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Showing metabocard for L-erythro-4-Hydroxyarginine (HMDB0034326)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:08:14 UTC
Update Date2022-03-07 02:54:04 UTC
HMDB IDHMDB0034326
Secondary Accession Numbers
  • HMDB34326
Metabolite Identification
Common NameL-erythro-4-Hydroxyarginine
DescriptionL-erythro-4-Hydroxyarginine belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). L-erythro-4-Hydroxyarginine has been detected, but not quantified in, pulses. This could make L-erythro-4-hydroxyarginine a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on L-erythro-4-Hydroxyarginine.
Structure
Data?1563862545
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0034326 (L-erythro-4-Hydroxyarginine)

  Mrv0541 05061307432D          

 13 12  0  0  0  0            999 V2000
    3.6829    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    0.0000    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
    4.3974    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  7  4  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  2  1  0  0  0  0
 10  6  1  0  0  0  0
 11  3  1  0  0  0  0
 12  5  2  0  0  0  0
 13  5  1  0  0  0  0
M  END
Download

3D MOL for HMDB0034326 (L-erythro-4-Hydroxyarginine)

HMDB0034326
     RDKit          3D
L-erythro-4-Hydroxyarginine
 27 26  0  0  0  0  0  0  0  0999 V2000
    3.9745   -1.2323   -0.1605 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2645   -0.3484    0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7412    0.9762    0.5010 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0218   -0.6940    0.9932 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -0.0331    0.7732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2259   -0.1955   -0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733    0.3013   -1.5901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874    0.5152   -0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1295   -0.0281    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3560   -1.4468   -0.0379 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3800    0.7020   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3695    0.0418   -0.5415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4529    2.0603    0.1033 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018   -2.2362   -0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1427    1.3360    1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7117    1.6197   -0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352   -1.5167    1.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0576   -0.4057    1.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403    1.0527    0.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761   -1.3015   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486   -0.4012   -2.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9998    1.6080   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4784    0.4344   -1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8036    0.0970    1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2624   -1.6857    0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4918   -1.6287   -1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1669    2.4094    0.7532 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 13 27  1  0
M  END
Download

3D SDF for HMDB0034326 (L-erythro-4-Hydroxyarginine)

  Mrv0541 05061307432D          

 13 12  0  0  0  0            999 V2000
    3.6829    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    0.0000    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
    4.3974    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  7  4  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  2  1  0  0  0  0
 10  6  1  0  0  0  0
 11  3  1  0  0  0  0
 12  5  2  0  0  0  0
 13  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034326

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(CC(O)CNC(N)=N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H14N4O3/c7-4(5(12)13)1-3(11)2-10-6(8)9/h3-4,11H,1-2,7H2,(H,12,13)(H4,8,9,10)

> <INCHI_KEY>
OPCBKDJCJYBGTQ-UHFFFAOYSA-N

> <FORMULA>
C6H14N4O3

> <MOLECULAR_WEIGHT>
190.2004

> <EXACT_MASS>
190.106590334

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
18.673509763895176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-5-carbamimidamido-4-hydroxypentanoic acid

> <ALOGPS_LOGP>
-3.96

> <JCHEM_LOGP>
-4.308763290003327

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.838668225905337

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1976627334047447

> <JCHEM_PKA_STRONGEST_BASIC>
12.109634313882735

> <JCHEM_POLAR_SURFACE_AREA>
145.45

> <JCHEM_REFRACTIVITY>
55.241

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-hydroxyarginine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0034326 (L-erythro-4-Hydroxyarginine)

HMDB0034326
     RDKit          3D
L-erythro-4-Hydroxyarginine
 27 26  0  0  0  0  0  0  0  0999 V2000
    3.9745   -1.2323   -0.1605 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2645   -0.3484    0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7412    0.9762    0.5010 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0218   -0.6940    0.9932 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -0.0331    0.7732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2259   -0.1955   -0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733    0.3013   -1.5901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874    0.5152   -0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1295   -0.0281    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3560   -1.4468   -0.0379 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3800    0.7020   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3695    0.0418   -0.5415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4529    2.0603    0.1033 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018   -2.2362   -0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1427    1.3360    1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7117    1.6197   -0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352   -1.5167    1.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0576   -0.4057    1.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403    1.0527    0.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761   -1.3015   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486   -0.4012   -2.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9998    1.6080   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4784    0.4344   -1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8036    0.0970    1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2624   -1.6857    0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4918   -1.6287   -1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1669    2.4094    0.7532 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 13 27  1  0
M  END
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PDB for HMDB0034326 (L-erythro-4-Hydroxyarginine)

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       6.875   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.208   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.542   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       8.208   2.310   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       0.206   0.770   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       1.540  -1.540   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       2.874   0.770   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       5.541   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      10.876   0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       9.542  -1.540   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    3   10                                                       
CONECT    3    1    2   11                                                  
CONECT    4    1    5    7                                                  
CONECT    5    4   12   13                                                  
CONECT    6    8    9   10                                                  
CONECT    7    4                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    2    6                                                       
CONECT   11    3                                                            
CONECT   12    5                                                            
CONECT   13    5                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for HMDB0034326 (L-erythro-4-Hydroxyarginine)

COMPND    HMDB0034326
HETATM    1  N1  UNL     1       3.974  -1.232  -0.161  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.265  -0.348   0.426  1.00  0.00           C  
HETATM    3  N2  UNL     1       3.741   0.976   0.501  1.00  0.00           N  
HETATM    4  N3  UNL     1       2.022  -0.694   0.993  1.00  0.00           N  
HETATM    5  C2  UNL     1       0.763  -0.033   0.773  1.00  0.00           C  
HETATM    6  C3  UNL     1       0.226  -0.195  -0.600  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.073   0.301  -1.590  1.00  0.00           O  
HETATM    8  C4  UNL     1      -1.087   0.515  -0.762  1.00  0.00           C  
HETATM    9  C5  UNL     1      -2.129  -0.028   0.185  1.00  0.00           C  
HETATM   10  N4  UNL     1      -2.356  -1.447  -0.038  1.00  0.00           N  
HETATM   11  C6  UNL     1      -3.380   0.702  -0.104  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.370   0.042  -0.542  1.00  0.00           O  
HETATM   13  O3  UNL     1      -3.453   2.060   0.103  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.702  -2.236  -0.264  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.143   1.336   1.419  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.712   1.620  -0.326  1.00  0.00           H  
HETATM   17  H4  UNL     1       2.035  -1.517   1.632  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.058  -0.406   1.529  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.940   1.053   0.991  1.00  0.00           H  
HETATM   20  H7  UNL     1       0.076  -1.302  -0.811  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.249  -0.401  -2.285  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.000   1.608  -0.592  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.478   0.434  -1.814  1.00  0.00           H  
HETATM   24  H11 UNL     1      -1.804   0.097   1.229  1.00  0.00           H  
HETATM   25  H12 UNL     1      -3.262  -1.686   0.421  1.00  0.00           H  
HETATM   26  H13 UNL     1      -2.492  -1.629  -1.068  1.00  0.00           H  
HETATM   27  H14 UNL     1      -4.167   2.409   0.753  1.00  0.00           H  
CONECT    1    2    2   14
CONECT    2    3    4
CONECT    3   15   16
CONECT    4    5   17
CONECT    5    6   18   19
CONECT    6    7    8   20
CONECT    7   21
CONECT    8    9   22   23
CONECT    9   10   11   24
CONECT   10   25   26
CONECT   11   12   12   13
CONECT   13   27
END
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SMILES for HMDB0034326 (L-erythro-4-Hydroxyarginine)

NC(CC(O)CNC(N)=N)C(O)=O
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INCHI for HMDB0034326 (L-erythro-4-Hydroxyarginine)

InChI=1S/C6H14N4O3/c7-4(5(12)13)1-3(11)2-10-6(8)9/h3-4,11H,1-2,7H2,(H,12,13)(H4,8,9,10)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-Amino-4-hydroxy-5-guanidopentanoic acidChEBI
2-Amino-5-{[amino(imino)methyl]amino}-4-hydroxypentanoic acidChEBI
2-Amino-4-hydroxy-5-guanidopentanoateGenerator
2-Amino-5-{[amino(imino)methyl]amino}-4-hydroxypentanoateGenerator
2-amino-5-(diaminomethylideneamino)-4-HydroxypentanoateGenerator, HMDB
4-Hydroxy-L-arginineHMDB
4-HydroxyarginineHMDB
4-Hydroxyarginine, 9ciHMDB
gamma-Hydroxy-L-arginineHMDB
gamma-HydroxyarginineHMDB
L-erythro-FormHMDB
g-HydroxyarginineGenerator
Γ-hydroxyarginineGenerator
gamma-Hydroxyarginine, (L)-isomerMeSH
Chemical FormulaC6H14N4O3
Average Molecular Weight190.2004
Monoisotopic Molecular Weight190.106590334
IUPAC Name2-amino-5-carbamimidamido-4-hydroxypentanoic acid
Traditional Namegamma-hydroxyarginine
CAS Registry Number61370-10-3
SMILES
NC(CC(O)CNC(N)=N)C(O)=O
InChI Identifier
InChI=1S/C6H14N4O3/c7-4(5(12)13)1-3(11)2-10-6(8)9/h3-4,11H,1-2,7H2,(H,12,13)(H4,8,9,10)
InChI KeyOPCBKDJCJYBGTQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Short-chain hydroxy acid
  • Fatty acid
  • 1,3-aminoalcohol
  • Guanidine
  • Secondary alcohol
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point190 - 191 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB012681
KNApSAcK IDC00001368
Chemspider ID3671412
KEGG Compound IDC08284
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4473082
PDB IDNot Available
ChEBI ID47829
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. (). 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.