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Ligand (S)-2-amino-5-((R)-1-(carboxymethylamino)-3-(1,4-dihydroxy-3-methylnaphthalen-2-ylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Substrate (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.8.5.7

glutathione + 2-(glutathione-S-yl)-menadiol = glutathione disulfide + menadiol

740055, 740452

-

1.8.5.7

glutathione + 2-(glutathione-S-yl)-menadiol = glutathione disulfide + menadione

740055

-

1.8.5.7

2 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.13.11.52

-

699424

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (5 results)

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Show Turnover Number (5 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.8.5.7

4.6

-

pH 8.0, 23°C

740055

1.8.5.7

4.9

-

pH 8.0, 23°C

740055

1.8.5.7

9.42

-

wild-type, pH 8.0, 20°C

740452

1.8.5.7

13

-

pH 8.0, 23°C

740055

1.8.5.7

14

-

pH 8.0, 23°C

740055

1.8.5.7

5 entries

K_M Value (5 results)

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Show KM Value (5 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.8.5.7

0.003

-

wild-type, pH 8.0, 20°C

740452

1.8.5.7

0.0034

-

pH 8.0, 23°C

740055

1.8.5.7

0.004

-

pH 8.0, 23°C

740055

1.8.5.7

0.0067

-

pH 8.0, 23°C

740055

1.8.5.7

0.017

-

pH 8.0, 23°C

740055

1.8.5.7

5 entries

IC₅₀ Value (1 result)

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Show IC50 Value (1 entry)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.13.11.52

0.00034

-

-

699424

References & Links

Literature References (3)

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Show Reference (3 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

699424

18318466

Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors

2008

Kumar, S.; Malachowski, W.P.; DuHadaway, J.B.; LaLonde, J.M.; Carroll, P.J.; Jaller, D.; Metz, R.; Prendergast, G.C.; Muller, A.J.

J. Med. Chem.

51

1706-1718

740055

22686328

Reduction of benzoquinones to hydroquinones via spontaneous reaction with glutathione and enzymatic reaction by S-glutathionyl-hydroquinone reductases

2012

Lam, L.; Zhang, Z.; Board, P.; Xun, L.

Biochemistry

51

5014-5021

740452

25455804

Glutathionyl-hydroquinone reductases from poplar are plastidial proteins that deglutathionylate both reduced and oxidized glutathionylated quinones

2015

Lallement, P.; Meux, E.; Gualberto, J.; Dumarcay, S.; Favier, F.; Didierjean, C.; Saul, F.; Haouz, A.; Morel-Rouhier, M.; Gelhaye, E.; Rouhier, N.; Hecker, A.

FEBS Lett.

589

37-44

Links to other databases for (S)-2-amino-5-((R)-1-(carboxymethylamino)-3-(1,4-dihydroxy-3-methylnaphthalen-2-ylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid

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Show Links (1 entry)

ChEBI

PubChem