KEGG   ORTHOLOGY: K16046
Entry
K16046                      KO                                     

Name
CYP142
Definition
cholest-4-en-3-one 26-monooxygenase [EC:1.14.15.28]
Pathway
ko00984  Steroid degradation
ko01120  Microbial metabolism in diverse environments
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09111 Xenobiotics biodegradation and metabolism
   00984 Steroid degradation
    K16046  CYP142; cholest-4-en-3-one 26-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K16046  CYP142; cholest-4-en-3-one 26-monooxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.15  With reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.15.28  cholest-4-en-3-one 26-monooxygenase [(25R)-3-oxocholest-4-en-26-oate forming]
     K16046  CYP142; cholest-4-en-3-one 26-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, bacteria type
  CYP142 family
   K16046  CYP142; cholest-4-en-3-one 26-monooxygenase
Other DBs
RN: R11358 R11359 R11360 R11361
COG: COG2124
Genes
OSG: BST96_12435
MAGA: Mag101_11190
HALC: EY643_16850
MDH: AYM39_17655
MKO: MKLM6_3584
NTT: TAO_0192
SPHQ: BWQ93_03535
SPHD: HY78_21990
SPMI: K663_17301 K663_18056
ELQ: Ga0102493_111086
MTU: Rv3518c(cyp142)
MTC: MT3619
MRA: MRA_3557(cyp142)
MTUR: CFBS_3734(cyp142)
MTO: MTCTRI2_3582(cyp142)
MTD: UDA_3518c(cyp142)
MTN: ERDMAN_3857(cyp142)
MTUC: J113_24605
MTUE: J114_18810
MTUH: I917_24680
MTUL: TBHG_03458
MTUT: HKBT1_3719(cyp142)
MTUU: HKBT2_3728(cyp142)
MTQ: HKBS1_3731(cyp142)
MBO: BQ2027_MB3547C(cyp142b) BQ2027_MB3548C(cyp142a)
MBB: BCG_3581c(cyp142b) BCG_3582c(cyp142a)
MBT: JTY_3582(cyp142b) JTY_3583(cyp142a)
MBM: BCGMEX_3579c(cyp142b) BCGMEX_3580c(cyp142a)
MBX: BCGT_3381
MCE: MCAN_35291(cyp142)
MCQ: BN44_110006(cyp)
MCV: BN43_90011(cyp)
MCX: BN42_90009(cyp)
MCZ: BN45_100009(cyp)
MPA: MAP_0547
MAO: MAP4_3320
MAVI: RC58_16465
MAVU: RE97_16500
MAV: MAV_0641
MLP: MLM_0784
MUL: MUL_4077(cyp142A3)
MMC: Mmcs_4631
MKM: Mkms_4719
MJL: Mjls_5013
MMI: MMAR_5003(cyp142A3)
MMAE: MMARE11_48130(cyp142A3)
MLI: MULP_05251(cyp142A3)
MHAD: B586_04705
MSHG: MSG_03800 MSG_04505(cyp142)
MSG: MSMEI_5758(cyp142)
MVA: Mvan_5217
MGI: Mflv_1541
MVQ: MYVA_5103
MHAS: MHAS_03703
MJD: JDM601_3652(cyp142A3)
MTER: 4434518_03626(cyp142A3)
MKR: MKOR_35990(cyp142)
RER: RER_07670
REY: O5Y_03730
ROP: ROP_45330
REQ: REQ_06880
TCU: Tcur_2583
SRO: Sros_7155
PDX: Psed_6445
 » show all
Reference
  Authors
Johnston JB, Ouellet H, Ortiz de Montellano PR
  Title
Functional redundancy of steroid C26-monooxygenase activity in Mycobacterium tuberculosis revealed by biochemical and genetic analyses.
  Journal
J Biol Chem 285:36352-60 (2010)
DOI:10.1074/jbc.M110.161117
  Sequence
[mtu:Rv3518c]
Reference
  Authors
Ouellet H, Johnston JB, de Montellano PR
  Title
Cholesterol catabolism as a therapeutic target in Mycobacterium tuberculosis.
  Journal
Trends Microbiol 19:530-9 (2011)
DOI:10.1016/j.tim.2011.07.009
  Sequence
[mtu:Rv3518c]

KEGG   ENZYME: 1.14.15.28
Entry
EC 1.14.15.28               Enzyme                                 

Name
cholest-4-en-3-one 26-monooxygenase [(25R)-3-oxocholest-4-en-26-oate forming];
CYP142
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
cholest-4-en-3-one,reduced [2Fe-2S] ferredoxin:oxygen oxidoreductase [(25R)-3-oxocholest-4-en-26-oate forming]
Reaction(IUBMB)
cholest-4-en-3-one + 6 reduced [2Fe-2S] ferredoxin + 3 O2 = (25R)-3-oxocholest-4-en-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O (overall reaction) [RN:R11361];
(1a) cholest-4-en-3-one + 2 reduced [2Fe-2S] ferredoxin + O2 = (25R)-26-hydroxycholest-4-en-3-one + 2 oxidized [2Fe-2S] ferredoxin + H2O [RN:R11358];
(1b) (25R)-26-hydroxycholest-4-en-3-one + 2 reduced [2Fe-2S] ferredoxin + O2 = (25R)-26-oxocholest-4-en-3-one + 2 oxidized [2Fe-2S] ferredoxin + 2 H2O [RN:R11359];
(1c) (25R)-26-oxocholest-4-en-3-one + 2 reduced [2Fe-2S] ferredoxin + O2 = (25R)-3-oxocholest-4-en-26-oate + 2 oxidized [2Fe-2S] ferredoxin + H2O [RN:R11360]
Reaction(KEGG)
Substrate
cholest-4-en-3-one [CPD:C00599];
reduced [2Fe-2S] ferredoxin [CPD:C22150];
O2 [CPD:C00007];
(25R)-26-hydroxycholest-4-en-3-one [CPD:C21303];
(25R)-26-oxocholest-4-en-3-one [CPD:C21305]
Product
(25R)-3-oxocholest-4-en-26-oate [CPD:C20839];
oxidized [2Fe-2S] ferredoxin [CPD:C22151];
H2O [CPD:C00001];
(25R)-26-hydroxycholest-4-en-3-one [CPD:C21303];
(25R)-26-oxocholest-4-en-3-one [CPD:C21305]
Comment
This cytochrome P-450 (heme-thiolate) enzyme, found in several bacterial pathogens, is involved in degradation of the host cholesterol. It catalyses the hydroxylation of the C-26 carbon, followed by oxidation of the alcohol to the carboxylic acid via the aldehyde intermediate, initiating the degradation of the alkyl side-chain of cholesterol. The products are exclusively in the (25R) conformation. The enzyme also accepts cholesterol as a substrate. cf. EC 1.14.15.29, cholest-4-en-3-one 26-monooxygenase [(25S)-3-oxocholest-4-en-26-oate forming]. The enzyme can receive electrons from ferredoxin reductase in vitro, its natural electron donor is not known yet.
History
EC 1.14.15.28 created 2016 as EC 1.14.13.221, transferred 2018 to EC 1.14.15.28
Pathway
ec00984  Steroid degradation
ec01120  Microbial metabolism in diverse environments
Orthology
K16046  cholest-4-en-3-one 26-monooxygenase
Genes
OSG: BST96_12435
MAGA: Mag101_11190
HALC: EY643_16850
MDH: AYM39_17655
MKO: MKLM6_3584
NTT: TAO_0192
SPHQ: BWQ93_03535
SPHD: HY78_21990
SPMI: K663_17301 K663_18056
ELQ: Ga0102493_111086
MTU: Rv3518c(cyp142)
MTC: MT3619
MRA: MRA_3557(cyp142)
MTUR: CFBS_3734(cyp142)
MTO: MTCTRI2_3582(cyp142)
MTD: UDA_3518c(cyp142)
MTN: ERDMAN_3857(cyp142)
MTUC: J113_24605
MTUE: J114_18810
MTUH: I917_24680
MTUL: TBHG_03458
MTUT: HKBT1_3719(cyp142)
MTUU: HKBT2_3728(cyp142)
MTQ: HKBS1_3731(cyp142)
MBO: BQ2027_MB3547C(cyp142b) BQ2027_MB3548C(cyp142a)
MBB: BCG_3581c(cyp142b) BCG_3582c(cyp142a)
MBT: JTY_3582(cyp142b) JTY_3583(cyp142a)
MBM: BCGMEX_3579c(cyp142b) BCGMEX_3580c(cyp142a)
MBX: BCGT_3381
MCE: MCAN_35291(cyp142)
MCQ: BN44_110006(cyp)
MCV: BN43_90011(cyp)
MCX: BN42_90009(cyp)
MCZ: BN45_100009(cyp)
MPA: MAP_0547
MAO: MAP4_3320
MAVI: RC58_16465
MAVU: RE97_16500
MAV: MAV_0641
MLP: MLM_0784
MUL: MUL_4077(cyp142A3)
MMC: Mmcs_4631
MKM: Mkms_4719
MJL: Mjls_5013
MMI: MMAR_5003(cyp142A3)
MMAE: MMARE11_48130(cyp142A3)
MLI: MULP_05251(cyp142A3)
MHAD: B586_04705
MSHG: MSG_03800 MSG_04505(cyp142)
MSG: MSMEI_5758(cyp142)
MVA: Mvan_5217
MGI: Mflv_1541
MVQ: MYVA_5103
MHAS: MHAS_03703
MJD: JDM601_3652(cyp142A3)
MTER: 4434518_03626(cyp142A3)
MKR: MKOR_35990(cyp142)
RER: RER_07670
REY: O5Y_03730
ROP: ROP_45330
REQ: REQ_06880
TCU: Tcur_2583
SRO: Sros_7155
PDX: Psed_6445
 » show all
Reference
1  [PMID:20889498]
  Authors
Driscoll MD, McLean KJ, Levy C, Mast N, Pikuleva IA, Lafite P, Rigby SE, Leys D, Munro AW
  Title
Structural and biochemical characterization of Mycobacterium tuberculosis CYP142: evidence for multiple cholesterol 27-hydroxylase activities in a human pathogen.
  Journal
J Biol Chem 285:38270-82 (2010)
DOI:10.1074/jbc.M110.164293
  Sequence
[mtu:Rv3518c]
Reference
2  [PMID:20843794]
  Authors
Johnston JB, Ouellet H, Ortiz de Montellano PR
  Title
Functional redundancy of steroid C26-monooxygenase activity in Mycobacterium tuberculosis revealed by biochemical and genetic analyses.
  Journal
J Biol Chem 285:36352-60 (2010)
DOI:10.1074/jbc.M110.161117
  Sequence
[mtu:Rv3518c]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.15.28
IUBMB Enzyme Nomenclature: 1.14.15.28
ExPASy - ENZYME nomenclature database: 1.14.15.28
BRENDA, the Enzyme Database: 1.14.15.28

KEGG   REACTION: R11361
Entry
R11361                      Reaction                               

Name
cholest-4-en-3-one,reduced-2Fe-2S]-ferredoxin:oxygen oxidoreductase [(25R)-3-oxocholest-4-en-26-oate forming]
Definition
Cholest-4-en-3-one + 6 Reduced [2Fe-2S] ferredoxin + 3 Oxygen <=> (25R)-3-Oxocholest-4-en-26-oate + 6 Oxidized [2Fe-2S] ferredoxin + 4 H2O
Equation
C00599 + 6 C22150 + 3 C00007 <=> C20839 + 6 C22151 + 4 C00001
Comment
three-step reaction (see R11358+R11359+R11360)
Reaction class
RC03368  C00599_C20839
Enzyme
Pathway
rn00984  Steroid degradation
rn01120  Microbial metabolism in diverse environments
Orthology
K16046  cholest-4-en-3-one 26-monooxygenase [EC:1.14.15.28]
Other DBs
RHEA: 49999

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