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Compound Detail

CHEMBL465295

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CC(=O)O[C@H]1[C@H]2c3cc4c(cc3CN3CCC(=C[C@@H]1OC(C)=O)[C@H]23)OCO4
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL465295
Phase Preclinical
Structure Type MOL
InChI Key LMZHAKUXAHOCST-VNTMZGSJSA-N
2
Targets
3
Activities
2
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

371.4
MW (Da)
1.89
ALogP
7
HBA
0
HBD
74.3
PSA (Ų)
0.58
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H21NO6
MW 371.39
Aromatic Rings 1
Heavy Atoms 27
NP-Likeness 2.10

Activity Summary

Ki 2 meas. best 5.0
IC50 1 meas. best 6.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 6.58 6.58 260.0 1
Cytochrome P450 3A4
CHEMBL340
 Ki 5.0 4.98 10000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 260.0 nM 6.58 Antiplasmodial activity against Plasmodium falciparum F32-Tanzania after 24 hrs 20627737
Cytochrome P450 3A4 Ki = 10000.0 nM 5.0 Inhibition of human CYP3A4 assessed as biotransformation of 7-benzyloxyquinoline 19428250
Cytochrome P450 3A4 Ki = 11000.0 nM 4.96 Inhibition of human CYP3A4 assessed as biotransformation of 7-benzyloxyquinoline 19428250

Literature References

PubMed DOI Target Context # Activities
19013823 10.1016/j.bmc.2008.10.061 Plasmodium falciparum 4
19788245 10.1021/jm901031h NON-PROTEIN TARGET 3
19013823 10.1016/j.bmc.2008.10.061 Unchecked 2
19428250 10.1016/j.bmcl.2009.04.086 Cytochrome P450 3A4 2
29033234 10.1016/j.bmcl.2017.09.052 Flavobacterium columnare 2
19788245 10.1021/jm901031h B16-F10 1
31515186 10.1016/j.bmcl.2019.126642 Trypanosoma cruzi 1
31515186 10.1016/j.bmcl.2019.126642 Trypanosoma brucei rhodesiense 1
31515186 10.1016/j.bmcl.2019.126642 Trichomonas vaginalis 1
29033234 10.1016/j.bmcl.2017.09.052 Staphylococcus aureus 1
29033234 10.1016/j.bmcl.2017.09.052 Edwardsiella ictaluri 1
20655219 10.1016/j.bmcl.2010.06.130 Acetylcholinesterase 1
20627737 10.1016/j.bmc.2010.05.023 Plasmodium falciparum 1
19299148 10.1016/j.bmc.2009.02.050 Plasmodium falciparum 1
19013823 10.1016/j.bmc.2008.10.061 Trypanosoma brucei brucei 1
19788245 10.1021/jm901031h SK-MEL-28 1
19788245 10.1021/jm901031h A549 1
19013823 10.1016/j.bmc.2008.10.061 Trypanosoma brucei rhodesiense 1
19013823 10.1016/j.bmc.2008.10.061 MRC5 1

Data from ChEMBL 36 via Core Engine