KEGG   ENZYME: 1.14.13.72Help
Entry
EC 1.14.13.72               Enzyme                                 

Name
methylsterol monooxygenase;
methylsterol hydroxylase;
4-methylsterol oxidase;
4,4-dimethyl-5alpha-cholest-7-en-3beta-ol,hydrogen-donor:oxygen oxidoreductase (hydroxylating)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
4,4-dimethyl-5alpha-cholest-7-en-3beta-ol,NAD(P)H:oxygen oxidoreductase (hydroxylating)
Reaction(IUBMB)
4,4-dimethyl-5alpha-cholest-7-en-3beta-ol + 3 NAD(P)H + 3 H+ + 3 O2 = 3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carboxylate + 3 NAD(P)+ + 4 H2O (overall reaction) [RN:R10057 R10058];
(1a) 4,4-dimethyl-5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 = 4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol + NAD(P)+ + H2O [RN:R04501 R05736];
(1b) 4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 = 3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde + NAD(P)+ + 2 H2O [RN:R05733 R05737];
(1c) 3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde + NAD(P)H + H+ + O2 = 3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carboxylate + NAD(P)+ + H2O [RN:R05734 R05738]
Reaction(KEGG)
Substrate
4,4-dimethyl-5alpha-cholest-7-en-3beta-ol [CPD:C04530];
NADH [CPD:C00004];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007];
4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol [CPD:C04814];
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde [CPD:C11509]
Product
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carboxylate [CPD:C04840];
NAD+ [CPD:C00003];
NADP+ [CPD:C00006];
H2O [CPD:C00001];
4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol [CPD:C04814];
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde [CPD:C11509]
Comment
Requires cytochrome b5. Also acts on 4alpha-methyl-5alpha-cholest-7-en-3beta-ol. The sterol can be based on cycloartenol as well as lanosterol.
History
EC 1.14.13.72 created 1972 as EC 1.14.99.16, transferred 2002 to EC 1.14.13.72
Pathway
Steroid biosynthesis
Metabolic pathways
Biosynthesis of secondary metabolites
Biosynthesis of antibiotics
Orthology
K07750  
methylsterol monooxygenase
K14423  
4,4-dimethyl-9beta,19-cyclopropylsterol-4alpha-methyl oxidase
K14424  
4-alpha-methyl-delta7-sterol-4alpha-methyl oxidase
Genes
HSA: 
10826(FAXDC2) 6307(MSMO1)
PTR: 
471796(FAXDC2) 738493(MSMO1)
PPS: 
100980614(FAXDC2) 100986460(MSMO1)
GGO: 
101135163(MSMO1) 101151077(C5H5orf4)
PON: 
100173838(MSMO1) 100455510(FAXDC2)
NLE: 
100580556(FAXDC2) 100603031(MSMO1)
MCC: 
705106(MSMO1) 714763(FAXDC2)
MCF: 
101865422(MSMO1) 102134726(FAXDC2)
RRO: 
104660243(FAXDC2) 104663423(MSMO1)
CJC: 
MMU: 
66234(Msmo1)
RNO: 
140910(Msmo1) 691221(Faxdc2)
CGE: 
100754784(Msmo1) 100767373(Faxdc2)
NGI: 
103732786(Msmo1) 103741517(Faxdc2)
HGL: 
101716533(Faxdc2) 101719361(Msmo1)
OCU: 
100343167(MSMO1) 100347389(FAXDC2)
TUP: 
102479705(FAXDC2) 102495765(MSMO1)
CFA: 
475491(MSMO1) 489163(FAXDC2)
AML: 
100473174(FAXDC2) 100478610(MSMO1)
UMR: 
103658127(MSMO1) 103664557(FAXDC2)
FCA: 
101083401(FAXDC2) 101096978(MSMO1)
PTG: 
102951249(FAXDC2) 102957399(MSMO1)
BTA: 
504481(MSMO1) 785044(FAXDC2)
BOM: 
102273126(FAXDC2) 102279364(MSMO1)
PHD: 
CHX: 
102176529(FAXDC2) 102180413(MSMO1)
OAS: 
101112818(FAXDC2) 101121628(MSMO1)
SSC: 
100525263(FAXDC2) 396590(MSMO1)
CFR: 
102515327(FAXDC2) 102519347(MSMO1)
BACU: 
103002999(MSMO1) 103006027(FAXDC2)
LVE: 
103075544(FAXDC2) 103089686(MSMO1)
ECB: 
100061552(MSMO1) 100147617(FAXDC2)
MYB: 
102246026(FAXDC2) 102263681(MSMO1)
MYD: 
102751432(FAXDC2) 102755773(MSMO1)
PALE: 
102896965(MSMO1) 102898896(FAXDC2)
MDO: 
100015712(MSMO1) 100029810(FAXDC2)
SHR: 
OAA: 
100075041(MSMO1) 100076382(FAXDC2)
GGA: 
416256(FAXDC2) 422423(MSMO1)
MGP: 
100545496(FAXDC2) 100550538(MSMO1)
CJO: 
107313018(MSMO1) 107320117(FAXDC2)
APLA: 
101803016(FAXDC2) 101804996(MSMO1)
TGU: 
100222623(MSMO1) 100229933(FAXDC2)
GFR: 
102035274(FAXDC2) 102040644(MSMO1)
FAB: 
101811763(MSMO1) 101818532(FAXDC2)
PHI: 
102102192(FAXDC2) 102111371(MSMO1)
CCW: 
104689554(FAXDC2) 104690530(MSMO1)
FPG: 
101914205(MSMO1) 101922167(FAXDC2)
FCH: 
102048602(FAXDC2) 102050992(MSMO1)
CLV: 
102086288(MSMO1) 102090762(FAXDC2)
AAM: 
106484071(MSMO1) 106493638(FAXDC2)
ASN: 
AMJ: 
PSS: 
102449794(MSMO1) 102451083(FAXDC2)
CMY: 
102930070(MSMO1) 102943333(FAXDC2)
ACS: 
100552150(msmo1) 100552534(faxdc2)
PBI: 
GJA: 
107115378(FAXDC2) 107116888(MSMO1)
XLA: 
734890(faxdc2)
XTR: 
100496051(faxdc2) 780270(msmo1)
DRE: 
406662(msmo1) 406828(faxdc2)
TRU: 
101070460(msmo1) 101078782(faxdc2)
MZE: 
101464632(faxdc2) 101479801(msmo1)
OLA: 
101170205(faxdc2) 105354476(msmo1)
XMA: 
102218750(faxdc2) 102232647(msmo1)
LCM: 
102348701(FAXDC2) 102357049(MSMO1)
CMK: 
103183717(msmo1) 103188208(faxdc2)
BFO: 
CIN: 
SPU: 
SKO: 
DME: 
DPO: 
DAN: 
DER: 
DPE: 
DSE: 
DSI: 
Dsimw501_GD15886(Dsim_GD15886) Dsimw501_GD17139(Dsim_GD17139)
DWI: 
DYA: 
Dyak_GE16159(dyak_GLEANR_17607)
DGR: 
DMO: 
DVI: 
MDE: 
AGA: 
AAG: 
CQU: 
AME: 
409360(GB16080) 727357
SOC: 
AEC: 
HST: 
CFO: 
NVI: 
TCA: 
PHU: 
ISC: 
CEL: 
CELE_F49E12.10(F49E12.10) CELE_F49E12.9(drd-1)
CBR: 
HRO: 
LGI: 
CRG: 
OBI: 
NVE: 
HMG: 
TAD: 
AQU: 
ATH: 
AT1G07420(SMO2-1) AT2G29390(SMO2-2) AT4G12110(SMO1-1) AT4G22753(SMO1-3) AT4G22756(SMO1-2)
ALY: 
CRB: 
EUS: 
BRP: 
BNA: 
THJ: 
CIT: 
CIC: 
TCC: 
GRA: 
EGR: 
GMX: 
PVU: 
VRA: 
MTR: 
CAM: 
ADU: 
AIP: 
FVE: 
PPER: 
PMUM: 
MDM: 
PXB: 
CSV: 
CMO: 
RCU: 
JCU: 
POP: 
POPTR_0001s08050g POPTR_0001s25210g(POPTRDRAFT_752102) POPTR_0003s11570g(POPTRDRAFT_854922) POPTR_0009s04220g(POPTRDRAFT_723203) POPTR_0014s06510g(POPTRDRAFT_244042)
VVI: 
SLY: 
SPEN: 
SOT: 
SIND: 
BVG: 
NNU: 
OSA: 
DOSA: 
Os03t0108500-01(Os03g0108500) Os07t0101500-01(Os07g0101500) Os10t0545200-01(Os10g0545200) Os11t0707600-01(Os11g0707600)
OBR: 
BDI: 
SBI: 
SORBI_01g030160(SORBIDRAFT_01g030160) SORBI_01g048370(SORBIDRAFT_01g048370) SORBI_03g021040(SORBIDRAFT_03g021040) SORBI_07g005830(SORBIDRAFT_07g005830)
ZMA: 
100217119(GRMZM2G062531) 100281761(GRMZM2G176301) 100282050 100282314(gpm532) 100285879(gpm829) 101027128 542766(gpm633)
SITA: 
PDA: 
EGU: 
MUS: 
ATR: 
SMO: 
PPP: 
OLU: 
OTA: 
MIS: 
CME: 
GSL: 
CCP: 
SCE: 
YGR060W(ERG25)
AGO: 
ERC: 
KLA: 
LTH: 
VPO: 
ZRO: 
CGR: 
NCS: 
NCAS_0A02240(NCAS0A02240) NCAS_0A02420(NCAS0A02420)
NDI: 
NDAI_0D04170(NDAI0D04170) NDAI_0D04450(NDAI0D04450)
TPF: 
TPHA_0B02330(TPHA0B02330) TPHA_0F01110(TPHA0F01110)
TBL: 
TBLA_0D02010(TBLA0D02010)
TDL: 
TDEL_0E01410(TDEL0E01410) TDEL_0E01680(TDEL0E01680)
KAF: 
KAFR_0F04030(KAFR0F04030) KAFR_0G03150(KAFR0G03150)
PPA: 
DHA: 
PIC: 
PGU: 
SPAA: 
LEL: 
CAL: 
CaO19.11216(ERG251) CaO19.3732(ERG251) CaO19.4631(ERG252)
CTP: 
COT: 
CDU: 
CTEN: 
YLI: 
CLU: 
NCR: 
NTE: 
NEUTE1DRAFT102694(NEUTE1DRAFT_102694) NEUTE1DRAFT116421(NEUTE1DRAFT_116421)
SMP: 
PAN: 
TTT: 
MTM: 
CTHR: 
MGR: 
TMN: 
FGR: 
FPU: 
NHE: 
TRE: 
MAW: 
MAJ: 
CMT: 
VAL: 
VDA: 
ELA: 
SSL: 
BFU: 
MBE: 
ANI: 
AFM: 
AOR: 
AOR_1_1114024(AO090010000667) AOR_1_348074 AOR_1_44(AO090206000001) AOR_1_514174(AO090005000286)
AFV: 
ACT: 
NFI: 
PCS: 
CIM: 
CPW: 
PBL: 
PBN: 
URE: 
ABE: 
TVE: 
AJE: 
PNO: 
PTE: 
BZE: 
BSC: 
BOR: 
ZTR: 
PFJ: 
BCOM: 
NPA: 
TML: 
SPO: 
CNE: 
CNB: 
CGI: 
TMS: 
DSQ: 
PCO: 
SHS: 
HIR: 
PSQ: 
ADL: 
FME: 
GTR: 
LBC: 
MPR: 
MRR: 
CCI: 
SCM: 
ABP: 
AGABI1DRAFT115836(AGABI1DRAFT_115836)
ABV: 
AGABI2DRAFT228680(AGABI2DRAFT_228680)
CPUT: 
SLA: 
WSE: 
WIC: 
UMA: 
PFP: 
MGL: 
PGR: 
MLR: 
MBR: 
SRE: 
DDI: 
DPP: 
DFA: 
ACAN: 
TET: 
PTM: 
AAF: 
SPAR: 
EHX: 
NGR: 
OAI: 
AGE: 
 » show all
Taxonomy
Reference
1  [PMID:9240456]
  Authors
Rahier A, Smith M, Taton M.
  Title
The role of cytochrome b5 in 4alpha-methyl-oxidation and C5(6) desaturation of plant sterol precursors.
  Journal
Biochem. Biophys. Res. Commun. 236 (1997) 434-7.
Reference
2  [PMID:8505296]
  Authors
Pascal S, Taton M, Rahier A.
  Title
Plant sterol biosynthesis. Identification and characterization of two distinct microsomal oxidative enzymatic systems involved in sterol C4-demethylation.
  Journal
J. Biol. Chem. 268 (1993) 11639-54.
Reference
3  [PMID:3949790]
  Authors
Kawata S, Trzaskos JM, Gaylor JL.
  Title
Affinity chromatography of microsomal enzymes on immobilized detergent-solubilized cytochrome b5.
  Journal
J. Biol. Chem. 261 (1986) 3790-9.
Reference
4  [PMID:7228857]
  Authors
Fukushima H, Grinstead GF, Gaylor JL.
  Title
Total enzymic synthesis of cholesterol from lanosterol. Cytochrome b5-dependence of 4-methyl sterol oxidase.
  Journal
J. Biol. Chem. 256 (1981) 4822-6.
Reference
5  [PMID:7430141]
  Authors
Brady DR, Crowder RD, Hayes WJ.
  Title
Mixed function oxidases in sterol metabolism. Source of reducing equivalents.
  Journal
J. Biol. Chem. 255 (1980) 10624-9.
Reference
6  [PMID:4234469]
  Authors
Gaylor JL, Mason HS.
  Title
Investigation of the component reactions of oxidative sterol demethylation. Evidence against participation of cytochrome P-450.
  Journal
J. Biol. Chem. 243 (1968) 4966-72.
Reference
7  [PMID:4383278]
  Authors
Miller WL, Kalafer ME, Gaylor JL, Delwiche CV.
  Title
Investigation of the component reactions of oxidative sterol demethylation. Study of the aerobic and anaerobic processes.
  Journal
Biochemistry. 6 (1967) 2673-8.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
CAS: 
37256-80-7

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