Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:31:05 UTC

Update Date

2021-09-26 23:01:58 UTC

HMDB ID

HMDB0250488

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Coumaphos

Description

Coumaphos, also known as meldane or asuntol, belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Based on a literature review a significant number of articles have been published on Coumaphos. This compound has been identified in human blood as reported by (PMID: 31557052 ). Coumaphos is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Coumaphos is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0250488
     RDKit          3D
Coumaphos
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.0733   -3.3076    1.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5157   -2.0029    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1549   -0.9701    1.2150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5459    0.5406    0.6965 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.1480    1.4377    2.0916 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8343    1.3557   -0.0843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2512    2.4415   -0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2691    3.2583   -1.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3283    0.2977   -0.3884 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0018    0.1487   -0.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7677   -0.0453   -1.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1306   -0.2055   -1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7973   -0.1803   -0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1646   -0.3364   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9698   -0.5406   -1.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7860   -0.3029    1.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5126   -0.4930    1.3797 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9845   -0.1084    2.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4804   -0.0679    3.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6828    0.0390    2.1662 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673    0.0100    0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873    0.1715    0.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4306   -3.2039    2.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3175   -4.1288    1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080   -3.5937    0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4102   -2.0044    0.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -1.8228   -0.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4524    2.0642   -1.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7147    3.1140   -0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117    3.5887   -2.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2048    2.6984   -1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5175    4.1520   -0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884   -0.0735   -2.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350   -0.3578   -2.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8628    0.3308   -1.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5095   -1.4029   -1.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0068   -0.8180   -1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1279    0.3178    1.8295 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
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 10  1  0
 21 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 11 33  1  0
 12 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 22 38  1  0
M  END


  Mrv1652307282022232D          

 22 23  0  0  0  0            999 V2000
   -2.0625   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -3.1895    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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 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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  7  6  2  0  0  0  0
  9  3  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  2  0  0  0  0
 13  9  2  0  0  0  0
 14 13  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17  4  1  0  0  0  0
 18  5  1  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
 20 10  1  0  0  0  0
 21 17  1  0  0  0  0
 21 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250488

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOP(=S)(OCC)OC1=CC2=C(C=C1)C(C)=C(Cl)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C14H16ClO5PS/c1-4-17-21(22,18-5-2)20-10-6-7-11-9(3)13(15)14(16)19-12(11)8-10/h6-8H,4-5H2,1-3H3

> <INCHI_KEY>
BXNANOICGRISHX-UHFFFAOYSA-N

> <FORMULA>
C14H16ClO5PS

> <MOLECULAR_WEIGHT>
362.766

> <EXACT_MASS>
362.014458531

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
34.607097180215796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
O-3-chloro-4-methyl-2-oxo-2H-chromen-7-yl O,O-diethyl phosphorothioate

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
4.1455163420000005

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.3375432749527505

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
89.92840000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
meldane

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250488
     RDKit          3D
Coumaphos
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.0733   -3.3076    1.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5157   -2.0029    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1549   -0.9701    1.2150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5459    0.5406    0.6965 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.1480    1.4377    2.0916 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8343    1.3557   -0.0843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2512    2.4415   -0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2691    3.2583   -1.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3283    0.2977   -0.3884 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0018    0.1487   -0.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7677   -0.0453   -1.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1306   -0.2055   -1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7973   -0.1803   -0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1646   -0.3364   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9698   -0.5406   -1.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7860   -0.3029    1.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5126   -0.4930    1.3797 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9845   -0.1084    2.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4804   -0.0679    3.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6828    0.0390    2.1662 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673    0.0100    0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873    0.1715    0.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4306   -3.2039    2.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3175   -4.1288    1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080   -3.5937    0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4102   -2.0044    0.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -1.8228   -0.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4524    2.0642   -1.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7147    3.1140   -0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117    3.5887   -2.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2048    2.6984   -1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5175    4.1520   -0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884   -0.0735   -2.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350   -0.3578   -2.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8628    0.3308   -1.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5095   -1.4029   -1.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0068   -0.8180   -1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1279    0.3178    1.8295 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
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 10  1  0
 21 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 11 33  1  0
 12 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 22 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      -3.850  -3.286   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850  -5.954   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.310  -3.286   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310  -5.954   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       8.002   0.000   0.000  0.00  0.00          Cl+0
HETATM   16  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.540  -4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.540  -4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   21  P   UNK     0       0.000  -4.620   0.000  0.00  0.00           P+0
HETATM   22  S   UNK     0       0.000  -6.160   0.000  0.00  0.00           S+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    9                                                            
CONECT    4    1   17                                                       
CONECT    5    2   18                                                       
CONECT    6    7   10                                                       
CONECT    7    6   11                                                       
CONECT    8   10   12                                                       
CONECT    9    3   11   13                                                  
CONECT   10    6    8   20                                                  
CONECT   11    7    9   12                                                  
CONECT   12    8   11   19                                                  
CONECT   13    9   14   15                                                  
CONECT   14   13   16   19                                                  
CONECT   15   13                                                            
CONECT   16   14                                                            
CONECT   17    4   21                                                       
CONECT   18    5   21                                                       
CONECT   19   12   14                                                       
CONECT   20   10   21                                                       
CONECT   21   17   18   20   22                                             
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0250488
HETATM    1  C1  UNL     1      -3.073  -3.308   1.017  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.516  -2.003   0.539  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.155  -0.970   1.215  1.00  0.00           O  
HETATM    4  P1  UNL     1      -2.546   0.541   0.696  1.00  0.00           P  
HETATM    5  S1  UNL     1      -2.148   1.438   2.092  1.00  0.00           S  
HETATM    6  O2  UNL     1      -3.834   1.356  -0.084  1.00  0.00           O  
HETATM    7  C3  UNL     1      -3.251   2.442  -0.764  1.00  0.00           C  
HETATM    8  C4  UNL     1      -4.269   3.258  -1.503  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.328   0.298  -0.388  1.00  0.00           O  
HETATM   10  C5  UNL     1       0.002   0.149  -0.257  1.00  0.00           C  
HETATM   11  C6  UNL     1       0.768  -0.045  -1.405  1.00  0.00           C  
HETATM   12  C7  UNL     1       2.131  -0.206  -1.356  1.00  0.00           C  
HETATM   13  C8  UNL     1       2.797  -0.180  -0.159  1.00  0.00           C  
HETATM   14  C9  UNL     1       4.165  -0.336  -0.057  1.00  0.00           C  
HETATM   15  C10 UNL     1       4.970  -0.541  -1.267  1.00  0.00           C  
HETATM   16  C11 UNL     1       4.786  -0.303   1.172  1.00  0.00           C  
HETATM   17 CL1  UNL     1       6.513  -0.493   1.380  1.00  0.00          CL  
HETATM   18  C12 UNL     1       3.984  -0.108   2.278  1.00  0.00           C  
HETATM   19  O4  UNL     1       4.480  -0.068   3.413  1.00  0.00           O  
HETATM   20  O5  UNL     1       2.683   0.039   2.166  1.00  0.00           O  
HETATM   21  C13 UNL     1       2.067   0.010   0.997  1.00  0.00           C  
HETATM   22  C14 UNL     1       0.687   0.171   0.938  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.431  -3.204   2.057  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.318  -4.129   1.033  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.908  -3.594   0.333  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.410  -2.004   0.715  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.675  -1.823  -0.549  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.452   2.064  -1.466  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.715   3.114  -0.063  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.812   3.589  -2.466  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.205   2.698  -1.711  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.517   4.152  -0.932  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.288  -0.073  -2.379  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.735  -0.358  -2.254  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.863   0.331  -1.930  1.00  0.00           H  
HETATM   36  H14 UNL     1       4.510  -1.403  -1.831  1.00  0.00           H  
HETATM   37  H15 UNL     1       6.007  -0.818  -1.049  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.128   0.318   1.829  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4
CONECT    4    5    5    6    9
CONECT    6    7
CONECT    7    8   28   29
CONECT    8   30   31   32
CONECT    9   10
CONECT   10   11   11   22
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   14   21
CONECT   14   15   16   16
CONECT   15   35   36   37
CONECT   16   17   18
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   22
CONECT   22   38
END

HMDB0250488
     RDKit          3D
Coumaphos
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.0733   -3.3076    1.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5157   -2.0029    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1549   -0.9701    1.2150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5459    0.5406    0.6965 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.1480    1.4377    2.0916 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8343    1.3557   -0.0843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2512    2.4415   -0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2691    3.2583   -1.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3283    0.2977   -0.3884 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0018    0.1487   -0.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7677   -0.0453   -1.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1306   -0.2055   -1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7973   -0.1803   -0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1646   -0.3364   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9698   -0.5406   -1.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7860   -0.3029    1.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5126   -0.4930    1.3797 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9845   -0.1084    2.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4804   -0.0679    3.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6828    0.0390    2.1662 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673    0.0100    0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873    0.1715    0.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4306   -3.2039    2.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3175   -4.1288    1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080   -3.5937    0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4102   -2.0044    0.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -1.8228   -0.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4524    2.0642   -1.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7147    3.1140   -0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117    3.5887   -2.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2048    2.6984   -1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5175    4.1520   -0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884   -0.0735   -2.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350   -0.3578   -2.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8628    0.3308   -1.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5095   -1.4029   -1.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0068   -0.8180   -1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1279    0.3178    1.8295 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
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 10  1  0
 21 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 11 33  1  0
 12 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Chloro-4-methyl-7-coumarinyl diethyl phosphorothioate	ChEBI
3-Chloro-4-methyl-7-hydroxycoumarin diethyl thiophosphoric acid ester	ChEBI
3-Chloro-7-diethoxyphosphinothioyloxy-4-methylcoumarin	ChEBI
3-Chloro-7-hydroxy-4-methyl-coumarin O,O-diethyl phosphorothioate	ChEBI
O,O-Diethyl 3-chloro-4-methyl-7-umbelliferone thiophosphate	ChEBI
O,O-Diethyl O-(3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl)phosphorothioate	ChEBI
O-(3-Chloro-4-methyl-2-oxo-2H-chromen-7-yl) O,O-diethyl thiophosphate	ChEBI
Phosphorothioic acid, O-(3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl) O,O-diethyl ester	ChEBI
Meldane	Kegg
3-Chloro-4-methyl-7-coumarinyl diethyl phosphorothioic acid	Generator
3-Chloro-4-methyl-7-hydroxycoumarin diethyl thiophosphate ester	Generator
3-Chloro-7-hydroxy-4-methyl-coumarin O,O-diethyl phosphorothioic acid	Generator
O,O-Diethyl 3-chloro-4-methyl-7-umbelliferone thiophosphoric acid	Generator
O,O-Diethyl O-(3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl)phosphorothioic acid	Generator
O-(3-Chloro-4-methyl-2-oxo-2H-chromen-7-yl) O,O-diethyl thiophosphoric acid	Generator
Phosphorothioate, O-(3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl) O,O-diethyl ester	Generator
Asuntol	MeSH
Coumafos	MeSH

Chemical Formula

C₁₄H₁₆ClO₅PS

Average Molecular Weight

362.766

Monoisotopic Molecular Weight

362.014458531

IUPAC Name

O-3-chloro-4-methyl-2-oxo-2H-chromen-7-yl O,O-diethyl phosphorothioate

Traditional Name

meldane

CAS Registry Number

Not Available

SMILES

CCOP(=S)(OCC)OC1=CC2=C(C=C1)C(C)=C(Cl)C(=O)O2

InChI Identifier

InChI=1S/C14H16ClO5PS/c1-4-17-21(22,18-5-2)20-10-6-7-11-9(3)13(15)14(16)19-12(11)8-10/h6-8H,4-5H2,1-3H3

InChI Key

BXNANOICGRISHX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Aryl thiophosphate
Benzopyran
1-benzopyran
Thiophosphate triester
Pyranone
Aryl chloride
Aryl halide
Thiophosphoric acid ester
Benzenoid
Organic thiophosphoric acid or derivatives
Pyran
Heteroaromatic compound
Lactone
Organoheterocyclic compound
Oxacycle
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:3903 )
organic thiophosphate (CHEBI:3903 )
organothiophosphate insecticide (CHEBI:3903 )
Acaricides (C11025 )
a small molecule (CPD-8964 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0250488)
Cell surface (HMDB: HMDB0250488)

Tissue substructure

Nerve (HMDB: HMDB0250488)

Source

Exogenous

Exogenous (HMDB: HMDB0250488)

Process

Naturally occurring process

Biological process

Tetracyclines (HMDB: HMDB0250488)

Role

Industrial application

Agrochemical (HMDB: HMDB0250488)

Agriculture

Pesticide

Acaricide (HMDB: HMDB0250488)
Avicide (HMDB: HMDB0250488)

Pharmaceutical industry

Antinematodal drug (HMDB: HMDB0250488)

Biological role

Modulator

Inhibitor

EC 3.1.1.8 (cholinesterase) inhibitor (HMDB: HMDB0250488)

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
logP	4.5	ALOGPS
logP	4.15	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	89.93 m³·mol⁻¹	ChemAxon
Polarizability	34.61 Å³	ChemAxon
Number of Rings	2	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
DeepCCS	[M+H]+	172.109	30932474
DeepCCS	[M-H]-	169.751	30932474
DeepCCS	[M-2H]-	203.021	30932474
DeepCCS	[M+Na]+	178.249	30932474
AllCCS	[M+H]+	175.5	32859911
AllCCS	[M+H-H2O]+	172.6	32859911
AllCCS	[M+NH4]+	178.0	32859911
AllCCS	[M+Na]+	178.8	32859911
AllCCS	[M-H]-	172.1	32859911
AllCCS	[M+Na-2H]-	171.7	32859911
AllCCS	[M+HCOO]-	171.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	21.5349 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.55 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2905.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	778.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	283.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	479.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	897.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	850.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	144.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1825.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	653.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1943.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	670.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	468.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	584.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	564.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	20.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Coumaphos	CCOP(=S)(OCC)OC1=CC2=C(C=C1)C(C)=C(Cl)C(=O)O2	3508.1	Standard polar	33892256
Coumaphos	CCOP(=S)(OCC)OC1=CC2=C(C=C1)C(C)=C(Cl)C(=O)O2	2644.8	Standard non polar	33892256
Coumaphos	CCOP(=S)(OCC)OC1=CC2=C(C=C1)C(C)=C(Cl)C(=O)O2	2658.6	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 - Coumaphos GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2020-08-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumaphos GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-06vj-7954000000-80e126f971975f223e60	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos LC-ESI-QTOF , positive-QTOF	splash10-03di-0009000000-1eb96120bb8c3511912e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos LC-ESI-QTOF , positive-QTOF	splash10-0bw9-0039000000-13c6f9257fbc11ac5878	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos LC-ESI-QTOF , positive-QTOF	splash10-004i-0091000000-5f535054f0f4f1d40167	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos LC-ESI-QTOF , positive-QTOF	splash10-004i-0090000000-c875939d86ddad0a8e08	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos LC-ESI-QTOF , positive-QTOF	splash10-004i-0590000000-878fbf88eb9b1468b002	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos 50V, Positive-QTOF	splash10-004i-0590000000-878fbf88eb9b1468b002	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos 60V, Positive-QTOF	splash10-002b-6690000000-0b075949b4fc64417b45	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos 75V, Positive-QTOF	splash10-002b-3930000000-afb7f841e4d8f9374a10	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos 60V, Positive-QTOF	splash10-004j-6690000000-e4dbfc7cf2aa396974cb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos 40V, Positive-QTOF	splash10-004i-0090000000-05ecad535abaa608b26f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos 90V, Positive-QTOF	splash10-0002-5900000000-87869720e427b6ae2f4d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos 30V, Positive-QTOF	splash10-004i-0091000000-fa3c3a4750e37d943301	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos 50V, Positive-QTOF	splash10-004i-0590000000-89c84cbf0e4cff0420d3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos 15V, Positive-QTOF	splash10-03di-0209000000-b115f399660285d47a7c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos 45V, Positive-QTOF	splash10-0002-7491000000-17d6540e989451a469d4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos 30V, Positive-QTOF	splash10-056r-1396000000-1b6df76eac4b3635ae59	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos 20V, Positive-QTOF	splash10-0bw9-0039000000-13c6f9257fbc11ac5878	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos 30V, Positive-QTOF	splash10-004i-0091000000-6939f400c7b0e0135314	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumaphos 10V, Positive-QTOF	splash10-03di-0009000000-5fe0783ca5e8f6cf5a52	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaphos 10V, Positive-QTOF	splash10-03e9-0009000000-803a80ca33dda23dc6aa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaphos 20V, Positive-QTOF	splash10-0bu0-1129000000-00264c0e462527baf311	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaphos 40V, Positive-QTOF	splash10-0hkm-4940000000-213ceacd491055ba0ef5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaphos 10V, Negative-QTOF	splash10-03e9-0129000000-a5bf355fe65815e55f3f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaphos 20V, Negative-QTOF	splash10-01q9-0229000000-ba2d0f5d2138ff62e801	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaphos 40V, Negative-QTOF	splash10-0k9i-0968000000-a999b49b42dee23cdc87	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB11390

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2768

KEGG Compound ID

C11025

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Coumaphos

METLIN ID

Not Available

PubChem Compound

2871

PDB ID

Not Available

ChEBI ID

3903

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1354341

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Coumaphos (HMDB0250488)

MOL for HMDB0250488 (Coumaphos)

3D MOL for HMDB0250488 (Coumaphos)

3D SDF for HMDB0250488 (Coumaphos)

3D-SDF for HMDB0250488 (Coumaphos)

PDB for HMDB0250488 (Coumaphos)

3D PDB for HMDB0250488 (Coumaphos)

SMILES for HMDB0250488 (Coumaphos)

INCHI for HMDB0250488 (Coumaphos)

Structure for HMDB0250488 (Coumaphos)

3D Structure for HMDB0250488 (Coumaphos)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra