Compound Detail

CHEMBL239077

TOMENTIC ACID

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C[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2[C@]1(C)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL239077
Name	TOMENTIC ACID
Phase	Preclinical
Structure Type	MOL
InChI Key	OXVUXGFZHDKYLS-BLIWDXROSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

488.7

MW (Da)

5.18

ALogP

HBA

HBD

98.0

PSA (Å²)

0.38

QED

Ro5 Violations

Rot. Bonds

Natural Product First in Class Prodrug

IC50 12 meas. best 5.62

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
SK-OV-3 CHEMBL614925	IC50	5.62	5.125	2400.0	2
Sentrin-specific protease 1 CHEMBL1909484	IC50	5.37	5.37	4300.0	1
Hepatocyte CHEMBL3140324	IC50	5.02	5.02	9500.0	1
8505C CHEMBL1075387	IC50	4.63	4.63	23400.0	1
RAW264.7 CHEMBL612557	IC50	4.6	4.6	24900.0	1
A549 CHEMBL392	IC50	4.51	4.51	31000.0	1
DLD-1 CHEMBL614285	IC50	4.51	4.51	31000.0	1
MCF7 CHEMBL387	IC50	4.49	4.49	32300.0	1
ADMET CHEMBL612558	IC50	4.32	4.32	47700.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.1	4.1	80250.0	1
K562 CHEMBL385	IC50	4.05	4.05	89360.0	1

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
SK-OV-3	IC50	=	2400.0	nM	5.62	Reversal of platinum resistance in cisplatin-resistant human SK-OV-3 cells asses...	35500202
Sentrin-specific protease 1	IC50	=	4300.0	nM	5.37	Inhibition of recombinant human SENP1 assessed as reduction in deSUMOylation usi...	35500202
Hepatocyte	IC50	=	9500.0	nM	5.02	Hepatoprotective activity against D-GaIN-induced toxicity in mouse hepatocyte re...	29353722
8505C	IC50	=	23400.0	nM	4.63	Cytotoxicity against human 8505C cells after 96 hrs by SRB assay	22995818
SK-OV-3	IC50	=	23240.0	nM	4.63	Cytotoxicity against human SK-OV-3 cells assessed as reduction in cell viability...	35500202
RAW264.7	IC50	=	24900.0	nM	4.6	Anti-inflammatory activity in mouse RAW264.7 cells assessed as inhibition of lip...	25245917
A549	IC50	=	31000.0	nM	4.51	Cytotoxicity against human A549 cells after 96 hrs by SRB assay	22995818
DLD-1	IC50	=	31000.0	nM	4.51	Cytotoxicity against human DLD1 cells after 96 hrs by SRB assay	22995818
MCF7	IC50	=	32300.0	nM	4.49	Cytotoxicity against human MCF7 cells after 96 hrs by SRB assay	22995818
ADMET	IC50	=	47700.0	nM	4.32	Cytotoxicity against human WW030272 cells after 96 hrs by SRB assay	22995818
NON-PROTEIN TARGET	IC50	=	80250.0	nM	4.1	Cytotoxicity against human multidrug resistant Lucena1 cells assessed as cell vi...	17889544
K562	IC50	=	89360.0	nM	4.05	Cytotoxicity against human K562 cells assessed as cell viability after 48 hrs by...	17889544

PubMed	DOI	Target Context	# Activities
35500202	10.1021/acs.jnatprod.1c01166	SK-OV-3	5
30108878	10.1039/C7MD00240H	MCF7	4
35500202	10.1021/acs.jnatprod.1c01166	Sentrin-specific protease 1	4
22995818	10.1016/j.ejmech.2012.08.032	8505C	4
30108878	10.1039/C7MD00240H	HepG2	3
30108878	10.1039/C7MD00240H	Bel-7402	3
30108878	10.1039/C7MD00240H	A549	3
25245917	10.1021/np500509q	RAW264.7	2
28358502	10.1021/acs.jnatprod.7b00111	C6	2
29353722	10.1016/j.ejmech.2018.01.011	Hepatocyte	2
22995818	10.1016/j.ejmech.2012.08.032	NON-PROTEIN TARGET	2
20873721	10.1021/np1003593	CCRF-CEM	1
22995818	10.1016/j.ejmech.2012.08.032	NIH3T3	1
22995818	10.1016/j.ejmech.2012.08.032	MCF7	1
20873721	10.1021/np1003593	ADMET	1
20873721	10.1021/np1003593	NCI-H460	1
20873721	10.1021/np1003593	MCF7	1
20100662	10.1016/j.bmc.2010.01.010	11-beta-hydroxysteroid dehydrogenase 1	1
9748372	10.1021/np9800710	H9	1
8759159	10.1021/np960165e	Protease	1

Data from ChEMBL 36 via Core Engine