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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:19:56 UTC

Update Date

2021-09-26 23:05:01 UTC

HMDB ID

HMDB0252444

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Formetanate

Description

Formetanate, also known as dicarzol or formetanic acid, belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group. Formetanate is a very strong basic compound (based on its pKa). Formetanate is a potentially toxic compound. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. This compound has been identified in human blood as reported by (PMID: 31557052 ). Formetanate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Formetanate 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

HMDB0252444
     RDKit          3D
Formetanate
 31 31  0  0  0  0  0  0  0  0999 V2000
    5.9756    0.6994   -1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9415   -0.2802   -1.3635 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -0.2825   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6360    0.6148    0.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7573   -1.2176   -0.7445 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413   -1.1318    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5477   -1.7687    1.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4313   -1.6794    2.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6474   -0.9198    1.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -0.2593    0.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6945    0.5249    0.0560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8943    0.0332    0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0364    0.7535   -0.2333 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2788    0.0852   -0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9746    2.2149   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5480   -0.3706   -0.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3483    1.0338   -2.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5736    1.5535   -0.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8405    0.2816   -0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0224   -1.0416   -2.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3898   -2.3640    1.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3631   -2.1848    3.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5426   -0.8149    2.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0467   -0.9618    0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3674   -0.8235    0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2468   -0.3026   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1481    0.7508   -0.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0017    2.6390   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3997    2.4642   -1.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5269    2.6205    0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6102    0.1340   -1.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 13 14  1  0
 13 15  1  0
 10 16  2  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 12 24  1  0
 14 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
M  END


  Mrv0541 02241205012D          

 16 16  0  0  0  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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
    0.7145   -0.4125    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    0.8250    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 12 10  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252444

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC(=O)OC1=CC=CC(=C1)N=CN(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C11H15N3O2/c1-12-11(15)16-10-6-4-5-9(7-10)13-8-14(2)3/h4-8H,1-3H3,(H,12,15)

> <INCHI_KEY>
RMFNNCGOSPBBAD-UHFFFAOYSA-N

> <FORMULA>
C11H15N3O2

> <MOLECULAR_WEIGHT>
221.2557

> <EXACT_MASS>
221.116426739

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.003822644681666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(dimethylamino)methylidene]amino}phenyl N-methylcarbamate

> <ALOGPS_LOGP>
0.91

> <JCHEM_LOGP>
1.0769151696666668

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.771621613389783

> <JCHEM_PKA_STRONGEST_BASIC>
8.88855257730159

> <JCHEM_POLAR_SURFACE_AREA>
53.93

> <JCHEM_REFRACTIVITY>
63.618199999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
formetanate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252444
     RDKit          3D
Formetanate
 31 31  0  0  0  0  0  0  0  0999 V2000
    5.9756    0.6994   -1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9415   -0.2802   -1.3635 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -0.2825   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6360    0.6148    0.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7573   -1.2176   -0.7445 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413   -1.1318    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5477   -1.7687    1.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4313   -1.6794    2.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6474   -0.9198    1.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -0.2593    0.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6945    0.5249    0.0560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8943    0.0332    0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0364    0.7535   -0.2333 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2788    0.0852   -0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9746    2.2149   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5480   -0.3706   -0.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3483    1.0338   -2.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5736    1.5535   -0.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8405    0.2816   -0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0224   -1.0416   -2.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3898   -2.3640    1.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3631   -2.1848    3.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5426   -0.8149    2.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0467   -0.9618    0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3674   -0.8235    0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2468   -0.3026   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1481    0.7508   -0.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0017    2.6390   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3997    2.4642   -1.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5269    2.6205    0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6102    0.1340   -1.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 13 14  1  0
 13 15  1  0
 10 16  2  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 12 24  1  0
 14 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.667   6.160   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    6                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0252444
HETATM    1  C1  UNL     1       5.976   0.699  -1.177  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.942  -0.280  -1.363  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.767  -0.282  -0.581  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.636   0.615   0.309  1.00  0.00           O  
HETATM    5  O2  UNL     1       2.757  -1.218  -0.745  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.641  -1.132   0.077  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.548  -1.769   1.285  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.431  -1.679   2.101  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.647  -0.920   1.698  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.588  -0.259   0.477  1.00  0.00           C  
HETATM   11  N2  UNL     1      -1.694   0.525   0.056  1.00  0.00           N  
HETATM   12  C8  UNL     1      -2.894   0.033   0.164  1.00  0.00           C  
HETATM   13  N3  UNL     1      -4.036   0.754  -0.233  1.00  0.00           N  
HETATM   14  C9  UNL     1      -5.279   0.085  -0.547  1.00  0.00           C  
HETATM   15  C10 UNL     1      -3.975   2.215  -0.335  1.00  0.00           C  
HETATM   16  C11 UNL     1       0.548  -0.371  -0.316  1.00  0.00           C  
HETATM   17  H1  UNL     1       6.348   1.034  -2.187  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.574   1.553  -0.599  1.00  0.00           H  
HETATM   19  H3  UNL     1       6.841   0.282  -0.604  1.00  0.00           H  
HETATM   20  H4  UNL     1       5.022  -1.042  -2.099  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.390  -2.364   1.604  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.363  -2.185   3.054  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.543  -0.815   2.293  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.047  -0.962   0.571  1.00  0.00           H  
HETATM   25  H9  UNL     1      -5.367  -0.823   0.116  1.00  0.00           H  
HETATM   26  H10 UNL     1      -5.247  -0.303  -1.602  1.00  0.00           H  
HETATM   27  H11 UNL     1      -6.148   0.751  -0.427  1.00  0.00           H  
HETATM   28  H12 UNL     1      -5.002   2.639  -0.433  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.400   2.464  -1.233  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.527   2.620   0.586  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.610   0.134  -1.263  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7    7   16
CONECT    7    8   21
CONECT    8    9    9   22
CONECT    9   10   23
CONECT   10   11   16   16
CONECT   11   12   12
CONECT   12   13   24
CONECT   13   14   15
CONECT   14   25   26   27
CONECT   15   28   29   30
CONECT   16   31
END

HMDB0252444
     RDKit          3D
Formetanate
 31 31  0  0  0  0  0  0  0  0999 V2000
    5.9756    0.6994   -1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9415   -0.2802   -1.3635 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -0.2825   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6360    0.6148    0.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7573   -1.2176   -0.7445 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413   -1.1318    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5477   -1.7687    1.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4313   -1.6794    2.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6474   -0.9198    1.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -0.2593    0.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6945    0.5249    0.0560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8943    0.0332    0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0364    0.7535   -0.2333 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2788    0.0852   -0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9746    2.2149   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5480   -0.3706   -0.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3483    1.0338   -2.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5736    1.5535   -0.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8405    0.2816   -0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0224   -1.0416   -2.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3898   -2.3640    1.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3631   -2.1848    3.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5426   -0.8149    2.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0467   -0.9618    0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3674   -0.8235    0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2468   -0.3026   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1481    0.7508   -0.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0017    2.6390   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3997    2.4642   -1.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5269    2.6205    0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6102    0.1340   -1.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 13 14  1  0
 13 15  1  0
 10 16  2  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 12 24  1  0
 14 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dicarzol	ChEBI
N'-(m-hydroxyphenyl)-N,N-dimethylformamidine methylcarbamate ester	ChEBI
N'-(m-hydroxyphenyl)-N,N-dimethylformamidine methylcarbamic acid ester	Generator
Formetanic acid	Generator
Formetanate monohydrochloride	MeSH

Chemical Formula

C₁₁H₁₅N₃O₂

Average Molecular Weight

221.2557

Monoisotopic Molecular Weight

221.116426739

IUPAC Name

3-{[(dimethylamino)methylidene]amino}phenyl N-methylcarbamate

Traditional Name

formetanate

CAS Registry Number

Not Available

SMILES

CNC(=O)OC1=CC=CC(=C1)N=CN(C)C

InChI Identifier

InChI=1S/C11H15N3O2/c1-12-11(15)16-10-6-4-5-9(7-10)13-8-14(2)3/h4-8H,1-3H3,(H,12,15)

InChI Key

RMFNNCGOSPBBAD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenyl methylcarbamates

Direct Parent

Phenyl methylcarbamates

Alternative Parents

Substituents

Phenyl methylcarbamate
Phenoxy compound
Carbamic acid ester
Carbonic acid derivative
Amidine
Carboxylic acid amidine
Formamidine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carbamate ester (CHEBI:38491 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Cytoplasm (HMDB: HMDB0252444)
Extracellular (HMDB: HMDB0252444)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Industrial application

Agrochemical (HMDB: HMDB0252444)

Agriculture

Pesticide

Acaricide (HMDB: HMDB0252444)
Carbamate insecticide (HMDB: HMDB0252444)

Biological role

Modulator

Inhibitor

EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0252444)

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	0.91	ALOGPS
logP	1.08	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	14.77	ChemAxon
pKa (Strongest Basic)	8.89	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	53.93 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.62 m³·mol⁻¹	ChemAxon
Polarizability	24 Å³	ChemAxon
Number of Rings	1	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]+	149.88	30932474
DeepCCS	[M-H]-	147.485	30932474
DeepCCS	[M-2H]-	180.712	30932474
DeepCCS	[M+Na]+	155.793	30932474
AllCCS	[M+H]+	151.4	32859911
AllCCS	[M+H-H2O]+	147.6	32859911
AllCCS	[M+NH4]+	154.9	32859911
AllCCS	[M+Na]+	155.9	32859911
AllCCS	[M-H]-	153.3	32859911
AllCCS	[M+Na-2H]-	153.9	32859911
AllCCS	[M+HCOO]-	154.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.5518 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.44 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1068.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	244.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	116.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	58.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	256.7 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	322.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	659.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	813.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	166.5 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	983.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	223.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	569.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	393.1 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	78.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Formetanate	CNC(=O)OC1=CC=CC(=C1)N=CN(C)C	2662.9	Standard polar	33892256
Formetanate	CNC(=O)OC1=CC=CC(=C1)N=CN(C)C	2053.0	Standard non polar	33892256
Formetanate	CNC(=O)OC1=CC=CC(=C1)N=CN(C)C	2086.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Formetanate,1TMS,isomer #1	CN(C)C=NC1=CC=CC(OC(=O)N(C)[Si](C)(C)C)=C1	2028.0	Semi standard non polar	33892256
Formetanate,1TMS,isomer #1	CN(C)C=NC1=CC=CC(OC(=O)N(C)[Si](C)(C)C)=C1	2182.4	Standard non polar	33892256
Formetanate,1TMS,isomer #1	CN(C)C=NC1=CC=CC(OC(=O)N(C)[Si](C)(C)C)=C1	2855.8	Standard polar	33892256
Formetanate,1TBDMS,isomer #1	CN(C)C=NC1=CC=CC(OC(=O)N(C)[Si](C)(C)C(C)(C)C)=C1	2274.4	Semi standard non polar	33892256
Formetanate,1TBDMS,isomer #1	CN(C)C=NC1=CC=CC(OC(=O)N(C)[Si](C)(C)C(C)(C)C)=C1	2399.4	Standard non polar	33892256
Formetanate,1TBDMS,isomer #1	CN(C)C=NC1=CC=CC(OC(=O)N(C)[Si](C)(C)C(C)(C)C)=C1	2954.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Formetanate GC-MS (Non-derivatized) - 70eV, Positive	splash10-06r2-9700000000-bb1a094afe851a143774	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formetanate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formetanate 10V, Positive-QTOF	splash10-01b9-3960000000-4b56301bcfa3ad90fbc8	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formetanate 20V, Positive-QTOF	splash10-00kb-2900000000-93645d39167251da4bcd	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formetanate 40V, Positive-QTOF	splash10-05mk-9500000000-8e33d7bda7824fc19d7c	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formetanate 10V, Negative-QTOF	splash10-0ab9-9240000000-45d4f32945310c600d7b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formetanate 20V, Negative-QTOF	splash10-0bt9-9720000000-aa90716d48b31193075b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formetanate 40V, Negative-QTOF	splash10-0aba-9600000000-b6cdcd8af1046026fbc7	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formetanate 10V, Positive-QTOF	splash10-00di-0190000000-adf181d63f10bdc7c45f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formetanate 20V, Positive-QTOF	splash10-01b9-0930000000-f4500af1e57b60fc4c03	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formetanate 40V, Positive-QTOF	splash10-002b-9500000000-2864ffe5c44ca27967b2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formetanate 10V, Negative-QTOF	splash10-03k9-0950000000-bde16a20206217c68397	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formetanate 20V, Negative-QTOF	splash10-03di-0900000000-491b53579de51d479210	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formetanate 40V, Negative-QTOF	splash10-006y-8900000000-6d476454cf2bb93c615b	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Formetanate

METLIN ID

Not Available

PubChem Compound

31099

PDB ID

Not Available

ChEBI ID

38491

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 Formetanate (HMDB0252444)

MOL for HMDB0252444 (Formetanate)

3D MOL for HMDB0252444 (Formetanate)

3D SDF for HMDB0252444 (Formetanate)

3D-SDF for HMDB0252444 (Formetanate)

PDB for HMDB0252444 (Formetanate)

3D PDB for HMDB0252444 (Formetanate)

SMILES for HMDB0252444 (Formetanate)

INCHI for HMDB0252444 (Formetanate)

Structure for HMDB0252444 (Formetanate)

3D Structure for HMDB0252444 (Formetanate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra