KEGG   ORTHOLOGY: K04123
Entry
K04123                      KO                                     
Symbol
KAO, CYP88A
Name
ent-kaurenoic acid monooxygenase [EC:1.14.14.107]
Pathway
map00904  Diterpenoid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00927  Gibberellin A12 biosynthesis, GAPP => GA12
Reaction
R06294  ent-kaur-16-en-19-oate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating)
R06295  ent-kaur-16-en-19-oate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating)
R06296  ent-kaur-16-en-19-oate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating)
R06297  ent-kaur-16-en-19-oate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating)
R10067  ent-kaur-16-en-19-oate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00904 Diterpenoid biosynthesis
    K04123  KAO, CYP88A; ent-kaurenoic acid monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K04123  KAO, CYP88A; ent-kaurenoic acid 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
    1.14.14.107  ent-kaurenoic acid monooxygenase
     K04123  KAO, CYP88A; ent-kaurenoic acid monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP88 family
   K04123  KAO, CYP88A; ent-kaurenoic acid monooxygenase
Other DBs
GO: 0051777
Genes
ATH: AT1G05160(CYP88A3) AT2G32440(KAO2)
ALY: 9315456 9328332
CRB: 17888804 17900740
CSAT: 104700214 104739049 104749619 104754659 104786342
EUS: EUTSA_v10009356mg EUTSA_v10016575mg
BRP: 103844165 103867649
BNA: 106371084 106401854 106440494 106451319
BOE: 106292794 106337055
RSZ: 108807314 108842714
THJ: 104826149
CPAP: 110806979 110806985 110806992 110807004 110808789 110808793
CIT: 102613483 102613777 102614081 102629702
CIC: CICLE_v10019986mg CICLE_v10031341mg CICLE_v10031862mg
PVY: 116117511 116134245 116146821 116146829
MINC: 123208728 123209742 123210303 123216284 123222953
TCC: 18585699 18606079 18606081 18606329
GRA: 105772884 105791949 105791951
GHI: 107900560 107918643 107918755 107919125 107933259 107933542 107962110 121204615
GAB: 108460315 108462417 108468286 108469217 108469308
HSYR: 120115073 120128206 120128234 120128417 120135153 120151789 120154041 120164160 120194368 120199482 120199484 120199485 120199486 120199487 120200624 120204184 120209995 120218103
DZI: 111290800 111290999 111296387 111318451
EGR: 104441311 104442000 104442001 104442002 104443188
GMX: 100775911 100781238 100813185
GSJ: 114368869 114385768 114422894
PVU: PHAVU_002G005900g PHAVU_006G123500g PHAVU_006G123600g
VRA: 106774485 106774855 106777479
VAR: 108335602 108340942 108341178 108341206
VUN: 114174667 114187411 114188643
VUM: 124823460 124849069 124849074 124849081
CCAJ: 109811458 109811471
APRC: 113848895 113852227 113859968 113869803 113874179
MTR: 11421816 25486343 25486344
TPRA: 123894420 123894421 123895690 123895691 123895692 123900978 123908724
CAM: 101498233 101511470 101512107
PSAT: 127074744 127074755
VVO: 131595340 131599817 131635548 131635549 131635550
LJA: 130724325 130724511 130724639 130726038 130731919 130732113 130740974
ADU: 107481709 107483271 107487552 107488636
AIP: 107631569 107631570 107638943
AHF: 112734534 112734535 112741528 112747996 112789995 112792330 112800419 112801238
LANG: 109330360 109330361 109332646 109333650 109341805 109350837
PCIN: 129284890 129288428 129289165 129289688 129304819 129323184
QSA: O6P43_017136 O6P43_024466 O6P43_026842
FVE: 101296899 101305225 101305520 101310426
RCN: 112173065 112179986 112181788
PPER: 18776554 18776771 18784549 18784550 18785864 18786347 18786970
PMUM: 103331385 103331394 103331395 103336931 103336981
PAVI: 110756042 110756077 110756078 110756080 110768794 110768800
PDUL: 117619068 117619515 117619538 117619561 117627601 117628494
MDM: 103407813 103418447 103420166 103438911
MSYL: 126609765 126626515 126627883
PXB: 103939254 103962469 103965514 108868325
ZJU: 107430468 107430486 107430487 107430488 107430491
MNT: 21406078 21406618
CSAV: 115710887 115715978
CSV: 101220640 101221667
CMO: 103483403 103498993
BHJ: 120069265 120070042 120087126 120089459 120091820 120092881
MCHA: 111016043 111022826
CMAX: 111479695 111494707
CMOS: 111432076 111464585
CPEP: 111778200 111791498
RCU: 8266689
MEAN: 126655385 126688050
JCU: 105644295
HBR: 110637522 110640195 110652612 110673668
MESC: 110613188 110613994 110626020
POP: 7464756 7469386
PEU: 105114977 105117216
PALZ: 118049585 118063426 118063428
PNZ: 133669310 133682529
JRE: 108989523 108994022 109003471 109003472 109003488 109003490 109009223 109012176 109014771
CILL: 122274663 122275386 122279873 122280545 122291578 122294386
CAVE: 132161623 132162420 132162422 132162428 132168004 132176212
QSU: 111998301 112005451 112005461 112022261
QLO: 115969956 115970103 115970145 115970147 115987237
TWL: 119979992 119982481 119983960 119985407 119985773 119985774 119985775 119985776 119985777 119988718 119993269 120003355 120003579 120014376 120014753 120016863 120017323 120017327
VVI: 100246155 100251295
VRI: 117931586 117931588
SLY: 101252522
SPEN: 107013820
SOT: 102603753
SSTN: 125853676
SDUL: 129886826 129895083 129900283
CANN: 107844151 107874876
LBB: 132609747 132615234 132645157
NTA: 107780044 107794300
NSY: 104249779
NTO: 104087090
NAU: 109231433
INI: 109155636 109156226 109156227 109156441 109156442 109163950 109163954 109178961
ITR: 115996900 116028387 116030480
SIND: 105167146 105173422
OEU: 111384195 111394261
EGT: 105952437 105954785
SSPL: 121774509 121776503 121792617 121800621 121806353
SMIL: 131015853 131015858 131015860 131022156 131022159
SHIS: 125185352 125196715 125202130 125202734
APAN: 127246080 127260462
HAN: 110922714
ECAD: 122595978 122598468
LSV: 111879980
CCAV: 112522539
DCR: 108200404 108206454
CSIN: 114264635 114274344
RVL: 131334167
AEW: 130783986 130794233
BVG: 104892989 104905197 104905198
SOE: 110790693 110793291 110793292
CQI: 110692430 110702167 110720433 110720434
ATRI: 130800751 130809742
MOF: 131166139 131166142
NNU: 104606451 104610396
MING: 122086087 122087349
TSS: 122645731 122663933
PSOM: 113348949
OSA: 4339885(CYP88A5)
OBR: 102701360
OGL: 127776322
BDI: 100829065 100834068 100840895
ATS: 109777068
TDC: 119288209 119334757
TAES: 100859955 123088429 123152052
LPER: 127311641
LRD: 124667563 124684951 124705881
SBI: 8067910
ZMA: 103639316 542580
MFLO: 136520709 136527894 136527895 136527917 136537289
SITA: 101759375 101783481
SVS: 117859799 117866907
PVIR: 120652866 120678416 120689309 120691937 120711185
PHAI: 112876728 112896230
PDA: 103706434 103714070
EGU: 105055009 105059578
MUS: 103978651 108951141
ZOF: 121973813 121973815 121975874 121977793 122002203 122006465
DCT: 110094431
PEQ: 110026319
AOF: 109822330
MSIN: 131233207 131248159
NCOL: 116266256
ATR: 18437415
SMO: SELMODRAFT_103517(CYP88E1) SELMODRAFT_115926 SELMODRAFT_127900(CYP88E2) SELMODRAFT_1840 SELMODRAFT_86321(CYP88F1)
 » show all
Reference
PMID:11172076 (CYP88A3 CYP88A4)
  Authors
Helliwell CA, Chandler PM, Poole A, Dennis ES, Peacock WJ
  Title
The CYP88A cytochrome P450, ent-kaurenoic acid oxidase, catalyzes three steps of the gibberellin biosynthesis pathway.
  Journal
Proc Natl Acad Sci U S A 98:2065-70 (2001)
DOI:10.1073/pnas.041588998
  Sequence
[ath:AT1G05160 AT2G32440]
LinkDB

KEGG   ORTHOLOGY: K12917
Entry
K12917            Tight     KO                                     
Symbol
P450I, CYP68A
Name
cytochrome P450 monooxygenase 1
Pathway
map00904  Diterpenoid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00929  Gibberellin A1 biosynthesis, GGPP => GA1
Reaction
R06294  ent-kaur-16-en-19-oate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating)
R06295  ent-kaur-16-en-19-oate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating)
R06339  
R06341  
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00904 Diterpenoid biosynthesis
    K12917  P450I, CYP68A; cytochrome P450 monooxygenase 1
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K12917  P450I, CYP68A; cytochrome P450 monooxygenase 1
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, fungi type
  CYP68 family
   K12917  P450I, CYP68A; cytochrome P450 monooxygenase 1
Genes
FMU: J7337_005026
AG: CAA75565(P450I)
Reference
PMID:11943776
  Authors
Tudzynski B, Rojas MC, Gaskin P, Hedden P
  Title
The gibberellin 20-oxidase of Gibberella fujikuroi is a multifunctional monooxygenase.
  Journal
J Biol Chem 277:21246-53 (2002)
DOI:10.1074/jbc.M201651200
  Sequence
[ag:CAA75565]
LinkDB

KEGG   ENZYME: 1.14.14.107
Entry
EC 1.14.14.107              Enzyme                                 
Name
ent-kaurenoic acid monooxygenase;
KAO1 (gene name);
CYP88A3 (gene name);
ent-kaurenoic acid oxidase
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
ent-kaur-16-en-19-oate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating)
Reaction(IUBMB)
ent-kaur-16-en-19-oate + 3 [reduced NADPH---hemoprotein reductase] + 3 O2 = gibberellin A12 + 3 [oxidized NADPH---hemoprotein reductase] + 4 H2O (overall reaction) [RN:R10067];
(1a) ent-kaur-16-en-19-oate + [reduced NADPH---hemoprotein reductase] + O2 = ent-7alpha-hydroxykaur-16-en-19-oate + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R06294];
(1b) ent-7alpha-hydroxykaur-16-en-19-oate + [reduced NADPH---hemoprotein reductase] + O2 = gibberellin A12 aldehyde + [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:R06295];
(1c) gibberellin A12 aldehyde + [reduced NADPH---hemoprotein reductase] + O2 = gibberellin A12 + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R06297]
Reaction(KEGG)
R06294 R06295 R06297 R10067;
(other) R06296
Substrate
ent-kaur-16-en-19-oate [CPD:C11874];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
ent-7alpha-hydroxykaur-16-en-19-oate [CPD:C11875];
gibberellin A12 aldehyde [CPD:C06093]
Product
gibberellin A12 [CPD:C11857];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
ent-7alpha-hydroxykaur-16-en-19-oate [CPD:C11875];
gibberellin A12 aldehyde [CPD:C06093]
Comment
A cytochrome P-450 (heme-thiolate) protein from plants. Catalyses three sucessive oxidations of ent-kaurenoic acid. The second step includes a ring-B contraction giving the gibbane skeleton. In pumpkin (Cucurbita maxima) ent-6alpha,7alpha-dihydroxykaur-16-en-19-oate is also formed.
History
EC 1.14.14.107 created 2002 as EC 1.14.13.79, transferred 2018 to EC 1.14.14.107
Pathway
ec00904  Diterpenoid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K04123  ent-kaurenoic acid monooxygenase
Genes
ATH: AT1G05160(CYP88A3) AT2G32440(KAO2)
ALY: 9315456 9328332
CRB: 17888804 17900740
CSAT: 104700214 104739049 104749619 104754659 104786342
EUS: EUTSA_v10009356mg EUTSA_v10016575mg
BRP: 103844165 103867649
BNA: 106371084 106401854 106440494 106451319
BOE: 106292794 106337055
RSZ: 108807314 108842714
THJ: 104826149
CPAP: 110806979 110806985 110806992 110807004 110808789 110808793
CIT: 102613483 102613777 102614081 102629702
CIC: CICLE_v10019986mg CICLE_v10031341mg CICLE_v10031862mg
PVY: 116117511 116134245 116146821 116146829
MINC: 123208728 123209742 123210303 123216284 123222953
TCC: 18585699 18606079 18606081 18606329
GRA: 105772884 105791949 105791951
GHI: 107900560 107918643 107918755 107919125 107933259 107933542 107962110 121204615
GAB: 108460315 108462417 108468286 108469217 108469308
HSYR: 120115073 120128206 120128234 120128417 120135153 120151789 120154041 120164160 120194368 120199482 120199484 120199485 120199486 120199487 120200624 120204184 120209995 120218103
DZI: 111290800 111290999 111296387 111318451
EGR: 104441311 104442000 104442001 104442002 104443188
GMX: 100775911 100781238 100813185
GSJ: 114368869 114385768 114422894
PVU: PHAVU_002G005900g PHAVU_006G123500g PHAVU_006G123600g
VRA: 106774485 106774855 106777479
VAR: 108335602 108340942 108341178 108341206
VUN: 114174667 114187411 114188643
VUM: 124823460 124849069 124849074 124849081
CCAJ: 109811458 109811471
APRC: 113848895 113852227 113859968 113869803 113874179
MTR: 11421816 25486343 25486344
TPRA: 123894420 123894421 123895690 123895691 123895692 123900978 123908724
CAM: 101498233 101511470 101512107
PSAT: 127074744 127074755
VVO: 131595340 131599817 131635548 131635549 131635550
LJA: 130724325 130724511 130724639 130726038 130731919 130732113 130740974
ADU: 107481709 107483271 107487552 107488636
AIP: 107631569 107631570 107638943
AHF: 112734534 112734535 112741528 112747996 112789995 112792330 112800419 112801238
LANG: 109330360 109330361 109332646 109333650 109341805 109350837
PCIN: 129284890 129288428 129289165 129289688 129304819 129323184
QSA: O6P43_017136 O6P43_024466 O6P43_026842
FVE: 101296899 101305225 101305520 101310426
RCN: 112173065 112179986 112181788
PPER: 18776554 18776771 18784549 18784550 18785864 18786347 18786970
PMUM: 103331385 103331394 103331395 103336931 103336981
PAVI: 110756042 110756077 110756078 110756080 110768794 110768800
PDUL: 117619068 117619515 117619538 117619561 117627601 117628494
MDM: 103407813 103418447 103420166 103438911
MSYL: 126609765 126626515 126627883
PXB: 103939254 103962469 103965514 108868325
ZJU: 107430468 107430486 107430487 107430488 107430491
MNT: 21406078 21406618
CSAV: 115710887 115715978
CSV: 101220640 101221667
CMO: 103483403 103498993
BHJ: 120069265 120070042 120087126 120089459 120091820 120092881
MCHA: 111016043 111022826
CMAX: 111479695 111494707
CMOS: 111432076 111464585
CPEP: 111778200 111791498
RCU: 8266689
MEAN: 126655385 126688050
JCU: 105644295
HBR: 110637522 110640195 110652612 110673668
MESC: 110613188 110613994 110626020
POP: 7464756 7469386
PEU: 105114977 105117216
PALZ: 118049585 118063426 118063428
PNZ: 133669310 133682529
JRE: 108989523 108994022 109003471 109003472 109003488 109003490 109009223 109012176 109014771
CILL: 122274663 122275386 122279873 122280545 122291578 122294386
CAVE: 132161623 132162420 132162422 132162428 132168004 132176212
QSU: 111998301 112005451 112005461 112022261
QLO: 115969956 115970103 115970145 115970147 115987237
TWL: 119979992 119982481 119983960 119985407 119985773 119985774 119985775 119985776 119985777 119988718 119993269 120003355 120003579 120014376 120014753 120016863 120017323 120017327
VVI: 100246155 100251295
VRI: 117931586 117931588
SLY: 101252522
SPEN: 107013820
SOT: 102603753
SSTN: 125853676
SDUL: 129886826 129895083 129900283
CANN: 107844151 107874876
LBB: 132609747 132615234 132645157
NTA: 107780044 107794300
NSY: 104249779
NTO: 104087090
NAU: 109231433
INI: 109155636 109156226 109156227 109156441 109156442 109163950 109163954 109178961
ITR: 115996900 116028387 116030480
SIND: 105167146 105173422
OEU: 111384195 111394261
EGT: 105952437 105954785
SSPL: 121774509 121776503 121792617 121800621 121806353
SMIL: 131015853 131015858 131015860 131022156 131022159
SHIS: 125185352 125196715 125202130 125202734
APAN: 127246080 127260462
HAN: 110922714
ECAD: 122595978 122598468
LSV: 111879980
CCAV: 112522539
DCR: 108200404 108206454
CSIN: 114264635 114274344
RVL: 131334167
AEW: 130783986 130794233
BVG: 104892989 104905197 104905198
SOE: 110790693 110793291 110793292
CQI: 110692430 110702167 110720433 110720434
ATRI: 130800751 130809742
MOF: 131166139 131166142
NNU: 104606451 104610396
MING: 122086087 122087349
TSS: 122645731 122663933
PSOM: 113348949
OSA: 4339885(CYP88A5)
OBR: 102701360
OGL: 127776322
BDI: 100829065 100834068 100840895
ATS: 109777068
TDC: 119288209 119334757
TAES: 100859955 123088429 123152052
LPER: 127311641
LRD: 124667563 124684951 124705881
SBI: 8067910
ZMA: 103639316 542580
MFLO: 136520709 136527894 136527895 136527917 136537289
SITA: 101759375 101783481
SVS: 117859799 117866907
PVIR: 120652866 120678416 120689309 120691937 120711185
PHAI: 112876728 112896230
PDA: 103706434 103714070
EGU: 105055009 105059578
MUS: 103978651 108951141
ZOF: 121973813 121973815 121975874 121977793 122002203 122006465
DCT: 110094431
PEQ: 110026319
AOF: 109822330
MSIN: 131233207 131248159
NCOL: 116266256
ATR: 18437415
SMO: SELMODRAFT_103517(CYP88E1) SELMODRAFT_115926 SELMODRAFT_127900(CYP88E2) SELMODRAFT_1840 SELMODRAFT_86321(CYP88F1)
 » show all
Reference
1  [PMID:11172076]
  Authors
Helliwell CA, Chandler PM, Poole A, Dennis ES, Peacock WJ
  Title
The CYP88A cytochrome P450, ent-kaurenoic acid oxidase, catalyzes three steps of the gibberellin biosynthesis pathway.
  Journal
Proc Natl Acad Sci U S A 98:2065-70 (2001)
DOI:10.1073/pnas.041588998
  Sequence
[ath:AT1G05160 AT2G32440]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.107
IUBMB Enzyme Nomenclature: 1.14.14.107
ExPASy - ENZYME nomenclature database: 1.14.14.107
BRENDA, the Enzyme Database: 1.14.14.107
CAS: 337507-95-6
LinkDB

KEGG   REACTION: R06295
Entry
R06295                      Reaction                               
Name
ent-kaur-16-en-19-oate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating)
Definition
ent-7alpha-Hydroxykaur-16-en-19-oic acid + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Gibberellin A12 aldehyde + [Oxidized NADPH---hemoprotein reductase] + 2 H2O
Equation
C11875 + C03024 + C00007 <=> C06093 + C03161 + 2 C00001
Comment
the second step of three-step reaction (see R10067, R06294+R06295+R06297)
Reaction class
RC01622  C06093_C11875
Enzyme
1.14.14.107
Pathway
rn00904  Diterpenoid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00927  Gibberellin A12 biosynthesis, GAPP => GA12
M00929  Gibberellin A1 biosynthesis, GGPP => GA1
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  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
    1.14.14.107
     R06295  ent-7alpha-Hydroxykaur-16-en-19-oic acid + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Gibberellin A12 aldehyde + [Oxidized NADPH---hemoprotein reductase] + 2 H2O
Orthology
K04123  ent-kaurenoic acid monooxygenase [EC:1.14.14.107]
K12917  cytochrome P450 monooxygenase 1
Other DBs
RHEA: 22907
LinkDB

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