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Compound Detail

CHEMBL494897

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CCCCCCCCCCOc1ccc[n+](CC(P(=O)([O-])O)P(=O)(O)O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL494897
Phase Preclinical
Structure Type MOL
InChI Key QYJHUOZDBUEKQC-UHFFFAOYSA-N
6
Targets
22
Activities
2
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

423.4
MW (Da)
2.54
ALogP
4
HBA
3
HBD
131.0
PSA (Ų)
0.24
QED
0
Ro5 Violations
14
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H31NO7P2
MW 423.38
Aromatic Rings 1
Heavy Atoms 27

Activity Summary

IC50 18 meas. best 8.22
Ki 4 meas. best 5.43

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 8.22 6.56 6.0 3
Farnesyl pyrophosphate synthase
CHEMBL1782
 IC50 7.0 7.0 100.0 3
MDA-MB-231
CHEMBL400
 IC50 7.0 7.0 100.0 1
Geranylgeranyl pyrophosphate synthase
CHEMBL4769
 IC50 6.6 6.56 251.2 5
Plasmodium falciparum
CHEMBL364
 IC50 6.23 6.2 590.0 2
Unchecked
CHEMBL612545
 Ki 5.43 4.8967 3700.0 3
Geranylgeranyl pyrophosphate synthase
CHEMBL4769
 Ki 5.16 5.16 6900.0 1
Plasmodium berghei
CHEMBL612653
 IC50 5.0 5.0 10000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 6.0 nM 8.22 Inhibition of Escherichia coli OPPS using IPP as substrate 30730737
Farnesyl pyrophosphate synthase IC50 = 100.0 nM 7.0 Inhibition of human FPPS using FPP and [3H]-IPP as substrate incubated for 30 mi... 22390415
Farnesyl pyrophosphate synthase IC50 = 100.0 nM 7.0 Inhibition of human FPPS using GPP and [3H]IPP as substrate by scintillation cou... 22884353
MDA-MB-231 IC50 = 100.0 nM 7.0 Growth inhibition of human MDA-MB-231 cells 21780776
Farnesyl pyrophosphate synthase IC50 = 100.0 nM 7.0 Inhibition of human FPPS using IPP and GPP 30730737
Unchecked IC50 = 110.0 nM 6.96 Inhibition of Staphylococcus aureus HepPPS using IPP as substrate 30730737
Geranylgeranyl pyrophosphate synthase IC50 = 251.19 nM 6.6 Inhibition of human recombinant geranylgeranyl diphosphate synthase 18800762
Geranylgeranyl pyrophosphate synthase IC50 = 280.0 nM 6.55 Inhibition of human recombinant GGPS using [14C]-IPP as substrate incubated for ... 22884353
Geranylgeranyl pyrophosphate synthase IC50 = 280.0 nM 6.55 Inhibition of human GGPPS 30730737
Geranylgeranyl pyrophosphate synthase IC50 = 280.0 nM 6.55 Inhibition of human recombinant GGPPS using [14C]-IPP as substrate incubated for... 22390415
Geranylgeranyl pyrophosphate synthase IC50 = 280.0 nM 6.55 Inhibition of human recombinant geranylgeranyl diphosphate synthase 18800762
Plasmodium falciparum IC50 = 590.0 nM 6.23 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2me... 20457823
Plasmodium falciparum IC50 = 670.0 nM 6.17 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 ... 20457823
Unchecked Ki = 3700.0 nM 5.43 Inhibition of human FPPS 20457823
Geranylgeranyl pyrophosphate synthase Ki = 6900.0 nM 5.16 Inhibition of human GGPPS 20457823
Plasmodium berghei IC50 = 10000.0 nM 5.0 Antimalarial activity against Plasmodium berghei NK65 infected in human HepG2 ce... 20457823
Unchecked Ki = 13000.0 nM 4.89 Inhibition of Plasmodium vivax GGPPS 20457823
Unchecked IC50 = 32000.0 nM 4.5 Inhibition of human FPPS 20457823
Unchecked Ki = 43000.0 nM 4.37 Inhibition of Plasmodium vivax FPPS 20457823

Literature References

PubMed DOI Target Context # Activities
20457823 10.1128/aac.00198-10 Plasmodium berghei 10
20457823 10.1128/aac.00198-10 Unchecked 6
22390415 10.1021/jm201657x Farnesyl pyrophosphate synthase 2
30730737 10.1021/acs.jmedchem.8b01878 Unchecked 2
18800762 10.1021/jm800325y Geranylgeranyl pyrophosphate synthase 2
20457823 10.1128/aac.00198-10 Geranylgeranyl pyrophosphate synthase 2
20457823 10.1128/aac.00198-10 Plasmodium falciparum 2
20457823 10.1128/aac.00198-10 No relevant target 1
20457823 10.1128/aac.00198-10 ADMET 1
22390415 10.1021/jm201657x Geranylgeranyl pyrophosphate synthase 1
22884353 10.1016/j.bmc.2012.07.019 Farnesyl pyrophosphate synthase 1
22884353 10.1016/j.bmc.2012.07.019 Geranylgeranyl pyrophosphate synthase 1
21780776 10.1021/jm200587f MDA-MB-231 1
30730737 10.1021/acs.jmedchem.8b01878 Candida albicans 1
20457823 10.1128/aac.00198-10 HepG2 1
30730737 10.1021/acs.jmedchem.8b01878 Geranylgeranyl pyrophosphate synthase 1
30730737 10.1021/acs.jmedchem.8b01878 Farnesyl pyrophosphate synthase 1

Data from ChEMBL 36 via Core Engine