Entry
Name
4alpha-methylsterol monooxygenase;
methylsterol hydroxylase (ambiguous);
4-methylsterol oxidase (ambiguous);
4,4-dimethyl-5alpha-cholest-7-en-3beta-ol,hydrogen-donor:oxygen oxidoreductase (hydroxylating) (ambiguous);
methylsterol monooxygenase (ambiguous);
ERG25 (gene name);
MSMO1 (gene name);
4,4-dimethyl-5alpha-cholest-7-en-3beta-ol,ferrocytochrome-b5:oxygen oxidoreductase (hydroxylating) (ambiguous)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With another compound 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,ferrocytochrome-b5:oxygen oxidoreductase (C4alpha-methyl-hydroxylating)
Reaction(IUBMB)
4,4-dimethyl-5alpha-cholest-7-en-3beta-ol + 6 ferrocytochrome b5 + 3 O2 + 6 H+ = 3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carboxylate + 6 ferricytochrome b5 + 4 H2O (overall reaction) [RN:
R10057 ];
(1a) 4,4-dimethyl-5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+ = 4alpha-hydroxymethyl-4beta-methyl-5alpha-cholest-7-en-3beta-ol + 2 ferricytochrome b5 + H2O [RN:
R04501 ];
(1b) 4alpha-hydroxymethyl-4beta-methyl-5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+ = 3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde + 2 ferricytochrome b5 + 2 H2O [RN:
R05733 ];
(1c) 3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde + 2 ferrocytochrome b5 + O2 + 2 H+ = 3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carboxylate + 2 ferricytochrome b5 + H2O [RN:
R05734 ]
Reaction(KEGG)
Substrate
4,4-dimethyl-5alpha-cholest-7-en-3beta-ol [CPD:
C04530 ];
ferrocytochrome b5 [CPD:
C00999 ];
O2 [CPD:
C00007 ];
H+ [CPD:
C00080 ];
4alpha-hydroxymethyl-4beta-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 ];
ferricytochrome b5 [CPD:
C00996 ];
H2O [CPD:
C00001 ];
4alpha-hydroxymethyl-4beta-methyl-5alpha-cholest-7-en-3beta-ol [CPD:
C04814 ];
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde [CPD:
C11509 ]
Comment
This enzyme is found in fungi and animals and catalyses a step in the biosynthesis of important sterol molecules such as ergosterol and cholesterol, respectively. The enzyme acts on the 4alpha-methyl group. Subsequent decarboxylation by EC
1.1.1.170 , 3beta-hydroxysteroid-4alpha-carboxylate 3-dehydrogenase (decarboxylating), occurs concomitantly with epimerization of the remaining 4beta-methyl into the 4alpha position, thus making it a suitable substrate for a second round of catalysis. cf. EC
1.14.13.246 , 4beta-methylsterol monooxygenase; EC
1.14.18.10 , plant 4,4-dimethylsterol C-4alpha-methyl-monooxygenase; and EC
1.14.18.11 , plant 4alpha-monomethylsterol monooxygenase.
History
EC 1.14.18.9 created 1972 as EC 1.14.99.16, transferred 2002 to EC 1.14.13.72, transferred 2017 to EC 1.14.18.9, modified 2019
Pathway
ec01110 Biosynthesis of secondary metabolites
Orthology
K07750 methylsterol monooxygenase
Genes
ANAN : 105732480 135277806
OGA : 100946570(MSMO1) 100963672
MORG : 121457492 121462767(Msmo1)
PLOP : 125339589(Msmo1) 125347930
MMMA : 107142728(Msmo1) 107158918
GVR : 103582356 103605034(MSMO1)
CFA : 102153215 102154725 119868057 475491(MSMO1)
CLUD : 112643069 112648519 112652817 112654312 112654747(MSMO1) 112675919
VLG : 121481576(MSMO1) 121481939 121483202 121485237 121501741
NPO : 129503990 129516870(MSMO1) 129521360
NVS : 122889554(MSMO1) 122898865
EJU : 114210190(MSMO1) 114211920
ZCA : 113910940 113925898(MSMO1) 118355980 118357008
MLX : 118002100 118022180(MSMO1)
LWW : 102730384(MSMO1) 102737494
OAS : 101121628(MSMO1) 105613287
BMUS : 118887134 118895981(MSMO1)
MMYO : 118658212(MSMO1) 118670801
AJM : 119045728(MSMO1) 119052871
PDIC : 114491483 114503548(MSMO1)
CPOO : 109309728(MSMO1) 109309860
CTIG : 120309829 120309830 120309831 120309832
PTEX : 113435853(MSMO1) 113454130
PMUA : 114604004 114604312
HCG : 128326167 128327940 128328559
XLA : 108704957(msmo1.L) 108706637(msmo1.S)
BGAR : 122940276 122940341
SANH : 107655978 107702386
CCAR : 109046545 109046546
CGIB : 127949372 127960217
PTET : 122347879 122347963
MASI : 127444343 127444499
OTW : 121844279(msmo1) 121844460
OGO : 124020867 124021427 124028478
CCLU : 121562770 121563070
AANG : 118226680 118228243
LERI : 129701761 129702910
BBEL : 109475810 109475811
SPU : 100891893 582397 587690
LPIC : 129257506 129274473 129274474 129274664
VPO : Kpol_414p6 Kpol_472p14
ZRO : ZYRO0B07172g ZYRO0B07744g
CGR : 2889999(GVI51_K04323)
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)
TGB : HG536_0E01240 HG536_0E01500
TDL : TDEL_0E01410(TDEL0E01410) TDEL_0E01680(TDEL0E01680)
KAF : KAFR_0F04030(KAFR0F04030) KAFR_0G03150(KAFR0G03150)
KNG : KNAG_0D04120(KNAG0D04120)
ZMK : HG535_0B06210 HG535_0F01540
DHA : DEHA2A12210g DEHA2G02640g
PIC : PICST_74706(ERG25) PICST_78360
PGU : PGUG_01908 PGUG_05253
SPAA : SPAPADRAFT_134612(SUR2.2) SPAPADRAFT_62633(ERG25)
LEL : PVL30_000073(ERG25_1) PVL30_003976(ERG25_3)
LBG : 92206212(LODBEIA_P10160)
CAL : CAALFM_C401530CA(ERG251) CAALFM_CR02370WA(ERG25)
CTP : CTRG_00198 CTRG_00908
COT : CORT_0A01460 CORT_0E01010
CDU : CD36_27330 CD36_41530
CTEN : 18246090(ERG25_2) 18249528(ERG25_1)
CLU : CLUG_00377 CLUG_02113
CLUS : A9F13_02g01804 A9F13_08g01859
PKZ : C5L36_0A11190 C5L36_0C08130
BNN : FOA43_001266(ERG25_1) FOA43_003536(ERG25_2)
BBRX : BRETT_002413(ERG25)
OPA : HPODL_02511 HPODL_05236
NTE : NEUTE1DRAFT116421(NEUTE1DRAFT_116421)
SMP : 10807572(SMAC4_00952)
PBEL : QC761_606020(ERG25)
PPSD : QC762_606020(ERG25)
PPSP : QC763_606020(ERG25)
PPSA : QC764_606020(ERG25)
PGRI : PgNI_00669 PgNI_01739
TATV : 25781946(TrAtP1_001391)
TASP : 36613259(TrAFT101_001105)
MAW : 19250716(J3458_002137)
PLJ : 28883007(PLICBS_000980)
PTKZ : JDV02_007785(ERG25)
CFJ : CFIO01_02681 CFIO01_07850
CLUP : CLUP02_09593 CLUP02_15014
CHIG : CH63R_03833 CH63R_04639 CH63R_13325
CDET : 87940865(CDEST_04362) 87941707(CDEST_05204) 87951555(CDEST_15055)
ANI : ANIA_06973 ANIA_08907
AFM : AFUA_4G04820 AFUA_8G02440
ACT : ACLA_043620 ACLA_067970
AOR : AO090010000667 AO090206000001
ALUC : AKAW2_40689A(ERG25) AKAW2_50990S
APUU : APUU_10643A(ERG25_1) APUU_21878S APUU_80630A(ERG25_3)
URE : UREG_02575 UREG_07066
PTRR : 6346723(PtrM4_147910)
ZTR : MYCGRDRAFT_36271(ERG25)
CDEP : 91084773(L203_100557)
KMG : 30166727(I203_106589)
KNE : 92178374(IAR55_001115)
CCAC : CcaHIS019_0701720(ERG25)
HIR : HETIRDRAFT_148092(smo1)
FME : FOMMEDRAFT_117464 FOMMEDRAFT_159067
LBC : LACBIDRAFT_182669(ERG25p-2)
ABP : AGABI1DRAFT115836(AGABI1DRAFT_115836)
ABV : AGABI2DRAFT228680(AGABI2DRAFT_228680)
SCM : SCHCO_02628730(SCHCODRAFT_02628730)
» show all
Taxonomy
Reference
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
Reference
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 243:4966-72 (1968)
Reference
Authors
Sharpless KB, Snyder TE, Spencer TA, Maheshwari KK, Nelson JA
Title
Biological demethylation of 4,4-dimethyl sterols, Evidence for enzymic epimerization of the 4beta-methyl group prior to its oxidative removal.
Journal
Reference
Authors
Brady DR, Crowder RD, Hayes WJ
Title
Mixed function oxidases in sterol metabolism. Source of reducing equivalents.
Journal
J Biol Chem 255:10624-9 (1980)
Reference
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 256:4822-6 (1981)
Reference
Authors
Kawata S, Trzaskos JM, Gaylor JL.
Title
Affinity chromatography of microsomal enzymes on immobilized detergent-solubilized cytochrome b5.
Journal
J Biol Chem 261:3790-9 (1986)
Other DBs
ExPASy - ENZYME nomenclature database: 1.14.18.9
LinkDB
All DBs