Methyl 2-isopropenyl-2,3-dihydrobenzofuran-5-carboxylate

Details

• Internal ID: 146c74bf-92d4-4eec-a7c4-900e82a21ad9
• Taxonomy: Organoheterocyclic compounds > Coumarans
• IUPAC Name: methyl 2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-carboxylate
• SMILES (Canonical): CC(=C)C1CC2=C(O1)C=CC(=C2)C(=O)OC
• SMILES (Isomeric): CC(=C)C1CC2=C(O1)C=CC(=C2)C(=O)OC
• InChI: InChI=1S/C13H14O3/c1-8(2)12-7-10-6-9(13(14)15-3)4-5-11(10)16-12/h4-6,12H,1,7H2,2-3H3
• InChI Key: AMYPKJBHUVIYPY-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₄O₃
• Molecular Weight: 218.25 g/mol
• Exact Mass: 218.094294304 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.35
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 5-Benzofurancarboxylic acid, 2,3-dihydro-2-(1-methylethenyl)-, methyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.6556	65.56%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6057	60.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9100	91.00%
OATP1B3 inhibitior	+	0.9488	94.88%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7404	74.04%
P-glycoprotein inhibitior	-	0.9606	96.06%
P-glycoprotein substrate	-	0.8440	84.40%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7613	76.13%
CYP3A4 inhibition	-	0.5865	58.65%
CYP2C9 inhibition	-	0.7387	73.87%
CYP2C19 inhibition	+	0.5550	55.50%
CYP2D6 inhibition	-	0.9055	90.55%
CYP1A2 inhibition	+	0.8109	81.09%
CYP2C8 inhibition	-	0.7320	73.20%
CYP inhibitory promiscuity	+	0.7618	76.18%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8019	80.19%
Carcinogenicity (trinary)	Non-required	0.5959	59.59%
Eye corrosion	-	0.8977	89.77%
Eye irritation	+	0.7791	77.91%
Skin irritation	-	0.6644	66.44%
Skin corrosion	-	0.9741	97.41%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6459	64.59%
Micronuclear	-	0.6041	60.41%
Hepatotoxicity	-	0.5163	51.63%
skin sensitisation	+	0.6481	64.81%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	+	0.4890	48.90%
Acute Oral Toxicity (c)	III	0.5695	56.95%
Estrogen receptor binding	-	0.8690	86.90%
Androgen receptor binding	-	0.7871	78.71%
Thyroid receptor binding	-	0.7836	78.36%
Glucocorticoid receptor binding	-	0.8325	83.25%
Aromatase binding	-	0.6099	60.99%
PPAR gamma	-	0.8530	85.30%
Honey bee toxicity	-	0.8355	83.55%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9816	98.16%

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	95.94%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.09%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.28%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.01%	99.17%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.15%	94.80%
CHEMBL340	P08684	Cytochrome P450 3A4	85.92%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.73%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.70%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.48%	95.89%
CHEMBL4208	P20618	Proteasome component C5	83.17%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.78%	95.89%
CHEMBL2581	P07339	Cathepsin D	81.72%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	80.73%	94.73%

Plants that contains it

• Gentiana algida

Cross-Links

• PubChem: 5316729
• LOTUS: LTS0139643
• wikiData: Q104915024