Any feedback?
Please rate this page
(ligand.php)
(0/150)

BRENDA support

Ligand chloramphenicol

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.

Basic Ligand Information

Molecular Structure
Picture of chloramphenicol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
Molfile
C11H12ClN2O5
chloramphenicol
WIIZWVCIJKGZOK-RKDXNWHRSA-N
Synonyms:
2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide, CAP, chloramphenicol[side 1], chloramphenicol[side 2]

Related pathways

Pathway Source
Pathways
MetaCyc
chloramphenicol biosynthesis

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(1R,2R)-(-)-2-(N-dichloroacetyl)-amino-1-(4-aminophenyl)-1,3-propanediol + reduced phenazine methosulfate + 2 O2 = chloramphenicol + phenazine methosulfate + 2 H2O
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UDP-alpha-D-glucuronate + chloramphenicol = UDP + chloramphenicol beta-D-glucuronide
show the reaction diagram
-
3'-phosphoadenylylsulfate + chloramphenicol = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ATP + H2O + chloramphenicol-[dipeptide-binding protein][side 1] = ADP + phosphate + chloramphenicol[side 2] + [dipeptide-binding protein][side 1]
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
24% activation at 0.1 mM in 1 min
-
stimulates phospholipase B activity
-
for full activation of the AC in vivo RAS2-GTP, CAP and Gpa2 modulate the enzyme synergistically
-

Inhibitor in Enzyme-catalyzed Reactions (27 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
in vitro inhibition
-
rate of NO2- production by 1,7-octadiyne-untreated cells is about 30% lower in the presence of chloramphenicol
-
2.0fold reduced activity in chloramphenicol-treated cells
-
competitive inhibition
-
inhibits the formation of enzyme in cells cotransfected with bacteriophage and chloramphenicol
-
inhibits the synthesis of the enzyme
-
synthesis of the enzyme is repressed
-
50% inhibition at 0.0309 mg/ml; inhibits the extracellular and the hepatoma cell enzyme, IC50, overview
-
10.5fold reduced activity in chloramphenicol-treated cells
-

3D Structure of Enzyme-Ligand-Complex (PDB) (70 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (4 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE

KM Value (36 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE

Ki Value (5 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
3.85
-
at 25°C, pH 8.0
1.85
-
pH 7.0, temperature not specified in the publication
1.85
-
pH 7, temperature not specified in the publication

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
2.36
-
at 25°C, pH 8.0
0.0071
-
pH 7.5, 37°C

References & Links

Links to other databases for chloramphenicol

EXTERNAL LINKS