Compound Detail

CHEMBL187266

TANSHINONE IIA

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

Cc1coc2c1C(=O)C(=O)c1c-2ccc2c1CCCC2(C)C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL187266
Name	TANSHINONE IIA
Phase	Preclinical
Structure Type	MOL
InChI Key	HYXITZLLTYIPOF-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

294.4

MW (Da)

4.25

ALogP

HBA

HBD

47.3

PSA (Å²)

0.68

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	C19H18O3
MW	294.35
Aromatic Rings	2
Heavy Atoms	22
NP-Likeness	1.95

Activity Summary

IC50 54 meas. best 6.4

Ki 5 meas. best 7.16

EC50 3 meas. best 6.05

Kd 1 meas. best 9.06

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
DNA repair nuclease/redox regulator APEX1 CHEMBL5619	Kd	9.06	9.06	0.9	1
Cocaine esterase CHEMBL3180	Ki	7.16	6.385	69.4	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.4	6.4	400.0	1
LNCaP CHEMBL612518	IC50	6.3	6.3	500.0	1
Telomerase reverse transcriptase CHEMBL2916	IC50	6.3	5.8	500.0	2
MCF7 CHEMBL387	EC50	6.05	6.05	900.0	1
Aldo-keto reductase family 1 member B1 CHEMBL2622	IC50	5.94	5.94	1140.0	3
PC-3 CHEMBL390	EC50	5.92	5.92	1200.0	1
Replicase polyprotein 1ab CHEMBL4523582	IC50	5.8	5.8	1571.0	1
Replicase polyprotein 1a CHEMBL3927	IC50	5.8	4.8733	1600.0	3
MIA PaCa-2 CHEMBL614725	IC50	5.72	5.72	1900.0	1
Tyrosine-protein phosphatase non-receptor type 6 CHEMBL3166	IC50	5.67	5.67	2140.0	1
A549 CHEMBL392	IC50	5.66	5.0333	2200.0	3
Toxoplasma gondii CHEMBL612888	IC50	5.6	5.6	2500.0	1
Tyrosine-protein phosphatase non-receptor type 11 CHEMBL3864	IC50	5.59	5.59	2590.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	Ki	5.59	5.59	2560.0	1
BGC-823 CHEMBL614526	IC50	5.55	5.55	2800.0	1
NCI-N87 CHEMBL614197	IC50	5.51	5.51	3100.0	1
PC-3 CHEMBL390	IC50	5.5	5.49	3200.0	2
Unchecked CHEMBL612545	IC50	5.49	4.87	3228.0	3
HeLa CHEMBL399	IC50	5.46	5.46	3470.0	1
K562 CHEMBL385	IC50	5.34	5.34	4600.0	1
Apoptotic protease-activating factor 1 CHEMBL1795093	IC50	5.32	5.32	4820.0	1
HepG2 CHEMBL395	IC50	5.31	4.6825	4910.0	4
NACHT, LRR and PYD domains-containing protein 3 CHEMBL3779755	IC50	5.29	5.29	5150.0	1
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha CHEMBL2221345	IC50	5.21	5.165	6180.0	2
AGS CHEMBL613860	IC50	5.17	5.085	6800.0	2
CWR22R CHEMBL612657	IC50	5.17	5.17	6700.0	1
Liver carboxylesterase 1 CHEMBL2265	Ki	5.16	5.16	6890.0	1
MDA-MB-231 CHEMBL400	IC50	5.11	5.11	7695.0	1
MCF7 CHEMBL387	IC50	5.11	5.11	7793.5	1
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	5.06	5.06	8690.0	1
Replicase polyprotein 1a CHEMBL3927	Ki	4.95	4.95	11200.0	1
Alpha-glucosidase CHEMBL5291954	IC50	4.94	4.94	11390.0	1
RAW264.7 CHEMBL612557	IC50	4.74	4.74	18170.0	1
ADMET CHEMBL612558	EC50	4.64	4.64	22900.0	1
EZH2/SUZ12/EED complex CHEMBL3137286	IC50	4.55	4.55	28100.0	1
Monoglyceride lipase CHEMBL4191	IC50	4.32	4.32	48000.0	1
Protease CHEMBL2366517	IC50	4.23	4.23	59200.0	1
L02 CHEMBL4296457	IC50	4.18	4.145	65290.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	45.0	mL.min-1.g-1	Homo sapiens
F	3.5	%	Rattus norvegicus
T1/2	0.1667	hr	Homo sapiens
T1/2	0.34	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
DNA repair nuclease/redox regulator APEX1	Kd	=	0.88	nM	9.06	Binding affinity to full length human APE1 expressed in Escherichia coli BL21/DE...	28161249
Cocaine esterase	Ki	=	69.4	nM	7.16	Inhibition of human iCE using CPT-11 as substrate by spectrophotometric assay	23286284
NON-PROTEIN TARGET	IC50	=	400.0	nM	6.4	Cytotoxicity against human C4-2B cells incubated for 72 hrs by MTT assay	22175694
Telomerase reverse transcriptase	IC50	=	500.0	nM	6.3	Inhibition of pre-assembled human recombinant telomerase activity in rabbit reti...	22044621
LNCaP	IC50	=	500.0	nM	6.3	Cytotoxicity against human LNCAP cells incubated for 72 hrs by MTT assay	22175694
MCF7	EC50	=	900.0	nM	6.05	Cytotoxicity against telomerase positive human MCF7 cells after 96 hrs by SRB as...	22044621
Aldo-keto reductase family 1 member B1	IC50	=	1140.0	nM	5.94	Inhibition of rat aldose reductase	22261024
Aldo-keto reductase family 1 member B1	IC50	=	1140.0	nM	5.94	Inhibition of rat lens aldose reductase	22261024
Aldo-keto reductase family 1 member B1	IC50	=	1148.15	nM	5.94	Inhibition of Rattus norvegicus (rat) lens aldose reductase	-
PC-3	EC50	=	1200.0	nM	5.92	Cytotoxicity against telomerase positive human PC3 cells after 96 hrs by SRB ass...	22044621
Replicase polyprotein 1a	IC50	=	1600.0	nM	5.8	Inhibition of SARS-CoV PLpro expressed in Escherichia coli BL21 (DE3) using Arg-...	22884354
Replicase polyprotein 1ab	IC50	=	1571.0	nM	5.8	Inhibition of N-terminal 3xFlag-His6-tagged SARS-CoV-2 papain-like protease nsp3...	35620927
MIA PaCa-2	IC50	=	1900.0	nM	5.72	Cytotoxicity against human MIAPaCa2 cells after 24 hrs by MTT assay	21775156
Tyrosine-protein phosphatase non-receptor type 6	IC50	=	2140.0	nM	5.67	Inhibition of GST-tagged SHP1 PTP domain (unknown origin) using phospho-EGFR Asp...	23957426
A549	IC50	=	2200.0	nM	5.66	Antiproliferative activity against human A549 cells assessed as reduction in cel...	34333396
Cocaine esterase	Ki	=	2450.0	nM	5.61	Inhibition of human iCE using o-NPA as substrate by spectrophotometric assay	23286284
Toxoplasma gondii	IC50	=	2500.0	nM	5.6	Antiparasitic activity against Toxoplasma gondii	31585276
Peroxisome proliferator-activated receptor gamma	Ki	=	2560.0	nM	5.59	Binding affinity to PPARgamma (unknown origin)	33992930
Tyrosine-protein phosphatase non-receptor type 11	IC50	=	2590.0	nM	5.59	Inhibition of GST-tagged SHP2 PTP domain (unknown origin) using phospho-EGFR Asp...	23957426
BGC-823	IC50	=	2800.0	nM	5.55	Anticancer activity against human BGC-823 cells assessed as inhibition of cell v...	36332549

Literature References

PubMed	DOI	Target Context	# Activities
22175694	10.1021/jm2015292	Androgen receptor	16
22884354	10.1016/j.bmc.2012.07.038	Replicase polyprotein 1a	11
22261024	10.1016/j.bmc.2011.12.033	Aldo-keto reductase family 1 member B1	10
33751939	10.1016/j.bmc.2021.116112	MCF7	6
22044621	10.1016/j.bmcl.2011.09.112	Telomerase reverse transcriptase	6
-	10.1039/C4MD00186A	Monoglyceride lipase	6
33751939	10.1016/j.bmc.2021.116112	MDA-MB-231	5
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
22175694	10.1021/jm2015292	PC-3	4
20455578	10.1021/np900792p	HepG2	4
22175694	10.1021/jm2015292	LNCaP	4
18024584	10.1073/pnas.0709695104	H4	4
36786612	10.1021/acs.jmedchem.2c01967	Peritoneal macrophage	4
18855446	10.1021/np800119k	Artery	3
23286284	10.1021/np300628a	Cocaine esterase	3
22175694	10.1021/jm2015292	Unchecked	3
22044621	10.1016/j.bmcl.2011.09.112	No relevant target	3
38599295	10.1016/j.bmcl.2024.129736	Alpha-glucosidase	2
20455578	10.1021/np900792p	Hep 3B2	2
17583950	10.1021/np060482d	NON-PROTEIN TARGET	2

Data from ChEMBL 36 via Core Engine