KEGG   ENZYME: 1.14.14.126
Entry
EC 1.14.14.126              Enzyme                                 
Name
beta-amyrin 28-monooxygenase;
CYP716A52v2;
CYP716A12;
CYP16A75;
beta-amyrin 28-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
beta-amyrin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (28-hydroxylating)
Reaction(IUBMB)
beta-amyrin + 3 O2 + 3 [reduced NADPH---hemoprotein reductase] = oleanolate + 3 [oxidized NADPH---hemoprotein reductase] + 4 H2O (overall reaction) [RN:R10924];
(1a) beta-amyrin + O2 + [reduced NADPH---hemoprotein reductase] = erythrodiol + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R10921];
(1b) erythrodiol + O2 + [reduced NADPH---hemoprotein reductase] = oleanolic aldehyde + [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:R10922];
(1c) oleanolic aldehyde + O2 + [reduced NADPH---hemoprotein reductase] = oleanolate + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R10923]
Reaction(KEGG)
R10921 R10922 R10923 R10924
Substrate
beta-amyrin [CPD:C08616];
O2 [CPD:C00007];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
erythrodiol [CPD:C20945];
oleanolic aldehyde [CPD:C20946]
Product
oleanolate [CPD:C17148];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
erythrodiol [CPD:C20945];
oleanolic aldehyde [CPD:C20946]
Comment
A cytochrome P-450 (heme-thiolate) protein found in plants. The enzyme is involved in the biosynthesis of oleanane-type triterpenoids, such as ginsenoside Ro. The enzyme from Medicago truncatula (barrel medic) (CYP716A12) can also convert alpha-amyrin and lupeol to ursolic acid and betulinic acid, respectively. The enzyme from Maesa lanceolata (false assegai) (CYP16A75) does not catalyse the reaction to completion, resulting in accumulation of both intermediates.
History
EC 1.14.14.126 created 2015 as EC 1.14.13.201, transferred 2018 to EC 1.14.14.126
Pathway
ec00999  Biosynthesis of various plant secondary metabolites
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K20667  beta-amyrin 28-monooxygenase
Genes
ATH: AT5G36110(CYP716A1) AT5G36130 AT5G36140(CYP716A2)
ALY: 9304531
CRB: 17878597
CSAT: 104719298 104724031 104732576
EUS: EUTSA_v10027740mg
THJ: 104808921
CPAP: 110811366
CIT: 102613788 102620622 102625141 102625960
CIC: CICLE_v10001024mg CICLE_v10010450mg CICLE_v10019890mg CICLE_v10019893mg CICLE_v10030148mg
PVY: 116104854 116107899 116112247 116115260 116119093 116124678 116130216 116130217 116136621 116140662 116140977 116143340 116147033
MINC: 123201025 123201638 123201807 123202365 123205827 123218458 123218589 123218629 123219553 123220675 123226276 123226277 123227278 123228571 123229810 123229811
TCC: 18587560 18589551 18593052 18593053 18593056 18595104 18595548 18595550
GRA: 105767622 105776509 105781233 105781243 105790134
GHI: 107895081 107903232 107919059 107919062 107925135 107926136 107930304 107961323 107963597 121204862
GAB: 108451497 108462699 108465546 108477746 108488461
HSYR: 120124470 120128851 120131435 120133421 120142418 120182578 120183353 120202788
DZI: 111274103 111275451 111278006 111278701 111280632 111280689 111280756 111281159 111301786
EGR: 104435880 104437292 104437293 104441237 104444333 104444335 104448666 104450761 104457239 120293659 120293667 120293668 120294348
GMX: 100801007 100813159 100815640
GSJ: 114413490 114422693 114423706
PVU: PHAVU_002G302100g PHAVU_008G034400g PHAVU_008G034500g
VRA: 106758067 106758467 106767963
VAR: 108322903
VUN: 114176393 114183790
VUM: 124820552 124845221
CCAJ: 109799571
APRC: 113855765 113863293
MTR: 25502252
TPRA: 123915594
CAM: 101507937
PSAT: 127100468 127130215
VVO: 131608116
LJA: Lj0g3v0312269.1(Lj0g3v0312269.1) Lj4g3v3014670.1(Lj4g3v3014670.1)
ADU: 107460466
AIP: 107615408 107630659
AHF: 112701162 112723369 112732385 112790749
LANG: 109333199
PCIN: 129296548 129298412 129301471 129303640 129307971 129322593
QSA: O6P43_003868 O6P43_005319 O6P43_023265 O6P43_023267
FVE: 101291154 101291788 101291806 101292094 101293769 101296436 101299517 101299572 101301540 101302728 101306530 101307150 101315239
RCN: 112164676 112165857 112166483 112166646 112166908 112175390 112177319 112185234 112187334 112195973 112197476 112198001 112198294 112198580 112200323 112201067
PPER: 18774379 18778487 18780496 18780695 18791516
PMUM: 103324310 103325325 103325326 103326766 103326773
PAVI: 110744354 110748403 110759046 110764932 110764933 110764934 110764935 110774275
PDUL: 117620802 117624361 117624362 117624363 117624364 117630226 117630227 117630228
MDM: 103403131 103413895 103422316 103443518 103447994 103450666 103450667 103451601 103453334 108169263
MSYL: 126587952 126589645 126591578 126595747 126597528 126610146 126619690 126621076
PXB: 103929876 103936039 103937151 103942732 103945098 103949490 103954090 103965050
ZJU: 107403276 107403288 107429363 107429366 107433852 112489518 125422327 132799058 132800196
MNT: 21387441 21400536 21408617 21408619
CSAV: 115696903 115696978 115709530
CSV: 101206033
CMO: 103487187
BHJ: 120069984 120070901
MCHA: 111006822 111024635
CMAX: 111485071
CMOS: 111461545
CPEP: 111780629
RCU: 8260767 8262747 8281375 8282082 8282102 8282886 8283916 8283918
JCU: 105628799 105629842 105629863 105636944 105638311
HBR: 110638318 110642272 110643171 110643683 110647242 110648741 110652575 110657288 110657451 110658295 110658320 110672785 110673693
MESC: 110602890 110606971 110608454 110619201 110621545 110625163 110625349 110631281 110631302
POP: 18095771 18104396 18107881 7455277 7465578 7467407 7484042 7487256 7489100 7490471 7490472 7490478 7494429
PEU: 105108453 105108454 105110592 105110597 105111268 105119892 105120887 105120971 105120974 105122459 105130438 105130636 105136784
PALZ: 118029072 118035471 118035472 118040121 118040788 118050537 118052035 118052045 118056475 118056647 118056648
JRE: 108987665 108989511 108989520 108993145 108996978 109000648 109000986
CILL: 122274987 122297779 122298361 122298391 122298465 122299529 122318267
CAVE: 132175679 132176092 132183579 132184488 132185693 132189479 132189482 132190357 132190428 132190436 132190472
QSU: 111984350 111984387 111984580 111994391 111996765 112003765 112007351 112007353 112009785 112012433 112023020
QLO: 115957669 115966342 115967777 115968991 115969220 115969558 115978226 115978829 115981343 115983980 115986079 115986080 115986081 115986083 115986093 115986095 115986097 115987079 115987874 115989783 115989785 115991594 115991595 115992651
TWL: 119982100 119982398 119986646 119989054 119989055 120005290 120006586 120006591 120008479 120014774 120016355
VVI: 100241454 100242305 100242468 100244714 100246675(CYP716A17) 100251813(CYP716A15) 100255183 100260260 100262400 100265713
VRI: 117905739 117907616 117910159 117910160 117913383 117923946 117924581 117924919 117924946 117932528 117932530 117932534 117932600 117932645
SLY: 101251676 101252500 101252702 101263783 101267575
SPEN: 107004210 107010425 107019970 107022868 107025690
SOT: 102579553 102580977 102581212 102581319 102593268 102597003 102603547
SSTN: 125844401 125848263 125852189 125852191 125869360 125872651 125876484 125877297
SDUL: 129874825 129880602 129893123 129898820 129903207 129903413 129903466
CANN: 107845824 107853551 107859002 107870851 107872609 107874833
LBB: 132599628 132615894 132618032 132618881 132622809 132624664 132636946 132640889
NTA: 107773209 107776438 107785337 107785342 107791887 107796228 107797155 107804791 107813374 107819508 107821306 107828908 107832734
NSY: 104211333 104211642 104219137 104219138 104227815 104233149 104234536 104235217
NTO: 104088247 104093962 104096561 104103477 104112260 104112489
NAU: 109209295 109209296 109234271 109236645 109239546 109240000 109244115
INI: 109146947 109164652 109164671 109169662 109179364
ITR: 116012044 116021251 116025198 116032834
SIND: 105159528 105159533 105161986 105167242 105173756 105175834 105177626
OEU: 111365629 111366330 111374946 111374953 111396592 111401849 111401850 111401851 111407310 111409118
EGT: 105951315 105956980 105956981 105956983 105969716 105969717 105970015 105970135 105970583 105970799 105970879 105970880 105970881 105970993 105971315 105974197 105974461 105974503
SSPL: 121750743 121761066 121761221 121769807 121778775 121779379 121779399 121779508 121781093 121781869 121783185 121784991 121785950 121787945 121793371 121801638 121805162
SMIL: 130988356 130988372 131003012 131009691 131010047 131010052 131010056 131010057 131010058 131010141 131010143 131010145 131010146 131010147 131010148 131010152 131017742 131021396
SHIS: 125191080 125192659 125193514 125197414 125203422 125206062 125206064 125206716 125206718 125212910 125216870 125217053 125218485 125224035
APAN: 127249804 127257504 127264669 127264670 127264926 127264966 127265080
HAN: 110886222 110894027 110894028 110894029 110907692 110927675 110940300
ECAD: 122593012 122597632 122597687 122602054 122604278
LSV: 111885055 111887682 111910266 111918815 111918848 111918849
CCAV: 112501106 112505577 112505866 112507837 112516599
DCR: 108192226 108192257 108192646 108194654 108195645 108198064 108202436 108204073 108208468 108216852 108217329 108218261 108225030
CSIN: 114257034 114267580 114269128 114277196 114277247 114278205 114281982 114281988 114285143 114285169 114292526 114292537 114299407 114299408 114304324 114304962 114307165 114310542 114322374
RVL: 131298564 131298796 131302277 131302278 131302279 131302280 131302318 131305857 131305873 131305889 131306031 131307443 131308588 131308613 131313007 131313008 131316863 131316864 131317787 131321743 131322131 131323755 131323783 131324880 131328468 131332743 131335125 131335406 131336305 131336444 131336676
AEW: 130755812 130756802 130761298 130763515 130767376 130771626 130772291 130777959 130782013 130783107 130783116 130786170 130786207
BVG: 104886873 104908688
SOE: 110774665 110783981 110784965 110785568 110785594 110785600
CQI: 110683677 110687936 110710394 110714192 110714258 110715057 110715083 110715088 110715095 110715110 110725244 110725247 110725248 110726788 110730556
ATRI: 130798356 130808690 130813309
MOF: 131151629 131151630 131151632 131165878 131166051 131166194
NNU: 104589205 104590700 104593846 104593852
MING: 122068830 122094731
TSS: 122643208 122648217
PSOM: 113272949 113295481 113324411 113326675 113328770 113329441 113329901 113338734 113362114 113362147
MSIN: 131227071 131250001 131251198
ATR: 105421251 18425136 18441950 18441952 18441953 18441954 18441956
 » show all
Reference
1  [PMID:22039103]
  Authors
Fukushima EO, Seki H, Ohyama K, Ono E, Umemoto N, Mizutani M, Saito K, Muranaka T
  Title
CYP716A subfamily members are multifunctional oxidases in triterpenoid biosynthesis.
  Journal
Plant Cell Physiol 52:2050-61 (2011)
DOI:10.1093/pcp/pcr146
Reference
2  [PMID:24092881]
  Authors
Han JY, Kim MJ, Ban YW, Hwang HS, Choi YE
  Title
The involvement of beta-amyrin 28-oxidase (CYP716A52v2) in oleanane-type ginsenoside biosynthesis in Panax ginseng.
  Journal
Plant Cell Physiol 54:2034-46 (2013)
DOI:10.1093/pcp/pct141
  Sequence
[ag:AFO63032]
Reference
3  [PMID:25578277]
  Authors
Moses T, Pollier J, Faizal A, Apers S, Pieters L, Thevelein JM, Geelen D, Goossens A
  Title
Unraveling the triterpenoid saponin biosynthesis of the African shrub Maesa lanceolata.
  Journal
Mol Plant 8:122-35 (2015)
DOI:10.1016/j.molp.2014.11.004
  Sequence
[ag:AHF22088]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.126
IUBMB Enzyme Nomenclature: 1.14.14.126
ExPASy - ENZYME nomenclature database: 1.14.14.126
BRENDA, the Enzyme Database: 1.14.14.126

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Pathway (7)   
   KEGG PATHWAY (6)   
   KEGG MODULE (1)   
Chemical substance (8)   
   KEGG COMPOUND (8)   
Chemical reaction (8)   
   KEGG REACTION (4)   
   KEGG RCLASS (4)   
Gene (876)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (768)   
   KEGG MGENES (42)   
   RefGene (65)   
Protein sequence (31)   
   UniProt (19)   
   SWISS-PROT (8)   
   RefSeq(pep) (4)   
DNA sequence (29)   
   RefSeq(nuc) (4)   
   GenBank (13)   
   EMBL (12)   
Protein domain (4)   
   InterPro (4)   
All databases (963)   

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