5-Hydroxy-3-methylbenzo[f][2]benzofuran-4,9-dione

Details

• Internal ID: 8f034235-2f46-4c56-bafe-d1be30be909e
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: 5-hydroxy-3-methylbenzo[f][2]benzofuran-4,9-dione
• SMILES (Canonical): CC1=C2C(=CO1)C(=O)C3=C(C2=O)C(=CC=C3)O
• SMILES (Isomeric): CC1=C2C(=CO1)C(=O)C3=C(C2=O)C(=CC=C3)O
• InChI: InChI=1S/C13H8O4/c1-6-10-8(5-17-6)12(15)7-3-2-4-9(14)11(7)13(10)16/h2-5,14H,1H3
• InChI Key: GBXTYRYFKWXLAP-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₈O₄
• Molecular Weight: 228.20 g/mol
• Exact Mass: 228.04225873 g/mol
• Topological Polar Surface Area (TPSA): 67.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.07
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	-	0.5132	51.32%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7559	75.59%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9281	92.81%
OATP1B3 inhibitior	+	0.9784	97.84%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9376	93.76%
P-glycoprotein inhibitior	-	0.8884	88.84%
P-glycoprotein substrate	-	0.9382	93.82%
CYP3A4 substrate	-	0.5409	54.09%
CYP2C9 substrate	-	0.6368	63.68%
CYP2D6 substrate	-	0.8522	85.22%
CYP3A4 inhibition	-	0.8607	86.07%
CYP2C9 inhibition	+	0.8133	81.33%
CYP2C19 inhibition	-	0.6396	63.96%
CYP2D6 inhibition	-	0.9071	90.71%
CYP1A2 inhibition	+	0.9721	97.21%
CYP2C8 inhibition	-	0.8442	84.42%
CYP inhibitory promiscuity	-	0.5931	59.31%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8943	89.43%
Carcinogenicity (trinary)	Non-required	0.4078	40.78%
Eye corrosion	-	0.9755	97.55%
Eye irritation	+	0.8647	86.47%
Skin irritation	+	0.5069	50.69%
Skin corrosion	-	0.9698	96.98%
Ames mutagenesis	+	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8511	85.11%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.8723	87.23%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.8233	82.33%
Acute Oral Toxicity (c)	III	0.5087	50.87%
Estrogen receptor binding	+	0.6186	61.86%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.6536	65.36%
Glucocorticoid receptor binding	+	0.6329	63.29%
Aromatase binding	+	0.5451	54.51%
PPAR gamma	+	0.5476	54.76%
Honey bee toxicity	-	0.9488	94.88%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9638	96.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.43%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.71%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	94.22%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.93%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.10%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.14%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.96%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.08%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.86%	86.33%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.58%	93.65%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.41%	93.03%

Plants that contains it

• Aloe ferox
• Bulbine capitata

Cross-Links

• PubChem: 11390536
• LOTUS: LTS0007568
• wikiData: Q105006135