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Compound Detail

CHEMBL3040038

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CCc1nc(N)nc(N)c1OCCCOc1ccccc1CCC(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3040038
Phase Preclinical
Structure Type MOL
InChI Key VDGXZSSDCDPCRF-UHFFFAOYSA-N
4
Targets
16
Activities
3
Assay Types
5
PK Parameters
19
Publications
0
Known Names

Molecular Properties

360.4
MW (Da)
2.07
ALogP
7
HBA
3
HBD
133.6
PSA (Ų)
0.55
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H24N4O4
MW 360.41
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -0.36

Activity Summary

Ki 9 meas. best 9.37
IC50 6 meas. best 8.34
EC50 1 meas. best 7.25

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 9.37 9.37 0.4 2
Unchecked
CHEMBL612545
 Ki 9.27 9.075 0.5 4
Plasmodium falciparum
CHEMBL364
 IC50 8.34 7.888 4.6 5
Dihydrofolate reductase
CHEMBL202
 Ki 7.76 7.0233 17.4 3
Unchecked
CHEMBL612545
 IC50 7.26 7.26 55.5 1
Plasmodium falciparum
CHEMBL364
 EC50 7.25 7.25 56.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Rattus norvegicus
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Rattus norvegicus
T1/2 20.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.43 nM 9.37 Inhibition of wild type Plasmodium falciparum DHFR using DHF as substrate assess... 37731689
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.43 nM 9.37 Inhibition of wild type Plasmodium falciparum DHFR 39026651
Unchecked Ki = 0.54 nM 9.27 Binding affinity to Plasmodium falciparum quadruple mutant DHFR assessed as inhi... 33131885
Unchecked Ki = 0.54 nM 9.27 Inhibition of Plasmodium falciparum DHFR N51I/C59R/S108N/I164L quadruple mutant ... 37731689
Unchecked Ki = 0.54 nM 9.27 Inhibition of Plasmodium falciparum DHFR N51I/C59R/S108N/I164L quadruple mutant 39026651
Unchecked Ki = 3.2 nM 8.49 Inhibition of recombinant Mycobacterium ulcerans N-terminal His-tagged DHFR expr... 34046602
Plasmodium falciparum IC50 = 4.6 nM 8.34 Antimalarial activity against wildtype Plasmodium falciparum TM4 33131885
Plasmodium falciparum IC50 = 5.0 nM 8.3 Antiplasmodial activity against PYR-sensitive Plasmodium falciparum TM4/8.2 enco... 37731689
Plasmodium falciparum IC50 = 5.0 nM 8.3 Antimalarial activity against PYR-sensitive Plasmodium falciparum TM4/8.2 expres... 39026651
Dihydrofolate reductase Ki = 17.41 nM 7.76 Inhibition of human DHFR using DHF as substrate assessed as inhibition constant ... 37731689
Dihydrofolate reductase Ki = 17.41 nM 7.76 Inhibition of human DHFR 39026651
Unchecked IC50 = 55.5 nM 7.26 Inhibition of recombinant Mycobacterium ulcerans N-terminal His-tagged DHFR expr... 34046602
Plasmodium falciparum EC50 = 56.0 nM 7.25 Antimalarial activity against Plasmodium falciparum V1/S harboring DHFR N51I+C59... -
Plasmodium falciparum IC50 = 56.0 nM 7.25 Antiplasmodial activity against PYR-resistant Plasmodium falciparum V1/S encodin... 37731689
Plasmodium falciparum IC50 = 56.0 nM 7.25 Antimalarial activity against PYR-resistant Plasmodium falciparum V1/S expressin... 39026651
Dihydrofolate reductase Ki = 2800.0 nM 5.55 Inhibition of human DHFR 34046602

Literature References

PubMed DOI Target Context # Activities
39026651 10.1039/d4md00197d No relevant target 5
37731689 10.1039/d3md00242j No relevant target 5
39026651 10.1039/d4md00197d ADMET 4
34046602 10.1039/d0md00303d Unchecked 3
37731689 10.1039/d3md00242j ADMET 3
37731689 10.1039/d3md00242j Plasmodium falciparum 2
39026651 10.1039/d4md00197d Plasmodium falciparum 2
33131885 10.1016/j.ejmech.2020.112955 Plasmodium falciparum 1
33131885 10.1016/j.ejmech.2020.112955 Unchecked 1
37731689 10.1039/d3md00242j Bifunctional dihydrofolate reductase-thymidylate synthase 1
33131885 10.1016/j.ejmech.2020.112955 No relevant target 1
37731689 10.1039/d3md00242j Vero 1
37731689 10.1039/d3md00242j Unchecked 1
37731689 10.1039/d3md00242j Dihydrofolate reductase 1
39026651 10.1039/d4md00197d Bifunctional dihydrofolate reductase-thymidylate synthase 1
39026651 10.1039/d4md00197d Unchecked 1
39026651 10.1039/d4md00197d Dihydrofolate reductase 1
34046602 10.1039/d0md00303d Dihydrofolate reductase 1
- 10.1039/C6MD00084C Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine