1-[5-Hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethan-1-one

Details

• Internal ID: b81cc642-c053-49fa-b062-9d219be66bb4
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: 1-(5-hydroxy-2-prop-1-en-2-yl-1-benzofuran-6-yl)ethanone
• SMILES (Canonical): CC(=C)C1=CC2=CC(=C(C=C2O1)C(=O)C)O
• SMILES (Isomeric): CC(=C)C1=CC2=CC(=C(C=C2O1)C(=O)C)O
• InChI: InChI=1S/C13H12O3/c1-7(2)12-5-9-4-11(15)10(8(3)14)6-13(9)16-12/h4-6,15H,1H2,2-3H3
• InChI Key: WCOLFOJRDDQQEN-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₂O₃
• Molecular Weight: 216.23 g/mol
• Exact Mass: 216.078644241 g/mol
• Topological Polar Surface Area (TPSA): 50.40 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.37
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 1-(5-Hydroxy-2-(prop-1-en-2-yl)benzofuran-6-yl)ethanone
• Deacetoxyageratone
• DTXSID40764654
• 1-[5-Hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethan-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7866	78.66%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7186	71.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9222	92.22%
OATP1B3 inhibitior	+	0.9751	97.51%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8132	81.32%
P-glycoprotein inhibitior	-	0.8598	85.98%
P-glycoprotein substrate	-	0.8264	82.64%
CYP3A4 substrate	-	0.6241	62.41%
CYP2C9 substrate	-	0.6015	60.15%
CYP2D6 substrate	-	0.8577	85.77%
CYP3A4 inhibition	-	0.5892	58.92%
CYP2C9 inhibition	-	0.6310	63.10%
CYP2C19 inhibition	+	0.6583	65.83%
CYP2D6 inhibition	-	0.9435	94.35%
CYP1A2 inhibition	+	0.9400	94.00%
CYP2C8 inhibition	-	0.8348	83.48%
CYP inhibitory promiscuity	+	0.8140	81.40%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5165	51.65%
Eye corrosion	-	0.9478	94.78%
Eye irritation	+	0.8550	85.50%
Skin irritation	-	0.5271	52.71%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7512	75.12%
Micronuclear	+	0.8459	84.59%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	+	0.6028	60.28%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6609	66.09%
Acute Oral Toxicity (c)	III	0.5191	51.91%
Estrogen receptor binding	+	0.6612	66.12%
Androgen receptor binding	-	0.6161	61.61%
Thyroid receptor binding	-	0.6279	62.79%
Glucocorticoid receptor binding	-	0.5372	53.72%
Aromatase binding	+	0.6436	64.36%
PPAR gamma	+	0.6544	65.44%
Honey bee toxicity	-	0.8983	89.83%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9924	99.24%

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	97.37%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	89.69%	94.73%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	89.03%	94.42%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.72%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	87.33%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.53%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.30%	94.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	86.15%	93.65%
CHEMBL2581	P07339	Cathepsin D	85.18%	98.95%
CHEMBL5408	Q9UHD2	Serine/threonine-protein kinase TBK1	80.19%	90.48%

Plants that contains it

• Ageratum houstonianum
• Eupatorium cannabinum

Cross-Links

• PubChem: 71336886
• NPASS: NPC44449
• LOTUS: LTS0123542
• wikiData: Q82721409