8-[5-(5,7-Dihydroxy-4-oxo-chromen-2-yl)-2-methoxy-phenyl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-chromen-4-one

Details

• Internal ID: 7f5f9053-7513-42c6-b6bd-962d6cdb8622
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxyphenyl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O)C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)O)O)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O)C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)O)O)OC
• InChI: InChI=1S/C32H22O10/c1-39-24-8-5-16(26-12-21(36)30-20(35)10-18(34)11-28(30)41-26)9-19(24)29-27(40-2)14-23(38)31-22(37)13-25(42-32(29)31)15-3-6-17(33)7-4-15/h3-14,33-35,38H,1-2H3
• InChI Key: OVCFMRWVQJAWDY-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₂₂O₁₀
• Molecular Weight: 566.50 g/mol
• Exact Mass: 566.12129689 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.74
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 4',7''-Dimethoxyamentoflavone
• 8-[5-(5,7-Dihydroxy-4-oxo-4H-chromen-2-yl)-2-methoxy-phenyl]-5-hydroxy-2-(4-hydroxy-phenyl)-7-methoxy-chromen-4-one
• 8-[5-(5,7-dihydroxy-4-oxo-chromen-2-yl)-2-methoxy-phenyl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9325	93.25%
Caco-2	-	0.7507	75.07%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8148	81.48%
OATP2B1 inhibitior	-	0.5693	56.93%
OATP1B1 inhibitior	-	0.4918	49.18%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9055	90.55%
P-glycoprotein inhibitior	+	0.8634	86.34%
P-glycoprotein substrate	-	0.5412	54.12%
CYP3A4 substrate	+	0.6356	63.56%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.5831	58.31%
CYP2C9 inhibition	+	0.6590	65.90%
CYP2C19 inhibition	+	0.6234	62.34%
CYP2D6 inhibition	-	0.7411	74.11%
CYP1A2 inhibition	+	0.6533	65.33%
CYP2C8 inhibition	+	0.9140	91.40%
CYP inhibitory promiscuity	+	0.6726	67.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6328	63.28%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.8347	83.47%
Skin irritation	-	0.7256	72.56%
Skin corrosion	-	0.9363	93.63%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6923	69.23%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9458	94.58%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.4878	48.78%
Acute Oral Toxicity (c)	III	0.6505	65.05%
Estrogen receptor binding	+	0.9020	90.20%
Androgen receptor binding	+	0.9399	93.99%
Thyroid receptor binding	+	0.6414	64.14%
Glucocorticoid receptor binding	+	0.8740	87.40%
Aromatase binding	+	0.5799	57.99%
PPAR gamma	+	0.7493	74.93%
Honey bee toxicity	-	0.7217	72.17%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5949	59.49%
Fish aquatic toxicity	+	0.9066	90.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL242	Q92731	Estrogen receptor beta	97.41%	98.35%
CHEMBL3194	P02766	Transthyretin	97.28%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.85%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.84%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.17%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.78%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.62%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.87%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.18%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	90.61%	95.78%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.37%	96.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.34%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.13%	95.64%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	84.90%	83.57%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.69%	97.28%
CHEMBL1951	P21397	Monoamine oxidase A	84.41%	91.49%
CHEMBL4208	P20618	Proteasome component C5	84.02%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.98%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.68%	86.92%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.36%	99.23%
CHEMBL2535	P11166	Glucose transporter	82.73%	98.75%
CHEMBL301	P24941	Cyclin-dependent kinase 2	82.71%	91.23%
CHEMBL1255126	O15151	Protein Mdm4	82.56%	90.20%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	81.40%	97.03%
CHEMBL3401	O75469	Pregnane X receptor	81.07%	94.73%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.99%	91.71%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	80.32%	89.23%

Plants that contains it

• Araucaria cunninghamii
• Cephalotaxus nana

Cross-Links

• PubChem: 5494869
• NPASS: NPC215203
• LOTUS: LTS0247216
• wikiData: Q105200618