2-[(2R,3S)-5-acetyl-3-acetyloxy-2,3-dihydro-1-benzofuran-2-yl]prop-2-enyl acetate

Details

• Internal ID: 286b48dc-80a8-46e1-97bd-b17dcaac7d7c
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Acetophenones
• IUPAC Name: 2-[(2R,3S)-5-acetyl-3-acetyloxy-2,3-dihydro-1-benzofuran-2-yl]prop-2-enyl acetate
• SMILES (Canonical): CC(=O)C1=CC2=C(C=C1)OC(C2OC(=O)C)C(=C)COC(=O)C
• SMILES (Isomeric): CC(=O)C1=CC2=C(C=C1)O[C@@H]([C@H]2OC(=O)C)C(=C)COC(=O)C
• InChI: InChI=1S/C17H18O6/c1-9(8-21-11(3)19)16-17(22-12(4)20)14-7-13(10(2)18)5-6-15(14)23-16/h5-7,16-17H,1,8H2,2-4H3/t16-,17+/m1/s1
• InChI Key: STNMHRXLVQEUHH-SJORKVTESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₆
• Molecular Weight: 318.32 g/mol
• Exact Mass: 318.11033829 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9955	99.55%
Caco-2	+	0.6211	62.11%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6964	69.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9061	90.61%
OATP1B3 inhibitior	+	0.9188	91.88%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.4917	49.17%
P-glycoprotein inhibitior	-	0.5051	50.51%
P-glycoprotein substrate	-	0.8018	80.18%
CYP3A4 substrate	+	0.5155	51.55%
CYP2C9 substrate	-	0.6039	60.39%
CYP2D6 substrate	-	0.8373	83.73%
CYP3A4 inhibition	-	0.5458	54.58%
CYP2C9 inhibition	+	0.5840	58.40%
CYP2C19 inhibition	+	0.8031	80.31%
CYP2D6 inhibition	-	0.9328	93.28%
CYP1A2 inhibition	+	0.9181	91.81%
CYP2C8 inhibition	+	0.7068	70.68%
CYP inhibitory promiscuity	+	0.7932	79.32%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6488	64.88%
Eye corrosion	-	0.9690	96.90%
Eye irritation	-	0.5629	56.29%
Skin irritation	-	0.7175	71.75%
Skin corrosion	-	0.9523	95.23%
Ames mutagenesis	-	0.6247	62.47%
Human Ether-a-go-go-Related Gene inhibition	-	0.4877	48.77%
Micronuclear	-	0.5308	53.08%
Hepatotoxicity	+	0.5281	52.81%
skin sensitisation	+	0.5124	51.24%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5122	51.22%
Acute Oral Toxicity (c)	III	0.4915	49.15%
Estrogen receptor binding	+	0.5295	52.95%
Androgen receptor binding	-	0.5598	55.98%
Thyroid receptor binding	-	0.5908	59.08%
Glucocorticoid receptor binding	+	0.5423	54.23%
Aromatase binding	-	0.6513	65.13%
PPAR gamma	-	0.7566	75.66%
Honey bee toxicity	-	0.8563	85.63%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6802	68.02%
Fish aquatic toxicity	+	0.9974	99.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.75%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.47%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.42%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.09%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	88.54%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	87.91%	91.19%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.25%	94.80%
CHEMBL4040	P28482	MAP kinase ERK2	84.83%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.59%	97.25%
CHEMBL2581	P07339	Cathepsin D	83.36%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	83.07%	91.49%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.36%	97.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.63%	89.00%

Plants that contains it

• Ophryosporus charua

Cross-Links

• PubChem: 163041989
• LOTUS: LTS0002827
• wikiData: Q105260438