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

Details

• Internal ID: eb830744-bd9d-4c54-b3f8-9b738b3013ae
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5-[(2S,3S)-4-[(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]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
• SMILES (Canonical): C1=CC(=CC=C1C2C(C3=C(C=C(C=C3O2)O)C=CC4=CC5=C(C=C4)OC(C5C6=C7C(C(OC7=CC(=C6)O)C8=CC=C(C=C8)O)C9=CC(=CC(=C9)O)O)C1=CC=C(C=C1)O)C1=CC(=CC(=C1)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@@H]2[C@H](C3=C(C=C(C=C3O2)O)/C=C/C4=CC5=C(C=C4)O[C@H]([C@@H]5C6=C7[C@@H]([C@H](OC7=CC(=C6)O)C8=CC=C(C=C8)O)C9=CC(=CC(=C9)O)O)C1=CC=C(C=C1)O)C1=CC(=CC(=C1)O)O)O
• InChI: InChI=1S/C56H42O12/c57-35-10-4-29(5-11-35)54-50(33-19-38(60)23-39(61)20-33)49-32(18-42(64)26-47(49)67-54)3-1-28-2-16-46-44(17-28)52(56(66-46)31-8-14-37(59)15-9-31)45-25-43(65)27-48-53(45)51(34-21-40(62)24-41(63)22-34)55(68-48)30-6-12-36(58)13-7-30/h1-27,50-52,54-65H/b3-1+/t50-,51-,52-,54+,55+,56-/m0/s1
• InChI Key: WZKKRZSJTLGPHH-QGYUWUKLSA-N
• Popularity: 2 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

• CHEMBL2230305

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	-	0.8738	87.38%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5535	55.35%
OATP2B1 inhibitior	-	0.7072	70.72%
OATP1B1 inhibitior	+	0.7566	75.66%
OATP1B3 inhibitior	+	0.8015	80.15%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7660	76.60%
P-glycoprotein inhibitior	+	0.7273	72.73%
P-glycoprotein substrate	-	0.8302	83.02%
CYP3A4 substrate	+	0.5685	56.85%
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	+	0.7844	78.44%
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	-	0.8652	86.52%
Skin irritation	+	0.5125	51.25%
Skin corrosion	-	0.9324	93.24%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8113	81.13%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.6431	64.31%
skin sensitisation	-	0.6900	69.00%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.5568	55.68%
Acute Oral Toxicity (c)	II	0.4136	41.36%
Estrogen receptor binding	+	0.7539	75.39%
Androgen receptor binding	+	0.8180	81.80%
Thyroid receptor binding	+	0.6360	63.60%
Glucocorticoid receptor binding	+	0.5886	58.86%
Aromatase binding	+	0.5533	55.33%
PPAR gamma	+	0.7441	74.41%
Honey bee toxicity	-	0.7501	75.01%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
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	98.96%	91.11%
CHEMBL3194	P02766	Transthyretin	92.87%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	90.97%	98.35%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.15%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.32%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.33%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.28%	99.15%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.15%	93.40%
CHEMBL3401	O75469	Pregnane X receptor	86.06%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.31%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.15%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.13%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	83.09%	91.49%
CHEMBL4040	P28482	MAP kinase ERK2	81.75%	83.82%
CHEMBL2581	P07339	Cathepsin D	81.64%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.74%	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: 16138152
• NPASS: NPC133209