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

Details

• Internal ID: 3daf0587-e8b1-4326-b560-f1657e6452e3
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 4-[(2S,3S)-3-(3,5-dihydroxyphenyl)-4-hydroxy-6-[(2S,3S)-4-hydroxy-2-(4-hydroxyphenyl)-6-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]-2,3-dihydro-1-benzofuran-2-yl]benzene-1,3-diol
• SMILES (Canonical): C1=CC(=CC=C1C=CC2=CC(=C3C(C(OC3=C2)C4=CC=C(C=C4)O)C5=CC(=C6C(C(OC6=C5)C7=C(C=C(C=C7)O)O)C8=CC(=CC(=C8)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C2=CC(=C3[C@@H]([C@H](OC3=C2)C4=CC=C(C=C4)O)C5=CC(=C6[C@@H]([C@H](OC6=C5)C7=C(C=C(C=C7)O)O)C8=CC(=CC(=C8)O)O)O)O)O
• InChI: InChI=1S/C42H32O10/c43-26-7-3-21(4-8-26)1-2-22-13-33(49)39-35(14-22)51-41(23-5-9-27(44)10-6-23)37(39)25-17-34(50)40-36(18-25)52-42(31-12-11-28(45)20-32(31)48)38(40)24-15-29(46)19-30(47)16-24/h1-20,37-38,41-50H/b2-1+/t37-,38-,41+,42+/m0/s1
• InChI Key: LSXNDESCRJSFBR-LCCNWPCHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₃₂O₁₀
• Molecular Weight: 696.70 g/mol
• Exact Mass: 696.19954721 g/mol
• Topological Polar Surface Area (TPSA): 180.00 Ų
• XlogP: 7.30
• Atomic LogP (AlogP): 8.03
• H-Bond Acceptor: 10
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	-	0.8833	88.33%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5535	55.35%
OATP2B1 inhibitior	+	0.5756	57.56%
OATP1B1 inhibitior	+	0.8336	83.36%
OATP1B3 inhibitior	+	0.8015	80.15%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8171	81.71%
P-glycoprotein inhibitior	+	0.7284	72.84%
P-glycoprotein substrate	-	0.7814	78.14%
CYP3A4 substrate	+	0.5941	59.41%
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	+	0.7705	77.05%
CYP inhibitory promiscuity	+	0.9650	96.50%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Danger	0.4413	44.13%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.8137	81.37%
Skin irritation	+	0.5125	51.25%
Skin corrosion	-	0.9324	93.24%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7543	75.43%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.6315	63.15%
skin sensitisation	-	0.6900	69.00%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.6265	62.65%
Acute Oral Toxicity (c)	II	0.4136	41.36%
Estrogen receptor binding	+	0.7132	71.32%
Androgen receptor binding	+	0.7985	79.85%
Thyroid receptor binding	+	0.6693	66.93%
Glucocorticoid receptor binding	+	0.6943	69.43%
Aromatase binding	-	0.5128	51.28%
PPAR gamma	+	0.7423	74.23%
Honey bee toxicity	-	0.8041	80.41%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
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	97.68%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.79%	91.49%
CHEMBL3192	Q9BY41	Histone deacetylase 8	94.96%	93.99%
CHEMBL3194	P02766	Transthyretin	93.75%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.70%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.85%	89.00%
CHEMBL2581	P07339	Cathepsin D	87.98%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	87.55%	94.73%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	86.44%	96.42%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.13%	91.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.01%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.79%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.50%	93.40%
CHEMBL226	P30542	Adenosine A1 receptor	83.14%	95.93%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.84%	99.15%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.56%	89.67%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.86%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.82%	86.33%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.08%	96.12%

Plants that contains it

• Gnetum gnemon
• Gnetum klossii
• Gnetum latifolium
• Spirotropis longifolia

Cross-Links

• PubChem: 5318947
• NPASS: NPC122306
• LOTUS: LTS0117148
• wikiData: Q105156826