MetaCyc Reaction:

Superclasses: Reactions Classified By Conversion TypeSimple ReactionsChemical Reactions
Reactions Classified By SubstrateSmall-Molecule Reactions

EC Number:

Enzymes and Genes:

Rhodococcus erythropolis DCL14: monocyclic monoterpene ketone monooxygenaseInferred from experiment

The direction shown, i.e. which substrates are on the left and right sides, is in accordance with the direction in which it was curated.

Most BioCyc compounds have been protonated to a reference pH value of 7.3. Please see the PGDB Concepts Guide for more information.

Mass balance status: Balanced.

Direct generic reaction:
a menthone + NADPH + H+ + oxygen → a 7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O (

Enzyme Commission Primary Name: monocyclic monoterpene ketone monooxygenase

Enzyme Commission Synonyms: 1-hydroxy-2-oxolimonene 1,2-monooxygenase, dihydrocarvone 1,2-monooxygenase, MMKMO

Standard Gibbs Free Energy (ΔrG in kcal/mol): -93.320526Inferred by computational analysis [Latendresse13]

Enzyme Commission Summary:
A flavoprotein (FAD). This Baeyer-Villiger monooxygenase enzyme from the Gram-positive bacterium Rhodococcus erythropolis DCL14 has wide substrate specificity, catalysing the lactonization of a large number of monocyclic monoterpene ketones and substituted cyclohexanones [Van00]. Both (1R,4S)- and (1S,4R)-1-hydroxymenth-8-en-2-one are metabolized, with the lactone product spontaneously rearranging to form 3-isopropenyl-6-oxoheptanoate [vanderWerf99].

Citations: [vanderWerf00]

Gene-Reaction Schematic

Gene-Reaction Schematic

Instance reactions of [a menthone + NADPH + H+ + oxygen → a 7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O] (
i6: (-)-menthone + NADPH + H+ + oxygen → (4R,7S)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O (
i7: (+)-menthone + NADPH + H+ + oxygen → (4S,7R)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O (

Instance reactions of [a dihydrocarvone + NADPH + H+ + oxygen → a 4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O] (
i3: (+)-dihydrocarvone + NADPH + H+ + oxygen → (4R,7R)-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O (

i4: (-)-isodihydrocarvone + NADPH + H+ + oxygen → (4S,7R)-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O (

Instance reaction of [an isodihydrocarvone + NADPH + H+ + oxygen → a 6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O] (
i5: (+)-isodihydrocarvone + NADPH + oxygen + H+ → (3S,6R)-6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O (

Instance reactions of [a 1-hydroxymenth-8-en-2-one + NADPH + H+ + oxygen → a 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O] (no EC#):
i1: (1S,4R)-1-hydroxymenth-8-en-2-one + NADPH + H+ + oxygen → (4S)-7-hydroxy-4-isoprenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O (no EC#)

i2: (1R,4S)-1-hydroxymenth-8-en-2-one + NADPH + H+ + oxygen → (4R)-7-hydroxy-4-isoprenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O (no EC#)

Unification Links: KEGG:R08925, Rhea:32431

Relationship Links: BRENDA:EC:, ENZYME:EC:, IUBMB-ExplorEnz:EC:


Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Van00: Van Der Werf MJ (2000). "Purification and characterization of a Baeyer-Villiger mono-oxygenase from Rhodococcus erythropolis DCL14 involved in three different monocyclic monoterpene degradation pathways." Biochem J 347 Pt 3;693-701. PMID: 10769172

vanderWerf00: van der Werf MJ, Boot AM (2000). "Metabolism of carveol and dihydrocarveol in Rhodococcus erythropolis DCL14." Microbiology 146 ( Pt 5);1129-41. PMID: 10832640

vanderWerf99: van der Werf MJ, Swarts HJ, de Bont JA (1999). "Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene." Appl Environ Microbiol 65(5);2092-102. PMID: 10224006

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.5 on Fri Nov 27, 2015, BIOCYC11A.