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Epicatechin-3-O-gallate

Family: Plantae - Fagaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Glycosylated Flavonol

Canonical Smiles	Oc1cc(O)c2c(c1)OC(C(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
InChIKey	LSHVYAFMTMFKBA-UHFFFAOYSA-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	Quercus ilex	Fagaceae	Plantae	58334

Showing of synonyms

Hadidi L, Babou L, et al. (2017). Quercus ilex L.: How season, plant organ and extraction procedure can influence chemistry and bioactivities. Chemistry & Biodiversity, 2017, 14(1),. [View] [PubMed]

Pubchem: 367141

Gnps: CCMSLIB00000578444

Chebi: 191849

Nmrshiftdb2: 60033228

Chembl: CHEMBL328085

Bindingdb: 50105591

CPRiL: 17216

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

Level: 2

Mol. Weight: 442.38 g/mol

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

Level: 1

Mol. Weight: 442.38 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 442.38 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 442.38 g/mol

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: 68.36
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: -1.17
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.97
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.24
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: -61.11
Rat (Acute): 2.42
Rat (Chronic Oral): 3.54
Fathead Minnow: 4.14
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: 618.23
Hydration Free Energy: -5.16
Log(D) at pH=7.4: 1.9
Log(P): 1.83
Log S: -4.21
Log(Vapor Pressure): -9.82
Melting Point: 259.55
pKa Acid: 8.0
pKa Basic: 7.92

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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