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Showing metabocard for 3-Methylbutyl pentanoate (HMDB0040529)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:05:13 UTC
Update Date2023-02-21 17:28:19 UTC
HMDB IDHMDB0040529
Secondary Accession Numbers
  • HMDB40529
Metabolite Identification
Common Name3-Methylbutyl pentanoate
Description3-Methylbutyl pentanoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a significant number of articles have been published on 3-Methylbutyl pentanoate.
Structure
Data?1677000499
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0040529 (3-Methylbutyl pentanoate)

  Mrv0541 05061311552D          

 12 11  0  0  0  0            999 V2000
    0.6336   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -0.3020    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
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6349   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
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3D MOL for HMDB0040529 (3-Methylbutyl pentanoate)

HMDB0040529
     RDKit          3D
3-Methylbutyl pentanoate
 32 31  0  0  0  0  0  0  0  0999 V2000
    5.0252   -0.1068    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2795   -0.0187   -0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7920   -0.2820   -0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2854    0.7790    0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8320    0.5981    0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2560    1.4095    1.4129 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640   -0.3862    0.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3012   -0.5711    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1249    0.6185   -0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878    0.3404    0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823    0.0638    1.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0342   -0.8799   -0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7431   -1.0231    1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1079   -0.1991    0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8445    0.8206    1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6666   -0.8232   -1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827    0.9859   -1.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6843   -1.2931   -0.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3282   -0.1921   -1.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    1.7917    0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7829    0.5521    1.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6220   -1.4379   -0.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5619   -0.8415    1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589    1.5418    0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9947    0.7672   -1.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2258    1.1895   -0.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7373   -1.0039    1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3693    0.7575    2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9853    0.2552    1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269   -1.7611   -0.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5570   -0.7820   -1.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1310   -0.8691   -0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
M  END
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3D SDF for HMDB0040529 (3-Methylbutyl pentanoate)

  Mrv0541 05061311552D          

 12 11  0  0  0  0            999 V2000
    0.6336   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -0.3020    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
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6349   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040529

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC(=O)OCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H20O2/c1-4-5-6-10(11)12-8-7-9(2)3/h9H,4-8H2,1-3H3

> <INCHI_KEY>
UBLAMKHIFZBBSS-UHFFFAOYSA-N

> <FORMULA>
C10H20O2

> <MOLECULAR_WEIGHT>
172.2646

> <EXACT_MASS>
172.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
21.44281126801392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methylbutyl pentanoate

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
3.123139629666666

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.032745826271359

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
49.66390000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoamyl valerianate

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0040529 (3-Methylbutyl pentanoate)

HMDB0040529
     RDKit          3D
3-Methylbutyl pentanoate
 32 31  0  0  0  0  0  0  0  0999 V2000
    5.0252   -0.1068    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2795   -0.0187   -0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7920   -0.2820   -0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2854    0.7790    0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8320    0.5981    0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2560    1.4095    1.4129 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640   -0.3862    0.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3012   -0.5711    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1249    0.6185   -0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878    0.3404    0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823    0.0638    1.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0342   -0.8799   -0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7431   -1.0231    1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1079   -0.1991    0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8445    0.8206    1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6666   -0.8232   -1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827    0.9859   -1.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6843   -1.2931   -0.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3282   -0.1921   -1.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    1.7917    0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7829    0.5521    1.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6220   -1.4379   -0.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5619   -0.8415    1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589    1.5418    0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9947    0.7672   -1.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2258    1.1895   -0.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7373   -1.0039    1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3693    0.7575    2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9853    0.2552    1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269   -1.7611   -0.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5570   -0.7820   -1.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1310   -0.8691   -0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
M  END
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PDB for HMDB0040529 (3-Methylbutyl pentanoate)

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       1.183  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.186  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.852  -2.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.516  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.518  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.185  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.852  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.517  -1.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.517  -2.874   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       7.851  -0.564   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5   10                                                       
CONECT    7    8    9                                                       
CONECT    8    7   12                                                       
CONECT    9    2    3    7                                                  
CONECT   10    6   11   12                                                  
CONECT   11   10                                                            
CONECT   12    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for HMDB0040529 (3-Methylbutyl pentanoate)

COMPND    HMDB0040529
HETATM    1  C1  UNL     1       5.025  -0.107   0.565  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.279  -0.019  -0.746  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.792  -0.282  -0.564  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.285   0.779   0.394  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.832   0.598   0.631  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.256   1.410   1.413  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.064  -0.386   0.065  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.301  -0.571   0.276  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.125   0.619  -0.136  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.588   0.340   0.124  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.882   0.064   1.564  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.034  -0.880  -0.680  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.743  -1.023   1.112  1.00  0.00           H  
HETATM   14  H2  UNL     1       6.108  -0.199   0.338  1.00  0.00           H  
HETATM   15  H3  UNL     1       4.844   0.821   1.142  1.00  0.00           H  
HETATM   16  H4  UNL     1       4.667  -0.823  -1.417  1.00  0.00           H  
HETATM   17  H5  UNL     1       4.383   0.986  -1.171  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.684  -1.293  -0.145  1.00  0.00           H  
HETATM   19  H7  UNL     1       2.328  -0.192  -1.568  1.00  0.00           H  
HETATM   20  H8  UNL     1       2.526   1.792   0.067  1.00  0.00           H  
HETATM   21  H9  UNL     1       2.783   0.552   1.382  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.622  -1.438  -0.349  1.00  0.00           H  
HETATM   23  H11 UNL     1      -1.562  -0.841   1.323  1.00  0.00           H  
HETATM   24  H12 UNL     1      -1.859   1.542   0.374  1.00  0.00           H  
HETATM   25  H13 UNL     1      -1.995   0.767  -1.223  1.00  0.00           H  
HETATM   26  H14 UNL     1      -4.226   1.190  -0.195  1.00  0.00           H  
HETATM   27  H15 UNL     1      -3.737  -1.004   1.832  1.00  0.00           H  
HETATM   28  H16 UNL     1      -3.369   0.757   2.260  1.00  0.00           H  
HETATM   29  H17 UNL     1      -4.985   0.255   1.712  1.00  0.00           H  
HETATM   30  H18 UNL     1      -3.627  -1.761  -0.147  1.00  0.00           H  
HETATM   31  H19 UNL     1      -3.557  -0.782  -1.678  1.00  0.00           H  
HETATM   32  H20 UNL     1      -5.131  -0.869  -0.744  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   10   11   12   26
CONECT   11   27   28   29
CONECT   12   30   31   32
END
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SMILES for HMDB0040529 (3-Methylbutyl pentanoate)

CCCCC(=O)OCCC(C)C
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INCHI for HMDB0040529 (3-Methylbutyl pentanoate)

InChI=1S/C10H20O2/c1-4-5-6-10(11)12-8-7-9(2)3/h9H,4-8H2,1-3H3
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Synonyms
ValueSource
3-Methylbutyl pentanoic acidGenerator
3-Methylbutyl pentanoate, 9ciHMDB
iso-Amyl N-valerateHMDB
Isoamyl valerateHMDB
Isopentyl pentanoateHMDB
Isopentyl valerate, 8ciHMDB
Valeric acid, 3-methylbutyl esterHMDB
Chemical FormulaC10H20O2
Average Molecular Weight172.2646
Monoisotopic Molecular Weight172.146329884
IUPAC Name3-methylbutyl pentanoate
Traditional Nameisoamyl valerianate
CAS Registry Number2050-09-1
SMILES
CCCCC(=O)OCCC(C)C
InChI Identifier
InChI=1S/C10H20O2/c1-4-5-6-10(11)12-8-7-9(2)3/h9H,4-8H2,1-3H3
InChI KeyUBLAMKHIFZBBSS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point185.00 to 186.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility38.59 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.686 (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 IDFDB020296
KNApSAcK IDNot Available
Chemspider ID67464
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74901
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1045091
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.