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Epicatechin-O-hexoside

Family: Plantae - Tamaricaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavanol-O-Glycoside

Canonical Smiles	OCC1OC(OC2Cc3c(O)cc(cc3OC2c2ccc(c(c2)O)O)O)C(C(C1O)O)O
InChI	InChI=1S/C21H24O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8/h1-5,15-29H,6-7H2
InChIKey	YOVYWMDLYSJYPO-UHFFFAOYSA-N
Formula	C₂₁H₂₄O₁₁
HBA	11
HBD	8
MW	452.41
Rotatable Bonds	4
TPSA	189.53
LogP	-0.63
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.43
Exact Mass	452.13
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tamarix articulata	Tamaricaceae	Plantae	189786

Showing of synonyms

Shaalan Y.M, Handoussa H, et al. (2018). Destabilizing the interplay between miR-1275 and IGF2BPs by Tamarix articulata and quercetin in hepatocellular carcinoma. Nat Prod Res,2018,32(18),2217-2220. [View] [PubMed]

Pubchem: 14104301

Chebi: 191722

Nmrshiftdb2: 60029121

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 452.41 g/mol

SMILES: c1cccc(c12)OCC(C2)OC3CCCCO3

Level: 1

Mol. Weight: 452.41 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 452.41 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 452.41 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 452.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 452.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.92
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.77
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.85

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.75
Plasma Protein Binding: -5.06
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: 16.47
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.3
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.71
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.39
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: -68.5
Rat (Acute): 2.17
Rat (Chronic Oral): 3.95
Fathead Minnow: 3.82
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: 592.58
Hydration Free Energy: -4.91
Log(D) at pH=7.4: -0.29
Log(P): -0.72
Log S: -3.48
Log(Vapor Pressure): -11.48
Melting Point: 189.57
pKa Acid: 6.0
pKa Basic: 6.75

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8538
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.8506
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8502
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8337
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8334
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8302
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8174
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8173
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8084
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8038
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7922
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7871
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7812
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7744
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	4	0.7695
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7690
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7578
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7518
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7469
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7455
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7455
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7445
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7438
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7430
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7377
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7376
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7326
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7324
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7309
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7297
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7290
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7282
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7254
Isoflavone 4'-O-methyltransferase	Q29U70	I4OMT_MEDTR	Medicago truncatula	4	0.7230
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.7183
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7174
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7156
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7123
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7120
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7111
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7061
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7055
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7005
Dihydrofolate reductase	Q81R22	Q81R22_BACAN	Bacillus anthracis	4	0.7001
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7001

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