Compound Detail

CHEMBL198075

CRYPTOPLEURINE

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COc1ccc2c3c(c4cc(OC)c(OC)cc4c2c1)C[C@H]1CCCCN1C3

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL198075
Name	CRYPTOPLEURINE
Phase	Preclinical
Structure Type	MOL
InChI Key	RSHYSOGXGSUUIJ-OAHLLOKOSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

377.5

MW (Da)

4.93

ALogP

HBA

HBD

30.9

PSA (Å²)

0.61

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C24H27NO3
MW	377.48
Aromatic Rings	3
Heavy Atoms	28
NP-Likeness	0.39

Activity Summary

IC50 39 meas. best 9.15

EC50 1 meas. best 9.22

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Hepatitis C virus CHEMBL379	EC50	9.22	9.22	0.6	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	9.15	8.7043	0.7	7
CAKI-1 CHEMBL614067	IC50	9.07	9.07	0.9	1
MDA-MB-231 CHEMBL400	IC50	9.05	9.05	0.9	1
A549 CHEMBL392	IC50	9.03	8.77	0.9	5
HCT-116 CHEMBL394	IC50	8.98	8.98	1.0	1
A-375 CHEMBL613859	IC50	8.92	8.72	1.2	2
KB CHEMBL398	IC50	8.82	8.82	1.5	1
DU-145 CHEMBL613508	IC50	8.8	8.8	1.6	1
HCT-8 CHEMBL613510	IC50	8.72	8.72	1.9	1
PA-1 CHEMBL614949	IC50	8.7	8.7	2.0	1
Daudi CHEMBL614281	IC50	8.7	8.7	2.0	1
Unchecked CHEMBL612545	IC50	8.7	8.7	2.0	1
PC-3 CHEMBL390	IC50	8.59	8.59	2.5	1
MAT-Ly-Lu CHEMBL612579	IC50	8.52	8.52	3.0	1
Ramos CHEMBL614629	IC50	8.52	8.52	3.0	1
MES-SA CHEMBL614343	IC50	8.52	8.52	3.0	1
MCF7 CHEMBL387	IC50	8.52	8.52	3.0	1
A-431 CHEMBL614069	IC50	8.52	8.52	3.0	1
BT-20 CHEMBL613870	IC50	8.52	8.52	3.0	1
MES-SA/Dx5 CHEMBL613827	IC50	8.52	8.52	3.0	1
HCT-15 CHEMBL612263	IC50	8.52	8.52	3.0	1
HT-1376 CHEMBL612258	IC50	8.4	8.4	4.0	1
PC-9 CHEMBL614102	IC50	8.26	8.26	5.5	1
BUD-8 CHEMBL612591	IC50	8.22	8.22	6.0	1
HepG2 2.2.15 CHEMBL4296438	IC50	8.2	8.2	6.3	1
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha CHEMBL2221345	IC50	8.06	8.06	8.7	1
KHOS/NP CHEMBL612598	IC50	8.0	8.0	10.0	1
MRC5 CHEMBL614181	IC50	7.85	7.85	14.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	53.2	ng.hr.mL-1	Mus musculus
AUC	52.7	ng.hr.mL-1	Mus musculus
CL	316.67	mL.min-1.kg-1	Mus musculus
Cmax	200.81	nM	Mus musculus
F	9.9	%	Mus musculus
T1/2	0.9	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Hepatitis C virus	EC50	=	0.6	nM	9.22	Antiviral activity against HCV genotype 1b con1 infected in human Huh-luc/neo-ET...	29317151
NON-PROTEIN TARGET	IC50	=	0.7	nM	9.15	Antiproliferative activity against human HCT116 cells after 72 hrs by ATPlite as...	25499434
NON-PROTEIN TARGET	IC50	=	0.83	nM	9.08	Cytotoxicity against human SKHEP1 cells assessed as growth inhibition after 72 h...	26393416
CAKI-1	IC50	=	0.86	nM	9.07	Cytotoxicity against human Caki1 cells assessed as growth inhibition after 72 hr...	26393416
MDA-MB-231	IC50	=	0.89	nM	9.05	Cytotoxicity against human MDA-MB-231 cells assessed as growth inhibition after ...	26393416
A549	IC50	=	0.94	nM	9.03	Cytotoxicity against human A549 cells assessed as growth inhibition after 72 hrs...	26393416
HCT-116	IC50	=	1.04	nM	8.98	Cytotoxicity against human HCT116 cells assessed as growth inhibition after 72 h...	26393416
A-375	IC50	=	1.2	nM	8.92	Antiproliferative activity against human A375 cells after 72 hrs by ATPlite assa...	25499434
NON-PROTEIN TARGET	IC50	=	1.26	nM	8.9	Cytotoxicity against human SNU638 cells assessed as growth inhibition after 72 h...	26393416
A549	IC50	=	1.38	nM	8.86	Cytotoxicity against human A549 cells after 2 hrs by methylene blue staining-bas...	22823514
KB	IC50	=	1.51	nM	8.82	Cytotoxicity against human KB cells after 2 hrs by methylene blue staining-based...	22823514
DU-145	IC50	=	1.59	nM	8.8	Cytotoxicity against human DU145 cells after 2 hrs by methylene blue staining-ba...	22823514
NON-PROTEIN TARGET	IC50	=	1.8	nM	8.74	Cytotoxicity against human CL1-5 cells assessed as cell viability after 48 hrs b...	22823514
HCT-8	IC50	=	1.91	nM	8.72	Cytotoxicity against human HCT8 cells after 2 hrs by methylene blue staining-bas...	22823514
A549	IC50	=	1.9	nM	8.72	Cytotoxicity against human A549 cells assessed as cell viability after 48 hrs by...	22823514
A549	IC50	=	1.9	nM	8.72	Antiproliferative activity against human A549 cells after 72 hrs by ATPlite assa...	25499434
PA-1	IC50	=	2.0	nM	8.7	Cytotoxicity against human ovarian teratocarcinoma, PA1 cells	16236503
Daudi	IC50	=	2.0	nM	8.7	Cytotoxicity against human Burkitt lymphoma, DAUDI cells	16236503
Unchecked	IC50	=	2.0	nM	8.7	Cytotoxicity against human Huh-luc/neo-ET cells assessed as cell growth inhibiti...	29317151
PC-3	IC50	=	2.55	nM	8.59	Cytotoxicity against human PC3 cells assessed as growth inhibition after 72 hrs ...	26393416

Literature References

PubMed	DOI	Target Context	# Activities
29317151	10.1016/j.bmc.2017.12.027	Heat shock cognate 71 kDa protein	8
26393416	10.1021/acs.jmedchem.5b00764	Mus musculus	8
22823514	10.1021/jm3001218	A549	5
26393416	10.1021/acs.jmedchem.5b00764	CAKI-1	5
22823514	10.1021/jm3001218	NON-PROTEIN TARGET	3
16872154	10.1021/np060081y	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	2
29317151	10.1016/j.bmc.2017.12.027	Unchecked	2
25499434	10.1016/j.bmcl.2014.11.086	NON-PROTEIN TARGET	2
26393416	10.1021/acs.jmedchem.5b00764	No relevant target	2
26393416	10.1021/acs.jmedchem.5b00764	NON-PROTEIN TARGET	2
29317151	10.1016/j.bmc.2017.12.027	HepG2 2.2.15	2
16236503	10.1016/j.bmcl.2005.09.032	PA-1	1
16236503	10.1016/j.bmcl.2005.09.032	BUD-8	1
16236503	10.1016/j.bmcl.2005.09.032	HEK293	1
16236503	10.1016/j.bmcl.2005.09.032	HepG2	1
16236503	10.1016/j.bmcl.2005.09.032	HCT-15	1
16236503	10.1016/j.bmcl.2005.09.032	A549	1
16236503	10.1016/j.bmcl.2005.09.032	A-431	1
16236503	10.1016/j.bmcl.2005.09.032	KHOS/NP	1
16236503	10.1016/j.bmcl.2005.09.032	BT-20	1

Data from ChEMBL 36 via Core Engine