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Compound Detail

CHEMBL486179

PROTOPINE
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CN1CCc2cc3c(cc2C(=O)Cc2cc4c(cc2C1)OCO4)OCO3

Basic Information

ChEMBL ID CHEMBL486179
Name PROTOPINE
Phase Preclinical
Structure Type MOL
InChI Key ZAALQOFZFANFTF-UHFFFAOYSA-N
4
Targets
6
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

353.4
MW (Da)
2.56
ALogP
6
HBA
0
HBD
57.2
PSA (Ų)
0.73
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H19NO5
MW 353.37
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.48

Activity Summary

Kd 3 meas. best 6.14
IC50 2 meas. best 4.47
Ki 1 meas. best 7.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 2D6
CHEMBL289
Ki 7.11 7.11 78.0 1
Ileum
CHEMBL613680
Kd 6.14 5.9633 724.4 3
Plasmodium falciparum
CHEMBL364
IC50 4.47 4.47 34000.0 1
Entamoeba histolytica
CHEMBL612853
IC50 4.15 4.15 70700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
6631434 10.1021/np50028a006 Ileum 4
2904975 10.1021/np50059a043 Ileum 4
6619883 10.1021/np50027a004 Ileum 3
22024033 10.1016/j.bmcl.2011.09.128 RAW264.7 2
16562853 10.1021/np058114h 5-hydroxytryptamine receptor 1A 2
11141105 10.1021/np000144r Plasmodium falciparum 1
26125082 10.1021/acs.jmedchem.5b00417 Cytochrome P450 2D6 1
20594848 10.1016/j.bmcl.2010.06.035 HCT-15 1
20594848 10.1016/j.bmcl.2010.06.035 SK-MEL-2 1
20594848 10.1016/j.bmcl.2010.06.035 SK-OV-3 1
20594848 10.1016/j.bmcl.2010.06.035 A549 1
16562853 10.1021/np058114h Cytochrome P450 3A4 1
11141105 10.1021/np000144r KB 1
11141105 10.1021/np000144r Entamoeba histolytica 1
- 10.1021/np50007a014 Candida albicans 1
- 10.1021/np50007a014 Mycolicibacterium smegmatis 1
- 10.1021/np50007a014 Klebsiella pneumoniae 1
- 10.1021/np50007a014 Salmonella enterica subsp. enterica serovar Gallinarum 1
- 10.1021/np50007a014 Escherichia coli 1
- 10.1021/np50007a014 Staphylococcus aureus 1

Data from ChEMBL 36 via Core Engine