[9-[(Z)-but-2-enyl]-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] acetate

Details

• Internal ID: 1c3738d8-d615-4e02-a438-f469e860d14b
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: [9-[(Z)-but-2-enyl]-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] acetate
• SMILES (Canonical): CC=CCC1C(C2=C(C=CC3=C2OC(=O)C=C3)OC1(C)C)OC(=O)C
• SMILES (Isomeric): C/C=C\CC1C(C2=C(C=CC3=C2OC(=O)C=C3)OC1(C)C)OC(=O)C
• InChI: InChI=1S/C20H22O5/c1-5-6-7-14-19(23-12(2)21)17-15(25-20(14,3)4)10-8-13-9-11-16(22)24-18(13)17/h5-6,8-11,14,19H,7H2,1-4H3/b6-5-
• InChI Key: LTSBAPIBOQOBOR-WAYWQWQTSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₅
• Molecular Weight: 342.40 g/mol
• Exact Mass: 342.14672380 g/mol
• Topological Polar Surface Area (TPSA): 61.80 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.15
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9899	98.99%
Caco-2	+	0.6541	65.41%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6782	67.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8924	89.24%
OATP1B3 inhibitior	+	0.9261	92.61%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7225	72.25%
P-glycoprotein inhibitior	+	0.6924	69.24%
P-glycoprotein substrate	-	0.7658	76.58%
CYP3A4 substrate	+	0.5778	57.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8560	85.60%
CYP3A4 inhibition	-	0.6482	64.82%
CYP2C9 inhibition	-	0.6997	69.97%
CYP2C19 inhibition	-	0.6522	65.22%
CYP2D6 inhibition	-	0.9210	92.10%
CYP1A2 inhibition	-	0.6133	61.33%
CYP2C8 inhibition	-	0.5943	59.43%
CYP inhibitory promiscuity	+	0.5483	54.83%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.5206	52.06%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.9379	93.79%
Skin irritation	-	0.7771	77.71%
Skin corrosion	-	0.9501	95.01%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8936	89.36%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.5572	55.72%
skin sensitisation	-	0.7783	77.83%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6714	67.14%
Estrogen receptor binding	+	0.8284	82.84%
Androgen receptor binding	+	0.7240	72.40%
Thyroid receptor binding	-	0.5423	54.23%
Glucocorticoid receptor binding	+	0.7186	71.86%
Aromatase binding	+	0.5254	52.54%
PPAR gamma	+	0.6727	67.27%
Honey bee toxicity	-	0.7862	78.62%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9972	99.72%

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	98.20%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.34%	83.82%
CHEMBL2581	P07339	Cathepsin D	95.24%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.74%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.45%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.36%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.23%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.59%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.99%	86.33%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.89%	90.24%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.78%	85.30%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.67%	96.95%

Plants that contains it

• Kitagawia praeruptora
• Panax quinquefolius
• Peucedanum japonicum

Cross-Links

• PubChem: 5320690
• NPASS: NPC126615
• LOTUS: LTS0166225
• wikiData: Q105157134