6-Hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-9-phenyl-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-7-one

Details

• Internal ID: 1979391e-32fa-4ffb-8ef3-985390292b6c
• Taxonomy: Lignans, neolignans and related compounds > Flavonolignans
• IUPAC Name: 6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-9-phenyl-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-7-one
• InChI: InChI=1S/C25H20O8/c1-30-19-9-14(7-8-15(19)27)23-21(12-26)33-24-20(32-23)11-17(29)22-16(28)10-18(31-25(22)24)13-5-3-2-4-6-13/h2-11,21,23,26-27,29H,12H2,1H3
• InChI Key: FECLWLKPCOCFKF-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₀O₈
• Molecular Weight: 448.40 g/mol
• Exact Mass: 448.11581759 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.75
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9582	95.82%
Caco-2	-	0.7742	77.42%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8254	82.54%
OATP2B1 inhibitior	-	0.5665	56.65%
OATP1B1 inhibitior	+	0.8501	85.01%
OATP1B3 inhibitior	+	0.8959	89.59%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9073	90.73%
P-glycoprotein inhibitior	+	0.8915	89.15%
P-glycoprotein substrate	-	0.7816	78.16%
CYP3A4 substrate	+	0.5747	57.47%
CYP2C9 substrate	-	0.6235	62.35%
CYP2D6 substrate	-	0.8293	82.93%
CYP3A4 inhibition	-	0.7232	72.32%
CYP2C9 inhibition	+	0.7031	70.31%
CYP2C19 inhibition	+	0.5804	58.04%
CYP2D6 inhibition	-	0.9148	91.48%
CYP1A2 inhibition	-	0.7201	72.01%
CYP2C8 inhibition	+	0.6482	64.82%
CYP inhibitory promiscuity	+	0.6975	69.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6621	66.21%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.7650	76.50%
Skin irritation	-	0.7930	79.30%
Skin corrosion	-	0.9707	97.07%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6692	66.92%
Micronuclear	+	0.6759	67.59%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8971	89.71%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7835	78.35%
Acute Oral Toxicity (c)	III	0.7303	73.03%
Estrogen receptor binding	+	0.8733	87.33%
Androgen receptor binding	+	0.8751	87.51%
Thyroid receptor binding	+	0.5722	57.22%
Glucocorticoid receptor binding	+	0.8214	82.14%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.8074	80.74%
Honey bee toxicity	-	0.7265	72.65%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	-	0.4611	46.11%

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	99.63%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.29%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.13%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.34%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.16%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.23%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.37%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.69%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.09%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.01%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.98%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.89%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.36%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	81.02%	83.82%

Plants that contains it

• Scutellaria prostrata

Cross-Links

• PubChem: 4539166
• LOTUS: LTS0111000
• wikiData: Q104993919