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Compound Detail

CHEMBL293522

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O=P(O)(O)C(O)(CCc1cccnc1)P(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL293522
Phase Preclinical
Structure Type MOL
InChI Key ILROXFQHACCDLA-UHFFFAOYSA-N
4
Targets
27
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

297.1
MW (Da)
0.02
ALogP
4
HBA
5
HBD
148.2
PSA (Ų)
0.48
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C8H13NO7P2
MW 297.14
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness -0.05

Activity Summary

IC50 23 meas. best 7.11
Ki 3 meas. best 7.11
EC50 1 meas. best 5.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Farnesyl pyrophosphate synthase
CHEMBL1782
 IC50 7.11 5.9657 78.0 7
Farnesyl pyrophosphate synthase
CHEMBL1782
 Ki 7.11 6.6133 78.0 3
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 5.77 5.77 1698.2 3
Unchecked
CHEMBL612545
 EC50 5.77 5.77 1700.0 1
Trypanosoma brucei
CHEMBL612849
 IC50 5.77 5.77 1700.0 1
Unchecked
CHEMBL612545
 IC50 5.27 4.875 5400.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Farnesyl pyrophosphate synthase IC50 = 78.0 nM 7.11 Inhibition of human FPPS using pre-incubation of compound with enzyme 25815158
Farnesyl pyrophosphate synthase Ki = 78.0 nM 7.11 Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 after 10... 18327899
Farnesyl pyrophosphate synthase IC50 = 337.3 nM 6.47 Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 after 10... 18327899
Farnesyl pyrophosphate synthase IC50 = 363.0 nM 6.44 Inhibition of human FPPS in absence of pre-incubation of compound with enzyme 25815158
Farnesyl pyrophosphate synthase Ki = 362.6 nM 6.44 Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 18327899
Farnesyl pyrophosphate synthase Ki = 510.0 nM 6.29 Binding affinity towards farnesyl Pyrophosphate Synthase using [14C]- isopenteny... 14613320
Trypanosoma brucei IC50 = 1700.0 nM 5.77 Inhibition of Trypanosoma rhodesiense (strain STIB900) was determined using bloo... 11300872
Trypanosoma brucei rhodesiense IC50 = 1700.0 nM 5.77 Antiparasitic activity against Trypanosoma brucei rhodesiense STIB900 bloodstrea... 33522236
Trypanosoma brucei rhodesiense IC50 = 1698.24 nM 5.77 Predicted pIC50 against Trypomastigotes Brucei rhodesiense. 12086478
Trypanosoma brucei rhodesiense IC50 = 1700.0 nM 5.77 In vitro growth inhibition of bloodstream-form Trypanosoma brucei rhodesiense Tr... 12086478
Unchecked EC50 = 1700.0 nM 5.77 Inhibition of Trypanosoma brucei rhodesiense FPPS 25815158
Farnesyl pyrophosphate synthase IC50 = 2113.0 nM 5.67 Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 18327899
Farnesyl pyrophosphate synthase IC50 = 2930.0 nM 5.53 Inhibitory activity against the human recombinant FPPSase (Farnesyl diphosphate)... 12014956
Farnesyl pyrophosphate synthase IC50 = 5400.0 nM 5.27 Inhibitory activity against farnesyl Pyrophosphate Synthase was determined 14613320
Farnesyl pyrophosphate synthase IC50 = 5370.32 nM 5.27 Inhibitory activity against farnesyl Pyrophosphate Synthase expressed as #NAME? ... 14613320
Unchecked IC50 = 5400.0 nM 5.27 Inhibition of Leishmania donovani FPPS 25815158
Unchecked IC50 = 33000.0 nM 4.48 Inhibition of Trypanosoma brucei FPPS 25815158

Literature References

PubMed DOI Target Context # Activities
18327899 10.1021/jm7015733 Farnesyl pyrophosphate synthase 4
14711309 10.1021/jm0303709 Unchecked 4
14613320 10.1021/jm0302344 Farnesyl pyrophosphate synthase 3
25815158 10.1021/ml500528x Unchecked 3
25815158 10.1021/ml500528x Farnesyl pyrophosphate synthase 2
11300872 10.1021/jm0002578 Trypanosoma cruzi 2
12086478 10.1021/jm0102809 Trypanosoma brucei rhodesiense 2
11300872 10.1021/jm0002578 Leishmania donovani 1
15857119 10.1021/jm040132t HFF 1
12014956 10.1021/jm010412y Farnesyl pyrophosphate synthase 1
12086477 10.1021/jm010279+ Dictyostelium discoideum 1
12086477 10.1021/jm010279+ Rattus norvegicus 1
11300872 10.1021/jm0002578 Vero 1
11300872 10.1021/jm0002578 Plasmodium falciparum 1
33522236 10.1021/acs.jmedchem.0c01292 Plasmodium falciparum 1
11300872 10.1021/jm0002578 Trypanosoma brucei 1
14695831 10.1021/jm030084x KB 1
14695831 10.1021/jm030084x Plasmodium falciparum 1
14695831 10.1021/jm030084x Entamoeba histolytica 1
12086478 10.1021/jm0102809 ADMET 1

Data from ChEMBL 36 via Core Engine