Entry
Name
cholest-4-en-3-one 26-monooxygenase [(25S)-3-oxocholest-4-en-26-oate forming];
CYP125;
CYP125A1;
cholest-4-en-3-one 27-monooxygenase (misleading);
cholest-4-en-3-one,NADH:oxygen oxidoreductase (26-hydroxylating);
cholest-4-en-3-one 26-monooxygenase (ambiguous)
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
BRITE hierarchy
Sysname
cholest-4-en-3-one,[reduced ferredoxin]:oxygen oxidoreductase [(25S)-3-oxocholest-4-en-26-oate-forming]
Reaction(IUBMB)
cholest-4-en-3-one + 6 reduced ferredoxin [iron-sulfur] cluster + 6 H+ + 3 O2 = (25S)-3-oxocholest-4-en-26-oate + 6 oxidized ferredoxin [iron-sulfur] cluster + 4 H2O (overall reaction) [RN:
R11357 ];
(1a) cholest-4-en-3-one + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = (25S)-26-hydroxycholest-4-en-3-one + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O [RN:
R09859 ];
(1b) (25S)-26-hydroxycholest-4-en-3-one + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = (25S)-26-oxocholest-4-en-3-one + 2 oxidized ferredoxin [iron-sulfur] cluster + 2 H2O [RN:
R11355 ];
(1c) (25S)-26-oxocholest-4-en-3-one + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = (25S)-3-oxocholest-4-en-26-oate + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O [RN:
R11356 ]
Reaction(KEGG)
Substrate
cholest-4-en-3-one [CPD:
C00599 ];
reduced ferredoxin [iron-sulfur] cluster [CPD:
C00138 ];
H+ [CPD:
C00080 ];
O2 [CPD:
C00007 ];
(25S)-26-hydroxycholest-4-en-3-one [CPD:
C20143 ];
(25S)-26-oxocholest-4-en-3-one [CPD:
C21304 ]
Product
(25S)-3-oxocholest-4-en-26-oate [CPD:
C21076 ];
oxidized ferredoxin [iron-sulfur] cluster [CPD:
C00139 ];
H2O [CPD:
C00001 ];
(25S)-26-hydroxycholest-4-en-3-one [CPD:
C20143 ];
(25S)-26-oxocholest-4-en-3-one [CPD:
C21304 ]
Comment
A cytochrome P-450 (heme-thiolate) protein found in several bacterial pathogens. The enzyme is involved in degradation of the host's 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 [4]. The products are exclusively in the (25S) configuration. The enzyme is part of a two-component system that also includes a ferredoxin reductase (most likely KshB, which also interacts with EC
1.14.15.30 , 3-ketosteroid 9alpha-monooxygenase). The enzyme also accepts cholesterol as a substrate. cf. EC
1.14.15.28 , cholest-4-en-3-one 27-monooxygenase.
History
EC 1.14.15.29 created 2012 as EC 1.14.13.141, modified 2016, transferred 2018 to EC 1.14.15.29
Pathway
ec01120 Microbial metabolism in diverse environments
Orthology
K15981 cholest-4-en-3-one 26-monooxygenase
Genes
MTO : MTCTRI2_3609(cyp125)
MBO : BQ2027_MB3575C(cyp125)
MBM : BCGMEX_3607c(cyp125)
MAVI : RC58_11070 RC58_16590
MAVU : RE97_11080 RE97_16625
MIT : OCO_05260 OCO_26450 OCO_44490
MIA : OCU_05300 OCU_26300 OCU_44240
MID : MIP_00975 MIP_04041 MIP_06760
MYO : OEM_05330 OEM_24920 OEM_44690
MCHI : AN480_02630 AN480_13920 AN480_23165
MIR : OCQ_05410 OCQ_25010 OCQ_45630
MMAL : CKJ54_02555 CKJ54_11950 CKJ54_21190
MMAN : MMAN_12530 MMAN_32680 MMAN_39010 MMAN_48220
MSER : MTY59_18030 MTY59_24570 MTY59_42330
MSA : Mycsm_03408 Mycsm_05668 Mycsm_05807
MMI : MMAR_2783(cyp125A6) MMAR_5032(cyp125A7)
MMAE : MMARE11_27030(cyp125A6) MMARE11_48420(cyp125A7)
MLI : MULP_02541(cyp125A6) MULP_05284(cyp125A7)
MPSE : MPSD_28660 MPSD_52310(cyp125)
MSHO : MSHO_05050(cyp125) MSHO_41800
MMC : Mmcs_2723 Mmcs_4572 Mmcs_4677
MKM : Mkms_2767 Mkms_4660 Mkms_4763
MJL : Mjls_2753 Mjls_4955 Mjls_5062
MMM : W7S_02575 W7S_12840 W7S_22405
MKN : MKAN_00770 MKAN_11895 MKAN_23385
MYV : G155_05185 G155_16110 G155_26175
MYE : AB431_16515 AB431_25900 AB431_26415
MHAD : B586_04585 B586_11505
MDX : BTO20_16195 BTO20_30765 BTO20_31395
MSHG : MSG_00803 MSG_02677 MSG_04530
MFJ : MFLOJ_05510 MFLOJ_32070 MFLOJ_40920
MSTO : MSTO_06820 MSTO_36070 MSTO_44890
MSIM : MSIM_21650 MSIM_29340 MSIM_43540 MSIM_50820
MSAK : MSAS_07800 MSAS_28870 MSAS_51740
MKU : I2456_00515 I2456_13730 I2456_25550
MLW : MJO58_04310 MJO58_14090 MJO58_24950
MXE : MYXE_06050(cyp125) MYXE_06850 MYXE_24960
MNV : MNVI_11210 MNVI_12270(cyp125) MNVI_41530
MPAG : C0J29_05145 C0J29_16030 C0J29_27600
MNM : MNVM_23840(cyp125_1) MNVM_23850(cyp125_2) MNVM_23940(cyp125_3) MNVM_24710 MNVM_32450
MGOR : H0P51_04720 H0P51_15080 H0P51_25680
MCOO : MCOO_09740 MCOO_26960 MCOO_45830 MCOO_49100
MBAI : MB901379_02574 MB901379_04423
MSEO : MSEO_08790(cyp125) MSEO_14890 MSEO_34240 MSEO_47480
MHEK : JMUB5695_00503(cyp125) JMUB5695_00597 JMUB5695_02405
MGAU : MGALJ_01050 MGALJ_16000 MGALJ_37000 MGALJ_38180
MLJ : MLAC_18500 MLAC_47630(cyp125)
MBRD : MBRA_20280 MBRA_21690 MBRA_38760
MMAM : K3U93_12860 K3U93_15220 K3U93_15265 K3U93_22525 K3U93_24190
MSPG : F6B93_00660 F6B93_11525 F6B93_12530 F6B93_15855 F6B93_20340 F6B93_20510
MOT : LTS72_10310 LTS72_16725 LTS72_28065
MPAA : MKK62_02560 MKK62_12590
MKY : IWGMT90018_09400 IWGMT90018_29370 IWGMT90018_44430 IWGMT90018_57170
MADI : A7U43_06895 A7U43_07415 A7U43_15580
MWU : PT015_06050 PT015_15405 PT015_24370
MYW : BVC93_00785 BVC93_09125 BVC93_26765
MYJ : BCA37_02880 BCA37_11190 BCA37_15940
MSM : MSMEG_3524 MSMEG_5853 MSMEG_5995
MSG : MSMEI_3443(cyp125) MSMEI_5695(cyp125) MSMEI_5834(cyp125)
MSB : LJ00_17530 LJ00_28945 LJ00_29640
MSN : LI99_17535 LI99_28950 LI99_29645
MSH : LI98_17540 LI98_28955 LI98_29650
MVA : Mvan_3012 Mvan_5151 Mvan_5258
MGI : Mflv_1508 Mflv_1607 Mflv_3290
MSP : Mspyr1_08920 Mspyr1_09930 Mspyr1_26180
MCB : Mycch_2866 Mycch_4512 Mycch_4638
MNE : D174_15365 D174_23810 D174_24505
MYN : MyAD_15090 MyAD_23355 MyAD_24040
MFT : XA26_10010 XA26_33020 XA26_53050(igrA)
MPHL : MPHLCCUG_00534 MPHLCCUG_00665 MPHLCCUG_02457
MVQ : MYVA_3054 MYVA_5033 MYVA_5168
MRH : MycrhN_0940 MycrhN_2286 MycrhN_2423 MycrhN_4947
MTHN : 4412656_02324 4412656_03978 4412656_04060(cyp125)
MHAS : MHAS_01888 MHAS_03637 MHAS_03739
MDU : MDUV_12120 MDUV_49370 MDUV_50510
MCHT : MCHIJ_19700 MCHIJ_38240
MAUU : NCTC10437_01632 NCTC10437_02873 NCTC10437_04909 NCTC10437_05013
MMAG : MMAD_29510 MMAD_47220 MMAD_48270
MMOR : MMOR_12170 MMOR_13290 MMOR_19000 MMOR_34080 MMOR_47980
MFX : MFAL_08660 MFAL_23500 MFAL_33000
MAIC : MAIC_05630 MAIC_06670 MAIC_28630
MIJ : MINS_00290 MINS_09780 MINS_27860
MALV : MALV_06950 MALV_42590 MALV_43690
MTY : MTOK_22340 MTOK_38170 MTOK_47940
MPSC : MPSYJ_16160 MPSYJ_17100 MPSYJ_35270
MARZ : MARA_08840 MARA_47760 MARA_49370
MGAD : MGAD_08800 MGAD_22900 MGAD_36130 MGAD_37260
MHEV : MHEL_28110 MHEL_28970 MHEL_39560 MHEL_52310
MSAR : MSAR_09920 MSAR_10700 MSAR_39810
MANY : MANY_14330 MANY_31860 MANY_32710(cyp125)
MAUB : MAUB_06600 MAUB_26480
MPOF : MPOR_34500 MPOR_52540 MPOR_53560
MPHU : MPHO_06000 MPHO_43880
MMUC : C1S78_015340 C1S78_025350
MMAT : MMAGJ_34710 MMAGJ_35720 MMAGJ_65550
MBOK : MBOE_04320 MBOE_21060 MBOE_41450
MFG : K6L26_05610 K6L26_06165 K6L26_15795 K6L26_16775
MSEI : MSEDJ_01010 MSEDJ_02110 MSEDJ_42870
MFLV : NCTC10271_00498 NCTC10271_00616 NCTC10271_02462
MCEE : MCEL_07300 MCEL_38100 MCEL_39290
MMON : EWR22_14470 EWR22_24750 EWR22_25305
MGO : AFA91_10815 AFA91_11455 AFA91_22195
MHOL : K3U96_03255 K3U96_03790 K3U96_12335
MSEN : K3U95_12890 K3U95_13570 K3U95_24665 K3U95_25225
MPAE : K0O64_15625 K0O64_25340 K0O64_25910
MRF : MJO55_14510 MJO55_23470 MJO55_23975
MDF : K0O62_15485 K0O62_25025 K0O62_25750
MCRO : MI149_16585 MI149_25630 MI149_26220
MGRO : FZ046_02195 FZ046_02785 FZ046_20385
MAUS : JN090_14345 JN090_25590 JN090_26370
MFRE : EXE63_18935 EXE63_19500 EXE63_28710
MKR : MKOR_35680 MKOR_35690(cyp125) MKOR_37070
MPAK : MIU77_02130 MIU77_02135 MIU77_02670 MIU77_05555 MIU77_08185
MAB : MAB_0101 MAB_0611 MAB_0613 MAB_1211c
MMV : MYCMA_0317 MYCMA_0319 MYCMA_0648 MYCMA_13860
MABB : MASS_0104 MASS_0581 MASS_0583 MASS_1209
MABL : MMASJCM_0105 MMASJCM_0600 MMASJCM_0603 MMASJCM_0964 MMASJCM_1238
MCHE : BB28_00505 BB28_02925 BB28_02935 BB28_06010
MIZ : BAB75_00800 BAB75_03675 BAB75_03685 BAB75_06600
MSTE : MSTE_00101 MSTE_00570 MSTE_00572 MSTE_01177
MSAO : MYCSP_02625 MYCSP_02635 MYCSP_05345 MYCSP_15860
MSAL : DSM43276_00080 DSM43276_00529 DSM43276_00531 DSM43276_01077
MJD : JDM601_2803(cyp125A7) JDM601_3609(cyp125A7) JDM601_3682(cyp125A7) JDM601_3692(cyp125A7) JDM601_3693(cyp125A7)
MTER : 4434518_02769(cyp125A7_1) 4434518_03588(cyp125A7_2) 4434518_03654(cyp125A7_3) 4434518_03664(cyp125A7_4) 4434518_03665(cyp125A7_5)
MMIN : MMIN_05220 MMIN_11390 MMIN_12150
MHIB : MHIB_22420 MHIB_30110 MHIB_30720(cyp125) MHIB_30810
MHER : K3U94_16065 K3U94_20385 K3U94_20795 K3U94_20850
MVM : MJO54_16140 MJO54_20300 MJO54_20710 MJO54_20755
NFA : NFA_24320 NFA_25870 NFA_5180
NFR : ERS450000_01508 ERS450000_03713
NCY : NOCYR_0531 NOCYR_2255(cyp) NOCYR_4383
NBR : O3I_002870 O3I_010355 O3I_020195
NNO : NONO_c05330 NONO_c15420 NONO_c20300 NONO_c31770
NSL : BOX37_02330 BOX37_04650 BOX37_22005
NSR : NS506_00434 NS506_01300 NS506_05365
NTP : CRH09_03475 CRH09_16495
NOZ : DMB37_00315 DMB37_23770 DMB37_31215
NOD : FOH10_10445 FOH10_11500 FOH10_28500 FOH10_29905
NAH : F5544_02805 F5544_08550 F5544_13885
NAD : NCTC11293_01279 NCTC11293_01796
NWL : NWFMUON74_05270(cyp125) NWFMUON74_28890 NWFMUON74_42500
NIE : KV110_03190 KV110_10815 KV110_20625 KV110_22925
NTC : KHQ06_03465 KHQ06_07690 KHQ06_21070
NHU : H0264_02870 H0264_04035 H0264_19920 H0264_25955 H0264_32670
NYA : LTV02_01210 LTV02_14405 LTV02_19940 LTV02_28700 LTV02_29850
NGP : LTT66_03460 LTT66_15685 LTT66_31145
NSPU : IFM12276_02110 IFM12276_41710 IFM12276_46530
NYU : D7D52_03585 D7D52_04685 D7D52_07730
RHA : RHA1_ro04667 RHA1_ro04679
RER : RER_09260 RER_15090 RER_33720
REY : O5Y_04125 O5Y_07155 O5Y_15535
REB : XU06_04370 XU06_07400 XU06_15770
RQI : C1M55_04605 C1M55_07640 C1M55_16785
ROA : Pd630_LPD01173 Pd630_LPD01185
RBY : CEJ39_05740 CEJ39_06610
RAV : AAT18_04130 AAT18_05705
RRZ : CS378_19765 CS378_20940
RHQ : IM25_09115 IM25_09940
RHOD : AOT96_15010 AOT96_18030 AOT96_26970
RRT : 4535765_00647 4535765_00829
RCR : NCTC10994_01888 NCTC10994_02073
RKO : JWS14_25860 JWS14_25920
RGO : KYT97_05625 KYT97_11055 KYT97_24330
ROZ : CBI38_04900 CBI38_04960
RPSK : JWS13_18580 JWS13_18640
RGOR : NMQ04_02860 NMQ04_03600
RHOO : RA302_04475 RA302_07545 RA302_15995
RHOU : KZJ41_04125 KZJ41_06245
RHOW : A4U64_18845 A4U64_20645
RHOJ : JVH1_12855 JVH1_12915
RHOS : QWW67_21465 QWW67_23190
RHOQ : QWW98_21475 QWW98_23200
RHOY : QNA09_01675 QNA09_03510
RHOH : CPI83_13215 CPI83_21635 CPI83_24610
REQ : REQ_07240 REQ_09130 REQ_27290
PSOW : ABI214_10020 ABI214_25120 ABI214_25220
WHR : OG579_07835 OG579_09325 OG579_13015
GPO : GPOL_c42820 GPOL_c42860
GRU : GCWB2_19940 GCWB2_19965
GOM : D7316_04508 D7316_04509 D7316_04513
GAV : C5O27_08150 C5O27_08170
GOD : GKZ92_18870 GKZ92_18890
GAM : GII34_18850 GII34_18870 GII34_18875
GPD : GII33_03870 GII33_03890
GJI : H1R19_18800 H1R19_18820
GOI : LK459_13780 LK459_13805
GAMI : IHQ52_22885 IHQ52_22905
GMG : NWF22_06365 NWF22_06385
SPIN : KV203_10830 KV203_17190
DIT : C3V38_06275 C3V38_09410
DIZ : CT688_03330 CT688_17055
DPC : A6048_03280 A6048_17675
DLU : A6035_03570 A6035_17000
DKN : NHB83_03140 NHB83_17275
DCD : VYL96_03355 VYL96_16720
TOY : FO059_13835 FO059_15220 FO059_16580
SAUH : SU9_009535 SU9_027555
NANO : G5V58_09915 G5V58_09920
NMAR : HPC71_09655 HPC71_09660
NFC : KG111_08445 KG111_08455
NBI : SHK19_12330 SHK19_12335
NOCR : OSR43_09700 OSR43_09705
ACTW : F7P10_32425 F7P10_32430
AMAZ : LUW76_38130 LUW76_38135
ACIR : OG979_07925 OG979_07930
SPIQ : OHA34_28025 OHA34_31840 OHA34_31845 OHA34_31865
ACTQ : OG417_15045 OG417_15050 OG417_34220
FRI : FraEuI1c_1505 FraEuI1c_5098
AMYD : K1T34_30925 K1T34_52240
AQZ : KSP35_04805 KSP35_04815 KSP35_14595
IAM : HC251_10060 HC251_15180 HC251_17255 HC251_23270
IMA : PO878_12445 PO878_16050 PO878_16685 PO878_20710
» show all
Taxonomy
Reference
Authors
Rosloniec KZ, Wilbrink MH, Capyk JK, Mohn WW, Ostendorf M, van der Geize R, Dijkhuizen L, Eltis LD
Title
Cytochrome P450 125 (CYP125) catalyses C26-hydroxylation to initiate sterol side-chain degradation in Rhodococcus jostii RHA1.
Journal
Sequence
Reference
Authors
McLean KJ, Lafite P, Levy C, Cheesman MR, Mast N, Pikuleva IA, Leys D, Munro AW
Title
The Structure of Mycobacterium tuberculosis CYP125: molecular basis for cholesterol binding in a P450 needed for host infection.
Journal
Sequence
Reference
Authors
Capyk JK, Kalscheuer R, Stewart GR, Liu J, Kwon H, Zhao R, Okamoto S, Jacobs WR Jr, Eltis LD, Mohn WW
Title
Mycobacterial cytochrome p450 125 (cyp125) catalyzes the terminal hydroxylation of c27 steroids.
Journal
Sequence
Reference
Authors
Ouellet H, Guan S, Johnston JB, Chow ED, Kells PM, Burlingame AL, Cox JS, Podust LM, de Montellano PR
Title
Mycobacterium tuberculosis CYP125A1, a steroid C27 monooxygenase that detoxifies intracellularly generated cholest-4-en-3-one.
Journal
Sequence
Other DBs