Compound Detail

CHEMBL129451

(-)-CATECHINGALLATE

Enter ChEMBL ID:

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

O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@H]1c1ccc(O)c(O)c1)c1cc(O)c(O)c(O)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL129451
Name	(-)-CATECHINGALLATE
Phase	Preclinical
Structure Type	MOL
InChI Key	LSHVYAFMTMFKBA-CTNGQTDRSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

442.4

MW (Da)

2.53

ALogP

HBA

HBD

177.1

PSA (Å²)

0.24

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	C22H18O10
MW	442.38
Aromatic Rings	3
Heavy Atoms	32
NP-Likeness	1.84

Activity Summary

IC50 20 meas. best 6.91

Ki 4 meas. best 7.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Enoyl-acyl-carrier protein reductase CHEMBL4150	Ki	7.4	7.4	40.0	1
Proteasome Macropain subunit MB1 CHEMBL4662	IC50	6.91	6.91	124.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	IC50	6.66	6.66	220.0	1
Glucose-6-phosphate 1-dehydrogenase CHEMBL1075249	IC50	6.62	6.62	240.0	1
Enoyl-acyl-carrier protein reductase CHEMBL4150	IC50	6.52	6.52	300.0	2
Plasmodium falciparum CHEMBL364	IC50	6.4	5.8	400.0	3
Fatty acid synthase CHEMBL4512	IC50	6.4	6.4	400.0	1
Pyruvate kinase PKM CHEMBL1075189	IC50	6.07	6.07	850.0	1
3-oxoacyl-acyl-carrier protein reductase CHEMBL4513	IC50	6.0	6.0	1000.0	1
6-phosphogluconate dehydrogenase, decarboxylating CHEMBL3404	IC50	5.89	5.89	1280.0	1
NAD-dependent protein deacylase sirtuin-6 CHEMBL2163182	IC50	5.6	5.6	2500.0	2
Fatty acid synthase CHEMBL4512	Ki	5.55	5.55	2800.0	1
3-oxoacyl-acyl-carrier protein reductase CHEMBL4513	Ki	5.55	5.37	2800.0	2
Unchecked CHEMBL612545	IC50	5.47	4.9425	3400.0	4
Beta-secretase 1 CHEMBL4822	IC50	5.22	5.22	6000.0	1
Alpha-synuclein CHEMBL6152	IC50	4.67	4.67	21400.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Ke	210.0	nM	Homo sapiens
Ke	950.0	nM	Homo sapiens
Ke	220.0	nM	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Enoyl-acyl-carrier protein reductase	Ki	=	40.0	nM	7.4	Inhibition of FabI	16722653
Proteasome Macropain subunit MB1	IC50	=	124.0	nM	6.91	Inhibition of chymotrypsin-like activity of purified human 20S proteasome assess...	30776692
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	220.0	nM	6.66	Inhibition of DYRK1A (unknown origin) using HT-497 as substrate preincubated wit...	35292341
Glucose-6-phosphate 1-dehydrogenase	IC50	=	240.0	nM	6.62	Inhibition of yeast G6PD	18313308
Enoyl-acyl-carrier protein reductase	IC50	=	300.0	nM	6.52	Inhibition of FabI	16722653
Enoyl-acyl-carrier protein reductase	IC50	=	300.0	nM	6.52	Inhibition of Plasmodium falciparum FabI	20637612
Fatty acid synthase	IC50	=	400.0	nM	6.4	Inhibition of FabZ	16722653
Plasmodium falciparum	IC50	=	400.0	nM	6.4	Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum K1	16722653
Pyruvate kinase PKM	IC50	=	850.0	nM	6.07	Inhibition of recombinant PKM2 (unknown origin) Ser362, Ser205, Gly128, Lys207, ...	34726055
3-oxoacyl-acyl-carrier protein reductase	IC50	=	1000.0	nM	6.0	Inhibition of FabG	16722653
6-phosphogluconate dehydrogenase, decarboxylating	IC50	=	1280.0	nM	5.89	Inhibition of 6PGD	18313308
NAD-dependent protein deacylase sirtuin-6	IC50	=	2500.0	nM	5.6	Inhibition of GST-SIRT6 (unknown origin) assessed as deacetylation reaction usin...	34213345
NAD-dependent protein deacylase sirtuin-6	IC50	=	2500.0	nM	5.6	Inhibition of GST-tagged SIRT6 (unknown origin) deacetylase activity using H3K9A...	34213345
3-oxoacyl-acyl-carrier protein reductase	Ki	=	2800.0	nM	5.55	Inhibition of FabG in presence of NADPH	16722653
Fatty acid synthase	Ki	=	2800.0	nM	5.55	Inhibition of FabZ	16722653
Plasmodium falciparum	IC50	=	3200.0	nM	5.5	Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum NF54	16722653
Plasmodium falciparum	IC50	=	3200.0	nM	5.5	Antimalarial activity against chloroquine-sensitive Plasmodium falciparum NF54	20637612
Unchecked	IC50	=	3400.0	nM	5.47	Inhibition of duck liver FASN	21726077
Beta-secretase 1	IC50	=	6000.0	nM	5.22	Inhibition of human Beta-secretase 1	14592472
3-oxoacyl-acyl-carrier protein reductase	Ki	=	6400.0	nM	5.19	Inhibition of FabG in presence of acetoacetyl-CoA	16722653

Literature References

PubMed	DOI	Target Context	# Activities
34213345	10.1021/acs.jmedchem.1c00601	NAD-dependent protein deacylase sirtuin-6	3
16722653	10.1021/jm0600545	3-oxoacyl-acyl-carrier protein reductase	3
18313308	10.1016/j.bmc.2008.02.030	Unchecked	3
16722653	10.1021/jm0600545	Fatty acid synthase	2
21726077	10.1021/jm2005805	Unchecked	2
17685652	10.1021/np070194x	Unchecked	2
17685652	10.1021/np070194x	Kappa-type opioid receptor	2
17685652	10.1021/np070194x	Delta-type opioid receptor	2
17685652	10.1021/np070194x	Mu-type opioid receptor	2
16722653	10.1021/jm0600545	Plasmodium falciparum	2
16722653	10.1021/jm0600545	Enoyl-acyl-carrier protein reductase	2
18313308	10.1016/j.bmc.2008.02.030	Glucose-6-phosphate 1-dehydrogenase	1
18313308	10.1016/j.bmc.2008.02.030	6-phosphogluconate dehydrogenase, decarboxylating	1
17485508	10.1128/aac.00124-07	3-oxoacyl-acyl-carrier protein reductase	1
20637612	10.1016/j.bmcl.2010.06.120	Plasmodium falciparum	1
20637612	10.1016/j.bmcl.2010.06.120	Enoyl-acyl-carrier protein reductase	1
21826253	10.1021/ml100159p	Unchecked	1
-	10.1007/s00044-008-9151-y	NON-PROTEIN TARGET	1
28325635	10.1016/j.bmc.2017.03.023	Unchecked	1
30776692	10.1016/j.ejmech.2019.01.044	Proteasome Macropain subunit MB1	1

Data from ChEMBL 36 via Core Engine