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Showing metabocard for 10-hydroxy-(2E,8E)-decadien-4-ynoic Acid (HMDB0062773)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 06:13:49 UTC
Update Date2023-02-21 17:31:09 UTC
HMDB IDHMDB0062773
Secondary Accession Numbers
  • HMDB62773
Metabolite Identification
Common Name10-hydroxy-(2E,8E)-decadien-4-ynoic Acid
Description10-hydroxy-(2E,8E)-decadien-4-ynoic acid belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 10-hydroxy-(2E,8E)-decadien-4-ynoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1677000669
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0062773 (10-hydroxy-(2E,8E)-decadien-4-ynoic Acid)

  Mrv1652303231707132D          

 17 16  0  0  0  0            999 V2000
    4.5375    2.1434    0.0000 H   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
    4.5375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    3.5724    0.0000 H   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
    2.0625    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
    1.2375    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
    1.2375   -0.7145    0.0000 H   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
   -0.4125    0.7145    0.0000 H   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
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  3  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
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3D MOL for HMDB0062773 (10-hydroxy-(2E,8E)-decadien-4-ynoic Acid)

HMDB0062773
     RDKit          3D
10-hydroxy-(2E,8E)-decadien-4-ynoic Acid
 25 24  0  0  0  0  0  0  0  0999 V2000
   -6.2401    0.7545    0.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7363   -0.2785   -0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5871   -1.2722   -0.7993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2901   -0.4096   -0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4623    0.5268   -0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0299    0.4126   -0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8322    0.3067   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6405    0.1684   -0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2882    0.8158    0.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7654    0.6816    0.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3243    0.0651   -0.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8299   -0.0216   -0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1095   -1.4077   -0.4744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3415   -2.2235   -0.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8872   -1.3143   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8567    1.4323    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9264   -0.9052   -0.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9927    0.6390   -1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9443    0.3338    1.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0581    1.9068    0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3969    1.1098    1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7571   -0.3687   -1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2266    0.4630   -1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2643    0.3604    0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7392   -1.7752    0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  3  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  8 17  1  0
  8 18  1  0
  9 19  1  0
  9 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 12 24  1  0
 13 25  1  0
M  END
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3D SDF for HMDB0062773 (10-hydroxy-(2E,8E)-decadien-4-ynoic Acid)

  Mrv1652303231707132D          

 17 16  0  0  0  0            999 V2000
    4.5375    2.1434    0.0000 H   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
    4.5375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    3.5724    0.0000 H   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
    2.0625    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
    1.2375    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
    1.2375   -0.7145    0.0000 H   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
   -0.4125    0.7145    0.0000 H   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
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  3  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062773

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CO)=C(\[H])CCC#C\C([H])=C(/[H])C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O3/c11-9-7-5-3-1-2-4-6-8-10(12)13/h5-8,11H,1,3,9H2,(H,12,13)/b7-5+,8-6+

> <INCHI_KEY>
YKLIFQPPZZVFPR-KQQUZDAGSA-N

> <FORMULA>
C10H12O3

> <MOLECULAR_WEIGHT>
180.203

> <EXACT_MASS>
180.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.955932939540762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,8E)-10-hydroxydeca-2,8-dien-4-ynoic acid

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
1.5290081286666664

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.081455372299907

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.384997464709349

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3257714201564017

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
52.8236

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,8E)-10-hydroxydeca-2,8-dien-4-ynoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0062773 (10-hydroxy-(2E,8E)-decadien-4-ynoic Acid)

HMDB0062773
     RDKit          3D
10-hydroxy-(2E,8E)-decadien-4-ynoic Acid
 25 24  0  0  0  0  0  0  0  0999 V2000
   -6.2401    0.7545    0.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7363   -0.2785   -0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5871   -1.2722   -0.7993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2901   -0.4096   -0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4623    0.5268   -0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0299    0.4126   -0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8322    0.3067   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6405    0.1684   -0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2882    0.8158    0.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7654    0.6816    0.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3243    0.0651   -0.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8299   -0.0216   -0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1095   -1.4077   -0.4744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3415   -2.2235   -0.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8872   -1.3143   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8567    1.4323    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9264   -0.9052   -0.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9927    0.6390   -1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9443    0.3338    1.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0581    1.9068    0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3969    1.1098    1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7571   -0.3687   -1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2266    0.4630   -1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2643    0.3604    0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7392   -1.7752    0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  3  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  8 17  1  0
  8 18  1  0
  9 19  1  0
  9 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 12 24  1  0
 13 25  1  0
M  END
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PDB for HMDB0062773 (10-hydroxy-(2E,8E)-decadien-4-ynoic Acid)

HEADER    PROTEIN                                 23-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-17         0                                  
HETATM    1  H   UNK     0       8.470   4.001   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       7.700   5.335   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  O   UNK     0      10.010   6.668   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.160   5.335   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       5.390   6.668   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       5.390   4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850   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       2.310   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  H   UNK     0       2.310  -1.334   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      -0.770   1.334   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END
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3D PDB for HMDB0062773 (10-hydroxy-(2E,8E)-decadien-4-ynoic Acid)

COMPND    HMDB0062773
HETATM    1  O1  UNL     1      -6.240   0.755   0.120  1.00  0.00           O  
HETATM    2  C1  UNL     1      -5.736  -0.279  -0.387  1.00  0.00           C  
HETATM    3  O2  UNL     1      -6.587  -1.272  -0.799  1.00  0.00           O  
HETATM    4  C2  UNL     1      -4.290  -0.410  -0.530  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.462   0.527  -0.143  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.030   0.413  -0.278  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.832   0.307  -0.372  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.640   0.168  -0.487  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.288   0.816   0.691  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.765   0.682   0.582  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.324   0.065  -0.442  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.830  -0.022  -0.466  1.00  0.00           C  
HETATM   13  O3  UNL     1       5.110  -1.408  -0.474  1.00  0.00           O  
HETATM   14  H1  UNL     1      -6.341  -2.223  -0.606  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.887  -1.314  -0.972  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.857   1.432   0.299  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.926  -0.905  -0.528  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.993   0.639  -1.413  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.944   0.334   1.648  1.00  0.00           H  
HETATM   20  H7  UNL     1       1.058   1.907   0.712  1.00  0.00           H  
HETATM   21  H8  UNL     1       3.397   1.110   1.379  1.00  0.00           H  
HETATM   22  H9  UNL     1       2.757  -0.369  -1.244  1.00  0.00           H  
HETATM   23  H10 UNL     1       5.227   0.463  -1.372  1.00  0.00           H  
HETATM   24  H11 UNL     1       5.264   0.360   0.469  1.00  0.00           H  
HETATM   25  H12 UNL     1       4.739  -1.775   0.365  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5    5   15
CONECT    5    6   16
CONECT    6    7    7    7
CONECT    7    8
CONECT    8    9   17   18
CONECT    9   10   19   20
CONECT   10   11   11   21
CONECT   11   12   22
CONECT   12   13   23   24
CONECT   13   25
END
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SMILES for HMDB0062773 (10-hydroxy-(2E,8E)-decadien-4-ynoic Acid)

[H]\C(CO)=C(\[H])CCC#C\C([H])=C(/[H])C(O)=O
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INCHI for HMDB0062773 (10-hydroxy-(2E,8E)-decadien-4-ynoic Acid)

InChI=1S/C10H12O3/c11-9-7-5-3-1-2-4-6-8-10(12)13/h5-8,11H,1,3,9H2,(H,12,13)/b7-5+,8-6+
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Synonyms
ValueSource
10-Hydroxy-2E,8E-decadien-4-ynoic acidChEBI
10-Hydroxy-2E,8E-decadien-4-ynoateGenerator
10-Hydroxy-(2E,8E)-decadien-4-ynoateGenerator
Chemical FormulaC10H12O3
Average Molecular Weight180.203
Monoisotopic Molecular Weight180.078644246
IUPAC Name(2E,8E)-10-hydroxydeca-2,8-dien-4-ynoic acid
Traditional Name(2E,8E)-10-hydroxydeca-2,8-dien-4-ynoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CO)=C(\[H])CCC#C\C([H])=C(/[H])C(O)=O
InChI Identifier
InChI=1S/C10H12O3/c11-9-7-5-3-1-2-4-6-8-10(12)13/h5-8,11H,1,3,9H2,(H,12,13)/b7-5+,8-6+
InChI KeyYKLIFQPPZZVFPR-KQQUZDAGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.12 g/lALOGPS
LogP1.68ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543616
PDB IDNot Available
ChEBI ID72691
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Xiao JF, Varghese RS, Zhou B, Nezami Ranjbar MR, Zhao Y, Tsai TH, Di Poto C, Wang J, Goerlitz D, Luo Y, Cheema AK, Sarhan N, Soliman H, Tadesse MG, Ziada DH, Ressom HW: LC-MS based serum metabolomics for identification of hepatocellular carcinoma biomarkers in Egyptian cohort. J Proteome Res. 2012 Dec 7;11(12):5914-23. doi: 10.1021/pr300673x. Epub 2012 Nov 1. [PubMed:23078175 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.