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Epicatechin-3-O-(4''-O-methyl)gallate

Family: Plantae - Polygonaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Biflavone

Canonical Smiles	COc1cc(cc(c1O)O)C(=O)O[C@@H]1Cc2c(O)cc(cc2O[C@@H]1c1ccc(c(c1)O)O)O
InChI	InChI=1S/C23H20O10/c1-31-19-6-11(5-17(28)21(19)29)23(30)33-20-9-13-15(26)7-12(24)8-18(13)32-22(20)10-2-3-14(25)16(27)4-10/h2-8,20,22,24-29H,9H2,1H3/t20-,22-/m1/s1
InChIKey	XGTBMCGGGJLOPS-IFMALSPDSA-N
Formula	C₂₃H₂₀O₁₀
HBA	10
HBD	6
MW	456.4
Rotatable Bonds	4
TPSA	166.14
LogP	2.83
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.17
Exact Mass	456.11
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rumex abyssinicus	Polygonaceae	Plantae	273505

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]

Pubchem: 467296

Cas: 83104-86-3

Zinc: ZINC000014642643

Chebi: 136553

Nmrshiftdb2: 60072844

Metabolights: MTBLC136553

Chembl: CHEMBL158521

Bindingdb: 50296236

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 456.4 g/mol

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

Level: 1

Mol. Weight: 456.4 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 456.4 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 456.4 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 456.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.83
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.210
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.040
Plasma Protein Binding: 83.9
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: 13.220
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.080
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.320
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.380
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: -110.790
Rat (Acute): 2.440
Rat (Chronic Oral): 3.470
Fathead Minnow: 4.300
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 592.350
Hydration Free Energy: -3.740
Log(D) at pH=7.4: 2.610
Log(P): 2.17
Log S: -5.43
Log(Vapor Pressure): -9.37
Melting Point: 229.3
pKa Acid: 7.44
pKa Basic: 5.94

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9714
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.9202
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.9101
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.9080
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.9038
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9015
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8971
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8924
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8828
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8744
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8708
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8644
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8604
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8573
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8514
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8507
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8473
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8423
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8407
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8353
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8334
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8321
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.8305
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8259
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8255
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8224
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8164
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8159
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8148
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8133
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8127
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8107
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8056
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.8010
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7996
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7960
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	4	0.7940
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7840
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7829
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7820
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7805
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7798
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7798
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7784
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7781
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7772
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7740
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7723
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7714
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7711
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7702
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7695
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7688
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7637
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7621
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7596
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7594
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7587
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7584
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7583
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7548
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7543
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7542
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7522
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7492
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7471
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7466
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.7465
Cyclic nucleotide-binding protein	B8FW11	B8FW11_DESHD	Desulfitobacterium hafniense	3	0.7455
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7451
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7420
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7409
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.7407
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7353
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7346
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7339
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7333
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7330
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7322
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7318
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7315
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7313
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7301
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7296
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7278
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7275
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7267
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7263
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7262
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7239
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7239
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7231
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7220
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7216
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7212
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7211
Kinesin heavy chain	Q41460	Q41460_SOLTU	Solanum tuberosum	3	0.7211
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7211
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.7206
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.7203
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.7194
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7193
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7176
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7171
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7147
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7136
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7130
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.7127
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7099
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7098
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7091
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7082
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7081
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7080
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7078
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7053
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7049
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7022
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7021
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7021
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7019
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7017
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7012
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7011
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7007
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7005
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7002
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7001

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