KEGG   ORTHOLOGY: K07750
Entry
K07750                      KO                                     

Name
MESO1, ERG25
Definition
methylsterol monooxygenase [EC:1.14.18.9]
Pathway
ko00100  Steroid biosynthesis
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
Module
M00101  Cholesterol biosynthesis, squalene 2,3-epoxide => cholesterol
M00102  Ergocalciferol biosynthesis, squalene 2,3-epoxide => ergosterol/ergocalciferol
Disease
H02132  Microcephaly syndrome
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09103 Lipid metabolism
   00100 Steroid biosynthesis
    K07750  MESO1, ERG25; methylsterol monooxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.18  With another compound as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.18.9  4alpha-methylsterol monooxygenase
     K07750  MESO1, ERG25; methylsterol monooxygenase
Other DBs
RN: R07509 R10057 R12403
COG: COG3000
GO: 0000254
Genes
HSA: 6307(MSMO1)
PTR: 738493(MSMO1)
PPS: 100986460(MSMO1)
GGO: 101135163(MSMO1)
PON: 100173838(MSMO1)
NLE: 100603031(MSMO1)
MCC: 705106(MSMO1)
MCF: 101865422(MSMO1)
CSAB: 103236486(MSMO1)
RRO: 104663423(MSMO1)
RBB: 108521935(MSMO1)
CJC: 100398666(MSMO1)
SBQ: 101053419(MSMO1)
MMU: 66234(Msmo1)
MCAL: 110300687(Msmo1)
MPAH: 110336636(Msmo1)
RNO: 140910(Msmo1)
MUN: 110549058(Msmo1)
CGE: 100754784(Msmo1)
NGI: 103732786(Msmo1)
HGL: 101719361(Msmo1)
CCAN: 109687904(Msmo1)
OCU: 100343167(MSMO1)
TUP: 102495765(MSMO1)
CFA: 475491(MSMO1)
VVP: 112916498
AML: 100478610(MSMO1)
UMR: 103658127(MSMO1)
UAH: 113255824(MSMO1)
ORO: 101384837(MSMO1)
ELK: 111154388
FCA: 101096978(MSMO1)
PTG: 102957399(MSMO1)
PPAD: 109262446(MSMO1)
AJU: 106967462(MSMO1)
BTA: 504481(MSMO1)
BOM: 102279364(MSMO1)
BIU: 109571212(MSMO1)
BBUB: 102414195(MSMO1)
CHX: 102180413(MSMO1)
OAS: 101121628(MSMO1)
SSC: 396590(MSMO1)
CFR: 102519347(MSMO1)
CDK: 105087398(MSMO1)
BACU: 103002999(MSMO1)
LVE: 103089686(MSMO1)
OOR: 101289371(MSMO1)
DLE: 111168093(MSMO1)
PCAD: 102973299(MSMO1)
ECB: 100061552(MSMO1)
EPZ: 103567419(MSMO1)
EAI: 106837736(MSMO1)
MYB: 102263681(MSMO1)
MYD: 102755773(MSMO1)
MNA: 107525574(MSMO1)
HAI: 109386939(MSMO1)
DRO: 112312647(MSMO1)
PALE: 102896965(MSMO1)
RAY: 107515609(MSMO1)
MJV: 108394573(MSMO1)
MDO: 100015712(MSMO1)
SHR: 100927294(MSMO1)
PCW: 110200933(MSMO1)
OAA: 100075041(MSMO1)
GGA: 422423(MSMO1)
MGP: 100550538(MSMO1)
CJO: 107313018(MSMO1)
NMEL: 110397908(MSMO1)
APLA: 101804996(MSMO1)
ACYG: 106032325(MSMO1)
TGU: 100222623(MSMO1)
LSR: 110481549(MSMO1)
SCAN: 103825935(MSMO1)
GFR: 102040644(MSMO1)
FAB: 101811763(MSMO1)
PHI: 102111371(MSMO1)
PMAJ: 107203507(MSMO1)
CCAE: 111927886(MSMO1)
CCW: 104690530(MSMO1)
ETL: 114057539(MSMO1)
FPG: 101914205(MSMO1)
FCH: 102050992(MSMO1)
CLV: 102086288(MSMO1)
EGZ: 104124048(MSMO1)
NNI: 104021256(MSMO1)
ACUN: 113479492(MSMO1)
AAM: 106484071(MSMO1)
ASN: 102373382(MSMO1)
AMJ: 102570191(MSMO1)
PSS: 102449794(MSMO1)
CMY: 102930070(MSMO1)
CPIC: 101942968(MSMO1)
ACS: 100552150(msmo1)
PVT: 110083492(MSMO1)
PBI: 103053887
PMUR: 107290875
TSR: 106550763(MSMO1)
GJA: 107116888(MSMO1)
XLA: 108704957(msmo1.L) 108706637(msmo1.S)
XTR: 780270(msmo1)
NPR: 108788887(MSMO1)
DRE: 406662(msmo1)
IPU: 100304913(msmo1)
PHYP: 113544334(msmo1)
AMEX: 103040405(msmo1)
EEE: 113591218(msmo1)
TRU: 101070460(msmo1)
LCO: 104933866(msmo1)
NCC: 104962899
MZE: 101479801(msmo1)
ONL: 100692996(msmo1)
OLA: 105354476(msmo1)
XMA: 102232647(msmo1)
XCO: 114144235(msmo1)
PRET: 103460529(msmo1)
CVG: 107090464(msmo1)
NFU: 107374119(msmo1)
KMR: 108248634(msmo1)
ALIM: 106525846(msmo1)
AOCE: 111574709(msmo1)
CSEM: 103384085(msmo1)
POV: 109638275(msmo1)
LCF: 108893083(msmo1)
SDU: 111216644(msmo1)
SLAL: 111657347(msmo1)
HCQ: 109511157(msmo1)
BPEC: 110167589(msmo1)
MALB: 109972109(msmo1)
SASA: 106590825(msmo1)
ELS: 105008532(msmo1)
SFM: 108924344(msmo1)
PKI: 111837277
LCM: 102357049(MSMO1)
CMK: 103183717(msmo1)
SPU: 582397
APLC: 110977365
SKO: 100377445
PCAN: 112556490
LAK: 106176186
AQU: 100640449
SCE: YGR060W(ERG25)
ERC: Ecym_6269
KMX: KLMA_50284(ERG25)
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)
SPAA: SPAPADRAFT_134612(SUR2.2) SPAPADRAFT_62633(ERG25)
CAL: CAALFM_C401530CA(ERG251) CAALFM_CR02370WA(ERG25)
CTEN: CANTEDRAFT_109226(ERG25) CANTEDRAFT_131473(SUR2.2)
SLB: AWJ20_3517(ERG25)
NCR: NCU06402
NTE: NEUTE1DRAFT116421(NEUTE1DRAFT_116421)
SSCK: SPSK_03491
MAW: MAC_06405
MAJ: MAA_05070
CMT: CCM_04265
MBE: MBM_00630
ANG: ANI_1_798034(An03g06410)
PTE: PTT_16124
ZTR: MYCGRDRAFT_36271(ERG25)
SPO: SPAC630.08c(erg25)
CNE: CNC02410
CNB: CNBC4830
TASA: A1Q1_00651
HIR: HETIRDRAFT_148092(smo1)
LBC: LACBIDRAFT_182669(ERG25p-2)
ABP: AGABI1DRAFT115836(AGABI1DRAFT_115836)
ABV: AGABI2DRAFT228680(AGABI2DRAFT_228680)
MRT: MRET_0062
DFA: DFA_04635
SPAR: SPRG_01623
 » show all
Reference
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 256:4822-6 (1981)
Reference
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 268:11639-54 (1993)
Reference
PMID:8552601
  Authors
Bard M, Bruner DA, Pierson CA, Lees ND, Biermann B, Frye L, Koegel C, Barbuch R
  Title
Cloning and characterization of ERG25, the Saccharomyces cerevisiae gene encoding C-4 sterol methyl oxidase.
  Journal
Proc Natl Acad Sci U S A 93:186-90 (1996)
DOI:10.1073/pnas.93.1.186
Reference
PMID:8663358
  Authors
Li L, Kaplan J
  Title
Characterization of yeast methyl sterol oxidase (ERG25) and identification of a human homologue.
  Journal
J Biol Chem 271:16927-33 (1996)
DOI:10.1074/jbc.271.28.16927
  Sequence
[hsa:6307] [sce:YGR060W]

KEGG   ENZYME: 1.14.18.9
Entry
EC 1.14.18.9                Enzyme                                 

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
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
ec00100  Steroid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K07750  methylsterol monooxygenase
Genes
HSA: 6307(MSMO1)
PTR: 738493(MSMO1)
PPS: 100986460(MSMO1)
GGO: 101135163(MSMO1)
PON: 100173838(MSMO1)
NLE: 100603031(MSMO1)
MCC: 705106(MSMO1)
MCF: 101865422(MSMO1)
CSAB: 103236486(MSMO1)
RRO: 104663423(MSMO1)
RBB: 108521935(MSMO1)
CJC: 100398666(MSMO1)
SBQ: 101053419(MSMO1)
MMU: 66234(Msmo1)
MCAL: 110300687(Msmo1)
MPAH: 110336636(Msmo1)
RNO: 140910(Msmo1)
MUN: 110549058(Msmo1)
CGE: 100754784(Msmo1)
NGI: 103732786(Msmo1)
HGL: 101719361(Msmo1)
CCAN: 109687904(Msmo1)
OCU: 100343167(MSMO1)
TUP: 102495765(MSMO1)
CFA: 475491(MSMO1)
VVP: 112916498
AML: 100478610(MSMO1)
UMR: 103658127(MSMO1)
UAH: 113255824(MSMO1)
ORO: 101384837(MSMO1)
ELK: 111154388
FCA: 101096978(MSMO1)
PTG: 102957399(MSMO1)
PPAD: 109262446(MSMO1)
AJU: 106967462(MSMO1)
BTA: 504481(MSMO1)
BOM: 102279364(MSMO1)
BIU: 109571212(MSMO1)
BBUB: 102414195(MSMO1)
CHX: 102180413(MSMO1)
OAS: 101121628(MSMO1)
SSC: 396590(MSMO1)
CFR: 102519347(MSMO1)
CDK: 105087398(MSMO1)
BACU: 103002999(MSMO1)
LVE: 103089686(MSMO1)
OOR: 101289371(MSMO1)
DLE: 111168093(MSMO1)
PCAD: 102973299(MSMO1)
ECB: 100061552(MSMO1)
EPZ: 103567419(MSMO1)
EAI: 106837736(MSMO1)
MYB: 102263681(MSMO1)
MYD: 102755773(MSMO1)
MNA: 107525574(MSMO1)
HAI: 109386939(MSMO1)
DRO: 112312647(MSMO1)
PALE: 102896965(MSMO1)
RAY: 107515609(MSMO1)
MJV: 108394573(MSMO1)
MDO: 100015712(MSMO1)
SHR: 100927294(MSMO1)
PCW: 110200933(MSMO1)
OAA: 100075041(MSMO1)
GGA: 422423(MSMO1)
MGP: 100550538(MSMO1)
CJO: 107313018(MSMO1)
NMEL: 110397908(MSMO1)
APLA: 101804996(MSMO1)
ACYG: 106032325(MSMO1)
TGU: 100222623(MSMO1)
LSR: 110481549(MSMO1)
SCAN: 103825935(MSMO1)
GFR: 102040644(MSMO1)
FAB: 101811763(MSMO1)
PHI: 102111371(MSMO1)
PMAJ: 107203507(MSMO1)
CCAE: 111927886(MSMO1)
CCW: 104690530(MSMO1)
ETL: 114057539(MSMO1)
FPG: 101914205(MSMO1)
FCH: 102050992(MSMO1)
CLV: 102086288(MSMO1)
EGZ: 104124048(MSMO1)
NNI: 104021256(MSMO1)
ACUN: 113479492(MSMO1)
AAM: 106484071(MSMO1)
ASN: 102373382(MSMO1)
AMJ: 102570191(MSMO1)
PSS: 102449794(MSMO1)
CMY: 102930070(MSMO1)
CPIC: 101942968(MSMO1)
ACS: 100552150(msmo1)
PVT: 110083492(MSMO1)
PBI: 103053887
PMUR: 107290875
TSR: 106550763(MSMO1)
GJA: 107116888(MSMO1)
XLA: 108704957(msmo1.L) 108706637(msmo1.S)
XTR: 780270(msmo1)
NPR: 108788887(MSMO1)
DRE: 406662(msmo1)
IPU: 100304913(msmo1)
PHYP: 113544334(msmo1)
AMEX: 103040405(msmo1)
EEE: 113591218(msmo1)
TRU: 101070460(msmo1)
LCO: 104933866(msmo1)
NCC: 104962899
MZE: 101479801(msmo1)
ONL: 100692996(msmo1)
OLA: 105354476(msmo1)
XMA: 102232647(msmo1)
XCO: 114144235(msmo1)
PRET: 103460529(msmo1)
CVG: 107090464(msmo1)
NFU: 107374119(msmo1)
KMR: 108248634(msmo1)
ALIM: 106525846(msmo1)
AOCE: 111574709(msmo1)
CSEM: 103384085(msmo1)
POV: 109638275(msmo1)
LCF: 108893083(msmo1)
SDU: 111216644(msmo1)
SLAL: 111657347(msmo1)
HCQ: 109511157(msmo1)
BPEC: 110167589(msmo1)
MALB: 109972109(msmo1)
SASA: 106590825(msmo1)
ELS: 105008532(msmo1)
SFM: 108924344(msmo1)
PKI: 111837277
LCM: 102357049(MSMO1)
CMK: 103183717(msmo1)
SPU: 582397
APLC: 110977365
SKO: 100377445
PCAN: 112556490
LAK: 106176186
AQU: 100640449
SCE: YGR060W(ERG25)
ERC: Ecym_6269
KMX: KLMA_50284(ERG25)
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)
SPAA: SPAPADRAFT_134612(SUR2.2) SPAPADRAFT_62633(ERG25)
CAL: CAALFM_C401530CA(ERG251) CAALFM_CR02370WA(ERG25)
CTEN: CANTEDRAFT_109226(ERG25) CANTEDRAFT_131473(SUR2.2)
SLB: AWJ20_3517(ERG25)
NCR: NCU06402
NTE: NEUTE1DRAFT116421(NEUTE1DRAFT_116421)
SSCK: SPSK_03491
MAW: MAC_06405
MAJ: MAA_05070
CMT: CCM_04265
MBE: MBM_00630
ANG: ANI_1_798034(An03g06410)
PTE: PTT_16124
ZTR: MYCGRDRAFT_36271(ERG25)
SPO: SPAC630.08c(erg25)
CNE: CNC02410
CNB: CNBC4830
TASA: A1Q1_00651
HIR: HETIRDRAFT_148092(smo1)
LBC: LACBIDRAFT_182669(ERG25p-2)
ABP: AGABI1DRAFT115836(AGABI1DRAFT_115836)
ABV: AGABI2DRAFT228680(AGABI2DRAFT_228680)
MRT: MRET_0062
DFA: DFA_04635
SPAR: SPRG_01623
 » show all
Reference
1  [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 6:2673-8 (1967)
DOI:10.1021/bi00861a005
Reference
2  [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 243:4966-72 (1968)
Reference
3  [PMID:5791927]
  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
J Am Chem Soc 91:3394-6 (1969)
DOI:10.1021/ja01040a065
Reference
4  [PMID:7430141]
  Authors
Brady DR, Crowder RD, Hayes WJ.
  Title
Mixed function oxidases in sterol metabolism. Source of reducing equivalents.
  Journal
J Biol Chem 255:10624-9 (1980)
Reference
5  [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 256:4822-6 (1981)
Reference
6  [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 261:3790-9 (1986)
Other DBs
ExplorEnz - The Enzyme Database: 1.14.18.9
IUBMB Enzyme Nomenclature: 1.14.18.9
ExPASy - ENZYME nomenclature database: 1.14.18.9
BRENDA, the Enzyme Database: 1.14.18.9
CAS: 37256-80-7

KEGG   REACTION: R07509
Entry
R07509                      Reaction                               

Name
14-demethyllanosterol,ferrocytochrome-b5:oxygen oxidoreductase (hydroxylating)
Definition
14-Demethyllanosterol + 6 Ferrocytochrome b5 + 3 Oxygen + 6 H+ <=> 4alpha-Methylzymosterol-4-carboxylate + 6 Ferricytochrome b5 + 4 H2O
Equation
C05108 + 6 C00999 + 3 C00007 + 6 C00080 <=> C15808 + 6 C00996 + 4 C00001
Reaction class
RC00001  C00005_C00006
RC01952  C05108_C15808
Enzyme
Pathway
rn00100  Steroid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00101  Cholesterol biosynthesis, squalene 2,3-epoxide => cholesterol
M00102  Ergocalciferol biosynthesis, squalene 2,3-epoxide => ergosterol/ergocalciferol
Orthology
K07750  methylsterol monooxygenase [EC:1.14.18.9]

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