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Compound Detail

CHEMBL294192

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O=P(O)(O)C(CNc1ccccn1)P(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL294192
Phase Preclinical
Structure Type MOL
InChI Key BHVCADPDEFLLGM-UHFFFAOYSA-N
6
Targets
24
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

282.1
MW (Da)
0.17
ALogP
4
HBA
5
HBD
140.0
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 C7H12N2O6P2
MW 282.13
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness -0.70

Activity Summary

IC50 21 meas. best 7.82
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 7.9567 2.3 3
Farnesyl pyrophosphate synthase
CHEMBL1782
 IC50 7.82 7.02 15.0 4
Farnesyl pyrophosphate synthase
CHEMBL3693
 IC50 6.77 6.77 170.0 1
Unchecked
CHEMBL612545
 IC50 6.1 5.4183 794.3 6
Dictyostelium discoideum
CHEMBL612373
 IC50 4.82 4.82 15000.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.77 4.6725 17000.0 4
NCI-H460
CHEMBL396
 IC50 4.2 4.2 63700.0 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 = 15.0 nM 7.82 Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 after 10... 18327899
Farnesyl pyrophosphate synthase Ki = 16.0 nM 7.8 Binding affinity towards farnesyl Pyrophosphate Synthase using [14C]- isopenteny... 14613320
Farnesyl pyrophosphate synthase Ki = 36.9 nM 7.43 Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 18327899
Farnesyl pyrophosphate synthase IC50 = 170.0 nM 6.77 Inhibitory activity against Leishmania major Farnesyl diphosphate synthase 14695831
Farnesyl pyrophosphate synthase IC50 = 169.82 nM 6.77 Inhibitory activity against farnesyl Pyrophosphate Synthase expressed as #NAME? ... 14613320
Farnesyl pyrophosphate synthase IC50 = 170.0 nM 6.77 Inhibitory activity against farnesyl Pyrophosphate Synthase was determined 14613320
Farnesyl pyrophosphate synthase IC50 = 190.1 nM 6.72 Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 18327899
Unchecked IC50 = 794.33 nM 6.1 Inhibition of Plasmodium vivax FPPS expressed in Escherichia coli BL21 by spectr... 19053772
Unchecked IC50 = 820.0 nM 6.09 Inhibition of Plasmodium vivax FPPS expressed in Escherichia coli BL21 by spectr... 19053772
Unchecked IC50 = 4800.0 nM 5.32 Inhibitory activity, for stimulation of TNF-alpha release in gamma-delta T cells... 14711309
Unchecked IC50 = 4897.79 nM 5.31 pIC50 value for stimulation of TNF-alpha release in gamma-delta T cells, using i... 14711309
Unchecked IC50 = 14000.0 nM 4.85 Inhibitory activity, for stimulation of TNF-alpha release in gamma-delta T cells... 14711309
Unchecked IC50 = 14454.4 nM 4.84 pIC50 value for stimulation of TNF-alpha release in gamma-delta T cells, using a... 14711309
Dictyostelium discoideum IC50 = 15000.0 nM 4.82 Ability to inhibit growth of Dictostelium discoideum. 12086477
Plasmodium falciparum IC50 = 17000.0 nM 4.77 In vitro growth inhibition against Plasmodium falciparum 14695831
Plasmodium falciparum IC50 = 17000.0 nM 4.77 Antimicrobial activity against Plasmodium falciparum 20185316
Plasmodium falciparum IC50 = 25118.86 nM 4.6 Growth inhibition of Plasmodium falciparum 19053772
Plasmodium falciparum IC50 = 28000.0 nM 4.55 Growth inhibition of Plasmodium falciparum 19053772
NCI-H460 IC50 = 63700.0 nM 4.2 Antiproliferative activity against human NCI-H460 cell line by MTT assay 16970405

Literature References

PubMed DOI Target Context # Activities
23748153 10.1016/j.ejmech.2013.04.032 Osteoclast 4
18327899 10.1021/jm7015733 Farnesyl pyrophosphate synthase 4
14711309 10.1021/jm0303709 Unchecked 4
14613320 10.1021/jm0302344 Farnesyl pyrophosphate synthase 3
19053772 10.1021/jm8009074 Plasmodium falciparum 2
19053772 10.1021/jm8009074 Unchecked 2
16162013 10.1021/jm058220g Vacuolar-type proton translocating pyrophosphatase 1 2
16162013 10.1021/jm058220g KB 1
23748153 10.1016/j.ejmech.2013.04.032 Hydroxyapatite 1
18327899 10.1021/jm7015733 Rattus norvegicus 1
17149863 10.1021/jm060492b Escherichia coli 1
16970405 10.1021/jm060280e SF-268 1
16970405 10.1021/jm060280e NCI-H460 1
16970405 10.1021/jm060280e MCF7 1
12086477 10.1021/jm010279+ Dictyostelium discoideum 1
12086477 10.1021/jm010279+ Rattus norvegicus 1
14695831 10.1021/jm030084x Farnesyl pyrophosphate synthase 1
14695831 10.1021/jm030084x ADMET 1
14695831 10.1021/jm030084x KB 1
14695831 10.1021/jm030084x Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine