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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:24:05 UTC

Update Date

2021-09-26 23:02:55 UTC

HMDB ID

HMDB0251098

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dextramycin

Description

Tyfomycine, also known as levoplast or levosin, belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. Tyfomycine is an extremely weak basic (essentially neutral) compound (based on its pKa). High-level resistance is conferred by the cat-gene; this gene codes for an enzyme called chloramphenicol acetyltransferase, which inactivates chloramphenicol by covalently linking one or two acetyl groups, derived from acetyl-S-coenzyme A, to the hydroxyl groups on the chloramphenicol molecule. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dextramycin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dextramycin 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

HMDB0251098
     RDKit          3D
Dextramycin
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.1910    1.2241   -1.4932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4954    0.9909   -0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5677    0.3448    0.5337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2442   -0.0661    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1502   -1.5536    0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802   -2.0537   -0.1729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069    0.6678    0.9094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4537    2.0363    0.6974 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1666    0.2971    0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7004    0.7465   -0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9987    0.3944   -1.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -0.4093   -0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0659   -0.7709   -0.5847 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.7789   -1.4867    0.1243 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063   -0.3257   -1.7734 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.2412   -0.8728    0.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9595   -0.5153    1.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8162    1.3902    0.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7625    2.1838   -1.0968 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.7557   -0.0356    0.7653 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8238    0.1495    1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1184    0.2000   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173   -2.0170   -0.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2747   -1.8500    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0097   -3.0443   -0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3603    0.4112    1.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4313    2.1542   -0.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1411    1.3808   -1.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4385    0.7342   -1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8592   -1.5041    1.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -0.8638    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7497    2.0632    1.0968 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  1  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
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  CHG  2  13   1  15  -1
M  END

  Mrv1533004161505192D          

 20 20  0  0  0  0            999 V2000
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 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>
HMDB0251098

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)

> <INCHI_KEY>
WIIZWVCIJKGZOK-UHFFFAOYSA-N

> <FORMULA>
C11H12Cl2N2O5

> <MOLECULAR_WEIGHT>
323.13

> <EXACT_MASS>
322.0123269

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.58108854847767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
0.8787034880000002

> <ALOGPS_LOGS>
-2.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.549720884233661

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.390375580724093

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7948502347233966

> <JCHEM_POLAR_SURFACE_AREA>
112.70000000000002

> <JCHEM_REFRACTIVITY>
72.1965

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cloranfenicol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251098
     RDKit          3D
Dextramycin
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.1910    1.2241   -1.4932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4954    0.9909   -0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5677    0.3448    0.5337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2442   -0.0661    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1502   -1.5536    0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802   -2.0537   -0.1729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069    0.6678    0.9094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4537    2.0363    0.6974 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1666    0.2971    0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7004    0.7465   -0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9987    0.3944   -1.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -0.4093   -0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0659   -0.7709   -0.5847 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.7789   -1.4867    0.1243 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063   -0.3257   -1.7734 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.2412   -0.8728    0.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9595   -0.5153    1.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8162    1.3902    0.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7625    2.1838   -1.0968 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.7557   -0.0356    0.7653 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8238    0.1495    1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1184    0.2000   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173   -2.0170   -0.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2747   -1.8500    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0097   -3.0443   -0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3603    0.4112    1.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4313    2.1542   -0.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1411    1.3808   -1.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4385    0.7342   -1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8592   -1.5041    1.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -0.8638    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7497    2.0632    1.0968 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  1  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
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  CHG  2  13   1  15  -1
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       6.668  -6.930   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       2.667  -7.700   0.000  0.00  0.00          Cl+0
HETATM    9 Cl   UNK     0       4.001  -5.390   0.000  0.00  0.00          Cl+0
HETATM   10  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      14.670 -10.010   0.000  0.00  0.00           N+1
HETATM   19  O   UNK     0      16.004  -9.240   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.670 -11.550   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0251098
HETATM    1  O1  UNL     1      -3.191   1.224  -1.493  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.495   0.991  -0.308  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.568   0.345   0.534  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.244  -0.066   0.057  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.150  -1.554   0.252  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.080  -2.054  -0.173  1.00  0.00           O  
HETATM    7  C4  UNL     1      -0.207   0.668   0.909  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.454   2.036   0.697  1.00  0.00           O  
HETATM    9  C5  UNL     1       1.167   0.297   0.513  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.700   0.746  -0.678  1.00  0.00           C  
HETATM   11  C7  UNL     1       2.999   0.394  -1.050  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.740  -0.409  -0.208  1.00  0.00           C  
HETATM   13  N2  UNL     1       5.066  -0.771  -0.585  1.00  0.00           N1+
HETATM   14  O4  UNL     1       5.779  -1.487   0.124  1.00  0.00           O  
HETATM   15  O5  UNL     1       5.606  -0.326  -1.773  1.00  0.00           O1-
HETATM   16  C9  UNL     1       3.241  -0.873   0.980  1.00  0.00           C  
HETATM   17  C10 UNL     1       1.959  -0.515   1.330  1.00  0.00           C  
HETATM   18  C11 UNL     1      -4.816   1.390   0.203  1.00  0.00           C  
HETATM   19 CL1  UNL     1      -5.763   2.184  -1.097  1.00  0.00          CL  
HETATM   20 CL2  UNL     1      -5.756  -0.036   0.765  1.00  0.00          CL  
HETATM   21  H1  UNL     1      -2.824   0.149   1.528  1.00  0.00           H  
HETATM   22  H2  UNL     1      -1.118   0.200  -0.990  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.917  -2.017  -0.398  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.275  -1.850   1.299  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.010  -3.044  -0.167  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.360   0.411   1.977  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.431   2.154  -0.305  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.141   1.381  -1.361  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.438   0.734  -1.978  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.859  -1.504   1.614  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.534  -0.864   2.263  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.750   2.063   1.097  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    9   26
CONECT    8   27
CONECT    9   10   10   17
CONECT   10   11   28
CONECT   11   12   12   29
CONECT   12   13   16
CONECT   13   14   14   15
CONECT   16   17   17   30
CONECT   17   31
CONECT   18   19   20   32
END

HMDB0251098
     RDKit          3D
Dextramycin
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.1910    1.2241   -1.4932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4954    0.9909   -0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5677    0.3448    0.5337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2442   -0.0661    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1502   -1.5536    0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802   -2.0537   -0.1729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069    0.6678    0.9094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4537    2.0363    0.6974 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1666    0.2971    0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7004    0.7465   -0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9987    0.3944   -1.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -0.4093   -0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0659   -0.7709   -0.5847 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.7789   -1.4867    0.1243 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063   -0.3257   -1.7734 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.2412   -0.8728    0.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9595   -0.5153    1.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8162    1.3902    0.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7625    2.1838   -1.0968 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.7557   -0.0356    0.7653 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8238    0.1495    1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1184    0.2000   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173   -2.0170   -0.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2747   -1.8500    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0097   -3.0443   -0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3603    0.4112    1.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4313    2.1542   -0.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1411    1.3808   -1.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4385    0.7342   -1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8592   -1.5041    1.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -0.8638    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7497    2.0632    1.0968 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  1  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
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  CHG  2  13   1  15  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Levoplast	MeSH
Levosin	MeSH
2,2-Dichloro-N-[1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]ethanimidate	Generator

Chemical Formula

C₁₁H₁₂Cl₂N₂O₅

Average Molecular Weight

323.13

Monoisotopic Molecular Weight

322.0123269

IUPAC Name

2,2-dichloro-N-[1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide

Traditional Name

cloranfenicol

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/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)

InChI Key

WIIZWVCIJKGZOK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Nitrobenzenes

Direct Parent

Nitrobenzenes

Alternative Parents

Substituents

Nitrobenzene
Nitroaromatic compound
Carboxamide group
C-nitro compound
Secondary alcohol
Secondary carboxylic acid amide
Organic nitro compound
Carboxylic acid derivative
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organochloride
Alkyl chloride
Organohalogen compound
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Aromatic alcohol
Organic zwitterion
Alkyl halide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

a small molecule (CHLORAMPHENICOL )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	1.15	ALOGPS
logP	0.88	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	10.39	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	112.7 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	72.2 m³·mol⁻¹	ChemAxon
Polarizability	28.58 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]+	164.6	30932474
DeepCCS	[M-H]-	161.34	30932474
DeepCCS	[M-2H]-	196.716	30932474
DeepCCS	[M+Na]+	172.981	30932474
AllCCS	[M+H]+	166.1	32859911
AllCCS	[M+H-H2O]+	163.1	32859911
AllCCS	[M+NH4]+	168.9	32859911
AllCCS	[M+Na]+	169.7	32859911
AllCCS	[M-H]-	164.7	32859911
AllCCS	[M+Na-2H]-	164.9	32859911
AllCCS	[M+HCOO]-	165.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dextramycin	OCC(NC(=O)C(Cl)Cl)C(O)C1=CC=C(C=C1)[N+]([O-])=O	3704.8	Standard polar	33892256
Dextramycin	OCC(NC(=O)C(Cl)Cl)C(O)C1=CC=C(C=C1)[N+]([O-])=O	2577.8	Standard non polar	33892256
Dextramycin	OCC(NC(=O)C(Cl)Cl)C(O)C1=CC=C(C=C1)[N+]([O-])=O	2594.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dextramycin,3TMS,isomer #1	C[Si](C)(C)OCC(C(O[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C	2496.6	Semi standard non polar	33892256
Dextramycin,3TMS,isomer #1	C[Si](C)(C)OCC(C(O[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C	2501.3	Standard non polar	33892256
Dextramycin,3TMS,isomer #1	C[Si](C)(C)OCC(C(O[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C	2918.0	Standard polar	33892256
Dextramycin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(C(O[Si](C)(C)C(C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C(C)(C)C	3258.6	Semi standard non polar	33892256
Dextramycin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(C(O[Si](C)(C)C(C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C(C)(C)C	3127.8	Standard non polar	33892256
Dextramycin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(C(O[Si](C)(C)C(C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C(C)(C)C	3132.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dextramycin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-3900000000-2ba6754ba027027454d1	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextramycin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextramycin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextramycin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextramycin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextramycin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextramycin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextramycin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextramycin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextramycin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextramycin GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextramycin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextramycin GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextramycin GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-11di-9600000000-b788be55b33929ea9fbf	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 - Dextramycin 30V, Negative-QTOF	splash10-0udi-0900000000-acaba4305e49df988fee	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dextramycin 20V, Positive-QTOF	splash10-00fr-0290000000-7e2489a0a994948235fa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dextramycin 20V, Negative-QTOF	splash10-0udi-0900000000-7df54c2602ac23cd6c06	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dextramycin 10V, Negative-QTOF	splash10-0kmi-0956000000-13bbb028d904da4bdb3d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dextramycin 40V, Positive-QTOF	splash10-014i-0910000000-cc8e4729483c91bc670b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dextramycin 40V, Negative-QTOF	splash10-0uk9-0900000000-d95c08e7bb859c392b3d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dextramycin 10V, Positive-QTOF	splash10-0a4i-0059000000-a9e3ef5ee191b48d1c6c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dextramycin 50V, Positive-QTOF	splash10-014i-0900000000-ce1237f08f9d2bc030a0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dextramycin 20V, Positive-QTOF	splash10-00fr-0290000000-77d6e9c5aa8aa67ce075	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dextramycin 30V, Positive-QTOF	splash10-066r-0980000000-00e08722a8bf479c347a	2021-09-20	HMDB team, MONA	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chloramphenicol

METLIN ID

Not Available

PubChem Compound

298

PDB ID

Not Available

ChEBI ID

94390

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 Dextramycin (HMDB0251098)

MOL for HMDB0251098 (Dextramycin)

3D MOL for HMDB0251098 (Dextramycin)

3D SDF for HMDB0251098 (Dextramycin)

3D-SDF for HMDB0251098 (Dextramycin)

PDB for HMDB0251098 (Dextramycin)

3D PDB for HMDB0251098 (Dextramycin)

SMILES for HMDB0251098 (Dextramycin)

INCHI for HMDB0251098 (Dextramycin)

Structure for HMDB0251098 (Dextramycin)

3D Structure for HMDB0251098 (Dextramycin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra