KEGG   ORTHOLOGY: K21120
Entry
K21120            Tight     KO                                     
Symbol
P450cin, CYP176A1
Name
1,8-cineole 2-endo-monooxygenase [EC:1.14.14.133]
Pathway
map00902  Monoterpenoid biosynthesis
map01110  Biosynthesis of secondary metabolites
Reaction
R08784  1,8-cineole,[reduced flavodoxin]:oxygen oxidoreductase (2-endo-hydroxylating)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00902 Monoterpenoid biosynthesis
    K21120  P450cin, CYP176A1; 1,8-cineole 2-endo-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K21120  P450cin, CYP176A1; 1,8-cineole 2-endo-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
    1.14.14.133  1,8-cineole 2-endo-monooxygenase
     K21120  P450cin, CYP176A1; 1,8-cineole 2-endo-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, bacteria type
  CYP176 family
   K21120  P450cin, CYP176A1; 1,8-cineole 2-endo-monooxygenase
Other DBs
COG: COG2124
Genes
ROZ: CBI38_14805
RHZP: HYG77_00630
AG: AAL57614(CYP176A1)
Reference
PMID:12016226
  Authors
Hawkes DB, Adams GW, Burlingame AL, Ortiz de Montellano PR, De Voss JJ
  Title
Cytochrome P450(cin) (CYP176A), isolation, expression, and characterization.
  Journal
J Biol Chem 277:27725-32 (2002)
DOI:10.1074/jbc.M203382200
  Sequence
[ag:AAL57614]
LinkDB

KEGG   ENZYME: 1.14.14.133
Entry
EC 1.14.14.133              Enzyme                                 
Name
1,8-cineole 2-endo-monooxygenase;
P450cin;
CYP176A;
CYP176A1
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
1,8-cineole,[reduced flavodoxin]:oxygen oxidoreductase (2-endo-hydroxylating)
Reaction(IUBMB)
1,8-cineole + [reduced flavodoxin] + O2 = 2-endo-hydroxy-1,8-cineole + [oxidized flavodoxin] + H2O [RN:R08784]
Reaction(KEGG)
R08784
Substrate
1,8-cineole [CPD:C09844];
reduced flavodoxin [CPD:C02745];
O2 [CPD:C00007]
Product
2-endo-hydroxy-1,8-cineole [CPD:C03092];
oxidized flavodoxin [CPD:C02869];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) protein that uses a flavodoxin-like redox partner to reduce the heme iron. Isolated from the bacterium Citrobacter braakii, which can use 1,8-cineole as the sole source of carbon.
History
EC 1.14.14.133 created 2012 as EC 1.14.13.156, transferred 2018 to EC 1.14.14.133
Pathway
ec00902  Monoterpenoid biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K21120  1,8-cineole 2-endo-monooxygenase
Genes
ROZ: CBI38_14805
RHZP: HYG77_00630
Reference
1  [PMID:12016226]
  Authors
Hawkes DB, Adams GW, Burlingame AL, Ortiz de Montellano PR, De Voss JJ
  Title
Cytochrome P450(cin) (CYP176A), isolation, expression, and characterization.
  Journal
J Biol Chem 277:27725-32 (2002)
DOI:10.1074/jbc.M203382200
  Sequence
[ag:AAL57614]
Reference
2  [PMID:15260491]
  Authors
Meharenna YT, Li H, Hawkes DB, Pearson AG, De Voss J, Poulos TL
  Title
Crystal structure of P450cin in a complex with its substrate, 1,8-cineole, a close structural homologue to D-camphor, the substrate for P450cam.
  Journal
Biochemistry 43:9487-94 (2004)
DOI:10.1021/bi049293p
  Sequence
[ag:AAL57614]
Reference
3  [PMID:17606612]
  Authors
Kimmich N, Das A, Sevrioukova I, Meharenna Y, Sligar SG, Poulos TL
  Title
Electron transfer between cytochrome P450cin and its FMN-containing redox partner, cindoxin.
  Journal
J Biol Chem 282:27006-11 (2007)
DOI:10.1074/jbc.M703790200
Reference
4  [PMID:18270198]
  Authors
Meharenna YT, Slessor KE, Cavaignac SM, Poulos TL, De Voss JJ
  Title
The critical role of substrate-protein hydrogen bonding in the control of regioselective hydroxylation in p450cin.
  Journal
J Biol Chem 283:10804-12 (2008)
DOI:10.1074/jbc.M709722200
  Sequence
[ag:AAL57614]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.133
IUBMB Enzyme Nomenclature: 1.14.14.133
ExPASy - ENZYME nomenclature database: 1.14.14.133
BRENDA, the Enzyme Database: 1.14.14.133
LinkDB

KEGG   REACTION: R08784
Entry
R08784                      Reaction                               
Name
1,8-cineole,[reduced flavodoxin]:oxygen oxidoreductase (2-endo-hydroxylating)
Definition
1,8-Cineole + Reduced flavodoxin + Oxygen <=> 6-endo-Hydroxycineole + Oxidized flavodoxin + H2O
Equation
C09844 + C02745 + C00007 <=> C03092 + C02869 + C00001
Reaction class
RC01218  C03092_C09844
Enzyme
1.14.14.133
Pathway
rn00902  Monoterpenoid 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
    1.14.14.133
     R08784  1,8-Cineole + Reduced flavodoxin + Oxygen <=> 6-endo-Hydroxycineole + Oxidized flavodoxin + H2O
Orthology
K21120  1,8-cineole 2-endo-monooxygenase [EC:1.14.14.133]
Reference
1  [PMID:1368150]
  Authors
Trudgill PW
  Title
Microbial metabolism of monoterpenes--recent developments.
  Journal
Biodegradation 1:93-105 (1990)
DOI:10.1007/BF00058829
Other DBs
RHEA: 32902
LinkDB

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