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Showing metabocard for Malathion dicarboxylic acid (HMDB0060636)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-06-15 18:24:53 UTC
Update Date2021-09-14 15:47:54 UTC
HMDB IDHMDB0060636
Secondary Accession Numbers
  • HMDB60636
Metabolite Identification
Common NameMalathion dicarboxylic acid
DescriptionMalathion dicarboxylic acid is a metabolite of malathion. Malathion is an organophosphate parasympathomimetic which binds irreversibly to cholinesterase. Malathion is an insecticide of relatively low human toxicity; however, a 2010 study has shown that children with higher levels of organophosphate pesticide metabolites in their urine are more likely to have attention deficit hyperactivity disorder. In the former USSR it was known as carbophos, in New Zealand and Australia as maldison and in South Africa as mercaptothion. (Wikipedia)
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0060636 (Malathion dicarboxylic acid)

  Mrv0541 06151311242D          

 15 14  0  0  0  0            999 V2000
   -1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6039    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 S   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
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   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
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
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3D MOL for HMDB0060636 (Malathion dicarboxylic acid)

HMDB0060636
     RDKit          3D
Malathion dicarboxylic acid
 26 25  0  0  0  0  0  0  0  0999 V2000
   -3.1232    0.9852    1.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4343    1.5531    0.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842    0.5084   -0.3731 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.8182    0.9428   -1.9813 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8920   -1.0505   -0.4198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8701   -0.9814   -1.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3734    0.6494    0.9661 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8380   -0.2944    0.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616    0.1854   -0.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0156    1.5936   -0.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6556    2.0759   -1.4899 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7222    2.2959    0.6181 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5735   -1.7531    0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135   -2.3153   -0.6137 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0819   -2.5117    1.5225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3111    1.7872    1.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5076    0.2035    1.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0623    0.5723    0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2532    0.0455   -1.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7361   -1.6648   -1.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -1.3679   -2.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524   -0.1721    1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921    0.1013   -1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -0.4297   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314    2.1744    1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -3.1331    2.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  6 19  1  0
  6 20  1  0
  6 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 12 25  1  0
 15 26  1  0
M  END
Download

3D SDF for HMDB0060636 (Malathion dicarboxylic acid)

  Mrv0541 06151311242D          

 15 14  0  0  0  0            999 V2000
   -1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6039    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 S   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
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   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
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060636

> <DATABASE_NAME>
hmdb

> <SMILES>
COP(=S)(OC)SC(CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11O6PS2/c1-11-13(14,12-2)15-4(6(9)10)3-5(7)8/h4H,3H2,1-2H3,(H,7,8)(H,9,10)

> <INCHI_KEY>
NIUNKPWHNGMQRE-UHFFFAOYSA-N

> <FORMULA>
C6H11O6PS2

> <MOLECULAR_WEIGHT>
274.252

> <EXACT_MASS>
273.973465976

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
23.248435610144277

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[dimethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}butanedioic acid

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
0.8518791843333331

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.6449473483393175

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.002527597439338

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
59.14690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[dimethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0060636 (Malathion dicarboxylic acid)

HMDB0060636
     RDKit          3D
Malathion dicarboxylic acid
 26 25  0  0  0  0  0  0  0  0999 V2000
   -3.1232    0.9852    1.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4343    1.5531    0.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842    0.5084   -0.3731 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.8182    0.9428   -1.9813 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8920   -1.0505   -0.4198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8701   -0.9814   -1.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3734    0.6494    0.9661 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8380   -0.2944    0.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616    0.1854   -0.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0156    1.5936   -0.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6556    2.0759   -1.4899 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7222    2.2959    0.6181 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5735   -1.7531    0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135   -2.3153   -0.6137 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0819   -2.5117    1.5225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3111    1.7872    1.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5076    0.2035    1.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0623    0.5723    0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2532    0.0455   -1.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7361   -1.6648   -1.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -1.3679   -2.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524   -0.1721    1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921    0.1013   -1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -0.4297   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314    2.1744    1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -3.1331    2.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  6 19  1  0
  6 20  1  0
  6 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 12 25  1  0
 15 26  1  0
M  END
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PDB for HMDB0060636 (Malathion dicarboxylic acid)

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0      -2.310   4.001   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.540   2.667   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0       0.000   2.667   0.000  0.00  0.00           P+0
HETATM    4  S   UNK     0       0.000   1.127   0.000  0.00  0.00           S+0
HETATM    5  O   UNK     0       0.000   4.207   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   4.977   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       1.540   2.667   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.160   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    7                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END
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3D PDB for HMDB0060636 (Malathion dicarboxylic acid)

COMPND    HMDB0060636
HETATM    1  C1  UNL     1      -3.123   0.985   1.233  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.434   1.553   0.151  1.00  0.00           O  
HETATM    3  P1  UNL     1      -1.184   0.508  -0.373  1.00  0.00           P  
HETATM    4  S1  UNL     1      -0.818   0.943  -1.981  1.00  0.00           S  
HETATM    5  O2  UNL     1      -1.892  -1.051  -0.420  1.00  0.00           O  
HETATM    6  C2  UNL     1      -2.870  -0.981  -1.413  1.00  0.00           C  
HETATM    7  S2  UNL     1       0.373   0.649   0.966  1.00  0.00           S  
HETATM    8  C3  UNL     1       1.838  -0.294   0.571  1.00  0.00           C  
HETATM    9  C4  UNL     1       2.562   0.185  -0.658  1.00  0.00           C  
HETATM   10  C5  UNL     1       3.016   1.594  -0.527  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.656   2.076  -1.490  1.00  0.00           O  
HETATM   12  O4  UNL     1       2.722   2.296   0.618  1.00  0.00           O  
HETATM   13  C6  UNL     1       1.573  -1.753   0.478  1.00  0.00           C  
HETATM   14  O5  UNL     1       1.813  -2.315  -0.614  1.00  0.00           O  
HETATM   15  O6  UNL     1       1.082  -2.512   1.522  1.00  0.00           O  
HETATM   16  H1  UNL     1      -3.311   1.787   1.977  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.508   0.204   1.746  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.062   0.572   0.813  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.253   0.045  -1.579  1.00  0.00           H  
HETATM   20  H5  UNL     1      -3.736  -1.665  -1.172  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.473  -1.368  -2.390  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.552  -0.172   1.424  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.992   0.101  -1.581  1.00  0.00           H  
HETATM   24  H9  UNL     1       3.492  -0.430  -0.777  1.00  0.00           H  
HETATM   25  H10 UNL     1       3.331   2.174   1.414  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.663  -3.133   2.063  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4    5    7
CONECT    5    6
CONECT    6   19   20   21
CONECT    7    8
CONECT    8    9   13   22
CONECT    9   10   23   24
CONECT   10   11   11   12
CONECT   12   25
CONECT   13   14   14   15
CONECT   15   26
END
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SMILES for HMDB0060636 (Malathion dicarboxylic acid)

COP(=S)(OC)SC(CC(O)=O)C(O)=O
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INCHI for HMDB0060636 (Malathion dicarboxylic acid)

InChI=1S/C6H11O6PS2/c1-11-13(14,12-2)15-4(6(9)10)3-5(7)8/h4H,3H2,1-2H3,(H,7,8)(H,9,10)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Malathion dicarboxylateGenerator
Lamivudine-triphosphoric acidHMDB
Chemical FormulaC6H11O6PS2
Average Molecular Weight274.252
Monoisotopic Molecular Weight273.973465976
IUPAC Name2-{[dimethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}butanedioic acid
Traditional Name2-{[dimethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}butanedioic acid
CAS Registry NumberNot Available
SMILES
COP(=S)(OC)SC(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H11O6PS2/c1-11-13(14,12-2)15-4(6(9)10)3-5(7)8/h4H,3H2,1-2H3,(H,7,8)(H,9,10)
InChI KeyNIUNKPWHNGMQRE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentThia fatty acids
Alternative Parents
Substituents
  • Thia fatty acid
  • Dicarboxylic acid or derivatives
  • Dithiophosphate s-ester
  • Dithiophosphate o-ester
  • Organic dithiophosphate
  • Sulfenyl compound
  • Organothiophosphorus compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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 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
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID13827
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound75607486
PDB IDNot Available
ChEBI IDNot Available
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.