Methyl 2-(4-hydroxyphenyl)-3-methyl-2,3-dihydro-1-benzofuran-5-carboxylate

Details

• Internal ID: 0510b781-6dba-4f9c-9522-89cb5f2883ca
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: methyl 2-(4-hydroxyphenyl)-3-methyl-2,3-dihydro-1-benzofuran-5-carboxylate
• SMILES (Canonical): CC1C(OC2=C1C=C(C=C2)C(=O)OC)C3=CC=C(C=C3)O
• SMILES (Isomeric): CC1C(OC2=C1C=C(C=C2)C(=O)OC)C3=CC=C(C=C3)O
• InChI: InChI=1S/C17H16O4/c1-10-14-9-12(17(19)20-2)5-8-15(14)21-16(10)11-3-6-13(18)7-4-11/h3-10,16,18H,1-2H3
• InChI Key: NRPSKMYNCNOUPB-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.31 g/mol
• Exact Mass: 284.10485899 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.42
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9947	99.47%
Caco-2	+	0.7554	75.54%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7841	78.41%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.6975	69.75%
OATP1B3 inhibitior	+	0.9035	90.35%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6958	69.58%
P-glycoprotein inhibitior	-	0.7829	78.29%
P-glycoprotein substrate	-	0.8500	85.00%
CYP3A4 substrate	+	0.5632	56.32%
CYP2C9 substrate	-	0.7980	79.80%
CYP2D6 substrate	-	0.7912	79.12%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	+	0.9567	95.67%
CYP2C19 inhibition	+	0.7593	75.93%
CYP2D6 inhibition	-	0.7630	76.30%
CYP1A2 inhibition	+	0.8663	86.63%
CYP2C8 inhibition	+	0.8195	81.95%
CYP inhibitory promiscuity	+	0.7667	76.67%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8810	88.10%
Carcinogenicity (trinary)	Warning	0.3457	34.57%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.8223	82.23%
Skin irritation	-	0.7474	74.74%
Skin corrosion	-	0.9854	98.54%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4242	42.42%
Micronuclear	+	0.8659	86.59%
Hepatotoxicity	-	0.6631	66.31%
skin sensitisation	-	0.9435	94.35%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.5512	55.12%
Acute Oral Toxicity (c)	III	0.4491	44.91%
Estrogen receptor binding	+	0.5638	56.38%
Androgen receptor binding	+	0.5440	54.40%
Thyroid receptor binding	+	0.5492	54.92%
Glucocorticoid receptor binding	-	0.5951	59.51%
Aromatase binding	+	0.5374	53.74%
PPAR gamma	+	0.5236	52.36%
Honey bee toxicity	-	0.9034	90.34%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9842	98.42%

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	97.61%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.07%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.09%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	88.53%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.35%	96.09%
CHEMBL2535	P11166	Glucose transporter	86.73%	98.75%
CHEMBL2581	P07339	Cathepsin D	86.56%	98.95%
CHEMBL4208	P20618	Proteasome component C5	85.35%	90.00%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	83.97%	95.55%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.39%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	83.33%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	82.12%	91.19%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.57%	94.80%

Plants that contains it

• Piper regnellii

Cross-Links

• PubChem: 163002179
• LOTUS: LTS0112009
• wikiData: Q105184758