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

Details

• Internal ID: d8c3731b-c916-4fc0-94ea-58de10a7dd5c
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 4-[3-(3,5-dihydroxyphenyl)-5-[2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol
• SMILES (Canonical): C1=CC(=C(C=C1C2C(C3=C(O2)C=C(C(=C3)C=CC4=CC(=CC(=C4)O)O)O)C5=CC(=CC(=C5)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2C(C3=C(O2)C=C(C(=C3)C=CC4=CC(=CC(=C4)O)O)O)C5=CC(=CC(=C5)O)O)O)O
• InChI: InChI=1S/C28H22O8/c29-18-5-14(6-19(30)11-18)1-2-15-9-22-26(13-24(15)34)36-28(16-3-4-23(33)25(35)10-16)27(22)17-7-20(31)12-21(32)8-17/h1-13,27-35H
• InChI Key: QOBRIVOFSCJJOV-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₂O₈
• Molecular Weight: 486.50 g/mol
• Exact Mass: 486.13146766 g/mol
• Topological Polar Surface Area (TPSA): 151.00 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 5.06
• H-Bond Acceptor: 8
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9727	97.27%
Caco-2	-	0.8773	87.73%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4187	41.87%
OATP2B1 inhibitior	+	0.5709	57.09%
OATP1B1 inhibitior	+	0.9186	91.86%
OATP1B3 inhibitior	+	0.9539	95.39%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7343	73.43%
P-glycoprotein inhibitior	+	0.6655	66.55%
P-glycoprotein substrate	-	0.9423	94.23%
CYP3A4 substrate	+	0.5264	52.64%
CYP2C9 substrate	+	0.6176	61.76%
CYP2D6 substrate	-	0.6658	66.58%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	+	0.6675	66.75%
CYP2C19 inhibition	-	0.6853	68.53%
CYP2D6 inhibition	-	0.8758	87.58%
CYP1A2 inhibition	+	0.8769	87.69%
CYP2C8 inhibition	+	0.7973	79.73%
CYP inhibitory promiscuity	+	0.9240	92.40%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.3733	37.33%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.5545	55.45%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8948	89.48%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8365	83.65%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.6015	60.15%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5416	54.16%
Acute Oral Toxicity (c)	II	0.3678	36.78%
Estrogen receptor binding	+	0.6529	65.29%
Androgen receptor binding	+	0.7250	72.50%
Thyroid receptor binding	+	0.7064	70.64%
Glucocorticoid receptor binding	+	0.7180	71.80%
Aromatase binding	-	0.4927	49.27%
PPAR gamma	+	0.8020	80.20%
Honey bee toxicity	-	0.6611	66.11%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9823	98.23%

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	99.38%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.90%	91.49%
CHEMBL3194	P02766	Transthyretin	95.77%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.61%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.56%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.01%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.51%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	87.81%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.15%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.73%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.54%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.49%	96.00%

Plants that contains it

• Morus macroura

Cross-Links

• PubChem: 162990244
• LOTUS: LTS0236621
• wikiData: Q105224779