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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:06:25 UTC

Update Date

2021-09-26 23:01:24 UTC

HMDB ID

HMDB0250131

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Chlorphenacil

Description

Chlorphenacil, also known as phenacid, belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom. Based on a literature review very few articles have been published on Chlorphenacil. This compound has been identified in human blood as reported by (PMID: 31557052 ). Chlorphenacil is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Chlorphenacil 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

HMDB0250131
     RDKit          3D
Chlorphenacil
 32 32  0  0  0  0  0  0  0  0999 V2000
    3.7253   -2.0222    0.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4461   -1.0235    0.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -1.1726    0.2985 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8884    0.2808   -0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046    0.2743   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710   -0.1143   -1.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2821   -0.0950   -1.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    0.3145   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8295    0.3702   -0.0556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7511    0.2655    1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3942   -0.3454    2.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9375   -0.3017    3.2811 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4583    0.7150   -1.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4024   -0.3242   -1.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -1.8958   -2.0046 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3426    0.7056    1.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7323    0.6821    0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4822   -0.4827    0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2014    0.9868    0.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2556    0.6275   -1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036   -0.4339   -2.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2354   -0.4107   -2.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563    1.2934    1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6552   -0.3415    0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6006    0.0542    2.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2474   -1.4391    2.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0476    1.6384   -1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6706    0.9429   -2.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6920   -0.0118   -2.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3582   -0.3526   -1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058    1.0836    1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2669    1.0018    1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  2  0
 17  5  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
M  END

  Mrv1652309112109062D          

 17 17  0  0  0  0            999 V2000
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -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
   -0.7145   -2.0625    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
   -1.4289   -3.3000    0.0000 C   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
   -0.7145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250131

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC1=CC=C(C=C1)N(CCCl)CCCl

> <INCHI_IDENTIFIER>
InChI=1S/C12H15Cl2NO2/c13-5-7-15(8-6-14)11-3-1-10(2-4-11)9-12(16)17/h1-4H,5-9H2,(H,16,17)

> <INCHI_KEY>
RQAFMLCWWGDNLI-UHFFFAOYSA-N

> <FORMULA>
C12H15Cl2NO2

> <MOLECULAR_WEIGHT>
276.16

> <EXACT_MASS>
275.0479841

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.920190095956205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{4-[bis(2-chloroethyl)amino]phenyl}acetic acid

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
3.0480176519999995

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.515041014884568

> <JCHEM_PKA_STRONGEST_BASIC>
1.6848904413114092

> <JCHEM_POLAR_SURFACE_AREA>
40.54

> <JCHEM_REFRACTIVITY>
70.48080000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{4-[bis(2-chloroethyl)amino]phenyl}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250131
     RDKit          3D
Chlorphenacil
 32 32  0  0  0  0  0  0  0  0999 V2000
    3.7253   -2.0222    0.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4461   -1.0235    0.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -1.1726    0.2985 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8884    0.2808   -0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046    0.2743   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710   -0.1143   -1.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2821   -0.0950   -1.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    0.3145   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8295    0.3702   -0.0556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7511    0.2655    1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3942   -0.3454    2.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9375   -0.3017    3.2811 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4583    0.7150   -1.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4024   -0.3242   -1.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -1.8958   -2.0046 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3426    0.7056    1.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7323    0.6821    0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4822   -0.4827    0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2014    0.9868    0.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2556    0.6275   -1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036   -0.4339   -2.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2354   -0.4107   -2.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563    1.2934    1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6552   -0.3415    0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6006    0.0542    2.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2474   -1.4391    2.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0476    1.6384   -1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6706    0.9429   -2.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6920   -0.0118   -2.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3582   -0.3526   -1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058    1.0836    1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2669    1.0018    1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  2  0
 17  5  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -1.540   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      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -8.470   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000  -6.160   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -2.667   0.000   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0      -5.335   3.080   0.000  0.00  0.00          Cl+0
HETATM   15  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       0.000   3.080   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    3   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0250131
HETATM    1  O1  UNL     1       3.725  -2.022   0.453  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.446  -1.024   0.214  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.817  -1.173   0.298  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.888   0.281  -0.146  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.405   0.274  -0.179  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.671  -0.114  -1.251  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.282  -0.095  -1.192  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.430   0.315  -0.058  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.830   0.370  -0.056  1.00  0.00           N  
HETATM   10  C7  UNL     1      -2.751   0.266   1.003  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.394  -0.345   2.303  1.00  0.00           C  
HETATM   12 CL1  UNL     1      -3.938  -0.302   3.281  1.00  0.00          CL  
HETATM   13  C9  UNL     1      -2.458   0.715  -1.361  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.402  -0.324  -1.840  1.00  0.00           C  
HETATM   15 CL2  UNL     1      -2.647  -1.896  -2.005  1.00  0.00          CL  
HETATM   16  C11 UNL     1       0.343   0.706   1.013  1.00  0.00           C  
HETATM   17  C12 UNL     1       1.732   0.682   0.947  1.00  0.00           C  
HETATM   18  H1  UNL     1       6.482  -0.483   0.024  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.201   0.987   0.678  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.256   0.627  -1.130  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.204  -0.434  -2.139  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.235  -0.411  -2.088  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.256   1.293   1.189  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.655  -0.341   0.630  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.601   0.054   2.900  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.247  -1.439   2.126  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.048   1.638  -1.132  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.671   0.943  -2.066  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.692  -0.012  -2.897  1.00  0.00           H  
HETATM   30  H13 UNL     1      -4.358  -0.353  -1.264  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.106   1.084   1.917  1.00  0.00           H  
HETATM   32  H15 UNL     1       2.267   1.002   1.829  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   18
CONECT    4    5   19   20
CONECT    5    6    6   17
CONECT    6    7   21
CONECT    7    8    8   22
CONECT    8    9   16
CONECT    9   10   13
CONECT   10   11   23   24
CONECT   11   12   25   26
CONECT   13   14   27   28
CONECT   14   15   29   30
CONECT   16   17   17   31
CONECT   17   32
END

HMDB0250131
     RDKit          3D
Chlorphenacil
 32 32  0  0  0  0  0  0  0  0999 V2000
    3.7253   -2.0222    0.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4461   -1.0235    0.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -1.1726    0.2985 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8884    0.2808   -0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046    0.2743   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710   -0.1143   -1.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2821   -0.0950   -1.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    0.3145   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8295    0.3702   -0.0556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7511    0.2655    1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3942   -0.3454    2.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9375   -0.3017    3.2811 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4583    0.7150   -1.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4024   -0.3242   -1.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -1.8958   -2.0046 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3426    0.7056    1.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7323    0.6821    0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4822   -0.4827    0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2014    0.9868    0.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2556    0.6275   -1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036   -0.4339   -2.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2354   -0.4107   -2.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563    1.2934    1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6552   -0.3415    0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6006    0.0542    2.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2474   -1.4391    2.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0476    1.6384   -1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6706    0.9429   -2.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6920   -0.0118   -2.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3582   -0.3526   -1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058    1.0836    1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2669    1.0018    1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  2  0
 17  5  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-{4-[bis(2-chloroethyl)amino]phenyl}acetate	HMDB
4-(N,N-Bis(2-chloroethyl)amino)phenylacetic acid	HMDB
Chlorphenacyl	HMDB
p-(N,N-Bis(2-chloroethyl)amino)phenylacetic acid	HMDB
Phenacid	HMDB
Phenacid, sodium salt	HMDB
Phenylacetic mustard	HMDB

Chemical Formula

C₁₂H₁₅Cl₂NO₂

Average Molecular Weight

276.16

Monoisotopic Molecular Weight

275.0479841

IUPAC Name

2-{4-[bis(2-chloroethyl)amino]phenyl}acetic acid

Traditional Name

{4-[bis(2-chloroethyl)amino]phenyl}acetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC1=CC=C(C=C1)N(CCCl)CCCl

InChI Identifier

InChI=1S/C12H15Cl2NO2/c13-5-7-15(8-6-14)11-3-1-10(2-4-11)9-12(16)17/h1-4H,5-9H2,(H,16,17)

InChI Key

RQAFMLCWWGDNLI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Nitrogen mustard compounds

Direct Parent

Nitrogen mustard compounds

Alternative Parents

Substituents

Aniline or substituted anilines
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Nitrogen mustard
Monocyclic benzene moiety
Benzenoid
Amino acid or derivatives
Amino acid
Tertiary amine
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alkyl chloride
Organohalogen compound
Organochloride
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Alkyl halide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

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	1.6	ALOGPS
logP	3.05	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.52	ChemAxon
pKa (Strongest Basic)	1.68	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	70.48 m³·mol⁻¹	ChemAxon
Polarizability	27.92 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]+	157.004	30932474
DeepCCS	[M-H]-	154.61	30932474
DeepCCS	[M-2H]-	187.736	30932474
DeepCCS	[M+Na]+	163.061	30932474
AllCCS	[M+H]+	156.2	32859911
AllCCS	[M+H-H2O]+	153.0	32859911
AllCCS	[M+NH4]+	159.1	32859911
AllCCS	[M+Na]+	159.9	32859911
AllCCS	[M-H]-	156.4	32859911
AllCCS	[M+Na-2H]-	156.8	32859911
AllCCS	[M+HCOO]-	157.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chlorphenacil	OC(=O)CC1=CC=C(C=C1)N(CCCl)CCCl	3368.9	Standard polar	33892256
Chlorphenacil	OC(=O)CC1=CC=C(C=C1)N(CCCl)CCCl	2290.9	Standard non polar	33892256
Chlorphenacil	OC(=O)CC1=CC=C(C=C1)N(CCCl)CCCl	2294.5	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 - Chlorphenacil GC-MS (Non-derivatized) - 70eV, Positive	splash10-02cr-1940000000-747722abb43f60d179b7	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorphenacil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorphenacil GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorphenacil GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenacil 10V, Positive-QTOF	splash10-004i-0090000000-29d5ff156fc06c139ac8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenacil 20V, Positive-QTOF	splash10-004i-0390000000-003113acec8cd830a2d4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenacil 40V, Positive-QTOF	splash10-02di-2900000000-c86191622c972675938c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenacil 10V, Negative-QTOF	splash10-001i-9550000000-5b66f851e7e21df0f411	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenacil 20V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenacil 40V, Negative-QTOF	splash10-001i-9000000000-5f288bd9d9a67b05a6fd	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

23639

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25306

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Chlorphenacil (HMDB0250131)

MOL for HMDB0250131 (Chlorphenacil)

3D MOL for HMDB0250131 (Chlorphenacil)

3D SDF for HMDB0250131 (Chlorphenacil)

3D-SDF for HMDB0250131 (Chlorphenacil)

PDB for HMDB0250131 (Chlorphenacil)

3D PDB for HMDB0250131 (Chlorphenacil)

SMILES for HMDB0250131 (Chlorphenacil)

INCHI for HMDB0250131 (Chlorphenacil)

Structure for HMDB0250131 (Chlorphenacil)

3D Structure for HMDB0250131 (Chlorphenacil)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra