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Literature summary extracted from

  • Reigan, P.; Edwards, P.N.; Gbaj, A.; Cole, C.; Barry, S.T.; Page, K.M.; Ashton, S.E.; Luke, R.W.; Douglas, K.T.; Stratford, I.J.; Jaffar, M.; Bryce, R.A.; Freeman, S.
    Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs (2005), J. Med. Chem., 48, 392-402.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.4.2.4 5-bromo-6-[(2'-nitroimidazol-1'-yl)methyl]uracil IC50: 0.0244 mM Escherichia coli
2.4.2.4 5-bromo-6-[(2'-nitroimidazol-1'-yl)methyl]uracil IC50: 0.16 mM Homo sapiens
2.4.2.4 5-bromo-6-[(4'-nitroimidazol-1'-yl)methyl]uracil IC50: 0.0066 mM Escherichia coli
2.4.2.4 5-bromo-6-[(4'-nitroimidazol-1'-yl)methyl]uracil IC50: 0.181 mM Homo sapiens
2.4.2.4 5-chloro-6-[(2'-nitroimidazol-1'-yl)methyl]uracil IC50: 0.0217 mM Escherichia coli
2.4.2.4 5-chloro-6-[(2'-nitroimidazol-1'-yl)methyl]uracil IC50: 0.115 mM Homo sapiens
2.4.2.4 5-chloro-6-[(4'-nitroimidazol-1'-yl)methyl]uracil IC50: 0.007 mM Escherichia coli
2.4.2.4 5-chloro-6-[(4'-nitroimidazol-1'-yl)methyl]uracil IC50: 0.2 mM Homo sapiens
2.4.2.4 6-[(2'-aminoimidazol-1'-yl)methyl]-5-bromouracil IC50: 0.0000187 mM Escherichia coli
2.4.2.4 6-[(2'-aminoimidazol-1'-yl)methyl]-5-bromouracil IC50: 0.000019 mM Homo sapiens
2.4.2.4 6-[(2'-aminoimidazol-1'-yl)methyl]-5-chlorouracil IC50: below 0.0000206 mM Escherichia coli
2.4.2.4 6-[(2'-aminoimidazol-1'-yl)methyl]-5-chlorouracil IC50: below 0.000049 mM Homo sapiens
2.4.2.4 6-[(2'-aminoimidazol-1'-yl)methyl]uracil IC50: 0.00056 mM Escherichia coli
2.4.2.4 6-[(2'-aminoimidazol-1'-yl)methyl]uracil IC50: 0.0001 mM Homo sapiens
2.4.2.4 6-[(2'-nitroimidazol-1'-yl)methyl]uracil IC50: 0.0024 mM Escherichia coli
2.4.2.4 6-[(2'-nitroimidazol-1'-yl)methyl]uracil IC50: 0.2577 mM Homo sapiens
2.4.2.4 6-[(4'-aminoimidazol-1'-yl)methyl]-5-bromouracil IC50: 0.00065 mM Escherichia coli
2.4.2.4 6-[(4'-aminoimidazol-1'-yl)methyl]-5-bromouracil IC50: 0.041 mM Homo sapiens
2.4.2.4 6-[(4'-aminoimidazol-1'-yl)methyl]-5-chlorouracil IC50: 0.00073 mM Escherichia coli
2.4.2.4 6-[(4'-aminoimidazol-1'-yl)methyl]-5-chlorouracil IC50: 0.026 mM Homo sapiens
2.4.2.4 6-[(4'-aminoimidazol-1'-yl)methyl]uracil IC50: 0.1014 mM Escherichia coli
2.4.2.4 6-[(4'-aminoimidazol-1'-yl)methyl]uracil IC50: 0.143 mM Homo sapiens
2.4.2.4 6-[(4'-nitroimidazol-1'-yl)methyl]uracil IC50: 0.0138 mM Escherichia coli
2.4.2.4 6-[(4'-nitroimidazol-1'-yl)methyl]uracil IC50: 0.5 mM Homo sapiens

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.4.2.4 0.16
-
5-nitro-2'-deoxyuridine pH 7.4, 25°C Homo sapiens
2.4.2.4 0.23
-
5-nitro-2'-deoxyuridine pH 7.4, 25°C Escherichia coli
2.4.2.4 0.24
-
thymidine pH 7.4, 25°C Escherichia coli

Organism

EC Number Organism UniProt Comment Textmining
2.4.2.4 Escherichia coli
-
-
-
2.4.2.4 Homo sapiens P19971
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.4.2.4 5-nitro-2'-deoxyuridine + phosphate
-
Escherichia coli 5-nitrouracil + 2-deoxy-D-ribose 1-phosphate
-
?
2.4.2.4 5-nitro-2'-deoxyuridine + phosphate
-
Homo sapiens 5-nitrouracil + 2-deoxy-D-ribose 1-phosphate
-
?
2.4.2.4 thymidine + phosphate
-
Escherichia coli thymine + 2-deoxy-D-ribose 1-phosphate
-
?

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.4.2.4 2.88
-
5-nitro-2'-deoxyuridine pH 7.4, 25°C Homo sapiens
2.4.2.4 20
-
5-nitro-2'-deoxyuridine pH 7.4, 25°C Escherichia coli
2.4.2.4 1770
-
thymidine pH 7.4, 25°C Escherichia coli

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.4.2.4 0.0000187
-
IC50: 0.0000187 mM Escherichia coli 6-[(2'-aminoimidazol-1'-yl)methyl]-5-bromouracil
2.4.2.4 0.000019
-
IC50: 0.000019 mM Homo sapiens 6-[(2'-aminoimidazol-1'-yl)methyl]-5-bromouracil
2.4.2.4 0.0000206
-
IC50: below 0.0000206 mM Escherichia coli 6-[(2'-aminoimidazol-1'-yl)methyl]-5-chlorouracil
2.4.2.4 0.000049
-
IC50: below 0.000049 mM Homo sapiens 6-[(2'-aminoimidazol-1'-yl)methyl]-5-chlorouracil
2.4.2.4 0.0001
-
IC50: 0.0001 mM Homo sapiens 6-[(2'-aminoimidazol-1'-yl)methyl]uracil
2.4.2.4 0.00056
-
IC50: 0.00056 mM Escherichia coli 6-[(2'-aminoimidazol-1'-yl)methyl]uracil
2.4.2.4 0.00065
-
IC50: 0.00065 mM Escherichia coli 6-[(4'-aminoimidazol-1'-yl)methyl]-5-bromouracil
2.4.2.4 0.00073
-
IC50: 0.00073 mM Escherichia coli 6-[(4'-aminoimidazol-1'-yl)methyl]-5-chlorouracil
2.4.2.4 0.0024
-
IC50: 0.0024 mM Escherichia coli 6-[(2'-nitroimidazol-1'-yl)methyl]uracil
2.4.2.4 0.0066
-
IC50: 0.0066 mM Escherichia coli 5-bromo-6-[(4'-nitroimidazol-1'-yl)methyl]uracil
2.4.2.4 0.007
-
IC50: 0.007 mM Escherichia coli 5-chloro-6-[(4'-nitroimidazol-1'-yl)methyl]uracil
2.4.2.4 0.0138
-
IC50: 0.0138 mM Escherichia coli 6-[(4'-nitroimidazol-1'-yl)methyl]uracil
2.4.2.4 0.0217
-
IC50: 0.0217 mM Escherichia coli 5-chloro-6-[(2'-nitroimidazol-1'-yl)methyl]uracil
2.4.2.4 0.0244
-
IC50: 0.0244 mM Escherichia coli 5-bromo-6-[(2'-nitroimidazol-1'-yl)methyl]uracil
2.4.2.4 0.026
-
IC50: 0.026 mM Homo sapiens 6-[(4'-aminoimidazol-1'-yl)methyl]-5-chlorouracil
2.4.2.4 0.041
-
IC50: 0.041 mM Homo sapiens 6-[(4'-aminoimidazol-1'-yl)methyl]-5-bromouracil
2.4.2.4 0.1014
-
IC50: 0.1014 mM Escherichia coli 6-[(4'-aminoimidazol-1'-yl)methyl]uracil
2.4.2.4 0.115
-
IC50: 0.115 mM Homo sapiens 5-chloro-6-[(2'-nitroimidazol-1'-yl)methyl]uracil
2.4.2.4 0.143
-
IC50: 0.143 mM Homo sapiens 6-[(4'-aminoimidazol-1'-yl)methyl]uracil
2.4.2.4 0.16
-
IC50: 0.16 mM Homo sapiens 5-bromo-6-[(2'-nitroimidazol-1'-yl)methyl]uracil
2.4.2.4 0.181
-
IC50: 0.181 mM Homo sapiens 5-bromo-6-[(4'-nitroimidazol-1'-yl)methyl]uracil
2.4.2.4 0.2
-
IC50: 0.2 mM Homo sapiens 5-chloro-6-[(4'-nitroimidazol-1'-yl)methyl]uracil
2.4.2.4 0.2577
-
IC50: 0.2577 mM Homo sapiens 6-[(2'-nitroimidazol-1'-yl)methyl]uracil
2.4.2.4 0.5
-
IC50: 0.5 mM Homo sapiens 6-[(4'-nitroimidazol-1'-yl)methyl]uracil