Compound Detail

CHEMBL55371

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O=P(O)(O)C(Nc1cccc(-c2ccccc2)c1)P(=O)(O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL55371
Phase	Preclinical
Structure Type	MOL
InChI Key	IXFMBXNLOHKCPT-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

343.2

MW (Da)

2.40

ALogP

HBA

HBD

127.1

PSA (Å²)

0.53

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C13H15NO6P2
MW	343.21
Aromatic Rings	2
Heavy Atoms	22
NP-Likeness	-0.48

Activity Summary

IC50 24 meas. best 6.51

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Carbonic anhydrase 14 CHEMBL3510	IC50	6.51	6.51	309.0	1
Hexokinase CHEMBL4151	IC50	6.09	5.8367	810.0	3
Unchecked CHEMBL612545	IC50	5.5	5.0167	3162.3	3
Vacuolar-type proton translocating pyrophosphatase 1 CHEMBL4386	IC50	5.37	5.37	4300.0	1
Entamoeba histolytica CHEMBL612853	IC50	5.18	5.17	6600.0	2
Carbonic anhydrase 9 CHEMBL3594	IC50	5.12	5.12	7629.0	1
Farnesyl pyrophosphate synthase CHEMBL1782	IC50	5.07	5.07	8500.0	1
Carbonic anhydrase 2 CHEMBL205	IC50	5.03	5.03	9371.0	1
Farnesyl pyrophosphate synthase CHEMBL3693	IC50	4.94	4.6267	11460.0	3
Matrix metalloproteinase-14 CHEMBL3869	IC50	4.4	4.4	40000.0	1
Trypanosoma cruzi CHEMBL368	IC50	4.33	4.33	47000.0	1
Neutrophil collagenase CHEMBL4588	IC50	4.28	4.28	52000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Carbonic anhydrase 14	IC50	=	309.0	nM	6.51	Inhibition of human recombinant carbonic anhydrase 14 preincubated for 15 mins b...	24650641
Hexokinase	IC50	=	810.0	nM	6.09	Inhibition of Trypanosoma cruzi hexokinase	17329254
Hexokinase	IC50	=	1950.0	nM	5.71	Inhibitory activity against Trypanosoma cruzi hexokinase	16392806
Hexokinase	IC50	=	1949.84	nM	5.71	Inhibitory activity against Trypanosoma cruzi hexokinase	16392806
Unchecked	IC50	=	3200.0	nM	5.5	Inhibition of the ATP-mediated HIV1 reverse transcriptase D67N/K70R/T215F/K219Q ...	18789701
Unchecked	IC50	=	3162.28	nM	5.5	Inhibition of the ATP-mediated HIV1 reverse transcriptase D67N/K70R/T215F/K219Q ...	18789701
Vacuolar-type proton translocating pyrophosphatase 1	IC50	=	4300.0	nM	5.37	Inhibition of recombinant Trypanosoma brucei soluble vacuolar pyrophosphatase ex...	16162013
Entamoeba histolytica	IC50	=	6600.0	nM	5.18	In vitro growth inhibition against Entamoeba histolytica	14695831
Entamoeba histolytica	IC50	=	7000.0	nM	5.16	Antimicrobial activity against Entamoeba histolytica	20185316
Carbonic anhydrase 9	IC50	=	7629.0	nM	5.12	Inhibition of human recombinant carbonic anhydrase 9 preincubated for 15 mins by...	24650641
Farnesyl pyrophosphate synthase	IC50	=	8500.0	nM	5.07	Inhibition of human FPPS	18789701
Carbonic anhydrase 2	IC50	=	9371.0	nM	5.03	Inhibition of human recombinant carbonic anhydrase 2 preincubated for 15 mins by...	24650641
Farnesyl pyrophosphate synthase	IC50	=	11460.0	nM	4.94	Inhibitory activity against FPPS in Leishmania major	16392806
Farnesyl pyrophosphate synthase	IC50	=	11481.54	nM	4.94	Inhibitory activity against FPPS in Leishmania major	16392806
Matrix metalloproteinase-14	IC50	=	40000.0	nM	4.4	Inhibition of MMP14 catalytic domain (unknown origin) using Mca-Pro-Leu-Gly-Leu-...	24071448
Trypanosoma cruzi	IC50	=	47000.0	nM	4.33	Growth inhibition of Trypanosoma cruzi intracellular amastigotes	16392806
Neutrophil collagenase	IC50	=	52000.0	nM	4.28	Inhibition of MMP8 catalytic domain (unknown origin) using Mca-Pro-Leu-Gly-Leu-D...	24071448
Unchecked	IC50	=	90000.0	nM	4.05	Inhibitory activity against Entamoeba histolytica pyrophosphate-dependent phosph...	14695831
Farnesyl pyrophosphate synthase	IC50	=	100000.0	nM	4.0	Inhibitory activity against Leishmania major Farnesyl diphosphate synthase	14695831

Literature References

PubMed	DOI	Target Context	# Activities
14695831	10.1021/jm030084x	Cricetinae gen. sp.	4
18789701	10.1016/j.bmc.2008.08.047	Unchecked	3
17149863	10.1021/jm060492b	Escherichia coli	3
22390415	10.1021/jm201657x	Farnesyl pyrophosphate synthase	2
16162013	10.1021/jm058220g	Vacuolar-type proton translocating pyrophosphatase 1	2
16392806	10.1021/jm0582625	Hexokinase	2
16392806	10.1021/jm0582625	Farnesyl pyrophosphate synthase	2
16392806	10.1021/jm0582625	KB	1
24650641	10.1016/j.bmcl.2014.03.001	Carbonic anhydrase 14	1
18789701	10.1016/j.bmc.2008.08.047	MCF7	1
17329254	10.1074/jbc.m607286200	Hexokinase	1
16392806	10.1021/jm0582625	Trypanosoma cruzi	1
16392806	10.1021/jm0582625	ADMET	1
16392806	10.1021/jm0582625	Dictyostelium discoideum	1
14695831	10.1021/jm030084x	Entamoeba histolytica	1
16162013	10.1021/jm058220g	KB	1
14695831	10.1021/jm030084x	Unchecked	1
14695831	10.1021/jm030084x	Farnesyl pyrophosphate synthase	1
14695831	10.1021/jm030084x	ADMET	1
14695831	10.1021/jm030084x	KB	1

Data from ChEMBL 36 via Core Engine