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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 18:09:07 UTC

Update Date

2021-09-14 15:46:31 UTC

HMDB ID

HMDB0060626

Secondary Accession Numbers

HMDB60626

Metabolite Identification

Common Name

Malathion monocarboxylic acid

Description

Malathion monocarboxylic 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0060626
     RDKit          3D
Malathion monocarboxylic acid
 32 31  0  0  0  0  0  0  0  0999 V2000
   -1.1934   -2.8804    0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -2.0661    0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0010   -0.7644   -0.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4149    0.0645    0.8030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399   -0.3810    1.9442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0378    1.4379    0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3108    2.1120   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0645    3.4975   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9084    3.9840   -0.5277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    4.2943   -1.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1057    1.2453   -1.0404 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128    0.3489   -0.4112 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.1481    1.5654   -0.5306 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312   -0.0981    1.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8045   -1.0084    1.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3389   -0.9259   -1.4002 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267   -0.7556   -2.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3867   -3.9758    0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484   -2.6968    1.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3283   -2.5647    0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1754   -2.1244    0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7603   -2.5620   -0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5427    2.0164    1.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0984    2.0923    0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7376    1.5634   -0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9646    4.3968   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899   -0.4886    2.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926   -1.8788    2.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4593   -1.3018    0.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0188    0.2192   -1.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4128   -0.8247   -3.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2538   -1.5403   -1.7436 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
M  END


  Mrv0541 06151311092D          

 17 16  0  0  0  0            999 V2000
   -1.3184   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    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
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336    2.3645    0.0000 C   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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060626

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C(CC(O)=O)SP(=S)(OC)OC

> <INCHI_IDENTIFIER>
InChI=1S/C8H15O6PS2/c1-4-14-8(11)6(5-7(9)10)17-15(16,12-2)13-3/h6H,4-5H2,1-3H3,(H,9,10)

> <INCHI_KEY>
FARGSBYVTRDSKX-UHFFFAOYSA-N

> <FORMULA>
C8H15O6PS2

> <MOLECULAR_WEIGHT>
302.305

> <EXACT_MASS>
302.004766104

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.377893018625485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[dimethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}-4-ethoxy-4-oxobutanoic acid

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
1.354581195

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.3540869397309185

> <JCHEM_PKA_STRONGEST_BASIC>
-7.208767117901765

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
68.66460000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[dimethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}-4-ethoxy-4-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060626
     RDKit          3D
Malathion monocarboxylic acid
 32 31  0  0  0  0  0  0  0  0999 V2000
   -1.1934   -2.8804    0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -2.0661    0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0010   -0.7644   -0.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4149    0.0645    0.8030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399   -0.3810    1.9442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0378    1.4379    0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3108    2.1120   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0645    3.4975   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9084    3.9840   -0.5277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    4.2943   -1.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1057    1.2453   -1.0404 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128    0.3489   -0.4112 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.1481    1.5654   -0.5306 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312   -0.0981    1.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8045   -1.0084    1.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3389   -0.9259   -1.4002 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267   -0.7556   -2.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3867   -3.9758    0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484   -2.6968    1.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3283   -2.5647    0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1754   -2.1244    0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7603   -2.5620   -0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5427    2.0164    1.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0984    2.0923    0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7376    1.5634   -0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9646    4.3968   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899   -0.4886    2.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926   -1.8788    2.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4593   -1.3018    0.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0188    0.2192   -1.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4128   -0.8247   -3.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2538   -1.5403   -1.7436 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
M  END

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      -2.461  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.461  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.127  -1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.461   0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.874   2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.207   0.000   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0       0.206   2.310   0.000  0.00  0.00           S+0
HETATM   12  P   UNK     0      -1.127   3.080   0.000  0.00  0.00           P+0
HETATM   13  S   UNK     0      -2.461   3.850   0.000  0.00  0.00           S+0
HETATM   14  O   UNK     0      -1.897   1.746   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.437   1.746   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.357   4.414   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.183   4.414   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13   14   16                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   12   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0060626
HETATM    1  C1  UNL     1      -1.193  -2.880   0.634  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.385  -2.066   0.180  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.001  -0.764  -0.142  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.415   0.065   0.803  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.240  -0.381   1.944  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.038   1.438   0.370  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.311   2.112  -0.087  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.065   3.497  -0.546  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.908   3.984  -0.528  1.00  0.00           O  
HETATM   10  O4  UNL     1      -3.097   4.294  -1.006  1.00  0.00           O  
HETATM   11  S1  UNL     1       0.106   1.245  -1.040  1.00  0.00           S  
HETATM   12  P1  UNL     1       1.913   0.349  -0.411  1.00  0.00           P  
HETATM   13  S2  UNL     1       3.148   1.565  -0.531  1.00  0.00           S  
HETATM   14  O5  UNL     1       1.831  -0.098   1.215  1.00  0.00           O  
HETATM   15  C7  UNL     1       2.805  -1.008   1.566  1.00  0.00           C  
HETATM   16  O6  UNL     1       2.339  -0.926  -1.400  1.00  0.00           O  
HETATM   17  C8  UNL     1       3.527  -0.756  -2.069  1.00  0.00           C  
HETATM   18  H1  UNL     1      -1.387  -3.976   0.440  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.048  -2.697   1.714  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.328  -2.565   0.010  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.175  -2.124   0.945  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.760  -2.562  -0.746  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.543   2.016   1.146  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.098   2.092   0.691  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.738   1.563  -0.973  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.965   4.397  -0.518  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.490  -0.489   2.299  1.00  0.00           H  
HETATM   28  H11 UNL     1       2.393  -1.879   2.110  1.00  0.00           H  
HETATM   29  H12 UNL     1       3.459  -1.302   0.726  1.00  0.00           H  
HETATM   30  H13 UNL     1       4.019   0.219  -1.879  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.413  -0.825  -3.175  1.00  0.00           H  
HETATM   32  H15 UNL     1       4.254  -1.540  -1.744  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   11   23
CONECT    7    8   24   25
CONECT    8    9    9   10
CONECT   10   26
CONECT   11   12
CONECT   12   13   13   14   16
CONECT   14   15
CONECT   15   27   28   29
CONECT   16   17
CONECT   17   30   31   32
END

HMDB0060626
     RDKit          3D
Malathion monocarboxylic acid
 32 31  0  0  0  0  0  0  0  0999 V2000
   -1.1934   -2.8804    0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -2.0661    0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0010   -0.7644   -0.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4149    0.0645    0.8030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399   -0.3810    1.9442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0378    1.4379    0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3108    2.1120   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0645    3.4975   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9084    3.9840   -0.5277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    4.2943   -1.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1057    1.2453   -1.0404 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128    0.3489   -0.4112 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.1481    1.5654   -0.5306 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312   -0.0981    1.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8045   -1.0084    1.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3389   -0.9259   -1.4002 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267   -0.7556   -2.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3867   -3.9758    0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484   -2.6968    1.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3283   -2.5647    0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1754   -2.1244    0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7603   -2.5620   -0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5427    2.0164    1.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0984    2.0923    0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7376    1.5634   -0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9646    4.3968   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899   -0.4886    2.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926   -1.8788    2.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4593   -1.3018    0.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0188    0.2192   -1.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4128   -0.8247   -3.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2538   -1.5403   -1.7436 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Malathion monocarboxylate	Generator

Chemical Formula

C₈H₁₅O₆PS₂

Average Molecular Weight

302.305

Monoisotopic Molecular Weight

302.004766104

IUPAC Name

3-{[dimethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}-4-ethoxy-4-oxobutanoic acid

Traditional Name

3-{[dimethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}-4-ethoxy-4-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

CCOC(=O)C(CC(O)=O)SP(=S)(OC)OC

InChI Identifier

InChI=1S/C8H15O6PS2/c1-4-14-8(11)6(5-7(9)10)17-15(16,12-2)13-3/h6H,4-5H2,1-3H3,(H,9,10)

InChI Key

FARGSBYVTRDSKX-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Thia fatty acids

Alternative Parents

Substituents

Fatty acid ester
Thia fatty acid
Dicarboxylic acid or derivatives
Dithiophosphate o-ester
Dithiophosphate s-ester
Organic dithiophosphate
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organothiophosphorus compound
Sulfenyl compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Organosulfur compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060626)
Liver (HMDB: HMDB0060626)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060626)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060626)

Cellular substructure

Cytoplasm (HMDB: HMDB0060626)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.67 g/L	ALOGPS
logP	1.5	ALOGPS
logP	1.35	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	68.66 m³·mol⁻¹	ChemAxon
Polarizability	27.38 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	167.02	31661259
DarkChem	[M-H]-	162.121	31661259
DeepCCS	[M+H]+	155.695	30932474
DeepCCS	[M-H]-	153.337	30932474
DeepCCS	[M-2H]-	186.291	30932474
DeepCCS	[M+Na]+	161.789	30932474
AllCCS	[M+H]+	155.7	32859911
AllCCS	[M+H-H2O]+	153.2	32859911
AllCCS	[M+NH4]+	158.0	32859911
AllCCS	[M+Na]+	158.6	32859911
AllCCS	[M-H]-	160.4	32859911
AllCCS	[M+Na-2H]-	161.2	32859911
AllCCS	[M+HCOO]-	162.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Malathion monocarboxylic acid	CCOC(=O)C(CC(O)=O)SP(=S)(OC)OC	3186.3	Standard polar	33892256
Malathion monocarboxylic acid	CCOC(=O)C(CC(O)=O)SP(=S)(OC)OC	1827.2	Standard non polar	33892256
Malathion monocarboxylic acid	CCOC(=O)C(CC(O)=O)SP(=S)(OC)OC	2069.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Malathion monocarboxylic acid,1TMS,isomer #1	CCOC(=O)C(CC(=O)O[Si](C)(C)C)SP(=S)(OC)OC	2008.4	Semi standard non polar	33892256
Malathion monocarboxylic acid,1TBDMS,isomer #1	CCOC(=O)C(CC(=O)O[Si](C)(C)C(C)(C)C)SP(=S)(OC)OC	2215.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Malathion monocarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-5390000000-9ff17fa6d1f9e705eed5	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malathion monocarboxylic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0udi-8439000000-6544e3c43666a9e9d496	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malathion monocarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malathion monocarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion monocarboxylic acid 10V, Positive-QTOF	splash10-0h00-0980000000-c01f175385c5970f1ff8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion monocarboxylic acid 20V, Positive-QTOF	splash10-00fr-8390000000-0a4238806b33de860e36	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion monocarboxylic acid 40V, Positive-QTOF	splash10-0udi-1900000000-fbb8b7422f05c896e260	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion monocarboxylic acid 10V, Negative-QTOF	splash10-0udi-1092000000-3bb0c9be0da584649d78	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion monocarboxylic acid 20V, Negative-QTOF	splash10-01r2-4590000000-a27ae2b1b2303130e7f0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion monocarboxylic acid 40V, Negative-QTOF	splash10-0592-2950000000-95f1e9dbd4e53cbabdad	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion monocarboxylic acid 10V, Positive-QTOF	splash10-0fk9-0903000000-9725c55a6222f0fdc348	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion monocarboxylic acid 20V, Positive-QTOF	splash10-00di-0900000000-db3f44b414be838db21a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion monocarboxylic acid 40V, Positive-QTOF	splash10-00fr-0900000000-86807745d3ff23b030e5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion monocarboxylic acid 10V, Negative-QTOF	splash10-0udi-0409000000-5f10d7fc86808eb2a8cb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion monocarboxylic acid 20V, Negative-QTOF	splash10-00di-1900000000-fb8187b912b1ce0a08a8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion monocarboxylic acid 40V, Negative-QTOF	splash10-05fr-0900000000-17cfb54bd357ece1f76c	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3032927

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Malathion monocarboxylic acid (HMDB0060626)

MOL for HMDB0060626 (Malathion monocarboxylic acid)

3D MOL for HMDB0060626 (Malathion monocarboxylic acid)

3D SDF for HMDB0060626 (Malathion monocarboxylic acid)

3D-SDF for HMDB0060626 (Malathion monocarboxylic acid)

PDB for HMDB0060626 (Malathion monocarboxylic acid)

3D PDB for HMDB0060626 (Malathion monocarboxylic acid)

SMILES for HMDB0060626 (Malathion monocarboxylic acid)

INCHI for HMDB0060626 (Malathion monocarboxylic acid)

Structure for HMDB0060626 (Malathion monocarboxylic acid)

3D Structure for HMDB0060626 (Malathion monocarboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra