IntEnz - EC 1.14.13.105

EC 1 - Oxidoreductases

EC 1.14 - Acting on paired donors, with incorporation or reduction of molecular oxygen. The oxygen incorporated need not be derived from O₂

EC 1.14.13 - With NADH or NADPH as one donor, and incorporation of one atom of oxygen

EC 1.14.13.105 - Monocyclic monoterpene ketone monooxygenase

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IntEnz Enzyme Nomenclature
EC 1.14.13.105

Names

Accepted name:

monocyclic monoterpene ketone monooxygenase

Other names:

1-hydroxy-2-oxolimonene 1,2-monooxygenase
dihydrocarvone 1,2-monooxygenase
MMKMO

Systematic name:

(−)-menthone,NADPH:oxygen oxidoreductase

Reactions

32431 [IUBMB]

(1R,4S)-menthone

(1R,4S)-menthone

Name origin: UniProt - CHECKED (C)

CHEBI:15410

Formula: C10H18O
Charge: 0

ChEBI compound status: CHECKED (C)

+

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

NADPH

NADPH

Name origin: UniProt - CHECKED (C)

CHEBI:57783

Formula: C21H26N7O17P3
Charge: -4

ChEBI compound status: CHECKED (C)

+

O₂

O2

Name origin: UniProt - CHECKED (C)

CHEBI:15379

Formula: O2
Charge: 0

ChEBI compound status: CHECKED (C)

=

(4R,7S)-7-isopropyl-4-methyloxepan-2-one

(4R,7S)-7-isopropyl-4-methyloxepan-2-one

Name origin: UniProt - CHECKED (C)

CHEBI:50250

Formula: C10H18O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

H₂O

H2O

Name origin: UniProt - CHECKED (C)

CHEBI:15377

Formula: H2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

NADP⁺

NADP(+)

Name origin: UniProt - CHECKED (C)

CHEBI:58349

Formula: C21H25N7O17P3
Charge: -3

ChEBI compound status: CHECKED (C)
32435 [IUBMB]

dihydrocarvone

dihydrocarvone

Name origin: UniProt - CHECKED (C)

CHEBI:23733

Formula: C10H16O
Charge: 0

ChEBI compound status: CHECKED (C)

+

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

NADPH

NADPH

Name origin: UniProt - CHECKED (C)

CHEBI:57783

Formula: C21H26N7O17P3
Charge: -4

ChEBI compound status: CHECKED (C)

+

O₂

O2

Name origin: UniProt - CHECKED (C)

CHEBI:15379

Formula: O2
Charge: 0

ChEBI compound status: CHECKED (C)

=

4-isopropenyl-7-methyloxepan-2-one

4-isopropenyl-7-methyloxepan-2-one

Name origin: UniProt - CHECKED (C)

CHEBI:50238

Formula: C10H16O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

H₂O

H2O

Name origin: UniProt - CHECKED (C)

CHEBI:15377

Formula: H2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

NADP⁺

NADP(+)

Name origin: UniProt - CHECKED (C)

CHEBI:58349

Formula: C21H25N7O17P3
Charge: -3

ChEBI compound status: CHECKED (C)
32583 [IUBMB]

dihydrocarvone

dihydrocarvone

Name origin: UniProt - CHECKED (C)

CHEBI:23733

Formula: C10H16O
Charge: 0

ChEBI compound status: CHECKED (C)

+

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

NADPH

NADPH

Name origin: UniProt - CHECKED (C)

CHEBI:57783

Formula: C21H26N7O17P3
Charge: -4

ChEBI compound status: CHECKED (C)

+

O₂

O2

Name origin: UniProt - CHECKED (C)

CHEBI:15379

Formula: O2
Charge: 0

ChEBI compound status: CHECKED (C)

=

6-isopropenyl-3-methyloxepan-2-one

6-isopropenyl-3-methyloxepan-2-one

Name origin: UniProt - CHECKED (C)

CHEBI:64229

Formula: C10H16O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

H₂O

H2O

Name origin: UniProt - CHECKED (C)

CHEBI:15377

Formula: H2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

NADP⁺

NADP(+)

Name origin: UniProt - CHECKED (C)

CHEBI:58349

Formula: C21H25N7O17P3
Charge: -3

ChEBI compound status: CHECKED (C)
55004 [IUBMB]

1-hydroxylimonen-2-one

1-hydroxylimonen-2-one

Name origin: UniProt - CHECKED (C)

CHEBI:50246

Formula: C10H16O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

NADPH

NADPH

Name origin: UniProt - CHECKED (C)

CHEBI:57783

Formula: C21H26N7O17P3
Charge: -4

ChEBI compound status: CHECKED (C)

+

O₂

O2

Name origin: UniProt - CHECKED (C)

CHEBI:15379

Formula: O2
Charge: 0

ChEBI compound status: CHECKED (C)

=

3-isopropenyl-6-oxoheptanoate

3-isopropenyl-6-oxoheptanoate

Name origin: UniProt - CHECKED (C)

CHEBI:64234

Formula: C10H15O3
Charge: -1

ChEBI compound status: CHECKED (C)

+

H₂O

H2O

Name origin: UniProt - CHECKED (C)

CHEBI:15377

Formula: H2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

NADP⁺

NADP(+)

Name origin: UniProt - CHECKED (C)

CHEBI:58349

Formula: C21H25N7O17P3
Charge: -3

ChEBI compound status: CHECKED (C)

Cofactor

Comments:

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 [2]. 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 [1].

Links to other databases

Enzymes and pathways: NC-IUBMB , BRENDA , DIAGRAM , DIAGRAM , DIAGRAM , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UniPathway

Structural data: CSA , EC2PDB

UniProtKB/Swiss-Prot:

P82679

BVMO_RHOER

References

van der Werf, M.J., Swarts, H.J. and de Bont, J.A.M.

Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene.

Appl. Environ. Microbiol. 65: 2092-2102 (1999). [PMID: 10224006]
Van Der Werf, M.J.

Purification and characterization of a Baeyer-Villiger mono-oxygenase from Rhodococcus erythropolis DCL14 involved in three different monocyclic monoterpene degradation pathways.

Biochem. J. 347: 693-701 (2000). [PMID: 10769172]
van der Werf, M.J. and Boot, A.M.

Metabolism of carveol and dihydrocarveol in Rhodococcus erythropolis DCL14.

Microbiology 146: 1129-1141 (2000). [PMID: 10832640]

[EC 1.14.13.105 created 2008]