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Compound Detail

CHEMBL362071

COPTISINE
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c1c2c(cc3c1OCO3)-c1cc3ccc4c(c3c[n+]1CC2)OCO4
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL362071
Name COPTISINE
Phase Preclinical
Structure Type MOL
InChI Key XYHOBCMEDLZUMP-UHFFFAOYSA-N
5
Targets
26
Activities
3
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

320.3
MW (Da)
2.81
ALogP
4
HBA
0
HBD
40.8
PSA (Ų)
0.60
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 C19H14NO4+
MW 320.32
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness 1.44

Activity Summary

EC50 13 meas. best 5.77
Kd 8 meas. best 6.46
IC50 5 meas. best 5.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
quadruplex DNA
CHEMBL3832742
 Kd 6.46 5.7888 350.0 8
dsDNA
CHEMBL3832741
 EC50 5.77 5.1964 1690.0 11
Unchecked
CHEMBL612545
 IC50 5.74 5.17 1830.0 2
quadruplex DNA
CHEMBL3832742
 EC50 5.23 5.075 5930.0 2
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 IC50 5.2 5.2 6300.0 1
Neuraminidase
CHEMBL3559643
 IC50 4.6 4.59 25300.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
quadruplex DNA Kd = 350.0 nM 6.46 Displacement of ThT from human G4-quadruplex Bcl2 DNA 5'- CGGGCGCGGGAGGAAGGGGGCG... 39213483
quadruplex DNA Kd = 980.0 nM 6.01 Binding affinity to human G4-quadruplex Oxy28 DNA 5'- GGGGTTTTGGGGTTTTGGGGTTTTGG... 39213483
quadruplex DNA Kd = 1130.0 nM 5.95 Binding affinity to human G4-quadruplex KRAS DNA 5'- AGGGCGGTGTGGGAAGAGGGAAGAGGG... 39213483
quadruplex DNA Kd = 1150.0 nM 5.94 Binding affinity to human G4-quadruplex Bcl2 DNA 5'- CGGGCGCGGGAGGAAGGGGGCGGGAGC... 39213483
dsDNA EC50 = 1690.0 nM 5.77 Binding affinity to double stranded DNA AT15 (unknown origin) incubated for 0.5 ... 39213483
Unchecked IC50 = 1830.0 nM 5.74 Inhibition of Plasmodium falciparum recombinant DHODH incubated for 5 mins by mi... 33131885
quadruplex DNA Kd = 2170.0 nM 5.66 Binding affinity to human G4-quadruplex Pu27 DNA 5'- TGGGGAGGGTGGGGAGGGTGGGGAAGG... 39213483
quadruplex DNA Kd = 2590.0 nM 5.59 Binding affinity to human G4-quadruplex c-kit2 DNA 5'- CGGGCGGGCGCGAGGGAGGGT-3' ... 39213483
quadruplex DNA Kd = 3390.0 nM 5.47 Binding affinity to human G4-quadruplex VEGF DNA 5'- GGGCGGGCCGGGGGCGGG-3' asses... 39213483
dsDNA EC50 = 3920.0 nM 5.41 Binding affinity to double stranded DNA AT15-2AT (unknown origin) incubated for ... 39213483
dsDNA EC50 = 5570.0 nM 5.25 Binding affinity to double stranded DNA AT15-4AT (unknown origin) incubated for ... 39213483
dsDNA EC50 = 5570.0 nM 5.25 Binding affinity to double stranded DNA ssab (unknown origin) incubated for 0.5 ... 39213483
dsDNA EC50 = 5840.0 nM 5.23 Binding affinity to double stranded DNA ssab3 (unknown origin) incubated for 0.5... 39213483
quadruplex DNA EC50 = 5930.0 nM 5.23 Displacement of thiazole orange from wild-type telomeric 22 H2 G-quadruplex DNA ... 29148767
quadruplex DNA Kd = 5930.0 nM 5.23 Binding affinity to human G4-quadruplex 22AG DNA 5'- AGGGTTAGGGTTAGGGTTAGGG -3' ... 39213483
Indoleamine 2,3-dioxygenase 1 IC50 = 6300.0 nM 5.2 Inhibition of human recombinant IDO1 expressed in Escherichia coli BL21 incubate... 36917881
dsDNA EC50 = 7120.0 nM 5.15 Binding affinity to double stranded DNA AT9 (unknown origin) incubated for 0.5 h... 39213483
dsDNA EC50 = 7250.0 nM 5.14 Binding affinity to double stranded DNA ssab2 (unknown origin) incubated for 0.5... 39213483
dsDNA EC50 = 7780.0 nM 5.11 Binding affinity to double stranded DNA AT17 (unknown origin) incubated for 0.5 ... 39213483
dsDNA EC50 = 8040.0 nM 5.09 Binding affinity to double stranded DNA AT15-6AT (unknown origin) incubated for ... 39213483

Literature References

PubMed DOI Target Context # Activities
39213483 10.1021/acs.jnatprod.4c00416 quadruplex DNA 30
39213483 10.1021/acs.jnatprod.4c00416 dsDNA 15
39213483 10.1021/acs.jnatprod.4c00416 A-375 10
29148767 10.1021/acs.jnatprod.7b00350 quadruplex DNA 9
29148767 10.1021/acs.jnatprod.7b00350 Calf thymus DNA 3
31859028 10.1016/j.bmc.2019.115093 HaCaT 2
25277281 10.1016/j.bmc.2014.09.004 Neuraminidase 2
29148767 10.1021/acs.jnatprod.7b00350 Unchecked 1
33131885 10.1016/j.ejmech.2020.112955 Unchecked 1
36917881 10.1016/j.ejmech.2023.115258 Indoleamine 2,3-dioxygenase 1 1
25277281 10.1016/j.bmc.2014.09.004 Unchecked 1
39213483 10.1021/acs.jnatprod.4c00416 Salmon testes DNA 1
39213483 10.1021/acs.jnatprod.4c00416 Calf thymus DNA 1
39213483 10.1021/acs.jnatprod.4c00416 LoVo 1
39213483 10.1021/acs.jnatprod.4c00416 A2780/Taxol 1
39213483 10.1021/acs.jnatprod.4c00416 A549/TR 1
39213483 10.1021/acs.jnatprod.4c00416 PC-3 1
15743190 10.1021/jm049838d Panel NCI-60 (60 carcinoma cell lines) 1

Data from ChEMBL 36 via Core Engine