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Showing metabocard for (-)-Dihydrocarveol (HMDB0035825)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:50:56 UTC
Update Date2022-03-07 02:54:39 UTC
HMDB IDHMDB0035825
Secondary Accession Numbers
  • HMDB35825
Metabolite Identification
Common Name(-)-Dihydrocarveol
Description(-)-Dihydrocarveol 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 small amount of articles have been published on (-)-Dihydrocarveol.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0035825 ((-)-Dihydrocarveol)

  Mrv1652302102020352D          

 11 11  0  0  0  0            999 V2000
   -3.5063   -5.5982    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2207   -6.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2207   -6.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063   -7.2482    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7918   -6.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -6.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063   -4.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0773   -5.5982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063   -8.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -8.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2207   -8.4857    0.0000 C   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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  1  0  0  0
  6  8  1  0  0  0  0
  4  9  1  6  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0035825 ((-)-Dihydrocarveol)

HMDB0035825
     RDKit          3D
(-)-Dihydrocarveol
 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.0490    1.4885    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2450    0.5752   -0.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8658   -0.4838   -0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005    0.6045    0.1660 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0659    0.7406   -1.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421    0.6571   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7280   -0.6623   -0.2762 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1810   -0.9817   -0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0823   -0.6196    1.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3720    0.6145    1.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4148   -0.6949    0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1331    1.4885    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6149    2.2576    1.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9454   -0.5722   -0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096   -1.4841   -0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273   -0.2541   -2.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431    1.4440    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486   -0.0678   -1.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3197    1.7332   -1.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9127    0.7295   -1.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7028    1.5246   -0.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2196   -1.4496   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6722   -0.5992    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2785   -2.1008   -0.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6947   -0.6460   -1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392   -1.4331    1.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3198    0.5631    1.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9742   -0.8127    1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5882   -1.5589    0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  6
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END
Download

3D SDF for HMDB0035825 ((-)-Dihydrocarveol)

  Mrv1652302102020352D          

 11 11  0  0  0  0            999 V2000
   -3.5063   -5.5982    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2207   -6.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2207   -6.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063   -7.2482    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7918   -6.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -6.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063   -4.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0773   -5.5982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063   -8.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -8.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2207   -8.4857    0.0000 C   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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  1  0  0  0
  6  8  1  0  0  0  0
  4  9  1  6  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035825

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1CC[C@H](CC1O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-11H,1,4-6H2,2-3H3/t8-,9-,10?/m1/s1

> <INCHI_KEY>
KRCZYMFUWVJCLI-MGRQHWMJSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.2493

> <EXACT_MASS>
154.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.00232224470895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.316627336

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.994600424312566

> <JCHEM_PKA_STRONGEST_BASIC>
-1.051561774405684

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
47.22279999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0035825 ((-)-Dihydrocarveol)

HMDB0035825
     RDKit          3D
(-)-Dihydrocarveol
 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.0490    1.4885    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2450    0.5752   -0.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8658   -0.4838   -0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005    0.6045    0.1660 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0659    0.7406   -1.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421    0.6571   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7280   -0.6623   -0.2762 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1810   -0.9817   -0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0823   -0.6196    1.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3720    0.6145    1.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4148   -0.6949    0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1331    1.4885    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6149    2.2576    1.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9454   -0.5722   -0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096   -1.4841   -0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273   -0.2541   -2.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431    1.4440    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486   -0.0678   -1.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3197    1.7332   -1.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9127    0.7295   -1.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7028    1.5246   -0.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2196   -1.4496   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6722   -0.5992    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2785   -2.1008   -0.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6947   -0.6460   -1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392   -1.4331    1.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3198    0.5631    1.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9742   -0.8127    1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5882   -1.5589    0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  6
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END
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PDB for HMDB0035825 ((-)-Dihydrocarveol)

HEADER    PROTEIN                                 10-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-FEB-20         0                                  
HETATM    1  C   UNK     0      -6.545 -10.450   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.879 -11.220   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.879 -12.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.545 -13.530   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.211 -12.760   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.211 -11.220   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.545  -8.910   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.878 -10.450   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.545 -15.070   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.211 -15.840   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.879 -15.840   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    8                                                  
CONECT    7    1                                                            
CONECT    8    6                                                            
CONECT    9    4   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0035825 ((-)-Dihydrocarveol)

COMPND    HMDB0035825
HETATM    1  C1  UNL     1      -3.049   1.488   0.411  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.245   0.575  -0.104  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.866  -0.484  -0.969  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.801   0.604   0.166  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.066   0.741  -1.134  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.442   0.657  -0.947  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.728  -0.662  -0.276  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.181  -0.982  -0.172  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.082  -0.620   1.095  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.372   0.615   1.684  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.415  -0.695   0.853  1.00  0.00           C  
HETATM   12  H1  UNL     1      -4.133   1.489   0.224  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.615   2.258   1.037  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.945  -0.572  -0.742  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.410  -1.484  -0.715  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.727  -0.254  -2.033  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.543   1.444   0.812  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.349  -0.068  -1.823  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.320   1.733  -1.574  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.913   0.730  -1.927  1.00  0.00           H  
HETATM   21  H10 UNL     1       1.703   1.525  -0.278  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.220  -1.450  -0.865  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.672  -0.599   0.733  1.00  0.00           H  
HETATM   24  H13 UNL     1       3.279  -2.101  -0.168  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.695  -0.646  -1.094  1.00  0.00           H  
HETATM   26  H15 UNL     1       1.439  -1.433   1.749  1.00  0.00           H  
HETATM   27  H16 UNL     1       2.320   0.563   1.991  1.00  0.00           H  
HETATM   28  H17 UNL     1      -0.974  -0.813   1.795  1.00  0.00           H  
HETATM   29  H18 UNL     1      -0.588  -1.559   0.200  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   11   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8    9   22
CONECT    8   23   24   25
CONECT    9   10   11   26
CONECT   10   27
CONECT   11   28   29
END
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SMILES for HMDB0035825 ((-)-Dihydrocarveol)

C[C@@H]1CC[C@H](CC1O)C(C)=C
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INCHI for HMDB0035825 ((-)-Dihydrocarveol)

InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-11H,1,4-6H2,2-3H3/t8-,9-,10?/m1/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(1R,2R,4R)-DihydrocarveolHMDB
(1R,2R,4R)-P-Menth-8-en-2-olHMDB
(1R,2R,5R)-2-Methyl-5-(prop-1-en-2-yl)cyclohexanolHMDB
(1R,2R,5R)-5-Isopropenyl-2-methylcyclohexanolHMDB
Chemical FormulaC10H18O
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
IUPAC Name(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol
Traditional Name(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol
CAS Registry Number20549-47-7
SMILES
C[C@@H]1CC[C@H](CC1O)C(C)=C
InChI Identifier
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-11H,1,4-6H2,2-3H3/t8-,9-,10?/m1/s1
InChI KeyKRCZYMFUWVJCLI-MGRQHWMJSA-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
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point225.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility426.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.915 (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 Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014913
KNApSAcK IDC00010937
Chemspider ID35014027
KEGG Compound IDC11396
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443163
PDB IDNot Available
ChEBI ID149
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1106561
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.