5-Acetyl-6-hydroxy-2-isopropylidene-3(2h)-benzofuranone

Details

• Internal ID: bab74575-f8f2-4ebf-8d22-0359bde605b6
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: 5-acetyl-6-hydroxy-2-propan-2-ylidene-1-benzofuran-3-one
• SMILES (Canonical): CC(=C1C(=O)C2=CC(=C(C=C2O1)O)C(=O)C)C
• SMILES (Isomeric): CC(=C1C(=O)C2=CC(=C(C=C2O1)O)C(=O)C)C
• InChI: InChI=1S/C13H12O4/c1-6(2)13-12(16)9-4-8(7(3)14)10(15)5-11(9)17-13/h4-5,15H,1-3H3
• InChI Key: OHWFUKAVYSSEQD-UHFFFAOYSA-N
• Popularity: 1 reference 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: 2.80
• Atomic LogP (AlogP): 2.46
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	+	0.7176	71.76%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7764	77.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9453	94.53%
OATP1B3 inhibitior	+	0.9519	95.19%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9458	94.58%
P-glycoprotein inhibitior	-	0.9340	93.40%
P-glycoprotein substrate	-	0.9445	94.45%
CYP3A4 substrate	-	0.6188	61.88%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8585	85.85%
CYP3A4 inhibition	-	0.8569	85.69%
CYP2C9 inhibition	+	0.6334	63.34%
CYP2C19 inhibition	+	0.5692	56.92%
CYP2D6 inhibition	-	0.9097	90.97%
CYP1A2 inhibition	+	0.9232	92.32%
CYP2C8 inhibition	-	0.8944	89.44%
CYP inhibitory promiscuity	+	0.6608	66.08%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.4441	44.41%
Eye corrosion	-	0.9568	95.68%
Eye irritation	+	0.9538	95.38%
Skin irritation	-	0.5743	57.43%
Skin corrosion	-	0.9212	92.12%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8052	80.52%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	+	0.4814	48.14%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.5905	59.05%
Acute Oral Toxicity (c)	III	0.5296	52.96%
Estrogen receptor binding	+	0.6269	62.69%
Androgen receptor binding	-	0.6163	61.63%
Thyroid receptor binding	-	0.6922	69.22%
Glucocorticoid receptor binding	-	0.7426	74.26%
Aromatase binding	+	0.5837	58.37%
PPAR gamma	-	0.6069	60.69%
Honey bee toxicity	-	0.9180	91.80%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.8300	83.00%
Fish aquatic toxicity	+	0.9827	98.27%

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	95.63%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.14%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.51%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.03%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.24%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	87.73%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.32%	85.14%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	83.13%	94.42%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.63%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.62%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.37%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.88%	90.71%
CHEMBL1811	P34995	Prostanoid EP1 receptor	80.11%	95.71%

Plants that contains it

• Ligularia nelumbifolia

Cross-Links

• PubChem: 101675284
• LOTUS: LTS0030703
• wikiData: Q105192341