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Compound Detail

CHEMBL56253

(CYCLOHEXYLAMINO)METHYLENEDIPHOSPHONIC ACID
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O=P(O)(O)C(NC1CCCCC1)P(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL56253
Name (CYCLOHEXYLAMINO)METHYLENEDIPHOSPHONIC ACID
Phase Preclinical
Structure Type MOL
InChI Key GBBBPWVJGMFZGX-UHFFFAOYSA-N
5
Targets
20
Activities
2
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

273.2
MW (Da)
0.55
ALogP
3
HBA
5
HBD
127.1
PSA (Ų)
0.47
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 C7H17NO6P2
MW 273.16
Aromatic Rings 0
Heavy Atoms 16
NP-Likeness 0.04

Activity Summary

IC50 17 meas. best 7.21
Ki 3 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Farnesyl pyrophosphate synthase
CHEMBL1782
 Ki 8.0 7.67 10.0 3
Farnesyl pyrophosphate synthase
CHEMBL1782
 IC50 7.21 6.8125 61.1 4
Farnesyl pyrophosphate synthase
CHEMBL3693
 IC50 6.8 6.8 160.0 1
Entamoeba histolytica
CHEMBL612853
 IC50 4.8 4.8 16000.0 2
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 4.68 4.68 20893.0 2
Unchecked
CHEMBL612545
 IC50 4.4 4.365 39810.7 4

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Farnesyl pyrophosphate synthase Ki = 10.0 nM 8.0 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 IC50 = 61.1 nM 7.21 Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 after 10... 18327899
Farnesyl pyrophosphate synthase Ki = 62.4 nM 7.21 Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 18327899
Farnesyl pyrophosphate synthase IC50 = 160.0 nM 6.8 Inhibitory activity against Leishmania major Farnesyl diphosphate synthase 14695831
Farnesyl pyrophosphate synthase IC50 = 160.0 nM 6.8 Inhibitory activity against farnesyl Pyrophosphate Synthase was determined 14613320
Farnesyl pyrophosphate synthase IC50 = 158.49 nM 6.8 Inhibitory activity against farnesyl Pyrophosphate Synthase expressed as #NAME? ... 14613320
Farnesyl pyrophosphate synthase IC50 = 365.6 nM 6.44 Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 18327899
Entamoeba histolytica IC50 = 16000.0 nM 4.8 In vitro growth inhibition against Entamoeba histolytica 14695831
Entamoeba histolytica IC50 = 16000.0 nM 4.8 Antimicrobial activity against Entamoeba histolytica 20185316
Trypanosoma brucei rhodesiense IC50 = 20900.0 nM 4.68 In vitro growth inhibition of bloodstream-form Trypanosoma brucei rhodesiense Tr... 12086478
Trypanosoma brucei rhodesiense IC50 = 20892.96 nM 4.68 Predicted pIC50 against Trypomastigotes Brucei rhodesiense. 12086478
Unchecked IC50 = 40000.0 nM 4.4 Inhibitory activity, for stimulation of TNF-alpha release in gamma-delta T cells... 14711309
Unchecked IC50 = 39810.72 nM 4.4 pIC50 value for stimulation of TNF-alpha release in gamma-delta T cells, using i... 14711309
Unchecked IC50 = 47000.0 nM 4.33 Inhibitory activity, for stimulation of TNF-alpha release in gamma-delta T cells... 14711309
Unchecked IC50 = 46773.51 nM 4.33 pIC50 value for stimulation of TNF-alpha release in gamma-delta T cells, using a... 14711309

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
14613320 10.1021/jm0302344 Farnesyl pyrophosphate synthase 3
17149863 10.1021/jm060492b Escherichia coli 3
12086478 10.1021/jm0102809 Trypanosoma brucei rhodesiense 2
17474756 10.1021/jf0701032 Pyrroline-5-carboxylate reductase 2
31296439 10.1016/j.bmc.2019.07.004 Trypanosoma cruzi 1
20185316 10.1016/j.bmc.2010.01.068 Entamoeba histolytica 1
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1
18327899 10.1021/jm7015733 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
14695831 10.1021/jm030084x Entamoeba histolytica 1
12086478 10.1021/jm0102809 ADMET 1
12086478 10.1021/jm0102809 KB 1

Data from ChEMBL 36 via Core Engine