(-)-EPICATECHIN

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Synonyms
Status
Molecule Category UNKNOWN
UNII 34PHS7TU43
EPA CompTox DTXSID4045133

Structure

InChI Key PFTAWBLQPZVEMU-UKRRQHHQSA-N
Smiles Oc1cc(O)c2c(c1)O[C@H](c1ccc(O)c(O)c1)[C@H](O)C2
InChI
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H14O6
Molecular Weight 290.27
AlogP 1.55
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 5.0
Number of Rotational Bond 1.0
Polar Surface Area 110.38
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 21.0
Assay Description Organism Bioactivity Reference
Inhibition of FAS at 100 uM Homo sapiens 10.2 %
Antioxidant activity assessed as DPPH radical scavenging activity None 1.7 ug.mL-1
Inhibition of aldose reductase in rat lens homogenate at 30 uM Rattus norvegicus 41.0 %
Inhibition of Saccharomyces cerevisiae fatty acid synthase Saccharomyces cerevisiae 50.0 ug.mL-1
Antifungal activity against Candida albicans ATCC 90028 Candida albicans 50.0 ug.mL-1
Antifungal activity against Cryptococcus neoformans ATCC 90113 Cryptococcus neoformans 50.0 ug.mL-1
Antioxidant activity assessed as DPPH radical scavenging activity None 8.5 ug.mL-1
Antifungal activity against Giardia intestinalis Giardia intestinalis 1.0 ug.mL-1
Hepatoprotective activity against mouse hepatocytes assessed as inhibition of D-galactosamine/TNFalpha-induced cell death at 50 uM after 18 hrs by MTT assay Mus musculus 38.0 %
Hepatoprotective activity against mouse hepatocytes assessed as inhibition of D-galactosamine/TNFalpha-induced cell death at 100 uM after 18 hrs by MTT assay Mus musculus 58.1 %
Hepatoprotective activity against mouse hepatocytes assessed as inhibition of D-galactosamine/TNFalpha-induced cell death at 200 uM after 18 hrs by MTT assay Mus musculus 98.9 %
Antiviral activity against HIV infected in human MT4 cells assessed as inhibition of virus-induced cytopathic effect by MTT assay Human immunodeficiency virus 34.1 ug.mL-1
Inhibition of human salivary alpha-amylase Homo sapiens 10.3 %
Inhibition of reduced carboxymethylated kappa-casein fibril formation at 50 ug/mL measured every 5 mins after 1000 mins by thioflavin T staining-based binding assay None 7.0 %
Antiaggregatory activity in human platelets assessed as inhibition of collagen-induced platelet aggregation by aggregometry Homo sapiens 22.22 ug.mL-1
Antiaggregatory activity in human platelets assessed as inhibition of thrombin-induced platelet aggregation by aggregometry Homo sapiens 50.0 ug.mL-1
PUBCHEM_BIOASSAY: Dose Response confirmation of uHTS inhibitors of Mouse Intestinal Alkaline Phosphatase using Tissue Nonspecific Alkaline Phosphatase. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID2806, AID2818] Homo sapiens 407.0 nM
Antifilarial activity against adult Brugia malayi assessed as inhibition of motility at 31.25 ug/ml incubated for 48 hrs followed by washout measured after 1 hr in the absence of drug by microscopic analysis Brugia malayi 50.0 %
Antifilarial activity against microfilariae Brugia malayi assessed as inhibition of motility at 31.25 ug/ml incubated for 48 hrs followed by washout measured after 1 hr in the absence of drug by microscopic analysis Brugia malayi 50.0 %
Antifilarial activity against adult Brugia malayi at 31.25 ug/ml by MTT assay relative to control Brugia malayi 34.8 %
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method Electrophorus electricus -4.81 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method Equus caballus 0.47 %
Antioxidant activity assessed as inhibition of DPPH radical production after 30 min by spectrophotometric analysis None 1.61 ug.mL-1
Antioxidant activity assessed as inhibition of ABTS radical production after 10 min by spectrophotometric analysis None 1.83 ug.mL-1
Antiamoebic activity against Entamoeba histolytica Entamoeba histolytica 1.92 ug.mL-1
Activation of eNOS in BCAEC assessed as increase in nitric oxide level after 10 mins by fluorometric analysis Bos taurus 2.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 80.37 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 77.92 %
Noncompetitive inhibition of Leishmania amazonensis recombinant arginase expressed in Escherichia coli Rosetta (DE3) pLysS using L-arginine as substrate by Dixon reciprocal plot analysis Leishmania amazonensis 200.0 nM
Inhibition of rat intestinal sucrase using p-nitrophenyl-alpha-d-glucopyranoside as substrate at 1 mM incubated for 10 mins prior to substrate addition measured after 5 mins by spectrophotometry Rattus norvegicus 61.88 %
Inhibition of TRAP activity in RANKL-induced Balb/c mouse RAW264.7 cells at 10 uM after 1 hr by ELISA relative to control Mus musculus 83.96 %
Inhibition of TRAP activity in Balb/c mouse RAW264.7 cells at 10 uM after 1 hr by ELISA relative to control Mus musculus 170.62 %
Inhibition of TRAP activity in RANKL-induced Balb/c mouse RAW264.7 cells at 1 uM after 1 hr by ELISA relative to control Mus musculus 78.28 %
Inhibition of TRAP activity in Balb/c mouse RAW264.7 cells at 1 uM after 1 hr by ELISA relative to control Mus musculus 159.09 %
Antioxidant activity in rat liver microsomes assessed as inhibition of NADPH-dependent lipid peroxidation Rattus norvegicus 29.0 ug.mL-1
Antioxidant activity assessed as inhibition of linoleic acid autooxidation None 0.62 ug.mL-1
Antioxidant activity assessed as DPPH radical scavenging activity None 0.62 ug.mL-1
Anti-inflammatory activity in LPS-stimulated mouse RAW264.7 cells assessed as inhibition of nitric oxide production at 40 uM by Griess reaction based ELISA method Mus musculus 91.8 %
Antichlamydial activity against Chlamydia pneumoniae K7 infected in HL cells assessed as chlamydial inhibition at 50 uM after 70 hrs by fluorescent microscopic analysis Chlamydia pneumoniae 41.7 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 83.11 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 8.66 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.12 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.11 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.12 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.11 %
Inhibition of alpha-synuclein fibril formation (unknown origin) incubated for 24 hrs to 7 days by thioflavin S based fluorescence assay Homo sapiens 800.0 nM

Related Entries

Cross References

Resources Reference
ChEBI 90
ChEMBL CHEMBL583912
DrugBank DB12039
FDA SRS 34PHS7TU43
Human Metabolome Database HMDB0001871
KEGG C09727
PDB 28E
SureChEMBL SCHEMBL19412
ZINC ZINC000000119988
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