1-[(2R,3S)-6-hydroxy-3-methoxy-2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl]ethanone

Details

• Internal ID: 5fa410fe-516b-4ef7-994d-482e9e9809a1
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Acetophenones
• IUPAC Name: 1-[(2R,3S)-6-hydroxy-3-methoxy-2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl]ethanone
• SMILES (Canonical): CC(=C)C1C(C2=CC(=C(C=C2O1)O)C(=O)C)OC
• SMILES (Isomeric): CC(=C)[C@@H]1[C@H](C2=CC(=C(C=C2O1)O)C(=O)C)OC
• InChI: InChI=1S/C14H16O4/c1-7(2)13-14(17-4)10-5-9(8(3)15)11(16)6-12(10)18-13/h5-6,13-14,16H,1H2,2-4H3/t13-,14+/m1/s1
• InChI Key: PHYSEYYYFQMJGP-KGLIPLIRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₆O₄
• Molecular Weight: 248.27 g/mol
• Exact Mass: 248.10485899 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.6916	69.16%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6393	63.93%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9200	92.00%
OATP1B3 inhibitior	+	0.9638	96.38%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9094	90.94%
P-glycoprotein inhibitior	-	0.8563	85.63%
P-glycoprotein substrate	-	0.8559	85.59%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8251	82.51%
CYP3A4 inhibition	+	0.6093	60.93%
CYP2C9 inhibition	-	0.8464	84.64%
CYP2C19 inhibition	+	0.7716	77.16%
CYP2D6 inhibition	-	0.9328	93.28%
CYP1A2 inhibition	+	0.8497	84.97%
CYP2C8 inhibition	-	0.6378	63.78%
CYP inhibitory promiscuity	+	0.7851	78.51%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4929	49.29%
Eye corrosion	-	0.9426	94.26%
Eye irritation	+	0.8748	87.48%
Skin irritation	-	0.6635	66.35%
Skin corrosion	-	0.9690	96.90%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.7059	70.59%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.6425	64.25%
Respiratory toxicity	-	0.7889	78.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5076	50.76%
Acute Oral Toxicity (c)	II	0.6492	64.92%
Estrogen receptor binding	-	0.7090	70.90%
Androgen receptor binding	-	0.6942	69.42%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.8094	80.94%
Aromatase binding	-	0.5623	56.23%
PPAR gamma	+	0.5515	55.15%
Honey bee toxicity	-	0.7122	71.22%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9695	96.95%

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	98.35%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.68%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.61%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	88.47%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	86.37%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.66%	99.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.50%	91.07%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.45%	94.45%

Plants that contains it

• Lasiolaena morii
• Ligularia veitchiana
• Stomatanthes corumbensis

Cross-Links

• PubChem: 5324647
• LOTUS: LTS0092454
• wikiData: Q105209321