KEGG   ENZYME: 1.14.14.151
Entry
EC 1.14.14.151              Enzyme                                 
Name
premnaspirodiene oxygenase;
HPO;
Hyoscymus muticus premnaspirodiene oxygenase;
CYP71D55
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
(-)-vetispiradiene,[reduced NADPH---hemoprotein reductase]:oxygen 2alpha-oxidoreductase
Reaction(IUBMB)
(-)-vetispiradiene + 2 [reduced NADPH---hemoprotein reductase] + 2 O2 = solavetivone + 2 [oxidized NADPH---hemoprotein reductase] + 3 H2O (overall reaction) [RN:R10073];
(1a) (-)-vetispiradiene + [reduced NADPH---hemoprotein reductase] + O2 = solavetivol + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R09576];
(1b) solavetivol + [reduced NADPH---hemoprotein reductase] + O2 = solavetivone + [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:R09577]
Reaction(KEGG)
R09576 R09577 R10073
Substrate
(-)-vetispiradiene [CPD:C12142];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
solavetivol [CPD:C19711]
Product
solavetivone [CPD:C09737];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
solavetivol [CPD:C19711]
Comment
A cytochrome P-450 (heme-thiolate) protein. The enzyme from the plant Hyoscymus muticus also hydroxylates valencene at C-2 to give the alpha-hydroxy compound, nootkatol, and this is converted into nootkatone. 5-Epiaristolochene and epieremophilene are hydroxylated at C-2 to give a 2beta-hydroxy derivatives that are not oxidized further.
History
EC 1.14.14.151 created 2011 as EC 1.14.13.121, transferred 2018 to EC 1.14.14.151
Pathway
ec00909  Sesquiterpenoid and triterpenoid biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K15472  premnaspirodiene oxygenase
Genes
SLY: 101251277
SPEN: 107017184
SOT: 102603519 102603857(CYP71D4)
SSTN: 125856537 125877776
CANN: 107868116
NTA: 107793096 107814513(CYP71D51)
NSY: 104210979
NAU: 109237629
INI: 109147615 109147616 109147633 109158643 109158692 109189513
ITR: 116001823 116005968 116005969 116005970 116005998 116006057 116006210 116006311 116006362 116006381 116007608 116007666 116007672 116032610
EGT: 105963174 105964617 105975226 105975298 105975392
SSPL: 121743157 121743400 121746146 121750166 121750558 121752413 121754189 121756890 121757276 121757976 121757977 121758417 121759075 121759076 121759079 121759080 121759081 121759086 121759088 121761699 121770564 121771349 121779689 121779749 121783560 121783915 121784616 121811461
ECAD: 122582360 122585186 122607319
 » show all
Reference
1  [PMID:17715131]
  Authors
Takahashi S, Yeo YS, Zhao Y, O'Maille PE, Greenhagen BT, Noel JP, Coates RM, Chappell J
  Title
Functional characterization of premnaspirodiene oxygenase, a cytochrome P450 catalyzing regio- and stereo-specific hydroxylations of diverse sesquiterpene substrates.
  Journal
J Biol Chem 282:31744-54 (2007)
DOI:10.1074/jbc.M703378200
  Sequence
[ag:ABS00393]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.151
IUBMB Enzyme Nomenclature: 1.14.14.151
ExPASy - ENZYME nomenclature database: 1.14.14.151
BRENDA, the Enzyme Database: 1.14.14.151

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Pathway (4)   
   KEGG PATHWAY (4)   
Chemical substance (7)   
   KEGG COMPOUND (7)   
Chemical reaction (6)   
   KEGG REACTION (3)   
   KEGG RCLASS (3)   
Gene (68)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (67)   
Protein sequence (52)   
   UniProt (51)   
   SWISS-PROT (1)   
Protein domain (4)   
   InterPro (4)   
All databases (141)   

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