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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:38 UTC

Update Date

2022-03-07 02:52:44 UTC

HMDB ID

HMDB0030891

Secondary Accession Numbers

HMDB30891

Metabolite Identification

Common Name

(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one

Description

(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one 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 (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one.

Structure

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

HMDB0030891
     RDKit          3D
(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one
 41 40  0  0  0  0  0  0  0  0999 V2000
    6.6766   -0.4941    0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2997    0.0611    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0754    1.5167    0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034   -0.7953    0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9374   -0.3511    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6653    0.8608   -0.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -1.3510   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5627   -0.6501   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3515    0.1631   -1.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883   -0.7700    0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6775   -0.0710    0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8176   -1.0644    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0824   -0.3310    0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3453   -1.1103    0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0951    0.9847    0.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3827    1.7414   -0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5181    2.6052    0.9098 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4427    0.2820    0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8199   -1.2833   -0.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6029   -1.0320    1.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0628    2.0197    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6666    1.7963   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4434    1.9505    0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4854   -1.8596    0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9721   -2.0700   -0.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8510   -1.9301    0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1440    1.2417   -1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2253    0.1791   -2.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5117   -0.2203   -2.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2365   -1.3588    1.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6447    0.5033   -0.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8257    0.6310    1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6528   -1.7611   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539   -1.6805    1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9300   -0.8601   -0.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1364   -2.1972    0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9655   -0.9753    0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2034    1.5942    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2348    2.3575   -1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2371    1.0846   -0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984    2.6436    1.4730 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 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
  7 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
M  END


  Mrv0541 05061305342D          

 17 16  0  0  0  0            999 V2000
   -0.4125   -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
    4.5375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    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
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    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
    2.0625    0.7145    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
    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
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    4.2868    0.0000 O   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
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12 10  2  0  0  0  0
 13  3  1  0  0  0  0
 13  6  1  0  0  0  0
 13  8  2  0  0  0  0
 14  4  1  0  0  0  0
 14  7  2  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16  9  1  0  0  0  0
 17 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030891

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CC(=O)C\C(C)=C\CC\C(C)=C\CO

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

> <INCHI_KEY>
VCXVMWVWGVWZPY-CCLLZULESA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.45617480162493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6E,10E)-12-hydroxy-2,6,10-trimethyldodeca-2,6,10-trien-4-one

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
3.342624992

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.041616103592165

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.23621312942258

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2170474067295505

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
75.60279999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6E,10E)-12-hydroxy-2,6,10-trimethyldodeca-2,6,10-trien-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030891
     RDKit          3D
(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one
 41 40  0  0  0  0  0  0  0  0999 V2000
    6.6766   -0.4941    0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2997    0.0611    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0754    1.5167    0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034   -0.7953    0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9374   -0.3511    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6653    0.8608   -0.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -1.3510   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5627   -0.6501   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3515    0.1631   -1.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883   -0.7700    0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6775   -0.0710    0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8176   -1.0644    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0824   -0.3310    0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3453   -1.1103    0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0951    0.9847    0.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3827    1.7414   -0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5181    2.6052    0.9098 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4427    0.2820    0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8199   -1.2833   -0.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6029   -1.0320    1.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0628    2.0197    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6666    1.7963   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4434    1.9505    0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4854   -1.8596    0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9721   -2.0700   -0.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8510   -1.9301    0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1440    1.2417   -1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2253    0.1791   -2.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5117   -0.2203   -2.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2365   -1.3588    1.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6447    0.5033   -0.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8257    0.6310    1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6528   -1.7611   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539   -1.6805    1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9300   -0.8601   -0.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1364   -2.1972    0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9655   -0.9753    0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2034    1.5942    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2348    2.3575   -1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2371    1.0846   -0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984    2.6436    1.4730 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 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
  7 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.470   6.668   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.850   4.001   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       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.780   5.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.620   2.667   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      10.780   8.002   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5    6    7                                                       
CONECT    6    5   13                                                       
CONECT    7    5   14                                                       
CONECT    8    9   13                                                       
CONECT    9    8   16                                                       
CONECT   10   12   15                                                       
CONECT   11   14   15                                                       
CONECT   12    1    2   10                                                  
CONECT   13    3    6    8                                                  
CONECT   14    4    7   11                                                  
CONECT   15   10   11   17                                                  
CONECT   16    9                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0030891
HETATM    1  C1  UNL     1       6.677  -0.494   0.487  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.300   0.061   0.261  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.075   1.517   0.097  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.303  -0.795   0.214  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.937  -0.351   0.000  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.665   0.861  -0.147  1.00  0.00           O  
HETATM    7  C6  UNL     1       1.850  -1.351  -0.045  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.563  -0.650  -0.273  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.352   0.163  -1.491  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.388  -0.770   0.637  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.677  -0.071   0.413  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.818  -1.064   0.363  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.082  -0.331   0.151  1.00  0.00           C  
HETATM   14  C13 UNL     1      -5.345  -1.110   0.060  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.095   0.985   0.044  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.383   1.741  -0.173  1.00  0.00           C  
HETATM   17  O2  UNL     1      -5.518   2.605   0.910  1.00  0.00           O  
HETATM   18  H1  UNL     1       7.443   0.282   0.492  1.00  0.00           H  
HETATM   19  H2  UNL     1       6.820  -1.283  -0.275  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.603  -1.032   1.477  1.00  0.00           H  
HETATM   21  H4  UNL     1       6.063   2.020   0.190  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.667   1.796  -0.886  1.00  0.00           H  
HETATM   23  H6  UNL     1       4.443   1.951   0.891  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.485  -1.860   0.336  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.972  -2.070  -0.881  1.00  0.00           H  
HETATM   26  H9  UNL     1       1.851  -1.930   0.900  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.144   1.242  -1.235  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.225   0.179  -2.152  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.512  -0.220  -2.102  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.236  -1.359   1.520  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.645   0.503  -0.538  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.826   0.631   1.257  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.653  -1.761  -0.483  1.00  0.00           H  
HETATM   34  H17 UNL     1      -2.854  -1.681   1.295  1.00  0.00           H  
HETATM   35  H18 UNL     1      -5.930  -0.860  -0.847  1.00  0.00           H  
HETATM   36  H19 UNL     1      -5.136  -2.197   0.001  1.00  0.00           H  
HETATM   37  H20 UNL     1      -5.966  -0.975   0.981  1.00  0.00           H  
HETATM   38  H21 UNL     1      -3.203   1.594   0.106  1.00  0.00           H  
HETATM   39  H22 UNL     1      -5.235   2.357  -1.073  1.00  0.00           H  
HETATM   40  H23 UNL     1      -6.237   1.085  -0.316  1.00  0.00           H  
HETATM   41  H24 UNL     1      -4.698   2.644   1.473  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    6    7
CONECT    7    8   25   26
CONECT    8    9   10   10
CONECT    9   27   28   29
CONECT   10   11   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   15   15
CONECT   14   35   36   37
CONECT   15   16   38
CONECT   16   17   39   40
CONECT   17   41
END

HMDB0030891
     RDKit          3D
(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one
 41 40  0  0  0  0  0  0  0  0999 V2000
    6.6766   -0.4941    0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2997    0.0611    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0754    1.5167    0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034   -0.7953    0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9374   -0.3511    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6653    0.8608   -0.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -1.3510   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5627   -0.6501   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3515    0.1631   -1.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883   -0.7700    0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6775   -0.0710    0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8176   -1.0644    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0824   -0.3310    0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3453   -1.1103    0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0951    0.9847    0.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3827    1.7414   -0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5181    2.6052    0.9098 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4427    0.2820    0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8199   -1.2833   -0.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6029   -1.0320    1.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0628    2.0197    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6666    1.7963   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4434    1.9505    0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4854   -1.8596    0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9721   -2.0700   -0.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8510   -1.9301    0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1440    1.2417   -1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2253    0.1791   -2.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5117   -0.2203   -2.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2365   -1.3588    1.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6447    0.5033   -0.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8257    0.6310    1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6528   -1.7611   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539   -1.6805    1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9300   -0.8601   -0.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1364   -2.1972    0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9655   -0.9753    0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2034    1.5942    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2348    2.3575   -1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2371    1.0846   -0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984    2.6436    1.4730 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 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
  7 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.3499

Monoisotopic Molecular Weight

236.177630012

IUPAC Name

(6E,10E)-12-hydroxy-2,6,10-trimethyldodeca-2,6,10-trien-4-one

Traditional Name

(6E,10E)-12-hydroxy-2,6,10-trimethyldodeca-2,6,10-trien-4-one

CAS Registry Number

79421-76-4

SMILES

CC(C)=CC(=O)C\C(C)=C\CC\C(C)=C\CO

InChI Identifier

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

InChI Key

VCXVMWVWGVWZPY-CCLLZULESA-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
Fatty alcohol
Fatty acyl
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Ketone
Primary alcohol
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030891)

Source

Endogenous

Endogenous (HMDB: HMDB0030891)

Plant

Plant (HMDB: HMDB0030891)

Animal

Animal (HMDB: HMDB0030891)

Exogenous

Food

Food (HMDB: HMDB0030891)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Root vegetable

Root vegetables (FooDB: FOOD00873)

Exogenous (HMDB: HMDB0030891)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0030891)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0030891)

Lipid metabolism pathway (HMDB: HMDB0030891)

Cellular process

Cell signaling (HMDB: HMDB0030891)

Biochemical process

Lipid transport (HMDB: HMDB0030891)

Role

Biological role

Energy source (HMDB: HMDB0030891)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030891)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	3.54	ALOGPS
logP	3.34	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	16.24	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	75.6 m³·mol⁻¹	ChemAxon
Polarizability	28.46 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]+	161.452	30932474
DeepCCS	[M-H]-	159.094	30932474
DeepCCS	[M-2H]-	192.013	30932474
DeepCCS	[M+Na]+	167.545	30932474
AllCCS	[M+H]+	160.9	32859911
AllCCS	[M+H-H2O]+	157.4	32859911
AllCCS	[M+NH4]+	164.1	32859911
AllCCS	[M+Na]+	165.1	32859911
AllCCS	[M-H]-	161.3	32859911
AllCCS	[M+Na-2H]-	162.3	32859911
AllCCS	[M+HCOO]-	163.5	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.	7.88 minutes	32390414
Predicted by Siyang on May 30, 2022	12.2547 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.49 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2367.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	258.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	162.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	70.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	427.6 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	457.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	64.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1071.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	445.9 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	968.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	345.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	348.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	259.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	306.2 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	7.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one	CC(C)=CC(=O)C\C(C)=C\CC\C(C)=C\CO	2691.7	Standard polar	33892256
(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one	CC(C)=CC(=O)C\C(C)=C\CC\C(C)=C\CO	1770.2	Standard non polar	33892256
(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one	CC(C)=CC(=O)C\C(C)=C\CC\C(C)=C\CO	1860.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one,1TMS,isomer #1	CC(C)=CC(=O)C/C(C)=C/CC/C(C)=C/CO[Si](C)(C)C	1904.3	Semi standard non polar	33892256
(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one,1TMS,isomer #2	CC(C)=CC(=C/C(C)=C/CC/C(C)=C/CO)O[Si](C)(C)C	2034.2	Semi standard non polar	33892256
(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one,2TMS,isomer #1	CC(C)=CC(=C/C(C)=C/CC/C(C)=C/CO[Si](C)(C)C)O[Si](C)(C)C	2143.1	Semi standard non polar	33892256
(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one,2TMS,isomer #1	CC(C)=CC(=C/C(C)=C/CC/C(C)=C/CO[Si](C)(C)C)O[Si](C)(C)C	2107.9	Standard non polar	33892256
(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one,1TBDMS,isomer #1	CC(C)=CC(=O)C/C(C)=C/CC/C(C)=C/CO[Si](C)(C)C(C)(C)C	2132.3	Semi standard non polar	33892256
(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one,1TBDMS,isomer #2	CC(C)=CC(=C/C(C)=C/CC/C(C)=C/CO)O[Si](C)(C)C(C)(C)C	2260.1	Semi standard non polar	33892256
(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one,2TBDMS,isomer #1	CC(C)=CC(=C/C(C)=C/CC/C(C)=C/CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2582.1	Semi standard non polar	33892256
(2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one,2TBDMS,isomer #1	CC(C)=CC(=C/C(C)=C/CC/C(C)=C/CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2507.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ul9-9740000000-b6f4a84750e10641d99a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one GC-MS (1 TMS) - 70eV, Positive	splash10-025l-9550000000-74359f715cb40e57df13	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one 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 - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one 10V, Positive-QTOF	splash10-014r-1490000000-725b3d3f06c8cee83ba2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one 20V, Positive-QTOF	splash10-014r-6930000000-5ca45ceaf12b13bc6529	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one 40V, Positive-QTOF	splash10-0pvi-9400000000-37555a8099405b24aad0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one 10V, Negative-QTOF	splash10-000i-0090000000-6a0a5b1e24378ae6e690	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one 20V, Negative-QTOF	splash10-0a4r-5390000000-1c1763e4f179950e262e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one 40V, Negative-QTOF	splash10-0a4i-9410000000-8a7c55d19caea3be3a13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one 10V, Negative-QTOF	splash10-000i-1190000000-822031d72213fbef7788	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one 20V, Negative-QTOF	splash10-001a-5890000000-4d14c7f1b868b48b1f6e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one 40V, Negative-QTOF	splash10-01pk-9500000000-3799682da972fe53dd38	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one 10V, Positive-QTOF	splash10-0fs9-4940000000-47505850ca928b078eae	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one 20V, Positive-QTOF	splash10-053s-9710000000-eac1c77758621b966a91	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one 40V, Positive-QTOF	splash10-0apl-9500000000-82c2c9200f67c8f2611a	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB002855

KNApSAcK ID

Not Available

Chemspider ID

30776860

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101648402

PDB ID

Not Available

ChEBI ID

173700

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

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 (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one (HMDB0030891)

MOL for HMDB0030891 ((2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one)

3D MOL for HMDB0030891 ((2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one)

3D SDF for HMDB0030891 ((2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one)

3D-SDF for HMDB0030891 ((2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one)

PDB for HMDB0030891 ((2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one)

3D PDB for HMDB0030891 ((2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one)

SMILES for HMDB0030891 ((2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one)

INCHI for HMDB0030891 ((2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one)

Structure for HMDB0030891 ((2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one)

3D Structure for HMDB0030891 ((2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra