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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:30:52 UTC

Update Date

2021-09-26 23:01:57 UTC

HMDB ID

HMDB0250485

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Coumachlor

Description

COUMACHLOR belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton. Based on a literature review very few articles have been published on COUMACHLOR. This compound has been identified in human blood as reported by (PMID: 31557052 ). Coumachlor is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Coumachlor 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

HMDB0250485
     RDKit          3D
Coumachlor
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.7218    3.4581   -0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5826    2.5696   -0.8091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8889    2.9042   -1.9282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0573    1.2975   -0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4100    0.0955   -0.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9400   -1.1467   -0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8925   -2.3135   -1.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3868   -3.4884   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9331   -3.5499    0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5331   -5.0974    1.2696 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917   -2.4124    1.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4895   -1.2099    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0643    0.1342   -0.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417    0.2387    0.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0649    0.3048    1.5326 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267    0.2778    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8899    0.3815    1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2815    0.4190    1.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9550    0.3520    0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2014    0.2485   -0.8539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8183    0.2091   -0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160    0.1123   -1.9461 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103    0.0719   -2.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2623   -0.0259   -3.1658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2236    2.9360    0.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220    4.3259    0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0310    3.9222   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1615    1.1514   -0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9067    1.3016    0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6845    0.1113   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4539   -2.2445   -2.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3342   -4.4023   -1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4280   -2.4645    2.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771   -0.3623    1.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5108    0.3784    2.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4164    0.4391    2.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8479    0.5016    2.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0423    0.3804    0.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7382    0.1951   -1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 12  6  1  0
 23 13  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  8 32  1  0
 11 33  1  0
 12 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
M  END

  Mrv1572004221604122D          

 24 26  0  0  0  0            999 V2000
    5.0013   -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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    4.2868   -0.0000    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
    2.8579    2.4750    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 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
    1.4289   -0.0000    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
    2.8579    3.3000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 11  1  1  0  0  0  0
 11 10  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14  4  2  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16  5  2  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 14  1  0  0  0  0
 18 17  2  0  0  0  0
 19 17  1  0  0  0  0
 20 13  1  0  0  0  0
 21 11  2  0  0  0  0
 22 18  1  0  0  0  0
 23 19  2  0  0  0  0
 24 16  1  0  0  0  0
 24 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250485

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CC(C1=CC=C(Cl)C=C1)C1=C(O)C2=CC=CC=C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H15ClO4/c1-11(21)10-15(12-6-8-13(20)9-7-12)17-18(22)14-4-2-3-5-16(14)24-19(17)23/h2-9,15,22H,10H2,1H3

> <INCHI_KEY>
DEKWZWCFHUABHE-UHFFFAOYSA-N

> <FORMULA>
C19H15ClO4

> <MOLECULAR_WEIGHT>
342.78

> <EXACT_MASS>
342.0658867

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
34.389409263192405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[1-(4-chlorophenyl)-3-oxobutyl]-4-hydroxy-2H-chromen-2-one

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
3.3487520386666665

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.420511767357727

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.150478581374987

> <JCHEM_PKA_STRONGEST_BASIC>
-6.903837419052209

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
91.66489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
coumachlor

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250485
     RDKit          3D
Coumachlor
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.7218    3.4581   -0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5826    2.5696   -0.8091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8889    2.9042   -1.9282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0573    1.2975   -0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4100    0.0955   -0.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9400   -1.1467   -0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8925   -2.3135   -1.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3868   -3.4884   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9331   -3.5499    0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5331   -5.0974    1.2696 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917   -2.4124    1.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4895   -1.2099    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0643    0.1342   -0.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417    0.2387    0.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0649    0.3048    1.5326 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267    0.2778    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8899    0.3815    1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2815    0.4190    1.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9550    0.3520    0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2014    0.2485   -0.8539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8183    0.2091   -0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160    0.1123   -1.9461 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103    0.0719   -2.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2623   -0.0259   -3.1658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2236    2.9360    0.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220    4.3259    0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0310    3.9222   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1615    1.1514   -0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9067    1.3016    0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6845    0.1113   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4539   -2.2445   -2.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3342   -4.4023   -1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4280   -2.4645    2.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771   -0.3623    1.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5108    0.3784    2.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4164    0.4391    2.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8479    0.5016    2.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0423    0.3804    0.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7382    0.1951   -1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 12  6  1  0
 23 13  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  8 32  1  0
 11 33  1  0
 12 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0       5.335   6.160   0.000  0.00  0.00          Cl+0
HETATM   21  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   14                                                       
CONECT    5    3   16                                                       
CONECT    6    8   12                                                       
CONECT    7    9   12                                                       
CONECT    8    6   13                                                       
CONECT    9    7   13                                                       
CONECT   10   11   15                                                       
CONECT   11    1   10   21                                                  
CONECT   12    6    7   15                                                  
CONECT   13    8    9   20                                                  
CONECT   14    4   16   18                                                  
CONECT   15   10   12   17                                                  
CONECT   16    5   14   24                                                  
CONECT   17   15   18   19                                                  
CONECT   18   14   17   22                                                  
CONECT   19   17   23   24                                                  
CONECT   20   13                                                            
CONECT   21   11                                                            
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24   16   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0250485
HETATM    1  C1  UNL     1      -0.722   3.458  -0.004  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.583   2.570  -0.809  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.889   2.904  -1.928  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.057   1.297  -0.254  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.410   0.095  -0.896  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.940  -1.147  -0.305  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.892  -2.314  -1.051  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.387  -3.488  -0.534  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.933  -3.550   0.711  1.00  0.00           C  
HETATM   10 CL1  UNL     1      -3.533  -5.097   1.270  1.00  0.00          CL  
HETATM   11  C9  UNL     1      -2.992  -2.412   1.467  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.489  -1.210   0.946  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.064   0.134  -0.862  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.742   0.239   0.339  1.00  0.00           C  
HETATM   15  O2  UNL     1       0.065   0.305   1.533  1.00  0.00           O  
HETATM   16  C13 UNL     1       2.127   0.278   0.356  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.890   0.381   1.497  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.281   0.419   1.475  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.955   0.352   0.288  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.201   0.249  -0.854  1.00  0.00           C  
HETATM   21  C18 UNL     1       2.818   0.209  -0.865  1.00  0.00           C  
HETATM   22  O3  UNL     1       2.116   0.112  -1.946  1.00  0.00           O  
HETATM   23  C19 UNL     1       0.810   0.072  -2.014  1.00  0.00           C  
HETATM   24  O4  UNL     1       0.262  -0.026  -3.166  1.00  0.00           O  
HETATM   25  H1  UNL     1      -0.224   2.936   0.841  1.00  0.00           H  
HETATM   26  H2  UNL     1      -1.322   4.326   0.387  1.00  0.00           H  
HETATM   27  H3  UNL     1       0.031   3.922  -0.698  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.161   1.151  -0.395  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.907   1.302   0.842  1.00  0.00           H  
HETATM   30  H6  UNL     1      -1.684   0.111  -2.008  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.454  -2.244  -2.040  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.334  -4.402  -1.149  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.428  -2.464   2.456  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.577  -0.362   1.606  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.511   0.378   2.410  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.416   0.439   2.459  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.848   0.502   2.405  1.00  0.00           H  
HETATM   38  H14 UNL     1       6.042   0.380   0.284  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.738   0.195  -1.795  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5   28   29
CONECT    5    6   13   30
CONECT    6    7    7   12
CONECT    7    8   31
CONECT    8    9    9   32
CONECT    9   10   11
CONECT   11   12   12   33
CONECT   12   34
CONECT   13   14   14   23
CONECT   14   15   16
CONECT   15   35
CONECT   16   17   17   21
CONECT   17   18   36
CONECT   18   19   19   37
CONECT   19   20   38
CONECT   20   21   21   39
CONECT   21   22
CONECT   22   23
CONECT   23   24   24
END

HMDB0250485
     RDKit          3D
Coumachlor
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.7218    3.4581   -0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5826    2.5696   -0.8091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8889    2.9042   -1.9282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0573    1.2975   -0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4100    0.0955   -0.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9400   -1.1467   -0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8925   -2.3135   -1.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3868   -3.4884   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9331   -3.5499    0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5331   -5.0974    1.2696 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917   -2.4124    1.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4895   -1.2099    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0643    0.1342   -0.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417    0.2387    0.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0649    0.3048    1.5326 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267    0.2778    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8899    0.3815    1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2815    0.4190    1.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9550    0.3520    0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2014    0.2485   -0.8539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8183    0.2091   -0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160    0.1123   -1.9461 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103    0.0719   -2.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2623   -0.0259   -3.1658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2236    2.9360    0.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220    4.3259    0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0310    3.9222   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1615    1.1514   -0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9067    1.3016    0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6845    0.1113   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4539   -2.2445   -2.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3342   -4.4023   -1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4280   -2.4645    2.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771   -0.3623    1.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5108    0.3784    2.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4164    0.4391    2.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8479    0.5016    2.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0423    0.3804    0.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7382    0.1951   -1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 12  6  1  0
 23 13  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  8 32  1  0
 11 33  1  0
 12 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(1-(4-Chlorophenyl)-3-oxobutyl)-4-hydroxy-2H-1-benzopyran-2-one	MeSH
3-(alpha-Acetonyl-p-chlorobenzyl)-4-hydroxycoumarin	MeSH
Coumachlor	MeSH

Chemical Formula

C₁₉H₁₅ClO₄

Average Molecular Weight

342.78

Monoisotopic Molecular Weight

342.0658867

IUPAC Name

3-[1-(4-chlorophenyl)-3-oxobutyl]-4-hydroxy-2H-chromen-2-one

Traditional Name

coumachlor

CAS Registry Number

Not Available

SMILES

CC(=O)CC(C1=CC=C(Cl)C=C1)C1=C(O)C2=CC=CC=C2OC1=O

InChI Identifier

InChI=1S/C19H15ClO4/c1-11(21)10-15(12-6-8-13(20)9-7-12)17-18(22)14-4-2-3-5-16(14)24-19(17)23/h2-9,15,22H,10H2,1H3

InChI Key

DEKWZWCFHUABHE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

4-hydroxycoumarins

Alternative Parents

Substituents

4-hydroxycoumarin
Benzopyran
1-benzopyran
Pyranone
Halobenzene
Chlorobenzene
Benzenoid
Pyran
Monocyclic benzene moiety
Aryl halide
Aryl chloride
Heteroaromatic compound
Vinylogous acid
Ketone
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organohalogen compound
Carbonyl group
Organochloride
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxycoumarin (CHEBI:80741 )
Coumarin rodenticides (C16805 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	3.13	ALOGPS
logP	3.35	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	5.15	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.66 m³·mol⁻¹	ChemAxon
Polarizability	34.39 Å³	ChemAxon
Number of Rings	3	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]+	177.984	30932474
DeepCCS	[M-H]-	175.626	30932474
DeepCCS	[M-2H]-	208.511	30932474
DeepCCS	[M+Na]+	184.077	30932474
AllCCS	[M+H]+	178.1	32859911
AllCCS	[M+H-H2O]+	174.8	32859911
AllCCS	[M+NH4]+	181.2	32859911
AllCCS	[M+Na]+	182.0	32859911
AllCCS	[M-H]-	179.3	32859911
AllCCS	[M+Na-2H]-	178.8	32859911
AllCCS	[M+HCOO]-	178.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Coumachlor	CC(=O)CC(C1=CC=C(Cl)C=C1)C1=C(O)C2=CC=CC=C2OC1=O	4112.9	Standard polar	33892256
Coumachlor	CC(=O)CC(C1=CC=C(Cl)C=C1)C1=C(O)C2=CC=CC=C2OC1=O	2097.8	Standard non polar	33892256
Coumachlor	CC(=O)CC(C1=CC=C(Cl)C=C1)C1=C(O)C2=CC=CC=C2OC1=O	2947.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Coumachlor,2TMS,isomer #1	CC(=CC(C1=CC=C(Cl)C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3000.4	Semi standard non polar	33892256
Coumachlor,2TMS,isomer #1	CC(=CC(C1=CC=C(Cl)C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2765.3	Standard non polar	33892256
Coumachlor,2TMS,isomer #1	CC(=CC(C1=CC=C(Cl)C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3376.4	Standard polar	33892256
Coumachlor,2TMS,isomer #2	C=C(CC(C1=CC=C(Cl)C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2949.1	Semi standard non polar	33892256
Coumachlor,2TMS,isomer #2	C=C(CC(C1=CC=C(Cl)C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2670.9	Standard non polar	33892256
Coumachlor,2TMS,isomer #2	C=C(CC(C1=CC=C(Cl)C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3380.2	Standard polar	33892256
Coumachlor,2TBDMS,isomer #1	CC(=CC(C1=CC=C(Cl)C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3499.8	Semi standard non polar	33892256
Coumachlor,2TBDMS,isomer #1	CC(=CC(C1=CC=C(Cl)C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3202.5	Standard non polar	33892256
Coumachlor,2TBDMS,isomer #1	CC(=CC(C1=CC=C(Cl)C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3545.9	Standard polar	33892256
Coumachlor,2TBDMS,isomer #2	C=C(CC(C1=CC=C(Cl)C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3447.2	Semi standard non polar	33892256
Coumachlor,2TBDMS,isomer #2	C=C(CC(C1=CC=C(Cl)C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3067.8	Standard non polar	33892256
Coumachlor,2TBDMS,isomer #2	C=C(CC(C1=CC=C(Cl)C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3551.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Coumachlor GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-5192000000-9b076b9c36a9a9fe568c	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumachlor GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumachlor GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumachlor GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumachlor GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumachlor GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumachlor GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumachlor GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	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 - Coumachlor 10V, Positive-QTOF	splash10-002f-0009000000-521e01b49a8a2e42f4e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumachlor 20V, Positive-QTOF	splash10-004l-0229000000-cdbafa11a378f9374ce1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumachlor 40V, Positive-QTOF	splash10-074u-3954000000-07bf27eed4485e9bbf07	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumachlor 10V, Negative-QTOF	splash10-0006-0129000000-b44a05dcec0ba2b69753	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumachlor 20V, Negative-QTOF	splash10-01oy-3659000000-eada5eaf63dc4890696c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumachlor 40V, Negative-QTOF	splash10-06tf-9541000000-fa32e4df97c43e7a5b9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumachlor 10V, Positive-QTOF	splash10-03dl-0936000000-3e6a79c8c8752b1a208f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumachlor 20V, Positive-QTOF	splash10-03dr-0960000000-033979711e97339da79b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumachlor 40V, Positive-QTOF	splash10-00di-3910000000-70ce76b9c0ca05ceb8bb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumachlor 10V, Negative-QTOF	splash10-0006-0209000000-62fe7ef21b565863c5ad	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumachlor 20V, Negative-QTOF	splash10-03di-2912000000-21b33b39c5a66b9d1b8a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumachlor 40V, Negative-QTOF	splash10-001l-9300000000-486cef7e360a503f8c44	2021-10-12	Wishart Lab	View Spectrum

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10443016

KEGG Compound ID

C16805

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54682651

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

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 Coumachlor (HMDB0250485)

MOL for HMDB0250485 (Coumachlor)

3D MOL for HMDB0250485 (Coumachlor)

3D SDF for HMDB0250485 (Coumachlor)

3D-SDF for HMDB0250485 (Coumachlor)

PDB for HMDB0250485 (Coumachlor)

3D PDB for HMDB0250485 (Coumachlor)

SMILES for HMDB0250485 (Coumachlor)

INCHI for HMDB0250485 (Coumachlor)

Structure for HMDB0250485 (Coumachlor)

3D Structure for HMDB0250485 (Coumachlor)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra