	MetaCyc
(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrienoic acid	MetaCyc
(2E,6E)-Farnesenic acid	MetaCyc
(2E,6E)-Farnesic acid	MetaCyc
(2E,6E)-Farnesylic acid	MetaCyc
(2E,6E)-3,7,11-Trimethyl-dodeca-2,6,10-trienoic acid	MetaCyc
trans,trans-Farnesoic acid	MetaCyc
(e,e)-Farnesoic acid	MetaCyc
all-trans-Farnesoic acid	MetaCyc
(2-trans-6-trans) Farnesoic acid	MetaCyc
(2-trans-6-trans)-Farnesoic acid	Generator
(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrienoate	Generator
(2E,6E)-Farnesenate	Generator
(2E,6E)-Farnesate	Generator
(2E,6E)-Farnesylate	Generator
(2E,6E)-3,7,11-Trimethyl-dodeca-2,6,10-trienoate	Generator
trans,trans-Farnesoate	Generator
(e,e)-Farnesoate	Generator
all-trans-Farnesoate	Generator
(2-trans-6-trans) Farnesoate	Generator

Chemical Formula

C₁₅H₂₃O₂

Average Molecular Weight

235.348

Monoisotopic Molecular Weight

235.170353561

IUPAC Name

(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoate

Traditional Name

(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoate

CAS Registry Number

Not Available

SMILES

[H]\C(CC\C(C)=C(/[H])C([O-])=O)=C(\C)CCC=C(C)C

InChI Identifier

InChI=1S/C15H24O2/c1-12(2)7-5-8-13(3)9-6-10-14(4)11-15(16)17/h7,9,11H,5-6,8,10H2,1-4H3,(H,16,17)/p-1/b13-9+,14-11+

InChI Key

WJHFZYAELPOJIV-IJFRVEDASA-M

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
Farsesane sesquiterpenoid
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

polyunsaturated fatty acid anion (CHEBI:83276 )
methyl-branched fatty acid anion (CHEBI:83276 )

Ontology

Not Available

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

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	4.99	ALOGPS
logP	4.48	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	5.12	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	85.69 m³·mol⁻¹	ChemAxon
Polarizability	28.3 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	162.088	32859911
AllCCS	[M+H-H2O]+	158.557	32859911
AllCCS	[M+Na]+	166.313	32859911
AllCCS	[M+NH4]+	165.369	32859911
AllCCS	[M-H]-	159.595	32859911
AllCCS	[M+Na-2H]-	160.482	32859911
AllCCS	[M+HCOO]-	161.578	32859911
DeepCCS	[M+H]+	167.015	30932474
DeepCCS	[M-H]-	164.657	30932474
DeepCCS	[M-2H]-	198.119	30932474
DeepCCS	[M+Na]+	173.316	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-trans-6-trans)-farnesoate 10V, Negative-QTOF	splash10-000f-0970000000-448d8f7e33890672f2dc	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-trans-6-trans)-farnesoate 20V, Negative-QTOF	splash10-0006-0950000000-1eac6610fd7ca0af0fd3	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-trans-6-trans)-farnesoate 40V, Negative-QTOF	splash10-00bc-1920000000-006da47fc416f84171a0	2019-02-23	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

FDB030091

KNApSAcK ID

Not Available

Chemspider ID

10644732

KEGG Compound ID

Not Available

BioCyc ID

CPD-12585

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21895630

PDB ID

Not Available

ChEBI ID

83276

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

Not Available

Showing metabocard for (2-trans-6-trans)-farnesoate (HMDB0303953)

MOL for HMDB0303953 ((2-trans-6-trans)-farnesoate)

3D MOL for HMDB0303953 ((2-trans-6-trans)-farnesoate)

3D SDF for HMDB0303953 ((2-trans-6-trans)-farnesoate)

3D-SDF for HMDB0303953 ((2-trans-6-trans)-farnesoate)

PDB for HMDB0303953 ((2-trans-6-trans)-farnesoate)

3D PDB for HMDB0303953 ((2-trans-6-trans)-farnesoate)

SMILES for HMDB0303953 ((2-trans-6-trans)-farnesoate)

INCHI for HMDB0303953 ((2-trans-6-trans)-farnesoate)

Structure for HMDB0303953 ((2-trans-6-trans)-farnesoate)

3D Structure for HMDB0303953 ((2-trans-6-trans)-farnesoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra