Compound Detail

CHEMBL260553

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CC(C)=CCc1c(O)cc2oc3cc(O)c(O)c(CC=C(C)C)c3c(=O)c2c1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL260553
Phase	Preclinical
Structure Type	MOL
InChI Key	VEZXFTKZUMARDU-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

396.4

MW (Da)

4.79

ALogP

HBA

HBD

111.1

PSA (Å²)

0.29

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	C23H24O6
MW	396.44
Aromatic Rings	3
Heavy Atoms	29
NP-Likeness	1.84

Activity Summary

IC50 22 meas. best 6.1

Ki 5 meas. best 6.1

EC50 1 meas. best 5.66

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Prostaglandin G/H synthase 1 CHEMBL221	IC50	6.1	6.1	800.0	1
Sialidase CHEMBL5189	Ki	6.1	5.615	800.0	2
Fatty acid synthase CHEMBL4158	IC50	5.91	5.91	1240.0	1
Alpha glucosidase CHEMBL3833502	Ki	5.85	5.85	1400.0	1
Alpha glucosidase CHEMBL3833502	IC50	5.77	5.77	1700.0	1
Phosphoglycerate mutase 1 CHEMBL3334418	IC50	5.72	5.72	1900.0	1
Prostaglandin G/H synthase 2 CHEMBL230	IC50	5.7	5.7	2000.0	1
Oxidized purine nucleoside triphosphate hydrolase CHEMBL3708265	IC50	5.7	5.7	2000.0	1
NCI-H1299 CHEMBL612255	EC50	5.66	5.66	2200.0	1
Sialidase CHEMBL5189	IC50	5.66	5.66	2200.0	1
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	Ki	5.57	5.57	2700.0	1
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	IC50	5.55	5.55	2800.0	1
Isocitrate dehydrogenase [NADP] cytoplasmic CHEMBL2007625	Ki	5.5	5.5	3170.0	1
NAD-dependent protein deacetylase sirtuin-2 CHEMBL4462	IC50	5.42	5.42	3800.0	2
NCI-H460 CHEMBL396	IC50	5.35	5.35	4480.0	1
Aromatase CHEMBL1978	IC50	5.3	5.23	4970.0	2
SW-620 CHEMBL612262	IC50	5.25	5.25	5690.0	1
MDA-MB-231 CHEMBL400	IC50	5.23	5.205	5870.0	2
ASPC1 CHEMBL612588	IC50	5.23	5.23	5920.0	1
HL-60 CHEMBL383	IC50	5.21	5.21	6100.0	1
Transthyretin CHEMBL3194	IC50	5.0	5.0	10000.0	1
NAD-dependent protein deacetylase sirtuin-1 CHEMBL4506	IC50	4.65	4.65	22400.0	1
SK-BR-3 CHEMBL613834	IC50	4.58	4.58	25990.0	1
NAD-dependent protein deacetylase sirtuin-3, mitochondrial CHEMBL4461	IC50	4.57	4.57	26800.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Prostaglandin G/H synthase 1	IC50	=	800.0	nM	6.1	Inhibition of COX1	16038536
Sialidase	Ki	=	800.0	nM	6.1	Competitive inhibition of Clostridium perfringens neuraminidase by fluorimetry	20696581
Fatty acid synthase	IC50	=	1240.0	nM	5.91	Inhibition of FAS	20817450
Alpha glucosidase	Ki	=	1400.0	nM	5.85	Inhibition of alpha-glucosidase (unknown origin) using PNP-G as substrate by Dix...	29306546
Alpha glucosidase	IC50	=	1700.0	nM	5.77	Inhibition of alpha-glucosidase (unknown origin) using PNP-G as substrate measur...	29306546
Phosphoglycerate mutase 1	IC50	=	1900.0	nM	5.72	Inhibition of PGAM1 (unknown origin)	33513389
Prostaglandin G/H synthase 2	IC50	=	2000.0	nM	5.7	Inhibition of COX2	16038536
Oxidized purine nucleoside triphosphate hydrolase	IC50	=	2000.0	nM	5.7	Inhibition of recombinant C-terminal 6xHis-tagged MTH1 (3 to 156 residues) (unkn...	30771603
Sialidase	IC50	=	2200.0	nM	5.66	Inhibition of Clostridium perfringens neuraminidase by fluorimetry	20696581
NCI-H1299	EC50	=	2200.0	nM	5.66	Antiproliferative activity against human NCI-H1299 cells assessed as inhibition ...	33513389
Tyrosine-protein phosphatase non-receptor type 1	Ki	=	2700.0	nM	5.57	Inhibition of recombinant human PTP1B (1 to 322 residues) expressed in Escherich...	29306546
Tyrosine-protein phosphatase non-receptor type 1	IC50	=	2800.0	nM	5.55	Inhibition of recombinant human PTP1B (1 to 322 residues) expressed in Escherich...	29306546
Isocitrate dehydrogenase [NADP] cytoplasmic	Ki	=	3170.0	nM	5.5	Competitive inhibition of IDH1-R132H mutant (unknown origin) using a-ketoglutara...	26508549
NAD-dependent protein deacetylase sirtuin-2	IC50	=	3800.0	nM	5.42	Inhibition of AMC-conjugated recombinant human SIRT2 ( 317 to 320 residues) usin...	38280655
NAD-dependent protein deacetylase sirtuin-2	IC50	=	3800.0	nM	5.42	Inhibition of human SIRT2 using sirtuin substrate incubated for 30 mins by enzym...	34303869
NCI-H460	IC50	=	4480.0	nM	5.35	Cytotoxicity against human NCI-H460 cells assessed as inhibition of cell prolife...	24717154
Aromatase	IC50	=	4970.0	nM	5.3	Inhibition of aromatase over-expressed in human SKBR3 cells	18558747
SW-620	IC50	=	5690.0	nM	5.25	Cytotoxicity against human SW620 cells assessed as inhibition of cell proliferat...	24717154
MDA-MB-231	IC50	=	5870.0	nM	5.23	Cytotoxicity against human MDA-MB-231 cells assessed as inhibition of cell proli...	24717154
ASPC1	IC50	=	5920.0	nM	5.23	Cytotoxicity against human AsPC1 cells assessed as inhibition of cell proliferat...	24717154

Literature References

PubMed	DOI	Target Context	# Activities
18328716	10.1016/j.bmc.2008.02.054	Tyrosine-protein kinase SYK	7
29684706	10.1016/j.ejmech.2018.04.022	Erythrocyte	5
18558747	10.1021/np8000255	Aromatase	5
20696581	10.1016/j.bmc.2010.07.033	Sialidase	4
9213587	10.1021/np970165u	Alternaria alternata	4
9213587	10.1021/np970165u	Drechslera	4
9213587	10.1021/np970165u	Fusarium oxysporum f. sp. vasinfectum	4
18328716	10.1016/j.bmc.2008.02.054	RBL-2H3	4
22578462	10.1016/j.bmcl.2012.04.081	Unchecked	3
29306546	10.1016/j.bmc.2017.12.043	Tyrosine-protein phosphatase non-receptor type 1	3
29306546	10.1016/j.bmc.2017.12.043	Alpha glucosidase	3
32795625	10.1016/j.bmcl.2020.127494	Enterococcus faecalis	2
18558747	10.1021/np8000255	SK-BR-3	2
30771603	10.1016/j.ejmech.2019.02.011	Oxidized purine nucleoside triphosphate hydrolase	2
21428375	10.1021/np200051j	HT-29	2
12932141	10.1021/np020546u	HL-60	1
38280655	10.1016/j.bmcl.2024.129620	NAD-dependent protein deacetylase sirtuin-3, mitochondrial	1
20817450	10.1016/j.bmcl.2010.08.061	Fatty acid synthase	1
16038536	10.1021/np049655u	Prostaglandin G/H synthase 1	1
18328716	10.1016/j.bmc.2008.02.054	Unchecked	1

Data from ChEMBL 36 via Core Engine