Epicatechin-(4beta->8)-epigallocatechin 3'-gallate

Details

• Internal ID: e65b91d2-245b-4957-9f67-626b3776b24e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: [(2R,3R)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• SMILES (Canonical): C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C(=C6)O)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O
• SMILES (Isomeric): C1[C@H]([C@H](OC2=C1C(=CC(=C2[C@@H]3[C@H]([C@H](OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C(=C6)O)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O
• InChI: InChI=1S/C37H30O17/c38-15-8-20(42)28-26(9-15)52-35(12-1-2-17(39)19(41)3-12)33(50)30(28)29-21(43)11-18(40)16-10-27(53-37(51)14-6-24(46)32(49)25(47)7-14)34(54-36(16)29)13-4-22(44)31(48)23(45)5-13/h1-9,11,27,30,33-35,38-50H,10H2/t27-,30-,33-,34-,35-/m1/s1
• InChI Key: BUOLDWJIICQRBU-RGOYVLDUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₃₀O₁₇
• Molecular Weight: 746.60 g/mol
• Exact Mass: 746.14829948 g/mol
• Topological Polar Surface Area (TPSA): 308.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.68
• H-Bond Acceptor: 17
• H-Bond Donor: 13
• Rotatable Bonds: 5

Synonyms

• DTXSID901099079
• Epicatechin-(4beta->8)-epigallocatechin 3'-gallate
• (2R)-2alpha-(3,4,5-Trihydroxyphenyl)-8-[[(2R)-2alpha-(3,4-dihydroxyphenyl)-3alpha,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran]-4beta-yl]-3,4-dihydro-2H-1-benzopyran-3alpha,5,7-triol 3-(3,4,5-trihydroxybenzoate)
• (2R,2'R,3R,3'R,4R)-2-(3,4-Dihydroxyphenyl)-3,3',4,4'-tetrahydro-3,5,5',7,7'-pentahydroxy-2'-(3,4,5-trihydroxyphenyl)[4,8'-bi-2H-1-benzopyran]-3'-yl 3,4,5-trihydroxybenzoate
• 126715-89-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8063	80.63%
Caco-2	-	0.9132	91.32%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6485	64.85%
OATP2B1 inhibitior	-	0.7027	70.27%
OATP1B1 inhibitior	+	0.8528	85.28%
OATP1B3 inhibitior	-	0.4057	40.57%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8943	89.43%
P-glycoprotein inhibitior	+	0.7069	70.69%
P-glycoprotein substrate	-	0.6548	65.48%
CYP3A4 substrate	+	0.6743	67.43%
CYP2C9 substrate	-	0.7962	79.62%
CYP2D6 substrate	-	0.7126	71.26%
CYP3A4 inhibition	-	0.7658	76.58%
CYP2C9 inhibition	-	0.8173	81.73%
CYP2C19 inhibition	-	0.7636	76.36%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.8594	85.94%
CYP2C8 inhibition	+	0.8162	81.62%
CYP inhibitory promiscuity	-	0.8411	84.11%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6439	64.39%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.8812	88.12%
Skin irritation	-	0.6484	64.84%
Skin corrosion	-	0.9586	95.86%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8650	86.50%
Micronuclear	+	0.8659	86.59%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8408	84.08%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7292	72.92%
Acute Oral Toxicity (c)	IV	0.3703	37.03%
Estrogen receptor binding	+	0.7906	79.06%
Androgen receptor binding	+	0.8033	80.33%
Thyroid receptor binding	+	0.5658	56.58%
Glucocorticoid receptor binding	+	0.5807	58.07%
Aromatase binding	-	0.5814	58.14%
PPAR gamma	+	0.6762	67.62%
Honey bee toxicity	-	0.7491	74.91%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9003	90.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.64%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.71%	91.49%
CHEMBL3194	P02766	Transthyretin	96.38%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.64%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.67%	97.09%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	92.53%	83.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	91.32%	96.12%
CHEMBL2535	P11166	Glucose transporter	91.28%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.19%	89.00%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	90.95%	96.37%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.51%	95.17%
CHEMBL4040	P28482	MAP kinase ERK2	89.14%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.09%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.77%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.90%	99.23%
CHEMBL4208	P20618	Proteasome component C5	86.43%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.69%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.31%	95.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.97%	95.89%
CHEMBL2581	P07339	Cathepsin D	83.72%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.45%	95.56%
CHEMBL236	P41143	Delta opioid receptor	82.69%	99.35%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.32%	94.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	81.31%	97.53%

Plants that contains it

• Aldama oblongifolia
• Artemisia schimperi
• Cajanus trinervius
• Elephantopus mollis
• Euryops algoensis
• Gardenia jasminoides
• Gomortega keule
• Iris ensata
• Litsea pungens
• Nuphar lutea
• Petasites hybridus
• Phoenix loureiroi
• Phyllanthus emblica
• Picea mariana
• Platanus orientalis
• Quercus robur
• Rhodiola semenovii
• Salvia parryi
• Staphylea ternata
• Thalictrum longistylum
• Viburnum urceolatum
• Xyris pterygoblephara

Cross-Links

• PubChem: 11513300
• NPASS: NPC194264
• LOTUS: LTS0107649
• wikiData: Q102165851