Ligand cocaine

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Basic Ligand Information

Molecular Structure
Picture of cocaine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C17H21NO4
cocaine
ZPUCINDJVBIVPJ-UHFFFAOYSA-N
Synonyms:
(+/-)-cocaine
Pathway Source
Pathways
KEGG
Biosynthesis of alkaloids derived from ornithine, lysine and nicotinic acid, Biosynthesis of secondary metabolites, Tropane, piperidine and pyridine alkaloid biosynthesis
MetaCyc
cocaine biosynthesis

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

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EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
cocaine + H2O = O-benzoylecgonine + methanol
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show the reaction diagram
cocaine + ethanol = cocaethylene + methanol
-
show the reaction diagram
cocaine + H2O = ecgonine methyl ester + benzoate
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show the reaction diagram
cocaine + H2O = ecgonine methyl ester + benzoate
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Substrate in Enzyme-catalyzed Reactions (9 results)

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EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
cocaine = ?
-
show the reaction diagram
cocaine + ethanol = cocaethylene + methanol
-
show the reaction diagram
cocaine + H2O = ecgonine methyl ester + benzoate
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Activator in Enzyme-catalyzed Reactions (1 result)

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COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
cocaine treatment causes an increase in the ventral striatum in enzyme specific activity and enzyme relative mRNA amount determined by real time RT-PCR
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Inhibitor in Enzyme-catalyzed Reactions (1 result)

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COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
10 mM, below 10% residual activity
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (33 results)

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COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
wild-type BChE
418.3
-
A328W/Y332A mutant BChE
386.8
-
wild type enzyme, pH not specified in the publication, 37°C
51.4
-
wild type enzyme, at pH 7.4 and 37°C
pH 7.4, wild-type enzyme
7.8
-
pH 7.4, mutant enzyme W166A
0.27
-
pH 7.4, mutant enzyme W151A
0.1
-
pH 7.4, mutant enzyme S117C
0.046
-
pH 7.4, mutant enzyme Q55E
0.55
-
pH 7.4, mutant enzyme Q55A
1.7
-
pH 7.4, mutant enzyme L407A
0.067
-
pH 7.4, mutant enzyme F408A
0.057
-
pH 7.4, mutant enzyme F261A
0.27
-
pH 7.4, 37°C, wild-type enzyme
2323
-
ph 7.4, 37°C, mutant enzyme T172R/G173Q
2247
-
ph 7.4, 37°C, mutant enzyme G173Q
2384
-
ph 7.4, 37°C, mutant enzyme T172R
2502
-
pegylated mutant enzyme T172R/G173Q, pH not specified in the publication, 37°C
40.1
-
mutant enzyme YGRKKRRQRRR-T172R/G173Q, at pH 7.4 and 37°C
32.62
-
mutant enzyme T172R/G173Q/L196C/I301C, at 37°C, pH not specified in the publication
57.7
-
mutant enzyme T172R/G173Q/G4C/S10C, at 37°C, pH not specified in the publication
39
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mutant enzyme T172R/G173Q, pH not specified in the publication, 37°C
56.6
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mutant enzyme T172R/G173Q, at 37°C, pH not specified in the publication
43.3
-
mutant enzyme T172R/G173Q -YGRKKRRQRRR, at pH 7.4 and 37°C
31.45
-
mutant enzyme T172R/G173Q -LMWP, at pH 7.4 and 37°C
35.17
-
mutant enzyme T172R/G13Q, at pH 7.4 and 37°C
53.4
-
mutant enzyme T172R, at pH 7.4 and 37°C
50.9
-
mutant enzyme LMWP-T172R/G173Q, at pH 7.4 and 37°C
34.42
-
mutant enzyme LMWP-S-S-T172R/G173Q, at pH 7.4 and 37°C
39.17
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mutant enzyme L169K, at pH 7.4 and 37°C
80.1
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mutant enzyme G4C/S10C, pH not specified in the publication, 37°C
49.9
-
mutant enzyme G173Q, at pH 7.4 and 37°C
36.1
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KM Value (40 results)

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COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
wild-type BChE
0.434
-
A328W/Y332A mutant BChE
0.042
-
pH 7.4, mutant enzyme S117C
0.046
-
ph 7.4, 37°C, mutant enzyme G173Q
0.015
-
ph 7.4, 37°C, mutant enzyme T172R
0.024
-
ph 7.4, 37°C, mutant enzyme T172R/G173Q
0.024
-
pH 7.4, 37°C, wild-type enzyme
0.021
-
pH 7.4, mutant enzyme F261A
0.0096
-
pH 7.4, mutant enzyme F408A
0.0051
-
pH 7.4, mutant enzyme L407A
0.0012
-
pH 7.4, mutant enzyme Q55A
0.00075
-
pH 7.4, mutant enzyme Q55E
0.00027
-
wild type enzyme, without preincubation, at pH 7.4 and 37°C
0.0072
-
pH 7.4, mutant enzyme W151A
0.051
-
pH 7.4, mutant enzyme W166A
0.0036
-
pH 7.4, wild-type enzyme
0.00064
-
pH 7.5, 30°C
1.33
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wild type enzyme, after 24 h preincubation at 37°C, at pH 7.4 and 37°C
0.0073
-
wild type enzyme, at pH 7.4 and 37°C
wild type enzyme, pH not specified in the publication, 37°C
0.0057
-
mutant enzyme T172R/G173Q -LMWP, at pH 7.4 and 37°C
0.0415
-
mutant enzyme G173Q, at pH 7.4 and 37°C
0.0037
-
mutant enzyme G4C/S10C, pH not specified in the publication, 37°C
0.021
-
mutant enzyme L169K, at pH 7.4 and 37°C
0.044
-
mutant enzyme L169K/G173Q, after 24 h preincubation at 37°C, at pH 7.4 and 37°C
0.0229
-
mutant enzyme L169K/G173Q, without preincubation, at pH 7.4 and 37°C
0.0303
-
mutant enzyme LMWP-S-S-T172R/G173Q, at pH 7.4 and 37°C
0.0305
-
mutant enzyme LMWP-T172R/G173Q, at pH 7.4 and 37°C
0.049
-
mutant enzyme T172R, at pH 7.4 and 37°C
0.017
-
mutant enzyme T172R/G13Q, at pH 7.4 and 37°C
0.017
-
pH 7.4, 37°C
0.39
-
mutant enzyme T172R/G173Q -YGRKKRRQRRR, at pH 7.4 and 37°C
0.0306
-
mutant enzyme T172R/G173Q, at 37°C, pH not specified in the publication
0.0029
-
mutant enzyme T172R/G173Q, pH not specified in the publication, 37°C
0.026
-
mutant enzyme T172R/G173Q/G4C/S10C, at 37°C, pH not specified in the publication
0.0021
-
mutant enzyme T172R/G173Q/L196C/I301C, at 37°C, pH not specified in the publication
0.0015
-
mutant enzyme YGRKKRRQRRR-T172R/G173Q, at pH 7.4 and 37°C
0.0396
-
pegylated mutant enzyme T172R/G173Q, pH not specified in the publication, 37°C
0.019
-
pH 7.0, 30°C
0.36
-

References & Links

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Links to other databases for cocaine

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ChEBI
PubChem
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PubChem