8-(3-Hydroxy-4-methoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-7-one

Details

• Internal ID: c9d82a06-20a2-47d6-aae0-53b8739be1d2
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > O-methylated isoflavonoids > 4-O-methylated isoflavonoids > 3-hydroxy,4-methoxyisoflavonoids
• IUPAC Name: 8-(3-hydroxy-4-methoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-7-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=COC3=C(C2=O)C=CC4=C3OC(C(O4)C5=CC(=C(C=C5)O)OC)CO)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=COC3=C(C2=O)C=CC4=C3OC(C(O4)C5=CC(=C(C=C5)O)OC)CO)O
• InChI: InChI=1S/C26H22O9/c1-31-19-7-4-13(9-18(19)29)16-12-33-25-15(23(16)30)5-8-20-26(25)35-22(11-27)24(34-20)14-3-6-17(28)21(10-14)32-2/h3-10,12,22,24,27-29H,11H2,1-2H3
• InChI Key: BICMHQBPOYXGKM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₂O₉
• Molecular Weight: 478.40 g/mol
• Exact Mass: 478.12638228 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.76
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9506	95.06%
Caco-2	-	0.7456	74.56%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8272	82.72%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.8870	88.70%
OATP1B3 inhibitior	+	0.8108	81.08%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9147	91.47%
P-glycoprotein inhibitior	+	0.8784	87.84%
P-glycoprotein substrate	-	0.7772	77.72%
CYP3A4 substrate	+	0.6408	64.08%
CYP2C9 substrate	-	0.8253	82.53%
CYP2D6 substrate	-	0.7787	77.87%
CYP3A4 inhibition	-	0.6377	63.77%
CYP2C9 inhibition	+	0.5533	55.33%
CYP2C19 inhibition	+	0.5184	51.84%
CYP2D6 inhibition	-	0.8889	88.89%
CYP1A2 inhibition	-	0.7789	77.89%
CYP2C8 inhibition	+	0.7399	73.99%
CYP inhibitory promiscuity	+	0.6788	67.88%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7113	71.13%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.8627	86.27%
Skin irritation	-	0.8220	82.20%
Skin corrosion	-	0.9722	97.22%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8088	80.88%
Micronuclear	+	0.6859	68.59%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6145	61.45%
Acute Oral Toxicity (c)	III	0.6902	69.02%
Estrogen receptor binding	+	0.9044	90.44%
Androgen receptor binding	+	0.8433	84.33%
Thyroid receptor binding	+	0.6217	62.17%
Glucocorticoid receptor binding	+	0.8587	85.87%
Aromatase binding	-	0.4903	49.03%
PPAR gamma	+	0.6932	69.32%
Honey bee toxicity	-	0.7457	74.57%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.4066	40.66%

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	98.91%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.53%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.95%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.15%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.60%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.56%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.37%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.87%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.62%	95.56%
CHEMBL3438	Q05513	Protein kinase C zeta	91.00%	88.48%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.46%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.39%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.29%	95.78%
CHEMBL1907	P15144	Aminopeptidase N	86.60%	93.31%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.53%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.61%	80.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.06%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.77%	92.62%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	82.75%	92.38%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	82.25%	85.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.80%	97.28%

Plants that contains it

• Xanthocercis zambesiaca

Cross-Links

• PubChem: 14058045
• LOTUS: LTS0261202
• wikiData: Q104936376