Compound Detail

CHEMBL227075

DIHYDROTANSHINONE I

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Cc1cccc2c3c(ccc12)C1=C(C(=O)C3=O)[C@@H](C)CO1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL227075
Name	DIHYDROTANSHINONE I
Phase	Preclinical
Structure Type	MOL
InChI Key	HARGZZNYNSYSGJ-JTQLQIEISA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

278.3

MW (Da)

3.29

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	C18H14O3
MW	278.31
Aromatic Rings	2
Heavy Atoms	21
NP-Likeness	1.70

Activity Summary

IC50 22 meas. best 7.17

Ki 7 meas. best 7.3

EC50 5 meas. best 5.6

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
ELAV-like protein 1 CHEMBL1250379	Ki	7.3	7.3	50.0	1
ELAV-like protein 1 CHEMBL1250379	IC50	7.17	7.0	68.0	2
Cocaine esterase CHEMBL3180	Ki	6.93	6.335	118.0	2
Liver carboxylesterase 1 CHEMBL2265	Ki	6.4	6.4	398.0	1
Replicase polyprotein 1ab CHEMBL4523582	IC50	6.23	6.23	590.0	1
Acetylcholinesterase CHEMBL220	Ki	6.22	5.965	600.0	2
Unchecked CHEMBL612545	IC50	6.17	6.17	680.0	1
Acetylcholinesterase CHEMBL220	IC50	6.0	6.0	1000.0	1
Aldo-keto reductase family 1 member B1 CHEMBL2622	IC50	5.92	5.92	1202.3	1
Replicase polyprotein 1a CHEMBL3927	IC50	5.92	5.26	1200.0	4
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha CHEMBL2221345	IC50	5.69	5.665	2050.0	2
HepG2 CHEMBL395	EC50	5.6	5.465	2500.0	2
PANC-1 CHEMBL614139	IC50	5.54	5.54	2910.0	1
Hep 3B2 CHEMBL4296437	IC50	5.5	5.5	3200.0	1
MCF7 CHEMBL387	IC50	5.43	5.43	3730.0	1
Tyrosine-protein phosphatase non-receptor type 6 CHEMBL3166	IC50	5.43	5.43	3670.0	1
Tyrosine-protein phosphatase non-receptor type 11 CHEMBL3864	IC50	5.41	5.41	3940.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	5.26	5.26	5500.0	1
ADMET CHEMBL612558	EC50	5.19	5.19	6500.0	1
SARS-CoV-2 CHEMBL4303835	EC50	5.09	5.09	8150.0	1
MDA-MB-231 CHEMBL400	IC50	5.05	5.05	8990.0	1
Replicase polyprotein 1a CHEMBL3927	Ki	4.95	4.95	11200.0	1
Lysine-specific histone demethylase 1A CHEMBL6136	IC50	4.8	4.8	15850.0	2
AGS CHEMBL613860	IC50	4.32	4.32	47700.0	1
Protease CHEMBL2366517	IC50	4.3	4.3	50600.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
ELAV-like protein 1	Ki	=	50.0	nM	7.3	Binding affinity to human full length recombinant His-tagged HuR expressed in Es...	29313684
ELAV-like protein 1	IC50	=	68.0	nM	7.17	Inhibition of ELAV1 (unknown origin)-ARE TNFalpha complex formation after 90 min...	28587461
Cocaine esterase	Ki	=	118.0	nM	6.93	Inhibition of human iCE using o-NPA as substrate by spectrophotometric assay	23286284
ELAV-like protein 1	IC50	=	149.0	nM	6.83	Inhibition of ELAV1 (unknown origin)-ARE TNFalpha complex formation after 3 hrs ...	28587461
Liver carboxylesterase 1	Ki	=	398.0	nM	6.4	Inhibition of human CE1 using o-NPA as substrate by spectrophotometric assay	23286284
Replicase polyprotein 1ab	IC50	=	590.0	nM	6.23	Inhibition of N-terminal 3xFlag-His6-tagged SARS-CoV-2 papain-like protease nsp3...	35620927
Acetylcholinesterase	Ki	=	600.0	nM	6.22	Inhibition of human acetylcholinesterase	24900610
Unchecked	IC50	=	680.0	nM	6.17	Competitive inhibition of FAM-labelled PscF (69 to 85 residues) binding to Pseud...	33479641
Acetylcholinesterase	IC50	=	1000.0	nM	6.0	Inhibition of acetylcholinesterase (unknown origin)	24900610
Aldo-keto reductase family 1 member B1	IC50	=	1202.26	nM	5.92	Inhibition of Rattus norvegicus (rat) lens aldose reductase	-
Replicase polyprotein 1a	IC50	=	1200.0	nM	5.92	Inhibition of SARS-CoV PLpro deubiququitination expressed in Escherichia coli BL...	22884354
Cocaine esterase	Ki	=	1830.0	nM	5.74	Inhibition of human iCE using CPT-11 as substrate by spectrophotometric assay	23286284
Acetylcholinesterase	Ki	=	1950.0	nM	5.71	Inhibition of human AChE using acetylthiocholine as substrate by spectrophotomet...	23286284
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	IC50	=	2050.0	nM	5.69	Inhibition of HIF1 activation in human AGS cells assessed as inhibition of hypox...	17583950
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	IC50	=	2290.0	nM	5.64	Inhibition of HIF1 activation in human Hep3B cells assessed as inhibition of hyp...	17583950
HepG2	EC50	=	2500.0	nM	5.6	Cytotoxicity against human HepG2 cells expressing wild type p53 gene by MTT assa...	20455578
PANC-1	IC50	=	2910.0	nM	5.54	Cytotoxicity against human PANC1 cells assessed as decrease in cell viability af...	29313684
Hep 3B2	IC50	=	3200.0	nM	5.5	Inhibition of hypoxia-induced HIF1alpha accumulation in Hep3B cells	17583950
Tyrosine-protein phosphatase non-receptor type 6	IC50	=	3670.0	nM	5.43	Inhibition of GST-tagged SHP1 PTP domain (unknown origin) using phospho-EGFR Asp...	23957426
MCF7	IC50	=	3730.0	nM	5.43	Cytotoxicity against human MCF7 cells assessed as decrease in cell viability aft...	29313684

Literature References

PubMed	DOI	Target Context	# Activities
26339922	10.1021/acs.jnatprod.5b00516	HepG2	12
22884354	10.1016/j.bmc.2012.07.038	Replicase polyprotein 1a	11
20455578	10.1021/np900792p	HepG2	7
23286284	10.1021/np300628a	Cocaine esterase	3
24900610	10.1021/ml400304w	Acetylcholinesterase	2
17583950	10.1021/np060482d	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	2
23286284	10.1021/np300628a	Acetylcholinesterase	2
29313684	10.1021/acs.jmedchem.7b01176	ELAV-like protein 1	2
26339922	10.1021/acs.jnatprod.5b00516	Mitogen-activated protein kinase; ERK1/ERK2	2
28587461	10.1021/acs.jmedchem.6b01871	ELAV-like protein 1	2
30852084	10.1016/j.bmcl.2019.02.028	GroEL/GroES	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
20455578	10.1021/np900792p	PLC-PRF-5	2
20455578	10.1021/np900792p	Hep 3B2	2
26339922	10.1021/acs.jnatprod.5b00516	MAP kinase p38	2
20455578	10.1021/np900792p	NON-PROTEIN TARGET	2
17583950	10.1021/np060482d	NON-PROTEIN TARGET	2
17583950	10.1021/np060482d	AGS	2
22884354	10.1016/j.bmc.2012.07.038	Unchecked	1
22884354	10.1016/j.bmc.2012.07.038	Papain	1

Data from ChEMBL 36 via Core Engine