Compound Detail

CHEMBL187460

CRYPTOTANSHINONE

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C[C@H]1COC2=C1C(=O)C(=O)c1c2ccc2c1CCCC2(C)C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL187460
Name	CRYPTOTANSHINONE
Phase	Preclinical
Structure Type	MOL
InChI Key	GVKKJJOMQCNPGB-JTQLQIEISA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

296.4

MW (Da)

3.44

ALogP

HBA

HBD

43.4

PSA (Å²)

0.69

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	C19H20O3
MW	296.37
Aromatic Rings	1
Heavy Atoms	22
NP-Likeness	2.44

Activity Summary

IC50 39 meas. best 6.1

EC50 6 meas. best 6.16

Ki 5 meas. best 6.85

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cocaine esterase CHEMBL3180	Ki	6.85	6.695	141.0	2
Liver carboxylesterase 1 CHEMBL2265	Ki	6.26	6.26	544.0	1
SARS-CoV-2 CHEMBL4303835	EC50	6.16	6.16	700.0	1
Replicase polyprotein 1a CHEMBL3927	IC50	6.1	5.0533	800.0	3
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha CHEMBL2221345	IC50	5.87	5.835	1360.0	2
Replicase polyprotein 1ab CHEMBL4523582	IC50	5.87	5.5	1336.0	3
Streptokinase A CHEMBL1293228	EC50	5.4	5.115	3953.0	2
Signal transducer and activator of transcription 3 CHEMBL4026	IC50	5.34	5.34	4600.0	1
Aldo-keto reductase family 1 member B1 CHEMBL2622	IC50	5.32	5.32	4786.3	1
ECa-109 cell line CHEMBL614668	IC50	5.3	5.3	5010.0	1
Streptococcus sp. 'group A' CHEMBL612389	EC50	5.29	5.29	5172.0	1
MIA PaCa-2 CHEMBL614725	IC50	5.24	5.24	5800.0	1
Acetylcholinesterase CHEMBL220	Ki	5.19	5.19	6410.0	1
Unchecked CHEMBL612545	IC50	5.18	5.18	6610.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.16	5.0133	6900.0	3
Replicase polyprotein 1a CHEMBL3927	Ki	5.05	5.05	9000.0	1
Lysine-specific histone demethylase 1A CHEMBL6136	IC50	5.04	5.04	9020.0	1
Tryptophan 2,3-dioxygenase CHEMBL2140	IC50	5.01	5.01	9800.0	1
Indoleamine 2,3-dioxygenase 1 CHEMBL4685	IC50	5.0	5.0	10000.0	1
AGS CHEMBL613860	IC50	4.99	4.93	10200.0	2
Plasmodium falciparum CHEMBL364	IC50	4.9	4.9	12500.0	1
Streptococcus CHEMBL612313	EC50	4.85	4.85	14089.0	1
Leishmania major CHEMBL612879	IC50	4.74	4.74	18400.0	1
Tyrosine-protein phosphatase non-receptor type 11 CHEMBL3864	IC50	4.65	4.565	22500.0	4
ADMET CHEMBL612558	EC50	4.64	4.64	22900.0	1
HepG2 CHEMBL395	IC50	4.54	4.54	29200.0	1
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	IC50	4.47	4.47	33500.0	1
PBMC CHEMBL613107	IC50	4.43	4.43	37400.0	1
Receptor-type tyrosine-protein phosphatase F CHEMBL3521	IC50	4.43	4.43	36900.0	1
Tyrosine-protein phosphatase non-receptor type 6 CHEMBL3166	IC50	4.4	4.4	39500.0	1
Receptor-type tyrosine-protein phosphatase C CHEMBL3243	IC50	4.38	4.38	41400.0	1
Tyrosine-protein phosphatase non-receptor type 2 CHEMBL3807	IC50	4.25	4.25	55700.0	1
Tyrosine-protein phosphatase non-receptor type 9 CHEMBL6117	IC50	4.23	4.23	59400.0	1
Protease CHEMBL2366517	IC50	4.16	4.16	69600.0	1
Papain CHEMBL4779	IC50	4.05	4.05	89800.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
F	10.6	%	Rattus norvegicus
F	2.1	%	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cocaine esterase	Ki	=	141.0	nM	6.85	Inhibition of human iCE using o-NPA as substrate by spectrophotometric assay	23286284
Cocaine esterase	Ki	=	290.0	nM	6.54	Inhibition of human iCE using CPT-11 as substrate by spectrophotometric assay	23286284
Liver carboxylesterase 1	Ki	=	544.0	nM	6.26	Inhibition of human CE1 using o-NPA as substrate by spectrophotometric assay	23286284
SARS-CoV-2	EC50	=	700.0	nM	6.16	Antiviral activity against SARS-CoV-2 nCoV-2019BetaCoV/Wuhan/WIV04/2019 infected...	35620927
Replicase polyprotein 1a	IC50	=	800.0	nM	6.1	Inhibition of SARS-CoV PLpro expressed in Escherichia coli BL21 (DE3) using Arg-...	22884354
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	IC50	=	1360.0	nM	5.87	Inhibition of HIF1 activation in human Hep3B cells assessed as inhibition of hyp...	17583950
Replicase polyprotein 1ab	IC50	=	1336.0	nM	5.87	Inhibition of N-terminal 3xFlag-His6-tagged SARS-CoV-2 papain-like protease nsp3...	35620927
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	IC50	=	1580.0	nM	5.8	Inhibition of HIF1 activation in human AGS cells assessed as inhibition of hypox...	17583950
Streptokinase A	EC50	=	3953.0	nM	5.4	PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden...	-
Replicase polyprotein 1ab	IC50	=	4200.0	nM	5.38	Inhibition of SARS-CoV-2 3CL protease	33352046
Signal transducer and activator of transcription 3	IC50	=	4600.0	nM	5.34	Inhibition of STAT3 expressed in human HCT116 cells after 24 hrs by luciferase r...	22650325
Aldo-keto reductase family 1 member B1	IC50	=	4786.3	nM	5.32	Inhibition of Rattus norvegicus (rat) lens aldose reductase	-
ECa-109 cell line	IC50	=	5010.0	nM	5.3	Antitumor activity against human EC109 cells assessed as reduction in cell viabi...	35504209
Streptococcus sp. 'group A'	EC50	=	5172.0	nM	5.29	PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden...	-
Replicase polyprotein 1ab	IC50	=	5630.0	nM	5.25	Inhibition of full-length SARS-CoV-2 papain-like protease (1564 to 1878 residues...	35620927
MIA PaCa-2	IC50	=	5800.0	nM	5.24	Cytotoxicity against human MIAPaCa2 cells after 24 hrs by MTT assay	21775156
Acetylcholinesterase	Ki	=	6410.0	nM	5.19	Inhibition of human AChE using acetylthiocholine as substrate by spectrophotomet...	23286284
Unchecked	IC50	=	6610.0	nM	5.18	Inhibition of IL-6/JAK/STAT3 signalling pathway in HEK-blue IL-6 cells incubated...	35504209
NON-PROTEIN TARGET	IC50	=	6900.0	nM	5.16	Cytotoxicity against drug-sensitive human KB-3-1 cells after 48 hrs by MTS/PMS a...	11720520
NON-PROTEIN TARGET	IC50	=	7500.0	nM	5.12	Cytotoxicity against multidrug-resistant human KBV1 cells after 48 hrs by MTS/PM...	11720520

Literature References

PubMed	DOI	Target Context	# Activities
23957426	10.1021/jm400474r	Tyrosine-protein phosphatase non-receptor type 11	15
23957426	10.1021/jm400474r	Unchecked	13
22884354	10.1016/j.bmc.2012.07.038	Replicase polyprotein 1a	9
37040078	10.1021/acs.jnatprod.2c01004	J774.A1	6
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
20455578	10.1021/np900792p	HepG2	4
18855446	10.1021/np800119k	Artery	3
23286284	10.1021/np300628a	Cocaine esterase	3
23957426	10.1021/jm400474r	NON-PROTEIN TARGET	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	2
17583950	10.1021/np060482d	NON-PROTEIN TARGET	2
17583950	10.1021/np060482d	AGS	2
11720520	10.1021/np010032f	NON-PROTEIN TARGET	2
20455578	10.1021/np900792p	Hep 3B2	2
23286284	10.1021/np300628a	Acetylcholinesterase	2
23957426	10.1021/jm400474r	HeLa	2
23957426	10.1021/jm400474r	MEF	2
-	10.1039/C4MD00177J	Signal transducer and activator of transcription 3	2
17583950	10.1021/np060482d	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	2

Data from ChEMBL 36 via Core Engine