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Compound Detail

CHEMBL2323768

KOENIMBINE
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COc1ccc2[nH]c3c4c(c(C)cc3c2c1)OC(C)(C)C=C4
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2323768
Name KOENIMBINE
Phase Preclinical
Structure Type MOL
InChI Key OSERHKINMDLESD-UHFFFAOYSA-N
8
Targets
9
Activities
1
Assay Types
4
PK Parameters
14
Publications
0
Known Names

Molecular Properties

293.4
MW (Da)
4.82
ALogP
2
HBA
1
HBD
34.2
PSA (Ų)
0.70
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H19NO2
MW 293.37
Aromatic Rings 3
Heavy Atoms 22
NP-Likeness 1.69

Activity Summary

IC50 9 meas. best 6.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HCT-116
CHEMBL394
 IC50 6.7 6.7 200.0 1
HepG2
CHEMBL395
 IC50 6.7 6.7 200.0 1
HeLa
CHEMBL399
 IC50 6.7 6.7 200.0 1
DU-145
CHEMBL613508
 IC50 6.7 6.7 200.0 1
OVCAR-3
CHEMBL614213
 IC50 6.7 6.7 200.0 1
PA-1
CHEMBL614949
 IC50 6.7 6.7 200.0 1
Unchecked
CHEMBL612545
 IC50 5.92 5.92 1200.0 1
Staphylococcus aureus
CHEMBL352
 IC50 4.77 4.77 17000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2772.35 ng.hr.mL-1 Rattus norvegicus
Cmax 1810.0 nM Rattus norvegicus
T1/2 2.205 hr Rattus norvegicus
Tmax 0.83 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
PA-1 IC50 = 200.0 nM 6.7 Antiproliferative activity against human PA-1 cells assessed as cell growth inhi... 34838335
OVCAR-3 IC50 = 200.0 nM 6.7 Antiproliferative activity against human OVCAR-3 cells assessed as cell growth i... 34838335
HepG2 IC50 = 200.0 nM 6.7 Antiproliferative activity against human HepG2 cells assessed as cell growth inh... 34838335
DU-145 IC50 = 200.0 nM 6.7 Antiproliferative activity against human DU-145 cells assessed as cell growth in... 34838335
HCT-116 IC50 = 200.0 nM 6.7 Antiproliferative activity against human HCT-116 cells assessed as cell growth i... 34838335
HeLa IC50 = 200.0 nM 6.7 Antiproliferative activity against human HeLa cells assessed as cell growth inhi... 34838335
Unchecked IC50 = 1200.0 nM 5.92 Inhibition of theophylline-induced melanogenesis in mouse B16-4A5 cells after 72... 23376010
Staphylococcus aureus IC50 = 17000.0 nM 4.77 Antibacterial activity against Staphylococcus aureus assessed as inhibition of b... 37467619

Literature References

PubMed DOI Target Context # Activities
27136692 10.1021/acs.jnatprod.5b00883 ADMET 6
23376010 10.1016/j.bmc.2013.01.012 Tyrosinase 5
23376010 10.1016/j.bmc.2013.01.012 ADMET 4
23376010 10.1016/j.bmc.2013.01.012 Unchecked 4
27136692 10.1021/acs.jnatprod.5b00883 Molecular identity unknown 4
27136692 10.1021/acs.jnatprod.5b00883 NON-PROTEIN TARGET 2
27908755 10.1016/j.bmc.2016.11.031 Pancreatic triacylglycerol lipase 1
34838335 10.1016/j.ejmech.2021.113999 PA-1 1
34838335 10.1016/j.ejmech.2021.113999 OVCAR-3 1
34838335 10.1016/j.ejmech.2021.113999 HepG2 1
34838335 10.1016/j.ejmech.2021.113999 DU-145 1
34838335 10.1016/j.ejmech.2021.113999 HCT-116 1
34838335 10.1016/j.ejmech.2021.113999 HeLa 1
37467619 10.1016/j.ejmech.2023.115627 Staphylococcus aureus 1

Data from ChEMBL 36 via Core Engine