KEGG   ENZYME: 1.14.15.29
Entry
EC 1.14.15.29               Enzyme                                 
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
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
ec00984  Steroid degradation
ec01120  Microbial metabolism in diverse environments
Orthology
K15981  cholest-4-en-3-one 26-monooxygenase
Genes
AFUSEYZ66_06325
MSDMYSTI_04828
MTURv3545c(cyp125)
MTVRVBD_3545c
MTCMT3649
MRAMRA_3584(cyp125)
MTFTBFG_13578
MTBTBMG_03584
MTKTBSG_03611
MTZTBXG_003560
MTIMRGA423_22410
MTECCDC5079_3286
MTURCFBS_3761(cyp125)
MTLCCDC5180_3238
MTOMTCTRI2_3609(cyp125)
MTDUDA_3545c(cyp125)
MTNERDMAN_3890(cyp125)
MTJJ112_19085
MTUBMT7199_3607
MTUCJ113_24790
MTUEJ114_18960
MTXM943_18225
MTULTBHG_03485
MTUTHKBT1_3746(cyp125)
MTUUHKBT2_3755(cyp125)
MTQHKBS1_3758(cyp125)
MBOBQ2027_MB3575C(cyp125)
MBBBCG_3609c(cyp125)
MBTJTY_3610(cyp125)
MBMBCGMEX_3607c(cyp125)
MBKK60_036830
MBXBCGT_3411
MAFMAF_35570(cyp125)
MMICRN08_3921
MCEMCAN_35561(cyp125)
MCQBN44_110037(cyp)
MCVBN43_90043(cyp)
MCXBN42_90040(cyp)
MCZBN45_100040(cyp)
MPAMAP_0522 MAP_1614c
MAOMAP4_2225 MAP4_3345
MAVIRC58_11070 RC58_16590
MAVURE97_11080 RE97_16625
MAVMAV_0616 MAV_2811
MITOCO_05260 OCO_26450 OCO_44490
MIAOCU_05300 OCU_26300 OCU_44240
MIDMIP_00975 MIP_04041 MIP_06760
MYOOEM_05330 OEM_24920 OEM_44690
MCHIAN480_02630 AN480_13920 AN480_23165
MIROCQ_05410 OCQ_25010 OCQ_45630
MMALCKJ54_02555 CKJ54_11950 CKJ54_21190
MLPMLM_0760
MMANMMAN_12530 MMAN_32680 MMAN_39010 MMAN_48220
MSAMycsm_03408 Mycsm_05668 Mycsm_05807
MULMUL_4106(cyp125A7)
MMCMmcs_2723 Mmcs_4572 Mmcs_4677
MKMMkms_2767 Mkms_4660 Mkms_4763
MJLMjls_2753 Mjls_4955 Mjls_5062
MMIMMAR_2783(cyp125A6) MMAR_5032(cyp125A7)
MMAEMMARE11_27030(cyp125A6) MMARE11_48420(cyp125A7)
MMMW7S_02575 W7S_12840 W7S_22405
MLIMULP_02541(cyp125A6) MULP_05284(cyp125A7)
MKNMKAN_00770 MKAN_11895 MKAN_23385
MYVG155_05185 G155_16110 G155_26175
MYEAB431_16515 AB431_25900 AB431_26415
MGOAFA91_10815 AFA91_11455 AFA91_22195
MHADB586_04585 B586_11505
MDXBTO20_16195 BTO20_30765 BTO20_31395
MSHGMSG_00803 MSG_02677 MSG_04530
MFJMFLOJ_05510 MFLOJ_32070 MFLOJ_40920
MSTOMSTO_06820 MSTO_36070 MSTO_44890 MSTO_59430
MSIMMSIM_21650 MSIM_29340 MSIM_43540 MSIM_50820
MSAKMSAS_07800 MSAS_28870 MSAS_51740
MKUI2456_00515 I2456_13730 I2456_25550
MGROFZ046_02195 FZ046_02785 FZ046_20385
MXEMYXE_06050(cyp125) MYXE_06850 MYXE_24960
MNVMNVI_11210 MNVI_12270(cyp125) MNVI_41530
MPAGC0J29_05145 C0J29_16030 C0J29_27600
MNMMNVM_23840(cyp125_1) MNVM_23850(cyp125_2) MNVM_23940(cyp125_3) MNVM_24710 MNVM_32450
MGORH0P51_04720 H0P51_15080 H0P51_25680
MCOOMCOO_09740 MCOO_26960 MCOO_45830 MCOO_49100
MBAIMB901379_02574 MB901379_04423
MSEOMSEO_08790(cyp125) MSEO_14890 MSEO_34240 MSEO_47480
MPSEMPSD_28660 MPSD_52310(cyp125)
MSHOMSHO_05050(cyp125) MSHO_41800
MHEKJMUB5695_00503(cyp125) JMUB5695_00597 JMUB5695_02405
MGAUMGALJ_01050 MGALJ_16000 MGALJ_37000 MGALJ_38180
MLJMLAC_18500 MLAC_47630(cyp125)
MBRDMBRA_20280 MBRA_21690 MBRA_38760
MSHJMSHI_38950(cyp125)
MKRMKOR_35680 MKOR_35690(cyp125) MKOR_37070
MDFK0O62_15485 K0O62_25025 K0O62_25750
MMAMK3U93_12860 K3U93_15220 K3U93_15265 K3U93_22525 K3U93_24190
MHOLK3U96_03255 K3U96_03790 K3U96_12335
MHERK3U94_16065 K3U94_20385 K3U94_20795 K3U94_20850
MSENK3U95_12890 K3U95_13570 K3U95_24665 K3U95_25225
MPAEK0O64_15625 K0O64_25340 K0O64_25910
MSPGF6B93_00660 F6B93_11525 F6B93_12530 F6B93_15855 F6B93_20340 F6B93_20510
MOTLTS72_10310 LTS72_16725 LTS72_28065
MSMMSMEG_3524 MSMEG_5853 MSMEG_5995
MSGMSMEI_3443(cyp125) MSMEI_5695(cyp125) MSMEI_5834(cyp125)
MSBLJ00_17530 LJ00_28945 LJ00_29640
MSNLI99_17535 LI99_28950 LI99_29645
MSHLI98_17540 LI98_28955 LI98_29650
MVAMvan_3012 Mvan_5151 Mvan_5258
MGIMflv_1508 Mflv_1607 Mflv_3290
MSPMspyr1_08920 Mspyr1_09930 Mspyr1_26180
MCBMycch_2866 Mycch_4512 Mycch_4638
MNED174_15365 D174_23810 D174_24505
MYNMyAD_15090 MyAD_23355 MyAD_24040
MFTXA26_10010 XA26_33020 XA26_53050(igrA)
MPHLMPHLCCUG_00534 MPHLCCUG_00665 MPHLCCUG_02457
MVQMYVA_3054 MYVA_5033 MYVA_5168
MLLB1R94_24550
MRHMycrhN_0940 MycrhN_2286 MycrhN_2423 MycrhN_4947
MTHN4412656_02324 4412656_03978 4412656_04060(cyp125)
MHASMHAS_01888 MHAS_03637 MHAS_03739
MDUMDUV_12120 MDUV_49370 MDUV_50510
MCHTMCHIJ_19700 MCHIJ_38240
MAUUNCTC10437_01632 NCTC10437_02873 NCTC10437_04909 NCTC10437_05013
MMAGMMAD_29510 MMAD_47220 MMAD_48270
MMORMMOR_10100 MMOR_10220 MMOR_12170 MMOR_13290 MMOR_19000 MMOR_34080 MMOR_47980
MFXMFAL_08660 MFAL_23500 MFAL_33000
MAICMAIC_05630 MAIC_06670 MAIC_28630
MIJMINS_00290 MINS_09780 MINS_27860
MALVMALV_06950 MALV_42590 MALV_43690
MTYMTOK_22340 MTOK_38170 MTOK_47940
MPSCMPSYJ_16160 MPSYJ_17100 MPSYJ_35270
MARZMARA_08840 MARA_47760 MARA_49370
MGADMGAD_08800 MGAD_22900 MGAD_36130 MGAD_37260
MHEVMHEL_28110 MHEL_28970 MHEL_39560 MHEL_52310
MSARMSAR_09920 MSAR_10700 MSAR_39810
MANYMANY_14330 MANY_31860 MANY_32710(cyp125)
MAUBMAUB_06600 MAUB_26480
MPOFMPOR_34500 MPOR_52540 MPOR_53560
MPHUMPHO_06000 MPHO_43880
MMUCC1S78_015340 C1S78_025350
MMATMMAGJ_34710 MMAGJ_35720 MMAGJ_65550
MBOKMBOE_04320 MBOE_21060 MBOE_41450
MFGK6L26_05610 K6L26_06165 K6L26_15795 K6L26_16775
MSEIMSEDJ_01010 MSEDJ_02110 MSEDJ_42870
MFLVNCTC10271_00498 NCTC10271_00616 NCTC10271_02462
MABMAB_0101 MAB_0611 MAB_0613 MAB_1211c
MMVMYCMA_0317 MYCMA_0319 MYCMA_0648 MYCMA_13860
MABBMASS_0104 MASS_0581 MASS_0583 MASS_1209
MABLMMASJCM_0105 MMASJCM_0600 MMASJCM_0603 MMASJCM_0964 MMASJCM_1238
MCHEBB28_00505 BB28_02925 BB28_02935 BB28_06010
MIZBAB75_00800 BAB75_03675 BAB75_03685 BAB75_06600
MSTEMSTE_00101 MSTE_00570 MSTE_00572 MSTE_01177
MSAOMYCSP_02625 MYCSP_02635 MYCSP_05345 MYCSP_15860
MSALDSM43276_00080 DSM43276_00529 DSM43276_00531 DSM43276_01077
MJDJDM601_2803(cyp125A7) JDM601_3609(cyp125A7) JDM601_3682(cyp125A7) JDM601_3692(cyp125A7) JDM601_3693(cyp125A7)
MTER4434518_02769(cyp125A7_1) 4434518_03588(cyp125A7_2) 4434518_03654(cyp125A7_3) 4434518_03664(cyp125A7_4) 4434518_03665(cyp125A7_5)
MMINMMIN_05220 MMIN_11390 MMIN_12150
MHIBMHIB_22420 MHIB_30110 MHIB_30720(cyp125) MHIB_30810
ASDAS9A_0965
MPAKMIU77_02130 MIU77_02135 MIU77_02670 MIU77_05555 MIU77_08185
CSURN24_0159
NFANFA_24320 NFA_25870 NFA_5180
NFRERS450000_01508 ERS450000_03713
NCYNOCYR_0531 NOCYR_2255(cyp) NOCYR_4383
NBRO3I_002870 O3I_010355 O3I_020195
NNONONO_c05330 NONO_c15420 NONO_c20300 NONO_c31770
NSLBOX37_02330 BOX37_04650 BOX37_22005
NSRNS506_00434 NS506_01300 NS506_05365
NTPCRH09_03475 CRH09_16495
NOZDMB37_00315 DMB37_23770 DMB37_31215
NODFOH10_10445 FOH10_11500 FOH10_28500 FOH10_29905
NAHF5544_02805 F5544_08550 F5544_13885
NADNCTC11293_01279 NCTC11293_01796
NWLNWFMUON74_05270(cyp125) NWFMUON74_28890 NWFMUON74_42500
NIEKV110_03190 KV110_10815 KV110_20625 KV110_22925
NTCKHQ06_03465 KHQ06_07690 KHQ06_21070
NHUH0264_02870 H0264_04035 H0264_19920 H0264_25955 H0264_32670
NYALTV02_01210 LTV02_14405 LTV02_19940 LTV02_28700 LTV02_29850
NGPLTT66_03460 LTT66_15685 LTT66_31145
RHARHA1_ro04667 RHA1_ro04679
RERRER_09260 RER_15090 RER_33720
REYO5Y_04125 O5Y_07155 O5Y_15535
REBXU06_04370 XU06_07400 XU06_15770
RQIC1M55_04605 C1M55_07640 C1M55_16785
ROPROP_47660 ROP_47780
ROAPd630_LPD01173 Pd630_LPD01185
REQREQ_07240 REQ_09130 REQ_27290
RPYY013_19380
RBYCEJ39_05740 CEJ39_06610
RAVAAT18_04130 AAT18_05705
RHWBFN03_14725
RRZCS378_19765 CS378_20940
RHQIM25_09115 IM25_09940
RHODAOT96_15010 AOT96_18030 AOT96_26970
RRT4535765_00647 4535765_00829
RCRNCTC10994_01888 NCTC10994_02073
RTMG4H71_07045
RKOJWS14_25860 JWS14_25920
RGOKYT97_05625 KYT97_11055 KYT97_24330
GBRGbro_3970 Gbro_3974
GPOGPOL_c42820 GPOL_c42860
GORKTR9_3902(cyp125A1)
GOQACH46_17490
GTABCM27_20455
GOCCXX93_00535
GITC6V83_03930
GRUGCWB2_19940 GCWB2_19965
GOMD7316_04508 D7316_04509 D7316_04513
GAVC5O27_08150 C5O27_08170
GODGKZ92_18870 GKZ92_18890
GAMGII34_18850 GII34_18870 GII34_18875
GPDGII33_03870 GII33_03890
GJIH1R19_18800 H1R19_18820
GOILK459_13780 LK459_13805
SPINKV203_10830 KV203_17190
TPRTpau_3821
TSMASU32_21780
DTMBJL86_0735
DITC3V38_06275 C3V38_09410
DIZCT688_03330 CT688_17055
DPCA6048_03280 A6048_17675
DLUA6035_03570 A6035_17000
TOYFO059_13835 FO059_15220 FO059_16580
SMASAVERM_5841(cyp22)
SGRSGR_5169
SGBWQO_09525
SCBSCAB_65311
SVLStrvi_7419
SRCM271_33995
SMALSMALA_2275
SSOII1A49_14545
SCTSCAT_1444(cyp)
SCYSCATT_14470
SBHSBI_07560(cyp37)
SVESVEN_2047
SDVBN159_6030(cyp125)
SFISFUL_1917
SCIB446_12240
SALUDC74_2810
SALLSAZ_15430
STREGZL_06167
SLDT261_5756
SLCSL103_07525
STRMM444_11810
SPRISPRI_5168
SCZABE83_26245
SCXAS200_30925
SRWTUE45_02924
SCLFBB341_20395
SGSAVL59_38775
STSIA4E84_12135
SALWCP975_10455
SGMGCM10017557_58210
SCADDN051_26755
SLSSLINC_2675
SNRSNOUR_28615(cyp125)
SPLULK06_008595
SAUOBV401_14835
SSIAA7J05_25220
SVUB1H20_08570
SPUNBFF78_29375
SGVB1H19_13495
SLAUSLA_1953
SALFSMD44_02573
SALJSMD11_4755
SLXSLAV_25570
STROSTRMOE7_12495
SFKKY5_2401
SNZDC008_09955
SGEDWG14_05955
SRJSRO_5110
SLKSLUN_11575
SDXC4B68_28195
SGDELQ87_27615
SQZFQU76_08425
SCYAEJ357_13700
STIRDDW44_05615
SKACP970_30575
SGZC0216_24630
SVNCP980_23215
SHAWCEB94_12585
SRKFGW37_09970
SFICEIZ62_23415
SGALCP966_10520
SSPODDQ41_04610
SFYGFH48_28195
SAQUEJC51_15530
SGFHEP81_05415
SCAVCVT27_08435
SRIMCP984_28545
SSUBCP968_23110
SPHVF9278_12310
STSUB7R87_08360
SCHACP983_30410
SGXH4W23_12115
SCOECP976_13630
SSPBCP982_13670
SNFJYK04_03039
SPLACP981_11780
SBROGQF42_14680
STUIGCM10017668_19740
SATAC5746_12920
SHUNDWB77_05376
SCYGS1361_12965
SFEUIM697_09955
SDWK7C20_11185
SCALI6J39_08770
SAUHSU9_009535 SU9_027555
SPEUCGZ69_10475
SROIIAG44_28495
SXNIAG42_24920
SHKJ2N69_10320
SANUK7396_25290
STRYEQG64_08555
KABB7C62_08510
YIALO772_04365
NCANoca_2739
NDKI601_3461 I601_3462
NBEBack2_27700
NANOG5V58_09915 G5V58_09920
NAROCFH99_13390
NPIG7071_15770
PSIMKR76_14335
AEBC6I20_03435
NGVCDO52_23700
TCUTcur_3656
ACTWF7P10_32425 F7P10_32430
AGRAAGRA3207_006097
SROSros_8218 Sros_8869
NOABKM31_52815
NOWGBF35_43300
NCXNocox_35605
NGNLCN96_48545
FRIFraEuI1c_1505 FraEuI1c_5098
SACGFDZ84_22810
AMDAMED_2551
AMNRAM_12965
AMMAMES_2524
AMZB737_2525
AOIAORI_2528
AJAAJAP_26185(cyp125)
AMQAMETH_4822
AMYCCU254_10555
AMYBBKN51_05250
AABA4R43_15925
AMYYYIM_14520
AORISD37_13695
AACDLWP59_29050
KALKALB_3393
KPHYAOZ06_42520
LEDBBK82_38815
ALOCRK59579
PMADBAY61_10985
SACEGIY23_13310
STPStrop_2612
SAQSare_2811
AMSAMIS_19330
AIHAiant_18690
CAICaci_0773
ABAIIMCC26256_11916
AQZKSP35_04805 KSP35_04815 KSP35_14595
IAMHC251_10060 HC251_15180 HC251_17255 HC251_23270
 » show all
Reference
1  [PMID:19843222]
  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
Mol Microbiol 74:1031-43 (2009)
DOI:10.1111/j.1365-2958.2009.06915.x
  Sequence
Reference
2  [PMID:19846552]
  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
J Biol Chem 284:35524-33 (2009)
DOI:10.1074/jbc.M109.032706
  Sequence
[mtu:Rv3545c]
Reference
3  [PMID:19846551]
  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
J Biol Chem 284:35534-42 (2009)
DOI:10.1074/jbc.M109.072132
  Sequence
[mtu:Rv3545c]
Reference
4  [PMID:20545858]
  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
Mol Microbiol 77:730-42 (2010)
DOI:10.1111/j.1365-2958.2010.07243.x
  Sequence
[mtu:Rv3545c]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.15.29
IUBMB Enzyme Nomenclature: 1.14.15.29
ExPASy - ENZYME nomenclature database: 1.14.15.29
BRENDA, the Enzyme Database: 1.14.15.29

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