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Compound Detail

CHEMBL291736

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O=P(O)(O)C(Nc1ccccn1)P(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL291736
Phase Preclinical
Structure Type MOL
InChI Key OEAFYMDEEMRBOS-UHFFFAOYSA-N
4
Targets
21
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

268.1
MW (Da)
0.13
ALogP
4
HBA
5
HBD
140.0
PSA (Ų)
0.49
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C6H10N2O6P2
MW 268.10
Aromatic Rings 1
Heavy Atoms 16
NP-Likeness -0.58

Activity Summary

IC50 18 meas. best 7.93
Ki 3 meas. best 8.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Farnesyl pyrophosphate synthase
CHEMBL1782
 Ki 8.64 7.96 2.3 3
Farnesyl pyrophosphate synthase
CHEMBL1782
 IC50 7.93 7.035 11.7 6
Unchecked
CHEMBL612545
 IC50 5.13 4.9675 7400.0 4
Dictyostelium discoideum
CHEMBL612373
 IC50 4.92 4.92 12000.0 2
HFF
CHEMBL614071
 IC50 4.35 4.35 44630.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Farnesyl pyrophosphate synthase Ki = 2.3 nM 8.64 Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 after 10... 18327899
Farnesyl pyrophosphate synthase IC50 = 11.7 nM 7.93 Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 after 10... 18327899
Farnesyl pyrophosphate synthase Ki = 20.0 nM 7.7 Binding affinity towards farnesyl Pyrophosphate Synthase using [14C]- isopenteny... 14613320
Farnesyl pyrophosphate synthase Ki = 29.1 nM 7.54 Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 18327899
Farnesyl pyrophosphate synthase IC50 = 85.0 nM 7.07 Inhibition of human recombinant N-terminal-His6 tagged FPPS expressed in Escheri... 22390415
Farnesyl pyrophosphate synthase IC50 = 85.0 nM 7.07 Inhibition of human His6-tagged recombinant FPPS expressed in Escherichia coli B... 22884353
Farnesyl pyrophosphate synthase IC50 = 166.0 nM 6.78 Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 18327899
Farnesyl pyrophosphate synthase IC50 = 210.0 nM 6.68 Inhibitory activity against farnesyl Pyrophosphate Synthase was determined 14613320
Farnesyl pyrophosphate synthase IC50 = 208.93 nM 6.68 Inhibitory activity against farnesyl Pyrophosphate Synthase expressed as #NAME? ... 14613320
Unchecked IC50 = 7400.0 nM 5.13 Inhibitory activity, for stimulation of TNF-alpha release in gamma-delta T cells... 14711309
Unchecked IC50 = 7413.1 nM 5.13 pIC50 value for stimulation of TNF-alpha release in gamma-delta T cells, using i... 14711309
Dictyostelium discoideum IC50 = 12000.0 nM 4.92 Ability to inhibit growth of Dictostelium discoideum. 12086477
Dictyostelium discoideum IC50 = 12000.0 nM 4.92 Antimicrobial activity against Dictyostelium discoideum 18590315
Unchecked IC50 = 15488.17 nM 4.81 pIC50 value for stimulation of TNF-alpha release in gamma-delta T cells, using a... 14711309
Unchecked IC50 = 16000.0 nM 4.8 Inhibitory activity, for stimulation of TNF-alpha release in gamma-delta T cells... 14711309
HFF IC50 = 44630.0 nM 4.35 In vitro inhibitory concentration against the growth of Toxoplasma gondii in hum... 15857119

Literature References

PubMed DOI Target Context # Activities
15161194 10.1021/jf049843q Glutamine synthetase 6
14711309 10.1021/jm0303709 Unchecked 4
18327899 10.1021/jm7015733 Farnesyl pyrophosphate synthase 4
22390415 10.1021/jm201657x Farnesyl pyrophosphate synthase 3
17149863 10.1021/jm060492b Escherichia coli 3
14613320 10.1021/jm0302344 Farnesyl pyrophosphate synthase 3
17474756 10.1021/jf0701032 Pyrroline-5-carboxylate reductase 2
15857119 10.1021/jm040132t HFF 1
15857119 10.1021/jm040132t KB 1
15857119 10.1021/jm040132t ADMET 1
12086477 10.1021/jm010279+ Dictyostelium discoideum 1
12086477 10.1021/jm010279+ Rattus norvegicus 1
18327899 10.1021/jm7015733 Rattus norvegicus 1
18590315 10.1021/jm7015792 Farnesyl pyrophosphate synthase 1
18590315 10.1021/jm7015792 Dictyostelium discoideum 1
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1
20185316 10.1016/j.bmc.2010.01.068 Entamoeba histolytica 1
14695831 10.1021/jm030084x KB 1
22884353 10.1016/j.bmc.2012.07.019 Farnesyl pyrophosphate synthase 1
14695831 10.1021/jm030084x Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine