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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:57:17 UTC

Update Date

2021-09-26 23:04:35 UTC

HMDB ID

HMDB0252169

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,7,11-Trimethyldodeca-2,6,10-trienoic acid

Description

farnesoic acid, also known as farnesoate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on farnesoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3,7,11-trimethyldodeca-2,6,10-trienoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3,7,11-Trimethyldodeca-2,6,10-trienoic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0252169
     RDKit          3D
3,7,11-Trimethyldodeca-2,6,10-trienoic acid
 41 40  0  0  0  0  0  0  0  0999 V2000
   -4.9593   -0.0160    1.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858   -0.2441   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2765   -0.3607   -1.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0842   -0.3470   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036   -0.2290    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678    0.9428    0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2983    1.0256   -0.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018    1.2047   -1.7794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9994    0.9914   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6818    0.8690    1.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4155   -0.4054    1.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4793   -0.6782    0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1854   -0.9513   -1.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7343   -0.7289    0.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8897   -0.9809   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7493   -1.1657   -1.2466 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1465   -1.0139    0.5627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7155   -0.8637    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5871    0.9076    1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0646    0.1008    1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1194    0.3576   -1.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6103   -1.4153   -1.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7361   -0.1587   -2.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6607   -0.5396   -1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6558   -1.1914    0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8373   -0.1086    1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    0.9310    1.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9681    1.8547    0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6358    0.2641   -2.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1452    2.0283   -2.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125    1.5972   -1.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5950    1.0932   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0347    1.1253    1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5234    1.6739    1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8508   -0.3038    2.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7332   -1.2836    1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6386   -1.9437   -1.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0783   -1.1445   -1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4819   -0.1919   -1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8940   -0.5628    1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5256   -0.1385    0.9049 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  3
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  3
 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
 17 41  1  0
M  END

Farnesoic acid
  Mrv1572001071617252D          

 17 16  0  0  0  0            999 V2000
   -4.6207    1.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4773    1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7628    1.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3806    1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0950    1.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9529    1.4692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2385    1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2385    2.7067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9062    1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9062    2.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8095    1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8095    2.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484    1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484    2.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5240    1.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3339    1.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1918    1.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 17  2  0  0  0  0
  9  1  1  0  0  0  0
 17  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3 13  1  0  0  0  0
 13 16  2  0  0  0  0
 16  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5 11  1  0  0  0  0
 11 15  2  0  0  0  0
 15  7  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  2  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  4  0  0  0
 13 14  1  4  0  0  0
M  END
> <DATABASE_ID>
HMDB0252169

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCCC(C)=CCCC(C)=CC(O)=O

> <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)

> <INCHI_KEY>
WJHFZYAELPOJIV-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.355

> <EXACT_MASS>
236.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.885549951303325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7,11-trimethyldodeca-2,6,10-trienoic acid

> <ALOGPS_LOGP>
4.68

> <JCHEM_LOGP>
4.482372109

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.12157483965426

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
74.8521

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
farnesoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0252169
     RDKit          3D
3,7,11-Trimethyldodeca-2,6,10-trienoic acid
 41 40  0  0  0  0  0  0  0  0999 V2000
   -4.9593   -0.0160    1.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858   -0.2441   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2765   -0.3607   -1.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0842   -0.3470   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036   -0.2290    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678    0.9428    0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2983    1.0256   -0.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018    1.2047   -1.7794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9994    0.9914   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6818    0.8690    1.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4155   -0.4054    1.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4793   -0.6782    0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1854   -0.9513   -1.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7343   -0.7289    0.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8897   -0.9809   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7493   -1.1657   -1.2466 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1465   -1.0139    0.5627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7155   -0.8637    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5871    0.9076    1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0646    0.1008    1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1194    0.3576   -1.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6103   -1.4153   -1.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7361   -0.1587   -2.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6607   -0.5396   -1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6558   -1.1914    0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8373   -0.1086    1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    0.9310    1.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9681    1.8547    0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6358    0.2641   -2.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1452    2.0283   -2.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125    1.5972   -1.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5950    1.0932   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0347    1.1253    1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5234    1.6739    1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8508   -0.3038    2.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7332   -1.2836    1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6386   -1.9437   -1.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0783   -1.1445   -1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4819   -0.1919   -1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8940   -0.5628    1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5256   -0.1385    0.9049 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  3
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  3
 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
 17 41  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Farnesoic acid                                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      -8.625   2.743   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.624   3.513   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.291   2.743   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.710   3.513   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.044   2.743   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.379   2.743   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.045   3.513   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.045   5.053   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -7.292   3.513   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.292   5.053   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.378   3.513   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.378   5.053   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.957   3.513   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.957   5.053   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.711   2.743   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.623   2.743   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.958   2.743   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   17    3                                                       
CONECT    3    2   13                                                       
CONECT    4   16    5                                                       
CONECT    5    4   11                                                       
CONECT    6    7                                                            
CONECT    7   15    6    8                                                  
CONECT    8    7                                                            
CONECT    9   17    1   10                                                  
CONECT   10    9                                                            
CONECT   11    5   15   12                                                  
CONECT   12   11                                                            
CONECT   13    3   16   14                                                  
CONECT   14   13                                                            
CONECT   15   11    7                                                       
CONECT   16   13    4                                                       
CONECT   17    9    2                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0252170
HETATM    1  C1  UNL     1      -3.373   4.111  -0.256  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.336   2.646  -0.076  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.594   1.921   0.207  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.208   1.961  -0.160  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.131   0.491   0.014  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.203   0.207   1.202  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.064  -1.224   1.454  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.320  -2.007   1.792  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.078  -1.860   1.406  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.404  -1.289   1.100  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.943  -1.998  -0.133  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.308  -1.483  -0.509  1.00  0.00           C  
HETATM   13  C13 UNL     1       4.013  -2.041  -1.696  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.904  -0.544   0.190  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.210  -0.042  -0.159  1.00  0.00           C  
HETATM   16  O1  UNL     1       5.861  -0.464  -1.142  1.00  0.00           O  
HETATM   17  O2  UNL     1       5.813   0.970   0.617  1.00  0.00           O  
HETATM   18  H1  UNL     1      -2.655   4.466  -1.024  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.411   4.410  -0.473  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.113   4.592   0.733  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.794   1.285  -0.705  1.00  0.00           H  
HETATM   22  H5  UNL     1      -5.425   2.628   0.363  1.00  0.00           H  
HETATM   23  H6  UNL     1      -4.471   1.282   1.114  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.283   2.484  -0.366  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.581   0.081  -0.875  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.111   0.011   0.144  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.265   0.724   1.028  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.686   0.745   2.064  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.318  -2.323   2.841  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.226  -1.394   1.618  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.370  -2.859   1.073  1.00  0.00           H  
HETATM   32  H15 UNL     1       0.043  -2.956   1.621  1.00  0.00           H  
HETATM   33  H16 UNL     1       1.424  -0.216   0.911  1.00  0.00           H  
HETATM   34  H17 UNL     1       2.092  -1.515   1.941  1.00  0.00           H  
HETATM   35  H18 UNL     1       2.047  -3.081   0.037  1.00  0.00           H  
HETATM   36  H19 UNL     1       1.271  -1.740  -0.978  1.00  0.00           H  
HETATM   37  H20 UNL     1       4.950  -2.564  -1.425  1.00  0.00           H  
HETATM   38  H21 UNL     1       3.356  -2.832  -2.130  1.00  0.00           H  
HETATM   39  H22 UNL     1       4.148  -1.250  -2.472  1.00  0.00           H  
HETATM   40  H23 UNL     1       3.418  -0.125   1.058  1.00  0.00           H  
HETATM   41  H24 UNL     1       6.651   0.791   1.167  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
CONECT   17   41
END

HMDB0252169
     RDKit          3D
3,7,11-Trimethyldodeca-2,6,10-trienoic acid
 41 40  0  0  0  0  0  0  0  0999 V2000
   -4.9593   -0.0160    1.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858   -0.2441   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2765   -0.3607   -1.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0842   -0.3470   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036   -0.2290    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678    0.9428    0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2983    1.0256   -0.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018    1.2047   -1.7794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9994    0.9914   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6818    0.8690    1.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4155   -0.4054    1.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4793   -0.6782    0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1854   -0.9513   -1.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7343   -0.7289    0.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8897   -0.9809   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7493   -1.1657   -1.2466 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1465   -1.0139    0.5627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7155   -0.8637    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5871    0.9076    1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0646    0.1008    1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1194    0.3576   -1.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6103   -1.4153   -1.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7361   -0.1587   -2.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6607   -0.5396   -1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6558   -1.1914    0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8373   -0.1086    1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    0.9310    1.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9681    1.8547    0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6358    0.2641   -2.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1452    2.0283   -2.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125    1.5972   -1.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5950    1.0932   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0347    1.1253    1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5234    1.6739    1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8508   -0.3038    2.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7332   -1.2836    1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6386   -1.9437   -1.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0783   -1.1445   -1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4819   -0.1919   -1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8940   -0.5628    1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5256   -0.1385    0.9049 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  3
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  3
 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
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Farnesoate	Generator
3,7,11-Trimethyl-2,6,10-dodecatrienoic acid	MeSH
Farnesenic acid	MeSH

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.355

Monoisotopic Molecular Weight

236.177630013

IUPAC Name

3,7,11-trimethyldodeca-2,6,10-trienoic acid

Traditional Name

farnesoic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(C)=CCCC(C)=CC(O)=O

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)

InChI Key

WJHFZYAELPOJIV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
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
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha,beta-unsaturated monocarboxylic acid (CHEBI:36969 )
trienoic fatty acid (CHEBI:36969 )
methyl-branched fatty acid (CHEBI:36969 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	4.68	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	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.85 m³·mol⁻¹	ChemAxon
Polarizability	28.89 Å³	ChemAxon
Number of Rings	0	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
DeepCCS	[M+H]+	151.723	30932474
DeepCCS	[M-H]-	148.413	30932474
DeepCCS	[M-2H]-	185.187	30932474
DeepCCS	[M+Na]+	160.725	30932474
AllCCS	[M+H]+	161.8	32859911
AllCCS	[M+H-H2O]+	158.3	32859911
AllCCS	[M+NH4]+	165.1	32859911
AllCCS	[M+Na]+	166.0	32859911
AllCCS	[M-H]-	160.4	32859911
AllCCS	[M+Na-2H]-	161.3	32859911
AllCCS	[M+HCOO]-	162.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	17.4744 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.22 minutes	32390414

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,7,11-Trimethyldodeca-2,6,10-trienoic acid,1TMS,isomer #1	CC(C)=CCCC(C)=CCCC(C)=CC(=O)O[Si](C)(C)C	1885.8	Semi standard non polar	33892256
3,7,11-Trimethyldodeca-2,6,10-trienoic acid,1TMS,isomer #1	CC(C)=CCCC(C)=CCCC(C)=CC(=O)O[Si](C)(C)C	1909.2	Standard non polar	33892256
3,7,11-Trimethyldodeca-2,6,10-trienoic acid,1TMS,isomer #1	CC(C)=CCCC(C)=CCCC(C)=CC(=O)O[Si](C)(C)C	2042.9	Standard polar	33892256
3,7,11-Trimethyldodeca-2,6,10-trienoic acid,1TBDMS,isomer #1	CC(C)=CCCC(C)=CCCC(C)=CC(=O)O[Si](C)(C)C(C)(C)C	2093.7	Semi standard non polar	33892256
3,7,11-Trimethyldodeca-2,6,10-trienoic acid,1TBDMS,isomer #1	CC(C)=CCCC(C)=CCCC(C)=CC(=O)O[Si](C)(C)C(C)(C)C	2133.0	Standard non polar	33892256
3,7,11-Trimethyldodeca-2,6,10-trienoic acid,1TBDMS,isomer #1	CC(C)=CCCC(C)=CCCC(C)=CC(=O)O[Si](C)(C)C(C)(C)C	2166.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-05vp-8920000000-85dfdc016dda80773122	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid 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 - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid 10V, Positive-QTOF	splash10-00n0-0980000000-4a07c7ca583a95256fb8	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid 20V, Positive-QTOF	splash10-004l-2900000000-ad4a580e28fe474e78af	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid 40V, Positive-QTOF	splash10-0ldi-9600000000-146a0f1513f1d54dfb5c	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid 10V, Negative-QTOF	splash10-000l-0590000000-e8f40d325d3773f970ec	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid 20V, Negative-QTOF	splash10-000f-1970000000-a01a05b746c7e61d0ca6	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid 40V, Negative-QTOF	splash10-05xu-5920000000-6fafb70686f70d2fa205	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid 10V, Positive-QTOF	splash10-00li-3940000000-ad36304a23d967a90853	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid 20V, Positive-QTOF	splash10-0a4i-6900000000-3fbbedad29accf33cdea	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid 40V, Positive-QTOF	splash10-0apl-9300000000-fbb8ec168d687fa75aa3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid 10V, Negative-QTOF	splash10-000i-0090000000-637c4fd38c6be73b0739	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid 20V, Negative-QTOF	splash10-000i-0980000000-4a06c889bf0dac8739b9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7,11-Trimethyldodeca-2,6,10-trienoic acid 40V, Negative-QTOF	splash10-00os-3900000000-ffa7583bd22a0d5977c1	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

84003

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

93051

PDB ID

Not Available

ChEBI ID

36969

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1435221

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 3,7,11-Trimethyldodeca-2,6,10-trienoic acid (HMDB0252169)

MOL for HMDB0252169 (3,7,11-Trimethyldodeca-2,6,10-trienoic acid)

3D MOL for HMDB0252169 (3,7,11-Trimethyldodeca-2,6,10-trienoic acid)

3D SDF for HMDB0252169 (3,7,11-Trimethyldodeca-2,6,10-trienoic acid)

3D-SDF for HMDB0252169 (3,7,11-Trimethyldodeca-2,6,10-trienoic acid)

PDB for HMDB0252169 (3,7,11-Trimethyldodeca-2,6,10-trienoic acid)

3D PDB for HMDB0252169 (3,7,11-Trimethyldodeca-2,6,10-trienoic acid)

SMILES for HMDB0252169 (3,7,11-Trimethyldodeca-2,6,10-trienoic acid)

INCHI for HMDB0252169 (3,7,11-Trimethyldodeca-2,6,10-trienoic acid)

Structure for HMDB0252169 (3,7,11-Trimethyldodeca-2,6,10-trienoic acid)

3D Structure for HMDB0252169 (3,7,11-Trimethyldodeca-2,6,10-trienoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra