(2R,2'R,3R,3'R)-2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromene-3,3',5,5',7,7'-hexol

Details

• Internal ID: 5f387294-3123-49a2-9ef1-fc8a28b6c636
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: (2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• 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
• SMILES (Isomeric): C1[C@H]([C@H](OC2=C1C(=CC(=C2C3[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
• InChI: InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26?,27-,28-,29-/m1/s1
• InChI Key: XFZJEEAOWLFHDH-ATEOAPGCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₆O₁₂
• Molecular Weight: 578.50 g/mol
• Exact Mass: 578.14242626 g/mol
• Topological Polar Surface Area (TPSA): 221.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.00
• H-Bond Acceptor: 12
• H-Bond Donor: 10
• Rotatable Bonds: 3

Synonyms

• SCHEMBL13006354
• XFZJEEAOWLFHDH-ATEOAPGCSA-N
• [(-)-Epicatechin-(-)-epicatechin]
• AKOS015960443
• AC-11170
• AC-34944
• Epicatechin-(4.beta.-8)-(-)-epicatechin
• 4,8-Bi(3,3',4',5,7-pentahydroxyflavane)
• (2R,2'R,3R,3'R)-2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromene-3,3',5,5',7,7'-hexol
• 4,8'-Bi[(2R)-3alpha,5,7-trihydroxy-3,4-dihydro-2alpha-(3,4-dihydroxyphenyl)-2H-1-benzopyran]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8698	86.98%
Caco-2	-	0.9107	91.07%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.4793	47.93%
OATP2B1 inhibitior	-	0.5605	56.05%
OATP1B1 inhibitior	+	0.9408	94.08%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9057	90.57%
P-glycoprotein inhibitior	+	0.6991	69.91%
P-glycoprotein substrate	-	0.8066	80.66%
CYP3A4 substrate	+	0.5743	57.43%
CYP2C9 substrate	-	0.5994	59.94%
CYP2D6 substrate	+	0.5264	52.64%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9155	91.55%
CYP2C8 inhibition	+	0.6770	67.70%
CYP inhibitory promiscuity	-	0.8625	86.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6139	61.39%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8204	82.04%
Skin irritation	-	0.6044	60.44%
Skin corrosion	-	0.9317	93.17%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8993	89.93%
Micronuclear	+	0.7859	78.59%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.7665	76.65%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6052	60.52%
Acute Oral Toxicity (c)	IV	0.5696	56.96%
Estrogen receptor binding	+	0.7555	75.55%
Androgen receptor binding	+	0.7545	75.45%
Thyroid receptor binding	+	0.6710	67.10%
Glucocorticoid receptor binding	+	0.5949	59.49%
Aromatase binding	-	0.5919	59.19%
PPAR gamma	+	0.7488	74.88%
Honey bee toxicity	-	0.7797	77.97%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.6855	68.55%

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	99.52%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	98.87%	83.82%
CHEMBL1951	P21397	Monoamine oxidase A	96.88%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.71%	96.09%
CHEMBL1929	P47989	Xanthine dehydrogenase	93.59%	96.12%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.66%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.86%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.20%	99.15%
CHEMBL2535	P11166	Glucose transporter	86.62%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.17%	95.56%
CHEMBL4208	P20618	Proteasome component C5	84.92%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	84.40%	94.73%
CHEMBL3194	P02766	Transthyretin	83.39%	90.71%
CHEMBL236	P41143	Delta opioid receptor	83.31%	99.35%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.46%	94.45%

Plants that contains it

• Aesculus hippocastanum
• Albizia lebbeck
• Apocynum venetum
• Areca catechu
• Calluna vulgaris
• Camellia sinensis
• Campylotropis hirtella
• Cassia fistula
• Cecropia glaziovii
• Chaenomeles sinensis
• Chaenomeles speciosa
• Cinnamomum aromaticum
• Cinnamomum bejolghota
• Cinnamomum sieboldii
• Cinnamomum verum
• Clusia sandiensis
• Coleogyne ramosissima
• Crataegus laevigata
• Crataegus monogyna
• Crataegus pinnatifida
• Crataegus sinaica
• Croton lechleri
• Cynomorium coccineum subsp. songaricum
• Davallia divaricata
• Dimocarpus longan
• Dioscorea cirrhosa
• Eriobotrya japonica
• Fagopyrum acutatum
• Fagopyrum esculentum
• Fragaria vesca
• Garcinia mangostana
• Guazuma ulmifolia
• Gymnosporia senegalensis
• Humulus lupulus
• Hypericum erectum
• Hypericum perforatum
• Juniperus sabina
• Kandelia candel
• Larix gmelinii
• Lindera umbellata
• Malus pumila
• Malus sylvestris
• Musanga cecropioides
• Nelia pillansii
• Nelumbo nucifera
• Prunus dulcis
• Psidium guajava
• Psorospermum febrifugum
• Reynoutria multiflora
• Ribes sanguineum
• Rosa rugosa
• Saraca asoca
• Saxifraga stolonifera
• Spatholobus suberectus
• Taxus mairei
• Theobroma cacao
• Thujopsis dolabrata
• Uncaria macrophylla
• Uncaria rhynchophylla
• Uncaria sinensis
• Urceola micrantha
• Vaccinium macrocarpon
• Vitis vinifera
• Ziziphus jujuba

Cross-Links

• PubChem: 5320711
• NPASS: NPC251619
• LOTUS: LTS0097406
• wikiData: Q104252503