Compound Detail

CHEMBL382408

PENTAGALLOYL GLUCOSE

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O=C(OC[C@H]1O[C@@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@@H]1OC(=O)c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL382408
Name	PENTAGALLOYL GLUCOSE
Phase	Preclinical
Structure Type	MOL
InChI Key	QJYNZEYHSMRWBK-NIKIMHBISA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

940.7

MW (Da)

1.69

ALogP

HBA

HBD

444.2

PSA (Å²)

0.05

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	C41H32O26
MW	940.68
Aromatic Rings	5
Heavy Atoms	67
NP-Likeness	0.62

Activity Summary

IC50 27 meas. best 7.7

Ki 4 meas. best 6.24

EC50 2 meas. best 4.82

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Mushroom tyrosinase CHEMBL6066154	IC50	7.7	7.7	20.0	2
Prothrombin CHEMBL4471	IC50	7.3	7.13	50.0	2
Coagulation factor X CHEMBL244	IC50	6.77	6.77	170.0	1
Anthrax toxin receptor 2 CHEMBL4296326	IC50	6.52	6.37	300.0	2
Unchecked CHEMBL612545	IC50	6.41	6.41	390.0	1
Squalene monooxygenase CHEMBL4241	IC50	6.33	6.33	470.0	1
Coagulation factor X CHEMBL244	Ki	6.24	6.24	570.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.09	6.09	820.0	1
Genome polyprotein CHEMBL2396505	IC50	5.96	5.96	1100.0	1
Ectonucleoside triphosphate diphosphohydrolase 1 CHEMBL4739681	IC50	5.81	5.81	1560.0	1
NS3 CHEMBL1293269	IC50	5.8	5.8	1600.0	1
HCT-116 CHEMBL394	IC50	5.79	5.79	1610.0	1
Alpha-amylase 1A CHEMBL2478	IC50	5.63	5.63	2350.0	1
Alpha-amylase 1A CHEMBL2478	Ki	5.58	5.58	2600.0	1
Xanthine dehydrogenase/oxidase CHEMBL3649	IC50	5.5	5.5	3200.0	1
Beta-secretase 1 CHEMBL4822	IC50	5.42	5.42	3760.0	1
Prothrombin CHEMBL4471	Ki	5.41	5.41	3900.0	1
Protein kinase C (PKC) CHEMBL2093867	IC50	5.4	5.4	4000.0	1
HT-29 CHEMBL384	IC50	5.35	5.35	4460.0	1
Beta-secretase 1 CHEMBL4822	Ki	5.29	5.29	5130.0	1
MDA-MB-231 CHEMBL400	IC50	5.04	5.04	9120.0	1
5'-nucleotidase CHEMBL5957	IC50	4.98	4.98	10540.0	1
Neuraminidase CHEMBL3232678	IC50	4.92	4.92	11900.0	1
Human immunodeficiency virus 1 CHEMBL378	EC50	4.82	4.785	15000.0	2
Human immunodeficiency virus 1 CHEMBL378	IC50	4.72	4.535	19000.0	2
MIA PaCa-2 CHEMBL614725	IC50	4.14	4.14	72590.0	1
HepG2 CHEMBL395	IC50	4.03	4.03	92400.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Cmax	1000.0	nM	Mus musculus
Ka	33.7	/M	-
Ka	20.0	/M	-
Ka	20.4	/M	-
Ka	13.0	/M	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Mushroom tyrosinase	IC50	=	20.0	nM	7.7	Inhibition of mushroom tyrosinase monophenolase activity	39026645
Mushroom tyrosinase	IC50	=	20.0	nM	7.7	Inhibition of mushroom tyrosinase diphenolase activity	39026645
Prothrombin	IC50	=	50.0	nM	7.3	Inhibition of bovine thrombin-catalyzed hydrolysis of fibrinogen	9834152
Prothrombin	IC50	=	110.0	nM	6.96	Inhibition of bovine thrombin-catalyzed hydrolysis of S-2238	9834152
Coagulation factor X	IC50	=	170.0	nM	6.77	Inhibition of human factor 10a-catalyzed hydrolysis of S-2222	9834152
Anthrax toxin receptor 2	IC50	=	300.0	nM	6.52	Inhibition of CMG2 (40 to 217) C175A and R40C double mutant (unknown origin) int...	23394144
Unchecked	IC50	=	390.0	nM	6.41	Inhibition of alpha-glucosidase (unknown origin) using PNPG as substrate assesse...	-
Squalene monooxygenase	IC50	=	470.0	nM	6.33	Inhibition of C-terminal hexahistidine-tagged rat recombinant squalene epoxidase...	11520216
Coagulation factor X	Ki	=	570.0	nM	6.24	Inhibition of human factor 10a	9834152
Anthrax toxin receptor 2	IC50	=	607.0	nM	6.22	Inhibition of AF488-labelled PA binding to AF546- labelled GST-tagged CMG2 R40C/...	30964669
NON-PROTEIN TARGET	IC50	=	820.0	nM	6.09	Antiangiogenic activity in HMVEC assessed as inhibition of endothelial cell migr...	23394144
Genome polyprotein	IC50	=	1100.0	nM	5.96	Inhibition of His-6-tagged Coxsackievirus B3 3C protease expressed in Escherichi...	24613627
Ectonucleoside triphosphate diphosphohydrolase 1	IC50	=	1560.0	nM	5.81	Inhibition of mouse CD39	33359608
NS3	IC50	=	1600.0	nM	5.8	Inhibitory activity against Hepatitis C virus NS3 protease by ELISA	15546725
HCT-116	IC50	=	1610.0	nM	5.79	Cytotoxicity against human HCT116 cells assessed as reduction in cell viability ...	29778287
Alpha-amylase 1A	IC50	=	2350.0	nM	5.63	Inhibition of human salivary alpha-amylase using GalG2CNP as substrate assessed ...	26395057
Alpha-amylase 1A	Ki	=	2600.0	nM	5.58	Non-competitive inhibition of human salivary alpha-amylase using GalG2CNP as sub...	26395057
Xanthine dehydrogenase/oxidase	IC50	=	3200.0	nM	5.5	Inhibition of cow milk xanthine oxidase	2723668
Beta-secretase 1	IC50	=	3760.0	nM	5.42	Inhibition of BACE1 (unknown origin)	24835197
Prothrombin	Ki	=	3900.0	nM	5.41	Inhibition of bovine thrombin by Lineweaver-Burke plot analysis	9834152

Literature References

PubMed	DOI	Target Context	# Activities
29778287	10.1016/j.bmcl.2018.05.028	HCT-116	65
29778287	10.1016/j.bmcl.2018.05.028	HT-29	49
2413172	10.1021/np50040a016	Unchecked	10
22216935	10.1021/np200426k	HT-29	9
9834152	10.1021/np9801458	Plasma	8
20144544	10.1016/j.bmcl.2010.01.084	Hepatitis C virus	6
-	10.1016/S0960-894X(00)80422-9	Human immunodeficiency virus 1	6
23394144	10.1021/jm301558t	Mus musculus	5
34329818	10.1016/j.bmc.2021.116329	SARS-CoV-2	5
8991956	10.1021/np960040+	Unchecked	4
9834152	10.1021/np9801458	Prothrombin	3
29019685	10.1021/acs.jnatprod.7b00496	Staphylococcus aureus	3
24835197	10.1016/j.bmcl.2014.04.060	Beta-secretase 1	2
9834152	10.1021/np9801458	Coagulation factor X	2
39026645	10.1039/d4md00224e	Mushroom tyrosinase	2
24613627	10.1016/j.bmc.2014.02.014	Genome polyprotein	2
28368593	10.1021/acs.jnatprod.6b00915	Lactoperoxidase	2
24613627	10.1016/j.bmc.2014.02.014	Neuraminidase	2
26395057	10.1016/j.bmc.2015.09.007	Alpha-amylase 1A	2
-	10.1016/S0960-894X(00)80422-9	Human immunodeficiency virus type 1 reverse transcriptase	2

Data from ChEMBL 36 via Core Engine