KEGG   ORTHOLOGY: K22635
Entry
K22635            Tight     KO                                     
Symbol
CYP76AH3
Name
ferruginol monooxygenase / sugiol synthase [EC:1.14.14.60 1.14.14.65]
Pathway
map00904  Diterpenoid biosynthesis
map01110  Biosynthesis of secondary metabolites
Reaction
R11951  ferruginol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (11-hydroxyferruginol forming)
R11977  ferruginol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (sugiol forming)
R11988  sugiol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (11-hydroxysugiol forming)
R11990  11-hydroxyferruginol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (11-hydroxysugiol forming)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00904 Diterpenoid biosynthesis
    K22635  CYP76AH3; ferruginol monooxygenase / sugiol synthase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K22635  CYP76AH3; ferruginol monooxygenase / sugiol synthase
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
    1.14.14.60  ferruginol monooxygenase
     K22635  CYP76AH3; ferruginol monooxygenase / sugiol synthase
    1.14.14.65  sugiol synthase
     K22635  CYP76AH3; ferruginol monooxygenase / sugiol synthase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP76 family
   K22635  CYP76AH3; ferruginol monooxygenase / sugiol synthase
Genes
SMIL: 131015109 131015114
AG: AMB36496(CYP76AH3)
Reference
PMID:26682704
  Authors
Guo J, Ma X, Cai Y, Ma Y, Zhan Z, Zhou YJ, Liu W, Guan M, Yang J, Cui G, Kang L, Yang L, Shen Y, Tang J, Lin H, Ma X, Jin B, Liu Z, Peters RJ, Zhao ZK, Huang L
  Title
Cytochrome P450 promiscuity leads to a bifurcating biosynthetic pathway for tanshinones.
  Journal
New Phytol 210:525-34 (2016)
DOI:10.1111/nph.13790
  Sequence
[ag:AMB36496]
LinkDB

KEGG   ORTHOLOGY: K22636
Entry
K22636            Tight     KO                                     
Symbol
CYP76AH24
Name
ferruginol synthase / ferruginol monooxygenase [EC:1.14.14.175 1.14.14.60]
Pathway
map00904  Diterpenoid biosynthesis
map01110  Biosynthesis of secondary metabolites
Reaction
R11951  ferruginol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (11-hydroxyferruginol forming)
R12652  abieta-8,11,13-triene,[reduced NADPH---hemoprotein reductase]:oxygen 12-oxidoreductase (ferruginol-forming)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00904 Diterpenoid biosynthesis
    K22636  CYP76AH24; ferruginol synthase / ferruginol monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K22636  CYP76AH24; ferruginol synthase / ferruginol 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
    1.14.14.60  ferruginol monooxygenase
     K22636  CYP76AH24; ferruginol synthase / ferruginol monooxygenase
    1.14.14.175  ferruginol synthase
     K22636  CYP76AH24; ferruginol synthase / ferruginol monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP76 family
   K22636  CYP76AH24; ferruginol synthase / ferruginol monooxygenase
Genes
AG: ALM25796(CYP76AH24)
Reference
PMID:26976595
  Authors
Ignea C, Athanasakoglou A, Ioannou E, Georgantea P, Trikka FA, Loupassaki S, Roussis V, Makris AM, Kampranis SC
  Title
Carnosic acid biosynthesis elucidated by a synthetic biology platform.
  Journal
Proc Natl Acad Sci U S A 113:3681-6 (2016)
DOI:10.1073/pnas.1523787113
  Sequence
[ag:ALM25796]
LinkDB

KEGG   ENZYME: 1.14.14.60
Entry
EC 1.14.14.60               Enzyme                                 
Name
ferruginol monooxygenase;
CYP76AH24;
CYP76AH3
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
ferruginol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (11-hydroxyferruginol-forming)
Reaction(IUBMB)
ferruginol + [reduced NADPH---hemoprotein reductase] + O2 = 11-hydroxyferruginol + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11951]
Reaction(KEGG)
R11951;
(other) R11988
Substrate
ferruginol [CPD:C09092];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
11-hydroxyferruginol [CPD:C21796];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) protein isolated from the plants Salvia pomifera (apple sage) and Salvia miltiorrhiza (danshen). 11-Hydroxyferruginol is a precursor of carnosic acid, a potent antioxidant.
History
EC 1.14.14.60 created 2018
Pathway
ec00904  Diterpenoid biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K22635  ferruginol monooxygenase / sugiol synthase
K22636  ferruginol synthase / ferruginol monooxygenase
Genes
SMIL: 131015109 131015114
Reference
1  [PMID:26976595]
  Authors
Ignea C, Athanasakoglou A, Ioannou E, Georgantea P, Trikka FA, Loupassaki S, Roussis V, Makris AM, Kampranis SC
  Title
Carnosic acid biosynthesis elucidated by a synthetic biology platform.
  Journal
Proc Natl Acad Sci U S A 113:3681-6 (2016)
DOI:10.1073/pnas.1523787113
  Sequence
[ag:ALM25796]
Reference
2  [PMID:27703160]
  Authors
Scheler U, Brandt W, Porzel A, Rothe K, Manzano D, Bozic D, Papaefthimiou D, Balcke GU, Henning A, Lohse S, Marillonnet S, Kanellis AK, Ferrer A, Tissier A
  Title
Elucidation of the biosynthesis of carnosic acid and its reconstitution in yeast.
  Journal
Nat Commun 7:12942 (2016)
DOI:10.1038/ncomms12942
Reference
3  [PMID:26682704]
  Authors
Guo J, Ma X, Cai Y, Ma Y, Zhan Z, Zhou YJ, Liu W, Guan M, Yang J, Cui G, Kang L, Yang L, Shen Y, Tang J, Lin H, Ma X, Jin B, Liu Z, Peters RJ, Zhao ZK, Huang L
  Title
Cytochrome P450 promiscuity leads to a bifurcating biosynthetic pathway for tanshinones.
  Journal
New Phytol 210:525-34 (2016)
DOI:10.1111/nph.13790
  Sequence
[ag:AMB36496]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.60
IUBMB Enzyme Nomenclature: 1.14.14.60
ExPASy - ENZYME nomenclature database: 1.14.14.60
BRENDA, the Enzyme Database: 1.14.14.60
LinkDB

KEGG   REACTION: R11951
Entry
R11951                      Reaction                               
Name
ferruginol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (11-hydroxyferruginol forming)
Definition
Ferruginol + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> 11-Hydroxyferruginol + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
C09092 + C03024 + C00007 <=> C21796 + C03161 + C00001
Reaction class
RC00236  C09092_C21796
Enzyme
1.14.14.60
Pathway
rn00904  Diterpenoid biosynthesis
rn01110  Biosynthesis of secondary metabolites
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
    1.14.14.60
     R11951  Ferruginol + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> 11-Hydroxyferruginol + [Oxidized NADPH---hemoprotein reductase] + H2O
Orthology
K22635  ferruginol monooxygenase / sugiol synthase [EC:1.14.14.60 1.14.14.65]
K22636  ferruginol synthase / ferruginol monooxygenase [EC:1.14.14.175 1.14.14.60]
Other DBs
RHEA: 55431
LinkDB

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