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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:06:09 UTC

Update Date

2021-09-26 23:02:41 UTC

HMDB ID

HMDB0250945

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dehydrochloramphenicol

Description

Dehydrochloramphenicol, also known as DH-CAP, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review a significant number of articles have been published on Dehydrochloramphenicol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dehydrochloramphenicol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dehydrochloramphenicol 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

HMDB0250945
     RDKit          3D
Dehydrochloramphenicol
 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.1199   -2.1062   -0.6224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5602   -0.9939   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6892    0.1256   -0.3107 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3050   -0.0286   -0.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    0.8931   -2.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548    0.9335   -2.6882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3851    0.3965    0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8607    1.0143    1.2372 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0494    0.1672    0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6946   -0.5940   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0795   -0.7477   -0.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.1732    0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -0.3496    0.3816 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.9845    0.1461    1.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8749   -1.1077   -0.5962 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.2068    0.5959    1.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8407    0.7471    1.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9478   -0.9102    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9385   -0.2627    1.9238 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.9808    0.0952   -0.8057 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0542    1.0458    0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886   -1.0494   -1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0164    0.5340   -2.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5499    1.9012   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    1.6913   -2.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1210   -1.0804   -1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5503   -1.3526   -1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8227    1.0450    2.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3752    1.3514    1.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3871   -1.9269    0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  2  0
  2 18  1  0
 18 19  1  0
 18 20  1  0
 17  9  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
 10 26  1  0
 11 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
M  CHG  2  13   1  15  -1
M  END


  Mrv1652309112110062D          

 20 20  0  0  0  0            999 V2000
    1.6204   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    1.5395    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    0.1105    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -0.6039    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.8546   -1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    0.1105    0.0000 O   0  5  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  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  CHG  2  18   1  20  -1
M  END
> <DATABASE_ID>
HMDB0250945

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC(NC(=O)C(Cl)Cl)C(=O)C1=CC=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H10Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8,10,16H,5H2,(H,14,18)

> <INCHI_KEY>
ZMCQNNUYRHSMAB-UHFFFAOYSA-N

> <FORMULA>
C11H10Cl2N2O5

> <MOLECULAR_WEIGHT>
321.11

> <EXACT_MASS>
319.9966768

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
27.57532597279561

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2-dichloro-N-[3-hydroxy-1-(4-nitrophenyl)-1-oxopropan-2-yl]acetamide

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
1.1689768876666666

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.770914868574337

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.988155271963119

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8296308281780833

> <JCHEM_POLAR_SURFACE_AREA>
109.54000000000002

> <JCHEM_REFRACTIVITY>
71.59819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2-dichloro-N-[3-hydroxy-1-(4-nitrophenyl)-1-oxopropan-2-yl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250945
     RDKit          3D
Dehydrochloramphenicol
 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.1199   -2.1062   -0.6224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5602   -0.9939   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6892    0.1256   -0.3107 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3050   -0.0286   -0.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    0.8931   -2.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548    0.9335   -2.6882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3851    0.3965    0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8607    1.0143    1.2372 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0494    0.1672    0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6946   -0.5940   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0795   -0.7477   -0.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.1732    0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -0.3496    0.3816 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.9845    0.1461    1.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8749   -1.1077   -0.5962 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.2068    0.5959    1.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8407    0.7471    1.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9478   -0.9102    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9385   -0.2627    1.9238 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.9808    0.0952   -0.8057 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0542    1.0458    0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886   -1.0494   -1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0164    0.5340   -2.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5499    1.9012   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    1.6913   -2.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1210   -1.0804   -1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5503   -1.3526   -1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8227    1.0450    2.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3752    1.3514    1.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3871   -1.9269    0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  2  0
  2 18  1  0
 18 19  1  0
 18 20  1  0
 17  9  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
 10 26  1  0
 11 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
M  CHG  2  13   1  15  -1
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       3.025  -2.461   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.485  -2.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.715  -1.127   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.485   0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.025   0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.795  -1.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -1.127   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.105  -2.461   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.105   0.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.105   2.874   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       7.645   0.206   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       8.415   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.645   2.874   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.955   1.540   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0      10.725   2.874   0.000  0.00  0.00          Cl+0
HETATM   17 Cl   UNK     0      10.725   0.206   0.000  0.00  0.00          Cl+0
HETATM   18  N   UNK     0      -0.825  -1.127   0.000  0.00  0.00           N+1
HETATM   19  O   UNK     0      -1.595  -2.461   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.595   0.206   0.000  0.00  0.00           O-1
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    3   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0250945
HETATM    1  O1  UNL     1      -3.120  -2.106  -0.622  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.560  -0.994  -0.241  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.689   0.126  -0.311  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.305  -0.029  -0.821  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.241   0.893  -2.035  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.055   0.934  -2.688  1.00  0.00           O  
HETATM    7  C4  UNL     1      -0.385   0.397   0.239  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.861   1.014   1.237  1.00  0.00           O  
HETATM    9  C5  UNL     1       1.049   0.167   0.250  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.695  -0.594  -0.697  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.080  -0.748  -0.634  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.860  -0.173   0.339  1.00  0.00           C  
HETATM   13  N2  UNL     1       5.279  -0.350   0.382  1.00  0.00           N1+
HETATM   14  O4  UNL     1       5.985   0.146   1.255  1.00  0.00           O  
HETATM   15  O5  UNL     1       5.875  -1.108  -0.596  1.00  0.00           O1-
HETATM   16  C9  UNL     1       3.207   0.596   1.295  1.00  0.00           C  
HETATM   17  C10 UNL     1       1.841   0.747   1.233  1.00  0.00           C  
HETATM   18  C11 UNL     1      -4.948  -0.910   0.255  1.00  0.00           C  
HETATM   19 CL1  UNL     1      -4.938  -0.263   1.924  1.00  0.00          CL  
HETATM   20 CL2  UNL     1      -5.981   0.095  -0.806  1.00  0.00          CL  
HETATM   21  H1  UNL     1      -3.054   1.046   0.004  1.00  0.00           H  
HETATM   22  H2  UNL     1      -1.189  -1.049  -1.158  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.016   0.534  -2.766  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.550   1.901  -1.682  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.541   1.691  -2.468  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.121  -1.080  -1.468  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.550  -1.353  -1.396  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.823   1.045   2.055  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.375   1.351   1.991  1.00  0.00           H  
HETATM   30  H10 UNL     1      -5.387  -1.927   0.230  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   18
CONECT    3    4   21
CONECT    4    5    7   22
CONECT    5    6   23   24
CONECT    6   25
CONECT    7    8    8    9
CONECT    9   10   10   17
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   13   16
CONECT   13   14   14   15
CONECT   16   17   17   28
CONECT   17   29
CONECT   18   19   20   30
END

HMDB0250945
     RDKit          3D
Dehydrochloramphenicol
 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.1199   -2.1062   -0.6224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5602   -0.9939   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6892    0.1256   -0.3107 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3050   -0.0286   -0.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    0.8931   -2.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548    0.9335   -2.6882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3851    0.3965    0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8607    1.0143    1.2372 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0494    0.1672    0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6946   -0.5940   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0795   -0.7477   -0.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.1732    0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -0.3496    0.3816 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.9845    0.1461    1.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8749   -1.1077   -0.5962 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.2068    0.5959    1.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8407    0.7471    1.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9478   -0.9102    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9385   -0.2627    1.9238 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.9808    0.0952   -0.8057 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0542    1.0458    0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886   -1.0494   -1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0164    0.5340   -2.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5499    1.9012   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    1.6913   -2.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1210   -1.0804   -1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5503   -1.3526   -1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8227    1.0450    2.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3752    1.3514    1.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3871   -1.9269    0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  2  0
  2 18  1  0
 18 19  1  0
 18 20  1  0
 17  9  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
 10 26  1  0
 11 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
M  CHG  2  13   1  15  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
DH-CAP	MeSH

Chemical Formula

C₁₁H₁₀Cl₂N₂O₅

Average Molecular Weight

321.11

Monoisotopic Molecular Weight

319.9966768

IUPAC Name

2,2-dichloro-N-[3-hydroxy-1-(4-nitrophenyl)-1-oxopropan-2-yl]acetamide

Traditional Name

2,2-dichloro-N-[3-hydroxy-1-(4-nitrophenyl)-1-oxopropan-2-yl]acetamide

CAS Registry Number

Not Available

SMILES

OCC(NC(=O)C(Cl)Cl)C(=O)C1=CC=C(C=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C11H10Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8,10,16H,5H2,(H,14,18)

InChI Key

ZMCQNNUYRHSMAB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Nitrobenzene
Nitroaromatic compound
Benzoyl
Aryl alkyl ketone
Monocyclic benzene moiety
Beta-hydroxy ketone
Benzenoid
Carboxamide group
C-nitro compound
Secondary carboxylic acid amide
Organic nitro compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Organic oxoazanium
Organic zwitterion
Organochloride
Organohalogen compound
Hydrocarbon derivative
Alkyl chloride
Organonitrogen compound
Alcohol
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Primary alcohol
Alkyl halide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.1	ALOGPS
logP	1.17	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.99	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.54 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	71.6 m³·mol⁻¹	ChemAxon
Polarizability	27.58 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]+	163.495	30932474
DeepCCS	[M-H]-	160.255	30932474
DeepCCS	[M-2H]-	195.515	30932474
DeepCCS	[M+Na]+	171.704	30932474
AllCCS	[M+H]+	164.4	32859911
AllCCS	[M+H-H2O]+	161.3	32859911
AllCCS	[M+NH4]+	167.3	32859911
AllCCS	[M+Na]+	168.1	32859911
AllCCS	[M-H]-	163.7	32859911
AllCCS	[M+Na-2H]-	163.8	32859911
AllCCS	[M+HCOO]-	164.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydrochloramphenicol	OCC(NC(=O)C(Cl)Cl)C(=O)C1=CC=C(C=C1)[N+]([O-])=O	3630.9	Standard polar	33892256
Dehydrochloramphenicol	OCC(NC(=O)C(Cl)Cl)C(=O)C1=CC=C(C=C1)[N+]([O-])=O	2427.4	Standard non polar	33892256
Dehydrochloramphenicol	OCC(NC(=O)C(Cl)Cl)C(=O)C1=CC=C(C=C1)[N+]([O-])=O	2505.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydrochloramphenicol,2TMS,isomer #1	C[Si](C)(C)OCC(C(=O)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C	2470.7	Semi standard non polar	33892256
Dehydrochloramphenicol,2TMS,isomer #1	C[Si](C)(C)OCC(C(=O)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C	2559.6	Standard non polar	33892256
Dehydrochloramphenicol,2TMS,isomer #1	C[Si](C)(C)OCC(C(=O)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C	3145.2	Standard polar	33892256
Dehydrochloramphenicol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(C(=O)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C(C)(C)C	3040.8	Semi standard non polar	33892256
Dehydrochloramphenicol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(C(=O)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C(C)(C)C	2995.8	Standard non polar	33892256
Dehydrochloramphenicol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(C(=O)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C(C)(C)C	3248.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrochloramphenicol GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9821000000-ae0818c57a54c14f7fbc	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrochloramphenicol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrochloramphenicol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrochloramphenicol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrochloramphenicol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrochloramphenicol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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

21134

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22536

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 Dehydrochloramphenicol (HMDB0250945)

MOL for HMDB0250945 (Dehydrochloramphenicol)

3D MOL for HMDB0250945 (Dehydrochloramphenicol)

3D SDF for HMDB0250945 (Dehydrochloramphenicol)

3D-SDF for HMDB0250945 (Dehydrochloramphenicol)

PDB for HMDB0250945 (Dehydrochloramphenicol)

3D PDB for HMDB0250945 (Dehydrochloramphenicol)

SMILES for HMDB0250945 (Dehydrochloramphenicol)

INCHI for HMDB0250945 (Dehydrochloramphenicol)

Structure for HMDB0250945 (Dehydrochloramphenicol)

3D Structure for HMDB0250945 (Dehydrochloramphenicol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra