Compound Detail

CHEMBL5593587

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CCOc1cc2c3ccc(OC)c(OC)c3c[n+](C)c2c2cc3c(cc12)OCO3

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL5593587
Phase	Preclinical
Structure Type	MOL
InChI Key	UJVQDDLAYPRWNM-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

392.4

MW (Da)

4.12

ALogP

HBA

HBD

50.0

PSA (Å²)

0.39

QED

Ro5 Violations

Rot. Bonds

Drug Information

Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C23H22NO5+
MW	392.43
Aromatic Rings	4
Heavy Atoms	29
NP-Likeness	0.69

Activity Summary

EC50 10 meas. best 6.46

IC50 4 meas. best 6.4

Kd 4 meas. best 6.18

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
dsDNA CHEMBL3832741	EC50	6.46	5.922	350.0	10
PC-3 CHEMBL390	IC50	6.4	6.4	400.0	1
A2780/Taxol CHEMBL4483224	IC50	6.4	6.4	400.0	1
A549/TR CHEMBL4483226	IC50	6.4	6.4	400.0	1
LoVo CHEMBL614721	IC50	6.4	6.4	400.0	1
quadruplex DNA CHEMBL3832742	Kd	6.18	5.5825	660.0	4

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
dsDNA	EC50	=	350.0	nM	6.46	Binding affinity to double stranded DNA ssab1 (unknown origin) incubated for 0.5...	39213483
LoVo	IC50	=	400.0	nM	6.4	Antiproliferative activity against human LoVo cells assessed as reduction in cel...	39213483
A2780/Taxol	IC50	=	400.0	nM	6.4	Antiproliferative activity against human A2780T cells assessed as reduction in c...	39213483
A549/TR	IC50	=	400.0	nM	6.4	Antiproliferative activity against human A549/Taxol cells assessed as reduction ...	39213483
PC-3	IC50	=	400.0	nM	6.4	Antiproliferative activity against human PC-3 cells assessed as reduction in cel...	39213483
quadruplex DNA	Kd	=	660.0	nM	6.18	Displacement of ThT from human G4-quadruplex Bcl2 DNA 5'- CGGGCGCGGGAGGAAGGGGGCG...	39213483
dsDNA	EC50	=	800.0	nM	6.1	Binding affinity to double stranded DNA ssab2 (unknown origin) incubated for 0.5...	39213483
dsDNA	EC50	=	1030.0	nM	5.99	Binding affinity to double stranded DNA ssab (unknown origin) incubated for 0.5 ...	39213483
dsDNA	EC50	=	1070.0	nM	5.97	Binding affinity to double stranded DNA ssab3 (unknown origin) incubated for 0.5...	39213483
dsDNA	EC50	=	1090.0	nM	5.96	Binding affinity to double stranded DNA AT15-6AT (unknown origin) incubated for ...	39213483
dsDNA	EC50	=	1160.0	nM	5.94	Binding affinity to double stranded DNA AT15-4AT (unknown origin) incubated for ...	39213483
quadruplex DNA	Kd	=	1180.0	nM	5.93	Binding affinity to human G4-quadruplex KRAS DNA 5'- AGGGCGGTGTGGGAAGAGGGAAGAGGG...	39213483
dsDNA	EC50	=	1260.0	nM	5.9	Binding affinity to double stranded DNA AT15 (unknown origin) incubated for 0.5 ...	39213483
dsDNA	EC50	=	1330.0	nM	5.88	Binding affinity to double stranded DNA AT15-2AT (unknown origin) incubated for ...	39213483
dsDNA	EC50	=	2800.0	nM	5.55	Binding affinity to double stranded DNA AT12 (unknown origin) incubated for 0.5 ...	39213483
dsDNA	EC50	=	3350.0	nM	5.47	Binding affinity to double stranded DNA AT17 (unknown origin) incubated for 0.5 ...	39213483
quadruplex DNA	Kd	=	7380.0	nM	5.13	Binding affinity to human G4-quadruplex Bcl2 DNA 5'- CGGGCGCGGGAGGAAGGGGGCGGGAGC...	39213483
quadruplex DNA	Kd	=	8040.0	nM	5.09	Binding affinity to human G4-quadruplex Pu27 DNA 5'- TGGGGAGGGTGGGGAGGGTGGGGAAGG...	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
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

Data from ChEMBL 36 via Core Engine