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BDBM50022238 (R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphate-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione::5-FLUORO-2'-DEOXYURIDINE-5'-MONOPHOSPHATE::5-Fluoro-2-Deoxyuridine Monophosphate (Fdump)::CHEMBL886::Phosphoric acid mono-[(2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl] ester::Phosphoric acid mono-[5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl] ester

SMILES: O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O

InChI Key: InChIKey=HFEKDTCAMMOLQP-RRKCRQDMSA-N

Data: 10 KI  4 IC50  2 Kd

PDB links: 38 PDB IDs match this monomer.

Find this compound or compounds like it in BindingDB or PDB:
   Substructure
Similarity at least:  must be >=0.5
Exact match

Activity Spreadsheet -- Enzyme Inhibition Constant Data from BindingDB

Found 15 hits for monomerid = 50022238   
Target/Host
(Institution)
LigandTarget/Host
Links
Ligand
Links
Trg + Lig
Links
Ki
nM
ΔG°
kcal/mole
IC50
nM
Kd
nM
EC50/IC50
nM
koff
s-1
kon
M-1s-1
pHTemp
°C
Thymidylate Synthase (TS)


(Lactobacillus casei)
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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0.00100n/an/a 0n/an/an/an/an/a



TBA

Curated by ChEMBL


Assay Description
Binding affinity to amethopterin-resistant Lactobacillus casei thymidylate synthetase in presence of cofactor permitting covalent bond formation


J Med Chem 20: 1469-73 (1977)


Article DOI: 10.1021/jm00221a021
BindingDB Entry DOI: 10.7270/Q2P55Q1K
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)
Thymidylate synthase


(Escherichia coli)
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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10n/an/an/an/an/an/an/an/a



TBA

Curated by ChEMBL


Assay Description
Compound was evaluated for the inhibition of dTMP synthetase with respect to dUMP.


J Med Chem 24: 1161-5 (1982)


Article DOI: 10.1021/jm00142a008
BindingDB Entry DOI: 10.7270/Q2B56K8B
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)
Thymidylate synthase


(Mus musculus)
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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10n/an/an/an/an/an/an/an/a



Polish Academy of Sciences

Curated by ChEMBL


Assay Description
Apparent Ki value of the compound was measured by competitive inhibition of Thymidylate Synthases from Ehrlich Carcinoma cells of mouse


J Med Chem 36: 3611-7 (1994)


Article DOI: 10.1021/jm00075a016
BindingDB Entry DOI: 10.7270/Q2222STZ
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)
Thymidylate Synthase (TS)


(Lactobacillus casei)
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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14n/an/an/an/an/an/an/an/a



TBA

Curated by ChEMBL


Assay Description
Inhibition of amethopterin-resistant Lactobacillus casei thymidylate synthetase-catalyzed dTMP formation using dUMP as substrate by spectrophotometri...


J Med Chem 20: 1469-73 (1977)


Article DOI: 10.1021/jm00221a021
BindingDB Entry DOI: 10.7270/Q2P55Q1K
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)
Thymidylate Synthase (TS)


(Lactobacillus casei)
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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14n/an/an/an/an/an/an/an/a



TBA

Curated by ChEMBL


Assay Description
Competitive inhibition of thymidylate synthase purified from methotrexate-resistant Lactobacillus casei using 2'-deoxy[5-3H]uridine 5'-phosphate by r...


J Med Chem 22: 1137-9 (1979)


Article DOI: 10.1021/jm00195a028
BindingDB Entry DOI: 10.7270/Q2XK8H3F
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)
Thymidylate synthase


(Homo sapiens (Human))
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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14n/an/an/an/an/an/an/an/a



Universit£ degli Studi di Perugia

Curated by ChEMBL


Assay Description
Inhibition of human thymidylate synthase expressed in Escherichia coli incubated for 1 hr by spectrophotometry


J Med Chem 55: 10272-6 (2012)


Article DOI: 10.1021/jm300850v
BindingDB Entry DOI: 10.7270/Q2P2708R
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)
Thymidylate synthase


(Mus musculus)
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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20n/an/an/an/an/an/an/an/a



Polish Academy of Sciences

Curated by ChEMBL


Assay Description
Apparent Ki value of the compound was measured by competitive inhibition of Thymidylate Synthases from L1210 cells of mouse


J Med Chem 36: 3611-7 (1994)


Article DOI: 10.1021/jm00075a016
BindingDB Entry DOI: 10.7270/Q2222STZ
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)
Thymidylate synthase


(Mus musculus)
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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20n/an/an/an/an/an/an/an/a



Polish Academy of Sciences

Curated by ChEMBL


Assay Description
Time-independent inhibition of thymidylate synthase from parenteral L1210 cells


J Med Chem 43: 4647-56 (2001)


Article DOI: 10.1021/jm000975u
BindingDB Entry DOI: 10.7270/Q2TT4RPX
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)
Thymidylate synthase


(Mus musculus)
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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30n/an/an/an/an/an/an/an/a



Polish Academy of Sciences

Curated by ChEMBL


Assay Description
Time-independent inhibition of thymidylate synthase from FdUrd-resistant L1210 cells


J Med Chem 43: 4647-56 (2001)


Article DOI: 10.1021/jm000975u
BindingDB Entry DOI: 10.7270/Q2TT4RPX
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)
Thymidylate Synthase (TS)


(Lactobacillus casei)
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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1.49E+4n/an/an/an/an/an/an/an/a



TBA

Curated by ChEMBL


Assay Description
Inhibition of amethopterin-resistant Lactobacillus casei thymidylate synthetase-catalyzed 5-BrdUMP dehalogenation by absorbance analysis in absence o...


J Med Chem 20: 1469-73 (1977)


Article DOI: 10.1021/jm00221a021
BindingDB Entry DOI: 10.7270/Q2P55Q1K
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)
Thymidylate Synthase (TS)


(Lactobacillus casei)
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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n/an/an/a 10n/an/an/an/an/a



TBA

Curated by ChEMBL


Assay Description
Binding affinity to amethopterin-resistant Lactobacillus casei thymidylate synthetase in presence of cofactor not permitting covalent bond formation


J Med Chem 20: 1469-73 (1977)


Article DOI: 10.1021/jm00221a021
BindingDB Entry DOI: 10.7270/Q2P55Q1K
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)
Thymidylate synthase


(Mus musculus)
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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n/an/a 8n/an/an/an/an/an/a



University of Minnesota

Curated by ChEMBL


Assay Description
Inhibition of cellular thymidylate synthase activity of mouse fibroblast (L929 TK-) in permeabilised cells.


J Med Chem 39: 4569-75 (1996)


Article DOI: 10.1021/jm9603680
BindingDB Entry DOI: 10.7270/Q2445N57
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)
Thymidylate synthase


(Mus musculus)
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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n/an/a 42n/an/an/an/an/an/a



University of Minnesota

Curated by ChEMBL


Assay Description
Inhibition of cellular thymidylate synthase activity of murine leukemia cell line (L1210) in permeabilised cells.


J Med Chem 39: 4569-75 (1996)


Article DOI: 10.1021/jm9603680
BindingDB Entry DOI: 10.7270/Q2445N57
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)
Thymidylate synthase


(Mus musculus)
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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n/an/a 17n/an/an/an/an/an/a



University of Minnesota

Curated by ChEMBL


Assay Description
Inhibition of cellular thymidylate synthase activity of murine leukemia cell line (L1210) in intact cells.


J Med Chem 39: 4569-75 (1996)


Article DOI: 10.1021/jm9603680
BindingDB Entry DOI: 10.7270/Q2445N57
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)
Thymidylate synthase


(Mus musculus)
BDBM50022238
PNG
((R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphat...)
Show SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)n1cc(F)c(=O)[nH]c1=O
Show InChI InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
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n/an/a>1.00E+4n/an/an/an/an/an/a



University of Minnesota

Curated by ChEMBL


Assay Description
Inhibition of cellular thymidylate synthase activity of mouse fibroblast (L929 TK-) in intact cells.


J Med Chem 39: 4569-75 (1996)


Article DOI: 10.1021/jm9603680
BindingDB Entry DOI: 10.7270/Q2445N57
More data for this
Ligand-Target Pair
3D
3D Structure (crystal)