KEGG   ENZYME: 1.14.14.56Help
Entry
EC 1.14.14.56               Enzyme                                 

Name
1,8-cineole 2-exo-monooxygenase;
CYP3A4
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
BRITE hierarchy
Sysname
1,8-cineole,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (2-exo-hydroxylating)
Reaction(IUBMB)
1,8-cineole + [reduced NADPH---hemoprotein reductase] + O2 = 2-exo-hydroxy-1,8-cineole + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R10076]
Reaction(KEGG)
Substrate
1,8-cineole [CPD:C09844];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
2-exo-hydroxy-1,8-cineole [CPD:C20326];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) protein. The mammalian enzyme, expressed in liver microsomes, performs a variety of oxidation reactions of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. cf. EC 1.14.14.55, quinine 3-monooxygenase, EC 1.14.14.57, taurochenodeoxycholate 6-hydroxylase and EC 1.14.14.73, albendazole monooxygenase (sulfoxide-forming).
History
EC 1.14.14.56 created 2012 as EC 1.14.13.157, transferred 2017 to EC 1.14.14.56, modified 2018
Orthology
K17689  cytochrome P450 family 3 subfamily A polypeptide 4
Genes
HSA: 1576(CYP3A4)
PTR: 463582(CYP3A4)
PPS: 100976899
GGO: 101149513
PON: 100436782
NLE: 100593175
MCC: 678670(CYP3A4)
MCF: 102144258(CYP3A8)
CSAB: 103246766
RRO: 104673585
RBB: 108538168
TUP: 102494214
CFA: 479740(CYP3A4)
 » show all
Taxonomy
Reference
1  [PMID:11159812]
  Authors
Miyazawa M, Shindo M, Shimada T
  Title
Oxidation of 1,8-cineole, the monoterpene cyclic ether originated from eucalyptus polybractea, by cytochrome P450 3A enzymes in rat and human liver microsomes.
  Journal
Drug Metab Dispos 29:200-5 (2001)
  Sequence
[hsa:1576]
Reference
2  [PMID:11547423]
  Authors
Miyazawa M, Shindo M
  Title
Biotransformation of 1,8-cineole by human liver microsomes.
  Journal
Nat Prod Lett 15:49-53 (2001)
DOI:10.1080/10575630108041257
Reference
3  [PMID:11695850]
  Authors
Miyazawa M, Shindo M, Shimada T
  Title
Roles of cytochrome P450 3A enzymes in the 2-hydroxylation of 1,4-cineole, a monoterpene cyclic ether, by rat and human liver microsomes.
  Journal
Xenobiotica 31:713-23 (2001)
DOI:10.1080/00498250110065595
  Sequence
[hsa:1576]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.56
IUBMB Enzyme Nomenclature: 1.14.14.56
ExPASy - ENZYME nomenclature database: 1.14.14.56
BRENDA, the Enzyme Database: 1.14.14.56

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