4-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-4-[(E)-2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-2-yl]benzene-1,2-diol

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	09656ae5-ac07-49d5-82f7-97f6089da473
Taxonomy	Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
IUPAC Name	4-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol
SMILES (Canonical)	C1=CC(=CC=C1C=CC2=C3C(C(OC3=CC(=C2)O)C4=CC(=C(C=C4)O)O)C5=CC(=CC(=C5)O)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)O)C5=CC(=CC(=C5)O)O)O
InChI	InChI=1S/C28H22O7/c29-19-6-2-15(3-7-19)1-4-16-9-22(32)14-25-26(16)27(18-10-20(30)13-21(31)11-18)28(35-25)17-5-8-23(33)24(34)12-17/h1-14,27-34H/b4-1+/t27-,28+/m1/s1
InChI Key	VJVQHVVOEFJLIO-YVYUXZJTSA-N
Popularity	2 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₈H₂₂O₇
Molecular Weight	470.50 g/mol
Exact Mass	470.13655304 g/mol
Topological Polar Surface Area (TPSA)	131.00 Å²
XlogP	5.00
Atomic LogP (AlogP)	5.36
H-Bond Acceptor	7
H-Bond Donor	6
Rotatable Bonds	4

Synonyms

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(2R,3R)-2beta-(3,4-Dihydroxyphenyl)-3alpha-(3,5-dihydroxyphenyl)-4-[2-(4-hydroxyphenyl)ethenyl]-2,3-dihydrobenzo[b]furan-6-ol

(trans)-1,2-Benzenediol, 4-[(2R,3R)-3-(3,5-dihydroxyphenyl)-2,3-dihydro-6-hydroxy-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2-benzofuranyl]-

2beta-(3,4-Dihydroxyphenyl)-3alpha-(3,5-dihydroxyphenyl)-4-(4-hydroxy-trans-styryl)-2,3-dihydrobenzofuran-6-ol

4-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-4-[(E)-2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-2-yl]benzene-1,2-diol

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9727	97.27%
Caco-2	-	0.8636	86.36%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.4187	41.87%
OATP2B1 inhibitior	+	0.5668	56.68%
OATP1B1 inhibitior	+	0.8869	88.69%
OATP1B3 inhibitior	+	0.9539	95.39%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7615	76.15%
P-glycoprotein inhibitior	+	0.5730	57.30%
P-glycoprotein substrate	-	0.9037	90.37%
CYP3A4 substrate	+	0.5209	52.09%
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	+	0.7700	77.00%
CYP inhibitory promiscuity	+	0.9240	92.40%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.3733	37.33%
Eye corrosion	-	0.9879	98.79%
Eye irritation	+	0.6201	62.01%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8948	89.48%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8336	83.36%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.6869	68.69%
skin sensitisation	-	0.6015	60.15%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.4662	46.62%
Acute Oral Toxicity (c)	II	0.3678	36.78%
Estrogen receptor binding	+	0.6218	62.18%
Androgen receptor binding	+	0.8404	84.04%
Thyroid receptor binding	+	0.7258	72.58%
Glucocorticoid receptor binding	+	0.7315	73.15%
Aromatase binding	+	0.5852	58.52%
PPAR gamma	+	0.8207	82.07%
Honey bee toxicity	-	0.8033	80.33%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9823	98.23%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	99.31%	91.11%
CHEMBL3194	P02766	Transthyretin	97.13%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	96.63%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.17%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.14%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.12%	99.15%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.23%	93.99%
CHEMBL3401	O75469	Pregnane X receptor	85.84%	94.73%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.98%	89.67%
CHEMBL242	Q92731	Estrogen receptor beta	84.40%	98.35%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.38%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.63%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.20%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.07%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	81.27%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.85%	94.45%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Artemisia pedemontana subsp. assoana

Astragalus sempervirens

Boehmeria nivea

Bolboschoenus fluviatilis

Bolboschoenus maritimus subsp. maritimus

Calostephane divaricata

Caragana aurantiaca