KEGG ORTHOLOGY: K22091

ORTHOLOGY: K22091

Entry

K22091                      KO

Symbol

OMT

Name

7'-O-demethylcephaeline/cephaeline O-methyltransferase [EC:2.1.1.395 2.1.1.396 2.1.1.-]

Pathway

map00950

Isoquinoline alkaloid biosynthesis

map01110

Biosynthesis of secondary metabolites

Reaction

R11681

S-adenosyl-L-methionine:deacetylisoipecoside 6-O-methyltransferase

R11685

S-adenosyl-L-methionine:7'-O-demethylcephaeline 7'-O-methyltransferase

R11686

S-adenosyl-L-methionine:cephaeline 6'-O-methyltransferase

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K22091  OMT; 7'-O-demethylcephaeline/cephaeline O-methyltransferase
Enzymes [BR:ko01000]
2. Transferases
  2.1  Transferring one-carbon groups
   2.1.1  Methyltransferases
    2.1.1.395  7'-O-demethylcephaeline methyltransferase
     K22091  OMT; 7'-O-demethylcephaeline/cephaeline O-methyltransferase
    2.1.1.396  cephaeline 6'-O-methyltransferase
     K22091  OMT; 7'-O-demethylcephaeline/cephaeline O-methyltransferase

Genes

CARB:

113728612 140035835

AG:	BAI79243(OMT1) BAI79244(OMT2) BAI79245(OMT3) BAJ72588(OMT1)

Reference

PMID:20061395

Authors

Nomura T, Kutchan TM

Title

Three new O-methyltransferases are sufficient for all O-methylation reactions of ipecac alkaloid biosynthesis in root culture of Psychotria ipecacuanha.

Journal

J Biol Chem 285:7722-38 (2010)
DOI:10.1074/jbc.M109.086157

Sequence

[ag:BAI79243 BAI79244]

Reference

PMID:21228475

Authors

Cheong BE, Takemura T, Yoshimatsu K, Sato F

Title

Molecular cloning of an O-methyltransferase from adventitious roots of Carapichea ipecacuanha.

Journal

Biosci Biotechnol Biochem 75:107-13 (2011)
DOI:10.1271/bbb.100605

Sequence

[ag:BAJ72588]

LinkDB

ENZYME: 2.1.1.395

Entry

EC 2.1.1.395                Enzyme

Name

7'-O-demethylcephaeline methyltransferase;
IpeOMT2;
CiOMT1

Class

Transferases;
Transferring one-carbon groups;
Methyltransferases

Sysname

S-adenosyl-L-methionine:7'-O-demethylcephaeline 7'-O-methyltransferase

Reaction(IUBMB)

S-adenosyl-L-methionine + 7'-O-demethylcephaeline = S-adenosyl-L-homocysteine + cephaeline [RN:R11685]

Reaction(KEGG)

R11685

Substrate

S-adenosyl-L-methionine [CPD:C00019];
7'-O-demethylcephaeline [CPD:C21584]

Product

S-adenosyl-L-homocysteine [CPD:C00021];
cephaeline [CPD:C09390]

Comment

This activity is the penultimate step in the bionsynthesis of the alkaloid emetine. It is catalysed by two enzymes isolated from the roots of the tropical plant Carapichea ipecacuanha, IpeOMT2 and CiOMT1. The latter also catalyses the activity of EC 2.1.1.396, cephaeline 6'-O-methyltransferase, but with much lower activity.

History

EC 2.1.1.395 created 2024

Pathway

ec00950

Isoquinoline alkaloid biosynthesis

Orthology

K22091

7'-O-demethylcephaeline/cephaeline O-methyltransferase

Genes

CARB:

113728612 140035835

Reference

1 [PMID:20061395]

Authors

Nomura T, Kutchan TM

Title

Three new O-methyltransferases are sufficient for all O-methylation reactions of ipecac alkaloid biosynthesis in root culture of Psychotria ipecacuanha.

Journal

J Biol Chem 285:7722-38 (2010)
DOI:10.1074/jbc.M109.086157

Sequence

[ag:BAI79244]

Reference

2 [PMID:21228475]

Authors

Cheong BE, Takemura T, Yoshimatsu K, Sato F

Title

Molecular cloning of an O-methyltransferase from adventitious roots of Carapichea ipecacuanha.

Journal

Biosci Biotechnol Biochem 75:107-13 (2011)
DOI:10.1271/bbb.100605

Sequence

[ag:BAJ72588]

Other DBs

ExplorEnz - The Enzyme Database:

2.1.1.395

IUBMB Enzyme Nomenclature:

2.1.1.395

ExPASy - ENZYME nomenclature database:

2.1.1.395

BRENDA, the Enzyme Database:

2.1.1.395

LinkDB

REACTION: R11685

Entry

R11685                      Reaction

Name

S-adenosyl-L-methionine:7'-O-demethylcephaeline 7'-O-methyltransferase

Definition

7'-O-Demethylcephaeline + S-Adenosyl-L-methionine <=> Cephaeline + S-Adenosyl-L-homocysteine

Equation

C21584 + C00019 <=> C09390 + C00021

Reaction class

RC00392

C09390_C21584

Enzyme

2.1.1.395

Pathway

rn00950

Isoquinoline alkaloid biosynthesis

rn01110

Biosynthesis of secondary metabolites

Brite

Enzymatic reactions [BR:br08201]
2. Transferase reactions
  2.1  Transferring one-carbon groups
   2.1.1  Methyltransferases
    2.1.1.395
     R11685  7'-O-Demethylcephaeline + S-Adenosyl-L-methionine <=> Cephaeline + S-Adenosyl-L-homocysteine

Orthology

K22091

7'-O-demethylcephaeline/cephaeline O-methyltransferase [EC:2.1.1.395 2.1.1.396 2.1.1.-]

LinkDB

DBGET integrated database retrieval system