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Showing metabocard for (±)-Carvomenthol (HMDB0037223)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:27:56 UTC
Update Date2022-03-07 02:55:14 UTC
HMDB IDHMDB0037223
Secondary Accession Numbers
  • HMDB37223
Metabolite Identification
Common Name(±)-Carvomenthol
Description(±)-Carvomenthol belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a significant number of articles have been published on (±)-Carvomenthol.
Structure
Data?1563862996
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0037223 ((±)-Carvomenthol)

  Mrv0541 05061309392D          

 11 11  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
Download

3D MOL for HMDB0037223 ((±)-Carvomenthol)

HMDB0037223
     RDKit          3D
(±)-Carvomenthol
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.6356   -0.5334    1.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0656   -0.5117   -0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154    0.4704   -0.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5841   -0.3066   -0.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0045   -0.2841   -1.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4824   -0.4572   -1.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1268    0.4514   -0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3624   -0.2871    0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3359    0.9138    0.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6411    0.1535    1.9774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    0.9521    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436   -1.4225    1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5118    0.4092    1.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7369   -0.6982    1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2428   -1.5307   -0.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2329    1.0510   -1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6768   -0.0477   -1.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3173    1.2081   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427   -1.1761    0.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2599    0.6703   -1.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3899   -1.1766   -1.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9238   -0.2899   -2.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6614   -1.5377   -1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5541    1.3397   -0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6833    0.1041    1.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1071   -1.3789    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1896   -0.2726   -0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6530    1.9579    1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2642   -0.7442    1.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6193    1.1397    1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3593    1.8341   -0.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
M  END
Download

3D SDF for HMDB0037223 ((±)-Carvomenthol)

  Mrv0541 05061309392D          

 11 11  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037223

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1CCC(C)C(O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)10(11)6-9/h7-11H,4-6H2,1-3H3

> <INCHI_KEY>
ULJXKUJMXIVDOY-UHFFFAOYSA-N

> <FORMULA>
C10H20O

> <MOLECULAR_WEIGHT>
156.2652

> <EXACT_MASS>
156.151415262

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
19.77368567463584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-5-(propan-2-yl)cyclohexan-1-ol

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
2.6642731470000007

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.902468174549885

> <JCHEM_PKA_STRONGEST_BASIC>
-1.09186042045188

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
47.445299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-isopropyl-2-methylcyclohexan-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0037223 ((±)-Carvomenthol)

HMDB0037223
     RDKit          3D
(±)-Carvomenthol
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.6356   -0.5334    1.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0656   -0.5117   -0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154    0.4704   -0.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5841   -0.3066   -0.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0045   -0.2841   -1.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4824   -0.4572   -1.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1268    0.4514   -0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3624   -0.2871    0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3359    0.9138    0.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6411    0.1535    1.9774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    0.9521    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436   -1.4225    1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5118    0.4092    1.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7369   -0.6982    1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2428   -1.5307   -0.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2329    1.0510   -1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6768   -0.0477   -1.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3173    1.2081   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427   -1.1761    0.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2599    0.6703   -1.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3899   -1.1766   -1.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9238   -0.2899   -2.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6614   -1.5377   -1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5541    1.3397   -0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6833    0.1041    1.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1071   -1.3789    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1896   -0.2726   -0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6530    1.9579    1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2642   -0.7442    1.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6193    1.1397    1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3593    1.8341   -0.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
M  END
Download

PDB for HMDB0037223 ((±)-Carvomenthol)

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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    9   10                                                       
CONECT    7    1    2    9                                                  
CONECT    8    3    4   10                                                  
CONECT    9    5    6    7                                                  
CONECT   10    6    8   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0037223 ((±)-Carvomenthol)

COMPND    HMDB0037223
HETATM    1  C1  UNL     1      -2.636  -0.533   1.319  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.066  -0.512  -0.074  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.815   0.470  -0.899  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.584  -0.307  -0.037  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.005  -0.284  -1.436  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.482  -0.457  -1.290  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.127   0.451  -0.325  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.362  -0.287   0.215  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.336   0.914   0.824  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.641   0.154   1.977  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.147   0.952   0.627  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.244  -1.422   1.850  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.512   0.409   1.864  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.737  -0.698   1.222  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.243  -1.531  -0.504  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.233   1.051  -1.609  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.677  -0.048  -1.414  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.317   1.208  -0.217  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.143  -1.176   0.505  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.260   0.670  -1.953  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.390  -1.177  -1.962  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.924  -0.290  -2.316  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.661  -1.538  -1.079  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.554   1.340  -0.874  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.683   0.104   1.183  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.107  -1.379   0.346  1.00  0.00           H  
HETATM   27  H16 UNL     1       4.190  -0.273  -0.524  1.00  0.00           H  
HETATM   28  H17 UNL     1       1.653   1.958   1.100  1.00  0.00           H  
HETATM   29  H18 UNL     1       1.264  -0.744   1.921  1.00  0.00           H  
HETATM   30  H19 UNL     1      -0.619   1.140   1.603  1.00  0.00           H  
HETATM   31  H20 UNL     1      -0.359   1.834  -0.044  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5   11   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8    9   24
CONECT    8   25   26   27
CONECT    9   10   11   28
CONECT   10   29
CONECT   11   30   31
END
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SMILES for HMDB0037223 ((±)-Carvomenthol)

CC(C)C1CCC(C)C(O)C1
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INCHI for HMDB0037223 ((±)-Carvomenthol)

InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)10(11)6-9/h7-11H,4-6H2,1-3H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(+/-)-carvomentholHMDB
(1alpha,2beta,5alpha)-5-(Isopropyl)-2-methylcyclohexan-1-olHMDB
1-Methyl-4-isopropyl-2-cyclohexanolHMDB
3-Isopropyl-6-methylcyclohexanolHMDB
5-Isopropyl-2-methylcyclohexanolHMDB
CarvomentholHMDB
HexahydrocarvacrolHMDB
P-Menthan-2-olHMDB
Chemical FormulaC10H20O
Average Molecular Weight156.2652
Monoisotopic Molecular Weight156.151415262
IUPAC Name2-methyl-5-(propan-2-yl)cyclohexan-1-ol
Traditional Name5-isopropyl-2-methylcyclohexan-1-ol
CAS Registry Number499-69-4
SMILES
CC(C)C1CCC(C)C(O)C1
InChI Identifier
InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)10(11)6-9/h7-11H,4-6H2,1-3H3
InChI KeyULJXKUJMXIVDOY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Cyclohexanol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point222.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility298.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.216 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB016230
KNApSAcK IDNot Available
Chemspider ID78347
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound86850
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1036831
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.