8,9-Dihydroxynaphtho[2,3-c]furan-1(3H)-one

Details

• Internal ID: a147e42d-d89b-4186-b7b2-735464d88be5
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: 4,5-dihydroxy-1H-benzo[f][2]benzofuran-3-one
• SMILES (Canonical): C1C2=C(C(=C3C(=C2)C=CC=C3O)O)C(=O)O1
• SMILES (Isomeric): C1C2=C(C(=C3C(=C2)C=CC=C3O)O)C(=O)O1
• InChI: InChI=1S/C12H8O4/c13-8-3-1-2-6-4-7-5-16-12(15)10(7)11(14)9(6)8/h1-4,13-14H,5H2
• InChI Key: JDGOEFZZYBWLFE-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₈O₄
• Molecular Weight: 216.19 g/mol
• Exact Mass: 216.04225873 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.92
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• DTXSID201268956
• 492-23-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9660	96.60%
Caco-2	+	0.6464	64.64%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6875	68.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9415	94.15%
OATP1B3 inhibitior	+	0.8637	86.37%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8573	85.73%
P-glycoprotein inhibitior	-	0.9531	95.31%
P-glycoprotein substrate	-	0.9423	94.23%
CYP3A4 substrate	-	0.6017	60.17%
CYP2C9 substrate	-	0.5852	58.52%
CYP2D6 substrate	-	0.8572	85.72%
CYP3A4 inhibition	-	0.5850	58.50%
CYP2C9 inhibition	+	0.6809	68.09%
CYP2C19 inhibition	-	0.5337	53.37%
CYP2D6 inhibition	-	0.8139	81.39%
CYP1A2 inhibition	+	0.7387	73.87%
CYP2C8 inhibition	-	0.8558	85.58%
CYP inhibitory promiscuity	+	0.6479	64.79%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5716	57.16%
Eye corrosion	-	0.9874	98.74%
Eye irritation	+	0.9816	98.16%
Skin irritation	-	0.5656	56.56%
Skin corrosion	-	0.9693	96.93%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8774	87.74%
Micronuclear	+	0.7974	79.74%
Hepatotoxicity	+	0.8250	82.50%
skin sensitisation	-	0.8380	83.80%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.5700	57.00%
Acute Oral Toxicity (c)	III	0.3526	35.26%
Estrogen receptor binding	+	0.7202	72.02%
Androgen receptor binding	+	0.7518	75.18%
Thyroid receptor binding	-	0.5294	52.94%
Glucocorticoid receptor binding	+	0.8112	81.12%
Aromatase binding	+	0.5936	59.36%
PPAR gamma	+	0.7133	71.33%
Honey bee toxicity	-	0.9535	95.35%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9593	95.93%

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	98.77%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.30%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.61%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.17%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.29%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.74%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	88.05%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.53%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.17%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.76%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.21%	89.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.85%	93.40%
CHEMBL2535	P11166	Glucose transporter	81.76%	98.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.59%	93.99%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	81.52%	83.10%

Plants that contains it

• Rhamnus wightii

Cross-Links

• PubChem: 12442905
• LOTUS: LTS0107882
• wikiData: Q105125459