epigallocatechin-(4beta->8)-epigallocatechin-3-O-gallate

Details

• Internal ID: 4485fade-f438-4b3d-84c5-96b3d673007f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-8-[(2R,3R,4R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-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)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)O)C6=CC(=C(C(=C6)O)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O
• InChI: InChI=1S/C37H30O18/c38-14-7-17(40)27-25(8-14)53-35(12-3-21(44)31(49)22(45)4-12)33(51)29(27)28-18(41)10-16(39)15-9-26(54-37(52)13-5-23(46)32(50)24(47)6-13)34(55-36(15)28)11-1-19(42)30(48)20(43)2-11/h1-8,10,26,29,33-35,38-51H,9H2/t26-,29-,33-,34-,35-/m1/s1
• InChI Key: JSBXKZFDEDBAQA-WUFIRYPCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₃₀O₁₈
• Molecular Weight: 762.60 g/mol
• Exact Mass: 762.14321410 g/mol
• Topological Polar Surface Area (TPSA): 328.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.39
• H-Bond Acceptor: 18
• H-Bond Donor: 14
• Rotatable Bonds: 5

Synonyms

• epigallocatechin-(4beta->8)-epigallocatechin-3-O-gallate
• CHEMBL161077
• SCHEMBL13934799
• DTXSID201301146
• Prodelphinidin B 2, 3'-O-gallate
• [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-8-[(2R,3R,4R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• Q27136632
• [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-8-[(2R,3R,4R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-4-yl]chroman-3-yl] 3,4,5-trihydroxybenzoate
• 5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-8-(3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-4-yl)chroman-3-yl 3,4,5-trihydroxybenzoate
• 86588-88-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8063	80.63%
Caco-2	-	0.9089	90.89%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6485	64.85%
OATP2B1 inhibitior	-	0.7026	70.26%
OATP1B1 inhibitior	+	0.8130	81.30%
OATP1B3 inhibitior	-	0.4057	40.57%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8832	88.32%
P-glycoprotein inhibitior	+	0.7027	70.27%
P-glycoprotein substrate	-	0.6614	66.14%
CYP3A4 substrate	+	0.6563	65.63%
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	+	0.7635	76.35%
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	-	0.8835	88.35%
Skin irritation	-	0.6484	64.84%
Skin corrosion	-	0.9586	95.86%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8506	85.06%
Micronuclear	+	0.8659	86.59%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8408	84.08%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.6646	66.46%
Acute Oral Toxicity (c)	IV	0.3703	37.03%
Estrogen receptor binding	+	0.7873	78.73%
Androgen receptor binding	+	0.7928	79.28%
Thyroid receptor binding	+	0.5614	56.14%
Glucocorticoid receptor binding	+	0.5656	56.56%
Aromatase binding	-	0.5759	57.59%
PPAR gamma	+	0.6682	66.82%
Honey bee toxicity	-	0.7728	77.28%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
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	99.33%	91.11%
CHEMBL3194	P02766	Transthyretin	94.89%	90.71%
CHEMBL4040	P28482	MAP kinase ERK2	92.72%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.21%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.63%	95.17%
CHEMBL1929	P47989	Xanthine dehydrogenase	91.23%	96.12%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.51%	89.00%
CHEMBL2535	P11166	Glucose transporter	90.17%	98.75%
CHEMBL4302	P08183	P-glycoprotein 1	89.93%	92.98%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	89.92%	96.37%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.90%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.75%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	89.68%	91.49%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	89.10%	83.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.44%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.59%	99.23%
CHEMBL1993	P26358	DNA (cytosine-5)-methyltransferase 1	87.07%	95.44%
CHEMBL2581	P07339	Cathepsin D	84.41%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.35%	94.00%
CHEMBL4208	P20618	Proteasome component C5	83.62%	90.00%
CHEMBL236	P41143	Delta opioid receptor	82.63%	99.35%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.55%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.40%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.61%	95.56%

Plants that contains it

• Alyxia reinwardtii
• Centaurea linifolia
• Cneoridium dumosum
• Leuzea centauroides
• Limonium gmelinii
• Machilus glaucescens
• Microtropis fokienensis
• Myrica rubra
• Parapiptadenia rigida
• Thymus vulgaris
• Vitellaria paradoxa

Cross-Links

• PubChem: 467305
• NPASS: NPC65333
• LOTUS: LTS0184384
• wikiData: Q27136632