KEGG   ORTHOLOGY: K09754
Entry
K09754                      KO                                     
Symbol
CYP98A, C3'H
Name
5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase [EC:1.14.14.96]
Pathway
map00940  Phenylpropanoid biosynthesis
map00941  Flavonoid biosynthesis
map00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00039  Monolignol biosynthesis, phenylalanine/tyrosine => monolignol
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00940 Phenylpropanoid biosynthesis
    K09754  CYP98A, C3'H; 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
   00945 Stilbenoid, diarylheptanoid and gingerol biosynthesis
    K09754  CYP98A, C3'H; 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
   00941 Flavonoid biosynthesis
    K09754  CYP98A, C3'H; 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K09754  CYP98A, C3'H; 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
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
    1.14.14.96  5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
     K09754  CYP98A, C3'H; 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP98 family
   K09754  CYP98A, C3'H; 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
Other DBs
RN: R04342 R06582
GO: 0047083
Genes
ATH: AT2G40890(CYP98A3)
ALY: 9315964
CRB: 17887658
CSAT: 104782574 104785308 104792955
EUS: EUTSA_v10016538mg
BRP: 103857960 103865848 103866522
BNA: 106352767 106386334 106391625 106395719 106431114 106438010 106454525
BOE: 106335822 106340718 106342398
RSZ: 108847330 108848401 108857959 108858042 108860679
THJ: 104803227
CPAP: 110811301
CIT: 102624231
PVY: 116130453
TCC: 18598608
DZI: 111293639
GMX: 100811080 606506(CYP98A2)
VRA: 106753926
VAR: 108346061
VUN: 114186352
CCAJ: 109802555
APRC: 113861260
CAM: 101502624
LJA: Lj1g3v4081860.1(Lj1g3v4081860.1)
ADU: 107494128
AIP: 107604697
LANG: 109326958
FVE: 101310387
RCN: 112191575
ZJU: 107431535
MNT: 21410476
CSV: 101217257
CMO: 103486874
BHJ: 120091747
CMAX: 111482281
CMOS: 111441713
CPEP: 111790179
JCU: 105636120
HBR: 110668477
MESC: 110621178
QLO: 115953326
TWL: 119992803
VVI: 100263633
VRI: 117920828
INI: 109159148
NNU: 104588272
NCOL: 116245980
OSA: 4339188
DOSA: Os05t0494000-01(Os05g0494000)
OBR: 102712257
BDI: 100835531
SITA: 101771055
SVS: 117849885
MUS: 103995155
DCT: 110101632
PEQ: 110024997
AOF: 109819911
SMO: SELMODRAFT_450942(C3'H1-1) SELMODRAFT_450943(C3'H1-2)
PPP: 112275074
AG: AAL99200(CYP98A13v1) AAL99201(CYP98A13v2) CAE47490(CYP98A11)
 » show all
Reference
PMID:9484480 (CYP98A1)
  Authors
Bak S, Kahn RA, Nielsen HL, Moller BL, Halkier BA
  Title
Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin.
  Journal
Plant Mol Biol 36:393-405 (1998)
DOI:10.1023/A:1005915507497
  Sequence
[sbi:8077042]
Reference
PMID:17160453 (CYP98A11)
  Authors
Morant M, Schoch GA, Ullmann P, Ertunc T, Little D, Olsen CE, Petersen M, Negrel J, Werck-Reichhart D
  Title
Catalytic activity, duplication and evolution of the CYP98 cytochrome P450 family in wheat.
  Journal
Plant Mol Biol 63:1-19 (2007)
DOI:10.1007/s11103-006-9028-8
  Sequence
Reference
PMID:12428018 (CYP98A13)
  Authors
Gang DR, Beuerle T, Ullmann P, Werck-Reichhart D, Pichersky E
  Title
Differential production of meta hydroxylated phenylpropanoids in sweet basil peltate glandular trichomes and leaves is controlled by the activities of specific acyltransferases and hydroxylases.
  Journal
Plant Physiol 130:1536-44 (2002)
DOI:10.1104/pp.007146
  Sequence
Reference
  Authors
Costa MA, Collins RE, Anterola AM, Cochrane FC, Davin LB, Lewis NG.
  Title
An in silico assessment of gene function and organization of the phenylpropanoid pathway metabolic networks in Arabidopsis thaliana and limitations thereof.
  Journal
Phytochemistry 64:1097-112 (2003)
DOI:10.1016/S0031-9422(03)00517-X
LinkDB

KEGG   ENZYME: 1.14.14.96
Entry
EC 1.14.14.96               Enzyme                                 
Name
5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase;
5-O-(4-coumaroyl)-D-quinate/shikimate 3'-hydroxylase;
coumaroylquinate(coumaroylshikimate) 3'-monooxygenase;
CYP98A3 (gene name)
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
trans-5-O-(4-coumaroyl)-D-quinate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
Reaction(IUBMB)
trans-5-O-(4-coumaroyl)-D-quinate + [reduced NADPH---hemoprotein reductase] + O2 = trans-5-O-caffeoyl-D-quinate + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R04342]
Reaction(KEGG)
R04342;
(other) R06582
Substrate
trans-5-O-(4-coumaroyl)-D-quinate [CPD:C12208];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
trans-5-O-caffeoyl-D-quinate [CPD:C00852];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) protein, found in plants. It also acts on trans-5-O-(4-coumaroyl)shikimate.
History
EC 1.14.14.96 created 1990 as EC 1.14.13.36, transferred 2018 to EC 1.14.14.96
Pathway
ec00940  Phenylpropanoid biosynthesis
ec00941  Flavonoid biosynthesis
ec00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K09754  5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
Genes
ATHAT2G40890(CYP98A3)
ALY9315964
CRB17887658
CSAT104782574 104785308 104792955
EUSEUTSA_v10016538mg
BRP103857960 103865848 103866522
BNA106352767 106386334 106391625 106395719 106431114 106438010 106454525
BOE106335822 106340718 106342398
RSZ108847330 108848401 108857959 108858042 108860679
THJ104803227
CPAP110811301
CIT102624231
CICCICLE_v10000848mg CICLE_v10003647mg CICLE_v10011520mg CICLE_v10019813mg
PVY116130453
MINC123211020 123211225 123224750
TCC18598608
GRA105782306 105786247
GHI107920919 107935532 107950342 121229624
GAB108464295 108466431
DZI111293639
EGR104443731 104443755 104454510
GMX100811080 606506(CYP98A2)
GSJ114399785 114406591
PVUPHAVU_001G117900g
VRA106753926
VAR108346061
VUN114186352
CCAJ109802555
APRC113861260
CAM101502624
LJALj1g3v4081860.1(Lj1g3v4081860.1)
ADU107494128
AIP107604697
AHF112696779 112754637
LANG109326958
FVE101310387
RCN112191575
PPER18789678 18789708 18789709 18792412
PMUM103319005 103319006 103319007
PAVI110765625 110765626 110765627 110765628 110771536
PDUL117612862 117616059 117616060 117629116
MDM103402429 103425389 103428961 103441965
PXB103944996 103944997 103944999 103946365 103946366
ZJU107431535
MNT21410476
CSV101217257
CMO103486874
BHJ120091747
CMAX111482281
CMOS111441713
CPEP111790179
RCU8277408 8277879 8277880
JCU105636120
HBR110668477
MESC110621178
POP7458907 7495679
PEU105136908 105137345
PALZ118033187 118033188 118052995
JRE109008126 109008127 109019007
QSU112007479 112007503
QLO115953326
TWL119992803
VVI100263633
VRI117920828
SLY101246092 101247849 101261765 101262063 101262367
SPEN107001769 107001863 107002593 107008188 107028331
SOT102578406 102578747 102586130 102590105 102590484 102590830 102590870 102606401
SSTN125863836 125865331 125865642 125865643 125865644 125865645 125871059
CANN107839366 107844023 107844024 107844025
NTA107767804 107768690 107771987 107792896 107797681 107800961 107803600 107824233(CYP98A33v1)
NSY104216569 104221515 104228627 104235549
NTO104088297 104092594 104112912 104119156
NAU109221014 109228215 109239726 109239730
INI109159148
ITR115996353 116029460
SIND105162700 105172202
OEU111391169 111401521
EGT105949334 105949335 105951765 105951768 105951769 105963605
SSPL121747388 121747439 121751565 121753302 121804071 121805425 121805775 121806378 121808561
HAN110865896 110895770
ECAD122579549 122582247
LSV111877005 111891710 111908828 111919428
CCAV112504027 112512472
DCR108209804 108227431
CSIN114298795 114303480 114303482
BVG104887604 104889547 104889649 104889748
SOE110778982 110779503 110799229
CQI110709209 110711729 110714717 110714951 110717575 110720052
NNU104588272
MING122063491 122063496 122068462 122069164 122088749
TSS122666848 122669889
PSOM113298939 113358675
NCOL116245980
OSA4339188
DOSAOs05t0494000-01(Os05g0494000)
OBR102712257
BDI100835531
ATS109731922 109752053 109757203 109771149 109775586
TDC119269306 119277305 119284878 119348794
TAES123060768 123062331 123071098 123079468 123100799 123108593 123137844 123182452
TUA125506560 125522601 125545066
SBI8077042 8082405
ZMA100191539 100274274
SITA101771055
SVS117849885
PVIR120665065 120673263 120698273
PHAI112887100 112894578
PDA103705056 103706282
EGU105033349 105052441
MUS103995155
DCT110101632
PEQ110024997
AOF109819911
ATR18427105 18441256
SMOSELMODRAFT_450942(C3'H1-1) SELMODRAFT_450943(C3'H1-2)
PPP112275074
 » show all
Reference
1  [PMID:2821918]
  Authors
Kuhnl T, Koch U, Heller W, Wellmann E.
  Title
Chlorogenic acid biosynthesis: characterization of a light-induced microsomal 5-O-(4-coumaroyl)-D-quinate/shikimate 3'-hydroxylase from carrot (Daucus carota L.) cell suspension cultures.
  Journal
Arch Biochem Biophys 258:226-32 (1987)
DOI:10.1016/0003-9861(87)90339-0
Reference
2  [PMID:11429408]
  Authors
Schoch G, Goepfert S, Morant M, Hehn A, Meyer D, Ullmann P, Werck-Reichhart D
  Title
CYP98A3 from Arabidopsis thaliana is a 3'-hydroxylase of phenolic esters, a missing link in the phenylpropanoid pathway.
  Journal
J Biol Chem 276:36566-74 (2001)
DOI:10.1074/jbc.M104047200
  Sequence
[ath:AT2G40890]
Reference
3  [PMID:11967091]
  Authors
Franke R, Humphreys JM, Hemm MR, Denault JW, Ruegger MO, Cusumano JC, Chapple C
  Title
The Arabidopsis REF8 gene encodes the 3-hydroxylase of phenylpropanoid metabolism.
  Journal
Plant J 30:33-45 (2002)
DOI:10.1046/j.1365-313X.2002.01266.x
  Sequence
[ath:AT2G40890]
Reference
4  [PMID:19779199]
  Authors
Matsuno M, Compagnon V, Schoch GA, Schmitt M, Debayle D, Bassard JE, Pollet B, Hehn A, Heintz D, Ullmann P, Lapierre C, Bernier F, Ehlting J, Werck-Reichhart D
  Title
Evolution of a novel phenolic pathway for pollen development.
  Journal
Science 325:1688-92 (2009)
DOI:10.1126/science.1174095
  Sequence
[ath:AT2G40890]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.96
IUBMB Enzyme Nomenclature: 1.14.14.96
ExPASy - ENZYME nomenclature database: 1.14.14.96
BRENDA, the Enzyme Database: 1.14.14.96
CAS: 112131-08-5
LinkDB

KEGG   REACTION: R06582
Entry
R06582                      Reaction                               
Name
trans-5-O-(4-coumaroyl)-D-shikimate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
Definition
4-Coumaroylshikimate + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> 5-O-Caffeoylshikimic acid + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
Reaction class
RC00046  C02947_C10434
Enzyme
Pathway
rn00940  Phenylpropanoid biosynthesis
rn00941  Flavonoid biosynthesis
rn00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00039  Monolignol biosynthesis, phenylalanine/tyrosine => monolignol
Orthology
K09754  5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase [EC:1.14.14.96]
LinkDB

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