Epigallocatechin-3-O-gallate - Compound Card

Epigallocatechin-3-O-gallate

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Epigallocatechin-3-O-gallate

Structure
Zoomed Structure
  • Family: Plantae - Rhamnaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Acid Derivative
Canonical Smiles Oc1cc(O)c2c(c1)O[C@@H]([C@@H](C2)OC(=O)c1cc(O)c(c(c1)O)O)c1cc(O)c(c(c1)O)O
InChI InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1
InChIKey WMBWREPUVVBILR-WIYYLYMNSA-N
Formula C22H18O11
HBA 11
HBD 8
MW 458.38
Rotatable Bonds 3
TPSA 197.37
LogP 2.23
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.14
Exact Mass 458.08
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia retusa Euphorbiaceae Plantae 1091645
2 Limoniastrum guyonianum Plumbaginaceae Plantae 114145
3 Caesalpinia welwitschiana Leguminosae/Fabaceae Plantae 1387604
4 Eugenia edulis Myrtaceae Plantae 2729927
5 Ziziphus jujuba Rhamnaceae Plantae 326968

Showing of synonyms

  • Ben Mahmoud K, Wasli H, et al. (2022). Antidiabetic, antioxidant and chemical functionalities of Ziziphus jujuba (Mill.) and Moringa oleifera (Lam.) plants using multivariate data treatment. South African Journal of Botany, 2022, 144, 219-228. [View]
  • Essoung FRE, Mba'ning BM, et al. (2021). Antifeedant and ovicidal activities of a new cassane and other compounds from Caesalpinia welwitschiana Oliv. and Caesalpinia bonduc L. against Tuta absoluta (Lepidoptera: Gelechiidae).. Natural product research,2021, 35(24), 5681-5691. [View] [PubMed]
  • Lahmadi S, Belhamra M, et al. (2020). Phenolic constituents and antioxidant activity of Euphorbia retusa Forssk. Natural product research,2020, 34(24), 3545-3547. [View] [PubMed]
  • Trabelsi N, Oueslati S, et al. (2013). Phenolic contents and biological activities of Limoniastrum guyonianum fractions obtained by Centrifugal Partition Chromatography. Industrial Crops and Products,2013,49,740-746. [View]
  • Hussein S.A, Hashem A.N, et al. (2003). Polyoxygenated flavonoids from Eugenia edulis. Phytochemistry, 2003, 64(4), 883-9. [View] [PubMed]
Pubchem: 65064
Kegg Ligand: C09731
Chebi: 4806
Nmrshiftdb2: 60021287
Metabolights: MTBLC4806
Drugbank: DB12116
Pdb Ligand: KDH
Bindingdb: 50070942
CPRiL: 17217
Structure

SMILES: c1ccccc1C(=O)OC(C2)C(c3ccccc3)Oc(c24)cccc4

Level: 2

Mol. Weight: 458.38 g/mol

Structure

SMILES: c1ccccc1C(=O)OC(C2)COc(c23)cccc3

Level: 1

Mol. Weight: 458.38 g/mol

Structure

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 458.38 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 458.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 458.38 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-7.1
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.81
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.76
Plasma Protein Binding
85.53
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.7
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.36
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.83
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.08
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-93.93
Rat (Acute)
2.41
Rat (Chronic Oral)
3.9
Fathead Minnow
3.88
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
666.79
Hydration Free Energy
-4.5
Log(D) at pH=7.4
1.18
Log(P)
1.42
Log S
-4.08
Log(Vapor Pressure)
-10.05
Melting Point
263.54
pKa Acid
7.99
pKa Basic
9.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9535
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9535
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8856
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8856
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.8799
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.8799
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8758
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8758
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8727
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8727
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.8636
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.8636
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8525
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8525
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8479
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8479
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8467
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8467
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8421
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8421
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8400
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8400
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.8333
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.8333
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8120
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8120
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8100
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8100
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8076
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8076
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7986
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7986
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7733
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7733
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7726
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7726
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7611
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7611
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7586
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7586
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7560
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7560
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7445
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7445
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7427
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7427
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7382
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7382
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7356
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7356
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7341
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7341
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7307
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7307
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7294
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7294
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7285
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7285
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7273
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7273
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7228
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7228
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7157
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7157
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7153
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7153
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7081
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7081
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7059
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7059
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7041
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7041
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7041
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7041
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7038
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7038
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7038
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7038
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7014
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7014

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