Compound Detail

CHEMBL563608

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Cc1cn(-c2ccc(C(N)=O)c(N[C@H]3CC[C@H](O)CC3)c2)c2c1C(=O)CC(C)(C)C2

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL563608
Phase	Preclinical
Structure Type	MOL
InChI Key	SIEDNUHWSIZMAF-JCNLHEQBSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

409.5

MW (Da)

3.76

ALogP

HBA

HBD

97.3

PSA (Å²)

0.72

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C24H31N3O3
MW	409.53
Aromatic Rings	2
Heavy Atoms	30
NP-Likeness	-0.59

Activity Summary

IC50 15 meas. best 8.52

EC50 2 meas. best 6.0

Kd 1 meas. best 7.57

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
K562 CHEMBL385	IC50	8.52	8.52	3.0	1
LNCaP CHEMBL612518	IC50	8.4	8.4	4.0	1
SW-620 CHEMBL612262	IC50	8.22	8.22	6.0	1
Heat shock protein HSP90 CHEMBL2095165	IC50	8.15	7.24	7.0	4
HT-29 CHEMBL384	IC50	8.15	8.15	7.0	1
SK-MEL-5 CHEMBL614922	IC50	8.15	8.15	7.0	1
A-375 CHEMBL613859	IC50	8.05	8.05	9.0	1
MCF7 CHEMBL387	IC50	8.0	8.0	10.0	1
MDA-MB-231 CHEMBL400	IC50	8.0	8.0	10.0	1
PC-3 CHEMBL390	IC50	7.85	7.85	14.0	1
Unchecked CHEMBL612545	Kd	7.57	7.57	27.0	1
HCT-15 CHEMBL612263	IC50	7.21	7.21	61.0	1
NCI-H460 CHEMBL396	IC50	6.61	6.61	248.0	1
Human alphaherpesvirus 2 CHEMBL370	EC50	6.0	6.0	1000.0	1
Human alphaherpesvirus 1 CHEMBL377	EC50	5.99	5.99	1030.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
F	10.0	%	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
K562	IC50	=	3.0	nM	8.52	Antiproliferative activity against human K562 cells after 72 to 144 hrs by cyqua...	19552433
LNCaP	IC50	=	4.0	nM	8.4	Antiproliferative activity against human LNCAP cells after 72 to 144 hrs by cyqu...	19552433
SW-620	IC50	=	6.0	nM	8.22	Antiproliferative activity against human SW620 cells after 72 to 144 hrs by cyqu...	19552433
HT-29	IC50	=	7.0	nM	8.15	Antiproliferative activity against human HT-29 cells after 72 to 144 hrs by cyqu...	19552433
SK-MEL-5	IC50	=	7.0	nM	8.15	Antiproliferative activity against human SK-MEL-5 cells after 72 to 144 hrs by c...	19552433
Heat shock protein HSP90	IC50	=	7.0	nM	8.15	Inhibition of Hsp90 in human A375 cells assessed as pS6 degradation after 24 hrs...	19552433
A-375	IC50	=	9.0	nM	8.05	Antiproliferative activity against human A375 cells after 72 to 144 hrs by cyqua...	19552433
MCF7	IC50	=	10.0	nM	8.0	Antiproliferative activity against human MCF7 cells after 72 to 144 hrs by cyqua...	19552433
MDA-MB-231	IC50	=	10.0	nM	8.0	Antiproliferative activity against human MDA-MB-231 cells after 72 to 144 hrs by...	19552433
PC-3	IC50	=	14.0	nM	7.85	Antiproliferative activity against human PC3 cells after 72 to 144 hrs by cyquan...	19552433
Heat shock protein HSP90	IC50	=	14.0	nM	7.85	Inhibition of Hsp90 in human A375 cells assessed as Hsp70 induction after 24 hrs...	19552433
Heat shock protein HSP90	IC50	=	16.0	nM	7.8	Inhibition of Hsp90 in human AU565 cells assessed as pERK degradation after 24 h...	19552433
Unchecked	Kd	=	27.0	nM	7.57	Binding affinity to pig spleen Hsp90 ATPase pocket by Bradford assay	19552433
HCT-15	IC50	=	61.0	nM	7.21	Antiproliferative activity against human HCT15 cells after 72 to 144 hrs by cyqu...	19552433
NCI-H460	IC50	=	248.0	nM	6.61	Antiproliferative activity against human NCI-H460 cells after 72 to 144 hrs by c...	19552433
Human alphaherpesvirus 2	EC50	=	1000.0	nM	6.0	Antiviral activity against HSV2 strain 333 infected in african green monkey Vero...	22704890
Human alphaherpesvirus 1	EC50	=	1030.0	nM	5.99	Antiviral activity against HSV1 strain F ATCC VR733 infected in african green mo...	22704890
Heat shock protein HSP90	IC50	=	7000.0	nM	5.16	Inhibition of Hsp90 in human AU565 cells assessed as Her2 degradation after 24 h...	19552433

Literature References

PubMed	DOI	Target Context	# Activities
22704890	10.1016/j.bmcl.2012.05.079	Human alphaherpesvirus 1	7
19552433	10.1021/jm900230j	Heat shock protein HSP90	4
22704890	10.1016/j.bmcl.2012.05.079	Human alphaherpesvirus 2	3
22704890	10.1016/j.bmcl.2012.05.079	Unchecked	2
22704890	10.1016/j.bmcl.2012.05.079	Vero	1
19552433	10.1021/jm900230j	Unchecked	1
22704890	10.1016/j.bmcl.2012.05.079	MRC5	1
19552433	10.1021/jm900230j	Rattus norvegicus	1
19552433	10.1021/jm900230j	K562	1
19552433	10.1021/jm900230j	HCT-15	1
19552433	10.1021/jm900230j	NCI-H460	1
19552433	10.1021/jm900230j	MDA-MB-231	1
19552433	10.1021/jm900230j	PC-3	1
19552433	10.1021/jm900230j	SK-MEL-5	1
19552433	10.1021/jm900230j	SW-620	1
19552433	10.1021/jm900230j	HT-29	1
19552433	10.1021/jm900230j	MCF7	1
19552433	10.1021/jm900230j	LNCaP	1
19552433	10.1021/jm900230j	A-375	1

Data from ChEMBL 36 via Core Engine