Naphtho[2,3-c]furan-4,9-dione, 5,8-dihydroxy-1-methyl-

Details

• Internal ID: e5be7dc6-449c-4114-a616-048bc9d0b65f
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: 5,8-dihydroxy-3-methylbenzo[f][2]benzofuran-4,9-dione
• SMILES (Canonical): CC1=C2C(=CO1)C(=O)C3=C(C=CC(=C3C2=O)O)O
• SMILES (Isomeric): CC1=C2C(=CO1)C(=O)C3=C(C=CC(=C3C2=O)O)O
• InChI: InChI=1S/C13H8O5/c1-5-9-6(4-18-5)12(16)10-7(14)2-3-8(15)11(10)13(9)17/h2-4,14-15H,1H3
• InChI Key: JYJNQZBODMZAMR-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₈O₅
• Molecular Weight: 244.20 g/mol
• Exact Mass: 244.03717335 g/mol
• Topological Polar Surface Area (TPSA): 87.70 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 1.77
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 200726-49-4
• DTXSID50466950

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9930	99.30%
Caco-2	-	0.6947	69.47%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8127	81.27%
OATP2B1 inhibitior	-	0.7138	71.38%
OATP1B1 inhibitior	+	0.9440	94.40%
OATP1B3 inhibitior	+	0.9610	96.10%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9202	92.02%
P-glycoprotein inhibitior	-	0.9200	92.00%
P-glycoprotein substrate	-	0.9796	97.96%
CYP3A4 substrate	-	0.6231	62.31%
CYP2C9 substrate	-	0.6368	63.68%
CYP2D6 substrate	-	0.8522	85.22%
CYP3A4 inhibition	-	0.8627	86.27%
CYP2C9 inhibition	+	0.9107	91.07%
CYP2C19 inhibition	-	0.5326	53.26%
CYP2D6 inhibition	-	0.8515	85.15%
CYP1A2 inhibition	+	0.9566	95.66%
CYP2C8 inhibition	-	0.9064	90.64%
CYP inhibitory promiscuity	+	0.5485	54.85%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9043	90.43%
Carcinogenicity (trinary)	Non-required	0.4263	42.63%
Eye corrosion	-	0.9822	98.22%
Eye irritation	+	0.7970	79.70%
Skin irritation	+	0.4898	48.98%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	+	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8562	85.62%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.8865	88.65%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.7848	78.48%
Acute Oral Toxicity (c)	III	0.5748	57.48%
Estrogen receptor binding	-	0.5844	58.44%
Androgen receptor binding	+	0.5810	58.10%
Thyroid receptor binding	-	0.7551	75.51%
Glucocorticoid receptor binding	+	0.7353	73.53%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6698	66.98%
Honey bee toxicity	-	0.9498	94.98%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9656	96.56%

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	94.80%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.17%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.69%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.56%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.48%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.09%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.22%	99.15%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.58%	93.65%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.78%	94.00%

Plants that contains it

• Bulbine capitata
• Bulbine frutescens

Cross-Links

• PubChem: 135496998
• LOTUS: LTS0193454
• wikiData: Q27121346