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Epicatechin-3-O-rhamnoside

Family: Plantae - Fagaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavanol

Canonical Smiles	Oc1cc(O)c2c(c1)OC(C(C2)OC1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C21H24O10/c1-8-17(26)18(27)19(28)21(29-8)31-16-7-11-13(24)5-10(22)6-15(11)30-20(16)9-2-3-12(23)14(25)4-9/h2-6,8,16-28H,7H2,1H3/t8-,16?,17-,18+,19+,20?,21?/m1/s1
InChIKey	KYLFHITXPCWYAL-QYBXBSDFSA-N
Formula	C₂₁H₂₄O₁₀
HBA	10
HBD	7
MW	436.41
Rotatable Bonds	3
TPSA	169.3
LogP	0.4
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.43
Exact Mass	436.14
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Quercus ilex	Fagaceae	Plantae	58334

Showing of synonyms

Castejón M.L, Rosillo M.Á, et al. (2019). Quercus ilex extract ameliorates acute TNBS-induced colitis in rats. Planta medica, 2019, 85(8), 670-677. [View] [PubMed]

Pubchem: 54020287

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2)OC4CCCCO4

Level: 2

Mol. Weight: 436.41 g/mol

SMILES: c1cccc(c12)OCC(C2)OC3CCCCO3

Level: 1

Mol. Weight: 436.41 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 436.41 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 436.41 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 436.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 436.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.89
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.73
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.67

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.8
Plasma Protein Binding: 46.37
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: Non-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: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 16.03
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.2
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.7
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.43
Micronucleos: Toxic
NR-AhR: Safe
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: -40.33
Rat (Acute): 2.22
Rat (Chronic Oral): 3.86
Fathead Minnow: 3.8
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 571.97
Hydration Free Energy: -7.58
Log(D) at pH=7.4: 0.43
Log(P): 0.1
Log S: -3.83
Log(Vapor Pressure): -10.93
Melting Point: 174.84
pKa Acid: 6.0
pKa Basic: 7.11

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.9026
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8847
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8835
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8752
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8615
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8534
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8471
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8441
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8343
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8317
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8271
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8224
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8214
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8156
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8125
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8104
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7965
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7936
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7893
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7861
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7754
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7750
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7742
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7714
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7706
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	4	0.7692
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7659
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7635
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7600
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7479
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7475
Mitogen-activated protein kinase 14	P47811	MK14_MOUSE	Mus musculus	5	0.7451
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7441
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7430
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7422
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7387
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7362
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7346
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7316
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7286
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7285
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7263
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7246
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7214
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7163
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7132
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7130
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7123
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7053
Leucine--tRNA ligase	P07813	SYL_ECOLI	Escherichia coli	3	0.7042
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7034
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7032
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7019
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7018
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7002

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