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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6)transporters (1) Show 7 proteins XML

enzymes (6)transporters (1) Show 7 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014589

Secondary Accession Numbers

HMDB14589

Metabolite Identification

Common Name

Chloramphenicol

Description

Chloramphenicol, also known as chloromycetin or chloramex, 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. Chloramphenicol is a drug which is used in treatment of cholera, as it destroys the vibrios and decreases the diarrhea. it is effective against tetracycline-resistant vibrios. it is also used in eye drops or ointment to treat bacterial conjunctivitis. Drug therapy is discontinued immediately; exchange transfusion may be required to remove the drug. Chloramphenicol is an extremely weak basic (essentially neutral) compound (based on its pKa). Chloramphenicol exists in all living organisms, ranging from bacteria to humans. An antibiotic first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. In humans, chloramphenicol is involved in chloramphenicol action pathway. Chloramphenicol is formally rated as a probable carcinogen (by IARC 2A) and is also a potentially toxic compound. Chloramphenicol targets the large 39S subunit of the mitochondrial ribosome thereby deactivation mitochondrial protein synthesis. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic.

Structure

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

HMDB0014589
     RDKit          3D
Chloramphenicol
 32 32  0  0  0  0  0  0  0  0999 V2000
   -1.6286    1.2226   -2.3306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1125    1.2527   -1.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188    0.1987   -0.2926 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1743   -1.0161   -0.5439 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1747   -2.1828   -0.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0260   -1.9122   -1.7615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2167   -1.4012    0.5222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8657   -1.6014    1.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9846   -0.5827    0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8473   -0.8003    1.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984   -0.0620    1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159    0.9306    0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217    1.7145    1.1467 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.7446    2.5934    0.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3560    1.4864    2.1890 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.4692    1.1606   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3262    0.4092   -0.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8985    2.4376   -0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947    3.2635    0.6222 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1348    3.5643   -2.1455 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3418    0.2541    0.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6565   -0.9849   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6062   -3.1114   -0.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7486   -2.2019    0.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4361   -2.7139   -2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1412   -2.4420    0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3788   -2.2854    2.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6060   -1.5853    2.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6743   -0.2321    2.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474    1.9504   -0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030    0.6195   -1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9223    2.0575   -0.5031 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  6
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  6
  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


  Mrv0541 04191212122D          

 20 20  0  0  1  0            999 V2000
   -0.7145    0.4125    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
    0.0000   -0.8250    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    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    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
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  2  7  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  6  2  0  0  0  0
  5  6  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  1  0  0  0
  8 10  1  0  0  0  0
  8 11  1  6  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 15  1  0  0  0  0
 12 16  2  0  0  0  0
 14 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  1  0  0  0  0
 15 20  1  0  0  0  0
M  CHG  2  14   1  17  -1
M  END
> <DATABASE_ID>
HMDB0014589

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@@H](NC(=O)C(Cl)Cl)[C@H](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)/t8-,9-/m1/s1

> <INCHI_KEY>
WIIZWVCIJKGZOK-RKDXNWHRSA-N

> <FORMULA>
C11H12Cl2N2O5

> <MOLECULAR_WEIGHT>
323.129

> <EXACT_MASS>
322.012326918

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.083065806597737

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2-dichloro-N-[(1R,2R)-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>
13.587750033412025

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.494317415220007

> <JCHEM_PKA_STRONGEST_BASIC>
-2.79485022158514

> <JCHEM_POLAR_SURFACE_AREA>
115.37999999999997

> <JCHEM_REFRACTIVITY>
73.2007

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chloramphenicol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014589
     RDKit          3D
Chloramphenicol
 32 32  0  0  0  0  0  0  0  0999 V2000
   -1.6286    1.2226   -2.3306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1125    1.2527   -1.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188    0.1987   -0.2926 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1743   -1.0161   -0.5439 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1747   -2.1828   -0.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0260   -1.9122   -1.7615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2167   -1.4012    0.5222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8657   -1.6014    1.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9846   -0.5827    0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8473   -0.8003    1.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984   -0.0620    1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159    0.9306    0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217    1.7145    1.1467 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.7446    2.5934    0.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3560    1.4864    2.1890 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.4692    1.1606   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3262    0.4092   -0.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8985    2.4376   -0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947    3.2635    0.6222 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1348    3.5643   -2.1455 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3418    0.2541    0.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6565   -0.9849   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6062   -3.1114   -0.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7486   -2.2019    0.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4361   -2.7139   -2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1412   -2.4420    0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3788   -2.2854    2.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6060   -1.5853    2.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6743   -0.2321    2.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474    1.9504   -0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030    0.6195   -1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9223    2.0575   -0.5031 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  6
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  6
  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                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      -5.335  -1.540   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+1
HETATM   15  C   UNK     0      -8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.668   0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   19 Cl   UNK     0      -8.002  -3.080   0.000  0.00  0.00          Cl+0
HETATM   20 Cl   UNK     0      -9.336  -0.770   0.000  0.00  0.00          Cl+0
CONECT    1    2    4                                                       
CONECT    2    1    7    3                                                  
CONECT    3    2    5                                                       
CONECT    4    1    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   14                                                  
CONECT    7    2    8    9                                                  
CONECT    8    7   10   11                                                  
CONECT    9    7                                                            
CONECT   10    8   12                                                       
CONECT   11    8   13                                                       
CONECT   12   10   15   16                                                  
CONECT   13   11                                                            
CONECT   14    6   17   18                                                  
CONECT   15   12   19   20                                                  
CONECT   16   12                                                            
CONECT   17   14                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0014589
HETATM    1  O1  UNL     1      -1.629   1.223  -2.331  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.112   1.253  -1.180  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.919   0.199  -0.293  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.174  -1.016  -0.544  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.175  -2.183  -0.695  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.026  -1.912  -1.761  1.00  0.00           O  
HETATM    7  C4  UNL     1      -0.217  -1.401   0.522  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.866  -1.601   1.756  1.00  0.00           O  
HETATM    9  C5  UNL     1       0.985  -0.583   0.653  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.847  -0.800   1.709  1.00  0.00           C  
HETATM   11  C7  UNL     1       2.998  -0.062   1.880  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.316   0.931   0.979  1.00  0.00           C  
HETATM   13  N2  UNL     1       4.522   1.715   1.147  1.00  0.00           N1+
HETATM   14  O4  UNL     1       4.745   2.593   0.295  1.00  0.00           O  
HETATM   15  O5  UNL     1       5.356   1.486   2.189  1.00  0.00           O1-
HETATM   16  C9  UNL     1       2.469   1.161  -0.077  1.00  0.00           C  
HETATM   17  C10 UNL     1       1.326   0.409  -0.225  1.00  0.00           C  
HETATM   18  C11 UNL     1      -2.899   2.438  -0.780  1.00  0.00           C  
HETATM   19 CL1  UNL     1      -2.195   3.263   0.622  1.00  0.00          CL  
HETATM   20 CL2  UNL     1      -3.135   3.564  -2.145  1.00  0.00          CL  
HETATM   21  H1  UNL     1      -2.342   0.254   0.670  1.00  0.00           H  
HETATM   22  H2  UNL     1      -0.657  -0.985  -1.517  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.606  -3.111  -0.889  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.749  -2.202   0.245  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.436  -2.714  -2.139  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.141  -2.442   0.252  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.379  -2.285   2.294  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.606  -1.585   2.430  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.674  -0.232   2.707  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.747   1.950  -0.770  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.703   0.620  -1.058  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.922   2.058  -0.503  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

HMDB0014589
     RDKit          3D
Chloramphenicol
 32 32  0  0  0  0  0  0  0  0999 V2000
   -1.6286    1.2226   -2.3306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1125    1.2527   -1.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188    0.1987   -0.2926 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1743   -1.0161   -0.5439 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1747   -2.1828   -0.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0260   -1.9122   -1.7615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2167   -1.4012    0.5222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8657   -1.6014    1.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9846   -0.5827    0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8473   -0.8003    1.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984   -0.0620    1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159    0.9306    0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217    1.7145    1.1467 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.7446    2.5934    0.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3560    1.4864    2.1890 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.4692    1.1606   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3262    0.4092   -0.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8985    2.4376   -0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947    3.2635    0.6222 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1348    3.5643   -2.1455 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3418    0.2541    0.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6565   -0.9849   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6062   -3.1114   -0.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7486   -2.2019    0.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4361   -2.7139   -2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1412   -2.4420    0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3788   -2.2854    2.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6060   -1.5853    2.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6743   -0.2321    2.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474    1.9504   -0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030    0.6195   -1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9223    2.0575   -0.5031 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  6
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  6
  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
Chloramex	ChEBI
Chloramphenicolum	ChEBI
Chlornitromycin	ChEBI
Chlorocid	ChEBI
Chlorocol	ChEBI
Chloromycetin	ChEBI
Cloramfenicol	ChEBI
D-(-)-2,2-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenylethyl)acetamide	ChEBI
D-(-)-Threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propanediol	ChEBI
Fenicol	ChEBI
Globenicol	ChEBI
Halomycetin	ChEBI
Laevomycetinum	ChEBI
Levomicetina	ChEBI
Levomycetin	ChEBI
Oleomycetin	ChEBI
Sificetina	ChEBI
CP	Kegg
Amphicol	Kegg
Econochlor	Kegg
D-(-)-2,2-Dichloro-N-(b-hydroxy-a-(hydroxymethyl)-p-nitrophenylethyl)acetamide	Generator
D-(-)-2,2-Dichloro-N-(β-hydroxy-α-(hydroxymethyl)-p-nitrophenylethyl)acetamide	Generator
CAF	HMDB
CAP	HMDB
Chloramfenikol	HMDB
Chloramphenicole	HMDB
Chloroamphenicol	HMDB
Cloroamfenicolo	HMDB
D-Chloramphenicol	HMDB
Detreomycin	HMDB
Kloramfenikol	HMDB
Cloranfenicol	HMDB
Ophthochlor	HMDB
Syntomycin	HMDB
Amphenicols	MeSH
Amphenicol	MeSH

Chemical Formula

C₁₁H₁₂Cl₂N₂O₅

Average Molecular Weight

323.129

Monoisotopic Molecular Weight

322.012326918

IUPAC Name

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

Traditional Name

chloramphenicol

CAS Registry Number

56-75-7

SMILES

OC[C@@H](NC(=O)C(Cl)Cl)[C@H](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)/t8-,9-/m1/s1

InChI Key

WIIZWVCIJKGZOK-RKDXNWHRSA-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
C-nitro compound
Secondary alcohol
Organic nitro compound
Carboximidic acid
Carboximidic acid derivative
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Aromatic alcohol
Organopnictogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organochloride
Alkyl halide
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Organic zwitterion
Alcohol
Alkyl chloride
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:17698 )
Aromatic compounds (C00918 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Organ

Liver (HMDB: HMDB0014589)
Heart (HMDB: HMDB0014589)

Tissue

Connective tissue

Bone marrow (HMDB: HMDB0014589)

Source

Exogenous

Exogenous (HMDB: HMDB0014589)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Chloramphenicol Action Pathway (PathBank: SMP0000729)

Role

Industrial application

Pharmaceutical industry

Antimicrobial agent

Antibiotic (HMDB: HMDB0014589)

Antibacterial drug (HMDB: HMDB0014589)

Protein synthesis inhibitor (HMDB: HMDB0014589)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	150.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.46 g/L	Not Available
LogP	0.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.46 g/L	ALOGPS
logP	1.15	ALOGPS
logP	0.88	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.49	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	115.38 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	73.2 m³·mol⁻¹	ChemAxon
Polarizability	28.08 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]+	164.428	30932474
DeepCCS	[M-H]-	162.07	30932474
DeepCCS	[M-2H]-	194.955	30932474
DeepCCS	[M+Na]+	170.521	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 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.	3.91 minutes	32390414
Predicted by Siyang on May 30, 2022	11.2426 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.4 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	36.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1465.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	284.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	117.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	180.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	59.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	313.6 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	378.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	134.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	828.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	330.0 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	1081.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	272.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	291.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	390.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	288.1 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	123.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chloramphenicol	OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O	3663.6	Standard polar	33892256
Chloramphenicol	OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O	2540.0	Standard non polar	33892256
Chloramphenicol	OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O	2555.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chloramphenicol,1TMS,isomer #1	C[Si](C)(C)OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C([N+](=O)[O-])C=C1	2458.2	Semi standard non polar	33892256
Chloramphenicol,1TMS,isomer #2	C[Si](C)(C)O[C@H](C1=CC=C([N+](=O)[O-])C=C1)[C@@H](CO)NC(=O)C(Cl)Cl	2442.1	Semi standard non polar	33892256
Chloramphenicol,1TMS,isomer #3	C[Si](C)(C)N(C(=O)C(Cl)Cl)[C@H](CO)[C@H](O)C1=CC=C([N+](=O)[O-])C=C1	2480.0	Semi standard non polar	33892256
Chloramphenicol,2TMS,isomer #1	C[Si](C)(C)OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C1	2429.8	Semi standard non polar	33892256
Chloramphenicol,2TMS,isomer #2	C[Si](C)(C)OC[C@H]([C@H](O)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C	2465.8	Semi standard non polar	33892256
Chloramphenicol,2TMS,isomer #3	C[Si](C)(C)O[C@H](C1=CC=C([N+](=O)[O-])C=C1)[C@@H](CO)N(C(=O)C(Cl)Cl)[Si](C)(C)C	2500.3	Semi standard non polar	33892256
Chloramphenicol,3TMS,isomer #1	C[Si](C)(C)OC[C@H]([C@H](O[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C	2528.1	Semi standard non polar	33892256
Chloramphenicol,3TMS,isomer #1	C[Si](C)(C)OC[C@H]([C@H](O[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C	2503.2	Standard non polar	33892256
Chloramphenicol,3TMS,isomer #1	C[Si](C)(C)OC[C@H]([C@H](O[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C	2922.8	Standard polar	33892256
Chloramphenicol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C([N+](=O)[O-])C=C1	2734.8	Semi standard non polar	33892256
Chloramphenicol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H](C1=CC=C([N+](=O)[O-])C=C1)[C@@H](CO)NC(=O)C(Cl)Cl	2724.8	Semi standard non polar	33892256
Chloramphenicol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)C(Cl)Cl)[C@H](CO)[C@H](O)C1=CC=C([N+](=O)[O-])C=C1	2804.7	Semi standard non polar	33892256
Chloramphenicol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C([N+](=O)[O-])C=C1	2983.6	Semi standard non polar	33892256
Chloramphenicol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]([C@H](O)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C(C)(C)C	3040.7	Semi standard non polar	33892256
Chloramphenicol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H](C1=CC=C([N+](=O)[O-])C=C1)[C@@H](CO)N(C(=O)C(Cl)Cl)[Si](C)(C)C(C)(C)C	3056.9	Semi standard non polar	33892256
Chloramphenicol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]([C@H](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	3288.7	Semi standard non polar	33892256
Chloramphenicol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]([C@H](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	3139.3	Standard non polar	33892256
Chloramphenicol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]([C@H](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	3136.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Chloramphenicol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-3900000000-2ba6754ba027027454d1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chloramphenicol GC-MS (2 TMS) - 70eV, Positive	splash10-0udi-3911100000-5438beab478c45792ddb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chloramphenicol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chloramphenicol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-qTof , Positive-QTOF	splash10-014i-0920000000-96bfb1c31d89e3f10caf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QFT , negative-QTOF	splash10-0kmi-0945000000-40a09f3f9528bd669823	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QFT , negative-QTOF	splash10-0udi-0900000000-64dbb16119292f4410e2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QFT , negative-QTOF	splash10-0udi-0900000000-5c8fbcad8e93fa9f2906	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QFT , negative-QTOF	splash10-0uk9-1900000000-4c6518583a7488591aa3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QFT , negative-QTOF	splash10-00di-1900000000-00574ed667d64b4a45e9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QFT , negative-QTOF	splash10-00di-1900000000-d4ac63e9260ab31ac6b1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QTOF , negative-QTOF	splash10-0zml-0933000000-4ae209b29cb52d4e3844	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QTOF , negative-QTOF	splash10-056r-0933000000-74ff5ec451e56526d425	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol Linear Ion Trap , negative-QTOF	splash10-0a4l-0590000000-90d108018a0f99815fb7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol Linear Ion Trap , negative-QTOF	splash10-0a4l-0690000000-161f2afa43298fd3437a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QFT , negative-QTOF	splash10-0uk9-0923000000-86308db0ec59b40b1533	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QFT , positive-QTOF	splash10-05fr-0094000000-ad8da59124745b38a76f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QFT , positive-QTOF	splash10-00di-0390000000-06fcf307f2fdb79741ad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QFT , positive-QTOF	splash10-014i-1940000000-be07d702045f4d3e05ac	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QFT , positive-QTOF	splash10-014i-1910000000-55a74a828c3c9750ee1c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QFT , positive-QTOF	splash10-0159-2900000000-bf685c17ab79583133ee	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QFT , positive-QTOF	splash10-0159-4900000000-e6f6ccbfffe89c345365	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloramphenicol LC-ESI-QTOF , positive-QTOF	splash10-00di-0191000000-41f70006e2b4e5f8d8aa	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloramphenicol 10V, Positive-QTOF	splash10-00di-0109000000-7f19e2214bd804fbb572	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloramphenicol 20V, Positive-QTOF	splash10-014j-0289000000-ea9835706b530fa07197	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloramphenicol 40V, Positive-QTOF	splash10-03di-2910000000-531d8b69053d0c007aeb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloramphenicol 10V, Negative-QTOF	splash10-00di-0109000000-cc647af0a1726c8e11c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloramphenicol 20V, Negative-QTOF	splash10-0229-3915000000-a08bc180ba95289b9297	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloramphenicol 40V, Negative-QTOF	splash10-004i-4900000000-7ccaa4da01cb96a52d23	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Chloramphenicol Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00446	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00446	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00446

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5744

KEGG Compound ID

C00918

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chloramphenicol

METLIN ID

Not Available

PubChem Compound

5959

PDB ID

CLM

ChEBI ID

17698

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)

Download (PDF)

General References

Wali SS, Macfarlane JT, Weir WR, Cleland PG, Ball PA, Hassan-King M, Whittle HC, Greenwood BM: Single injection treatment of meningococcal meningitis. 2. Long-acting chloramphenicol. Trans R Soc Trop Med Hyg. 1979;73(6):698-702. [PubMed:538813 ]
Bhutta ZA, Niazi SK, Suria A: Chloramphenicol clearance in typhoid fever: implications for therapy. Indian J Pediatr. 1992 Mar-Apr;59(2):213-9. [PubMed:1398851 ]
Pecoul B, Varaine F, Keita M, Soga G, Djibo A, Soula G, Abdou A, Etienne J, Rey M: Long-acting chloramphenicol versus intravenous ampicillin for treatment of bacterial meningitis. Lancet. 1991 Oct 5;338(8771):862-6. [PubMed:1681224 ]
Puddicombe JB, Wali SS, Greenwood BM: A field trial of a single intramuscular injection of long-acting chloramphenicol in the treatment of meningococcal meningitis. Trans R Soc Trop Med Hyg. 1984;78(3):399-403. [PubMed:6464136 ]
Nathan N, Borel T, Djibo A, Evans D, Djibo S, Corty JF, Guillerm M, Alberti KP, Pinoges L, Guerin PJ, Legros D: Ceftriaxone as effective as long-acting chloramphenicol in short-course treatment of meningococcal meningitis during epidemics: a randomised non-inferiority study. Lancet. 2005 Jul 23-29;366(9482):308-13. [PubMed:16039333 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

Enzyme Details

5. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

6. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]

Showing metabocard for Chloramphenicol (HMDB0014589)

MOL for HMDB0014589 (Chloramphenicol)

3D MOL for HMDB0014589 (Chloramphenicol)

3D SDF for HMDB0014589 (Chloramphenicol)

3D-SDF for HMDB0014589 (Chloramphenicol)

PDB for HMDB0014589 (Chloramphenicol)

3D PDB for HMDB0014589 (Chloramphenicol)

SMILES for HMDB0014589 (Chloramphenicol)

INCHI for HMDB0014589 (Chloramphenicol)

Structure for HMDB0014589 (Chloramphenicol)

3D Structure for HMDB0014589 (Chloramphenicol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

Transporters

References