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Ligand 2-deoxy-alpha-D-ribose 1-phosphate

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

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Show Natural Substrate (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.2

thymine + 2-deoxy-alpha-D-ribose 1-phosphate = thymidine + phosphate

760726

-

2.4.2.4

5-fluorouracil + 2-deoxy-alpha-D-ribose 1-phosphate = 5-fluoro-2'-deoxyuridine + phosphate

705495

-

2.4.2.4

thymine + 2-deoxy-alpha-D-ribose 1-phosphate = thymidine + phosphate

758892, 759084, 760181, 758893, 758894, 758895, 758897, 758899, 758902, 759143, 760047

-

2.4.2.4

uracil + 2-deoxy-alpha-D-ribose 1-phosphate = 2'-deoxyuridine + phosphate

758899

-

2.4.2.4

3 entries

In Vivo Product in Enzyme-catalyzed Reactions (8 results)

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Show Natural Product (8 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.1

2'-deoxyguanosine + phosphate = guanine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.1

6-mercaptopurine-2'-deoxyriboside + phosphate = 6-mercaptopurine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.1

purine deoxyribonucleoside + phosphate = purine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.2

2'-deoxythymidine + phosphate = thymine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.2

2'-deoxyuridine + phosphate = uracil + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.2

thymidine + phosphate = thymine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.1

3 entries

2.4.2.2

3 entries

2.4.2.3

thymidine + phosphate = thymine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.4

thymidine + phosphate = thymine + 2-deoxy-alpha-D-ribose 1-phosphate

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

2.4.2.1

hypoxanthine + alpha-D-deoxyribose 1-phosphate = deoxyinosine + phosphate

489678

-

2.4.2.2

thymine + 2-deoxy-alpha-D-ribose 1-phosphate = thymidine + phosphate

760726

-

2.4.2.4

5-fluorouracil + 2-deoxy-alpha-D-ribose 1-phosphate = 5-fluoro-2'-deoxyuridine + phosphate

705495

-

2.4.2.4

thymine + 2-deoxy-alpha-D-ribose 1-phosphate = thymidine + phosphate

758892, 759084, 759338, 760181, 758893, 758894, 758895, 758897, 758899, 758902, 759143, 760047

-

2.4.2.4

uracil + 2-deoxy-alpha-D-ribose 1-phosphate = 2'-deoxyuridine + phosphate

758899

-

2.7.1.212

2-deoxy-alpha-D-ribose 1-phosphate + ADP = 2-deoxy-alpha-D-ribose 1,5-bisphosphate + AMP

734747

-

2.7.1.212

ADP + 2-deoxy-alpha-D-ribose-1-phosphate = AMP + 2-deoxy-alpha-D-ribose 1,5-bisphosphate

734747

-

2.4.2.4

3 entries

2.7.1.212

2 entries

Product in Enzyme-catalyzed Reactions (28 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.1

2'-deoxyadenosine + phosphate = 2-deoxy-alpha-D-ribose 1-phosphate + adenine

0

-

2.4.2.1

2'-deoxyadenosine + phosphate = adenine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.1

2'-deoxyguanosine + phosphate = guanine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.1

2'-deoxyinosine + phosphate = 2-deoxy-alpha-D-ribose 1-phosphate + hypoxanthine

0

-

2.4.2.1

2'-deoxyinosine + phosphate = hypoxanthine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.1

6-mercaptopurine-2'-deoxyriboside + phosphate = 6-mercaptopurine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.1

9-beta-D-(2-deoxyribofuranosyl)-6-methylthiopurine + phosphate = 6-methylthiopurine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.1

deoxyinosine + phosphate = hypoxanthine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.1

purine deoxyribonucleoside + phosphate = purine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.1

2'-deoxyguanosine + phosphate = guanine + alpha-D-2-deoxyribose 1-phosphate

0

-

2.4.2.1

2'-deoxyinosine + phosphate = alpha-D-2-deoxyribose 1-phosphate + hypoxanthine

0

-

2.4.2.1

deoxyguanosine + phosphate = guanine + alpha-D-deoxyribose 1-phosphate

0

-

2.4.2.1

deoxyinosine + phosphate = hypoxanthine + alpha-D-deoxyribose 1-phosphate

0

-

2.4.2.2

2'-deoxythymidine + phosphate = thymine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.2

2'-deoxyuridine + phosphate = uracil + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.2

5-fluoro-2'-deoxyuridine + phosphate = 5-fluorouracil + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.2

5-trifluorothymidine + phosphate = 5-trifluorothymine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.2

thymidine + phosphate = thymine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.2

5'-deoxy-5-fluorouridine + phosphate = 5-fluorouracil + alpha-D-deoxyribose 1-phosphate

0

-

2.4.2.2

thymidine + phosphate = thymine + alpha-D-deoxyribose 1-phosphate

0

-

2.4.2.3

5-fluoro-2'-deoxyuridine + phosphate = 5-fluorouracil + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.3

deoxyuridine + phosphate = uracil + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.3

thymidine + phosphate = thymine + 2-deoxy-alpha-D-ribose 1-phosphate

0, 638508

-

2.4.2.4

2'-deoxy-5-nitrouridine + phosphate = 5-nitrouracil + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.4

2'-deoxyuridine + phosphate = uracil + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.4

5-fluoro-2'-deoxyuridine + phosphate = 5-fluorouracil + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.4

thymidine + phosphate = thymine + 2-deoxy-alpha-D-ribose 1-phosphate

0

-

2.4.2.4

thymidine + phosphate = thymine + alpha-D-deoxyribose 1-phosphate

0

-

2.4.2.1

13 entries

2.4.2.2

7 entries

2.4.2.3

3 entries

2.4.2.4

5 entries

Activator in Enzyme-catalyzed Reactions (1 result)

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EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.4

dRib-1-P , a noncompetitive product inhibitor of the forward reaction, in the reverse reaction, dRib-1-P enhanced the binding of thymine

759338

-

Inhibitor in Enzyme-catalyzed Reactions (2 results)

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Show Inhibitors (2 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.4

dRib-1-P , a non-competitive product inhibitor of the forward reaction, in the reverse reaction, dRib-1-P enhanced the binding of thymine

759338

-

2.4.2.4

dRib-1-P is a competitive product inhibitor of the forward reaction, in the reverse reaction, dRib-1-P enhances the binding of thymine

759338

-

2.4.2.4

2 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (4 results)

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Show Turnover Number (4 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.4.2.1

115

-

reaction with hypoxanthine

489678

2.4.2.1

145

-

reaction with guanine

489678

2.7.1.212

73

-

presence of Mg2+, pH and temperature not specified in the publication

734747

2.7.1.212

73

-

presence of Mg2+, pH not specified in the publication, temperature not specified in the publication

734747

2.4.2.1

2 entries

2.7.1.212

2 entries

K_M Value (6 results)

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Show KM Value (6 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.4.2.1

0.1

-

reaction with adenine

489688

2.4.2.1

0.129

-

reaction with hypoxanthine

489678

2.4.2.1

0.133

-

reaction with guanine

489678

2.4.2.1

3 entries

2.4.2.4

0.09

-

pH 7.5, 37°C

759338

2.7.1.212

12

-

presence of Mg2+, pH and temperature not specified in the publication

734747

2.7.1.212

12

-

presence of Mg2+, pH not specified in the publication, temperature not specified in the publication

734747

2.7.1.212

2 entries

References & Links

Literature References (18)

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Show Reference (18 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

489678

1445943

Purine nucleoside phosphorylase from bovine lens: purification and properties

1992

Barsacchi, D.; Cappiello, M.; Tozzi, M.G.; Del Corso, A.; Peccatori, M.; Camici, M.; Ipata, P.L.; Mura, U.

Biochim. Biophys. Acta

1160

163-170

489688

235429

Purine nucleoside phosphorylase from Escherichia coli and Salmonella typhimurium. Purification and some properties

1975

Jensen, K.F.; Nygaard, P.

Eur. J. Biochem.

51

253-265

638508

13737038

Uridine and deoxyuridine phosphorylases from Ehrlich ascites tumor

1961

Pontis, H.; Degerstedt, G.; Reichard, P.

Biochim. Biophys. Acta

51

138-147

705495

19434693

The dual role of thymidine phosphorylase in cancer development and chemotherapy

2009

Bronckaers, A.; Gago, F.; Balzarini, J.; Liekens, S.

Med. Res. Rev.

29

903-953

734747

25822915

A pentose bisphosphate pathway for nucleoside degradation in Archaea

2015

Aono, R.; Sato, T.; Imanaka, T.; Atomi, H.

Nat. Chem. Biol.

11

355-360

758892

27474803

In silico binding analysis and SAR elucidations of newly designed benzopyrazine analogs as potent inhibitors of thymidine phosphorylase

2016

Taha, M.; Ismail, N.H.; Imran, S.; Rahim, F.; Wadood, A.; Al Muqarrabun, L.M.; Khan, K.M.; Ghufran, M.; Ali, M.

Bioorg. Chem.

68

80-89

758893

27955923

Thymidine esters as substrate analogue inhibitors of angiogenic enzyme thymidine phosphorylase in vitro

2017

Javaid, S.; Ishtiaq, M.; Shaikh, M.; Hameed, A.; Choudhary, M.I.

Bioorg. Chem.

70

44-56

758894

29626638

Synthesis and molecular docking study of piperazine derivatives as potent inhibitor of thymidine phosphorylase

2018

Uddin, I.; Taha, M.; Rahim, F.; Wadood, A.

Bioorg. Chem.

78

324-331

758895

29894893

Design, synthesis, in-vitro thymidine phosphorylase inhibition, in-vivo antiangiogenic and in-silico studies of C-6 substituted dihydropyrimidines

2018

Iftikhar, F.; Yaqoob, F.; Tabassum, N.; Jan, M.S.; Sadiq, A.; Tahir, S.; Batool, T.; Niaz, B.; Ansari, F.L.; Choudhary, M.I.; Rashid, U.

Bioorg. Chem.

80

99-111

758897

30634096

Identification of 1,2,4-triazoles as new thymidine phosphorylase inhibitors future anti-tumor drugs

2019

Shahzad, S.A.; Yar, M.; Khan, Z.A.; Shahzadi, L.; Naqvi, S.A.R.; Mahmood, A.; Ullah, S.; Shaikh, A.J.; Sherazi, T.A.; Bale, A.T.; Kukulowicz, J.; Bajda, M.

Bioorg. Chem.

85

209-220

758899

31151055

Synthesis, thymidine phosphorylase, angiogenic inhibition and molecular docking study of isoquinoline derivatives

2019

Zaman, K.; Rahim, F.; Taha, M.; Wadood, A.; Adnan Ali Shah, S.; Gollapalli, M.; Ullah, F.; Ahmed, A.

Bioorg. Chem.

89

102999

758902

32200327

Synthesis of indole based acetohydrazide analogs Their in vitro and in silico thymidine phosphorylase studies

2020

Taha, M.; Aldhamin, E.A.J.; Almandil, N.B.; Anouar, E.H.; Uddin, N.; Alomari, M.; Rahim, F.; Adalat, B.; Ibrahim, M.; Nawaz, F.; Iqbal, N.; Alghanem, B.; Altolayyan, A.; Khan, K.M.

Bioorg. Chem.

98

103745

759084

30015176

Synthesis, thymidine phosphorylase inhibitory and computational study of novel 1,3,4-oxadiazole-2-thione derivatives as potential anticancer agents

2018

Bajaj, S.; Roy, P.P.; Singh, J.

Comput. Biol. Chem.

76

151-160

759143

27783978

Recent discovery of non-nucleobase thymidine phosphorylase inhibitors targeting cancer

2016

Bera, H.; Chigurupati, S.

Eur. J. Med. Chem.

124

992-1003

759338

30849523

Kinetics mechanism and regulation of native human hepatic thymidine phosphorylase

2019

Oh, T.; El Kouni, M.H.

Int. J. Biochem. Cell Biol.

110

122-129

760047

31743355

Natural compounds as angiogenic enzyme thymidine phosphorylase inhibitors in vitro biochemical inhibition, mechanistic, and in silico modeling studies

2019

Javaid, S.; Shaikh, M.; Fatima, N.; Choudhary, M.I.

PLoS ONE

14

e0225056

760181

31690793

Synthesis of new isoquinoline-base-oxadiazole derivatives as potent inhibitors of thymidine phosphorylase and molecular docking study

2019

Zaman, K.; Rahim, F.; Taha, M.; Wadood, A.; Shah, S.A.A.; Ahmed, Q.U.; Zakaria, Z.A.

Sci. Rep.

9

16015

760726

8987664

Molecular cloning and expression of the pyrimidine nucleoside phosphorylase gene from Bacillus stearothermophilus TH 6-2

1996

Okuyama, K.; Hamamoto, T.; Noguchi, T.; Midorikawa, Y.

Biosci. Biotechnol. Biochem.

60

1655-1659

Links to other databases for 2-deoxy-alpha-D-ribose 1-phosphate

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PubChem