5-Acetyl-6-hydroxy-2-isopropenyl-2,3-dihydrobenzofuran

Details

• Internal ID: e068f62a-6088-42d4-ad3d-bdfa9a1af73c
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Acetophenones
• IUPAC Name: 1-(6-hydroxy-2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl)ethanone
• SMILES (Canonical): CC(=C)C1CC2=CC(=C(C=C2O1)O)C(=O)C
• SMILES (Isomeric): CC(=C)C1CC2=CC(=C(C=C2O1)O)C(=O)C
• InChI: InChI=1S/C13H14O3/c1-7(2)12-5-9-4-10(8(3)14)11(15)6-13(9)16-12/h4,6,12,15H,1,5H2,2-3H3
• InChI Key: FHJSLVLVJPGFRY-UHFFFAOYSA-N
• Popularity: 3 references 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): 46.50 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.47
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 5-Acetyl-6-hydroxy-2-isopropenyl-2,3-dihydrobenzofuran
• MEGxp0_001564
• SCHEMBL17728865
• DTXSID301158928
• 1-(6-hydroxy-2-isopropenyl-2,3-dihydrobenzofuran-5-yl)ethanone
• 1-[2,3-Dihydro-6-hydroxy-2-(1-methylethenyl)-5-benzofuranyl]ethanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.6801	68.01%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6862	68.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9357	93.57%
OATP1B3 inhibitior	+	0.9754	97.54%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8820	88.20%
P-glycoprotein inhibitior	-	0.9488	94.88%
P-glycoprotein substrate	-	0.8639	86.39%
CYP3A4 substrate	-	0.5706	57.06%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.7912	79.12%
CYP3A4 inhibition	-	0.6538	65.38%
CYP2C9 inhibition	-	0.7484	74.84%
CYP2C19 inhibition	+	0.5990	59.90%
CYP2D6 inhibition	-	0.9387	93.87%
CYP1A2 inhibition	+	0.9154	91.54%
CYP2C8 inhibition	-	0.9330	93.30%
CYP inhibitory promiscuity	+	0.6643	66.43%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5584	55.84%
Eye corrosion	-	0.9393	93.93%
Eye irritation	+	0.8872	88.72%
Skin irritation	+	0.4912	49.12%
Skin corrosion	-	0.9217	92.17%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5217	52.17%
Micronuclear	+	0.5418	54.18%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	+	0.6627	66.27%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.5565	55.65%
Acute Oral Toxicity (c)	III	0.4959	49.59%
Estrogen receptor binding	-	0.8950	89.50%
Androgen receptor binding	-	0.8353	83.53%
Thyroid receptor binding	-	0.6847	68.47%
Glucocorticoid receptor binding	-	0.8195	81.95%
Aromatase binding	-	0.5589	55.89%
PPAR gamma	-	0.5788	57.88%
Honey bee toxicity	-	0.8595	85.95%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9814	98.14%

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	97.51%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.26%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	91.46%	91.49%
CHEMBL217	P14416	Dopamine D2 receptor	89.87%	95.62%
CHEMBL340	P08684	Cytochrome P450 3A4	86.36%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	84.25%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.37%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.90%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.71%	92.94%
CHEMBL2581	P07339	Cathepsin D	81.63%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.72%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.01%	85.14%

Plants that contains it

• Ligularia stenocephala
• Solanum dulcamara

Cross-Links

• PubChem: 455702
• NPASS: NPC253924