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

Details

• Internal ID: 2b524865-4acf-4088-ba2d-48e94623c268
• Taxonomy: Lignans, neolignans and related compounds > Coumarinolignans
• IUPAC Name: (2R,3R)-3-(3,4-dimethoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2C(OC3=C4C(=CC(=C3O2)OC)C=CC(=O)O4)CO)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)[C@@H]2[C@H](OC3=C4C(=CC(=C3O2)OC)C=CC(=O)O4)CO)OC
• InChI: InChI=1S/C21H20O8/c1-24-13-6-4-11(8-14(13)25-2)18-16(10-22)27-21-19-12(5-7-17(23)28-19)9-15(26-3)20(21)29-18/h4-9,16,18,22H,10H2,1-3H3/t16-,18-/m1/s1
• InChI Key: YJINBIPHZOTKQM-SJLPKXTDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₈
• Molecular Weight: 400.40 g/mol
• Exact Mass: 400.11581759 g/mol
• Topological Polar Surface Area (TPSA): 92.70 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.69
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9460	94.60%
Caco-2	+	0.6716	67.16%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7797	77.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8866	88.66%
OATP1B3 inhibitior	+	0.7928	79.28%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9420	94.20%
P-glycoprotein inhibitior	+	0.8788	87.88%
P-glycoprotein substrate	-	0.8349	83.49%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8464	84.64%
CYP2D6 substrate	-	0.8131	81.31%
CYP3A4 inhibition	-	0.8414	84.14%
CYP2C9 inhibition	-	0.8356	83.56%
CYP2C19 inhibition	-	0.8496	84.96%
CYP2D6 inhibition	-	0.9445	94.45%
CYP1A2 inhibition	-	0.9244	92.44%
CYP2C8 inhibition	-	0.6569	65.69%
CYP inhibitory promiscuity	-	0.5415	54.15%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6497	64.97%
Eye corrosion	-	0.9844	98.44%
Eye irritation	-	0.8613	86.13%
Skin irritation	-	0.8390	83.90%
Skin corrosion	-	0.9804	98.04%
Ames mutagenesis	-	0.6270	62.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6829	68.29%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.9061	90.61%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.6718	67.18%
Acute Oral Toxicity (c)	III	0.4776	47.76%
Estrogen receptor binding	+	0.8792	87.92%
Androgen receptor binding	+	0.8383	83.83%
Thyroid receptor binding	+	0.5673	56.73%
Glucocorticoid receptor binding	+	0.8715	87.15%
Aromatase binding	-	0.6031	60.31%
PPAR gamma	+	0.6742	67.42%
Honey bee toxicity	-	0.8334	83.34%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.7229	72.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.35%	85.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.33%	86.92%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.92%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.35%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.56%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.70%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.25%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.46%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.37%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.36%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.32%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.04%	86.33%

Plants that contains it

• Hyoscyamus niger

Cross-Links

• PubChem: 162895008
• LOTUS: LTS0229519
• wikiData: Q105349287