KEGG   ENZYME: 1.14.15.36
Entry
EC 1.14.15.36               Enzyme                                 

Name
sterol 14alpha-demethylase (ferredoxin);
cyp51 (gene name)
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
sterol,reduced ferredoxin:oxygen oxidoreductase (14-methyl cleaving)
Reaction(IUBMB)
a 14alpha-methylsteroid + 6 reduced ferredoxin [iron-sulfur] cluster + 6 H+ + 3 O2 = a Delta14-steroid + formate + 6 oxidized ferredoxin [iron-sulfur] cluster + 4 H2O (overall reaction) [RN:R12317];
(1a) a 14alpha-methylsteroid + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = a 14alpha-hydroxymethylsteroid + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O [RN:R12318];
(1b) a 14alpha-hydroxymethylsteroid + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = a 14alpha-formylsteroid + 2 oxidized ferredoxin [iron-sulfur] cluster + 2 H2O [RN:R12321];
(1c) a 14alpha-formylsteroid + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = a Delta14-steroid + formate + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O [RN:R12322]
Reaction(KEGG)
Substrate
14alpha-methylsteroid [CPD:C21918];
reduced ferredoxin [iron-sulfur] cluster [CPD:C00138];
H+ [CPD:C00080];
O2 [CPD:C00007];
14alpha-hydroxymethylsteroid [CPD:C21920];
14alpha-formylsteroid [CPD:C21921]
Product
Delta14-steroid [CPD:C21919];
formate [CPD:C00058];
oxidized ferredoxin [iron-sulfur] cluster [CPD:C00139];
H2O [CPD:C00001];
14alpha-hydroxymethylsteroid [CPD:C21920];
14alpha-formylsteroid [CPD:C21921]
Comment
A cytochrome P-450 (heme-thiolate) protein found in several bacterial species. The enzyme, which is involved in sterol biosynthesis, 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. The enzyme from Methylococcus capsulatus is fused to the ferredoxin by an alanine-rich linker. cf. EC 1.14.14.154, sterol 14alpha-demethylase.
History
EC 1.14.15.36 created 2019
Pathway
ec00100  Steroid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K05917  sterol 14alpha-demethylase
Genes
HSA: 1595(CYP51A1)
PTR: 463527(CYP51A1)
PPS: 100985833
GGO: 101127636
PON: 100171776(CYP51A1) 100456763
NLE: 100582853
MCC: 703490
MCF: 102146764(CYP51)
CSAB: 103226567(CYP51A1)
CATY: 105573073
PANU: 101018881
RRO: 104654375
RBB: 108544026
TFN: 117073642
PTEH: 111552471
CJC: 100403815(CYP51A1) 103792683
SBQ: 101036999
MMUR: 105879402
MMU: 13121(Cyp51)
MCAL: 110294823
MPAH: 110316208
RNO: 25427(Cyp51)
CGE: 100762189
PLEU: 114688078
NGI: 103725250
HGL: 101724157
CCAN: 109684681
OCU: 100355623
OPI: 101517639
TUP: 102493691
CFA: 475225(CYP51A1)
VVP: 112923882
VLG: 121475156
AML: 100477744
UMR: 103658707
UAH: 113259854
ORO: 101381709
ELK: 111147264
MPUF: 101671415
EJU: 114221218
MLX: 118020747
FCA: 101083499
PYU: 121028755
PBG: 122487867
PTG: 102954144
PPAD: 109263677
AJU: 106969977
HHV: 120224629
BTA: 505060(CYP51A1)
BOM: 102282237
BIU: 109558194
BBUB: 102410939
CHX: 102177400
OAS: 101113583
ODA: 120877853
CCAD: 122438080
SSC: 403334(CYP51)
CFR: 102515047
CBAI: 105072505
CDK: 105087385
BACU: 103016503
LVE: 103083607
OOR: 101275315
DLE: 111180826
PCAD: 102992983
ECB: 100050921
EPZ: 103549183
EAI: 106832249
MYB: 102261507
MYD: 102765294
MMYO: 118666242
MNA: 107541737
HAI: 109378118
DRO: 112319863
SHON: 119000956
AJM: 119042729
MMF: 118620048
PGIG: 120615039
RAY: 107519059
MJV: 108389928
TOD: 119241973
LAV: 100670599
TMU: 101349253
MDO: 100028071
SHR: 100916047
PCW: 110209164
OAA: 100087589
GGA: 420548(CYP51A1)
PCOC: 116243246
MGP: 100538580
CJO: 107309008
NMEL: 110393597
APLA: 101791330
TGU: 100220976
LSR: 110482429
SCAN: 103812812
PMOA: 120504063
OTC: 121338167
PRUF: 121353175
GFR: 102035109
FAB: 101818100
PHI: 102113235
PMAJ: 107199957
CCAE: 111924212
CCW: 104689183
ETL: 114062125
FPG: 101920327
FCH: 102048344
CLV: 102092834
EGZ: 104128884
NNI: 104014027
ACUN: 113477142
PADL: 103922388
AAM: 106483616
AROW: 112965897
NPD: 112947354
DNE: 112982314
ASN: 102386214
AMJ: 102567199(CYP51A1)
CPOO: 109308659
GGN: 109291397
PSS: 102445540
CMY: 102945327
CPIC: 101934931
TST: 117872199
CABI: 116835338
ACS: 100557431
PVT: 110074721
PBI: 103065003
PMUR: 107286842
TSR: 106538331
PGUT: 117655141
PMUA: 114607228
ZVI: 118092023
GJA: 107108228
XLA: 100037098(cyp51a1.L) 447600(cyp51a1.S)
XTR: 548948(cyp51a1)
NPR: 108787913
DRE: 414331(cyp51)
SRX: 107712294
SANH: 107694387
SGH: 107568024
CCAR: 109111832
IPU: 108274811
PHYP: 113525251
AMEX: 103025877
EEE: 113590695
TRU: 101062187
LCO: 104927570
NCC: 104962954
CGOB: 115015458
ELY: 117263271
PLEP: 121957574
SLUC: 116047367
ECRA: 117957116
PFLV: 114568257
GAT: 120826698
PPUG: 119219440
MSAM: 119907680
CUD: 121523306
MZE: 101487063
ONL: 100702293
OAU: 116320002
OLA: 101169834
OML: 112148369
XMA: 102232424
XCO: 114156093
XHE: 116731278
PRET: 103472487
CVG: 107102957
CTUL: 119779664
NFU: 107394621
KMR: 108238686
ALIM: 106518131
AOCE: 111565075
CSEM: 103394548
POV: 109648114
LCF: 108879466
SDU: 111222971
SLAL: 111657606
XGL: 120785950
HCQ: 109512012
BPEC: 110161131
MALB: 109958704
ELS: 105012654
SFM: 108933335
PKI: 111843959
AANG: 118215084
LOC: 102693705
PSPA: 121315018
LCM: 102347020
CMK: 103181227
RTP: 109915762
BFO: 118424043
BBEL: 109486589
SPU: 414330(cyp51)
APLC: 110975221
SKO: 100367489
PCAN: 112564918
BGT: 106072162
GAE: 121381676
OSN: 115229399
AQU: 100636481
ATH: AT1G11680(CYP51G1)
ALY: 9325951
THJ: 104807262
CPAP: 110809570
CIT: 102623201
TCC: 18608823
EGR: 104433736
GMX: 100810799
VRA: 106774110
VAR: 108347419
VUN: 114166877
CCAJ: 109788471
APRC: 113849840
CAM: 101504867
LJA: Lj3g3v0512940.1(Lj3g3v0512940.1)
ADU: 107473174
AIP: 107624804
FVE: 101305627(cyp51)
RCN: 112197377
PPER: 18790148
PMUM: 103322154
PAVI: 110768705
PDUL: 117625263
CSV: 101205062
CMO: 103494635
BHJ: 120073775
MCHA: 111015169
RCU: 8285703
JCU: 105647292
QLO: 115982020
SLY: 100736446(CYP51)
SPEN: 107003288
SOT: 102601151
CANN: 107838742
NTA: 107764727(CYP51) 107779000(NtCYP51-2)
NSY: 104231276
NTO: 104096055
NAU: 109244278
INI: 109176104
ITR: 116002000
HAN: 110920587
ECAD: 122578423
LSV: 111912345
DCR: 108228020
CSIN: 114261517
MING: 122061785
DOSA: Os02t0113200-00(Os02g0113200) Os02t0323600-01(Os02g0323600) Os05t0211100-01(Os05g0211100) Os05t0415800-01(Os05g0415800) Os05t0416400-00(Os05g0416400) Os07t0567100-00(Os07g0567100) Os11t0525200-01(Os11g0525200)
DCT: 110107398
PEQ: 110032189
AOF: 109827282
ATR: 18434309
PPP: 112285583
APRO: F751_0875
SCE: YHR007C(ERG11)
ERC: Ecym_6045
KMX: KLMA_20551(CYP707A7)
NCS: NCAS_0G00960(NCAS0G00960)
NDI: NDAI_0F01100(NDAI0F01100)
TPF: TPHA_0D02710(TPHA0D02710)
TBL: TBLA_0E02810(TBLA0E02810)
TDL: TDEL_0A04550(TDEL0A04550)
KAF: KAFR_0C05720(KAFR0C05720)
PIC: PICST_63421(CP51)
CAL: CAALFM_C500660CA(ERG11)
CDU: CD36_50660(ERG11)
SLB: AWJ20_2398(ERG11)
BNN: FOA43_001357(ERG11)
BBRX: BRETT_002515(ERG11)
NCR: NCU02624
NTE: NEUTE1DRAFT119039(NEUTE1DRAFT_119039)
SSCK: SPSK_09044
MAW: MAC_07103
MBE: MBM_02571
ANG: ANI_1_314094(An11g02230) ANI_1_518114(An13g00090)
ZTR: MYCGRDRAFT_110231(CYP-74)
PFJ: MYCFIDRAFT_30715(CYP51)
SPO: SPAC13A11.02c(erg11)
CNE: CNA00300
CNB: CNBA0300
TASA: A1Q1_02098
HIR: HETIRDRAFT_54612(cpm117)
ABP: AGABI1DRAFT114898(AGABI1DRAFT_114898)
ABV: AGABI2DRAFT191124(AGABI2DRAFT_191124)
MGL: MGL_2415
MRT: MRET_3233
DDI: DDB_G0279403(CYP51)
DFA: DFA_04411(CYP51)
SMIN: v1.2.021020.t1(symbB.v1.2.021020.t1)
NGD: NGA_0373310(CYP51) NGA_0373320(CYP51)
SPAR: SPRG_09493
MCA: MCA2711(cyp51)
MAH: MEALZ_0770(cyp)
MMAI: sS8_2580
MISZ: MishRS11D_35610(cyp51)
GPB: HDN1F_11100(cyp51)
NAR: Saro_3659
MTU: Rv0764c(cyp51)
MTC: MT0788
MRA: MRA_0773(cyp51)
MTUR: CFBS_0803(cyp51)
MTO: MTCTRI2_0783(cyp51)
MTN: ERDMAN_0846(cyp51)
MTUC: J113_05390
MTUE: J114_04080
MTUH: I917_05415
MTUL: TBHG_00756
MTUT: HKBT1_0803(cyp51)
MTUU: HKBT2_0804(cyp51)
MTQ: HKBS1_0803(cyp51)
MBO: BQ2027_MB0787C(cyp51)
MBB: BCG_0816c(cyp51)
MBT: JTY_0786(cyp51)
MBM: BCGMEX_0787c(cyp51)
MBX: BCGT_0565
MAF: MAF_07760(cyp51)
MMIC: RN08_0853
MCE: MCAN_07681(cyp51)
MCQ: BN44_10834(cyp)
MCV: BN43_20199(cyp)
MCX: BN42_20522(cyp)
MCZ: BN45_20033(cyp)
MPA: MAP_0598c
MAO: MAP4_3267
MAVI: RC58_16215
MAVU: RE97_16245
MAV: MAV_0708
MIA: OCU_06050
MID: MIP_01081
MYO: OEM_06100
MIR: OCQ_06160
MMAN: MMAN_49000
MUL: MUL_0473(cyp51B1)
MMC: Mmcs_4582
MKM: Mkms_4670
MJL: Mjls_4965
MMI: MMAR_4932(cyp51B1)
MMAE: MMARE11_47420(cyp51B1)
MMM: W7S_02950
MHAD: B586_05055
MSHG: MSG_04432
MSTO: MSTO_45820
MSIM: MSIM_30210
MXE: MYXE_06880(cyp51)
MNV: MNVI_11300(cyp51)
MCOO: MCOO_25730
MSEO: MSEO_33450
MSHO: MSHO_03830(cyp51)
MHEK: JMUB5695_00600(cyp51)
MLJ: MLAC_00920(cyp51)
MBRD: MBRA_21600(cyp51)
MSHJ: MSHI_39930(cyp51)
MKR: MKOR_36980(cyp51)
MSG: MSMEI_5704(cyp51)
MVA: Mvan_5161
MGI: Mflv_1596
MVQ: MYVA_5043
MHAS: MHAS_03647
MMAG: MMAD_47320
MMOR: MMOR_13190
MAIC: MAIC_06480
MALV: MALV_43560
MARZ: MARA_49270
MGAD: MGAD_36230
MSAR: MSAR_10030
MANY: MANY_32040
MAUB: MAUB_38880
MPOF: MPOR_52660
MPHU: MPHO_31220
MBOK: MBOE_20920
MAB: MAB_1214c
MABB: MASS_1212
MCHE: BB28_06025
MSTE: MSTE_01180
MJD: JDM601_3604(cyp51B1)
MTER: 4434518_03583(cyp51B1)
MMIN: MMIN_11340(cyp51)
MHIB: MHIB_30060(cyp51)
NFA: NFA_25890(cyp51)
NCY: NOCYR_4381(cyp)
NNO: NONO_c19250(cyp51)
RER: RER_33770(cyp51)
REY: O5Y_15560
ROP: ROP_47700(cyp51)
REQ: REQ_13820
GBR: Gbro_3843
GPO: GPOL_c37060(cyp)
GOR: KTR9_3783
PSIM: KR76_04945
SEN: SACE_3928(cyp51)
SESP: BN6_77630(cyp51)
 » show all
Reference
1  [PMID:12235134]
  Authors
Jackson CJ, Lamb DC, Marczylo TH, Warrilow AG, Manning NJ, Lowe DJ, Kelly DE, Kelly SL
  Title
A novel sterol 14alpha-demethylase/ferredoxin fusion protein (MCCYP51FX) from Methylococcus capsulatus represents a new class of the cytochrome P450 superfamily.
  Journal
J Biol Chem 277:46959-65 (2002)
DOI:10.1074/jbc.M203523200
Reference
2  [PMID:15383907]
  Authors
Rezen T, Debeljak N, Kordis D, Rozman D
  Title
New aspects on lanosterol 14alpha-demethylase and cytochrome P450 evolution: lanosterol/cycloartenol diversification and lateral transfer.
  Journal
J Mol Evol 59:51-8 (2004)
DOI:10.1007/s00239-004-2603-1
Reference
3  [PMID:20333205]
  Authors
Desmond E, Gribaldo S
  Title
Phylogenomics of sterol synthesis: insights into the origin, evolution, and diversity of a key eukaryotic feature.
  Journal
Genome Biol Evol 1:364-81 (2009)
DOI:10.1093/gbe/evp036
Other DBs
ExplorEnz - The Enzyme Database: 1.14.15.36
IUBMB Enzyme Nomenclature: 1.14.15.36
ExPASy - ENZYME nomenclature database: 1.14.15.36
BRENDA, the Enzyme Database: 1.14.15.36

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