Compound Detail

CHEMBL376180

AMINOPTERIN

🧪 Phase II

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🧪 Phase II

Nc1nc(N)c2nc(CNc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cnc2n1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL376180
Name	AMINOPTERIN
Phase	Phase II
Structure Type	MOL
InChI Key	TVZGACDUOSZQKY-LBPRGKRZSA-N

Known Names

4-amino-pga 4-aminofolic acid 4-aminopteroic acid Aminopterin Aminopteroylglutamic acid Aminotrexate Methotrexate related compound b NSC-739

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

440.4

MW (Da)

0.24

ALogP

HBA

HBD

219.3

PSA (Å²)

0.26

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

USAN Stem

-pterin

Extended Properties

Molecular Formula	C19H20N8O5
MW	440.42
Aromatic Rings	3
Heavy Atoms	32
NP-Likeness	-0.44

Indications

Arthritis, Rheumatoid Endometrial Neoplasms Leukemia Precursor Cell Lymphoblastic Leukemia-Lymphoma Psoriasis

Activity Summary

IC50 63 meas. best 9.21

Ki 13 meas. best 10.05

EC50 2 meas. best 8.74

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Escherichia coli CHEMBL354	Ki	10.05	10.05	0.1	1
Lacticaseibacillus casei CHEMBL613075	Ki	9.96	9.96	0.1	1
Unchecked CHEMBL612545	Ki	9.74	9.74	0.2	1
Dihydrofolate reductase CHEMBL202	Ki	9.68	9.68	0.2	1
L1210 CHEMBL386	IC50	9.21	7.9581	0.6	16
Homo sapiens CHEMBL372	IC50	9.0	7.75	1.0	2
CCRF-CEM CHEMBL382	IC50	9.0	7.48	1.0	6
Molecular identity unknown CHEMBL612546	IC50	8.8	8.0983	1.6	6
L1210 CHEMBL386	EC50	8.74	8.74	1.8	1
Dihydrofolate reductase CHEMBL4564	IC50	8.7	7.73	2.0	6
Detroit 98 CHEMBL614059	IC50	8.7	8.7	2.0	1
L cells CHEMBL612266	IC50	8.64	8.64	2.3	1
HL-60 CHEMBL383	IC50	8.6	8.56	2.5	2
Dihydrofolate reductase CHEMBL202	IC50	8.52	7.7933	3.0	6
HeLa CHEMBL399	IC50	8.44	8.26	3.6	2
SCC-7 CHEMBL614147	IC50	8.4	8.4	4.0	1
HuTu80 CHEMBL614582	EC50	8.33	8.33	4.7	1
Dihydrofolate reductase CHEMBL2902	IC50	8.3	8.3	5.0	1
SCC-25 CHEMBL614901	IC50	8.16	8.16	6.9	1
Unchecked CHEMBL612545	IC50	8.15	7.96	7.0	3
NON-PROTEIN TARGET CHEMBL3879801	IC50	8.15	8.15	7.1	1
Dihydrofolate reductase CHEMBL1809	IC50	7.96	7.96	11.0	1
SARS-CoV-2 CHEMBL4303835	IC50	6.46	6.46	350.0	2
Solute carrier organic anion transporter family member 1A3 CHEMBL2073707	Ki	6.3	6.3	500.0	1
L1210 CHEMBL386	Ki	5.92	5.92	1200.0	1
Ehrlich CHEMBL614641	Ki	5.69	5.69	2050.0	1
Plasmodium falciparum CHEMBL364	IC50	4.9	4.85	12589.2	2
Folylpolyglutamate synthase, mitochondrial CHEMBL2890	Ki	4.75	4.75	17600.0	1
L1210 ( R81) CHEMBL614710	IC50	4.08	4.08	84000.0	3

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Escherichia coli	Ki	=	0.09	nM	10.05	Inhibition constant (Ki) was determined in Escherichia coli	6410066
Lacticaseibacillus casei	Ki	=	0.11	nM	9.96	Inhibition constant (Ki) was determined in Lactobacillus casei	6410066
Unchecked	Ki	=	0.18	nM	9.74	Inhibition of Mycobacterium smegmatis ATCC 607 dihydrofolic reductase	31103404
Dihydrofolate reductase	Ki	=	0.21	nM	9.68	Inhibitory activity against Leu22-Phe mutant human Dihydrofolate reductase	7877140
L1210	IC50	=	0.61	nM	9.21	Inhibitory concentration of compound in growth of L-1210 cells	6793726
L1210	IC50	=	0.72	nM	9.14	Compound was evaluated for inhibitory effect on growth of L1210 cells at IC50 (n...	2423690
CCRF-CEM	IC50	=	1.0	nM	9.0	Tested for cell-growth inhibition against human leukemic lymphoblast CEM cells	2898531
Homo sapiens	IC50	=	1.0	nM	9.0	Compound was tested for its inhibitory concentration against human leukemic lymp...	3462394
CCRF-CEM	IC50	=	1.0	nM	9.0	Cell growth inhibition against CEM cell from human leukemic lymphoblasts	3872941
L1210	IC50	=	1.2	nM	8.92	In vitro inhibition of L1210 cell growth in rodent neoplastic cells	7108907
Molecular identity unknown	IC50	=	1.6	nM	8.8	Cell growth inhibition against human squamous cell carcinoma (SCC25) line	3872941
L1210	EC50	=	1.8	nM	8.74	Inhibition of growth (cytotoxicity) of L1210 cell line in vitro	6410066
L1210	IC50	=	2.0	nM	8.7	Compound was evaluated for the growth inhibition of L1210 cells.	1995880
Detroit 98	IC50	=	2.0	nM	8.7	Evaluated in vitro for ability to inhibit the Detroit 98 cell lines	2299624
L1210	IC50	=	2.0	nM	8.7	Compound was evaluated for cell growth inhibition of murine (L1210) leukemic cel...	1992122
L1210	IC50	=	2.0	nM	8.7	Tested for cell-growth inhibition against mouse leukemic L1210 cells	2898531
L1210	IC50	=	2.0	nM	8.7	Compound was tested for its inhibitory concentration to inhibit the growth of wi...	3462394
L1210	IC50	=	2.0	nM	8.7	Cell growth inhibition against mouse leukemia L1210 cells	3872941
L1210	IC50	=	2.0	nM	8.7	Compound was tested for its ability to inhibit growth of L1210 mouse leukemia ce...	2871191
L1210	IC50	=	2.0	nM	8.7	Ability to inhibit L1210 murine leukemia tumor cell growth in culture after 48 h...	1992118

Literature References

PubMed	DOI	Target Context	# Activities
6546949	10.1021/jm00371a008	Mus musculus	12
3462394	10.1021/jm00159a023	Mus musculus	6
-	10.6019/CHEMBL4495565	SARS-CoV-2	6
3872941	10.1021/jm50001a021	Molecular identity unknown	6
2299624	10.1021/jm00164a014	L cells	5
6410066	10.1021/jm00362a019	Dihydrofolate reductase	4
2423690	10.1021/jm00156a029	L1210	4
2918496	10.1021/jm00123a001	ADMET	3
3462394	10.1021/jm00159a023	L1210	3
16078850	10.1021/jm058213s	ADMET	3
1992148	10.1021/jm00105a070	ADMET	3
7108907	10.1021/jm00349a024	L1210	3
4009615	10.1021/jm00145a012	Folylpolyglutamate synthase, mitochondrial	3
3872941	10.1021/jm50001a021	L1210	3
16279780	10.1021/jm058234m	Folylpolyglutamate synthase, mitochondrial	3
15615522	10.1021/jm040144e	Folylpolyglutamate synthase, mitochondrial	3
2738886	10.1021/jm00127a019	Folylpolyglutamate synthase, mitochondrial	3
29605999	10.1021/acs.jmedchem.7b01775	Mus musculus	3
7877140	10.1021/jm00005a002	Dihydrofolate reductase	3
8035423	10.1021/jm00040a008	Dihydrofolate reductase	3

Data from ChEMBL 36 via Core Engine