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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:27 UTC

Update Date

2022-03-07 02:53:07 UTC

HMDB ID

HMDB0031787

Secondary Accession Numbers

HMDB31787

Metabolite Identification

Common Name

Fenamiphos

Description

Fenamiphos, also known as nemacur or bay sra 3886, belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group. Based on a literature review very few articles have been published on Fenamiphos.

Structure

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

HMDB0031787
     RDKit          3D
Fenamiphos
 41 41  0  0  0  0  0  0  0  0999 V2000
   -3.0280    3.6374    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8268    2.7118    0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5520    2.1203    1.3155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6401    0.4261    1.1312 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.6227    0.0809    2.3205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5161    0.1945   -0.3689 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3229   -0.9639   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1918   -1.2037    0.7647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988   -2.2344   -0.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049   -0.4427    1.3543 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9087   -0.4240    0.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507    0.4630   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276    0.4620   -0.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3683   -0.4363   -0.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9948   -0.4117   -1.3750 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8335    1.0367   -0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0650   -1.3598    0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9922   -2.5189    0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8511   -1.3166    1.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9249    2.8883    0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2500    4.1185   -0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9055    4.2059    1.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9815    3.4233   -0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432    2.0311   -0.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7612    0.0685   -1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0594   -0.7856   -1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6208   -0.3175    1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0308   -1.8564    0.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5617   -1.8057    1.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1126   -3.1343   -0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5770   -2.3433   -1.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5544   -2.1094   -0.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4555    1.1827   -0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6882    1.1573   -1.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4488    1.1831    0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8874    0.9588   -0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4611    1.9282   -1.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1611   -3.0823   -0.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4726   -3.2839    1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9380   -2.2129    1.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6825   -2.0350    1.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  2  0
 19 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
M  END


  Mrv0541 05061306082D          

 19 19  0  0  0  0            999 V2000
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -0.2211    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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
   -1.2375   -0.9355    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   -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
   -0.4125   -0.9355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11  9  2  0  0  0  0
 12  7  2  0  0  0  0
 12  9  1  0  0  0  0
 13  8  2  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 16  6  1  0  0  0  0
 17 12  1  0  0  0  0
 18 14  1  0  0  0  0
 18 15  2  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19  5  1  0  0  0  0
 19 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031787

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H22NO3PS/c1-6-16-18(15,14-10(2)3)17-12-7-8-13(19-5)11(4)9-12/h7-10H,6H2,1-5H3,(H,14,15)

> <INCHI_KEY>
ZCJPOPBZHLUFHF-UHFFFAOYSA-N

> <FORMULA>
C13H22NO3PS

> <MOLECULAR_WEIGHT>
303.357

> <EXACT_MASS>
303.105800777

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
31.968802357434868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{ethoxy[3-methyl-4-(methylsulfanyl)phenoxy]phosphoryl}(propan-2-yl)amine

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
3.314405651666667

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.538661240658698

> <JCHEM_POLAR_SURFACE_AREA>
47.56

> <JCHEM_REFRACTIVITY>
81.54230000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fenamiphos

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031787
     RDKit          3D
Fenamiphos
 41 41  0  0  0  0  0  0  0  0999 V2000
   -3.0280    3.6374    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8268    2.7118    0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5520    2.1203    1.3155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6401    0.4261    1.1312 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.6227    0.0809    2.3205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5161    0.1945   -0.3689 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3229   -0.9639   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1918   -1.2037    0.7647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988   -2.2344   -0.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049   -0.4427    1.3543 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9087   -0.4240    0.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507    0.4630   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276    0.4620   -0.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3683   -0.4363   -0.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9948   -0.4117   -1.3750 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8335    1.0367   -0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0650   -1.3598    0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9922   -2.5189    0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8511   -1.3166    1.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9249    2.8883    0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2500    4.1185   -0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9055    4.2059    1.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9815    3.4233   -0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432    2.0311   -0.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7612    0.0685   -1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0594   -0.7856   -1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6208   -0.3175    1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0308   -1.8564    0.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5617   -1.8057    1.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1126   -3.1343   -0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5770   -2.3433   -1.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5544   -2.1094   -0.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4555    1.1827   -0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6882    1.1573   -1.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4488    1.1831    0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8874    0.9588   -0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4611    1.9282   -1.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1611   -3.0823   -0.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4726   -3.2839    1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9380   -2.2129    1.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6825   -2.0350    1.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  2  0
 19 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.080  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.080  -0.413   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.310  -1.746   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -0.770  -1.746   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       0.770  -4.414   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  P   UNK     0       0.000  -3.080   0.000  0.00  0.00           P+0
HETATM   19  S   UNK     0       1.334   3.850   0.000  0.00  0.00           S+0
CONECT    1    6                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5   19                                                            
CONECT    6    1   16                                                       
CONECT    7    8   12                                                       
CONECT    8    7   13                                                       
CONECT    9   11   12                                                       
CONECT   10    2    3   14                                                  
CONECT   11    4    9   13                                                  
CONECT   12    7    9   17                                                  
CONECT   13    8   11   19                                                  
CONECT   14   10   18                                                       
CONECT   15   18                                                            
CONECT   16    6   18                                                       
CONECT   17   12   18                                                       
CONECT   18   14   15   16   17                                             
CONECT   19    5   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0031787
HETATM    1  C1  UNL     1      -3.028   3.637   0.284  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.827   2.712   0.073  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.552   2.120   1.315  1.00  0.00           O  
HETATM    4  P1  UNL     1      -1.640   0.426   1.131  1.00  0.00           P  
HETATM    5  O2  UNL     1      -2.623   0.081   2.321  1.00  0.00           O  
HETATM    6  N1  UNL     1      -2.516   0.194  -0.369  1.00  0.00           N  
HETATM    7  C3  UNL     1      -3.323  -0.964  -0.438  1.00  0.00           C  
HETATM    8  C4  UNL     1      -4.192  -1.204   0.765  1.00  0.00           C  
HETATM    9  C5  UNL     1      -2.599  -2.234  -0.798  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.305  -0.443   1.354  1.00  0.00           O  
HETATM   11  C6  UNL     1       0.909  -0.424   0.704  1.00  0.00           C  
HETATM   12  C7  UNL     1       1.251   0.463  -0.322  1.00  0.00           C  
HETATM   13  C8  UNL     1       2.428   0.462  -0.945  1.00  0.00           C  
HETATM   14  C9  UNL     1       3.368  -0.436  -0.607  1.00  0.00           C  
HETATM   15  S1  UNL     1       4.995  -0.412  -1.375  1.00  0.00           S  
HETATM   16  C10 UNL     1       5.834   1.037  -0.573  1.00  0.00           C  
HETATM   17  C11 UNL     1       3.065  -1.360   0.400  1.00  0.00           C  
HETATM   18  C12 UNL     1       3.992  -2.519   0.674  1.00  0.00           C  
HETATM   19  C13 UNL     1       1.851  -1.317   1.016  1.00  0.00           C  
HETATM   20  H1  UNL     1      -3.925   2.888   0.406  1.00  0.00           H  
HETATM   21  H2  UNL     1      -3.250   4.118  -0.635  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.906   4.206   1.174  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.982   3.423  -0.189  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.943   2.031  -0.704  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.761   0.069  -1.108  1.00  0.00           H  
HETATM   26  H7  UNL     1      -4.059  -0.786  -1.282  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.621  -0.317   1.223  1.00  0.00           H  
HETATM   28  H9  UNL     1      -5.031  -1.856   0.445  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.562  -1.806   1.488  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.113  -3.134  -0.393  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.577  -2.343  -1.912  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.554  -2.109  -0.433  1.00  0.00           H  
HETATM   33  H14 UNL     1       0.456   1.183  -0.646  1.00  0.00           H  
HETATM   34  H15 UNL     1       2.688   1.157  -1.722  1.00  0.00           H  
HETATM   35  H16 UNL     1       5.449   1.183   0.443  1.00  0.00           H  
HETATM   36  H17 UNL     1       6.887   0.959  -0.650  1.00  0.00           H  
HETATM   37  H18 UNL     1       5.461   1.928  -1.166  1.00  0.00           H  
HETATM   38  H19 UNL     1       4.161  -3.082  -0.291  1.00  0.00           H  
HETATM   39  H20 UNL     1       3.473  -3.284   1.317  1.00  0.00           H  
HETATM   40  H21 UNL     1       4.938  -2.213   1.079  1.00  0.00           H  
HETATM   41  H22 UNL     1       1.682  -2.035   1.874  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4
CONECT    4    5    5    6   10
CONECT    6    7   25
CONECT    7    8    9   26
CONECT    8   27   28   29
CONECT    9   30   31   32
CONECT   10   11
CONECT   11   12   12   19
CONECT   12   13   33
CONECT   13   14   14   34
CONECT   14   15   17
CONECT   15   16
CONECT   16   35   36   37
CONECT   17   18   19   19
CONECT   18   38   39   40
CONECT   19   41
END

HMDB0031787
     RDKit          3D
Fenamiphos
 41 41  0  0  0  0  0  0  0  0999 V2000
   -3.0280    3.6374    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8268    2.7118    0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5520    2.1203    1.3155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6401    0.4261    1.1312 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.6227    0.0809    2.3205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5161    0.1945   -0.3689 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3229   -0.9639   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1918   -1.2037    0.7647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988   -2.2344   -0.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049   -0.4427    1.3543 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9087   -0.4240    0.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507    0.4630   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276    0.4620   -0.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3683   -0.4363   -0.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9948   -0.4117   -1.3750 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8335    1.0367   -0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0650   -1.3598    0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9922   -2.5189    0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8511   -1.3166    1.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9249    2.8883    0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2500    4.1185   -0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9055    4.2059    1.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9815    3.4233   -0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432    2.0311   -0.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7612    0.0685   -1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0594   -0.7856   -1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6208   -0.3175    1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0308   -1.8564    0.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5617   -1.8057    1.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1126   -3.1343   -0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5770   -2.3433   -1.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5544   -2.1094   -0.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4555    1.1827   -0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6882    1.1573   -1.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4488    1.1831    0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8874    0.9588   -0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4611    1.9282   -1.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1611   -3.0823   -0.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4726   -3.2839    1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9380   -2.2129    1.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6825   -2.0350    1.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  2  0
 19 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ethyl 3-methyl-4-(methylsulfanyl)phenyl (1-methylethyl)amidophosphate	ChEBI
Ethyl 3-methyl-4-(methylthio)phenyl isopropylphosphoramidate	ChEBI
Ethyl 4-(methylthio)-m-tolyl isopropylphosphoramidate	ChEBI
Isopropylamino-O-ethyl-(4-methylmercapto-3-methylphenyl)phosphate	ChEBI
Methaphenamiphos	ChEBI
Nemacur	ChEBI
Phenamiphos	ChEBI
Ethyl 3-methyl-4-(methylsulfanyl)phenyl (1-methylethyl)amidophosphoric acid	Generator
Ethyl 3-methyl-4-(methylsulphanyl)phenyl (1-methylethyl)amidophosphate	Generator
Ethyl 3-methyl-4-(methylsulphanyl)phenyl (1-methylethyl)amidophosphoric acid	Generator
Ethyl 3-methyl-4-(methylthio)phenyl isopropylphosphoramidic acid	Generator
Ethyl 4-(methylthio)-m-tolyl isopropylphosphoramidic acid	Generator
Isopropylamino-O-ethyl-(4-methylmercapto-3-methylphenyl)phosphoric acid	Generator
BAY sra 3886	HMDB
Ethyl 3-methyl-4-(methylthio)phenyl 1-methylethylphosphoramidate, 9ci	HMDB
Ethyl 3-methyl-4-(methylthio)phenyl isopropylamidophosphate	HMDB
Ethyl 4-(methylthio)m-tolyl isopropylphosphoroamidate	HMDB
Ethyl 4-methylthio-m-tolyl isopropylphosphoramidate, 8ci	HMDB
Ethyl-4-(methylthio)-m-tolyl isopropylphosphoramidate	HMDB
m-Cresol, 4-(methylthio)-, ethyl isopropylphosphoramidate	HMDB
Nemacur p	HMDB
Phenamifos sulfoxide	HMDB

Chemical Formula

C₁₃H₂₂NO₃PS

Average Molecular Weight

303.357

Monoisotopic Molecular Weight

303.105800777

IUPAC Name

{ethoxy[3-methyl-4-(methylsulfanyl)phenoxy]phosphoryl}(propan-2-yl)amine

Traditional Name

fenamiphos

CAS Registry Number

22224-92-6

SMILES

CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1

InChI Identifier

InChI=1S/C13H22NO3PS/c1-6-16-18(15,14-10(2)3)17-12-7-8-13(19-5)11(4)9-12/h7-10H,6H2,1-5H3,(H,14,15)

InChI Key

ZCJPOPBZHLUFHF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxy compounds

Direct Parent

Phenoxy compounds

Alternative Parents

Substituents

Phenoxy compound
Aryl thioether
Thiophenol ether
Phosphoric diester monoamide
Toluene
Alkylarylthioether
Organic phosphoric acid derivative
Phosphoric acid ester
Organic phosphoric acid amide
Sulfenyl compound
Thioether
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organic oxide
Organonitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phosphoramidate ester (CHEBI:38680 )
organophosphate insecticide (CHEBI:38680 )
organophosphate nematicide (CHEBI:38680 )
Phosphoramido insecticides (C18659 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Vascular disorder

Hypertension (HMDB: HMDB0031787)
Hypotension (HMDB: HMDB0031787)

Blood and lymphatic system disorder

Hypoglycemia (HMDB: HMDB0031787)

Observation

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Mood disorder

Major depressive disorder (HMDB: HMDB0031787)

Neurotic, stress-related, or somatoform disorder

Anxiety (HMDB: HMDB0031787)

Coma (HMDB: HMDB0031787)

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031787)
Cell membrane (HMDB: HMDB0031787)

Source

Endogenous

Endogenous (HMDB: HMDB0031787)

Exogenous

Food

Food (HMDB: HMDB0031787)

Synthetic

Synthetic (HMDB: HMDB0031787)

Exogenous (HMDB: HMDB0031787)

Process

Not Available

Role

Environmental role

Air pollutant (HMDB: HMDB0031787)

Industrial application

Agrochemical (HMDB: HMDB0031787)

Agriculture

Pesticide

Acaricide (HMDB: HMDB0031787)
Acaricide (HMDB: HMDB0031787)

Biological role

Modulator

Inhibitor

EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0031787)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	49 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.33 mg/mL at 20 °C	Not Available
LogP	3.23	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	3.05	ALOGPS
logP	3.31	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	10.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.56 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	81.54 m³·mol⁻¹	ChemAxon
Polarizability	31.97 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
DarkChem	[M+H]+	171.751	31661259
DarkChem	[M-H]-	168.601	31661259
DeepCCS	[M+H]+	171.678	30932474
DeepCCS	[M-H]-	169.32	30932474
DeepCCS	[M-2H]-	202.207	30932474
DeepCCS	[M+Na]+	177.772	30932474
AllCCS	[M+H]+	170.3	32859911
AllCCS	[M+H-H2O]+	167.2	32859911
AllCCS	[M+NH4]+	173.1	32859911
AllCCS	[M+Na]+	174.0	32859911
AllCCS	[M-H]-	169.6	32859911
AllCCS	[M+Na-2H]-	170.2	32859911
AllCCS	[M+HCOO]-	171.0	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.	7.56 minutes	32390414
Predicted by Siyang on May 30, 2022	16.9198 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.71 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2364.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	514.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	263.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	155.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	737.7 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	810.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1461.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	549.7 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	1572.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	457.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	414.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	328.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	341.3 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	9.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fenamiphos	CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1	2954.1	Standard polar	33892256
Fenamiphos	CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1	2135.1	Standard non polar	33892256
Fenamiphos	CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1	2127.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fenamiphos,1TMS,isomer #1	CCOP(=O)(OC1=CC=C(SC)C(C)=C1)N(C(C)C)[Si](C)(C)C	2236.5	Semi standard non polar	33892256
Fenamiphos,1TMS,isomer #1	CCOP(=O)(OC1=CC=C(SC)C(C)=C1)N(C(C)C)[Si](C)(C)C	2277.1	Standard non polar	33892256
Fenamiphos,1TBDMS,isomer #1	CCOP(=O)(OC1=CC=C(SC)C(C)=C1)N(C(C)C)[Si](C)(C)C(C)(C)C	2490.3	Semi standard non polar	33892256
Fenamiphos,1TBDMS,isomer #1	CCOP(=O)(OC1=CC=C(SC)C(C)=C1)N(C(C)C)[Si](C)(C)C(C)(C)C	2481.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fenamiphos GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w99-3890000000-69a80218e9aa4efa6a6e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fenamiphos GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-8953000000-a605d591b58cd6b9edb9	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 - Fenamiphos 60V, Positive-QTOF	splash10-0uxr-0390000000-27a48287856f24d6700c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenamiphos 75V, Positive-QTOF	splash10-0udi-2690000000-b722d2a9468435e12094	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenamiphos 30V, Positive-QTOF	splash10-0159-0090000000-d4a04a50c394cba968e1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenamiphos 45V, Positive-QTOF	splash10-014i-0090000000-93cb423c35280cf6e7a7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenamiphos 15V, Positive-QTOF	splash10-0udi-0069000000-96078b842ad6c61e3d2a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenamiphos 90V, Positive-QTOF	splash10-0udi-5940000000-d70a968d944ba49dd1ce	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenamiphos 10V, Positive-QTOF	splash10-002r-1961000000-6a59a7d3929cb6c1f452	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenamiphos 20V, Positive-QTOF	splash10-001i-1390000000-87f8471e9c820add2e93	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenamiphos 40V, Positive-QTOF	splash10-000i-4900000000-26f0133ccf950f4cf465	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenamiphos 10V, Negative-QTOF	splash10-0zfs-4293000000-8d0f5c9a48d2dd05e238	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenamiphos 20V, Negative-QTOF	splash10-004i-2290000000-1a517cae8a7e665e46e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenamiphos 40V, Negative-QTOF	splash10-000b-7910000000-0b3532563157c053e6b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenamiphos 10V, Negative-QTOF	splash10-0udi-0129000000-c0cdb30129c325b775b6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenamiphos 20V, Negative-QTOF	splash10-0udi-0901000000-5cbc3028107c94f320c3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenamiphos 40V, Negative-QTOF	splash10-0udi-0910000000-6fc9bd5a7c66c0afa14b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenamiphos 10V, Positive-QTOF	splash10-0imi-0193000000-f9f9fe0b8a64c4666f70	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenamiphos 20V, Positive-QTOF	splash10-00or-0390000000-41b52eaec89c60dbd994	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenamiphos 40V, Positive-QTOF	splash10-052u-6930000000-918bc9e7576314e226bb	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB008460

KNApSAcK ID

Not Available

Chemspider ID

28827

KEGG Compound ID

C18659

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fenamiphos

METLIN ID

Not Available

PubChem Compound

31070

PDB ID

Not Available

ChEBI ID

38680

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Fenamiphos (HMDB0031787)

MOL for HMDB0031787 (Fenamiphos)

3D MOL for HMDB0031787 (Fenamiphos)

3D SDF for HMDB0031787 (Fenamiphos)

3D-SDF for HMDB0031787 (Fenamiphos)

PDB for HMDB0031787 (Fenamiphos)

3D PDB for HMDB0031787 (Fenamiphos)

SMILES for HMDB0031787 (Fenamiphos)

INCHI for HMDB0031787 (Fenamiphos)

Structure for HMDB0031787 (Fenamiphos)

3D Structure for HMDB0031787 (Fenamiphos)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra