2-(3-Hydroxy-5-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one

Details

• Internal ID: 863d7281-2d23-4ae1-83d4-5235a0d0add9
• Taxonomy: Lignans, neolignans and related compounds > Coumarinolignans
• IUPAC Name: 2-(3-hydroxy-5-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
• InChI: InChI=1S/C20H18O8/c1-24-13-6-11(5-12(22)8-13)17-15(9-21)26-19-14(25-2)7-10-3-4-16(23)27-18(10)20(19)28-17/h3-8,15,17,21-22H,9H2,1-2H3
• InChI Key: DAQYGJQQKJBBJA-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₈
• Molecular Weight: 386.40 g/mol
• Exact Mass: 386.10016753 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9150	91.50%
Caco-2	-	0.6390	63.90%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8090	80.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8509	85.09%
OATP1B3 inhibitior	-	0.2712	27.12%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6077	60.77%
P-glycoprotein inhibitior	+	0.7966	79.66%
P-glycoprotein substrate	-	0.8196	81.96%
CYP3A4 substrate	+	0.5323	53.23%
CYP2C9 substrate	-	0.8212	82.12%
CYP2D6 substrate	-	0.8135	81.35%
CYP3A4 inhibition	-	0.8224	82.24%
CYP2C9 inhibition	-	0.5672	56.72%
CYP2C19 inhibition	-	0.7656	76.56%
CYP2D6 inhibition	-	0.9056	90.56%
CYP1A2 inhibition	-	0.9197	91.97%
CYP2C8 inhibition	+	0.5409	54.09%
CYP inhibitory promiscuity	+	0.5722	57.22%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6925	69.25%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.8487	84.87%
Skin irritation	-	0.8335	83.35%
Skin corrosion	-	0.9739	97.39%
Ames mutagenesis	-	0.5807	58.07%
Human Ether-a-go-go-Related Gene inhibition	-	0.4723	47.23%
Micronuclear	+	0.7133	71.33%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.9143	91.43%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.4601	46.01%
Acute Oral Toxicity (c)	III	0.6661	66.61%
Estrogen receptor binding	+	0.7233	72.33%
Androgen receptor binding	+	0.7929	79.29%
Thyroid receptor binding	-	0.5567	55.67%
Glucocorticoid receptor binding	+	0.7462	74.62%
Aromatase binding	-	0.5629	56.29%
PPAR gamma	+	0.5732	57.32%
Honey bee toxicity	-	0.8099	80.99%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5749	57.49%
Fish aquatic toxicity	+	0.7289	72.89%

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	98.19%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.45%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.42%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.47%	86.92%
CHEMBL2581	P07339	Cathepsin D	90.60%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.64%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.39%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.47%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.70%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.08%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	84.87%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.35%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.09%	92.62%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.53%	97.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.11%	85.14%

Plants that contains it

• Hemidesmus indicus

Cross-Links

• PubChem: 15931469
• LOTUS: LTS0056261
• wikiData: Q104973875