KEGG   ORTHOLOGY: K09587
Entry
K09587                      KO                                     
Symbol
CYP90B, DWF4
Name
steroid 22S-hydroxylase [EC:1.14.14.178]
Pathway
map00905  Brassinosteroid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00371  Castasterone biosynthesis, campesterol => castasterone
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00905 Brassinosteroid biosynthesis
    K09587  CYP90B, DWF4; steroid 22S-hydroxylase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K09587  CYP90B, DWF4; steroid 22S-hydroxylase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.178  steroid 22S-hydroxylase
     K09587  CYP90B, DWF4; steroid 22S-hydroxylase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP90 family
   K09587  CYP90B, DWF4; steroid 22S-hydroxylase
Other DBs
RN: R07430 R07445 R07452 R07453 R07454
Genes
ATH: AT3G50660(DWF4)
ALY: 9312109
CRB: 17885187
CSAT: 104780889 104791284
EUS: EUTSA_v10011005mg
BRP: 103828198 103840968
BNA: 106401625 106405681 106447365
BOE: 106310362 106321383
RSZ: 108809973 108826420 108826548
THJ: 104819220 104826953
CPAP: 110822261
CIT: 102623486
TCC: 18610945
GRA: 105803806
GAB: 108471227
EGR: 104419755
LJA: Lj0g3v0324529.1(Lj0g3v0324529.1)
ADU: 107487855
AIP: 107642870
FVE: 101304220
RCN: 112187887
PPER: 18770032
PMUM: 103340078
PAVI: 110773452
PDUL: 117635807
MNT: 21395422
CSV: 101211854
CMO: 103494380
BHJ: 120069803
MCHA: 111008332
CMAX: 111479953
CMOS: 111446972
CPEP: 111807994
RCU: 8273425
MESC: 110603714
QSU: 112006212
QLO: 115994961
VVI: 100241065
VRI: 117913676
SLY: 101256342(CYP90B3)
SPEN: 107009445
SOT: 102603786
SSTN: 125849264
CANN: 107859954
NSY: 104210061
NTO: 104115826
NAU: 109210801
INI: 109168575
ITR: 116011693
SIND: 105177981
EGT: 105954961
HAN: 110915264
ECAD: 122579500
CCAV: 112513520
DCR: 108220768
CSIN: 114274957
BVG: 104895859
SOE: 110797811
NCOL: 116260033
OSA: 4332134
DOSA: Os03t0227700-01(Os03g0227700)
OBR: 102709630
BDI: 100837605
SBI: 8056846
ZMA: 100191562
SITA: 101770693
SVS: 117841038
PHAI: 112875152
ATR: 18445832
 » show all
Reference
PMID:9490746
  Authors
Choe S, Dilkes BP, Fujioka S, Takatsuto S, Sakurai A, Feldmann KA
  Title
The DWF4 gene of Arabidopsis encodes a cytochrome P450 that mediates multiple 22alpha-hydroxylation steps in brassinosteroid biosynthesis.
  Journal
Plant Cell 10:231-43 (1998)
DOI:10.1105/tpc.10.2.231
  Sequence
[ath:AT3G50660]
Reference
  Authors
Fujita S, Ohnishi T, Watanabe B, Yokota T, Takatsuto S, Fujioka S, Yoshida S, Sakata K, Mizutani M.
  Title
Arabidopsis CYP90B1 catalyses the early C-22 hydroxylation of C27, C28 and C29 sterols.
  Journal
Plant J 45:765-74 (2006)
DOI:10.1111/j.1365-313X.2005.02639.x
  Sequence
[ath:AT3G50660]
LinkDB

KEGG   ORTHOLOGY: K12639
Entry
K12639                      KO                                     
Symbol
CYP724, D11
Name
steroid 22S-hydroxylase [EC:1.14.14.178]
Pathway
map00905  Brassinosteroid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00371  Castasterone biosynthesis, campesterol => castasterone
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00905 Brassinosteroid biosynthesis
    K12639  CYP724, D11; steroid 22S-hydroxylase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K12639  CYP724, D11; steroid 22S-hydroxylase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.178  steroid 22S-hydroxylase
     K12639  CYP724, D11; steroid 22S-hydroxylase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP724 family
   K12639  CYP724, D11; steroid 22S-hydroxylase
Other DBs
RN: R07445 R07452 R07453 R07454
Genes
ATH: AT5G14400(CYP724A1)
ALY: 9307686
CRB: 17882948
CSAT: 104769675
EUS: EUTSA_v10015753mg
BRP: 103846487 103850927
BNA: 106364625 106370550 106417880 106429943
BOE: 106317102 106326221
RSZ: 108816728 108841135 108841282
THJ: 104802390
GMX: 100791737
GSJ: 114389140
CCAJ: 109793322
APRC: 113859482
LJA: Lj2g3v0043650.1(Lj2g3v0043650.1)
LANG: 109350644
PXB: 103951781
MNT: 21400684
CSV: 101215045
CMO: 103498124
BHJ: 120079590
MCHA: 111006083
CMAX: 111487092
CMOS: 111430228
CPEP: 111808675
JRE: 109009656
TWL: 120011489
SLY: 101251900(CYP724B2) 101265305
SOT: 102582442
OEU: 111389155
HAN: 110895233
ECAD: 122598110
LSV: 111918657
CCAV: 112516322
OSA: 4336116
DOSA: Os04t0469800-01(Os04g0469800)
OBR: 102717238
BDI: 100833643
ATS: 109734230
TUA: 125526986
ZMA: 100217085
PDA: 103721661
EGU: 105060809
DCT: 110112973
AOF: 109840188
 » show all
Reference
  Authors
Tanabe S, Ashikari M, Fujioka S, Takatsuto S, Yoshida S, Yano M, Yoshimura A, Kitano H, Matsuoka M, Fujisawa Y, Kato H, Iwasaki Y
  Title
A novel cytochrome P450 is implicated in brassinosteroid biosynthesis via the characterization of a rice dwarf mutant, dwarf11, with reduced seed length.
  Journal
Plant Cell 17:776-90 (2005)
DOI:10.1105/tpc.104.024950
  Sequence
[osa:4336116]
Reference
  Authors
Ohnishi T, Watanabe B, Sakata K, Mizutani M.
  Title
CYP724B2 and CYP90B3 function in the early C-22 hydroxylation steps of brassinosteroid biosynthetic pathway in tomato.
  Journal
Biosci Biotechnol Biochem 70:2071-80 (2006)
DOI:10.1271/bbb.60034
  Sequence
[sly:101251900]
LinkDB

KEGG   ENZYME: 1.14.14.178
Entry
EC 1.14.14.178              Enzyme                                 
Name
steroid 22S-hydroxylase;
CYP90B1 (gene name);
DWF4 (gene name);
steroid C-22 hydroxylase
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
steroid,NADPH---hemoprotein reductase:oxygen 22S-oxidoreductase (hydroxylating)
Reaction(IUBMB)
(1) a C27 steroid + O2 + [reduced NADPH---hemoprotein reductase] = a (22S)-22-hydroxy-C27 steroid + 2 H2O + [oxidized NADPH---hemoprotein reductase];
(2) a C28 steroid + O2 + [reduced NADPH---hemoprotein reductase] = a (22S)-22-hydroxy-C28 steroid + 2 H2O + [oxidized NADPH---hemoprotein reductase];
(3) a C29 steroid + O2 + [reduced NADPH---hemoprotein reductase] = a (22S)-22-hydroxy-C29 steroid + 2 H2O + [oxidized NADPH---hemoprotein reductase]
Reaction(KEGG)
(other) R07445 R07452 R07453 R07454
Substrate
C27 steroid;
O2 [CPD:C00007];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
C28 steroid;
C29 steroid
Product
(22S)-22-hydroxy-C27 steroid;
H2O [CPD:C00001];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
(22S)-22-hydroxy-C28 steroid;
(22S)-22-hydroxy-C29 steroid
Comment
This plant cytochrome P-450 (heme thiolate) enzyme participates in the biosynthesis of brassinosteroids. While in vivo substrates include C28 steroids such as campestanol, campesterol, and 6-oxocampestanol, the enzyme is able to catalyse the C-22 hydroxylation of a variety of C27, C28 and C29 steroids.
History
EC 1.14.14.178 created 2022
Pathway
ec00905  Brassinosteroid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K09587  steroid 22S-hydroxylase
K12639  steroid 22S-hydroxylase
Genes
ATHAT3G50660(DWF4) AT5G14400(CYP724A1)
ALY9307686 9312109
CRB17882948 17885187
CSAT104769675 104780889 104791284
EUSEUTSA_v10011005mg EUTSA_v10015753mg
BRP103828198 103840968 103846487 103850927
BNA106364625 106370550 106401625 106405681 106417880 106429943 106447365
BOE106310362 106317102 106321383 106326221
RSZ108809973 108816728 108826420 108826548 108841135 108841282
THJ104802390 104819220 104826953
CPAP110808733 110808955 110822261
CIT102607509 102623486 102625685
CICCICLE_v10015033mg CICLE_v10017470mg CICLE_v10025451mg
PVY116113019 116113135 116118304 116118306 116142804
MINC123195983 123199643 123199686 123214950 123216538 123222469
TCC18600875 18610945 18612531
GRA105779232 105803387 105803806
GHI107896149 107912480 107913065 107922960 107926035 107961481
GAB108460073 108471227 108472771
DZI111292390 111292725 111300505 111301072 111306191 111313510 111316237
EGR104419198 104419755 104420630
GMX100789515 100791737 100800210 100802498
GSJ114377375 114382291 114389140 114420632
PVUPHAVU_002G029700g PHAVU_003G253100g PHAVU_008G147500g
VRA106765911 106778030
VAR108334671 108335822
VUN114166425 114179641
CCAJ109793322 109801635 109810494
APRC113859349 113859482 113868805
MTRMTR_5g020020 MTR_7g033040 MTR_8g077810
CAM101499755 101500152
LJALj0g3v0324529.1(Lj0g3v0324529.1) Lj2g3v0043650.1(Lj2g3v0043650.1)
ADU107487855
AIP107642870
AHF112749146 112800701
LANG109331920 109348687 109350644
FVE101296274 101304220 101308903
RCN112183385 112187887 112187901
PPER18770032 18782463 18784320
PMUM103329118 103330155 103340078
PAVI110755657 110756001 110773452
PDUL117621138 117622631 117635807
MDM103401164 103401541 103405248 103429004 103442738
PXB103941521 103951781 103960819
ZJU107408367 107408382 107408649 107409125 107415245 107416825 107435422
MNT21395422 21400684
CSV101211854 101215045
CMO103494380 103498124
BHJ120069803 120079590
MCHA111006083 111008332
CMAX111479953 111487092
CMOS111430228 111446972
CPEP111807994 111808675
RCU8260354 8273425 8288322
JCU105634541 105643410
HBR110634320 110654062 110656526 110665021 110671515
MESC110602755 110603714 110605043 110629477
POP18099286 18101214 7467663 7469349
PEU105110409 105116030 105116836 105126568
PALZ118030029 118054146 118058119 118063301
JRE108995250 108997500 109009656
QSU111993132 111999072 112006212 112023948
QLO115978378 115987302 115994961
TWL120000980 120011489 120014527
VVI100241065 100245690 100257922
VRI117913676 117926615 117931086
SLY101251900(CYP724B2) 101256342(CYP90B3) 101265305
SPEN107009445 107010789 107024375
SOT102582442 102603786
SSTN125847510 125847511 125849264 125877193
CANN107858413 107859954 107877366
NTA107776917 107779615 107795428 107795954 107801070 107825897
NSY104210061 104212166 104243183
NTO104100965 104104628 104115826
NAU109207893 109210801 109217467 109221822
INI109158109 109168575 109187712
ITR115998915 116011467 116011693
SIND105176862 105177981 105179881
OEU111367619 111380525 111389155
EGT105954961 105970780 105976276
SSPL121767277 121772586 121774314 121802385 121806412
HAN110895233 110915264
ECAD122579500 122598110
LSV111883587 111918657 111919095
CCAV112513520 112516322
DCR108220768 108221483 108224415 108227649
CSIN114274957 114316234 114318951
BVG104895859
SOE110797811
CQI110686172 110722522
NNU104591542 104595706 104601879 104608289
MING122073840 122078302 122083658 122094194
TSS122638371 122640557 122654025 122658580 122661166
PSOM113273094 113285824 113289235 113293814 113301538
NCOL116249569 116259560 116260033
OSA4332134 4336116
DOSAOs03t0227700-01(Os03g0227700) Os04t0469800-01(Os04g0469800)
OBR102709630 102717238
BDI100833643 100837605
ATS109734230 109742297 109786179
TDC119273638 119285031 119291093 119355441 119364561
TAES123045717 123053590 123059596 123066933 123075890 123085252 123092868 123098154 123189488
TUA125526986 125549501 125552395
SBI8055423 8056846 8058684
ZMA100191562 100217085
SITA101768860 101769663 101770693
SVS117841038 117855539 117865849
PVIR120641205 120646755 120652021 120683428 120688207 120691708
PHAI112874677 112875152 112901555
PDA103697967 103704238 103707598 103707601 103721661 120113249
EGU105055939 105058149 105060750 105060809
MUS103974765 103981133 103981633 103983905 103996193 103996195
DCT110092799 110112973 110114079 110114986
PEQ110019548 110025965
AOF109833124 109834320 109834432 109840188
ATR18445832 18447481 18448244
 » show all
Reference
1  [PMID:11319239]
  Authors
Asami T, Mizutani M, Fujioka S, Goda H, Min YK, Shimada Y, Nakano T, Takatsuto S, Matsuyama T, Nagata N, Sakata K, Yoshida S.
  Title
Selective interaction of triazole derivatives with DWF4, a cytochrome P450 monooxygenase of the brassinosteroid biosynthetic pathway, correlates with brassinosteroid deficiency in planta.
  Journal
J Biol Chem 276:25687-91 (2001)
DOI:10.1074/jbc.M103524200
Reference
2  [PMID:11489171]
  Authors
Choe S, Fujioka S, Noguchi T, Takatsuto S, Yoshida S, Feldmann KA.
  Title
Overexpression of DWARF4 in the brassinosteroid biosynthetic pathway results in increased vegetative growth and seed yield in Arabidopsis.
  Journal
Plant J 26:573-82 (2001)
DOI:10.1046/j.1365-313x.2001.01055.x
  Sequence
[ath:AT3G50660]
Reference
3  [PMID:12350224]
  Authors
Asami T, Mizutani M, Shimada Y, Goda H, Kitahata N, Sekimata K, Han SY, Fujioka S, Takatsuto S, Sakata K, Yoshida S.
  Title
Triadimefon, a fungicidal triazole-type P450 inhibitor, induces brassinosteroid deficiency-like phenotypes in plants and binds to DWF4 protein in the brassinosteroid biosynthesis pathway.
  Journal
Biochem J 369:71-6 (2003)
DOI:10.1042/BJ20020835
Reference
4  [PMID:16460510]
  Authors
Fujita S, Ohnishi T, Watanabe B, Yokota T, Takatsuto S, Fujioka S, Yoshida S, Sakata K, Mizutani M.
  Title
Arabidopsis CYP90B1 catalyses the early C-22 hydroxylation of C27, C28 and C29 sterols.
  Journal
Plant J 45:765-74 (2006)
DOI:10.1111/j.1365-313X.2005.02639.x
Reference
5  [PMID:16960392]
  Authors
Ohnishi T, Watanabe B, Sakata K, Mizutani M.
  Title
CYP724B2 and CYP90B3 function in the early C-22 hydroxylation steps of brassinosteroid biosynthetic pathway in tomato.
  Journal
Biosci Biotechnol Biochem 70:2071-80 (2006)
DOI:10.1271/bbb.60034
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.178
IUBMB Enzyme Nomenclature: 1.14.14.178
ExPASy - ENZYME nomenclature database: 1.14.14.178
BRENDA, the Enzyme Database: 1.14.14.178
LinkDB

KEGG   REACTION: R07453
Entry
R07453                      Reaction                               
Name
5alpha-campestan-3-one,NADPH---hemoprotein reductase:oxygen 22S-oxidoreductase (hydroxylating)
Definition
5alpha-Campestan-3-one + Oxygen + [Reduced NADPH---hemoprotein reductase] <=> 22alpha-Hydroxy-5alpha-campestan-3-one + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
Reaction class
RC00773  C15786_C15797
Enzyme
Pathway
rn00905  Brassinosteroid biosynthesis
rn01100  Metabolic pathways
Orthology
K09587  steroid 22S-hydroxylase [EC:1.14.14.178]
K12639  steroid 22S-hydroxylase [EC:1.14.14.178]
LinkDB

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