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

Details

• Internal ID: 3c8ff5f4-7d12-4b72-a6f9-86ee59018b07
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: 8-hydroxy-5-methoxy-3-methylbenzo[f][2]benzofuran-4,9-dione
• SMILES (Canonical): CC1=C2C(=CO1)C(=O)C3=C(C=CC(=C3C2=O)OC)O
• SMILES (Isomeric): CC1=C2C(=CO1)C(=O)C3=C(C=CC(=C3C2=O)OC)O
• InChI: InChI=1S/C14H10O5/c1-6-10-7(5-19-6)13(16)11-8(15)3-4-9(18-2)12(11)14(10)17/h3-5,15H,1-2H3
• InChI Key: GYKOSPGHDOKDEY-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₀O₅
• Molecular Weight: 258.23 g/mol
• Exact Mass: 258.05282342 g/mol
• Topological Polar Surface Area (TPSA): 76.70 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.08
• H-Bond Acceptor: 5
• 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	+	0.9942	99.42%
Caco-2	+	0.6776	67.76%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7665	76.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9513	95.13%
OATP1B3 inhibitior	+	0.9638	96.38%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8447	84.47%
P-glycoprotein inhibitior	-	0.8557	85.57%
P-glycoprotein substrate	-	0.9390	93.90%
CYP3A4 substrate	-	0.5205	52.05%
CYP2C9 substrate	-	0.6395	63.95%
CYP2D6 substrate	-	0.8306	83.06%
CYP3A4 inhibition	-	0.7620	76.20%
CYP2C9 inhibition	+	0.7288	72.88%
CYP2C19 inhibition	+	0.5283	52.83%
CYP2D6 inhibition	-	0.7369	73.69%
CYP1A2 inhibition	+	0.9601	96.01%
CYP2C8 inhibition	-	0.6436	64.36%
CYP inhibitory promiscuity	+	0.5971	59.71%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8843	88.43%
Carcinogenicity (trinary)	Non-required	0.4635	46.35%
Eye corrosion	-	0.9732	97.32%
Eye irritation	+	0.7552	75.52%
Skin irritation	-	0.7626	76.26%
Skin corrosion	-	0.9806	98.06%
Ames mutagenesis	+	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7555	75.55%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.9092	90.92%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.7945	79.45%
Acute Oral Toxicity (c)	II	0.5216	52.16%
Estrogen receptor binding	+	0.6865	68.65%
Androgen receptor binding	+	0.6513	65.13%
Thyroid receptor binding	-	0.5396	53.96%
Glucocorticoid receptor binding	+	0.5756	57.56%
Aromatase binding	+	0.6409	64.09%
PPAR gamma	+	0.7073	70.73%
Honey bee toxicity	-	0.8885	88.85%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9475	94.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.74%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.04%	94.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.34%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.65%	89.00%
CHEMBL2581	P07339	Cathepsin D	87.24%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	87.10%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.84%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.62%	86.33%
CHEMBL4208	P20618	Proteasome component C5	84.33%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.14%	99.15%
CHEMBL3194	P02766	Transthyretin	83.71%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.65%	96.00%

Plants that contains it

• Bulbine capitata

Cross-Links

• PubChem: 11311446
• LOTUS: LTS0168414
• wikiData: Q105023861