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Showing metabocard for Ethyl (E)-2-octenoate (HMDB0037497)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:44:53 UTC
Update Date2023-02-21 17:25:51 UTC
HMDB IDHMDB0037497
Secondary Accession Numbers
  • HMDB37497
Metabolite Identification
Common NameEthyl (E)-2-octenoate
DescriptionEthyl (E)-2-octenoate, also known as ethyl (e)-2-octenoic acid, 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 small amount of articles have been published on Ethyl (E)-2-octenoate.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0037497 (Ethyl (E)-2-octenoate)

  Mrv0541 05061309492D          

 12 11  0  0  0  0            999 V2000
   -0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.3480    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
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12  4  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
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3D MOL for HMDB0037497 (Ethyl (E)-2-octenoate)

HMDB0037497
     RDKit          3D
Ethyl (E)-2-octenoate
 30 29  0  0  0  0  0  0  0  0999 V2000
   -2.9479    1.8441   -0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4189    0.7824    0.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2268   -0.0417    1.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6389   -0.6645   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4097   -1.5264    0.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0778   -2.0753   -0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696   -1.8686   -1.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2547   -1.0634   -0.7579 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834   -0.9678   -1.3855 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2116   -0.3815    0.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750    0.3807    0.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6910    1.4993    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1307    1.4662   -1.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5505    2.7690   -0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8777    2.0251   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8961    1.3157    1.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1451    0.1077    0.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4738    0.6506    1.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005   -0.7848    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2542    0.1558   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4008   -1.2905   -0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2302   -0.9252    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7808   -2.3673    1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6507   -2.7157   -1.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992   -2.3622   -2.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9384    0.8483    1.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1653   -0.2458    1.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5010    1.1978   -0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0093    2.4119    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966    1.8258   -0.5690 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 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
  5 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
M  END
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3D SDF for HMDB0037497 (Ethyl (E)-2-octenoate)

  Mrv0541 05061309492D          

 12 11  0  0  0  0            999 V2000
   -0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.3480    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
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12  4  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037497

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C(=O)OCC

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O2/c1-3-5-6-7-8-9-10(11)12-4-2/h8-9H,3-7H2,1-2H3/b9-8-

> <INCHI_KEY>
AISZSTYLOVXFII-HJWRWDBZSA-N

> <FORMULA>
C10H18O2

> <MOLECULAR_WEIGHT>
170.2487

> <EXACT_MASS>
170.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
20.16969209373461

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl (2Z)-oct-2-enoate

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.4338922913333327

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.79099261065857

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
50.8866

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl (2Z)-oct-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0037497 (Ethyl (E)-2-octenoate)

HMDB0037497
     RDKit          3D
Ethyl (E)-2-octenoate
 30 29  0  0  0  0  0  0  0  0999 V2000
   -2.9479    1.8441   -0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4189    0.7824    0.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2268   -0.0417    1.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6389   -0.6645   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4097   -1.5264    0.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0778   -2.0753   -0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696   -1.8686   -1.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2547   -1.0634   -0.7579 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834   -0.9678   -1.3855 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2116   -0.3815    0.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750    0.3807    0.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6910    1.4993    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1307    1.4662   -1.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5505    2.7690   -0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8777    2.0251   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8961    1.3157    1.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1451    0.1077    0.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4738    0.6506    1.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005   -0.7848    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2542    0.1558   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4008   -1.2905   -0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2302   -0.9252    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7808   -2.3673    1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6507   -2.7157   -1.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992   -2.3622   -2.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9384    0.8483    1.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1653   -0.2458    1.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5010    1.1978   -0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0093    2.4119    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966    1.8258   -0.5690 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 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
  5 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
M  END
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PDB for HMDB0037497 (Ethyl (E)-2-octenoate)

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      -0.357  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.645   3.286   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.311   2.516   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.311  -2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.645  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.645   0.206   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.978   0.976   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.311   0.976   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2   12                                                       
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12    4   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for HMDB0037497 (Ethyl (E)-2-octenoate)

COMPND    HMDB0037497
HETATM    1  C1  UNL     1      -2.948   1.844  -0.220  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.419   0.782   0.749  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.227  -0.042   1.199  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.639  -0.664  -0.051  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.410  -1.526   0.330  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.078  -2.075  -0.928  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.270  -1.869  -1.415  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.255  -1.063  -0.758  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.383  -0.968  -1.386  1.00  0.00           O  
HETATM   10  O2  UNL     1       2.212  -0.381   0.411  1.00  0.00           O  
HETATM   11  C9  UNL     1       3.275   0.381   0.942  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.691   1.499   0.019  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.131   1.466  -1.252  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.550   2.769  -0.126  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.878   2.025  -0.011  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.896   1.316   1.595  1.00  0.00           H  
HETATM   17  H5  UNL     1      -4.145   0.108   0.248  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.474   0.651   1.636  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.500  -0.785   1.958  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.254   0.156  -0.691  1.00  0.00           H  
HETATM   21  H9  UNL     1      -2.401  -1.291  -0.560  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.230  -0.925   0.938  1.00  0.00           H  
HETATM   23  H11 UNL     1      -0.781  -2.367   1.002  1.00  0.00           H  
HETATM   24  H12 UNL     1      -0.651  -2.716  -1.489  1.00  0.00           H  
HETATM   25  H13 UNL     1       1.499  -2.362  -2.401  1.00  0.00           H  
HETATM   26  H14 UNL     1       2.938   0.848   1.890  1.00  0.00           H  
HETATM   27  H15 UNL     1       4.165  -0.246   1.150  1.00  0.00           H  
HETATM   28  H16 UNL     1       4.501   1.198  -0.675  1.00  0.00           H  
HETATM   29  H17 UNL     1       4.009   2.412   0.588  1.00  0.00           H  
HETATM   30  H18 UNL     1       2.797   1.826  -0.569  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   22   23
CONECT    6    7    7   24
CONECT    7    8   25
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   26   27
CONECT   12   28   29   30
END
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SMILES for HMDB0037497 (Ethyl (E)-2-octenoate)

CCCCC\C=C/C(=O)OCC
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INCHI for HMDB0037497 (Ethyl (E)-2-octenoate)

InChI=1S/C10H18O2/c1-3-5-6-7-8-9-10(11)12-4-2/h8-9H,3-7H2,1-2H3/b9-8-
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Ethyl (e)-2-octenoic acidGenerator
(e)-Ethyl 2-octenoateHMDB
(e)-Oct-2-enoic acid ethyl esterHMDB
2-Octenoic acid, ethyl esterHMDB
Ethyl (2E)-2-octenoateHMDB
Ethyl (e)-oct-2-enoateHMDB
Ethyl 2-octenoateHMDB
Ethyl ester(e)-2-octenoic acidHMDB
Ethyl oct-2-enoateHMDB
Ethyl trans-2-octenoateHMDB
Ethyl-trans-2-octenoateHMDB
FEMA 3344?HMDB
trans-2-Octenoic acid ethyl esterHMDB
trans-2-Octenoic acid, ethyl esterHMDB
trans-Ethyl 2-octenoateHMDB
Chemical FormulaC10H18O2
Average Molecular Weight170.2487
Monoisotopic Molecular Weight170.13067982
IUPAC Nameethyl (2Z)-oct-2-enoate
Traditional Nameethyl (2Z)-oct-2-enoate
CAS Registry Number7367-82-0
SMILES
CCCCC\C=C/C(=O)OCC
InChI Identifier
InChI=1S/C10H18O2/c1-3-5-6-7-8-9-10(11)12-4-2/h8-9H,3-7H2,1-2H3/b9-8-
InChI KeyAISZSTYLOVXFII-HJWRWDBZSA-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
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate 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 Point94.00 °C. @ 30.00 mm HgThe Good Scents Company Information System
Water Solubility52.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.844 (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 IDFDB016572
KNApSAcK IDNot Available
Chemspider ID4509599
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5352768
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1433111
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.