5-[(2R,3R)-6-[(2R,3R)-5-[(E)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzouran-4-yl]ethenyl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzouran-3-yl]-4-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzouran-3-yl]benzene-1,3-diol

Details

• Internal ID: b91d7a5e-f2b2-43b8-ace6-a0fd5730c851
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5-[(2R,3R)-6-[(2R,3R)-5-[(E)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]-4-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
• SMILES (Canonical): C1=CC(=CC=C1C2C(C3=C(O2)C=CC(=C3)C=CC4=C5C(C(OC5=CC(=C4)O)C6=CC=C(C=C6)O)C7=CC(=CC(=C7)O)O)C8=CC(=C9C(C(OC9=C8)C1=CC=C(C=C1)O)C1=CC(=CC(=C1)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@H]2[C@@H](C3=C(O2)C=CC(=C3)/C=C/C4=C5[C@H]([C@@H](OC5=CC(=C4)O)C6=CC=C(C=C6)O)C7=CC(=CC(=C7)O)O)C8=CC(=C9[C@H]([C@@H](OC9=C8)C1=CC=C(C=C1)O)C1=CC(=CC(=C1)O)O)O)O
• InChI: InChI=1S/C56H42O12/c57-36-10-4-29(5-11-36)54-49(35-23-45(65)53-47(24-35)67-56(31-8-14-38(59)15-9-31)52(53)34-21-41(62)26-42(63)22-34)44-17-28(2-16-46(44)66-54)1-3-32-18-43(64)27-48-50(32)51(33-19-39(60)25-40(61)20-33)55(68-48)30-6-12-37(58)13-7-30/h1-27,49,51-52,54-65H/b3-1+/t49-,51-,52-,54+,55+,56+/m1/s1
• InChI Key: SPRFPODGXUUTIB-APEUUSFDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₆H₄₂O₁₂
• Molecular Weight: 906.90 g/mol
• Exact Mass: 906.26762677 g/mol
• Topological Polar Surface Area (TPSA): 210.00 Ų
• XlogP: 10.00
• Atomic LogP (AlogP): 11.00
• H-Bond Acceptor: 12
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

• DTXSID601029954
• Q7937133
• 5-[(2R,3R)-6-[(2R,3R)-5-[(E)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzouran-4-yl]ethenyl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzouran-3-yl]-4-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzouran-3-yl]benzene-1,3-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	-	0.8713	87.13%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5535	55.35%
OATP2B1 inhibitior	-	0.7060	70.60%
OATP1B1 inhibitior	+	0.7955	79.55%
OATP1B3 inhibitior	+	0.8015	80.15%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7662	76.62%
P-glycoprotein inhibitior	+	0.7339	73.39%
P-glycoprotein substrate	-	0.8284	82.84%
CYP3A4 substrate	+	0.5806	58.06%
CYP2C9 substrate	+	0.6202	62.02%
CYP2D6 substrate	+	0.3681	36.81%
CYP3A4 inhibition	+	0.6476	64.76%
CYP2C9 inhibition	+	0.9283	92.83%
CYP2C19 inhibition	+	0.8370	83.70%
CYP2D6 inhibition	-	0.8256	82.56%
CYP1A2 inhibition	+	0.8993	89.93%
CYP2C8 inhibition	+	0.8112	81.12%
CYP inhibitory promiscuity	+	0.9650	96.50%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Danger	0.4413	44.13%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.8720	87.20%
Skin irritation	+	0.5125	51.25%
Skin corrosion	-	0.9324	93.24%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8344	83.44%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.6434	64.34%
skin sensitisation	-	0.6900	69.00%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.5820	58.20%
Acute Oral Toxicity (c)	II	0.4136	41.36%
Estrogen receptor binding	+	0.7444	74.44%
Androgen receptor binding	+	0.7988	79.88%
Thyroid receptor binding	+	0.6202	62.02%
Glucocorticoid receptor binding	+	0.6073	60.73%
Aromatase binding	+	0.5281	52.81%
PPAR gamma	+	0.7350	73.50%
Honey bee toxicity	-	0.7725	77.25%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9801	98.01%

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	99.18%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	95.80%	83.82%
CHEMBL3194	P02766	Transthyretin	95.69%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	91.52%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.71%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.18%	95.56%
CHEMBL230	P35354	Cyclooxygenase-2	89.14%	89.63%
CHEMBL3401	O75469	Pregnane X receptor	87.39%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.80%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.70%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.65%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.06%	94.45%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.21%	91.71%
CHEMBL242	Q92731	Estrogen receptor beta	81.91%	98.35%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.37%	93.40%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.20%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.39%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.34%	96.00%

Plants that contains it

• Vitis coignetiae
• Vitis vinifera

Cross-Links

• PubChem: 16133855
• LOTUS: LTS0256771
• wikiData: Q7937133