Compound Detail

CHEMBL501701

N,N-HEXAMETHYLENEAMILORIDE

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N=C(N)NC(=O)c1nc(Cl)c(N2CCCCCC2)nc1N

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL501701
Name	N,N-HEXAMETHYLENEAMILORIDE
Phase	Preclinical
Structure Type	MOL
InChI Key	RQQJJXVETXFINY-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

311.8

MW (Da)

0.72

ALogP

HBA

HBD

134.0

PSA (Å²)

0.47

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C12H18ClN7O
MW	311.78
Aromatic Rings	1
Heavy Atoms	21
NP-Likeness	-0.86

Activity Summary

IC50 33 meas. best 9.72

Ki 8 meas. best 7.89

EC50 2 meas. best 5.87

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Sodium/hydrogen exchanger 1 CHEMBL2781	IC50	9.72	7.6	0.2	2
Sodium/hydrogen exchanger 1 CHEMBL2577	Ki	7.89	7.89	13.0	2
Sodium/hydrogen exchanger 1 CHEMBL2577	IC50	6.77	6.77	171.0	1
Adenosine A2 receptor CHEMBL2094257	IC50	6.57	6.57	270.0	1
Sodium/hydrogen exchanger 5 CHEMBL3058	Ki	6.43	6.43	370.0	2
Unchecked CHEMBL612545	EC50	5.87	5.64	1340.0	2
Urokinase-type plasminogen activator CHEMBL3286	Ki	5.87	5.87	1356.0	1
Sodium/hydrogen exchanger 5 CHEMBL3058	IC50	5.82	5.82	1510.0	1
Sodium/hydrogen exchanger 3 CHEMBL3879842	Ki	5.62	5.62	2400.0	2
Urokinase-type plasminogen activator CHEMBL3286	IC50	5.62	5.62	2400.0	1
HEK293 CHEMBL614818	IC50	5.55	5.55	2800.0	1
Plasmodium falciparum CHEMBL364	IC50	5.5	5.1667	3162.3	6
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.48	5.48	3300.0	1
TE-5 CHEMBL2366245	IC50	5.33	5.33	4700.0	1
Adenosine receptor A2a CHEMBL251	IC50	5.29	5.29	5100.0	1
TE-11 CHEMBL2366166	IC50	5.25	5.25	5600.0	1
HT-1080 CHEMBL614580	IC50	5.18	5.02	6600.0	2
Unchecked CHEMBL612545	IC50	5.16	4.985	7000.0	4
Urokinase-type plasminogen activator CHEMBL1075311	Ki	5.03	5.03	9308.0	1
TE-9 CHEMBL2366147	IC50	5.02	5.02	9600.0	1
TE-1 CHEMBL2366092	IC50	4.97	4.97	10600.0	1
TE-10 CHEMBL2366308	IC50	4.93	4.93	11800.0	1
TE-6 CHEMBL2366144	IC50	4.87	4.87	13600.0	1
TE-15 CHEMBL2366086	IC50	4.75	4.75	17900.0	1
HepG2 CHEMBL395	IC50	4.7	4.7	20200.0	1
NHDF CHEMBL614200	IC50	4.62	4.62	23700.0	1
MDA-MB-231 CHEMBL400	IC50	4.56	4.56	27300.0	1
Sodium channel protein type 5 subunit alpha CHEMBL1980	IC50	4.52	4.52	30000.0	1
TMK-1 CHEMBL4296504	IC50	4.37	4.37	42800.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	467.67	ng.hr.mL-1	Mus musculus
AUC	498.85	ng.hr.mL-1	Rattus norvegicus
CL	24.0	mL.min-1.g-1	Homo sapiens
CL	74.0	mL.min-1.g-1	Homo sapiens
CL	726.0	mL.min-1.g-1	Mus musculus
CL	2243.0	mL.min-1.g-1	Mus musculus
CL	86.0	mL.min-1.kg-1	Mus musculus
CL	59.0	mL.min-1.kg-1	Mus musculus
CL	83.5	mL.min-1.kg-1	Rattus norvegicus
CL	46.2	mL.min-1.kg-1	Rattus norvegicus
CL	0.2	mL.min-1.kg-1	Rattus norvegicus
CL	46.0	mL.min-1.kg-1	Rattus norvegicus
F	4.5	%	Mus musculus
T1/2	1.217	hr	Homo sapiens
T1/2	0.04	hr	Mus musculus
T1/2	0.62	hr	Mus musculus
T1/2	3.2	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Sodium/hydrogen exchanger 1	IC50	=	0.19	nM	9.72	Inhibition of human NHE-1	37300915
Sodium/hydrogen exchanger 1	Ki	=	13.0	nM	7.89	Inhibition of rat NHE1 expressed in chinese hamster AP1 cells assessed as inhibi...	-
Sodium/hydrogen exchanger 1	Ki	=	13.0	nM	7.89	Inhibition of rat NHE-1	-
Sodium/hydrogen exchanger 1	IC50	=	171.0	nM	6.77	Inhibition of rat NHE1 expressed in Chinese hamster ovary cells (AP-1) measured ...	38246115
Adenosine A2 receptor	IC50	=	270.0	nM	6.57	Displacement of [3H]ZM-241,385 from human N-terminal FLAG-tagged adenosine A2A r...	27124340
Sodium/hydrogen exchanger 5	Ki	=	370.0	nM	6.43	Inhibition of full length human C-terminal HA-tagged human NHE5 expressed in chi...	-
Sodium/hydrogen exchanger 5	Ki	=	370.0	nM	6.43	Inhibition of NHE-5 (unknown origin)	-
Unchecked	EC50	=	1340.0	nM	5.87	Inhibition of envelope protein in HCoV-229E infected in human MRC-5 cells assess...	33007557
Urokinase-type plasminogen activator	Ki	=	1356.0	nM	5.87	Inhibition of human kidney uPA using Z-Gly-Gly-Arg-AMC as substrate measured ove...	30130401
Sodium/hydrogen exchanger 5	IC50	=	1510.0	nM	5.82	Inhibition of human NHE5 transfected in chinese hamster PS120 cells measured aft...	38246115
Urokinase-type plasminogen activator	IC50	=	2400.0	nM	5.62	Inhibition of human kidney uPA using chromogenic H-D-Ile-L-Pro-L-Arg-p-nitoranil...	30130401
Sodium/hydrogen exchanger 3	Ki	=	2400.0	nM	5.62	Inhibition of rat NHE-3	-
Sodium/hydrogen exchanger 3	Ki	=	2400.0	nM	5.62	Inhibition of rat NHE3 expressed in chinese hamster AP1 cells assessed as inhibi...	-
HEK293	IC50	=	2800.0	nM	5.55	Cytotoxicity against HEK293 cells assessed as reduction in cell viability after ...	30130401
Plasmodium falciparum	IC50	=	3162.28	nM	5.5	Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr...	19734910
Sodium/hydrogen exchanger 1	IC50	=	3300.0	nM	5.48	Inhibition of NHE1 in human Platelet assessed as reduction in 22Na+ uptake	38308950
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	3300.0	nM	5.48	Inhibition of recombinant human ERG expressed in CHO cells incubated for 12 mins...	33799173
Unchecked	EC50	=	3910.0	nM	5.41	Inhibition of envelope protein in Murine hepatitis virus A59 infected in mouse L...	33007557
Plasmodium falciparum	IC50	=	3981.07	nM	5.4	Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g...	19734910
TE-5	IC50	=	4700.0	nM	5.33	Cytotoxicity against human TE-5 cells expressing NHE5 assessed as inhibition of ...	38246115

Literature References

PubMed	DOI	Target Context	# Activities
33799173	10.1016/j.bmc.2021.116116	ADMET	33
30130401	10.1021/acs.jmedchem.8b00838	Unchecked	9
19734910	10.1038/nchembio.215	Plasmodium falciparum	6
30130401	10.1021/acs.jmedchem.8b00838	Rattus norvegicus	5
27124340	10.1021/acs.jmedchem.6b00142	Adenosine receptor A2a	4
27124340	10.1021/acs.jmedchem.6b00142	Adenosine A2 receptor	4
38246115	10.1016/j.bmc.2024.117603	Unchecked	4
30130401	10.1021/acs.jmedchem.8b00838	Urokinase-type plasminogen activator	3
33799173	10.1016/j.bmc.2021.116116	No relevant target	3
19339181	10.1016/j.bmcl.2009.03.029	Acid-sensing ion channel 3	2
33007557	10.1016/j.bmc.2020.115745	Unchecked	2
38246115	10.1016/j.bmc.2024.117603	HT-1080	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
34898192	10.1021/acs.jmedchem.1c01423	Unchecked	2
30130401	10.1021/acs.jmedchem.8b00838	Vitamin K-dependent protein C	1
37300915	10.1016/j.ejmech.2023.115544	Sodium/hydrogen exchanger 1	1
30130401	10.1021/acs.jmedchem.8b00838	Trypsin	1
30130401	10.1021/acs.jmedchem.8b00838	MDA-MB-231	1
30130401	10.1021/acs.jmedchem.8b00838	HepG2	1
27124340	10.1021/acs.jmedchem.6b00142	Unchecked	1

Data from ChEMBL 36 via Core Engine