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Ligand (6E)-8-oxogeranial

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Natural Substrate (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.122

(6E)-8-oxogeranial + NADH + H+ = (S)-8-oxocitronellyl enol + NAD+

753275

-

1.3.1.122

(6E)-8-oxogeranial + NADPH + H+ = (S)-8-oxocitronellyl enol + NADP+

753275, 754822

-

1.3.1.123

(6E)-8-oxogeranial + NADPH + H+ = (R)-8-oxocitronellal + (S)-8-oxocitronellal + NADP+

757178

-

1.3.1.123

(6E)-8-oxogeranial + NADPH + H+ = (R)-8-oxocitronellyl enol + NADP+

753275

-

1.3.1.123

(6E)-8-oxogeranial + NADPH + H+ = nepetalactol + iridodial + NADP+

757718

-

1.3.1.122

2 entries

1.3.1.123

3 entries

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

1.1.1.324

(6E)-8-hydroxygeraniol + 2 NADP+ = (6E)-8-oxogeranial + 2 NADPH + 2 H+

0

-

Substrate in Enzyme-catalyzed Reactions (7 results)

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Show Substrate (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.122

(6E)-8-oxogeranial + NADH + H+ = (S)-8-oxocitronellyl enol + NAD+

753275

-

1.3.1.122

(6E)-8-oxogeranial + NADPH + H+ = (S)-8-oxocitronellyl enol + NADP+

762544, 753275, 754822

-

1.3.1.122

(6E)-8-oxogeranial + NADPH + H+ = cis-trans-nepetalactone + NADP+

757940

-

1.3.1.122

(6E)-8-oxogeranial + NADPH + H+ = trans-cis-nepetalactone + NADP+

757940

-

1.3.1.123

(6E)-8-oxogeranial + NADPH + H+ = (R)-8-oxocitronellal + (S)-8-oxocitronellal + NADP+

757178

-

1.3.1.123

(6E)-8-oxogeranial + NADPH + H+ = (R)-8-oxocitronellyl enol + NADP+

753275, 758427

-

1.3.1.123

(6E)-8-oxogeranial + NADPH + H+ = nepetalactol + iridodial + NADP+

757718

-

1.3.1.122

4 entries

1.3.1.123

3 entries

Product in Enzyme-catalyzed Reactions (1 result)

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Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.324

(6E)-8-hydroxygeraniol + 2 NADP+ = (6E)-8-oxogeranial + 2 NADPH + 2 H+

0

-

3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (5 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.1.1.145

5mlh, 3D-view

1.3.1.99

5cob, 3D-view

1.3.1.99

5dbi, 3D-view

1.3.1.99

5cob, 3D-view

1.3.1.99

5dbi, 3D-view

1.3.1.99

4 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (15 results)

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Show Turnover Number (15 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.3.1.122

0.002

-

isoform 2, pH 7, 22°C

762544

1.3.1.122

0.006

-

isoform 1, pH 7, 22°C

762544

1.3.1.122

0.025

-

pH 7, 22°C

762544

1.3.1.122

0.064

-

isoform 1, pH 7, 22°C

762544

1.3.1.122

0.066

-

pH 7, 22°C

762544

1.3.1.122

0.155

-

isoform 1, pH 7, 22°C

762544

1.3.1.122

0.321

-

isoform 3, pH 7, 22°C

762544

1.3.1.122

0.6

-

at pH 7.0 and 30°C

757940

1.3.1.122

2.03

-

isoform 3, pH 7, 22°C

762544

1.3.1.122

5.84

-

isoform 2, pH 7, 22°C

762544

1.3.1.122

6.32

-

isoform 2, pH 7, 22°C

762544

1.3.1.123

0.034

-

isoform IS2, at pH 7.0 and 25°C

757718

1.3.1.123

0.11

-

isoform IS1, at pH 7.0 and 25°C

757718

1.3.1.123

0.72

-

with NADPH as cosubstrate, at pH 7.0 and 25°C

757178

1.3.1.123

2.6

-

at pH 7.0, temperature not specified in the publication

758427

1.3.1.122

11 entries

1.3.1.123

4 entries

K_M Value (15 results)

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Show KM Value (15 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.3.1.122

0.0046

-

isoform 1, pH 7, 22°C

762544

1.3.1.122

0.007

-

isoform 2, pH 7, 22°C

762544

1.3.1.122

0.007

-

pH 7, 22°C

762544

1.3.1.122

0.0073

-

at pH 7.0 and 30°C

757940

1.3.1.122

0.0085

-

isoform 2, pH 7, 22°C

762544

1.3.1.122

0.0177

-

isoform 2, pH 7, 22°C

762544

1.3.1.122

0.031

-

pH 7, 22°C

762544

1.3.1.122

0.042

-

isoform 1, pH 7, 22°C

762544

1.3.1.122

0.228

-

isoform 3, pH 7, 22°C

762544

1.3.1.122

0.41

-

isoform 3, pH 7, 22°C

762544

1.3.1.122

3.421

-

isoform 1, pH 7, 22°C

762544

1.3.1.123

0.0011

-

with NADPH as cosubstrate, at pH 7.0 and 25°C

757178

1.3.1.123

0.00729

-

isoform IS1, at pH 7.0 and 25°C

757718

1.3.1.123

0.05437

-

isoform IS2, at pH 7.0 and 25°C

757718

1.3.1.123

0.368

-

at pH 7.0, temperature not specified in the publication

758427

1.3.1.122

11 entries

1.3.1.123

4 entries

References & Links

Literature References (7)

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Show Reference (7 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

753275

30664302

Biocatalytic strategies towards [4+2] cycloadditions

2019

Lichman, B.; O'Connor, S.; Kries, H.

Chemistry

25

6864-6877

754822

30531909

Uncoupled activation and cyclization in catmint reductive terpenoid biosynthesis

2019

Lichman, B.R.; Kamileen, M.O.; Titchiner, G.R.; Saalbach, G.; Stevenson, C.E.M.; Lawson, D.M.; O'Connor, S.E.

Nat. Chem. Biol.

15

71-79

757178

28701463

Inverted stereocontrol of iridoid synthase in snapdragon

2017

Kries, H.; Kellner, F.; Kamileen, M.; O'Connor, S.

J. Biol. Chem.

292

14659-14667

757718

28829394

Cloning and characterization of two iridoid synthase homologs from Swertia mussotii

2017

Xiang, B.; Li, X.; Wang, Y.; Tian, X.; Yang, Z.; Ma, L.; Liu, X.; Wang, Y.

Molecules

22

E1387

757940

29091815

Identification of iridoid synthases from Nepeta species Iridoid cyclization does not determine nepetalactone stereochemistry

2018

Sherden, N.; Lichman, B.; Caputi, L.; Zhao, D.; Kamileen, M.; Buell, C.; O'Connor, S.

Phytochemistry

145

48-56

758427

30287897

A multisubstrate reductase from Plantago major structure-function in the short chain reductase superfamily

2018

Fellows, R.; Russo, C.M.; Silva, C.S.; Lee, S.G.; Jez, J.M.; Chisholm, J.D.; Zubieta, C.; Nanao, M.H.

Sci. Rep.

8

14796

762544

32501002

The Progesterone 5beta-reductase/iridoid synthase family A catalytic reservoir for specialized metabolism across land plants

2020

Nguyen, T.D.; OConnor, S.E.

ACS Chem. Biol.

15

1780-1787

Links to other databases for (6E)-8-oxogeranial

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Show Links (1 entry)

ChEBI

PubChem