IntEnz

EC 2.1.1.163 - Demethylmenaquinone methyltransferase

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IntEnz Enzyme Nomenclature
EC 2.1.1.163

Names

Accepted name:

demethylmenaquinone methyltransferase

Other names:

S-adenosyl-L-methione—DMK methyltransferase
demethylmenaquinone C-methylase
2-heptaprenyl-1,4-naphthoquinone methyltransferase
2-demethylmenaquinone methyltransferase
S-adenosyl-L-methione:2-demethylmenaquinone methyltransferase

Systematic name:

S-adenosyl-L-methione:demethylmenaquinone methyltransferase

Reactions

26462

6-methoxy-2-all-trans-octaprenyl-1,4-benzoquinone

6-methoxy-2-all-trans-octaprenyl-1,4-benzoquinone

Name origin: UniProt - CHECKED (C)

CHEBI:28423

Formula: C47H70O3
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-methionine

S-adenosyl-L-methionine

Name origin: UniProt - CHECKED (C)

CHEBI:59789

Formula: C15H23N6O5S
Charge: 1

ChEBI compound status: CHECKED (C)

=

3-methyl-6-methoxy-2-all-trans-octaprenyl-1,4-benzoquinone

3-methyl-6-methoxy-2-all-trans-octaprenyl-1,4-benzoquinone

Name origin: UniProt - CHECKED (C)

CHEBI:28636

Formula: C48H72O3
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)

+

S-adenosyl-L-homocysteine

S-adenosyl-L-homocysteine

Name origin: UniProt - CHECKED (C)

CHEBI:57856

Formula: C14H20N6O5S
Charge: 0

ChEBI compound status: CHECKED (C)
26466

a 2-demethylmenaquinone

a 2-demethylmenaquinone

POLYMER:9536

Formula: C10H6O2(C5H8)_n
Charge: (0)(0)_n

ChEBI polymer: CHEBI:28192

+

S-adenosyl-L-methionine

S-adenosyl-L-methionine

Name origin: UniProt - CHECKED (C)

CHEBI:59789

Formula: C15H23N6O5S
Charge: 1

ChEBI compound status: CHECKED (C)

=

a menaquinone

a menaquinone

POLYMER:9537

Formula: C11H8O2(C5H8)_n
Charge: (0)(0)_n

ChEBI polymer: CHEBI:16374

+

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-homocysteine

S-adenosyl-L-homocysteine

Name origin: UniProt - CHECKED (C)

CHEBI:57856

Formula: C14H20N6O5S
Charge: 0

ChEBI compound status: CHECKED (C)
30063

2-demethylmenaquinol-8

2-demethylmenaquinol-8

Name origin: UniProt - CHECKED (C)

CHEBI:61873

Formula: C50H72O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-methionine

S-adenosyl-L-methionine

Name origin: UniProt - CHECKED (C)

CHEBI:59789

Formula: C15H23N6O5S
Charge: 1

ChEBI compound status: CHECKED (C)

=

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

menaquinol-8

menaquinol-8

Name origin: UniProt - CHECKED (C)

CHEBI:61684

Formula: C51H74O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-homocysteine

S-adenosyl-L-homocysteine

Name origin: UniProt - CHECKED (C)

CHEBI:57856

Formula: C14H20N6O5S
Charge: 0

ChEBI compound status: CHECKED (C)
42640 [IUBMB]

a 2-demethylmenaquinol

a 2-demethylmenaquinol

POLYMER:9563

Formula: C10H8O2(C5H8)_n
Charge: (0)(0)_n

ChEBI polymer: CHEBI:55437

+

S-adenosyl-L-methionine

S-adenosyl-L-methionine

Name origin: UniProt - CHECKED (C)

CHEBI:59789

Formula: C15H23N6O5S
Charge: 1

ChEBI compound status: CHECKED (C)

=

a menaquinol

a menaquinol

POLYMER:9539

Formula: C11H10O2(C5H8)_n
Charge: (0)(0)_n

ChEBI polymer: CHEBI:18151

+

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-homocysteine

S-adenosyl-L-homocysteine

Name origin: UniProt - CHECKED (C)

CHEBI:57856

Formula: C14H20N6O5S
Charge: 0

ChEBI compound status: CHECKED (C)
44776

2-demethylmenaquinol-6

2-demethylmenaquinol-6

Name origin: UniProt - CHECKED (C)

CHEBI:84539

Formula: C40H56O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-methionine

S-adenosyl-L-methionine

Name origin: UniProt - CHECKED (C)

CHEBI:59789

Formula: C15H23N6O5S
Charge: 1

ChEBI compound status: CHECKED (C)

=

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

menaquinol-6

menaquinol-6

Name origin: UniProt - CHECKED (C)

CHEBI:84536

Formula: C41H58O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-homocysteine

S-adenosyl-L-homocysteine

Name origin: UniProt - CHECKED (C)

CHEBI:57856

Formula: C14H20N6O5S
Charge: 0

ChEBI compound status: CHECKED (C)
33255

2-demethylmenaquinol-7

2-demethylmenaquinol-7

Name origin: UniProt - CHECKED (C)

CHEBI:64806

Formula: C45H64O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-methionine

S-adenosyl-L-methionine

Name origin: UniProt - CHECKED (C)

CHEBI:59789

Formula: C15H23N6O5S
Charge: 1

ChEBI compound status: CHECKED (C)

=

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

menaquinol-7

menaquinol-7

Name origin: UniProt - CHECKED (C)

CHEBI:64834

Formula: C46H66O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-homocysteine

S-adenosyl-L-homocysteine

Name origin: UniProt - CHECKED (C)

CHEBI:57856

Formula: C14H20N6O5S
Charge: 0

ChEBI compound status: CHECKED (C)
44780

2-demethylmenaquinol-9

2-demethylmenaquinol-9

Name origin: UniProt - CHECKED (C)

CHEBI:84542

Formula: C55H80O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-methionine

S-adenosyl-L-methionine

Name origin: UniProt - CHECKED (C)

CHEBI:59789

Formula: C15H23N6O5S
Charge: 1

ChEBI compound status: CHECKED (C)

=

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

menaquinol-9

menaquinol-9

Name origin: UniProt - CHECKED (C)

CHEBI:84541

Formula: C56H82O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-homocysteine

S-adenosyl-L-homocysteine

Name origin: UniProt - CHECKED (C)

CHEBI:57856

Formula: C14H20N6O5S
Charge: 0

ChEBI compound status: CHECKED (C)
44784

2-demethylmenaquinol-10

2-demethylmenaquinol-10

Name origin: UniProt - CHECKED (C)

CHEBI:84546

Formula: C60H88O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-methionine

S-adenosyl-L-methionine

Name origin: UniProt - CHECKED (C)

CHEBI:59789

Formula: C15H23N6O5S
Charge: 1

ChEBI compound status: CHECKED (C)

=

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

menaquinol-10

menaquinol-10

Name origin: UniProt - CHECKED (C)

CHEBI:84544

Formula: C61H90O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-homocysteine

S-adenosyl-L-homocysteine

Name origin: UniProt - CHECKED (C)

CHEBI:57856

Formula: C14H20N6O5S
Charge: 0

ChEBI compound status: CHECKED (C)
44788

2-demethylmenaquinol-11

2-demethylmenaquinol-11

Name origin: UniProt - CHECKED (C)

CHEBI:84548

Formula: C65H96O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-methionine

S-adenosyl-L-methionine

Name origin: UniProt - CHECKED (C)

CHEBI:59789

Formula: C15H23N6O5S
Charge: 1

ChEBI compound status: CHECKED (C)

=

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

menaquinol-11

menaquinol-11

Name origin: UniProt - CHECKED (C)

CHEBI:84547

Formula: C66H98O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-homocysteine

S-adenosyl-L-homocysteine

Name origin: UniProt - CHECKED (C)

CHEBI:57856

Formula: C14H20N6O5S
Charge: 0

ChEBI compound status: CHECKED (C)
44792

2-demethylmenaquinol-12

2-demethylmenaquinol-12

Name origin: UniProt - CHECKED (C)

CHEBI:84551

Formula: C70H104O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-methionine

S-adenosyl-L-methionine

Name origin: UniProt - CHECKED (C)

CHEBI:59789

Formula: C15H23N6O5S
Charge: 1

ChEBI compound status: CHECKED (C)

=

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

menaquinol-12

menaquinol-12

Name origin: UniProt - CHECKED (C)

CHEBI:84550

Formula: C71H106O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-homocysteine

S-adenosyl-L-homocysteine

Name origin: UniProt - CHECKED (C)

CHEBI:57856

Formula: C14H20N6O5S
Charge: 0

ChEBI compound status: CHECKED (C)
44796

2-demethylmenaquinol-13

2-demethylmenaquinol-13

Name origin: UniProt - CHECKED (C)

CHEBI:84553

Formula: C75H112O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-methionine

S-adenosyl-L-methionine

Name origin: UniProt - CHECKED (C)

CHEBI:59789

Formula: C15H23N6O5S
Charge: 1

ChEBI compound status: CHECKED (C)

=

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

menaquinol-13

menaquinol-13

Name origin: UniProt - CHECKED (C)

CHEBI:84552

Formula: C76H114O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

S-adenosyl-L-homocysteine

S-adenosyl-L-homocysteine

Name origin: UniProt - CHECKED (C)

CHEBI:57856

Formula: C14H20N6O5S
Charge: 0

ChEBI compound status: CHECKED (C)

Comments:

The enzyme catalyses the last step in menaquinone biosynthesis. It is able to accept substrates with varying polyprenyl side chain length (the chain length is determined by polyprenyl diphosphate synthase) [1]. The enzyme from Escherichia coli also catalyses the conversion of 2-methoxy-6-octaprenyl-1,4-benzoquinone to 5-methoxy-2-methyl-3-octaprenyl-1,4-benzoquinone during the biosynthesis of ubiquinone [4]. The enzyme probably acts on menaquinol rather than menaquinone.

Links to other databases

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

Protein domains and families: PROSITE:PDOC00911

Structural data: CSA , EC2PDB

Gene Ontology: GO:0102955

UniProtKB/Swiss-Prot: (387) [show] [UniProt]

References

Koike-Takeshita, A., Koyama, T., Ogura, K.

Identification of a novel gene cluster participating in menaquinone (vitamin K₂) biosynthesis. Cloning and sequence determination of the 2-heptaprenyl-1,4-naphthoquinone methyltransferase gene of Bacillus stearothermophilus.

J. Biol. Chem. 272: 12380-12383 (1997). [PMID: 9139683]
Wissenbach, U., Ternes, D., Unden, G.

An Escherichia coli mutant containing only demethylmenaquinone, but no menaquinone: effects on fumarate, dimethylsulfoxide, trimethylamine N-oxide and nitrate respiration.

Arch. Microbiol. 158: 68-73 (1992). [PMID: 1444716]
Catala, F., Azerad, R., Lederer, E.

Sur les propriétés de la desméthylménaquinone C-méthylase de Mycobacterium phlei

Int. Z. Vitaminforsch. 40: 363-373 (1970). [PMID: 5450997]
Lee, P. T., Hsu, A. Y., Ha, H. T., Clarke, C. F.

A C-methyltransferase involved in both ubiquinone and menaquinone biosynthesis: isolation and identification of the Escherichia coli ubiE gene.

J. Bacteriol. 179: 1748-1754 (1997). [PMID: 9045837]

[EC 2.1.1.163 created 2009]

EC 2 - Transferases