BRENDA - Enzyme Database
show all sequences of 1.14.15.29

Substrate analog studies of the omega-regiospecificity of Mycobacterium tuberculosis cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and CYP142A1

Johnston, J.B.; Singh, A.A.; Clary, A.A.; Chen, C.K.; Hayes, P.Y.; Chow, S.; De Voss, J.J.; Ortiz de Montellano, P.R.; Bioorg. Med. Chem. 20, 4064-4081 (2012)

Data extracted from this reference:

Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
cholest-5-en-3-beta-ol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
Mycobacterium tuberculosis
-
(25S)-3beta-hydroxycholest-5-en-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
?
cholest-5-en-3-beta-ol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
Mycobacterium tuberculosis H37Rv
-
(25S)-3beta-hydroxycholest-5-en-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
?
additional information
Mycobacterium tuberculosis
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
?
-
-
-
additional information
Mycobacterium tuberculosis H37Rv
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
?
-
-
-
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Mycobacterium tuberculosis
P9WPP1
-
-
Mycobacterium tuberculosis H37Rv
P9WPP1
-
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(25S)-25-bromo-27-norcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis
(25S)-25-bromo-27-norcholesterol-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
(25S)-25-bromo-27-norcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis H37Rv
(25S)-25-bromo-27-norcholesterol-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
26-methylcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis
(25S)-3beta-hydroxycholest-5-en-27-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
26-methylcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis H37Rv
(25S)-3beta-hydroxycholest-5-en-27-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
cholest-5-en-3-beta-ol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis
(25S)-3beta-hydroxycholest-5-en-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
cholest-5-en-3-beta-ol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis H37Rv
(25S)-3beta-hydroxycholest-5-en-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
additional information
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
744481
Mycobacterium tuberculosis
?
-
-
-
-
additional information
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
744481
Mycobacterium tuberculosis H37Rv
?
-
-
-
-
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.3
-
(25S)-25-bromo-27-norcholesterol
pH 7.5, 25°C
Mycobacterium tuberculosis
0.317
-
26-methylcholesterol
pH 7.5, 25°C
Mycobacterium tuberculosis
0.467
-
cholest-5-en-3-beta-ol
pH 7.5, 25°C
Mycobacterium tuberculosis
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
cholest-5-en-3-beta-ol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
Mycobacterium tuberculosis
-
(25S)-3beta-hydroxycholest-5-en-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
?
cholest-5-en-3-beta-ol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
Mycobacterium tuberculosis H37Rv
-
(25S)-3beta-hydroxycholest-5-en-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
?
additional information
Mycobacterium tuberculosis
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
?
-
-
-
additional information
Mycobacterium tuberculosis H37Rv
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
?
-
-
-
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(25S)-25-bromo-27-norcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis
(25S)-25-bromo-27-norcholesterol-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
(25S)-25-bromo-27-norcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis H37Rv
(25S)-25-bromo-27-norcholesterol-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
26-methylcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis
(25S)-3beta-hydroxycholest-5-en-27-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
26-methylcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis H37Rv
(25S)-3beta-hydroxycholest-5-en-27-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
cholest-5-en-3-beta-ol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis
(25S)-3beta-hydroxycholest-5-en-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
cholest-5-en-3-beta-ol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis H37Rv
(25S)-3beta-hydroxycholest-5-en-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
additional information
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
744481
Mycobacterium tuberculosis
?
-
-
-
-
additional information
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
744481
Mycobacterium tuberculosis H37Rv
?
-
-
-
-
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.3
-
(25S)-25-bromo-27-norcholesterol
pH 7.5, 25°C
Mycobacterium tuberculosis
0.317
-
26-methylcholesterol
pH 7.5, 25°C
Mycobacterium tuberculosis
0.467
-
cholest-5-en-3-beta-ol
pH 7.5, 25°C
Mycobacterium tuberculosis
Other publictions for EC 1.14.15.29
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
744344
Frank
Cytochrome P450 125A4, the th ...
Mycolicibacterium smegmatis, Mycolicibacterium smegmatis ATCC 700084
Biochemistry
54
6909-6916
2015
-
-
1
1
2
-
-
3
-
-
-
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6
-
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-
-
-
-
12
-
-
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-
-
-
-
-
-
-
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-
-
2
-
2
2
-
-
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-
3
-
-
-
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-
-
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-
-
-
-
-
12
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
744481
Johnston
Substrate analog studies of t ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
Bioorg. Med. Chem.
20
4064-4081
2012
-
-
-
-
-
-
-
-
-
-
-
4
-
4
-
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-
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8
-
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-
-
3
-
-
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-
-
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4
-
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-
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8
-
-
-
-
3
-
-
-
-
-
-
-
-
-
-
717344
Ouellet
Reverse type I inhibitor of My ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
Bioorg. Med. Chem. Lett.
21
332-337
2011
-
-
-
1
1
-
1
-
-
-
-
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-
6
-
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-
-
-
-
-
-
2
-
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1
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1
1
1
-
-
1
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-
-
-
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-
-
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-
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2
-
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-
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-
-
-
-
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-
717811
Johnston
Functional redundancy of stero ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis CDC 1551, Mycobacterium tuberculosis H37Rv
J. Biol. Chem.
285
36352-36360
2010
-
-
1
-
-
-
-
2
-
-
-
-
-
165
-
-
1
-
-
-
-
-
6
-
-
-
-
2
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-
-
1
-
-
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-
1
1
-
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-
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-
2
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1
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-
-
6
-
-
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-
2
-
-
-
-
-
-
-
-
-
-
718129
Ouellet
Mycobacterium tuberculosis CYP ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis CDC 1551
Mol. Microbiol.
77
730-742
2010
-
-
1
1
-
-
-
-
-
-
-
2
-
4
-
-
1
-
-
-
-
-
2
-
-
-
-
-
-
-
-
1
-
-
-
-
-
1
1
1
-
-
-
-
-
-
-
-
-
2
-
-
-
1
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
2
2
-
-
-
717241
Ouellet
Reaction of Mycobacterium tube ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
Biochemistry
48
863-872
2009
-
-
1
-
-
-
1
-
-
-
-
-
-
161
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
717782
McLean
The structure of Mycobacterium ...
Mycobacterium tuberculosis
J. Biol. Chem.
284
35524-35533
2009
-
-
1
1
-
-
-
-
-
-
-
-
-
3
-
-
1
-
-
-
-
-
1
-
-
-
-
-
-
-
-
2
-
-
-
-
-
1
2
1
-
-
-
-
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-
-
-
-
-
-
-
-
1
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
717783
Capyk
Mycobacterial cytochrome P450 ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv, Mycobacterium tuberculosis variant bovis, Mycobacterium tuberculosis variant bovis bacillus Calmette-Guerin
J. Biol. Chem.
284
35534-35542
2009
-
-
2
-
-
-
-
1
-
-
2
-
-
168
-
-
2
-
-
-
-
-
8
-
-
-
2
-
-
-
-
2
-
-
-
-
-
2
2
-
-
-
-
-
-
1
-
-
2
-
-
-
-
2
-
-
-
-
8
-
-
-
2
-
-
-
-
-
1
2
2
1
1
1
718126
Rosloniec
Cytochrome P450 125 (CYP125) c ...
Rhodococcus jostii
Mol. Microbiol.
74
1031-1043
2009
-
-
1
-
-
-
-
-
-
-
1
-
-
5
-
-
1
-
-
-
-
-
-
1
-
-
-
-
-
-
-
2
-
-
-
-
-
1
2
-
-
-
-
-
-
-
-
-
1
-
-
-
-
1
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
2
2
-
-
-