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Compound Detail

CHEMBL22327

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COc1cc(Cc2cnc(N)nc2N)ccc1OCCCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL22327
Phase Preclinical
Structure Type MOL
InChI Key IJXHTJRYJGZEDE-UHFFFAOYSA-N
4
Targets
12
Activities
2
Assay Types
0
PK Parameters
7
Publications
0
Known Names

Molecular Properties

364.4
MW (Da)
3.25
ALogP
6
HBA
2
HBD
96.3
PSA (Ų)
0.60
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H24N4O2
MW 364.45
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -0.23

Activity Summary

Ki 7 meas. best 8.74
IC50 5 meas. best 5.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.74 7.32 1.8 7
Plasmodium falciparum
CHEMBL364
 IC50 5.52 5.52 3000.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 4.93 4.93 11700.0 1
BC
CHEMBL613535
 IC50 4.5 4.5 32000.0 1
KB
CHEMBL398
 IC50 4.14 4.14 72000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.8 nM 8.74 Inhibitory activity against wild-type dihydrofolate reductase (S108N DHFR) 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.8 nM 8.74 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 26.6 nM 7.58 Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 44.2 nM 7.36 Inhibitory activity against double mutant dihydrofolate reductase (C59R+S108N DH... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 44.2 nM 7.36 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1122.8 nM 5.95 Inhibitory activity against quadruple mutant dihydrofolate reductase (N51I C59R ... 14711307
Plasmodium falciparum IC50 = 3000.0 nM 5.52 In vitro antiplasmodial activity (IC50) against Plasmodium falciparum wtTM4/8.2 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 3100.2 nM 5.51 Inhibitory activity against triple mutant dihydrofolate reductase (C59R S108N I1... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 11700.0 nM 4.93 Antiplasmodial activity IC50 against Plasmodium falciparum K1CB1 DHFR double-mut... 11881993
BC IC50 = 32000.0 nM 4.5 Cytotoxicity against human breast cancer cells. 11881993
KB IC50 = 72000.0 nM 4.14 Cytotoxicity against human epidermoid carcinoma KB cell. 11881993

Literature References

PubMed DOI Target Context # Activities
11881993 10.1021/jm010131q Bifunctional dihydrofolate reductase-thymidylate synthase 9
14711307 10.1021/jm0303352 Bifunctional dihydrofolate reductase-thymidylate synthase 8
11881993 10.1021/jm010131q NON-PROTEIN TARGET 5
11881993 10.1021/jm010131q Plasmodium falciparum 3
11881993 10.1021/jm010131q Vero 1
11881993 10.1021/jm010131q KB 1
11881993 10.1021/jm010131q BC 1

Data from ChEMBL 36 via Core Engine