MiMeDB: Showing metabocard for chloramphenicol 3-acetic acid (MMDBc0055796)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:06:45 UTC

Update Date

2022-08-12 20:09:28 UTC

Metabolite ID

MMDBc0055796

Metabolite Identification

Common Name

chloramphenicol 3-acetic acid

Description

Chloramphenicol 3-acetate, also known as 3'-O-acetylchloramphenicol, 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. Based on a literature review very few articles have been published on Chloramphenicol 3-acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222062D          

 25 25  0  0  1  0            999 V2000
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    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
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 O   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
   -0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  1  1  0  0  0  0
  8  2  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 12  1  0  0  0  0
 15 12  1  0  0  0  0
 10 16  1  6  0  0  0
 16 13  2  0  0  0  0
 17  9  1  0  0  0  0
 18  7  2  0  0  0  0
 11 19  1  6  0  0  0
 13 20  1  4  0  0  0
 21 17  2  0  0  0  0
 22 17  2  0  0  0  0
 23  6  1  0  0  0  0
 23  7  1  0  0  0  0
 10 24  1  6  0  0  0
 11 25  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0055796

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](O)(C1=CC=C(C=C1)N(=O)=O)[C@@]([H])(COC(C)=O)N=C(O)C(Cl)Cl

> <INCHI_IDENTIFIER>
InChI=1S/C13H14Cl2N2O6/c1-7(18)23-6-10(16-13(20)12(14)15)11(19)8-2-4-9(5-3-8)17(21)22/h2-5,10-12,19H,6H2,1H3,(H,16,20)/t10-,11-/m1/s1

> <INCHI_KEY>
VVOIFRARHIZCJD-GHMZBOCLSA-N

> <FORMULA>
C13H14Cl2N2O6

> <MOLECULAR_WEIGHT>
365.16

> <EXACT_MASS>
364.0228916

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
32.3163107598963

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(1R,2R)-3-(acetyloxy)-1-hydroxy-1-(4-nitrophenyl)propan-2-yl]-2,2-dichloroethanimidic acid

> <JCHEM_LOGP>
2.139433025333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.635400911195092

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.093014253646462

> <JCHEM_PKA_STRONGEST_BASIC>
0.025048145904665642

> <JCHEM_POLAR_SURFACE_AREA>
124.94000000000001

> <JCHEM_REFRACTIVITY>
82.87389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1R,2R)-3-(acetyloxy)-1-hydroxy-1-(4-nitrophenyl)propan-2-yl]-2,2-dichloroethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       2.667  -3.080   0.000  0.00  0.00          Cl+0
HETATM   15 Cl   UNK     0       0.000  -3.080   0.000  0.00  0.00          Cl+0
HETATM   16  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      -6.668  -0.770   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0      -0.000   3.080   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2    4    8                                                       
CONECT    3    5    8                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6   10   23                                                       
CONECT    7    1   18   23                                                  
CONECT    8    2    3   11                                                  
CONECT    9    4    5   17                                                  
CONECT   10    6   11   16   24                                             
CONECT   11    8   10   19   25                                             
CONECT   12   13   14   15                                                  
CONECT   13   12   16   20                                                  
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   10   13                                                       
CONECT   17    9   21   22                                                  
CONECT   18    7                                                            
CONECT   19   11                                                            
CONECT   20   13                                                            
CONECT   21   17                                                            
CONECT   22   17                                                            
CONECT   23    6    7                                                       
CONECT   24   10                                                            
CONECT   25   11                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

Synonyms

Value	Source
Chloramphenicol 3-acetic acid	Generator
3'-O-Acetylchloramphenicol	MeSH
3-Acetylchloramphenicol	MeSH

Molecular Formula

C₁₃H₁₄Cl₂N₂O₆

Average Mass

365.16

Monoisotopic Mass

364.0228916

IUPAC Name

N-[(1R,2R)-3-(acetyloxy)-1-hydroxy-1-(4-nitrophenyl)propan-2-yl]-2,2-dichloroethanimidic acid

Traditional Name

N-[(1R,2R)-3-(acetyloxy)-1-hydroxy-1-(4-nitrophenyl)propan-2-yl]-2,2-dichloroethanimidic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(C1=CC=C(C=C1)N(=O)=O)[C@@]([H])(COC(C)=O)N=C(O)C(Cl)Cl

InChI Identifier

InChI=1S/C13H14Cl2N2O6/c1-7(18)23-6-10(16-13(20)12(14)15)11(19)8-2-4-9(5-3-8)17(21)22/h2-5,10-12,19H,6H2,1H3,(H,16,20)/t10-,11-/m1/s1

InChI Key

VVOIFRARHIZCJD-GHMZBOCLSA-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
Carboxylic acid ester
C-nitro compound
Secondary alcohol
Organic nitro compound
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organonitrogen compound
Organochloride
Carbonyl group
Organohalogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organic oxide
Aromatic alcohol
Organic zwitterion
Alcohol
Alkyl chloride
Alkyl halide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

acetate ester (CHEBI:16730 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	2.14	ChemAxon
pKa (Strongest Acidic)	2.09	ChemAxon
pKa (Strongest Basic)	0.025	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	124.94 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	82.87 m³·mol⁻¹	ChemAxon
Polarizability	32.32 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

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0013766	Acetyl-CoA	chloramphenicol 3-acetic acid	Chloramphenicol acetyltransferase	N-Acetylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Proteobacteria	13	Human ; Human subgingival plaque; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum
Bacteria	Firmicutes	7	Human feces; Goat feces; Sheep feces; Human ; Human subgingival plaque; Human saliva
Bacteria	Actinobacteria	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

75742

KEGG Compound ID

C03601

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

83940

PDB ID

Not Available

ChEBI ID

16730

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for chloramphenicol 3-acetic acid (MMDBc0055796)

MOL for #<Metabolite:0x00007fe2bc0bbf48>

3D MOL for #<Metabolite:0x00007fe2bc0bbf48>

3D SDF for #<Metabolite:0x00007fe2bc0bbf48>

3D-SDF for #<Metabolite:0x00007fe2bc0bbf48>

PDB for #<Metabolite:0x00007fe2bc0bbf48>

3D PDB for #<Metabolite:0x00007fe2bc0bbf48>

SMILES for #<Metabolite:0x00007fe2bc0bbf48>

INCHI for #<Metabolite:0x00007fe2bc0bbf48>

Structure for #<Metabolite:0x00007fe2bc0bbf48>

3D Structure for #<Metabolite:0x00007fe2bc0bbf48>