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Compound Detail

CHEMBL54714

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O=P(O)(O)C(Nc1ccc(Cl)cn1)P(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL54714
Phase Preclinical
Structure Type MOL
InChI Key BNMYZGAZFGNKTH-UHFFFAOYSA-N
8
Targets
21
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

302.6
MW (Da)
0.79
ALogP
4
HBA
5
HBD
140.0
PSA (Ų)
0.51
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C6H9ClN2O6P2
MW 302.55
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness -0.93

Activity Summary

IC50 19 meas. best 6.62
Ki 2 meas. best 7.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Farnesyl pyrophosphate synthase
CHEMBL1782
 Ki 7.64 7.64 23.0 1
Farnesyl pyrophosphate synthase
CHEMBL1782
 IC50 6.62 6.62 239.9 2
Squalene synthase
CHEMBL3338
 IC50 6.62 6.62 240.0 1
Unchecked
CHEMBL612545
 IC50 6.04 5.59 910.0 4
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL4091
 IC50 5.16 5.16 7000.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.0 4.9725 10000.0 4
Unchecked
CHEMBL612545
 Ki 4.82 4.82 15300.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 4.27 4.27 53300.0 2
Glutamine synthetase
CHEMBL2366486
 IC50 4.16 4.09 69000.0 2
Entamoeba histolytica
CHEMBL612853
 IC50 4.06 4.06 87000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Farnesyl pyrophosphate synthase Ki = 23.0 nM 7.64 Binding affinity towards farnesyl Pyrophosphate Synthase using [14C]- isopenteny... 14613320
Farnesyl pyrophosphate synthase IC50 = 240.0 nM 6.62 Inhibitory activity against farnesyl Pyrophosphate Synthase was determined 14613320
Farnesyl pyrophosphate synthase IC50 = 239.88 nM 6.62 Inhibitory activity against farnesyl Pyrophosphate Synthase expressed as #NAME? ... 14613320
Squalene synthase IC50 = 240.0 nM 6.62 Inhibitory activity against Leishmania major Farnesyl-diphosphatesynthase (FPP s... 14695831
Unchecked IC50 = 910.0 nM 6.04 Inhibition of Plasmodium vivax FPPS expressed in Escherichia coli BL21 by spectr... 19053772
Unchecked IC50 = 1000.0 nM 6.0 Inhibition of Plasmodium vivax FPPS expressed in Escherichia coli BL21 by spectr... 19053772
Unchecked IC50 = 7000.0 nM 5.16 Inhibition of Escherichia coli M15 DXR 19888756
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 7000.0 nM 5.16 Inhibition of Escherichia coli DXR 21379374
Unchecked IC50 = 7000.0 nM 5.16 Inhibition of DXR 21561155
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Growth inhibition of Plasmodium falciparum 19053772
Plasmodium falciparum IC50 = 10600.0 nM 4.97 In vitro growth inhibition against Plasmodium falciparum 14695831
Plasmodium falciparum IC50 = 11000.0 nM 4.96 Growth inhibition of Plasmodium falciparum 19053772
Plasmodium falciparum IC50 = 11000.0 nM 4.96 Antimicrobial activity against Plasmodium falciparum 20185316
Unchecked Ki = 15300.0 nM 4.82 Inhibition of Escherichia coli recombinant DXR using DXP as substrate and MgCl2 ... 21561155
Trypanosoma brucei rhodesiense IC50 = 53300.0 nM 4.27 In vitro growth inhibition of bloodstream-form Trypanosoma brucei rhodesiense Tr... 12086478
Trypanosoma brucei rhodesiense IC50 = 53703.18 nM 4.27 Predicted pIC50 against Trypomastigotes Brucei rhodesiense. 12086478
Glutamine synthetase IC50 = 69000.0 nM 4.16 Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase as... 15161194
Entamoeba histolytica IC50 = 87000.0 nM 4.06 In vitro growth inhibition against Entamoeba histolytica 14695831
Entamoeba histolytica IC50 = 87000.0 nM 4.06 Antimicrobial activity against Entamoeba histolytica 20185316
Glutamine synthetase IC50 = 96000.0 nM 4.02 Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase af... 15161194

Literature References

PubMed DOI Target Context # Activities
15161194 10.1021/jf049843q Glutamine synthetase 6
17149863 10.1021/jm060492b Escherichia coli 3
14613320 10.1021/jm0302344 Farnesyl pyrophosphate synthase 3
17474756 10.1021/jf0701032 Pyrroline-5-carboxylate reductase 2
14695831 10.1021/jm030084x ADMET 2
21561155 10.1021/jm200363d Unchecked 2
12086478 10.1021/jm0102809 Trypanosoma brucei rhodesiense 2
19053772 10.1021/jm8009074 Unchecked 2
19053772 10.1021/jm8009074 Plasmodium falciparum 2
12086478 10.1021/jm0102809 KB 1
14695831 10.1021/jm030084x Entamoeba histolytica 1
21561155 10.1021/jm200363d 1-deoxy-D-xylulose 5-phosphate reductoisomerase 1
21379374 10.1021/ml100243r 1-deoxy-D-xylulose 5-phosphate reductoisomerase 1
20185316 10.1016/j.bmc.2010.01.068 Entamoeba histolytica 1
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1
19888756 10.1021/jm9012592 Unchecked 1
12086478 10.1021/jm0102809 ADMET 1
12086477 10.1021/jm010279+ Rattus norvegicus 1
14695831 10.1021/jm030084x Squalene synthase 1
14695831 10.1021/jm030084x KB 1

Data from ChEMBL 36 via Core Engine