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Showing metabocard for Ethyl (E)-2-nonenoate (HMDB0031272)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:42:02 UTC
Update Date2023-02-21 17:20:15 UTC
HMDB IDHMDB0031272
Secondary Accession Numbers
  • HMDB31272
Metabolite Identification
Common NameEthyl (E)-2-nonenoate
DescriptionEthyl (E)-2-nonenoate, also known as ethyl (e)-2-nonenoic 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-nonenoate.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031272 (Ethyl (E)-2-nonenoate)

  Mrv0541 05061305502D          

 13 12  0  0  0  0            999 V2000
    1.7605   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -0.1914    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  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13  4  1  0  0  0  0
 13 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0031272 (Ethyl (E)-2-nonenoate)

HMDB0031272
     RDKit          3D
Ethyl (E)-2-nonenoate
 33 32  0  0  0  0  0  0  0  0999 V2000
   -4.9605   -0.6425   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4137    0.4438    0.6168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0860    0.9784    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0398   -0.1266    0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586    0.4990   -0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3481   -0.5665   -0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5768   -1.1363    0.7960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7430   -1.0615    1.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9314   -0.4556    0.8824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9589   -0.5167    1.6664 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1813    0.1855   -0.2925 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4202    0.7445   -0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5230   -0.3003   -0.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6725   -1.6500    0.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5714   -0.4833   -1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0671   -0.6167   -0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3411    0.1022    1.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1325    1.2954    0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2477    1.3790   -0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7708    1.7888    0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3199   -0.9261   -0.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9421   -0.5319    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9299    0.8904   -1.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4086    1.2971    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643   -1.3556   -1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1962   -0.0493   -0.9732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2714   -1.6514    1.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7963   -1.5310    2.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7151    1.6068   -0.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3159    1.1220   -1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1690   -0.2276    0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0318   -1.2976   -0.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0906   -0.2697   -1.6498 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
M  END
Download

3D SDF for HMDB0031272 (Ethyl (E)-2-nonenoate)

  Mrv0541 05061305502D          

 13 12  0  0  0  0            999 V2000
    1.7605   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -0.1914    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  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13  4  1  0  0  0  0
 13 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031272

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H20O2/c1-3-5-6-7-8-9-10-11(12)13-4-2/h9-10H,3-8H2,1-2H3/b10-9-

> <INCHI_KEY>
ZCSDUGXKKBIICL-KTKRTIGZSA-N

> <FORMULA>
C11H20O2

> <MOLECULAR_WEIGHT>
184.2753

> <EXACT_MASS>
184.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.015038342964026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.43

> <JCHEM_LOGP>
3.8784609563333325

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.7909926108863

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
55.4876

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.46e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0031272 (Ethyl (E)-2-nonenoate)

HMDB0031272
     RDKit          3D
Ethyl (E)-2-nonenoate
 33 32  0  0  0  0  0  0  0  0999 V2000
   -4.9605   -0.6425   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4137    0.4438    0.6168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0860    0.9784    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0398   -0.1266    0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586    0.4990   -0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3481   -0.5665   -0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5768   -1.1363    0.7960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7430   -1.0615    1.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9314   -0.4556    0.8824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9589   -0.5167    1.6664 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1813    0.1855   -0.2925 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4202    0.7445   -0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5230   -0.3003   -0.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6725   -1.6500    0.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5714   -0.4833   -1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0671   -0.6167   -0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3411    0.1022    1.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1325    1.2954    0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2477    1.3790   -0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7708    1.7888    0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3199   -0.9261   -0.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9421   -0.5319    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9299    0.8904   -1.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4086    1.2971    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643   -1.3556   -1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1962   -0.0493   -0.9732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2714   -1.6514    1.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7963   -1.5310    2.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7151    1.6068   -0.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3159    1.1220   -1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1690   -0.2276    0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0318   -1.2976   -0.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0906   -0.2697   -1.6498 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
M  END
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PDB for HMDB0031272 (Ethyl (E)-2-nonenoate)

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       3.286  -3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.622   1.953   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.288   1.183   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.954  -3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.287  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.621  -3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.955  -2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.288  -3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.622  -2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.622  -1.127   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.956  -0.357   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      11.288  -0.357   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2   13                                                       
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13    4   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for HMDB0031272 (Ethyl (E)-2-nonenoate)

COMPND    HMDB0031272
HETATM    1  C1  UNL     1      -4.960  -0.642  -0.281  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.414   0.444   0.617  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.086   0.978   0.122  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.040  -0.127   0.060  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.759   0.499  -0.441  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.348  -0.566  -0.533  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.577  -1.136   0.796  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.743  -1.061   1.384  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.931  -0.456   0.882  1.00  0.00           C  
HETATM   10  O1  UNL     1       3.959  -0.517   1.666  1.00  0.00           O  
HETATM   11  O2  UNL     1       3.181   0.186  -0.293  1.00  0.00           O  
HETATM   12  C10 UNL     1       4.420   0.745  -0.664  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.523  -0.300  -0.711  1.00  0.00           C  
HETATM   14  H1  UNL     1      -4.673  -1.650   0.038  1.00  0.00           H  
HETATM   15  H2  UNL     1      -4.571  -0.483  -1.305  1.00  0.00           H  
HETATM   16  H3  UNL     1      -6.067  -0.617  -0.344  1.00  0.00           H  
HETATM   17  H4  UNL     1      -4.341   0.102   1.671  1.00  0.00           H  
HETATM   18  H5  UNL     1      -5.132   1.295   0.551  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.248   1.379  -0.893  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.771   1.789   0.778  1.00  0.00           H  
HETATM   21  H8  UNL     1      -2.320  -0.926  -0.623  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.942  -0.532   1.076  1.00  0.00           H  
HETATM   23  H10 UNL     1      -0.930   0.890  -1.460  1.00  0.00           H  
HETATM   24  H11 UNL     1      -0.409   1.297   0.254  1.00  0.00           H  
HETATM   25  H12 UNL     1      -0.064  -1.356  -1.217  1.00  0.00           H  
HETATM   26  H13 UNL     1       1.196  -0.049  -0.973  1.00  0.00           H  
HETATM   27  H14 UNL     1      -0.271  -1.651   1.321  1.00  0.00           H  
HETATM   28  H15 UNL     1       1.796  -1.531   2.393  1.00  0.00           H  
HETATM   29  H16 UNL     1       4.715   1.607  -0.044  1.00  0.00           H  
HETATM   30  H17 UNL     1       4.316   1.122  -1.709  1.00  0.00           H  
HETATM   31  H18 UNL     1       6.169  -0.228   0.185  1.00  0.00           H  
HETATM   32  H19 UNL     1       5.032  -1.298  -0.653  1.00  0.00           H  
HETATM   33  H20 UNL     1       6.091  -0.270  -1.650  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17   18
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8    8   27
CONECT    8    9   28
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   29   30
CONECT   13   31   32   33
END
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SMILES for HMDB0031272 (Ethyl (E)-2-nonenoate)

CCCCCC\C=C/C(=O)OCC
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INCHI for HMDB0031272 (Ethyl (E)-2-nonenoate)

InChI=1S/C11H20O2/c1-3-5-6-7-8-9-10-11(12)13-4-2/h9-10H,3-8H2,1-2H3/b10-9-
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Synonyms
ValueSource
Ethyl (e)-2-nonenoic acidGenerator
Ethyl (2Z)-non-2-enoic acidHMDB
Chemical FormulaC11H20O2
Average Molecular Weight184.2753
Monoisotopic Molecular Weight184.146329884
IUPAC Nameethyl (2Z)-non-2-enoate
Traditional Nameethyl (2Z)-non-2-enoate
CAS Registry Number38112-59-3
SMILES
CCCCCC\C=C/C(=O)OCC
InChI Identifier
InChI=1S/C11H20O2/c1-3-5-6-7-8-9-10-11(12)13-4-2/h9-10H,3-8H2,1-2H3/b10-9-
InChI KeyZCSDUGXKKBIICL-KTKRTIGZSA-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 effectNot Available
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 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
  • 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 IDFDB003316
KNApSAcK IDNot Available
Chemspider ID30776896
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12277543
PDB IDNot Available
ChEBI ID172050
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.