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Ligand 5-iodouracil

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.2

5-iodo-thymidine + phosphate = 5-iodo-thymine + alpha-D-ribose 1-phosphate

-

-

2.4.2.2

5-iodo-uridine + phosphate = 5-iodo-uracil + alpha-D-ribose 1-phosphate

-

-

2.4.2.2

2 entries

Substrate in Enzyme-catalyzed Reactions (6 results)

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Show Substrate (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.2

5-iodouracil + NADPH = 5-iodo-5,6-dihydrouracil + NADP+

349212, 349211, 349221

1gte, 3D-view

1.3.1.2

5-iodouracil + NADPH = 5-iodo-5,6-dihydrouracil + NADP+

349212, 349211, 349221

1gth, 3D-view

1.3.1.2

2 entries

2.4.2.2

2'-deoxyuridine + 5-iodouracil = 5-iodo-2'-deoxyuridine + uracil

736652

-

2.4.2.6

5-iodouracil + 2'-deoxyadenosine = 5-iodo-2'-deoxyuridine + adenine

758927

-

2.4.2.6

5-iodouracil + 2'-deoxyuridine = 5-iodo-2'-deoxyuridine + uracil

758927

-

2.4.2.6

deoxyadenosine + 5-iodouracil = adenine + deoxy-5-iodouridine

638050

-

2.4.2.6

3 entries

Product in Enzyme-catalyzed Reactions (10 results)

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Show Product (10 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.11.1.10

uracil + I- + H2O2 = 5-iodouracil + H2O

348310

-

1.11.1.18

I- + H2O2 + uracil = 5-iodouracil + H2O

-

-

2.4.2.2

5-iodo-thymidine + phosphate = 5-iodo-thymine + alpha-D-ribose 1-phosphate

-

-

2.4.2.2

5-iodo-uridine + phosphate = 5-iodo-uracil + alpha-D-ribose 1-phosphate

-

-

2.4.2.2

5-iododeoxyuridine + phosphate = 5-iodouracil + 2-deoxy-D-ribose 1-phosphate

-

-

2.4.2.2

5-iodouridine + phosphate = 5-iodouracil + alpha-D-ribose 1-phosphate

-

-

2.4.2.2

4 entries

2.4.2.4

iododeoxyuridine + phosphate = iodouracil + 2-deoxy-D-ribose

-

2wk6, 3D-view

2.4.2.9

5-iodo-UMP + diphosphate = 5-iodouracil + 5-phospho-alpha-D-ribose 1-diphosphate

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-

3.2.2.8

5-iodouridine + H2O = 5-iodouracil + D-ribose

-

-

3.5.4.1

5-iodocytosine + H2O = 5-iodouracil + NH3

-

-

Inhibitor in Enzyme-catalyzed Reactions (14 results)

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Show Inhibitors (14 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.2

mechanism-based inactivator

654897

1gte, 3D-view

1.3.1.2

mechanism-based inactivator

654897

1gth, 3D-view

1.3.1.2

mechanism-based inhibition

654897

1gte, 3D-view

1.3.1.2

mechanism-based inhibition

654897

1gth, 3D-view

1.3.1.2

dithiothreitol and thymine protect against inactivation

349221

1gte, 3D-view

1.3.1.2

dithiothreitol and thymine protect against inactivation

349221

1gth, 3D-view

1.3.1.2

inhibition mechanism

349233

1gte, 3D-view

1.3.1.2

inhibition mechanism

349233

1gth, 3D-view

1.3.1.2

8 entries

1.3.3.7

competitive vs. dihydrouracil

391073

-

2.4.2.30

IC50: 0.071 mM

637997

-

2.4.2.4

His116 directly interacts with the inhibitor via its NE2 group, enzyme binding structure, overview

702064

2wk6, 3D-view

2.6.1.19

84% inhibition at 1 mM

637043

-

2.6.1.22

-

636964

-

2.6.1.40

1 M

637062

-

3D Structure of Enzyme-Ligand-Complex (PDB) (8 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (8 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.3.1.2

1gte, 3D-view

1.3.1.2

1gth, 3D-view

1.3.1.2

1gte, 3D-view

1.3.1.2

1gth, 3D-view

1.3.1.2

1gte, 3D-view

1.3.1.2

1gth, 3D-view

1.3.1.2

6 entries

2.4.2.4

2wk6, 3D-view

3.1.3.5

7pcp, 3D-view

Enzyme Kinetic Parameters

K_i Value (2 results)

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Show KI Value (2 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.3.3.7

0.088

-

-

391073

2.4.2.4

0.48

-

-

702064

IC₅₀ Value (1 result)

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Show IC50 Value (1 entry)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

2.4.2.30

0.071

-

IC50: 0.071 mM

637997

References & Links

Literature References (15)

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Show Reference (15 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

348310

-

Haloperoxidase-catalyzed halogenation of nitrogen-containing aromatic heterocycles represented by nucleic bases

1987

Itoh, N.; Izumi, Y.; Yamada, H.

Biochemistry

26

282-289

349211

13471594

The purification and properties of hydropyrimidine dehydrogenase

1957

Grisolia, S.; Cardoso, S.S.

Biochim. Biophys. Acta

25

430-431

349212

7451435

Purification and properties of dihydrothymine dehydrogenase from rat liver

1981

Shiotani, T.; Weber, G.

J. Biol. Chem.

256

219-224

349221

1939061

Inactivation of dihydropyrimidine dehydrogenase by 5-iodouracil

1991

Porter, D.J.T.; Chestnut, W.G.; Taylor, L.C.E.; Merrill, B.M.; Spector, T.

J. Biol. Chem.

266

19988-19994

349233

11796730

Crystal structure of the productive ternary complex of dihydropyrimidine dehydrogenase with NADPH and 5-iodouracil. Implications for mechanism of inhibition and electron transfer

2002

Dobritzsch, D.; Ricagno, S.; Schneider, G.; Schnackerz, K.D.; Lindqvist, Y.

J. Biol. Chem.

277

13155-13166

391073

-

Partial purification and characterization of dihydrouracil oxidase, a flavoprotein from Rhodotorula glutinis

1986

Owaki, J.; Uzura, K.; Minami, Z.; Kuai, K.

J. Ferment. Technol.

64

205-210

636964

10989446

Purification, properties, and sequencing of aminoisobutyrate aminotransferases from rat liver

2000

Tamaki, N.; Sakata, S.F.; Matsuda, K.

Methods Enzymol.

324

376-389

637043

6688075

Inhibitory effect of 6-azauracil on purified rabbit liver 4-aminobutyrate aminotransferase

1983

Tamaki, N.; Kubo, K.; Aoyama, H.; Funatsuka, A.

J. Biochem.

93

955-959

637062

1633195

Inhibition of D-3-aminoisobutyrate-pyruvate aminotransferase by 5-fluorouracil and alpha-fluoro-beta-alanine

1992

Kaneko, M.; Kontani, Y.; Kikugawa, M.; Tamaki, N.

Biochim. Biophys. Acta

1122

45-49

637997

1530940

Specific inhibitors of poly(ADP-ribose) synthetase and mono(ADP-ribosyl)transferase

1992

Banasik, M.; Komura, H.; Shimoyama, M.; Ueda, K.

J. Biol. Chem.

267

1569-1575

638050

10419637

Assay of nucleoside 2-deoxyribosyltransferase activity with pyruvate kinase/lactate dehydrogenase coupling system

1999

Pistotnik, E.; Sakamoto, H.; Pochet, S.; Namane, A.; Barzu, O.

Anal. Biochem.

271

192-193

654897

15450176

Dihydropyrimidine dehydrogenase: a flavoprotein with four iron-sulfur clusters

2004

Schnackerz, K.D.; Dobritzsch, D.; Lindqvist, Y.; Cook, P.F.

Biochim. Biophys. Acta

1701

61-74

702064

19555658

Structures of native human thymidine phosphorylase and in complex with 5-iodouracil

2009

Mitsiki, E.; Papageorgiou, A.C.; Iyer, S.; Thiyagarajan, N.; Prior, S.H.; Sleep, D.; Finnis, C.; Acharya, K.R.

Biochem. Biophys. Res. Commun.

386

666-670

736652

-

A comparison between immobilized pyrimidine nucleoside phosphorylase from Bacillus subtilis and thymidine phosphorylase from Escherichia coli in the synthesis of 5-substituted pyrimidine 2'-deoxyribonucleosides

2013

Serra, I.; Bavaro, T.; Cecchini, D.; Daly, S.; Albertini, A.; Terreni, M.; Ubiali, D.

J. Mol. Catal. B

95

16-22

758927

32247276

Immobilized enzyme reactors based on nucleoside phosphorylases and 2'-deoxyribosyltransferase for the in-flow synthesis of pharmaceutically relevant nucleoside analogues

2020

Rinaldi, F.; Fernandez-Lucas, J.; de la Fuente, D.; Zheng, C.; Bavaro, T.; Peters, B.; Massolini, G.; Annunziata, F.; Conti, P.; de la Mata, I.; Terreni, M.; Calleri, E.

Biores. Technol.

307

123258

Links to other databases for 5-iodouracil

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Show Links (1 entry)

ChEBI

PubChem