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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:50:19 UTC

Update Date

2021-09-26 23:12:02 UTC

HMDB ID

HMDB0256405

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Phenmedipham

Description

Phenmedipham belongs to the class of organic compounds known as phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids. Based on a literature review a small amount of articles have been published on Phenmedipham. This compound has been identified in human blood as reported by (PMID: 31557052 ). Phenmedipham is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Phenmedipham 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

HMDB0256405
     RDKit          3D
Phenmedipham
 38 39  0  0  0  0  0  0  0  0999 V2000
   -7.3620   -0.7795    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8062    0.4662    0.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4464    0.7031    0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9277    1.8982    0.8986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7098   -0.1976   -0.1218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986    0.0662   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8360    0.9117   -1.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    1.1741   -1.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298    0.5789   -0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0151   -0.2613    0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2650   -0.8988    1.4906 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1015   -0.7510    1.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8516   -0.3801    2.6400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6461   -0.9963    0.3861 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0605   -0.8718    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8670   -1.7310    1.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2363   -1.6219    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8353   -0.6770    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    0.1853   -0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7165    1.2227   -1.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7007    0.0542   -0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3971   -0.5079    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9030   -1.5867    0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4471   -0.7759    0.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2027   -0.9592   -0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5349    2.6645    1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5794    1.3387   -1.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1736    1.8384   -2.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4147    0.7894   -0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3288    0.5181    2.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3975   -2.4753    1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8279   -2.2985    1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9186   -0.6081    0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2832    1.2602   -2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7969    0.9435   -1.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7095    2.2127   -0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0760    0.7222   -1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8059   -1.1705    1.4165 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
  3  5  2  3
  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  1  0
 12 13  1  0
 12 14  2  3
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 10 22  2  0
 22  6  1  0
 21 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 13 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
M  END


  Mrv0541 10151420142D          

 22 23  0  0  0  0            999 V2000
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    0.0000    0.0000 C   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
   -5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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
   -6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    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
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    1.2375    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
   -7.1447    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    0.8250    0.0000 O   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
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
 11  1  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  2  0  0  0  0
 12  6  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  2  0  0  0  0
 14  8  2  0  0  0  0
 14 10  1  0  0  0  0
 17 13  1  4  0  0  0
 17 15  2  0  0  0  0
 18 12  1  4  0  0  0
 18 16  2  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21  2  1  0  0  0  0
 21 15  1  0  0  0  0
 22 14  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256405

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(O)=NC1=CC(OC(O)=NC2=CC=CC(C)=C2)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16N2O4/c1-11-5-3-6-12(9-11)18-16(20)22-14-8-4-7-13(10-14)17-15(19)21-2/h3-10H,1-2H3,(H,17,19)(H,18,20)

> <INCHI_KEY>
IDOWTHOLJBTAFI-UHFFFAOYSA-N

> <FORMULA>
C16H16N2O4

> <MOLECULAR_WEIGHT>
300.3092

> <EXACT_MASS>
300.11100701

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.767763266889837

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-3-{[hydroxy(methoxy)methylidene]amino}phenoxy-N-(3-methylphenyl)methanimidic acid

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
5.280475334666667

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.701149542398374

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.907709565422298

> <JCHEM_PKA_STRONGEST_BASIC>
-2.710527573864756

> <JCHEM_POLAR_SURFACE_AREA>
83.64000000000001

> <JCHEM_REFRACTIVITY>
85.62910000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-3-{[hydroxy(methoxy)methylidene]amino}phenoxy-N-(3-methylphenyl)methanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256405
     RDKit          3D
Phenmedipham
 38 39  0  0  0  0  0  0  0  0999 V2000
   -7.3620   -0.7795    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8062    0.4662    0.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4464    0.7031    0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9277    1.8982    0.8986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7098   -0.1976   -0.1218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986    0.0662   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8360    0.9117   -1.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    1.1741   -1.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298    0.5789   -0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0151   -0.2613    0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2650   -0.8988    1.4906 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1015   -0.7510    1.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8516   -0.3801    2.6400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6461   -0.9963    0.3861 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0605   -0.8718    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8670   -1.7310    1.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2363   -1.6219    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8353   -0.6770    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    0.1853   -0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7165    1.2227   -1.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7007    0.0542   -0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3971   -0.5079    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9030   -1.5867    0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4471   -0.7759    0.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2027   -0.9592   -0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5349    2.6645    1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5794    1.3387   -1.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1736    1.8384   -2.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4147    0.7894   -0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3288    0.5181    2.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3975   -2.4753    1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8279   -2.2985    1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9186   -0.6081    0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2832    1.2602   -2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7969    0.9435   -1.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7095    2.2127   -0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0760    0.7222   -1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8059   -1.1705    1.4165 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
  3  5  2  3
  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  1  0
 12 13  1  0
 12 14  2  3
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 10 22  2  0
 22  6  1  0
 21 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 13 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
M  END

HEADER    PROTEIN                                 15-OCT-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-OCT-14         0                                  
HETATM    1  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -16.004   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -12.003   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -14.670   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0     -13.337   1.540   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -6.668   3.850   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0     -14.670   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0     -16.004   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   21                                                            
CONECT    3    5    6                                                       
CONECT    4    7    8                                                       
CONECT    5    3   11                                                       
CONECT    6    3   12                                                       
CONECT    7    4   13                                                       
CONECT    8    4   14                                                       
CONECT    9   11   12                                                       
CONECT   10   13   14                                                       
CONECT   11    1    5    9                                                  
CONECT   12    6    9   18                                                  
CONECT   13    7   10   17                                                  
CONECT   14    8   10   22                                                  
CONECT   15   17   19   21                                                  
CONECT   16   18   20   22                                                  
CONECT   17   13   15                                                       
CONECT   18   12   16                                                       
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21    2   15                                                       
CONECT   22   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0256405
HETATM    1  C1  UNL     1      -7.362  -0.780   0.125  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.806   0.466   0.524  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.446   0.703   0.419  1.00  0.00           C  
HETATM    4  O2  UNL     1      -4.928   1.898   0.899  1.00  0.00           O  
HETATM    5  N1  UNL     1      -4.710  -0.198  -0.122  1.00  0.00           N  
HETATM    6  C3  UNL     1      -3.299   0.066  -0.222  1.00  0.00           C  
HETATM    7  C4  UNL     1      -2.836   0.912  -1.212  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.500   1.174  -1.323  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.630   0.579  -0.430  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.015  -0.261   0.565  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.265  -0.899   1.491  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.102  -0.751   1.523  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.852  -0.380   2.640  1.00  0.00           O  
HETATM   14  N2  UNL     1       1.646  -0.996   0.386  1.00  0.00           N  
HETATM   15  C9  UNL     1       3.061  -0.872   0.312  1.00  0.00           C  
HETATM   16  C10 UNL     1       3.867  -1.731   1.068  1.00  0.00           C  
HETATM   17  C11 UNL     1       5.236  -1.622   1.006  1.00  0.00           C  
HETATM   18  C12 UNL     1       5.835  -0.677   0.210  1.00  0.00           C  
HETATM   19  C13 UNL     1       5.071   0.185  -0.548  1.00  0.00           C  
HETATM   20  C14 UNL     1       5.717   1.223  -1.423  1.00  0.00           C  
HETATM   21  C15 UNL     1       3.701   0.054  -0.467  1.00  0.00           C  
HETATM   22  C16 UNL     1      -2.397  -0.508   0.649  1.00  0.00           C  
HETATM   23  H1  UNL     1      -6.903  -1.587   0.731  1.00  0.00           H  
HETATM   24  H2  UNL     1      -8.447  -0.776   0.367  1.00  0.00           H  
HETATM   25  H3  UNL     1      -7.203  -0.959  -0.937  1.00  0.00           H  
HETATM   26  H4  UNL     1      -5.535   2.664   1.122  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.579   1.339  -1.872  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.174   1.838  -2.106  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.415   0.789  -0.520  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.329   0.518   2.566  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.397  -2.475   1.695  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.828  -2.298   1.600  1.00  0.00           H  
HETATM   33  H11 UNL     1       6.919  -0.608   0.176  1.00  0.00           H  
HETATM   34  H12 UNL     1       5.283   1.260  -2.422  1.00  0.00           H  
HETATM   35  H13 UNL     1       6.797   0.943  -1.509  1.00  0.00           H  
HETATM   36  H14 UNL     1       5.710   2.213  -0.898  1.00  0.00           H  
HETATM   37  H15 UNL     1       3.076   0.722  -1.055  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.806  -1.171   1.416  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    5    5
CONECT    4   26
CONECT    5    6
CONECT    6    7    7   22
CONECT    7    8   27
CONECT    8    9    9   28
CONECT    9   10   29
CONECT   10   11   22   22
CONECT   11   12
CONECT   12   13   14   14
CONECT   13   30
CONECT   14   15
CONECT   15   16   16   21
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   19   33
CONECT   19   20   21   21
CONECT   20   34   35   36
CONECT   21   37
CONECT   22   38
END

HMDB0256405
     RDKit          3D
Phenmedipham
 38 39  0  0  0  0  0  0  0  0999 V2000
   -7.3620   -0.7795    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8062    0.4662    0.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4464    0.7031    0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9277    1.8982    0.8986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7098   -0.1976   -0.1218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986    0.0662   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8360    0.9117   -1.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    1.1741   -1.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298    0.5789   -0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0151   -0.2613    0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2650   -0.8988    1.4906 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1015   -0.7510    1.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8516   -0.3801    2.6400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6461   -0.9963    0.3861 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0605   -0.8718    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8670   -1.7310    1.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2363   -1.6219    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8353   -0.6770    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    0.1853   -0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7165    1.2227   -1.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7007    0.0542   -0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3971   -0.5079    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9030   -1.5867    0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4471   -0.7759    0.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2027   -0.9592   -0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5349    2.6645    1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5794    1.3387   -1.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1736    1.8384   -2.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4147    0.7894   -0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3288    0.5181    2.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3975   -2.4753    1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8279   -2.2985    1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9186   -0.6081    0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2832    1.2602   -2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7969    0.9435   -1.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7095    2.2127   -0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0760    0.7222   -1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8059   -1.1705    1.4165 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
  3  5  2  3
  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  1  0
 12 13  1  0
 12 14  2  3
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 10 22  2  0
 22  6  1  0
 21 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 13 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(Methoxyformamido)phenyl (3-methylphenyl)carbamate	ChEBI
3-[(Methoxycarbonyl)amino]phenyl (3-methylphenyl)carbamate	ChEBI
3-Methoxycarbonyl-N-(3'-methylphenyl)-carbamate	ChEBI
Methyl 3-(3-methylcarbaniloyloxy)carbanilate	ChEBI
3-(Methoxyformamido)phenyl (3-methylphenyl)carbamic acid	Generator
3-[(Methoxycarbonyl)amino]phenyl (3-methylphenyl)carbamic acid	Generator
3-Methoxycarbonyl-N-(3'-methylphenyl)-carbamic acid	Generator
Methyl 3-(3-methylcarbaniloyloxy)carbanilic acid	Generator
Betanal	MeSH
Fenmedifam	MeSH

Chemical Formula

C₁₆H₁₆N₂O₄

Average Molecular Weight

300.3092

Monoisotopic Molecular Weight

300.11100701

IUPAC Name

1-3-{[hydroxy(methoxy)methylidene]amino}phenoxy-N-(3-methylphenyl)methanimidic acid

Traditional Name

1-3-{[hydroxy(methoxy)methylidene]amino}phenoxy-N-(3-methylphenyl)methanimidic acid

CAS Registry Number

Not Available

SMILES

COC(O)=NC1=CC(OC(O)=NC2=CC=CC(C)=C2)=CC=C1

InChI Identifier

InChI=1S/C16H16N2O4/c1-11-5-3-6-12(9-11)18-16(20)22-14-8-4-7-13(10-14)17-15(19)21-2/h3-10H,1-2H3,(H,17,19)(H,18,20)

InChI Key

IDOWTHOLJBTAFI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylcarbamic acid esters

Direct Parent

Phenylcarbamic acid esters

Alternative Parents

Substituents

Phenylcarbamic acid ester
Phenoxy compound
Toluene
Carbamic acid ester
Carbonic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carbamate ester (CHEBI:81734 )
Carbanilate herbicides (C18420 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0256405)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Metabolic Pathways (HMDB: HMDB0256405)

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	2.5	ALOGPS
logP	5.28	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	2.91	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.64 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.63 m³·mol⁻¹	ChemAxon
Polarizability	30.77 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	171.793	30932474
DeepCCS	[M-H]-	169.435	30932474
DeepCCS	[M-2H]-	203.013	30932474
DeepCCS	[M+Na]+	178.24	30932474
AllCCS	[M+H]+	170.0	32859911
AllCCS	[M+H-H2O]+	166.5	32859911
AllCCS	[M+NH4]+	173.1	32859911
AllCCS	[M+Na]+	174.1	32859911
AllCCS	[M-H]-	173.2	32859911
AllCCS	[M+Na-2H]-	172.7	32859911
AllCCS	[M+HCOO]-	172.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.54 minutes	32390414
Predicted by Siyang on May 30, 2022	14.3842 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.9 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2202.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	345.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	71.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	614.5 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	693.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	120.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1122.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	462.9 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	1507.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	283.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	395.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	404.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	233.6 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	114.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenmedipham	COC(O)=NC1=CC(OC(O)=NC2=CC=CC(C)=C2)=CC=C1	3516.1	Standard polar	33892256
Phenmedipham	COC(O)=NC1=CC(OC(O)=NC2=CC=CC(C)=C2)=CC=C1	2630.2	Standard non polar	33892256
Phenmedipham	COC(O)=NC1=CC(OC(O)=NC2=CC=CC(C)=C2)=CC=C1	2629.8	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 - Phenmedipham GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0910000000-f30d7fef5d59b6c5ce93	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenmedipham GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenmedipham GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenmedipham GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenmedipham GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenmedipham GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenmedipham GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenmedipham GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00lr-5900000000-18214c4b9332b3821a3e	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 - Phenmedipham 30V, Positive-QTOF	splash10-000i-0900000000-00031c14ca44e9139da9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 15V, Positive-QTOF	splash10-014r-0900000000-58c2bf322552cc023a2c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 30V, Positive-QTOF	splash10-000i-0900000000-48fd93926a23be06e22f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 40V, Positive-QTOF	splash10-000i-0900000000-e0ddaebfe93fd113eec8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 20V, Positive-QTOF	splash10-000i-0900000000-ec1e788887825ffd4f0c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 10V, Positive-QTOF	splash10-014i-0900000000-f503ecc696af8c003a6e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 50V, Positive-QTOF	splash10-000i-0900000000-73e4c8828d11574f5451	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 35V, Positive-QTOF	splash10-014i-0900000000-285f09d3c2697ef6975a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 75V, Positive-QTOF	splash10-052r-3900000000-1c4f4f8b000368ac97de	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 90V, Positive-QTOF	splash10-06el-8900000000-89453a33a33ec2ad9279	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 60V, Positive-QTOF	splash10-000i-1900000000-6a34a96bdb4b2086cd06	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 45V, Positive-QTOF	splash10-000i-0900000000-0fbfef39b582949ab789	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 35V, Positive-QTOF	splash10-014i-0900000000-aba50b6e242108613201	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 45V, Positive-QTOF	splash10-000i-0900000000-6c56388e0bc4b72f9781	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 30V, Positive-QTOF	splash10-000i-0900000000-9f94251a5005a58d3751	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 60V, Positive-QTOF	splash10-000i-1900000000-308e1ba29a7937090320	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 15V, Positive-QTOF	splash10-014r-0900000000-1a043edb4709fa7aad1d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 75V, Positive-QTOF	splash10-052r-3900000000-dcc4c2258728e16c13a9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenmedipham 90V, Positive-QTOF	splash10-06el-8900000000-1ec41aa995a5fb8c1e67	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenmedipham 10V, Positive-QTOF	splash10-0gb9-0915000000-63d6e03ed88c54642817	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenmedipham 20V, Positive-QTOF	splash10-014i-0910000000-29a9b44697d8a365aa4a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenmedipham 40V, Positive-QTOF	splash10-00m0-2900000000-9af527c638cac566c742	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenmedipham 10V, Negative-QTOF	splash10-00lr-0960000000-7f9c2c8524e4108413e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenmedipham 20V, Negative-QTOF	splash10-00lr-0930000000-35b7fc9406bb7cece661	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenmedipham 40V, Negative-QTOF	splash10-001i-0900000000-b8bb1126db209fc546e1	2016-08-03	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

23134

KEGG Compound ID

C18420

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

81734

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1312321

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 Phenmedipham (HMDB0256405)

MOL for HMDB0256405 (Phenmedipham)

3D MOL for HMDB0256405 (Phenmedipham)

3D SDF for HMDB0256405 (Phenmedipham)

3D-SDF for HMDB0256405 (Phenmedipham)

PDB for HMDB0256405 (Phenmedipham)

3D PDB for HMDB0256405 (Phenmedipham)

SMILES for HMDB0256405 (Phenmedipham)

INCHI for HMDB0256405 (Phenmedipham)

Structure for HMDB0256405 (Phenmedipham)

3D Structure for HMDB0256405 (Phenmedipham)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra