Entry
Name
sterol 14alpha-demethylase;
obtusufoliol 14-demethylase;
lanosterol 14-demethylase;
lanosterol 14alpha-demethylase;
sterol 14-demethylase;
CYP51 (gene name);
ERG11 (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
sterol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (14-methyl cleaving)
Reaction(IUBMB)
a 14alpha-methylsteroid + 3 [reduced NADPH---hemoprotein reductase] + 3 O2 = a Delta14-steroid + formate + 3 [oxidized NADPH---hemoprotein reductase] + 4 H2O (overall reaction) [RN:
R12118 ];
(1a) a 14alpha-methylsteroid + [reduced NADPH---hemoprotein reductase] + O2 = a 14alpha-hydroxymethylsteroid + [oxidized NADPH---hemoprotein reductase] + H2O [RN:
R12119 ];
(1b) a 14alpha-hydroxysteroid + [reduced NADPH---hemoprotein reductase] + O2 = a 14alpha-formylsteroid + [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:
R12120 ];
(1c) a 14alpha-formylsteroid + [reduced NADPH---hemoprotein reductase] + O2 = a Delta14-steroid + formate + [oxidized NADPH---hemoprotein reductase] + H2O [RN:
R12121 ]
Reaction(KEGG)
Substrate
14alpha-methylsteroid [CPD:
C21918 ];
[reduced NADPH---hemoprotein reductase] [CPD:
C03024 ];
O2 [CPD:
C00007 ];
14alpha-hydroxysteroid;
14alpha-formylsteroid [CPD:
C21921 ]
Product
Delta14-steroid [CPD:
C21919 ];
formate [CPD:
C00058 ];
[oxidized NADPH---hemoprotein reductase] [CPD:
C03161 ];
H2O [CPD:
C00001 ];
14alpha-hydroxymethylsteroid [CPD:
C21920 ];
14alpha-formylsteroid [CPD:
C21921 ]
Comment
This cytochrome P-450 (heme-thiolate) enzyme acts on a range of steroids with a 14alpha-methyl group, such as obtusifoliol and lanosterol. The enzyme catalyses a hydroxylation and a reduction of the 14alpha-methyl group, followed by a second hydroxylation, resulting in the elimination of formate and formation of a 14(15) double bond.
History
EC 1.14.14.154 created 2001 as EC 1.14.13.70, modified 2013, transferred 2018 EC 1.14.14.154
Pathway
ec01110 Biosynthesis of secondary metabolites
Orthology
K05917 sterol 14alpha-demethylase
K26422 Mimiviridae probable sterol 14alpha-demethylase
Genes
PON : 100171776(CYP51A1) 100456763
PPYG : 129011499 129040053
CJC : 100403815(CYP51A1) 103792683
DORD : 105992921 105992922
PLOP : 125346994 125366408
PALE : 102886107 102893984
AVIT : 104278257 104280066
XLA : 100037098(cyp51a1.L) 447600(cyp51a1.S)
CAUA : 113062450 113062498
PPRM : 120475269 120475282
AOCE : 111565075 129350737
SASA : 106570209 106588568
STRU : 115173678 115175799
OCLA : 139373536 139392242
SALP : 111955261 111955711
CCLU : 121585442 123491395
ARUT : 117399525 117435357 117972329
AFIL : 140144500 140151437 140166569 140167009 140169011
TAD : TRIADDRAFT_22633 TRIADDRAFT_22681
CSAT : 104706593 104736309 104739814 104755421 104770430
BRP : 103836218 103842743 103871918
BNA : 106346420 106351696 106353584 106362160 106389549 106401015 111206219 125580295 125597274 125604033
BOE : 106295599 106308893 106311516 106320657 106328416
MINC : 123193412 123193486
GHI : 107896963 107909508 107941348 107946187
HSYR : 120178097 120204605 120216110
LANG : 109325265 109354455
MSYL : 126596405 126607434
PCOX : 137731153 137737217
MNT : 112090429 112094949 112095178 21386253
CMAX : 111470769 111480132
CMOS : 111439144 111457642
CPEP : 111790760 111799880
MESC : 110603980 110621258
PALZ : 118042716 118054407
JRE : 108997326 109006716 118344169
CILL : 122310454 122313495
NTA : 107764727(CYP51) 107779000(NtCYP51-2)
SIND : 105168491 105169754
SSPL : 121746430 121753326 121796468
SHIS : 125188731 125208650
CCAV : 112502448 112527780
CQI : 110688005 110689907 110720468 110721571 110726681 110728819 110728821 110728822
ATRI : 130798023 130798024
PSOM : 113309841 113321918
OSA : 107275589 107275872 112939725 4328054 4329175 4338097 4338803 4350614 9269876
DOSA : Os02g0113200 Os02g0323600 Os05g0211100 Os05g0416400 Os11g0525200
OBR : 102702392 102706941 102708311 102716753 102721945 102722234
OGL : 127754779 127761435 127763905 127772999 127773122 127774833 127780294
BDI : 100830263 100832594 100838679 100844089 100844692 100845001
ATS : 109733821 109738711 109739759 109743781 109745900 109746137 109748891 109751861 109756453 109759247 109759248 109759250 109759976 109770960 109772803 109776878 109777128 109782869 109787201 123493873
TDC : 119266702 119274369 119286258 119288375 119294231 119294333 119295519 119296732 119296769 119297269 119298738 119298739 119300208 119300586 119306979 119306981 119306983 119307202 119333619 119341833 119352065 119354101 119357397 119358548 119360211 119361868 119366884
TAES : 123038761 123039975 123040112 123043241 123048215 123048277 123048512 123049129 123051110 123056613 123064331 123067667 123074048 123075309 123076015 123086443 123089615 123089617 123089618 123089804 123089860 123090354 123091557 123096508 123100632 123100717 123100829 123101880 123101938 123101939 123101944 123106269 123110066 123115397 123115399 123115526 123119044 123119068 123124059 123124070 123124071 123160214 123163206 123187057 123188223 123191311
TUA : 125506823 125506824 125506825 125516273 125523155 125524664 125524708 125527673 125529024 125529326 125530453 125532590 125532592 125540581 125540619 125541352 125551117 125555410
LPER : 127294404 127295438 127299218 127306063 127306159 127313503 127314227 127317243 127329577 127329907 127330913 127331249 127333022 127335184 127336786 127344539 127349289 139830038 139833416 139835750
LRD : 124647099 124648856 124655801 124657931 124670142 124670456 124670963 124670964 124671190 124671191 124672710 124673024 124673278 124673541 124674437 124674438 124675753 124680401 124693155 124693158 124694294 124703283 124704244 124704676 124704705 124706278
SBI : 8054926 8062049 8062644 8062646 8062647 8062648 8062649 8064404 8071833 8074834 8081764 8083151 8084212
ZMA : 100191975 100273258 100382691 100383359 103635655 103652962 109946003
MFLO : 136480252 136480255 136482466 136489212 136490131 136499815 136503511 136503827 136504197 136504567 136509573 136535066 136535067 136535068 136545988 136549063 136551568
SITA : 101767793 101783068 101783468 101784673
SVS : 117833165 117833335 117833927 117844149
PVIR : 120644517 120644719 120659196 120662878 120686895
PHAI : 112879791 112879821 112887680 112895459 112902479 112902990
PAUA : 133886705 133892008 133900001 133900429
MUS : 103987267 135612650 135624677
ACAK : 137953921 137962421
NCOL : 116248841 116257357
SMO : SELMODRAFT_155290 SELMODRAFT_178739(CYP51G1)
KMX : KLMA_20551(CYP707A7)
VPO : Kpol_1004p61 Kpol_1023p61
NCS : NCAS_0G00960(NCAS0G00960)
NDI : NDAI_0F01100(NDAI0F01100)
TPF : TPHA_0D02710(TPHA0D02710)
TBL : TBLA_0E02810(TBLA0E02810)
TDL : TDEL_0A04550(TDEL0A04550)
KAF : KAFR_0C05720(KAFR0C05720)
KNG : KNAG_0B03340(KNAG0B03340)
LBG : 92205256(LODBEIA_P00600) 92206304(LODBEIA_P11080) 92206423(LODBEIA_P12270) 92207256(LODBEIA_P20600) 92208333(LODBEIA_P31370) 92209064(LODBEIA_P38680) 92209874(LODBEIA_P46780) 92209993(LODBEIA_P47970) 92210898(LODBEIA_P57020)
CAL : CAALFM_C500660CA(ERG11)
ASAU : 88175893(PUMCH_004833)
BBRX : BRETT_002515(ERG11)
YLI : 2906856(YALI2_C00221g)
NTE : NEUTE1DRAFT119039(NEUTE1DRAFT_119039)
SMP : 10803582(SMAC4_05737)
PBEL : QC761_104470(ERG11)
PPSD : QC762_104470(ERG11)
PPSP : QC763_104470(ERG11)
PPSA : QC764_104470(ERG11)
RTHE : 98125739(VTJ83DRAFT_459)
PGRI : PgNI_02936 PgNI_04906
TMN : UCRPA7_2412 UCRPA7_7986 UCRPA7_8689
FGR : FGSG_01000 FGSG_04092 FGSG_11024
FPU : FPSE_00109 FPSE_01496 FPSE_02459
FPOA : FPOAC1_001080(CYP51_1) FPOAC1_006536(CYP51_2) FPOAC1_009798
FVN : FVRRES_01262 FVRRES_07143 FVRRES_10451
FVR : FVEG_01123 FVEG_10277 FVEG_12391
FOX : FOXG_00394 FOXG_11545 FOXG_13138
NHE : NECHADRAFT_41888 NECHADRAFT_43488 NECHADRAFT_57370
FFC : NCS54_00085400 NCS54_00743700
FMU : J7337_000889(CYP51B) J7337_007737 J7337_011546(CYP51A)
TATV : 25778749(TrAtP1_007834) 25784813(TrAtP1_007176)
MBRN : 26240771(CP51) 26247057(CP51)
PCHM : VFPPC_00539 VFPPC_17614
AMUS : LMH87_001019 LMH87_005964
PLJ : 28885295(PLICBS_006867) 28885802(PLICBS_007320)
PTKZ : JDV02_005429(ERG11_1) JDV02_007132(ERG11_2)
CFJ : CFIO01_02200 CFIO01_07699
CHIG : CH63R_00204 CH63R_00557
CDET : 87938903(CDEST_02400) 87939263(CDEST_02760)
ELA : UCREL1_2130 UCREL1_93
PFY : PFICI_01425 PFICI_03589
ANI : ANIA_01901 ANIA_08283
AFM : AFUA_4G06890 AFUA_7G03740
ACT : ACLA_005420 ACLA_046180
NFI : NFIA_024690 NFIA_109350
AOR : AO090003000205 AO090020000357 AO090026000842
ANG : An11g02230 An13g00090
AFV : AFLA_001488 AFLA_005443 AFLA_010303
ALUC : AKAW2_20184S(ERG11_1) AKAW2_80194S(ERG11_2)
ACHE : ACHE_40252S(ERG11_1) ACHE_70438A(ERG11_2)
APUU : APUU_21172A(ERG11_1) APUU_60531S(ERG11_2)
PCS : N7525_001490 N7525_009306
PDP : PDIP_01820 PDIP_80150
CIM : CIMG_00573 CIMG_07469
CPW : 9691916(ERG11_1) 9693625(ERG11_2)
URE : UREG_00593 UREG_07804
AJE : HCAG_04048 HCAG_04481
BGH : BDBG_01678 BDBG_04743
PTRR : 6346976(PtrM4_031460) 6347720(PtrM4_126540)
ADAC : 96088594(ACET3X_008272)
ZTR : MYCGRDRAFT_110231(CYP-74)
PFJ : MYCFIDRAFT_30715(CYP51)
CBET : CB0940_05116 CB0940_11379
NPA : UCRNP2_2683 UCRNP2_9069
CDEP : 91087568(L203_103357)
KMG : 30160494(I203_104372)
KNE : 92178707(IAR55_001448)
CCAC : CcaHIS019_0407180(ERG11)
DSQ : DICSQDRAFT_124779 DICSQDRAFT_147974
PCO : PHACADRAFT_132187 PHACADRAFT_214862
SHS : STEHIDRAFT_137057 STEHIDRAFT_59772
HIR : HETIRDRAFT_54612(cpm117)
ADL : AURDEDRAFT_112774 AURDEDRAFT_162003
CCI : CC1G_07605 CC1G_08364
ABP : AGABI1DRAFT114898(AGABI1DRAFT_114898)
ABV : AGABI2DRAFT191124(AGABI2DRAFT_191124)
PCUB : JR316_0005821 JR316_0009091 JR316_0010058
SCM : SCHCO_02627525(SCHCODRAFT_02627525)
CPUT : CONPUDRAFT_119932 CONPUDRAFT_155370
WSE : WALSEDRAFT_40560 WALSEDRAFT_59084
NGD : NGA_0373310(CYP51) NGA_0373320(CYP51)
TCR : 506297.260 510101.50
LMAT : 92516539(LSCM1_06615)
LOI : 92361909(LSCM4_06050)
LEIS : 94181965(GH5_06673)
LENR : 94174100(CUR178_06940)
LEIN : 94190368(JIQ42_06767)
PHET : 94293073(JKF63_07052)
NGR : NAEGRDRAFT_48319 NAEGRDRAFT_82952
MISZ : MishRS11D_35610(cyp51)
MBO : BQ2027_MB0787C(cyp51)
MMAE : MMARE11_47420(cyp51B1)
MSAK : MSAS_27680 MSAS_51760
MKU : I2456_00480 I2456_25125
MHEK : JMUB5695_00600(cyp51)
MHEV : MHEL_28850 MHEL_39460
MPAK : MIU77_02625 MIU77_05560
MJD : JDM601_3604(cyp51B1)
MTER : 4434518_03583(cyp51B1)
NSPU : IFM12276_41700(cyp51)
SRK : FGW37_00280 FGW37_00295
» show all
Taxonomy
Reference
1
Authors
Alexander K, Akhtar M, Boar RB, McGhie JF, Barton DHR.
Title
The removal of the 32-carbon atom as formic acid in cholesterol biosynthesis.
Journal
J Chem Soc Chem Commun 383-385 (1972)
Reference
Authors
Yoshida Y, Aoyama Y
Title
Yeast cytochrome P-450 catalyzing lanosterol 14 alpha-demethylation. I. Purification and spectral properties.
Journal
J Biol Chem 259:1655-60 (1984)
Reference
Authors
Aoyama Y, Yoshida Y, Sato R
Title
Yeast cytochrome P-450 catalyzing lanosterol 14 alpha-demethylation. II. Lanosterol metabolism by purified P-450(14)DM and by intact microsomes.
Journal
J Biol Chem 259:1661-6 (1984)
Reference
Authors
Aoyama Y, Yoshida Y
Title
Different substrate specificities of lanosterol 14a-demethylase (P-45014DM) of Saccharomyces cerevisiae and rat liver for 24-methylene-24,25-dihydrolanosterol and 24,25-dihydrolanosterol.
Journal
Reference
Authors
Aoyama Y, Yoshida Y.
Title
The 4 beta-methyl group of substrate does not affect the activity of lanosterol 14 alpha-demethylase (P-450(14)DM) of yeast: difference between the substrate recognition by yeast and plant sterol 14 alpha-demethylases.
Journal
Reference
Authors
Bak S, Kahn RA, Olsen CE, Halkier BA
Title
Cloning and expression in Escherichia coli of the obtusifoliol 14 alpha-demethylase of Sorghum bicolor (L.) Moench, a cytochrome P450 orthologous to the sterol 14 alpha-demethylases (CYP51) from fungi and mammals.
Journal
Sequence
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