(+)-2,3-Dihydro-2-(1-hydroxy-1-methylethyl)-5,6-dimethoxy-9H-pyrano[2,3-f]-1,4-benzodioxin-9-one

Details

• Internal ID: 3772d562-8a0c-4682-af49-59da9a3c29c5
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > p-Dioxolo[2,3-h]coumarins
• IUPAC Name: 2-(2-hydroxypropan-2-yl)-5,6-dimethoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
• SMILES (Canonical): CC(C)(C1COC2=C(O1)C3=C(C=CC(=O)O3)C(=C2OC)OC)O
• SMILES (Isomeric): CC(C)(C1COC2=C(O1)C3=C(C=CC(=O)O3)C(=C2OC)OC)O
• InChI: InChI=1S/C16H18O7/c1-16(2,18)9-7-21-14-13(20-4)11(19-3)8-5-6-10(17)23-12(8)15(14)22-9/h5-6,9,18H,7H2,1-4H3
• InChI Key: CWLINRWSQJGKGK-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₈O₇
• Molecular Weight: 322.31 g/mol
• Exact Mass: 322.10525291 g/mol
• Topological Polar Surface Area (TPSA): 83.40 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.72
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• (+)-2,3-Dihydro-2-(1-hydroxy-1-methylethyl)-5,6-dimethoxy-9H-pyrano[2,3-f]-1,4-benzodioxin-9-one
• 137809-98-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9766	97.66%
Caco-2	+	0.6539	65.39%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7604	76.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9383	93.83%
OATP1B3 inhibitior	+	0.9327	93.27%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5659	56.59%
P-glycoprotein inhibitior	-	0.6009	60.09%
P-glycoprotein substrate	-	0.7999	79.99%
CYP3A4 substrate	+	0.5140	51.40%
CYP2C9 substrate	-	0.6882	68.82%
CYP2D6 substrate	-	0.8350	83.50%
CYP3A4 inhibition	-	0.8151	81.51%
CYP2C9 inhibition	-	0.9028	90.28%
CYP2C19 inhibition	-	0.7219	72.19%
CYP2D6 inhibition	-	0.8502	85.02%
CYP1A2 inhibition	+	0.5547	55.47%
CYP2C8 inhibition	-	0.8115	81.15%
CYP inhibitory promiscuity	-	0.9166	91.66%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6259	62.59%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.5000	50.00%
Skin irritation	-	0.8117	81.17%
Skin corrosion	-	0.9649	96.49%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4520	45.20%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8545	85.45%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8569	85.69%
Acute Oral Toxicity (c)	III	0.7157	71.57%
Estrogen receptor binding	+	0.9114	91.14%
Androgen receptor binding	+	0.5547	55.47%
Thyroid receptor binding	+	0.5219	52.19%
Glucocorticoid receptor binding	+	0.6398	63.98%
Aromatase binding	+	0.6175	61.75%
PPAR gamma	+	0.8299	82.99%
Honey bee toxicity	-	0.8600	86.00%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9225	92.25%

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	97.56%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.61%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.19%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.75%	99.23%
CHEMBL2581	P07339	Cathepsin D	86.67%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.64%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.59%	94.00%
CHEMBL1871	P10275	Androgen Receptor	83.95%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.70%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.10%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.06%	97.09%

Plants that contains it

• Pterocaulon purpurascens

Cross-Links

• PubChem: 15689635
• LOTUS: LTS0113501
• wikiData: Q104971344