(9-Hydroxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl) 3-methylbutanoate

Details

• Internal ID: 9f3c7260-571b-4791-8fd7-59eb58fe78dc
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: (9-hydroxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl) 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OC1C(C(OC2=C1C3=C(C=C2)C=CC(=O)O3)(C)C)O
• SMILES (Isomeric): CC(C)CC(=O)OC1C(C(OC2=C1C3=C(C=C2)C=CC(=O)O3)(C)C)O
• InChI: InChI=1S/C19H22O6/c1-10(2)9-14(21)24-17-15-12(25-19(3,4)18(17)22)7-5-11-6-8-13(20)23-16(11)15/h5-8,10,17-18,22H,9H2,1-4H3
• InChI Key: IQVBHJMBBBNYAR-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.40 g/mol
• Exact Mass: 346.14163842 g/mol
• Topological Polar Surface Area (TPSA): 82.10 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.96
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 4'-O-Isovaleryl-trans-khellactone
• (9-hydroxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl) 3-methylbutanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9425	94.25%
Caco-2	+	0.6409	64.09%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7551	75.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9166	91.66%
OATP1B3 inhibitior	+	0.8882	88.82%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.4635	46.35%
P-glycoprotein inhibitior	+	0.5837	58.37%
P-glycoprotein substrate	-	0.7363	73.63%
CYP3A4 substrate	+	0.5490	54.90%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8245	82.45%
CYP3A4 inhibition	-	0.8355	83.55%
CYP2C9 inhibition	-	0.7969	79.69%
CYP2C19 inhibition	-	0.8905	89.05%
CYP2D6 inhibition	-	0.9158	91.58%
CYP1A2 inhibition	-	0.7787	77.87%
CYP2C8 inhibition	-	0.7410	74.10%
CYP inhibitory promiscuity	-	0.9084	90.84%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5483	54.83%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9466	94.66%
Skin irritation	-	0.8247	82.47%
Skin corrosion	-	0.9503	95.03%
Ames mutagenesis	-	0.5228	52.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.6609	66.09%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8354	83.54%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6930	69.30%
Estrogen receptor binding	+	0.5818	58.18%
Androgen receptor binding	+	0.6716	67.16%
Thyroid receptor binding	+	0.5339	53.39%
Glucocorticoid receptor binding	+	0.7100	71.00%
Aromatase binding	-	0.5745	57.45%
PPAR gamma	-	0.5183	51.83%
Honey bee toxicity	-	0.8315	83.15%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9745	97.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.67%	83.82%
CHEMBL2581	P07339	Cathepsin D	97.68%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.20%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.76%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.53%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.80%	99.23%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.27%	95.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.94%	96.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.18%	94.00%

Plants that contains it

• Musineon divaricatum

Cross-Links

• PubChem: 455908
• LOTUS: LTS0060370
• wikiData: Q105118616