5-[(2R,3R)-7-hydroxy-5-[(2S,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

Details

• Internal ID: 413ab2a1-1d84-487c-b943-3d7861b2764f
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5-[(2R,3R)-7-hydroxy-5-[(2S,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
• SMILES (Canonical): C1=CC(=CC=C1C=CC2=C3C(C(OC3=CC(=C2)O)C4=CC=C(C=C4)O)C5=CC6=C(C(=C5)O)OC(C6C7=CC(=CC(=C7)O)O)C8=CC=C(C=C8)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C2=C3[C@@H]([C@H](OC3=CC(=C2)O)C4=CC=C(C=C4)O)C5=CC6=C(C(=C5)O)O[C@H]([C@@H]6C7=CC(=CC(=C7)O)O)C8=CC=C(C=C8)O)O
• InChI: InChI=1S/C42H32O9/c43-28-9-2-22(3-10-28)1-4-25-15-33(48)21-36-38(25)39(41(50-36)24-7-13-30(45)14-8-24)27-18-34-37(26-16-31(46)20-32(47)17-26)40(51-42(34)35(49)19-27)23-5-11-29(44)12-6-23/h1-21,37,39-41,43-49H/b4-1+/t37-,39+,40+,41-/m1/s1
• InChI Key: OBOUYBKGROJMIK-XRBKDVKHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₃₂O₉
• Molecular Weight: 680.70 g/mol
• Exact Mass: 680.20463259 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: 7.70
• Atomic LogP (AlogP): 8.33
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9826	98.26%
Caco-2	-	0.8740	87.40%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.4804	48.04%
OATP2B1 inhibitior	+	0.5734	57.34%
OATP1B1 inhibitior	+	0.8129	81.29%
OATP1B3 inhibitior	+	0.7950	79.50%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8240	82.40%
P-glycoprotein inhibitior	+	0.7390	73.90%
P-glycoprotein substrate	-	0.7921	79.21%
CYP3A4 substrate	+	0.5737	57.37%
CYP2C9 substrate	+	0.6202	62.02%
CYP2D6 substrate	+	0.3681	36.81%
CYP3A4 inhibition	+	0.6322	63.22%
CYP2C9 inhibition	+	0.8880	88.80%
CYP2C19 inhibition	+	0.6752	67.52%
CYP2D6 inhibition	-	0.7996	79.96%
CYP1A2 inhibition	+	0.8603	86.03%
CYP2C8 inhibition	+	0.7925	79.25%
CYP inhibitory promiscuity	+	0.9561	95.61%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Danger	0.3983	39.83%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.7787	77.87%
Skin irritation	+	0.5234	52.34%
Skin corrosion	-	0.9200	92.00%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8510	85.10%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	-	0.5972	59.72%
skin sensitisation	-	0.6271	62.71%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.4711	47.11%
Acute Oral Toxicity (c)	II	0.4035	40.35%
Estrogen receptor binding	+	0.7207	72.07%
Androgen receptor binding	+	0.7825	78.25%
Thyroid receptor binding	+	0.6817	68.17%
Glucocorticoid receptor binding	+	0.6568	65.68%
Aromatase binding	-	0.5678	56.78%
PPAR gamma	+	0.7494	74.94%
Honey bee toxicity	-	0.7575	75.75%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9736	97.36%

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	98.96%	91.11%
CHEMBL3194	P02766	Transthyretin	96.25%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.79%	95.56%
CHEMBL242	Q92731	Estrogen receptor beta	90.00%	98.35%
CHEMBL1951	P21397	Monoamine oxidase A	88.48%	91.49%
CHEMBL230	P35354	Cyclooxygenase-2	88.36%	89.63%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.06%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	86.67%	94.73%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.40%	93.99%
CHEMBL4040	P28482	MAP kinase ERK2	84.97%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.50%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.22%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.39%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.34%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.63%	86.33%
CHEMBL1808	P12821	Angiotensin-converting enzyme	80.73%	93.39%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.56%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.00%	99.17%

Plants that contains it

• Acacia adunca
• Adiantum philippense
• Aldama incana
• Annona cornifolia
• Artemisia pedemontana subsp. assoana
• Astragalus sempervirens
• Calostephane divaricata
• Caragana aurantiaca
• Chaenomeles sinensis
• Dumortiera hirsuta
• Echeveria secunda
• Eucalyptus melliodora
• Gnetum latifolium
• Goniothalamus malayanus
• Hedysarum inundatum
• Hypericum laricifolium
• Ipomoea digitata
• Lepisorus ussuriensis
• Lysimachia mauritiana
• Marrubium anisodon
• Naucleopsis ternstroemiiflora
• Ocotea pittieri
• Pastinaca sativa
• Peltostigma guatemalense
• Premna odorata
• Rauvolfia vomitoria
• Rhodanthe chlorocephala subsp. rosea
• Rumex maritimus
• Salvia syriaca
• Scutellaria amoena
• Solanum laxum
• Swertia franchetiana
• Vaccinium oxycoccos
• Vitis vinifera
• Wikstroemia retusa
• Zanthoxylum tetraspermum

Cross-Links

• PubChem: 102004665
• NPASS: NPC307147