(2R,3R)-2-(3,4-dihydroxyphenyl)-3-(3,5-dihydroxyphenyl)-2,3-dihydronaphtho[2,1-e][1]benzofuran-7,8,10-triol

Details

• Internal ID: 24a3e143-a3dd-4e54-8dac-7d2b44438d3e
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2R,3R)-2-(3,4-dihydroxyphenyl)-3-(3,5-dihydroxyphenyl)-2,3-dihydronaphtho[2,1-e][1]benzofuran-7,8,10-triol
• SMILES (Canonical): C1=CC(=C(C=C1C2C(C3=C(O2)C=C(C4=C3C=CC5=CC(=C(C=C54)O)O)O)C6=CC(=CC(=C6)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1[C@H]2[C@@H](C3=C(O2)C=C(C4=C3C=CC5=CC(=C(C=C54)O)O)O)C6=CC(=CC(=C6)O)O)O)O
• InChI: InChI=1S/C28H20O8/c29-15-5-14(6-16(30)9-15)25-27-17-3-1-12-7-21(33)22(34)10-18(12)26(17)23(35)11-24(27)36-28(25)13-2-4-19(31)20(32)8-13/h1-11,25,28-35H/t25-,28+/m1/s1
• InChI Key: HJVFPIFXFXQWKU-NAKRPHOHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₀O₈
• Molecular Weight: 484.50 g/mol
• Exact Mass: 484.11581759 g/mol
• Topological Polar Surface Area (TPSA): 151.00 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 5.20
• H-Bond Acceptor: 8
• H-Bond Donor: 7
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9571	95.71%
Caco-2	-	0.8875	88.75%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5331	53.31%
OATP2B1 inhibitior	+	0.5756	57.56%
OATP1B1 inhibitior	+	0.9022	90.22%
OATP1B3 inhibitior	+	0.9293	92.93%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8018	80.18%
P-glycoprotein inhibitior	+	0.5808	58.08%
P-glycoprotein substrate	-	0.8385	83.85%
CYP3A4 substrate	+	0.5288	52.88%
CYP2C9 substrate	-	0.7818	78.18%
CYP2D6 substrate	+	0.4370	43.70%
CYP3A4 inhibition	-	0.6131	61.31%
CYP2C9 inhibition	+	0.5935	59.35%
CYP2C19 inhibition	-	0.7359	73.59%
CYP2D6 inhibition	-	0.8731	87.31%
CYP1A2 inhibition	+	0.8808	88.08%
CYP2C8 inhibition	+	0.7785	77.85%
CYP inhibitory promiscuity	+	0.8440	84.40%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Warning	0.4235	42.35%
Eye corrosion	-	0.9890	98.90%
Eye irritation	+	0.6984	69.84%
Skin irritation	+	0.5240	52.40%
Skin corrosion	-	0.9049	90.49%
Ames mutagenesis	+	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8854	88.54%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.7043	70.43%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.5951	59.51%
Acute Oral Toxicity (c)	III	0.3644	36.44%
Estrogen receptor binding	+	0.6726	67.26%
Androgen receptor binding	+	0.8237	82.37%
Thyroid receptor binding	+	0.7162	71.62%
Glucocorticoid receptor binding	+	0.7323	73.23%
Aromatase binding	-	0.4874	48.74%
PPAR gamma	+	0.8005	80.05%
Honey bee toxicity	-	0.8429	84.29%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9554	95.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.55%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.36%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.79%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.05%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.47%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.62%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.15%	95.56%
CHEMBL3194	P02766	Transthyretin	83.21%	90.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.50%	92.94%

Plants that contains it

• Maackia amurensis
• Senna garrettiana

Cross-Links

• PubChem: 101631691
• LOTUS: LTS0022334
• wikiData: Q105029469