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Compound Detail

CHEMBL56073

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CN(CCCCc1ccccc1)CCC(O)(P(=O)(O)O)P(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL56073
Phase Preclinical
Structure Type MOL
InChI Key VFLFYDXGZMGUAF-UHFFFAOYSA-N
11
Targets
22
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

381.3
MW (Da)
1.33
ALogP
4
HBA
5
HBD
138.5
PSA (Ų)
0.30
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C14H25NO7P2
MW 381.30
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness -0.09

Activity Summary

IC50 21 meas. best 8.98
Ki 1 meas. best 7.34

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Farnesyl pyrophosphate synthase
CHEMBL1782
 IC50 8.98 7.2 1.0 3
Farnesyl pyrophosphate synthase
CHEMBL1782
 Ki 7.34 7.34 46.0 1
Farnesyl pyrophosphate synthase
CHEMBL3693
 IC50 6.31 6.31 490.0 1
Unchecked
CHEMBL612545
 IC50 6.21 6.205 610.0 2
Farnesyl diphosphate synthase
CHEMBL1075078
 IC50 5.89 5.89 1300.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.54 5.53 2900.0 4
Geranylgeranyl pyrophosphate synthase
CHEMBL4769
 IC50 5.4 5.39 3981.1 2
NCI-H460
CHEMBL396
 IC50 4.64 4.64 22900.0 1
Entamoeba histolytica
CHEMBL612853
 IC50 4.63 4.63 23400.0 2
Escherichia coli
CHEMBL354
 IC50 4.48 4.48 33000.0 1
SF-268
CHEMBL613977
 IC50 4.31 4.31 49200.0 1
MCF7
CHEMBL387
 IC50 4.08 4.08 82500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Farnesyl pyrophosphate synthase IC50 = 1.047 nM 8.98 Negative logarithm of inhibitory concentration against bone resorption 12825934
Farnesyl pyrophosphate synthase Ki = 46.0 nM 7.34 Binding affinity towards farnesyl Pyrophosphate Synthase using [14C]- isopenteny... 14613320
Farnesyl pyrophosphate synthase IC50 = 490.0 nM 6.31 Inhibitory activity against Leishmania major Farnesyl diphosphate synthase 14695831
Farnesyl pyrophosphate synthase IC50 = 489.78 nM 6.31 Inhibitory activity against farnesyl Pyrophosphate Synthase expressed as #NAME? ... 14613320
Farnesyl pyrophosphate synthase IC50 = 490.0 nM 6.31 Inhibitory activity against farnesyl Pyrophosphate Synthase was determined 14613320
Unchecked IC50 = 610.0 nM 6.21 Inhibition of Plasmodium vivax FPPS expressed in Escherichia coli BL21 by spectr... 19053772
Unchecked IC50 = 630.96 nM 6.2 Inhibition of Plasmodium vivax FPPS expressed in Escherichia coli BL21 by spectr... 19053772
Farnesyl diphosphate synthase IC50 = 1300.0 nM 5.89 Inhibition of Escherichia coli FPPS 17149863
Plasmodium falciparum IC50 = 2900.0 nM 5.54 In vitro growth inhibition against Plasmodium falciparum 14695831
Plasmodium falciparum IC50 = 2900.0 nM 5.54 Growth inhibition of Plasmodium falciparum 19053772
Plasmodium falciparum IC50 = 2900.0 nM 5.54 Antiparasitic activity against Plasmodium falciparum 3D7 infected in human eryth... 33522236
Plasmodium falciparum IC50 = 3162.28 nM 5.5 Growth inhibition of Plasmodium falciparum 19053772
Geranylgeranyl pyrophosphate synthase IC50 = 3981.07 nM 5.4 Inhibition of human recombinant geranylgeranyl diphosphate synthase 18800762
Geranylgeranyl pyrophosphate synthase IC50 = 4170.0 nM 5.38 Inhibition of human recombinant geranylgeranyl diphosphate synthase 18800762
NCI-H460 IC50 = 22900.0 nM 4.64 Antiproliferative activity against human NCI-H460 cell line by MTT assay 16970405
Entamoeba histolytica IC50 = 23400.0 nM 4.63 In vitro growth inhibition against Entamoeba histolytica 14695831
Entamoeba histolytica IC50 = 23400.0 nM 4.63 Antiparasitic activity against Entamoeba histolytica trophozoites assessed as pa... 33522236
Escherichia coli IC50 = 33000.0 nM 4.48 Antibacterial activity against Escherichia coli K12 by broth microdilution metho... 17149863
SF-268 IC50 = 49200.0 nM 4.31 Antiproliferative activity against human SF-268 cell line by MTT assay 16970405
MCF7 IC50 = 82500.0 nM 4.08 Antiproliferative activity against human MCF7 cell line by MTT assay 16970405

Literature References

PubMed DOI Target Context # Activities
17149863 10.1021/jm060492b Escherichia coli 10
14695831 10.1021/jm030084x Cricetinae gen. sp. 4
14613320 10.1021/jm0302344 Farnesyl pyrophosphate synthase 3
19053772 10.1021/jm8009074 Plasmodium falciparum 2
14695831 10.1021/jm030084x ADMET 2
19053772 10.1021/jm8009074 Unchecked 2
18800762 10.1021/jm800325y Geranylgeranyl pyrophosphate synthase 2
12825934 10.1021/jm030054u Farnesyl pyrophosphate synthase 2
16970405 10.1021/jm060280e NCI-H460 1
33522236 10.1021/acs.jmedchem.0c01292 Entamoeba histolytica 1
33522236 10.1021/acs.jmedchem.0c01292 Plasmodium falciparum 1
17149863 10.1021/jm060492b Farnesyl diphosphate synthase 1
17149863 10.1021/jm060492b Unchecked 1
17149863 10.1021/jm060492b 1-deoxy-D-xylulose 5-phosphate reductoisomerase 1
16970405 10.1021/jm060280e SF-268 1
16970405 10.1021/jm060280e MCF7 1
12166945 10.1021/jm020819i Rattus norvegicus 1
14695831 10.1021/jm030084x Farnesyl pyrophosphate synthase 1
14695831 10.1021/jm030084x KB 1
14695831 10.1021/jm030084x Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine