KEGG   ENZYME: 1.14.14.154
Entry
EC 1.14.14.154              Enzyme                                 

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
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
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
RRO: 104654375
RBB: 108544026
TFN: 117073642
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
TUP: 102493691
CFA: 475225(CYP51A1)
VVP: 112923882
AML: 100477744
UMR: 103658707
UAH: 113259854
ORO: 101381709
ELK: 111147264
MPUF: 101671415
EJU: 114221218
FCA: 101083499
PTG: 102954144
PPAD: 109263677
AJU: 106969977
BTA: 505060(CYP51A1)
BOM: 102282237
BIU: 109558194
BBUB: 102410939
CHX: 102177400
OAS: 101113583
SSC: 403334(CYP51)
CFR: 102515047
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
RAY: 107519059
MJV: 108389928
LAV: 100670599
TMU: 101349253
MDO: 100028071
SHR: 100916047
PCW: 110209164
OAA: 100087589
GGA: 420548(CYP51A1)
MGP: 100538580
CJO: 107309008
NMEL: 110393597
APLA: 101791330
TGU: 100220976
LSR: 110482429
SCAN: 103812812
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
ASN: 102386214
AMJ: 102567199(CYP51A1)
PSS: 102445540
CMY: 102945327
CPIC: 101934931
ACS: 100557431
PVT: 110074721
PBI: 103065003
PMUR: 107286842
TSR: 106538331
PMUA: 114607228
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
MZE: 101487063
ONL: 100702293
OLA: 101169834
XMA: 102232424
XCO: 114156093
PRET: 103472487
CVG: 107102957
NFU: 107394621
KMR: 108238686
ALIM: 106518131
AOCE: 111565075
CSEM: 103394548
POV: 109648114
LCF: 108879466
SDU: 111222971
SLAL: 111657606
HCQ: 109512012
BPEC: 110161131
MALB: 109958704
ELS: 105012654
SFM: 108933335
PKI: 111843959
LCM: 102347020
CMK: 103181227
RTP: 109915762
BFO: 118424043
SPU: 414330(cyp51)
APLC: 110975221
SKO: 100367489
PCAN: 112564918
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
CAM: 101504867
LJA: Lj3g3v0512940.1(Lj3g3v0512940.1)
ADU: 107473174
AIP: 107624804
FVE: 101305627(cyp51)
RCN: 112197377
PPER: 18790148
PMUM: 103322154
PAVI: 110768705
CSV: 101205062
CMO: 103494635
MCHA: 111015169
RCU: 8285703
JCU: 105647292
SLY: 100736446(CYP51)
SPEN: 107003288
SOT: 102601151
CANN: 107838742
NTA: 107764727(CYP51) 107779000(NtCYP51-2)
NSY: 104231276
NTO: 104096055
NAU: 109244278
INI: 109176104
HAN: 110920587
LSV: 111912345
DCR: 108228020
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
CRE: CHLREDRAFT_196411(CYP51G1)
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
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
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
MXE: MYXE_06880(cyp51)
MNV: MNVI_11300(cyp51)
MCOO: MCOO_25730
MSEO: MSEO_33450
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
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)
MKR: MKOR_36980(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
  Authors
Alexander, K., Akhtar, M., Boar, R.B., McGhie, J.F. and Barton, D.H.R.
  Title
The removal of the 32-carbon atom as formic acid in cholesterol biosynthesis.
  Journal
J Chem Soc Chem Commun 383-385 (1972)
Reference
2  [PMID:6363414]
  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
3  [PMID:6420412]
  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
4  [PMID:1872829]
  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
Biochem Biophys Res Commun 178:1064-71 (1991)
DOI:10.1016/0006-291X(91)91000-3
Reference
5  [PMID:1567403]
  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
Biochem Biophys Res Commun 183:1266-72 (1992)
DOI:10.1016/S0006-291X(05)80327-4
Reference
6  [PMID:9076987]
  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
Plant J 11:191-201 (1997)
DOI:10.1046/j.1365-313X.1997.11020191.x
  Sequence
[sbi:8074834]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.154
IUBMB Enzyme Nomenclature: 1.14.14.154
ExPASy - ENZYME nomenclature database: 1.14.14.154
BRENDA, the Enzyme Database: 1.14.14.154
CAS: 60063-87-8

DBGET integrated database retrieval system