Compound Detail

CHEMBL583912

(-)-EPICATECHIN

🧪 Phase II

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🧪 Phase II

Oc1cc(O)c2c(c1)O[C@H](c1ccc(O)c(O)c1)[C@H](O)C2

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL583912
Name	(-)-EPICATECHIN
Phase	Phase II
Structure Type	MOL
InChI Key	PFTAWBLQPZVEMU-UKRRQHHQSA-N

Known Names

(-)-epi catechin (-)-epicatechin (-)-epicatechol Epi-catechin Epi-catechol Epicatechin Epicatechol L-acacatechin L-epicatechin NSC-81161

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

290.3

MW (Da)

1.55

ALogP

HBA

HBD

110.4

PSA (Å²)

0.51

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula	C15H14O6
MW	290.27
Aromatic Rings	2
Heavy Atoms	21
NP-Likeness	2.30

Indications

Muscular Dystrophy, Duchenne Hypertension, Pulmonary

Activity Summary

IC50 37 meas. best 6.39

EC50 6 meas. best 8.7

Kd 3 meas. best 4.59

Ki 1 meas. best 6.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Nitric oxide synthase 3 CHEMBL4802	EC50	8.7	8.7	2.0	1
Arginase CHEMBL3108635	Ki	6.7	6.7	200.0	1
Alkaline phosphatase, tissue-nonspecific isozyme CHEMBL5979	IC50	6.39	6.39	407.0	1
Alpha-synuclein CHEMBL6152	IC50	6.1	5.31	800.0	2
Pyruvate kinase PKM CHEMBL1075189	IC50	5.88	5.88	1330.0	1
Intestinal-type alkaline phosphatase CHEMBL3151	IC50	5.87	5.87	1360.0	1
Aspartyl aminopeptidase CHEMBL1293263	IC50	5.86	5.86	1376.0	1
DNA repair protein RAD52 homolog CHEMBL2362978	IC50	5.84	5.84	1450.0	1
Arginase CHEMBL3108635	IC50	5.8	5.8	1600.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.8	4.9533	1590.0	3
Prostaglandin G/H synthase 1 CHEMBL2949	IC50	5.7	5.305	2000.0	2
Unchecked CHEMBL612545	IC50	5.55	5.2	2800.0	3
No relevant target CHEMBL2362975	EC50	5.39	5.39	4100.0	1
Beta-secretase 1 CHEMBL4822	IC50	5.35	5.35	4500.0	1
Amyloid-beta precursor protein CHEMBL2487	IC50	5.28	5.28	5300.0	1
LNCaP CHEMBL612518	EC50	4.89	4.89	13000.0	1
No relevant target CHEMBL2362975	IC50	4.87	4.845	13600.0	2
DNA polymerase beta CHEMBL4343	IC50	4.73	4.73	18500.0	1
Prostaglandin G/H synthase 1 CHEMBL2949	Kd	4.59	4.59	25900.0	1
Radical scavenging activity CHEMBL613712	IC50	4.31	4.31	49000.0	1
Alkaline phosphatase, germ cell type CHEMBL3402	EC50	4.29	4.29	51300.0	1
Unchecked CHEMBL612545	Kd	4.27	4.27	54000.0	1
Alpha amylase CHEMBL6066863	IC50	2.46	2.46	3500000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Ka	1.92	10'2/M	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Nitric oxide synthase 3	EC50	=	2.0	nM	8.7	Activation of eNOS in BCAEC assessed as increase in nitric oxide level after 10 ...	23791569
Arginase	Ki	=	200.0	nM	6.7	Noncompetitive inhibition of Leishmania amazonensis recombinant arginase express...	24521209
Alkaline phosphatase, tissue-nonspecific isozyme	IC50	=	407.0	nM	6.39	PUBCHEM_BIOASSAY: Dose Response confirmation of uHTS inhibitors of Mouse Intesti...	-
Alpha-synuclein	IC50	=	800.0	nM	6.1	Inhibition of alpha-synuclein fibril formation (unknown origin) incubated for 24...	30743095
Pyruvate kinase PKM	IC50	=	1330.0	nM	5.88	Inhibition of recombinant PKM2 (unknown origin) Asp177, Ser77, Gly52, Gly128 res...	34726055
Intestinal-type alkaline phosphatase	IC50	=	1360.0	nM	5.87	PUBCHEM_BIOASSAY: Dose Response confirmation of uHTS hits from a small molecule ...	-
Aspartyl aminopeptidase	IC50	=	1376.0	nM	5.86	PUBCHEM_BIOASSAY: QFRET-based biochemical high throughput dose response assay fo...	-
DNA repair protein RAD52 homolog	IC50	=	1450.0	nM	5.84	Inhibition of RAD52 (unknown origin) assessed as reduction in RAD52-ssDNA intera...	-
NON-PROTEIN TARGET	IC50	=	1590.0	nM	5.8	Antioxidant activity assessed as superoxide-scavenging activity by nitrite metho...	9461655
Arginase	IC50	=	1600.0	nM	5.8	Inhibition of Leishmania amazonensis recombinant arginase expressed in Escherich...	24521209
Prostaglandin G/H synthase 1	IC50	=	2000.0	nM	5.7	Inhibition of peroxidase activity of COX1 in heep seminal vesicle by TMPD assay	15568761
Unchecked	IC50	=	2800.0	nM	5.55	Inhibition of beta amyloid (1 to 40) fibril formation by thioflavin T staining-b...	19931462
No relevant target	EC50	=	4100.0	nM	5.39	Antioxidant activity assessed as H2O2 scavenging activity after 15 mins	25625705
Beta-secretase 1	IC50	=	4500.0	nM	5.35	Inhibition of human BACE-1	29763806
Amyloid-beta precursor protein	IC50	=	5300.0	nM	5.28	Inhibition of amyloid beta (unknown origin) aggregation	29763806
Unchecked	IC50	=	5600.0	nM	5.25	Inhibition of beta amyloid (1 to 42) fibril formation by thioflavin T staining-b...	19931462
Prostaglandin G/H synthase 1	IC50	=	12200.0	nM	4.91	Inhibition of cyclooxygenase activity of COX1 in sheep seminal vesicle in presen...	15568761
LNCaP	EC50	=	13000.0	nM	4.89	Decrease in androgen receptor protein expression in LNCaP cells by Western blott...	17383188
No relevant target	IC50	=	13600.0	nM	4.87	Antiglycation activity assessed as inhibition of advanced glycation end product ...	24131240
No relevant target	IC50	=	15000.0	nM	4.82	Antioxidant activity assessed as DPPH radical scavenging activity incubated for ...	28006914

Literature References

PubMed	DOI	Target Context	# Activities
23791569	10.1016/j.bmcl.2013.05.079	Molecular identity unknown	11
24794111	10.1016/j.bmcl.2014.04.038	Unchecked	10
26517554	10.1021/acs.jnatprod.5b00075	ADMET	10
24610996	10.1007/s00044-013-0829-4	Prothrombin	9
24485782	10.1016/j.bmcl.2014.01.028	NON-PROTEIN TARGET	7
28202328	10.1016/j.bmcl.2017.01.083	Unchecked	7
17228868	10.1021/jm060817o	Unchecked	6
6875579	10.1021/np50026a018	Rattus norvegicus	6
11000024	10.1021/np000128u	Escherichia coli	5
21824690	10.1016/j.ejmech.2011.07.031	HepG2	5
15568761	10.1021/np0498410	Prostaglandin G/H synthase 1	5
25625705	10.1021/np5007873	No relevant target	5
27623545	10.1016/j.bmcl.2016.08.094	NON-PROTEIN TARGET	5
24485782	10.1016/j.bmcl.2014.01.028	Tartrate-resistant acid phosphatase type 5	4
24794111	10.1016/j.bmcl.2014.04.038	Nitric oxide synthase 3	4
26238320	10.1016/j.bmcl.2015.07.056	RAW264.7	4
21493073	10.1016/j.bmc.2011.03.040	3T3-L1	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
23145924	10.1021/jf303290g	Diplodia seriata	4
12568546	10.1021/jf020978a	Linaria genistifolia subsp. dalmatica	3

Data from ChEMBL 36 via Core Engine