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Compound Detail

CHEMBL297453

EPIGALOCATECHIN GALLATE
🧪 Phase III
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🧪 Phase III
O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1

Basic Information

ChEMBL ID CHEMBL297453
Name EPIGALOCATECHIN GALLATE
Phase Phase III
Structure Type MOL
InChI Key WMBWREPUVVBILR-WIYYLYMNSA-N

Known Names

(-)-epigallocatechin gallate Epigalocatechin gallate
126
Targets
268
Activities
4
Assay Types
8
PK Parameters
20
Publications
2
Known Names
20
Indications

Molecular Properties

458.4
MW (Da)
2.23
ALogP
11
HBA
8
HBD
197.4
PSA (Ų)
0.21
QED
2
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Unknown

Flags

Natural Product

Extended Properties

Molecular Formula C22H18O11
MW 458.38
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness 1.65

Indications

Condylomata Acuminata Leiomyoma Lichen Planus, Oral Multiple System Atrophy Alzheimer Disease Amyloidosis, Familial Brain Injuries Breast Neoplasms Carcinoma, Intraductal, Noninfiltrating Diabetes Mellitus, Type 2 Down Syndrome Endometriosis Epidermolysis Bullosa Dystrophica Fragile X Syndrome Huntington Disease Inflammation Liver Cirrhosis Lung Neoplasms Lupus Erythematosus, Systemic Lymphoma, Follicular

Activity Summary

IC50 222 meas. best 7.52
EC50 19 meas. best 7.4
Ki 17 meas. best 8.1
Kd 10 meas. best 7.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Enoyl-acyl-carrier protein reductase
CHEMBL4150
Ki 8.1 7.31 8.0 3
Unchecked
CHEMBL612545
Ki 7.6 7.2233 25.0 3
Orphan methyltransferase M.SssI
CHEMBL4373
Ki 7.55 7.55 28.0 1
Fatty acid synthase
CHEMBL4512
IC50 7.52 6.96 30.0 2
PC-12
CHEMBL612556
IC50 7.52 7.52 30.0 1
Small ribosomal subunit protein uS2
CHEMBL6119
Kd 7.4 7.4 39.9 1
SH-SY5Y
CHEMBL614910
EC50 7.4 7.4 39.9 1
Plasmodium falciparum
CHEMBL364
IC50 7.14 5.758 73.0 5
Dual specificity protein kinase CLK1
CHEMBL4224
IC50 7.14 7.14 71.6 1
Proteasome Macropain subunit MB1
CHEMBL4662
IC50 7.07 5.94 86.0 3
Unchecked
CHEMBL612545
IC50 7.07 5.4497 86.0 32
Lethal factor
CHEMBL4372
IC50 7.01 7.01 97.0 1
A disintegrin and metalloproteinase with thrombospondin motifs 5
CHEMBL2285
IC50 7.0 7.0 100.0 1
A disintegrin and metalloproteinase with thrombospondin motifs 4
CHEMBL2318
IC50 7.0 7.0 100.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
IC50 6.91 6.91 122.6 2
Amyloid-beta precursor protein
CHEMBL2487
IC50 6.85 5.7933 140.0 6
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL2292
IC50 6.7 6.303 200.0 10
Enoyl-acyl-carrier protein reductase
CHEMBL4150
IC50 6.7 6.65 200.0 2
Apoptosis regulator Bcl-2
CHEMBL4860
Ki 6.63 6.55 234.4 2
Glucose-6-phosphate 1-dehydrogenase
CHEMBL1075249
IC50 6.6 6.6 250.0 1
DNA repair protein RAD52 homolog
CHEMBL2362978
IC50 6.56 5.904 277.0 5
3-oxoacyl-acyl-carrier protein reductase
CHEMBL4513
IC50 6.52 6.52 300.0 1
3-oxoacyl-(Acyl-carrier protein) reductase
CHEMBL2424511
IC50 6.5 6.5 320.0 1
Serine/threonine-protein kinase mTOR
CHEMBL2842
Ki 6.5 6.5 320.0 1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL5508
IC50 6.48 6.48 330.0 1
Latent membrane protein 1
CHEMBL1795089
Kd 6.44 6.44 360.0 1
GroEL/GroES
CHEMBL4106139
IC50 6.44 6.34 360.0 2
Casein kinase I isoform epsilon
CHEMBL4937
IC50 6.44 6.44 365.0 1
BCL2L10/BID
CHEMBL5169272
IC50 6.44 6.44 360.0 1
Tyrosine-protein kinase Fyn
CHEMBL1841
Kd 6.43 6.43 367.0 1
Dual specificity protein kinase CLK4
CHEMBL4203
IC50 6.43 6.43 367.7 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
CHEMBL4005
Ki 6.42 6.42 380.0 1
Influenza A virus
CHEMBL613740
EC50 6.41 4.8725 391.0 4
Transthyretin
CHEMBL3194
Kd 6.4 6.4 400.0 2
Cyclin-dependent kinase 5/CDK5 activator 1
CHEMBL1907600
IC50 6.37 6.37 431.0 1
BCL2/BID
CHEMBL5169265
IC50 6.35 6.35 450.0 1
Phosphoglycerate mutase 1
CHEMBL3334418
IC50 6.31 6.31 490.0 2
BCL2/BAD
CHEMBL5169266
Ki 6.31 6.31 490.0 1
DNA (cytosine-5)-methyltransferase 1
CHEMBL1993
IC50 6.3 6.3 500.0 1
Bcl-xL/BH3-interacting domain death agonist
CHEMBL3883285
IC50 6.23 6.23 590.0 1
Squalene monooxygenase
CHEMBL4241
IC50 6.16 6.16 690.0 2
Signal transducer and activator of transcription 1-alpha/beta
CHEMBL6101
Kd 6.16 6.16 700.0 1
Dual specificity tyrosine-phosphorylation-regulated kinase 1B
CHEMBL5543
IC50 6.15 6.15 713.6 1
Zinc finger protein mex-5
CHEMBL1293319
EC50 6.14 6.14 727.0 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
IC50 6.14 6.14 730.0 1
6-phosphogluconate dehydrogenase, decarboxylating
CHEMBL3404
IC50 6.14 6.14 720.0 1
Replicase polyprotein 1ab
CHEMBL4523582
IC50 6.14 5.97 720.0 2
Beta-secretase 1
CHEMBL4822
IC50 6.12 5.9067 757.0 3
Induced myeloid leukemia cell differentiation protein Mcl-1/BH3-interacting domain death agonist
CHEMBL3430886
IC50 6.04 6.04 920.0 1
Unchecked
CHEMBL612545
Kd 6.02 5.33 956.3 2

Pharmacokinetic Data

Parameter Value Units Species
Cmax 5000.0 nM Mus musculus
Cmax 12000.0 nM Mus musculus
F 5.0 % Rattus norvegicus
F 12.0 % Mus musculus
T1/2 2.0 hr Homo sapiens
T1/2 0.02167 hr Homo sapiens
Tmax 0.5 hr Mus musculus
Tmax 0.08333 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Enoyl-acyl-carrier protein reductase Ki = 8.0 nM 8.1 Inhibition of Plasmodium falciparum ENR in presence of triclosan 17263522
Unchecked Ki = 25.0 nM 7.6 Binding affinity to rat brain cell membrane 24794111
Unchecked Ki = 25.0 nM 7.6 Displacement of [3H]resveratrol from Sprague-Dawley rat brain plasma membranes a... 28654265
Orphan methyltransferase M.SssI Ki = 28.0 nM 7.55 Competitive inhibition of Spiroplasma sp. MQ1 SssI methyltransferase using pUC18... 22854677
PC-12 IC50 = 30.0 nM 7.52 Neuroprotective activity against rat PC12 cells assessed as decrease in H2O2-ind... 38295689
Fatty acid synthase IC50 = 30.0 nM 7.52 Inhibition of recombinant Plasmodium falciparum FabZ using crotonoyl-CoA as subs... 24063369
Small ribosomal subunit protein uS2 Kd = 39.9 nM 7.4 Binding affinity to His-tagged Laminin receptor in human A549 cells assessed as ... 37951136
SH-SY5Y EC50 = 39.87 nM 7.4 Neuroprotection against beta-amyloid peptide 1-42-induced toxicity in human SH-S... 19138859
Plasmodium falciparum IC50 = 73.0 nM 7.14 Antimalarial activity against chloroquine-sensitive/mefloquine-resistant Plasmod... 25488841
Dual specificity protein kinase CLK1 IC50 = 71.6 nM 7.14 Inhibition of recombinant human CLK1 expressed in Sf9 insect cells incubated for... 36876904
Enoyl-acyl-carrier protein reductase Ki = 79.0 nM 7.1 Inhibition of Plasmodium falciparum ENR using crotonyl-CoA substrate 17263522
Proteasome Macropain subunit MB1 IC50 = 86.0 nM 7.07 Inhibition of chymotrypsin-like activity of purified human 20S proteasome assess... 30776692
Unchecked IC50 = 86.0 nM 7.07 Inhibition of chymotrypsin like activity of proteasome 20045338
Lethal factor IC50 = 97.0 nM 7.01 Inhibition of Bacillus anthracis lethal factor 34624823
A disintegrin and metalloproteinase with thrombospondin motifs 4 IC50 = 100.0 nM 7.0 Inhibition of ADAMTS-4 (unknown origin) 36250680
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 100.0 nM 7.0 Inhibition of ADAMTS-5 (unknown origin) 36250680
ATP-dependent translocase ABCB1 IC50 = 122.6 nM 6.91 Modulation of P-gp (unknown origin) transfected in human MDA435/LCC6MDR cells as... 25985195
Unchecked IC50 = 122.6 nM 6.91 Reversal of Pgp-mediated paclitaxel resistance in human LCC6MDR cells assessed a... 34597896
Unchecked IC50 = 124.1 nM 6.91 Reversal of Pgp-mediated paclitaxel resistance in human LCC6MDR cells assessed a... 34597896
ATP-dependent translocase ABCB1 IC50 = 124.1 nM 6.91 Modulation of P-gp (unknown origin) transfected in human MDA435/LCC6MDR cells as... 25985195

Literature References

PubMed DOI Target Context # Activities
26267658 10.1021/acs.jnatprod.5b00471 Staphylococcus aureus 62
18195068 10.1128/aac.00825-07 Human alphaherpesvirus 1 38
18195068 10.1128/aac.00825-07 Human alphaherpesvirus 2 36
22225636 10.1016/j.bmcl.2011.12.034 Beta-secretase 1 23
21434603 10.1021/np1007729 Raji 22
21434603 10.1021/np1007729 HL-60 13
34509160 10.1016/j.bmc.2021.116394 H9c2 12
26517554 10.1021/acs.jnatprod.5b00075 ADMET 10
24456004 10.1021/np4007712 A-431 10
- 10.1007/s00044-012-0352-z Rattus norvegicus 9
31503486 10.1021/acs.jnatprod.9b00632 Leishmania infantum 9
28325635 10.1016/j.bmc.2017.03.023 Unchecked 9
21309591 10.1021/np1008202 Molecular identity unknown 8
10937722 10.1016/s0960-894x(00)00314-0 Human gammaherpesvirus 4 8
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 8
23327877 10.1021/np3007292 CHO 7
31422225 10.1016/j.ejmech.2019.111597 Fatty acid synthase 7
22413845 10.1021/jm201191d Telomerase reverse transcriptase 6
22413845 10.1021/jm201191d Unchecked 6
20004577 10.1016/j.bmcl.2009.11.109 Neutrophil elastase 6

Data from ChEMBL 36 via Core Engine