1-[(2R)-4-hydroxy-2-(3-hydroxyprop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethanone

Details

• Internal ID: f853eb93-966a-45f4-8b3c-8faaf455f23e
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Acetophenones
• IUPAC Name: 1-[(2R)-4-hydroxy-2-(3-hydroxyprop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethanone
• SMILES (Canonical): CC(=O)C1=C(C2=C(C=C1)OC(C2)C(=C)CO)O
• SMILES (Isomeric): CC(=O)C1=C(C2=C(C=C1)O[C@H](C2)C(=C)CO)O
• InChI: InChI=1S/C13H14O4/c1-7(6-14)12-5-10-11(17-12)4-3-9(8(2)15)13(10)16/h3-4,12,14,16H,1,5-6H2,2H3/t12-/m1/s1
• InChI Key: TXCCGIYIORQRRJ-GFCCVEGCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.25 g/mol
• Exact Mass: 234.08920892 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.45
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9925	99.25%
Caco-2	-	0.5267	52.67%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8146	81.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9059	90.59%
OATP1B3 inhibitior	+	0.9755	97.55%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8174	81.74%
P-glycoprotein inhibitior	-	0.9598	95.98%
P-glycoprotein substrate	-	0.8029	80.29%
CYP3A4 substrate	-	0.5363	53.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8058	80.58%
CYP3A4 inhibition	-	0.7960	79.60%
CYP2C9 inhibition	-	0.6106	61.06%
CYP2C19 inhibition	+	0.5276	52.76%
CYP2D6 inhibition	-	0.9042	90.42%
CYP1A2 inhibition	+	0.6815	68.15%
CYP2C8 inhibition	-	0.7935	79.35%
CYP inhibitory promiscuity	+	0.7374	73.74%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6079	60.79%
Eye corrosion	-	0.9800	98.00%
Eye irritation	-	0.5153	51.53%
Skin irritation	-	0.7254	72.54%
Skin corrosion	-	0.9333	93.33%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6524	65.24%
Micronuclear	-	0.5341	53.41%
Hepatotoxicity	-	0.5017	50.17%
skin sensitisation	-	0.6230	62.30%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6135	61.35%
Acute Oral Toxicity (c)	III	0.4612	46.12%
Estrogen receptor binding	-	0.8165	81.65%
Androgen receptor binding	-	0.5514	55.14%
Thyroid receptor binding	-	0.5623	56.23%
Glucocorticoid receptor binding	-	0.6506	65.06%
Aromatase binding	-	0.5352	53.52%
PPAR gamma	+	0.5345	53.45%
Honey bee toxicity	-	0.8912	89.12%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9744	97.44%

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	97.78%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.90%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.80%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.22%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	84.97%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.05%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.65%	94.80%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.21%	85.14%

Plants that contains it

• Osteospermum imbricatum

Cross-Links

• PubChem: 162888129
• LOTUS: LTS0012584
• wikiData: Q105266369