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Ligand (S)-tetrahydrocolumbamine

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Natural Substrate (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.64

(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-tetrahydroberberine + [oxidized NADPH-hemoprotein reductase] + H2O

728446

-

1.14.19.68

(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O

393237, 393236, 727532

-

1.14.19.73

(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-tetrahydroberberine + [oxidized NADPH-hemoprotein reductase] + H2O

673579

-

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.117

S-Adenosyl-L-methionine + (S)-scoulerine = S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine

0

-

Substrate in Enzyme-catalyzed Reactions (6 results)

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Show Substrate (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.64

(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-tetrahydroberberine + [oxidized NADPH-hemoprotein reductase] + H2O

728446

-

1.14.19.64

(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 = ?

673579

-

1.14.19.68

(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O

393237, 711025, 393236, 727532

-

1.14.19.68

(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 = ?

393237

-

1.14.19.64

2 entries

1.14.19.68

2 entries

1.14.19.73

(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-tetrahydroberberine + [oxidized NADPH-hemoprotein reductase] + H2O

673579

-

2.1.1.117

S-adenosyl-L-methionine + (S)-tetrahydrocolumbamine = S-adenosyl-L-homocysteine + (S)-tetrahydropalmatine

756272

-

Product in Enzyme-catalyzed Reactions (3 results)

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Show Product (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.117

S-Adenosyl-L-methionine + (S)-scoulerine = S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine

0, 15196, 15192

-

2.1.1.117

S-adenosyl-L-methionine + (S)-scoulerine = S-adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine + 2-O-methylscoulerine + tetrahydropalmatine

0

-

2.1.1.117

2 entries

2.1.1.147

S-adenosyl-L-methionine + columbamine + NADPH + H+ = S-adenosyl-L-homocysteine + isocorypalmine + NADP+

0

-

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

3.4.23.46

26.68% inhibition at 0.005 mM

753620

-

Enzyme Kinetic Parameters

K_M Value (3 results)

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Show KM Value (3 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.19.68

0.00463

-

in 100 mM HEPES-NaOH, pH 7.5, at 30°C

727532

1.14.19.68

0.0115

-

canadine synthase in complex with a cytochrome P-450 reductase

393236

1.14.19.68

2.7

-

pH 8.0, 30°C, kcat: 135%

711025

1.14.19.68

3 entries

References & Links

Literature References (10)

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Show Reference (10 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

15192

-

Expression of (S)-scoulerine 9-O-methyltransferase in Coptis japonica plants

1993

Fujiwara, H.; Takeshita, N.; Terano, Y.; Fitchen, J.H.; Tsujita, T.; Katagiri, Y.; Sato, F.; Yamada, Y.

Phytochemistry

34

949-954

15196

24253642

S-Adenosyl-L-methionine:(S)-scoulerine 9-O-methyltransferase, a highly stereo- and regio-specific enzyme in tetrahydroprotoberberine biosynthesis

1985

Muemmler, S.; Rueffer, M.; Nagakura, N.; Zenk, M.H.

Plant Cell Rep.

4

36-39

393236

-

Canadine synthase from Thalictrum tuberosum cell cultures catalyses the formation of the methylenedioxy bridge in berberine synthesis

1994

Rueffer, M.; Zenk, M.H.

Phytochemistry

36

1219-1223

393237

-

New reactions in the protoberberine biosynthetic pathway

1993

Rueffer, M.

Chem. Listy

87

215-217

673579

17250743

Molecular cloning and characterization of methylenedioxy bridge-forming enzymes involved in stylopine biosynthesis in Eschscholzia californica

2007

Ikezawa, N.; Iwasa, K.; Sato, F.

FEBS J.

274

1019-1035

711025

21094631

Characterization of two methylenedioxy bridge-forming cytochrome P450-dependent enzymes of alkaloid formation in the Mexican prickly poppy Argemone mexicana

2011

Diaz Chavez, M.L.; Rolf, M.; Gesell, A.; Kutchan, T.M.

Arch. Biochem. Biophys.

507

186-193

727532

24316226

Cloning and characterization of canadine synthase involved in noscapine biosynthesis in opium poppy

2014

Dang, T.T.; Facchini, P.J.

FEBS Lett.

588

198-204

728446

22421633

Molecular cloning and characterization of a cytochrome P450 in sanguinarine biosynthesis from Eschscholzia californica cells

2013

Takemura, T.; Ikezawa, N.; Iwasa, K.; Sato, F.

Phytochemistry

91

100-108

753620

26779945

Application of BACE1 immobilized enzyme reactor for the characterization of multifunctional alkaloids from Corydalis cava (Fumariaceae) as Alzheimers disease targets

2016

Chlebek, J.; De Simone, A.; Hostalkova, A.; Opletal, L.; Perez, C.; Perez, D.I.; Havlikova, L.; Cahlikova, L.; Andrisano, V.

Fitoterapia

109

241-247

756272

31865477

Identification and characterization of methyltransferases involved in benzylisoquinoline alkaloids biosynthesis from Stephania intermedia

2019

Zhao, W.; Shen, C.; Zhu, J.; Ou, C.; Liu, M.; Dai, W.; Liu, X.; Liu, J.

Biotechnol. Lett.

42

461-469

Links to other databases for (S)-tetrahydrocolumbamine

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Show Links (1 entry)

ChEBI

PubChem