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Ligand vomilenine

Basic Ligand Information

Molecular Structure

Related pathways

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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

1.5.1.32

vomilenine + NADPH + H+ = 1,2-dihydrovomilenine + NADP+

769647, 775227

-

1.5.1.32

vomilenine + NADPH = 2-beta-(R)-1,2-dihydrovomilenine + NADP+

437752

-

1.5.1.32

2 entries

2.4.1.219

UDP-glucose + vomilenine = UDP + raucaffricine

488935, 488936, 488934, 488937, 488938

-

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

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.104

vinorine + [reduced NADPH-hemoprotein reductase] + O2 = vomilenine + [oxidized NADPH-hemoprotein reductase] + H2O

440250, -

-

1.5.1.32

1,2-dihydrovomilenine + NADP+ = vomilenine + NADPH + H+

-

-

3.2.1.125

raucaffricine + H2O = D-glucose + vomilenine

488937, 488938, -

-

Substrate in Enzyme-catalyzed Reactions (4 results)

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Show Substrate (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.73

vomilenine + NADPH + H+ = ?

774657

-

1.5.1.32

vomilenine + NADPH + H+ = 1,2-dihydrovomilenine + NADP+

769647, 775227

-

1.5.1.32

vomilenine + NADPH = 2-beta-(R)-1,2-dihydrovomilenine + NADP+

437752

-

1.5.1.32

2 entries

2.4.1.219

UDP-glucose + vomilenine = UDP + raucaffricine

488935, 488936, 488934, 488937, 488938

-

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.104

vinorine + [reduced NADPH-hemoprotein reductase] + O2 = vomilenine + [oxidized NADPH-hemoprotein reductase] + H2O

440250, -

-

1.5.1.32

1,2-dihydrovomilenine + NADP+ = vomilenine + NADPH + H+

-

-

3.2.1.125

raucaffricine + H2O = D-glucose + vomilenine

488937, 488938, -

-

3.2.1.125

raucaffricine + H2O = vomilenine + D-glucose

488934

-

3.2.1.125

2 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (1 result)

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Show Turnover Number (1 entry)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.3.1.73

0.2

-

N-terminally truncated enzyme, at pH 7.5 and 30°C

774657

K_M Value (2 results)

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Show KM Value (2 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.3.1.73

1.089

-

N-terminally truncated enzyme, at pH 7.5 and 30°C

774657

2.4.1.219

0.04

-

-

488935

References & Links

Literature References (10)

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Show Reference (10 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

437752

11937349

Vomilenine reductase - a novel enzyme catalyzing a crucial step in the biosynthesis of the therapeutically applied antiarrhythmic alkaloid ojmaline

2002

von Schuhmann, G.; Gao, S.; Stöckigt, J.

Bioorg. Med. Chem.

10

1913-1928

440250

-

Enzymic biosynthesis of vomilenine, a key intermediate of the ajmaline pathway, catalyzed by a novel cytochrome P450-dependent enzyme from plant cell cultures of Rauwolfia serpentina

1995

Falkenhagen, H.; Stoeckigt, J.

Z. Naturforsch. C

50

45-53

488934

-

Partial purification and characterization of raucaffricine beta-D-glucosidase from plant cell-suspension cultures of Rauwolfia serpentina Benth

1986

Schuebel, H.; Stoeckigt, J.; Feicht, R.; Simon, H.

Helv. Chim. Acta

69

538-547

488935

-

Enzymatic formation of Raucaffricine, the major indole alkaloid of Rauwolfia serpentina cell-suspension cultures

1991

Ruyter, C.M.; Stoeckigt, J.H.H.

Helv. Chim. Acta

74

1707-1712

488936

-

Isolation and characterization of an UDPG-dependent glucosyltransferase activity from Rauwolfia serpentina Benth. cell suspension cultures

1994

Lutterbach, R.; Ruyter, C.M.; Stoeckigt, J.

Can. J. Chem.

72

51-55

488937

10234858

Purification, partial amino acid sequence and structure of the product of raucaffricine-O-beta-D-glucosidase from plant cell cultures of Rauwolfia serpentina

1999

Warzecha, H.; Obitz, P.; Stockigt, J.

Phytochemistry

50

1099-1109

488938

10975500

Molecular cloning and functional bacterial expression of a plant glucosidase specifically involved in alkaloid biosynthesis

2000

Warzecha, H.; Gerasimenko, I.; Kutchan, T.M.; Stockigt, J.

Phytochemistry

54

657-666

769647

11937349

Vomilenine reductase - a novel enzyme catalyzing a crucial step in the biosynthesis of the therapeutically applied antiarrhythmic alkaloid ajmaline

2002

von Schumann, G.; Gao, S.; Stoeckigt, J.

Bioorg. Med. Chem.

10

1913-1918

774657

38212296

De novo biosynthesis of antiarrhythmic alkaloid ajmaline

2024

Guo, J.; Gao, D.; Lian, J.; Qu, Y.

Nat. Commun.

15

457

775227

26715562

A novel cinnamyl alcohol dehydrogenase (CAD)-like reductase contributes to the structural diversity of monoterpenoid indole alkaloids in Rauvolfia

2016

Geissler, M.; Burghard, M.; Volk, J.; Staniek, A.; Warzecha, H.

Planta

243

813-824

Links to other databases for vomilenine

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Show Links (1 entry)