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Ligand 6-methyluracil

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

2.4.2.3

6-methyluracil + 2-deoxy-D-ribose 1-phosphate = 6-methyl-2'-deoxyuridine + phosphate

759090

4k6o, 3D-view

2.4.2.3

6-methyluracil + alpha-D-ribose 1-phosphate = 6-methyluridine + phosphate

759090

4k6o, 3D-view

2.4.2.3

2 entries

Product in Enzyme-catalyzed Reactions (2 results)

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Show Product (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.2

6-methyluridine + phosphate = 6-methyluracil + alpha-D-ribose 1-phosphate

0

-

2.4.2.3

6-methyluridine + phosphate = 6-methyluracil + alpha-D-ribose 1-phosphate

0

4k6o, 3D-view

Inhibitor in Enzyme-catalyzed Reactions (6 results)

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Show Inhibitors (6 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.11.6

18% inhibition at 5 mM with thymine as substrate

439142

-

1.3.1.14

-

390561

-

2.4.2.3

-

638455

4k6o, 3D-view

2.4.2.3

acts as a pseudosubstrate, molecular docking into the active site, molecular-dynamics simulations of the complex. Repulsion between the hydrophilic hydroxyl group of the active-site residue Thr93 of VchUPh and the hydrophobic methyl group of 6-methyluracil prevents the oxygen atom O4' of the ribose moiety and the phosphate oxygen atom O3P of ribose 1-phosphate from forming hydrogen bonds with OG1_Thr93, which are essential for the enzymatic reaction. This, apparently, renders VchUPh inactive in the enzymatic synthesis of 6-methyluridine from 6-methyluracil

759090

4k6o, 3D-view

2.4.2.3

2 entries

2.4.2.4

competitive, 86% inhibition at 10 mM and 36% inhibition at 1 mM

638455

-

4.2.1.1

inhibition of isozyme hCA I

748316

-

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (1 entry)

EC NUMBER

ENZYME 3D STRUCTURE

2.4.2.3

4k6o, 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

2.4.2.4

1.6

-

-

638455

4.2.1.1

0.05776

-

pH 7.4, temperature not specified in the publication

748316

References & Links

Literature References (5)

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Show Reference (5 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

390561

13610849

Purification and properties of diihydroorotic dehydrogenase

1958

Friedmann, H.C.; Vennesland, B.

J. Biol. Chem.

233

1398-1406

439142

139930

Thymine 7-hydroxylase from Neurospora crassa. Substrate specificity studies

1977

Bankel, L.; Lindstedt, G.; Lindstedt, S.

Biochim. Biophys. Acta

481

431-437

638455

-

Thymidine phosphorylase and uridine phosphorylase of Lactobacillus casei

1988

Avraham, Y.; Yashphe, J.; Grossowicz, N.

FEMS Microbiol. Lett.

56

29-34

748316

28097897

Carbonic anhydrase inhibitory properties of some uracil derivatives

2017

Alper Tuerkoglu, E.; Sentuerk, M.; Supuran, C.T.; Ekinci, D.

J. Enzyme Inhib. Med. Chem.

32

74-77

759090

-

Structural and functional analysis of pyrimidine nucleoside phosphorylases of the NP-I and NP-II families in complexes with 6-methyluracil

2018

Prokofev, I.; Lashkov, A.; Gabdulkhakov, A.; Balaev, V.; Mironov, A.; Betzel, C.; Mikhailov, A.

Crystallogr. Rep.

63

418-427

Links to other databases for 6-methyluracil

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Show Links (1 entry)

ChEBI

PubChem