Compound Detail

CHEMBL301735

HOECHST 33258

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CN1CCN(c2ccc3[nH]c(-c4ccc5[nH]c(-c6ccc(O)cc6)nc5c4)nc3c2)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL301735
Name	HOECHST 33258
Phase	Preclinical
Structure Type	MOL
InChI Key	INAAIJLSXJJHOZ-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

424.5

MW (Da)

4.23

ALogP

HBA

HBD

84.1

PSA (Å²)

0.40

QED

Ro5 Violations

Rot. Bonds

First in Class Prodrug

IC50 11 meas. best 6.0

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Nucleic Acid CHEMBL345	IC50	6.0	6.0	1000.0	1
P388 CHEMBL389	IC50	5.92	5.92	1200.0	1
A2780cisR CHEMBL614023	IC50	5.02	5.02	9500.0	1
A2780 CHEMBL614004	IC50	4.92	4.92	12000.0	1
U-937 CHEMBL612794	IC50	4.81	4.81	15420.0	1
Unchecked CHEMBL612545	IC50	4.71	4.71	19500.0	1
DNA topoisomerase 1 CHEMBL1781	IC50	4.64	4.64	22860.0	1
CH1 CHEMBL614455	IC50	4.58	4.58	26500.0	1
DNA topoisomerase 2-alpha CHEMBL1806	IC50	4.54	4.54	28920.0	1
HL-60 CHEMBL383	IC50	4.49	4.49	32430.0	1
HeLa CHEMBL399	IC50	4.29	4.29	51310.0	1

Parameter	Value	Units	Species
Ka	0.264	uM	-
Ka	1.3	M-1	-
Ka	1.68e-08	M-1	-
Ka	4.1e-08	M-1	-
Ka	5.2e-08	M-1	-

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Nucleic Acid	IC50	=	1000.0	nM	6.0	Inhibitory concentration required to displace DNA-bound ethidium bromide molecul...	15341939
P388	IC50	=	1200.0	nM	5.92	Concentration of the drug to inhibit wild type P388 murine leukemia cell growth ...	7527862
A2780cisR	IC50	=	9500.0	nM	5.02	Antitumor activity of compound for 96-h exposure in A2780cisR (acquired resistan...	11170623
A2780	IC50	=	12000.0	nM	4.92	Antitumor activity of compound for 96-h exposure in A2780 human ovarian cell lin...	11170623
U-937	IC50	=	15420.0	nM	4.81	Cytotoxicity against human U937 cells after 72 hrs by MTT assay	22959518
Unchecked	IC50	=	19500.0	nM	4.71	Inhibition of Escherichia coli DNA topoisomerase-1 using supercoiled pBAD-GFPuv ...	25083189
DNA topoisomerase 1	IC50	=	22860.0	nM	4.64	Inhibition of human DNA topoisomerase-1 using supercoiled pBAD-GFPuv plasmid DNA...	25083189
CH1	IC50	=	26500.0	nM	4.58	Antitumor activity of compound for 96-h exposure in CH1 human ovarian cell line	11170623
DNA topoisomerase 2-alpha	IC50	=	28920.0	nM	4.54	Inhibition of human DNA topoisomerase-2 using supercoiled pBAD-GFPuv plasmid DNA...	25083189
HL-60	IC50	=	32430.0	nM	4.49	Cytotoxicity against human HL60 cells after 72 hrs by MTT assay	22959518
HeLa	IC50	=	51310.0	nM	4.29	Cytotoxicity against human HeLa cells after 72 hrs by MTT assay	22959518

PubMed	DOI	Target Context	# Activities
27301676	10.1016/j.bmc.2016.06.010	Candida albicans	11
21227551	10.1016/j.ejmech.2010.12.010	HeLa	10
19231203	10.1016/j.bmc.2009.01.071	HeLa	7
11472203	10.1021/jm0100943	Nucleic Acid	6
1738139	10.1021/jm00081a003	Nucleic Acid	4
8510102	10.1021/jm00064a008	Nucleic Acid	4
18052116	10.1021/jm701207m	DNA	3
15177454	10.1016/j.bmcl.2004.04.055	Unchecked	3
7527862	10.1021/jm00051a010	Mus musculus	2
20965737	10.1016/j.bmc.2010.09.017	Dual specificity mitogen-activated protein kinase kinase 5	2
20064676	10.1016/j.ejmech.2009.12.047	Nucleic Acid	2
25083189	10.1039/c4md00140k	DNA topoisomerase 1	2
15341939	10.1016/j.bmcl.2004.07.043	Nucleic Acid	2
15177454	10.1016/j.bmcl.2004.04.055	Telomerase reverse transcriptase	2
25083189	10.1039/c4md00140k	Escherichia coli	2
25083189	10.1039/c4md00140k	Unchecked	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
20965737	10.1016/j.bmc.2010.09.017	Dual specificity mitogen-activated protein kinase kinase; MEK1/2	2
25083189	10.1039/c4md00140k	Staphylococcus aureus	2
20965737	10.1016/j.bmc.2010.09.017	NON-PROTEIN TARGET	2

Data from ChEMBL 36 via Core Engine