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

Details

• Internal ID: 1f1fea95-99ed-4edf-ad12-2490f4628ab5
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5-[(1S,2S)-6-[(E)-2-[(2R,3R)-3-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1H-inden-1-yl]benzene-1,3-diol
• SMILES (Canonical): C1C(C(C2=CC(=C(C=C21)O)C=CC3=CC4=C(C=C3)OC(C4C5=C6C(C(OC6=CC(=C5)O)C7=CC=C(C=C7)O)C8=CC(=CC(=C8)O)O)C9=CC=C(C=C9)O)C1=CC(=CC(=C1)O)O)C1=CC=C(C=C1)O
• SMILES (Isomeric): C1[C@@H]([C@H](C2=CC(=C(C=C21)O)/C=C/C3=CC4=C(C=C3)O[C@H]([C@@H]4C5=C6[C@@H]([C@H](OC6=CC(=C5)O)C7=CC=C(C=C7)O)C8=CC(=CC(=C8)O)O)C9=CC=C(C=C9)O)C1=CC(=CC(=C1)O)O)C1=CC=C(C=C1)O
• InChI: InChI=1S/C57H44O11/c58-37-10-4-30(5-11-37)45-23-34-24-49(66)33(22-46(34)52(45)35-18-40(61)25-41(62)19-35)3-1-29-2-16-50-47(17-29)54(57(67-50)32-8-14-39(60)15-9-32)48-27-44(65)28-51-55(48)53(36-20-42(63)26-43(64)21-36)56(68-51)31-6-12-38(59)13-7-31/h1-22,24-28,45,52-54,56-66H,23H2/b3-1+/t45-,52-,53+,54+,56-,57+/m1/s1
• InChI Key: SPVHTVMXBGFLEG-IKQHZLIHSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₇H₄₄O₁₁
• Molecular Weight: 904.90 g/mol
• Exact Mass: 904.28836222 g/mol
• Topological Polar Surface Area (TPSA): 201.00 Ų
• XlogP: 10.50
• Atomic LogP (AlogP): 11.21
• H-Bond Acceptor: 11
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9762	97.62%
Caco-2	-	0.8701	87.01%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6160	61.60%
OATP2B1 inhibitior	-	0.7097	70.97%
OATP1B1 inhibitior	+	0.7404	74.04%
OATP1B3 inhibitior	+	0.8849	88.49%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8112	81.12%
P-glycoprotein inhibitior	+	0.7420	74.20%
P-glycoprotein substrate	-	0.6883	68.83%
CYP3A4 substrate	+	0.6414	64.14%
CYP2C9 substrate	+	0.7818	78.18%
CYP2D6 substrate	+	0.4405	44.05%
CYP3A4 inhibition	+	0.6656	66.56%
CYP2C9 inhibition	+	0.9423	94.23%
CYP2C19 inhibition	+	0.8530	85.30%
CYP2D6 inhibition	-	0.7496	74.96%
CYP1A2 inhibition	+	0.8968	89.68%
CYP2C8 inhibition	+	0.8298	82.98%
CYP inhibitory promiscuity	+	0.9677	96.77%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Danger	0.4585	45.85%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8826	88.26%
Skin irritation	-	0.5126	51.26%
Skin corrosion	-	0.9239	92.39%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8550	85.50%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	-	0.6915	69.15%
skin sensitisation	-	0.7344	73.44%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7315	73.15%
Acute Oral Toxicity (c)	II	0.3975	39.75%
Estrogen receptor binding	+	0.7347	73.47%
Androgen receptor binding	+	0.7824	78.24%
Thyroid receptor binding	+	0.5849	58.49%
Glucocorticoid receptor binding	+	0.5574	55.74%
Aromatase binding	-	0.4867	48.67%
PPAR gamma	+	0.7059	70.59%
Honey bee toxicity	-	0.7020	70.20%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9809	98.09%

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	99.61%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.55%	91.49%
CHEMBL242	Q92731	Estrogen receptor beta	92.55%	98.35%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.23%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.36%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.14%	89.00%
CHEMBL3194	P02766	Transthyretin	91.07%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.60%	94.45%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.42%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.44%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.18%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.96%	99.15%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.90%	89.62%
CHEMBL217	P14416	Dopamine D2 receptor	86.79%	95.62%
CHEMBL3401	O75469	Pregnane X receptor	83.78%	94.73%
CHEMBL206	P03372	Estrogen receptor alpha	83.60%	97.64%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.27%	85.14%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.35%	91.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.30%	86.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.92%	95.78%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.86%	85.11%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.15%	100.00%
CHEMBL4208	P20618	Proteasome component C5	80.88%	90.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.77%	93.99%

Plants that contains it

• Vitis amurensis
• Vitis davidi
• Vitis heyneana

Cross-Links

• PubChem: 101992975
• LOTUS: LTS0271605
• wikiData: Q104400235