2-[(2S)-6-acetyl-5-hydroxy-2,3-dihydro-1-benzofuran-2-yl]prop-2-enal

Details

• Internal ID: 963eb65e-89e0-4447-955a-70f783a02cf5
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Acetophenones
• IUPAC Name: 2-[(2S)-6-acetyl-5-hydroxy-2,3-dihydro-1-benzofuran-2-yl]prop-2-enal
• SMILES (Canonical): CC(=O)C1=C(C=C2CC(OC2=C1)C(=C)C=O)O
• SMILES (Isomeric): CC(=O)C1=C(C=C2C[C@H](OC2=C1)C(=C)C=O)O
• InChI: InChI=1S/C13H12O4/c1-7(6-14)12-4-9-3-11(16)10(8(2)15)5-13(9)17-12/h3,5-6,12,16H,1,4H2,2H3/t12-/m0/s1
• InChI Key: XTLZYQWMGSURNJ-LBPRGKRZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₂O₄
• Molecular Weight: 232.23 g/mol
• Exact Mass: 232.07355886 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.65
• 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	+	0.9936	99.36%
Caco-2	+	0.5269	52.69%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7761	77.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9144	91.44%
OATP1B3 inhibitior	+	0.9801	98.01%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7967	79.67%
P-glycoprotein inhibitior	-	0.9437	94.37%
P-glycoprotein substrate	-	0.8421	84.21%
CYP3A4 substrate	-	0.5364	53.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8210	82.10%
CYP3A4 inhibition	-	0.8463	84.63%
CYP2C9 inhibition	+	0.7097	70.97%
CYP2C19 inhibition	+	0.5372	53.72%
CYP2D6 inhibition	-	0.9304	93.04%
CYP1A2 inhibition	+	0.8202	82.02%
CYP2C8 inhibition	-	0.8340	83.40%
CYP inhibitory promiscuity	+	0.5674	56.74%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9168	91.68%
Carcinogenicity (trinary)	Non-required	0.4593	45.93%
Eye corrosion	-	0.9500	95.00%
Eye irritation	+	0.8483	84.83%
Skin irritation	-	0.5408	54.08%
Skin corrosion	-	0.8970	89.70%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4556	45.56%
Micronuclear	+	0.7159	71.59%
Hepatotoxicity	-	0.5697	56.97%
skin sensitisation	-	0.5281	52.81%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.5882	58.82%
Acute Oral Toxicity (c)	II	0.4234	42.34%
Estrogen receptor binding	-	0.8076	80.76%
Androgen receptor binding	-	0.7870	78.70%
Thyroid receptor binding	-	0.7182	71.82%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5720	57.20%
PPAR gamma	-	0.6534	65.34%
Honey bee toxicity	-	0.8736	87.36%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9770	97.70%

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	98.32%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.86%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	87.02%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	86.90%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.47%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.02%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	83.66%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.40%	99.17%
CHEMBL217	P14416	Dopamine D2 receptor	82.18%	95.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.76%	100.00%

Plants that contains it

• Baccharis alaternoides
• Baccharis conferta
• Baccharis reticularia
• Baccharis retusa

Cross-Links

• PubChem: 163034065
• LOTUS: LTS0205332
• wikiData: Q105341659