Compound Detail

CHEMBL422395

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C#CCN(Cc1ccc2[nH]c(N)nc(=O)c2c1)c1ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL422395
Phase	Preclinical
Structure Type	MOL
InChI Key	LTKHPMDRMUCUEB-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

477.5

MW (Da)

1.19

ALogP

HBA

HBD

178.7

PSA (Å²)

0.27

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	C24H23N5O6
MW	477.48
Aromatic Rings	3
Heavy Atoms	35
NP-Likeness	-0.62

Activity Summary

IC50 76 meas. best 9.89

Ki 9 meas. best 8.52

EC50 1 meas. best 6.14

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Enterococcus faecium CHEMBL357	IC50	9.89	9.89	0.1	1
Lacticaseibacillus casei CHEMBL613075	IC50	9.4	9.4	0.4	1
CCRF S-180 CHEMBL614027	IC50	8.71	7.235	2.0	2
L1210 CHEMBL386	IC50	8.58	5.9713	2.6	8
Thymidylate synthase CHEMBL6137	Ki	8.52	8.52	3.0	1
Thymidylate synthase CHEMBL1952	Ki	8.35	8.135	4.5	2
Thymidylate synthase CHEMBL3160	Ki	8.35	8.025	4.5	2
HL-60 CHEMBL383	IC50	8.28	8.28	5.3	1
Thymidylate synthase CHEMBL1952	IC50	8.0	7.3275	10.0	8
Unchecked CHEMBL612545	IC50	8.0	6.824	10.0	5
Thymidylate synthase CHEMBL5328	IC50	7.89	7.6083	13.0	6
Dihydrofolate reductase CHEMBL4564	Ki	7.85	7.85	14.0	1
Thymidylate synthase CHEMBL3160	IC50	7.85	6.635	14.0	8
Bifunctional dihydrofolate reductase-thymidylate synthase CHEMBL2425	IC50	7.75	6.762	18.0	5
Thymidylate synthase CHEMBL6137	IC50	7.72	7.345	19.0	4
Dihydrofolate reductase CHEMBL2902	IC50	7.66	6.0933	22.0	3
Thymidylate synthase CHEMBL2555	IC50	7.22	7.22	60.0	1
Dihydrofolate reductase CHEMBL2363	Ki	7.13	7.13	74.5	1
Thymidylate synthase CHEMBL2555	Ki	7.02	7.02	95.0	1
Dihydrofolate reductase CHEMBL202	IC50	6.52	5.6914	300.0	7
Thymidylate synthase CHEMBL4341	IC50	6.44	6.44	360.0	1
Lymphoma cell line CHEMBL614114	IC50	6.25	6.25	560.0	1
Manca CHEMBL614320	IC50	6.25	6.25	560.0	1
CCRF-CEM CHEMBL382	EC50	6.14	6.14	720.0	1
CCRF-CEM CHEMBL382	IC50	6.12	6.12	750.0	1
MCF7 CHEMBL387	IC50	6.1	6.1	800.0	1
SW480 CHEMBL612544	IC50	6.1	6.1	800.0	1
GC3/MTK- CHEMBL614157	IC50	5.85	5.76	1400.0	2
Ehrlich CHEMBL614641	IC50	5.74	5.74	1820.0	1
H35R0.3 CHEMBL614160	IC50	5.7	5.7	2000.0	1
Trifunctional purine biosynthetic protein adenosine-3 CHEMBL3690	Ki	5.22	5.22	6000.0	1
Dihydrofolate reductase CHEMBL4564	IC50	5.18	5.17	6600.0	2
Dihydrofolate reductase CHEMBL1809	IC50	4.64	4.64	23000.0	2
MOLT-4 CHEMBL614177	IC50	4.55	4.55	28000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Enterococcus faecium	IC50	=	0.13	nM	9.89	Inhibition of growth of Staphylococcus faecium	2542557
Lacticaseibacillus casei	IC50	=	0.4	nM	9.4	Inhibition of growth of Lactobacillus casei	2542557
CCRF S-180	IC50	=	1.97	nM	8.71	The compound was tested for its growth inhibitory activity against S180 cells.	1732551
L1210	IC50	=	2.61	nM	8.58	The compound was tested for its growth inhibitory activity against L1210 cells	1732551
Thymidylate synthase	Ki	=	3.0	nM	8.52	Inhibition of Thymidylate synthase of Escherichia coli (Ki)	2066965
Thymidylate synthase	Ki	=	4.5	nM	8.35	Binding affinity was evaluated against thymidylate synthase	4045922
Thymidylate synthase	Ki	=	4.5	nM	8.35	Binding affinity against human thymidylate synthase	1995868
HL-60	IC50	=	5.29	nM	8.28	The compound was tested for its growth inhibitory activity against HL60 cells.	1732551
Unchecked	IC50	=	10.0	nM	8.0	Concentration required for 50% inhibition against thymidylate synthase of Strept...	6403710
Thymidylate synthase	IC50	=	10.0	nM	8.0	Inhibition of pure human thymidylate synthase from extract of Manca human lympho...	2542557
Thymidylate synthase	IC50	=	10.0	nM	8.0	Compound was evaluated for the inhibition of human Thymidylate Synthase	1895294
Thymidylate synthase	Ki	=	12.0	nM	7.92	Inhibition of human Thymidylate synthase (Ki)	2066965
Thymidylate synthase	IC50	=	13.0	nM	7.89	Inhibitory activity against thymidylate synthase derived from Lactobacillus case...	3100797
Unchecked	IC50	=	13.0	nM	7.89	Concentration required for 50% inhibition against thymidylate synthase of Lactob...	6403710
Thymidylate synthase	IC50	=	14.0	nM	7.85	Inhibition of L1210 leukemia thymidylate synthase (TS) enzyme	2704031
Dihydrofolate reductase	Ki	=	14.0	nM	7.85	Binding affinity was evaluated against dihydrofolate reductase	4045922
Thymidylate synthase	IC50	=	14.0	nM	7.85	Inhibitory activity against thymidylate synthase isolated from L1210 leukemia ce...	3339615
Bifunctional dihydrofolate reductase-thymidylate synthase	IC50	=	18.0	nM	7.75	Inhibition of Toxoplasma gondii thymidylate synthase	16279780
Unchecked	IC50	=	19.0	nM	7.72	Inhibition of Escherichia coli thymidylate synthase	22739090
Thymidylate synthase	IC50	=	19.0	nM	7.72	Inhibition of Escherichia coli thymidylate synthase	18800768

Literature References

PubMed	DOI	Target Context	# Activities
10377217	10.1021/jm9900016	Thymidylate synthase	5
10956221	10.1021/jm000130i	Thymidylate synthase	4
2066965	10.1021/jm00111a001	Thymidylate synthase	4
8632414	10.1021/jm9502652	Thymidylate synthase	4
2918503	10.1021/jm00123a010	ADMET	4
3599032	10.1021/jm00390a025	Thymidylate synthase	3
4045922	10.1021/jm00148a016	Dihydrofolate reductase	3
4045922	10.1021/jm00148a016	Thymidylate synthase	3
3100797	10.1021/jm00157a600	Thymidylate synthase	3
2362285	10.1021/jm00169a040	L1210	3
7473577	10.1021/jm00022a015	Thymidylate synthase	2
3100797	10.1021/jm00157a600	Lacticaseibacillus casei	2
3100797	10.1021/jm00157a600	Enterococcus faecium	2
1895294	10.1021/jm00113a011	Folylpolyglutamate synthase, mitochondrial	2
2704030	10.1021/jm00124a018	No relevant target	2
6403710	10.1021/jm00358a030	Dihydrofolate reductase	2
6403710	10.1021/jm00358a030	Lacticaseibacillus casei	2
1895294	10.1021/jm00113a011	Thymidylate synthase	2
3599032	10.1021/jm00390a025	Lacticaseibacillus casei	2
3599032	10.1021/jm00390a025	Enterococcus faecium	2

Data from ChEMBL 36 via Core Engine