KEGG   ORTHOLOGY: K14424
Entry
K14424                      KO                                     
Symbol
SMO2
Name
plant 4alpha-monomethylsterol monooxygenase [EC:1.14.18.11]
Pathway
map00100  Steroid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00917  Phytosterol biosynthesis, squalene 2,3-epoxide => campesterol/sitosterol
Reaction
R12378  24-methylenelophenol,ferrocytochrome-b5:oxygen oxidoreductase (C-4alpha-methyl-hydroxylating)
R12379  24-ethylidenelophenol,ferrocytochrome-b5:oxygen oxidoreductase (C-4alpha-methyl-hydroxylating)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09103 Lipid metabolism
   00100 Steroid biosynthesis
    K14424  SMO2; plant 4alpha-monomethylsterol 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
    1.14.18.11  plant 4alpha-monomethylsterol monooxygenase
     K14424  SMO2; plant 4alpha-monomethylsterol monooxygenase
Genes
BCOO: 119075284
CCIN: 107273060
OTU: 111419873
PRAP: 110998831
OFU: 114362392
DCI: 103512287 103512289
ATH: AT1G07420(SMO2-1) AT2G29390(SMO2-2)
ALY: 9315281 9325711
CRB: 17887780 17900058
CSAT: 104700565 104739310 104749943 104754908 104778598 104786746
EUS: EUTSA_v10008485mg EUTSA_v10017113mg
BRP: 103836444 103843947 103864965
BNA: 106362242 106391117 106402219 106420038 106450049 106450054 111208485
BOE: 106307917 106310476 106336604 106344016
RSZ: 108813689 108819536 108848436 108859993 130506284 130509714
THJ: 104815774 104826306
CPAP: 110812189
CIT: 102611328
CIC: CICLE_v10029052mg
PVY: 116144931
MINC: 123208340 123224689
TCC: 18590619
GRA: 105782837 105788785
GHI: 107934820 107944828 107950248 107950322
GAB: 108480542 108486460
HSYR: 120142165 120143299 120160068 120162099 120199310
DZI: 111302145 111303661
EGR: 104422462
RARG: 115736566
GMX: 100790183 100816716
GSJ: 114379876 114410260
PVU: 137810658 137810662
VRA: 106755866 106776423
VAR: 108323132 108323139
VUN: 114170147 114173059
VUM: 124827607 124843154
CCAJ: 109801255 109801590
APRC: 113868623 113868923
MTR: 11407532 11410003 120575921 25496266
TPRA: 123895575 123898285 123906764
CAM: 101502074 101515062
PSAT: 127119377
VVO: 131651052
LJA: 130739962 130739964
ADU: 107481295 107488889
AIP: 107631446 107643518
AHF: 112733956 112750064 112791831 112801082
LANG: 109330605 109331516 109332428
PCIN: 129313697 129315857
QSA: O6P43_000166 O6P43_028181
FVE: 101303960
AANS: 126787754
RCN: 112201412
PPER: 18773152
PMUM: 103321848
PAVI: 110773473
PDUL: 117630888
MDM: 103423556 103447498
MSYL: 126591318 126616813
PXB: 103954259 103964715
PCOX: 137715865 137742441
ZJU: 107410870
MNT: 21408018
CSAV: 115719554
CSV: 101220009 116403756
CMO: 103497129
BHJ: 120082510
MCHA: 111024686
CMAX: 111469499 111492998
CMOS: 111452253 111464703
CPEP: 111782737 111784635 111785325 111786943 111787435
RCU: 8284099
MEAN: 126688239
HBR: 110636927 110636928 110644392
MESC: 110606641 110619585
POP: 7481517 7485682
PEU: 105131124 105133116
PALZ: 118033002 118058014
PNZ: 133680349 133685824
JRE: 108995763 108998492
CILL: 122292564 122295090
CAVE: 132164527
AGLU: 133876968
QSU: 112022554
QLO: 115985585
TWL: 119990517 120015759
VVI: 100242817 100260328
VRI: 117916804 117927889 117932035
SLY: 100736533 101258266(SMO4)
SPEN: 107023487 107023820
SOT: 102589817 102602168
SSTN: 125872604 125872754
SDUL: 129898773 129900827
CANN: 107873488 107875519
LBB: 132605843
NTA: 107784901 107791166 107795609 107803664
NSY: 104232522 104249758
NTO: 104108313 104113382
NAU: 109214178 109227039
INI: 109156240 109157995 109166491
ITR: 116017168 116024961
SIND: 105170642
OEU: 111369663 111374734
EGT: 105957176
SSPL: 121742063 121743358
SMIL: 130991982 131006789
SHIS: 125214484
APAN: 127244331
HPUM: 140892802
PHUA: 140979481 140981431
PEBU: 140830938 140834023
HAN: 110868287 110873890
ECAD: 122581549 122607629
LSV: 111907260 111907489
CCAV: 112512724 112518020
DCR: 108206447 108206900
CSIN: 114274145 114286899
RVL: 131314156 131316746
AEW: 130761028 130790545
DLT: 127798157 127808822
BVG: 104900049
SOE: 110787672
CQI: 110683366 110688354
ATRI: 130814075
SLAF: 141590847 141617048 141622920 141634325
MOF: 131147618
NNU: 104597106 104601110
MING: 122058151 122073165
TSS: 122651833 122671597
PSOM: 113298854 113313160
OSA: 4342171 4351226
DOSA: Os07g0101500 Os11g0707600
OBR: 102706395 102708758
OGL: 127755528 127779539
BDI: 100835573
ATS: 109757775
TDC: 119286129 119295701
TAES: 123086313 123091749 123096733
TUA: 125551160
LPER: 127294651
LRD: 124703173
SBI: 8061435
ZMA: 100281761 542766
MFLO: 136449871 136508718 136535752 136540708
SITA: 101758336 101761504
SVS: 117856747 117866461
PVIR: 120645322 120673040 120685455 120707392
PHAI: 112895638 112903000
PAUA: 133886571 133900767
TANG: 140761756 140765494 140776032
PDA: 103697377 103715683 103716756
EGU: 105044346 105046366 105052184 105056895
MUS: 103969297 135613426 135616988 135622424
ZOF: 122013056 122015262 122042988 122047500
DCT: 110099264
PEQ: 110021891
AOF: 109822179 109848520
MSIN: 131243823 131252805
ACAK: 137941994 137965793
NCOL: 116256758
ATR: 18436262
CJF: 131054653
SMO: SELMODRAFT_151304 SELMODRAFT_173304 SELMODRAFT_231600 SELMODRAFT_233175
PPP: 112285210 112288272
CME: CYME_CMM277C
GSL: Gasu_60480
CCP: CHC_T00010320001
DDI: DDB_G0279611
DPP: DICPUDRAFT_28679 DICPUDRAFT_42415 DICPUDRAFT_76018 DICPUDRAFT_80876
DFA: DFA_11723
ACAN: ACA1_360510
NGR: NAEGRDRAFT_61038
PSYC: DABAL43B_2672
SOK: D0B54_23595
AGE: AA314_00718
AVM: JQX13_12580
MBD: MEBOL_003525
CFUS: CYFUS_000150
 » show all
Reference
PMID:11707264
  Authors
Darnet S, Bard M, Rahier A
  Title
Functional identification of sterol-4alpha-methyl oxidase cDNAs from Arabidopsis thaliana by complementation of a yeast erg25 mutant lacking sterol-4alpha-methyl oxidation.
  Journal
FEBS Lett 508:39-43 (2001)
DOI:10.1016/S0014-5793(01)03002-2
  Sequence
[ath:AT1G07420 AT2G29390]
Reference
PMID:21147141
  Authors
Rahier A
  Title
Dissecting the sterol C-4 demethylation process in higher plants. From structures and genes to catalytic mechanism.
  Journal
Steroids 76:340-52 (2011)
DOI:10.1016/j.steroids.2010.11.011
LinkDB

KEGG   ENZYME: 1.14.18.11
Entry
EC 1.14.18.11               Enzyme                                 
Name
plant 4alpha-monomethylsterol monooxygenase;
SMO2 (gene name)
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
24-ethylidenelophenol,ferrocytochrome-b5:oxygen oxidoreductase (C-4alpha-methyl-hydroxylating)
Reaction(IUBMB)
24-methylidenelophenol + 6 ferrocytochrome b5 + 3 O2 + 6 H+ = 3beta-hydroxyergosta-7,24(241)-dien-4alpha-carboxylate + 6 ferricytochrome b5 + 4 H2O (overall reaction) [RN:R12378];
(1a) 24-methylidenelophenol + 2 ferrocytochrome b5 + O2 + 2 H+ = 4alpha-(hydroxymethyl)ergosta-7,24(241)-dien-3beta-ol + 2 ferricytochrome b5 + H2O [RN:R12372];
(1b) 4alpha-(hydroxymethyl)ergosta-7,24(241)-dien-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+ = 4alpha-formylergosta-7,24(241)-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O [RN:R12373];
(1c) 4alpha-formylergosta-7,24(241)-dien-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+ = 3beta-hydroxyergosta-7,24(241)-dien-4alpha-carboxylate + 2 ferricytochrome b5 + H2O [RN:R12374]
Reaction(KEGG)
R12372 R12373 R12374 R12378;
(other) R12379
Substrate
24-methylidenelophenol [CPD:C11522];
ferrocytochrome b5 [CPD:C00999];
O2 [CPD:C00007];
H+ [CPD:C00080];
4alpha-(hydroxymethyl)ergosta-7,24(241)-dien-3beta-ol;
4alpha-formylergosta-7,24(241)-dien-3beta-ol
Product
3beta-hydroxyergosta-7,24(241)-dien-4alpha-carboxylate;
ferricytochrome b5 [CPD:C00996];
H2O [CPD:C00001];
4alpha-(hydroxymethyl)ergosta-7,24(241)-dien-3beta-ol;
4alpha-formylergosta-7,24(241)-dien-3beta-ol
Comment
This plant enzyme catalyses a step in the biosynthesis of sterols. It acts on the methyl group of the 4alpha-methylated intermediates 24-ethylidenelophenol and 24-methylidenelophenol and catalyses three successive oxidations, turning it into a carboxyl group. The carboxylate is subsequently removed by EC 1.1.1.418, plant 3beta-hydroxysteroid-4alpha-carboxylate 3-dehydrogenase (decarboxylating). Unlike the fungal/animal enzyme EC 1.14.18.9, 4alpha-methylsterol monooxygenase, this enzyme is not able to act on 4,4-dimethylated substrates. That activity, which occurs earlier in the pathway, is performed in plants by a second enzyme, EC 1.14.18.10, plant 4,4-dimethylsterol C-4alpha-methyl-monooxygenase.
History
EC 1.14.18.11 created 2019
Pathway
ec00100  Steroid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K14424  plant 4alpha-monomethylsterol monooxygenase
Genes
BCOO: 119075284
CCIN: 107273060
OTU: 111419873
PRAP: 110998831
OFU: 114362392
DCI: 103512287 103512289
ATH: AT1G07420(SMO2-1) AT2G29390(SMO2-2)
ALY: 9315281 9325711
CRB: 17887780 17900058
CSAT: 104700565 104739310 104749943 104754908 104778598 104786746
EUS: EUTSA_v10008485mg EUTSA_v10017113mg
BRP: 103836444 103843947 103864965
BNA: 106362242 106391117 106402219 106420038 106450049 106450054 111208485
BOE: 106307917 106310476 106336604 106344016
RSZ: 108813689 108819536 108848436 108859993 130506284 130509714
THJ: 104815774 104826306
CPAP: 110812189
CIT: 102611328
CIC: CICLE_v10029052mg
PVY: 116144931
MINC: 123208340 123224689
TCC: 18590619
GRA: 105782837 105788785
GHI: 107934820 107944828 107950248 107950322
GAB: 108480542 108486460
HSYR: 120142165 120143299 120160068 120162099 120199310
DZI: 111302145 111303661
EGR: 104422462
RARG: 115736566
GMX: 100790183 100816716
GSJ: 114379876 114410260
PVU: 137810658 137810662
VRA: 106755866 106776423
VAR: 108323132 108323139
VUN: 114170147 114173059
VUM: 124827607 124843154
CCAJ: 109801255 109801590
APRC: 113868623 113868923
MTR: 11407532 11410003 120575921 25496266
TPRA: 123895575 123898285 123906764
CAM: 101502074 101515062
PSAT: 127119377
VVO: 131651052
LJA: 130739962 130739964
ADU: 107481295 107488889
AIP: 107631446 107643518
AHF: 112733956 112750064 112791831 112801082
LANG: 109330605 109331516 109332428
PCIN: 129313697 129315857
QSA: O6P43_000166 O6P43_028181
FVE: 101303960
AANS: 126787754
RCN: 112201412
PPER: 18773152
PMUM: 103321848
PAVI: 110773473
PDUL: 117630888
MDM: 103423556 103447498
MSYL: 126591318 126616813
PXB: 103954259 103964715
PCOX: 137715865 137742441
ZJU: 107410870
MNT: 21408018
CSAV: 115719554
CSV: 101220009 116403756
CMO: 103497129
BHJ: 120082510
MCHA: 111024686
CMAX: 111469499 111492998
CMOS: 111452253 111464703
CPEP: 111782737 111784635 111785325 111786943 111787435
RCU: 8284099
MEAN: 126688239
HBR: 110636927 110636928 110644392
MESC: 110606641 110619585
POP: 7481517 7485682
PEU: 105131124 105133116
PALZ: 118033002 118058014
PNZ: 133680349 133685824
JRE: 108995763 108998492
CILL: 122292564 122295090
CAVE: 132164527
AGLU: 133876968
QSU: 112022554
QLO: 115985585
TWL: 119990517 120015759
VVI: 100242817 100260328
VRI: 117916804 117927889 117932035
SLY: 100736533 101258266(SMO4)
SPEN: 107023487 107023820
SOT: 102589817 102602168
SSTN: 125872604 125872754
SDUL: 129898773 129900827
CANN: 107873488 107875519
LBB: 132605843
NTA: 107784901 107791166 107795609 107803664
NSY: 104232522 104249758
NTO: 104108313 104113382
NAU: 109214178 109227039
INI: 109156240 109157995 109166491
ITR: 116017168 116024961
SIND: 105170642
OEU: 111369663 111374734
EGT: 105957176
SSPL: 121742063 121743358
SMIL: 130991982 131006789
SHIS: 125214484
APAN: 127244331
HPUM: 140892802
PHUA: 140979481 140981431
PEBU: 140830938 140834023
HAN: 110868287 110873890
ECAD: 122581549 122607629
LSV: 111907260 111907489
CCAV: 112512724 112518020
DCR: 108206447 108206900
CSIN: 114274145 114286899
RVL: 131314156 131316746
AEW: 130761028 130790545
DLT: 127798157 127808822
BVG: 104900049
SOE: 110787672
CQI: 110683366 110688354
ATRI: 130814075
SLAF: 141590847 141617048 141622920 141634325
MOF: 131147618
NNU: 104597106 104601110
MING: 122058151 122073165
TSS: 122651833 122671597
PSOM: 113298854 113313160
OSA: 4342171 4351226
DOSA: Os07g0101500 Os11g0707600
OBR: 102706395 102708758
OGL: 127755528 127779539
BDI: 100835573
ATS: 109757775
TDC: 119286129 119295701
TAES: 123086313 123091749 123096733
TUA: 125551160
LPER: 127294651
LRD: 124703173
SBI: 8061435
ZMA: 100281761 542766
MFLO: 136449871 136508718 136535752 136540708
SITA: 101758336 101761504
SVS: 117856747 117866461
PVIR: 120645322 120673040 120685455 120707392
PHAI: 112895638 112903000
PAUA: 133886571 133900767
TANG: 140761756 140765494 140776032
PDA: 103697377 103715683 103716756
EGU: 105044346 105046366 105052184 105056895
MUS: 103969297 135613426 135616988 135622424
ZOF: 122013056 122015262 122042988 122047500
DCT: 110099264
PEQ: 110021891
AOF: 109822179 109848520
MSIN: 131243823 131252805
ACAK: 137941994 137965793
NCOL: 116256758
ATR: 18436262
CJF: 131054653
SMO: SELMODRAFT_151304 SELMODRAFT_173304 SELMODRAFT_231600 SELMODRAFT_233175
PPP: 112285210 112288272
CME: CYME_CMM277C
GSL: Gasu_60480
CCP: CHC_T00010320001
DDI: DDB_G0279611
DPP: DICPUDRAFT_28679 DICPUDRAFT_42415 DICPUDRAFT_76018 DICPUDRAFT_80876
DFA: DFA_11723
ACAN: ACA1_360510
NGR: NAEGRDRAFT_61038
PSYC: DABAL43B_2672
SOK: D0B54_23595
AGE: AA314_00718
AVM: JQX13_12580
MBD: MEBOL_003525
CFUS: CYFUS_000150
 » show all
Reference
1  [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
2  [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 236:434-7 (1997)
DOI:10.1006/bbrc.1997.6974
Reference
3  [PMID:11707264]
  Authors
Darnet S, Bard M, Rahier A
  Title
Functional identification of sterol-4alpha-methyl oxidase cDNAs from Arabidopsis thaliana by complementation of a yeast erg25 mutant lacking sterol-4alpha-methyl oxidation.
  Journal
FEBS Lett 508:39-43 (2001)
DOI:10.1016/S0014-5793(01)03002-2
  Sequence
[ath:AT1G07420 AT2G29390]
Reference
4  [PMID:14653780]
  Authors
Darnet S, Rahier A
  Title
Plant sterol biosynthesis: identification of two distinct families of sterol 4alpha-methyl oxidases.
  Journal
Biochem J 378:889-98 (2004)
DOI:10.1042/BJ20031572
  Sequence
[ath:AT1G07420 AT2G29390]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.18.11
IUBMB Enzyme Nomenclature: 1.14.18.11
ExPASy - ENZYME nomenclature database: 1.14.18.11
BRENDA, the Enzyme Database: 1.14.18.11
LinkDB

KEGG   REACTION: R12379
Entry
R12379                      Reaction                               
Name
24-ethylidenelophenol,ferrocytochrome-b5:oxygen oxidoreductase (C-4alpha-methyl-hydroxylating)
Definition
24-Ethylidenelophenol + 6 Ferrocytochrome b5 + 3 Oxygen + 6 H+ <=> 4alpha-Carboxy-stigmasta-7,24(24(1))-dien-3beta-ol + 6 Ferricytochrome b5 + 4 H2O
Equation
C11523 + 6 C00999 + 3 C00007 + 6 C00080 <=> C22120 + 6 C00996 + 4 C00001
Comment
three-step reaction
Reaction class
RC03537  C11523_C22120
Enzyme
1.14.18.11
Pathway
rn00100  Steroid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00917  Phytosterol biosynthesis, squalene 2,3-epoxide => campesterol/sitosterol
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  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
    1.14.18.11
     R12379  24-Ethylidenelophenol + 6 Ferrocytochrome b5 + 3 Oxygen + 6 H+ <=> 4alpha-Carboxy-stigmasta-7,24(24(1))-dien-3beta-ol + 6 Ferricytochrome b5 + 4 H2O
Orthology
K14424  plant 4alpha-monomethylsterol monooxygenase [EC:1.14.18.11]
LinkDB

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