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Compound Detail

CHEMBL13045

CHELERYTHRINE
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COc1ccc2c(c[n+](C)c3c4cc5c(cc4ccc23)OCO5)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL13045
Name CHELERYTHRINE
Phase Preclinical
Structure Type MOL
InChI Key LLEJIEBFSOEYIV-UHFFFAOYSA-N
20
Targets
40
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

348.4
MW (Da)
3.72
ALogP
4
HBA
0
HBD
40.8
PSA (Ų)
0.41
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 C21H18NO4+
MW 348.38
Aromatic Rings 4
Heavy Atoms 26
NP-Likeness 0.96

Activity Summary

IC50 23 meas. best 7.52
EC50 12 meas. best 6.01
Kd 4 meas. best 6.07
Ki 1 meas. best 6.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Leishmania amazonensis
CHEMBL612877
 IC50 7.52 7.52 30.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
 Ki 6.66 6.66 220.0 1
LoVo
CHEMBL614721
 IC50 6.4 6.4 400.0 1
A549/TR
CHEMBL4483226
 IC50 6.4 6.4 400.0 1
PC-3
CHEMBL390
 IC50 6.4 6.4 400.0 1
A2780/Taxol
CHEMBL4483224
 IC50 6.4 6.4 400.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 6.26 6.26 550.0 1
Peroxisome proliferator-activated receptor gamma
CHEMBL235
 IC50 6.25 6.25 566.0 2
quadruplex DNA
CHEMBL3832742
 Kd 6.07 5.64 860.0 4
dsDNA
CHEMBL3832741
 EC50 6.01 5.873 970.0 10
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1
CHEMBL4693
 IC50 5.92 5.92 1200.0 1
Acetylcholinesterase
CHEMBL220
 IC50 5.84 5.84 1450.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.83 5.365 1490.0 2
Unchecked
CHEMBL612545
 IC50 5.82 5.4767 1500.0 3
quadruplex DNA
CHEMBL3832742
 EC50 5.59 5.51 2590.0 2
NCI-H1299
CHEMBL612255
 IC50 5.37 5.37 4280.0 1
HUVEC
CHEMBL613979
 IC50 5.31 5.31 4930.0 1
NCI-H292
CHEMBL614733
 IC50 5.3 5.3 4960.0 1
NCI-H460
CHEMBL396
 IC50 5.29 5.29 5140.0 1
A549
CHEMBL392
 IC50 5.11 5.11 7730.0 1
Cholinesterase
CHEMBL1914
 IC50 5.07 5.07 8580.0 1
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1
CHEMBL3136
 IC50 4.57 4.57 27000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Leishmania amazonensis IC50 = 30.0 nM 7.52 Antiprotozoal activity against Leishmania amazonensis axenic amastigotes assesse... 37257213
Amine oxidase [flavin-containing] A Ki = 220.0 nM 6.66 Competitive inhibition of recombinant human MAO-A using kynuramine as substrate ... 29925480
PC-3 IC50 = 400.0 nM 6.4 Antiproliferative activity against human PC-3 cells assessed as reduction in cel... 39213483
A549/TR IC50 = 400.0 nM 6.4 Antiproliferative activity against human A549/Taxol cells assessed as reduction ... 39213483
A2780/Taxol IC50 = 400.0 nM 6.4 Antiproliferative activity against human A2780T cells assessed as reduction in c... 39213483
LoVo IC50 = 400.0 nM 6.4 Antiproliferative activity against human LoVo cells assessed as reduction in cel... 39213483
Amine oxidase [flavin-containing] A IC50 = 550.0 nM 6.26 Inhibition of recombinant human MAO-A using kynuramine as substrate incubated fo... 29925480
Peroxisome proliferator-activated receptor gamma IC50 = 566.0 nM 6.25 Agonist activity at PPARgamma (unknown origin) 33992930
Peroxisome proliferator-activated receptor gamma IC50 = 566.0 nM 6.25 Binding affinity to human 6xHis-tagged PPARgamma ligand binding domain (206 to 4... 27503683
quadruplex DNA Kd = 860.0 nM 6.07 Displacement of ThT from human G4-quadruplex Bcl2 DNA 5'- CGGGCGCGGGAGGAAGGGGGCG... 39213483
dsDNA EC50 = 970.0 nM 6.01 Binding affinity to double stranded DNA ssab1 (unknown origin) incubated for 0.5... 39213483
dsDNA EC50 = 1060.0 nM 5.97 Binding affinity to double stranded DNA ssab (unknown origin) incubated for 0.5 ... 39213483
dsDNA EC50 = 1060.0 nM 5.97 Binding affinity to double stranded DNA ssab2 (unknown origin) incubated for 0.5... 39213483
quadruplex DNA Kd = 1070.0 nM 5.97 Binding affinity to human G4-quadruplex KRAS DNA 5'- AGGGCGGTGTGGGAAGAGGGAAGAGGG... 39213483
dsDNA EC50 = 1090.0 nM 5.96 Binding affinity to double stranded DNA AT15-6AT (unknown origin) incubated for ... 39213483
dsDNA EC50 = 1120.0 nM 5.95 Binding affinity to double stranded DNA AT15-2AT (unknown origin) incubated for ... 39213483
dsDNA EC50 = 1130.0 nM 5.95 Binding affinity to double stranded DNA AT15 (unknown origin) incubated for 0.5 ... 39213483
dsDNA EC50 = 1150.0 nM 5.94 Binding affinity to double stranded DNA AT15-4AT (unknown origin) incubated for ... 39213483
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 IC50 = 1200.0 nM 5.92 Inhibition of rabbit skeletal muscle microsomes SERCA1a incubated for 10 mins by... 32030976
dsDNA EC50 = 1290.0 nM 5.89 Binding affinity to double stranded DNA ssab3 (unknown origin) incubated for 0.5... 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
27561984 10.1016/j.bmc.2016.07.065 Unchecked 9
27234888 10.1016/j.bmc.2016.04.059 Unchecked 9
29148767 10.1021/acs.jnatprod.7b00350 quadruplex DNA 8
29925480 10.1016/j.bmcl.2018.06.023 Amine oxidase [flavin-containing] A 6
23398362 10.1042/bj20121418 cGMP-dependent protein kinase 1 4
23398362 10.1042/bj20121418 Cyclin-dependent kinase 5/CDK5 activator 1 4
23398362 10.1042/bj20121418 Insulin receptor 4
23398362 10.1042/bj20121418 Protein kinase C beta type 4
23398362 10.1042/bj20121418 Tyrosine-protein kinase Lck 4
27887841 10.1016/j.bmcl.2016.11.031 NON-PROTEIN TARGET 4
23398362 10.1042/bj20121418 Serine/threonine-protein kinase mTOR 4
23398362 10.1042/bj20121418 Tyrosine-protein kinase HCK 4
23398362 10.1042/bj20121418 Insulin-like growth factor 1 receptor 4
29148767 10.1021/acs.jnatprod.7b00350 Calf thymus DNA 3
23398362 10.1042/bj20121418 Serine/threonine-protein kinase MARK1 2
23398362 10.1042/bj20121418 Casein kinase I isoform delta 2
23398362 10.1042/bj20121418 Death-associated protein kinase 1 2

Data from ChEMBL 36 via Core Engine