BRENDA - Enzyme Database

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)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
1.14.15.29
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
-
-
?
1.14.15.29
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
-
-
?
1.14.15.29
additional information
Mycobacterium tuberculosis
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
?
-
-
-
1.14.15.29
additional information
Mycobacterium tuberculosis H37Rv
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
?
-
-
-
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
1.14.15.28
Mycobacterium tuberculosis
P9WPL5
-
-
1.14.15.28
Mycobacterium tuberculosis H37Rv
P9WPL5
-
-
1.14.15.29
Mycobacterium tuberculosis
P9WPP1
-
-
1.14.15.29
Mycobacterium tuberculosis H37Rv
P9WPP1
-
-
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1.14.15.28
(25R)-25-bromo-27-norcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis
(25R)-25-bromo-27-norcholesterol-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
(25R)-25-bromo-27-norcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis H37Rv
(25R)-25-bromo-27-norcholesterol-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
26-methylcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis
(25R)-3beta-hydroxycholest-5-en-27-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
26-methylcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis H37Rv
(25R)-3beta-hydroxycholest-5-en-27-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
cholest-5-en-3-beta-ol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis
(25R)-3beta-hydroxycholest-5-en-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
cholest-5-en-3-beta-ol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis H37Rv
(25R)-3beta-hydroxycholest-5-en-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
lanosterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis
lanosterol-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
lanosterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis H37Rv
lanosterol-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
additional information
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
744481
Mycobacterium tuberculosis
?
-
-
-
-
1.14.15.28
additional information
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
744481
Mycobacterium tuberculosis H37Rv
?
-
-
-
-
1.14.15.29
(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
-
-
-
?
1.14.15.29
(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
-
-
-
?
1.14.15.29
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
-
-
-
?
1.14.15.29
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
-
-
-
?
1.14.15.29
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
-
-
-
?
1.14.15.29
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
-
-
-
?
1.14.15.29
additional information
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
744481
Mycobacterium tuberculosis
?
-
-
-
-
1.14.15.29
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]
EC Number
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
1.14.15.28
0.163
-
26-methylcholesterol
pH 7.5, 25°C
Mycobacterium tuberculosis
1.14.15.28
0.278
-
cholest-5-en-3-beta-ol
pH 7.5, 25°C
Mycobacterium tuberculosis
1.14.15.28
0.299
-
(25R)-25-bromo-27-norcholesterol
pH 7.5, 25°C
Mycobacterium tuberculosis
1.14.15.28
0.368
-
(25R)-25-bromo-27-norcholesterol
pH 7.5, 25°C
Mycobacterium tuberculosis
1.14.15.29
0.3
-
(25S)-25-bromo-27-norcholesterol
pH 7.5, 25°C
Mycobacterium tuberculosis
1.14.15.29
0.317
-
26-methylcholesterol
pH 7.5, 25°C
Mycobacterium tuberculosis
1.14.15.29
0.467
-
cholest-5-en-3-beta-ol
pH 7.5, 25°C
Mycobacterium tuberculosis
Natural Substrates/ Products (Substrates) (protein specific)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
1.14.15.29
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
-
-
?
1.14.15.29
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
-
-
?
1.14.15.29
additional information
Mycobacterium tuberculosis
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
?
-
-
-
1.14.15.29
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)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1.14.15.28
(25R)-25-bromo-27-norcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis
(25R)-25-bromo-27-norcholesterol-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
(25R)-25-bromo-27-norcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis H37Rv
(25R)-25-bromo-27-norcholesterol-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
26-methylcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis
(25R)-3beta-hydroxycholest-5-en-27-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
26-methylcholesterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis H37Rv
(25R)-3beta-hydroxycholest-5-en-27-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
cholest-5-en-3-beta-ol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis
(25R)-3beta-hydroxycholest-5-en-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
cholest-5-en-3-beta-ol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis H37Rv
(25R)-3beta-hydroxycholest-5-en-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
lanosterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis
lanosterol-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
lanosterol + 6 reduced [2Fe-2S] ferredoxin + 3 O2
-
744481
Mycobacterium tuberculosis H37Rv
lanosterol-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
-
-
-
?
1.14.15.28
additional information
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
744481
Mycobacterium tuberculosis
?
-
-
-
-
1.14.15.28
additional information
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
744481
Mycobacterium tuberculosis H37Rv
?
-
-
-
-
1.14.15.29
(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
-
-
-
?
1.14.15.29
(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
-
-
-
?
1.14.15.29
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
-
-
-
?
1.14.15.29
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
-
-
-
?
1.14.15.29
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
-
-
-
?
1.14.15.29
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
-
-
-
?
1.14.15.29
additional information
no substrates: 25-thia-27-norcholesterol, 24-bromochol-5-enol, 26-methylcholesta-5,25(26)-dienol
744481
Mycobacterium tuberculosis
?
-
-
-
-
1.14.15.29
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)
EC Number
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
1.14.15.28
0.163
-
26-methylcholesterol
pH 7.5, 25°C
Mycobacterium tuberculosis
1.14.15.28
0.278
-
cholest-5-en-3-beta-ol
pH 7.5, 25°C
Mycobacterium tuberculosis
1.14.15.28
0.299
-
(25R)-25-bromo-27-norcholesterol
pH 7.5, 25°C
Mycobacterium tuberculosis
1.14.15.28
0.368
-
(25R)-25-bromo-27-norcholesterol
pH 7.5, 25°C
Mycobacterium tuberculosis
1.14.15.29
0.3
-
(25S)-25-bromo-27-norcholesterol
pH 7.5, 25°C
Mycobacterium tuberculosis
1.14.15.29
0.317
-
26-methylcholesterol
pH 7.5, 25°C
Mycobacterium tuberculosis
1.14.15.29
0.467
-
cholest-5-en-3-beta-ol
pH 7.5, 25°C
Mycobacterium tuberculosis