Epicatechin 3-O-gallate - Compound Card

Epicatechin 3-O-gallate

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Epicatechin 3-O-gallate

Structure
Zoomed Structure
  • Family: Plantae - Ximeniaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavan-3-Ol Gallate
Canonical Smiles Oc1cc(O)c2c(c1)O[C@@H]([C@@H](C2)OC(=O)c1cc(O)c(c(c1)O)O)c1ccc(c(c1)O)O
InChI InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1
InChIKey LSHVYAFMTMFKBA-TZIWHRDSSA-N
Formula C22H18O10
HBA 10
HBD 7
MW 442.38
Rotatable Bonds 3
TPSA 177.14
LogP 2.53
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.14
Exact Mass 442.09
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Rumex abyssinicus Polygonaceae Plantae 273505
2 Ximenia americana Ximeniaceae Plantae 50174

Showing of synonyms

  • Tala M, Ansary M, et al. (2018). Anthraquinones and flavanols isolated from the vegetable herb Rumex abyssinicus inhibit motility of Phytophthora capsici zoospores. South African Journal of Botany, 2018, 115, 1-4. [View]
  • Sobeh M, Mahmoud MF, et al. (2017). Hepatoprotective and hypoglycemic effects of a tannin rich extract from Ximenia americana var. caffra root. Phytomedicine : international journal of phytotherapy and phytopharmacology,2017, 33(), 36-42. [View] [PubMed]
CPRiL: 17216
Structure

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

Level: 2

Mol. Weight: 442.38 g/mol

Structure

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

Level: 1

Mol. Weight: 442.38 g/mol

Structure

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 442.38 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 442.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 442.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-7.08
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.46
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.88
Plasma Protein Binding
90.77
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.3
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.31
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.98
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.23
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
-62.58
Rat (Acute)
2.42
Rat (Chronic Oral)
3.54
Fathead Minnow
4.11
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
621.6
Hydration Free Energy
-5.16
Log(D) at pH=7.4
1.87
Log(P)
1.8
Log S
-4.23
Log(Vapor Pressure)
-10.01
Melting Point
261.04
pKa Acid
7.97
pKa Basic
7.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9592
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.9090
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.9033
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.8833
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8775
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8739
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8720
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8561
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8538
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8520
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8498
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8431
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8415
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8414
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8334
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8321
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8309
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8272
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8266
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8119
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8061
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.8054
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8052
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8033
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7992
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7977
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.7972
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7913
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7818
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7816
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7780
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7778
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7764
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7754
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7748
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7747
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7713
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7697
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7695
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7682
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7659
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7641
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7621
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7595
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7577
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7563
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7548
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7536
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7530
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7526
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7524
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7522
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7522
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7497
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7494
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7454
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7439
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7411
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7364
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7356
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7346
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7338
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7308
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7292
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7257
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7232
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7230
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7228
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7225
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7210
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7203
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7188
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7168
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7159
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7158
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7145
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7137
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7133
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7130
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7106
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7100
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7085
Kinesin heavy chain Q41460 Q41460_SOLTU Solanum tuberosum 3 0.7074
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7073
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7068
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7065
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7064
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7061
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 3 0.7059
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7059
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7059
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7050
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7047
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7044
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7027
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7003
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7000

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