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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:47 UTC

HMDB ID

HMDB0014910

Secondary Accession Numbers

HMDB14910

Metabolite Identification

Common Name

Malathion

Description

Malathion is only found in individuals that have used or taken this drug. It is a wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes. [PubChem]Malathion is a nonsystemic, wide-spectrum organophosphate insecticide. It inhibits acetylcholinesterase activity of most eukaryotes. Malathion is toxic to aquatic organisms, but has a relatively low toxicity for birds and mammals. The major metabolites of malathion are mono- and di-carboxylic acid derivatives, and malaoxon is a minor metabolite. However, it is malaoxon that is the strongest cholinesterase inhibitor. Cholinesterases catalyze the hydrolysis of the neurotransmitter acetylcholine into choline and acetic acid, a reaction necessary to allow a cholinergic neuron to return to its resting state after activation. Because of its essential function, chemicals that interfere with the action of cholinesterase are potent neurotoxins, causing muscle spasms and ultimately death.

Structure

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

HMDB0014910
     RDKit          3D
Malathion
 38 37  0  0  0  0  0  0  0  0999 V2000
   -3.9636   -2.6774    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8521   -2.9710   -0.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6100   -2.4149   -0.2114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320   -1.0351   -0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4177   -0.3103   -0.3220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1556   -0.4082    0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3828    0.5822   -0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366    1.2272    0.0058 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305   -0.2276    0.1556 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.3752   -0.3804   -1.2555 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4848    0.2738    1.4114 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0537    1.5104    1.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8357   -1.7376    0.6161 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3136   -2.7309   -0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720    1.7085   -0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1376    2.0310   -1.8565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8609    2.4482    0.3448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392    3.5392    0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1483    3.1748    0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7048   -3.5304    0.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6321   -2.7466    1.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5133   -1.7590    0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8035   -4.0399   -0.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1188   -2.4600   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5621   -1.2328    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995    0.0851    1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224    0.1253   -1.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1898    2.1549    0.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6747    1.3668    0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5800    1.9604    1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7338   -3.6572   -0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3780   -2.9856   -0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2013   -2.4934   -1.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3909    4.3883   -0.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7258    3.9134    1.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662    3.2552   -1.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8842    3.8895    0.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4268    2.1637    0.3968 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  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
  9 13  1  0
 13 14  1  0
  7 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
M  END


  Mrv1652307282022152D          

 19 18  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    0.9355    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
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    2.3645    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 13  3  1  0  0  0  0
 14  4  1  0  0  0  0
 15  5  1  0  0  0  0
 15  9  1  0  0  0  0
 16  6  1  0  0  0  0
 16 10  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 17  2  0  0  0  0
 19  8  1  0  0  0  0
 19 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014910

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H19O6PS2/c1-5-15-9(11)7-8(10(12)16-6-2)19-17(18,13-3)14-4/h8H,5-7H2,1-4H3

> <INCHI_KEY>
JXSJBGJIGXNWCI-UHFFFAOYSA-N

> <FORMULA>
C10H19O6PS2

> <MOLECULAR_WEIGHT>
330.358

> <EXACT_MASS>
330.036066232

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.65672482536084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-diethyl 2-{[dimethoxy(sulfanylidene)-lambda5-phosphanyl]sulfanyl}butanedioate

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
1.8572832056666668

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.821451036028483

> <JCHEM_POLAR_SURFACE_AREA>
71.06

> <JCHEM_REFRACTIVITY>
78.1823

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4-diethyl 2-{[dimethoxy(sulfanylidene)-lambda5-phosphanyl]sulfanyl}butanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014910
     RDKit          3D
Malathion
 38 37  0  0  0  0  0  0  0  0999 V2000
   -3.9636   -2.6774    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8521   -2.9710   -0.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6100   -2.4149   -0.2114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320   -1.0351   -0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4177   -0.3103   -0.3220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1556   -0.4082    0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3828    0.5822   -0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366    1.2272    0.0058 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305   -0.2276    0.1556 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.3752   -0.3804   -1.2555 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4848    0.2738    1.4114 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0537    1.5104    1.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8357   -1.7376    0.6161 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3136   -2.7309   -0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720    1.7085   -0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1376    2.0310   -1.8565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8609    2.4482    0.3448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392    3.5392    0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1483    3.1748    0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7048   -3.5304    0.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6321   -2.7466    1.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5133   -1.7590    0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8035   -4.0399   -0.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1188   -2.4600   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5621   -1.2328    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995    0.0851    1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224    0.1253   -1.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1898    2.1549    0.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6747    1.3668    0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5800    1.9604    1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7338   -3.6572   -0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3780   -2.9856   -0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2013   -2.4934   -1.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3909    4.3883   -0.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7258    3.9134    1.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662    3.2552   -1.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8842    3.8895    0.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4268    2.1637    0.3968 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  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
  9 13  1  0
 13 14  1  0
  7 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
M  END

HEADER    PROTEIN                                 28-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JUL-20         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.645   1.746   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.105   1.746   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
HETATM   16  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   17  P   UNK     0       5.335   3.080   0.000  0.00  0.00           P+0
HETATM   18  S   UNK     0       4.565   4.414   0.000  0.00  0.00           S+0
HETATM   19  S   UNK     0       4.001   2.310   0.000  0.00  0.00           S+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5    1   15                                                       
CONECT    6    2   16                                                       
CONECT    7    8    9                                                       
CONECT    8    7   10   19                                                  
CONECT    9    7   11   15                                                  
CONECT   10    8   12   16                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
CONECT   13    3   17                                                       
CONECT   14    4   17                                                       
CONECT   15    5    9                                                       
CONECT   16    6   10                                                       
CONECT   17   13   14   18   19                                             
CONECT   18   17                                                            
CONECT   19    8   17                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0014910
HETATM    1  C1  UNL     1      -3.964  -2.677   0.357  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.852  -2.971  -0.589  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.610  -2.415  -0.211  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.432  -1.035  -0.083  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.418  -0.310  -0.322  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.156  -0.408   0.314  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.383   0.582  -0.672  1.00  0.00           C  
HETATM    8  S1  UNL     1       1.937   1.227   0.006  1.00  0.00           S  
HETATM    9  P1  UNL     1       3.430  -0.228   0.156  1.00  0.00           P  
HETATM   10  S2  UNL     1       4.375  -0.380  -1.256  1.00  0.00           S  
HETATM   11  O3  UNL     1       4.485   0.274   1.411  1.00  0.00           O  
HETATM   12  C6  UNL     1       5.054   1.510   1.046  1.00  0.00           C  
HETATM   13  O4  UNL     1       2.836  -1.738   0.616  1.00  0.00           O  
HETATM   14  C7  UNL     1       3.314  -2.731  -0.202  1.00  0.00           C  
HETATM   15  C8  UNL     1      -0.572   1.708  -0.783  1.00  0.00           C  
HETATM   16  O5  UNL     1      -1.138   2.031  -1.857  1.00  0.00           O  
HETATM   17  O6  UNL     1      -0.861   2.448   0.345  1.00  0.00           O  
HETATM   18  C9  UNL     1      -1.739   3.539   0.406  1.00  0.00           C  
HETATM   19  C10 UNL     1      -3.148   3.175   0.015  1.00  0.00           C  
HETATM   20  H1  UNL     1      -4.705  -3.530   0.282  1.00  0.00           H  
HETATM   21  H2  UNL     1      -3.632  -2.747   1.436  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.513  -1.759   0.145  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.804  -4.040  -0.797  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.119  -2.460  -1.565  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.562  -1.233   0.523  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.299   0.085   1.318  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.522   0.125  -1.669  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.190   2.155   0.747  1.00  0.00           H  
HETATM   29  H10 UNL     1       5.675   1.367   0.141  1.00  0.00           H  
HETATM   30  H11 UNL     1       5.580   1.960   1.883  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.734  -3.657  -0.005  1.00  0.00           H  
HETATM   32  H13 UNL     1       4.378  -2.986  -0.009  1.00  0.00           H  
HETATM   33  H14 UNL     1       3.201  -2.493  -1.278  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.391   4.388  -0.221  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.726   3.913   1.469  1.00  0.00           H  
HETATM   36  H17 UNL     1      -3.266   3.255  -1.080  1.00  0.00           H  
HETATM   37  H18 UNL     1      -3.884   3.890   0.471  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.427   2.164   0.397  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   25   26
CONECT    7    8   15   27
CONECT    8    9
CONECT    9   10   10   11   13
CONECT   11   12
CONECT   12   28   29   30
CONECT   13   14
CONECT   14   31   32   33
CONECT   15   16   16   17
CONECT   17   18
CONECT   18   19   34   35
CONECT   19   36   37   38
END

HMDB0014910
     RDKit          3D
Malathion
 38 37  0  0  0  0  0  0  0  0999 V2000
   -3.9636   -2.6774    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8521   -2.9710   -0.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6100   -2.4149   -0.2114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320   -1.0351   -0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4177   -0.3103   -0.3220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1556   -0.4082    0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3828    0.5822   -0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366    1.2272    0.0058 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305   -0.2276    0.1556 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.3752   -0.3804   -1.2555 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4848    0.2738    1.4114 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0537    1.5104    1.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8357   -1.7376    0.6161 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3136   -2.7309   -0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720    1.7085   -0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1376    2.0310   -1.8565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8609    2.4482    0.3448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392    3.5392    0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1483    3.1748    0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7048   -3.5304    0.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6321   -2.7466    1.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5133   -1.7590    0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8035   -4.0399   -0.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1188   -2.4600   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5621   -1.2328    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995    0.0851    1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224    0.1253   -1.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1898    2.1549    0.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6747    1.3668    0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5800    1.9604    1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7338   -3.6572   -0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3780   -2.9856   -0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2013   -2.4934   -1.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3909    4.3883   -0.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7258    3.9134    1.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662    3.2552   -1.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8842    3.8895    0.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4268    2.1637    0.3968 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  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
  9 13  1  0
 13 14  1  0
  7 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ovide	Kegg
[(Dimethoxyphosphinothioyl)thio]butanedioic acid diethyl ester	HMDB
Carbophos	HMDB
Diethyl (dimethoxyphosphinothioylthio)succinate	HMDB
Karbofos	HMDB
Maldison	HMDB
Mercaptothion	HMDB
O,O-Dimethyl S-(1,2-bis(ethoxycarbonyl)ethyl)	HMDB
O,O-Dimethyl S-(1,2-dicarbethoxyethyl) dithiophosphate	HMDB
O,O-Dimethyl S-(1,2-dicarbethoxyethyl)phosphorodithioate	HMDB
O,O-Dimethyl S-1,2-di(ethoxycarbamyl)ethyl	HMDB
O,O-Dimethyldithiophosphate diethylmercaptosuccinate	HMDB
[(Dimethoxyphosphinothioyl)thio]butanedioate diethyl ester	HMDB
Diethyl (dimethoxyphosphinothioylthio)succinic acid	HMDB
O,O-Dimethyl S-(1,2-dicarbethoxyethyl) dithiophosphoric acid	HMDB
O,O-Dimethyl S-(1,2-dicarbethoxyethyl)phosphorodithioic acid	HMDB
O,O-Dimethyldithiophosphoric acid diethylmercaptosuccinic acid	HMDB
Carbofos	HMDB
Compound 4049	HMDB
Experimental insecticide 4049	HMDB
Insecticide no. 4049	HMDB
Malathione	HMDB
Mercaptosuccinic acid diethyl ester	HMDB
Mercaptotion	HMDB
MLT	HMDB
Oleophosphothion	HMDB
Sadophos	HMDB
Cythion	HMDB
Carbafos	HMDB
Prioderm	HMDB

Chemical Formula

C₁₀H₁₉O₆PS₂

Average Molecular Weight

330.358

Monoisotopic Molecular Weight

330.036066232

IUPAC Name

1,4-diethyl 2-{[dimethoxy(sulfanylidene)-lambda5-phosphanyl]sulfanyl}butanedioate

Traditional Name

1,4-diethyl 2-{[dimethoxy(sulfanylidene)-lambda5-phosphanyl]sulfanyl}butanedioate

CAS Registry Number

121-75-5

SMILES

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

InChI Identifier

InChI=1S/C10H19O6PS2/c1-5-15-9(11)7-8(10(12)16-6-2)19-17(18,13-3)14-4/h8H,5-7H2,1-4H3

InChI Key

JXSJBGJIGXNWCI-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ethyl ester (CHEBI:6651 )
diester (CHEBI:6651 )
organic thiophosphate (CHEBI:6651 )
carboxyalkyl phosphate (CHEBI:6651 )
Organophosphorus insecticides (C07497 )
a small molecule (CPD-13116 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

EC 3.1.1.8 (cholinesterase) inhibitor (HMDB: HMDB0014910)
EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0014910)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	2.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.16 g/L	Not Available
LogP	2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	165.9	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	2.67	ALOGPS
logP	1.86	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	78.18 m³·mol⁻¹	ChemAxon
Polarizability	31.66 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]+	175.081	31661259
DarkChem	[M-H]-	169.77	31661259
DeepCCS	[M+H]+	165.193	30932474
DeepCCS	[M-H]-	162.835	30932474
DeepCCS	[M-2H]-	195.999	30932474
DeepCCS	[M+Na]+	171.286	30932474
AllCCS	[M+H]+	165.5	32859911
AllCCS	[M+H-H2O]+	163.2	32859911
AllCCS	[M+NH4]+	167.6	32859911
AllCCS	[M+Na]+	168.2	32859911
AllCCS	[M-H]-	166.9	32859911
AllCCS	[M+Na-2H]-	167.7	32859911
AllCCS	[M+HCOO]-	168.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Malathion	CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC	2853.5	Standard polar	33892256
Malathion	CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC	1963.3	Standard non polar	33892256
Malathion	CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC	2058.4	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 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6s-5491000000-3592a22f2b1b3d40e724	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malathion GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malathion GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-8900000000-c6bc16fae6e217410d40	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion 10V, Positive-QTOF	splash10-0532-0192000000-80a735602f43e69672f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion 20V, Positive-QTOF	splash10-052b-5290000000-5faa1d20fccf211cb57f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion 40V, Positive-QTOF	splash10-001i-1910000000-a05ceb6094ed350bc453	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion 10V, Negative-QTOF	splash10-0faj-1193000000-b338e42eda1d6c05c7bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion 20V, Negative-QTOF	splash10-0006-1091000000-f5d217b3c309d0fbe4b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion 40V, Negative-QTOF	splash10-00fr-2390000000-b3ee35aea6b6f4b408a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion 10V, Positive-QTOF	splash10-00b9-0901000000-8e0175da8dcd3d5c20f6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion 20V, Positive-QTOF	splash10-004i-0900000000-1e03cd94309b778f8fd8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion 40V, Positive-QTOF	splash10-00b9-2900000000-49adc13defccdec4c850	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion 10V, Negative-QTOF	splash10-00di-0901000000-6de30c8781d1a5a9985a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion 20V, Negative-QTOF	splash10-00di-1900000000-5e2663e1be7df3418ce5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malathion 40V, Negative-QTOF	splash10-00di-0900000000-93b6b347a6b79a7090e5	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Taking drug identified by DrugBank entry DB00772	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00772	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00772

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3864

KEGG Compound ID

C07497

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Malathion

METLIN ID

Not Available

PubChem Compound

4004

PDB ID

Not Available

ChEBI ID

141474

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

Baker EL Jr, Warren M, Zack M, Dobbin RD, Miles JW, Miller S, Alderman L, Teeters WR: Epidemic malathion poisoning in Pakistan malaria workers. Lancet. 1978 Jan 7;1(8054):31-4. [PubMed:74508 ]
Edwards JW, Lee SG, Heath LM, Pisaniello DL: Worker exposure and a risk assessment of malathion and fenthion used in the control of Mediterranean fruit fly in South Australia. Environ Res. 2007 Jan;103(1):38-45. Epub 2006 Aug 17. [PubMed:16914134 ]
Bonner MR, Coble J, Blair A, Beane Freeman LE, Hoppin JA, Sandler DP, Alavanja MC: Malathion exposure and the incidence of cancer in the agricultural health study. Am J Epidemiol. 2007 Nov 1;166(9):1023-34. Epub 2007 Aug 23. [PubMed:17720683 ]
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.

Enzymes

Enzyme Details

1. Cholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Molecular weight:: 68417.575

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Ramos ZR, Fortunato JJ, Agostinho FR, Martins MR, Correa M, Schetinger MR, Dal-Pizzol F, Quevedo J: Influence of malathion on acetylcholinesterase activity in rats submitted to a forced swimming test. Neurotox Res. 2006 Jun;9(4):285-90. [PubMed:16782587 ]
Ahmed M, Rocha JB, Mazzanti CM, Morsch AL, Cargnelutti D, Correa M, Loro V, Morsch VM, Schetinger MR: Malathion, carbofuran and paraquat inhibit Bungarus sindanus (krait) venom acetylcholinesterase and human serum butyrylcholinesterase in vitro. Ecotoxicology. 2007 May;16(4):363-9. Epub 2007 Mar 16. [PubMed:17364237 ]
da Silva AP, Meotti FC, Santos AR, Farina M: Lactational exposure to malathion inhibits brain acetylcholinesterase in mice. Neurotoxicology. 2006 Dec;27(6):1101-5. Epub 2006 Apr 28. [PubMed:16716398 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

2. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Malathion (HMDB0014910)

MOL for HMDB0014910 (Malathion)

3D MOL for HMDB0014910 (Malathion)

3D SDF for HMDB0014910 (Malathion)

3D-SDF for HMDB0014910 (Malathion)

PDB for HMDB0014910 (Malathion)

3D PDB for HMDB0014910 (Malathion)

SMILES for HMDB0014910 (Malathion)

INCHI for HMDB0014910 (Malathion)

Structure for HMDB0014910 (Malathion)

3D Structure for HMDB0014910 (Malathion)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References