1-Methyl-5,7,8-trihydroxy-6-methoxynaphtho[2,3-c]furan-4,9-dione

Details

• Internal ID: 861689c4-5f8a-46f1-b4af-320db3b9b68b
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: 5,7,8-trihydroxy-6-methoxy-1-methylbenzo[f][2]benzofuran-4,9-dione
• SMILES (Canonical): CC1=C2C(=CO1)C(=O)C3=C(C2=O)C(=C(C(=C3O)OC)O)O
• SMILES (Isomeric): CC1=C2C(=CO1)C(=O)C3=C(C2=O)C(=C(C(=C3O)OC)O)O
• InChI: InChI=1S/C14H10O7/c1-4-6-5(3-21-4)9(15)7-8(10(6)16)11(17)13(19)14(20-2)12(7)18/h3,17-19H,1-2H3
• InChI Key: PIHXYYPPGZULGB-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₀O₇
• Molecular Weight: 290.22 g/mol
• Exact Mass: 290.04265265 g/mol
• Topological Polar Surface Area (TPSA): 117.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.49
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 5,7,8-trihydroxy-6-methoxy-1-methylbenzo(f)(2)benzofuran-4,9-dione
• 5,7,8-trihydroxy-6-methoxy-1-methylbenzo[f][2]benzofuran-4,9-dione
• RefChem:149357
• CHEBI:225917
• 5,7,8-trihydroxy-6-methoxy-1-methylbenzo[][2]benzouran-4,9-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9355	93.55%
Caco-2	-	0.5841	58.41%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6437	64.37%
OATP2B1 inhibitior	-	0.7136	71.36%
OATP1B1 inhibitior	+	0.8694	86.94%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8948	89.48%
P-glycoprotein inhibitior	-	0.8205	82.05%
P-glycoprotein substrate	-	0.9592	95.92%
CYP3A4 substrate	-	0.5253	52.53%
CYP2C9 substrate	-	0.6495	64.95%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	-	0.6638	66.38%
CYP2C9 inhibition	-	0.6480	64.80%
CYP2C19 inhibition	-	0.6943	69.43%
CYP2D6 inhibition	-	0.7927	79.27%
CYP1A2 inhibition	+	0.8520	85.20%
CYP2C8 inhibition	-	0.7511	75.11%
CYP inhibitory promiscuity	+	0.6238	62.38%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.5053	50.53%
Eye corrosion	-	0.9843	98.43%
Eye irritation	+	0.8107	81.07%
Skin irritation	-	0.7131	71.31%
Skin corrosion	-	0.9175	91.75%
Ames mutagenesis	+	0.6236	62.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.6303	63.03%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8132	81.32%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5431	54.31%
Acute Oral Toxicity (c)	III	0.5351	53.51%
Estrogen receptor binding	-	0.4893	48.93%
Androgen receptor binding	-	0.6069	60.69%
Thyroid receptor binding	-	0.7103	71.03%
Glucocorticoid receptor binding	+	0.6627	66.27%
Aromatase binding	+	0.5739	57.39%
PPAR gamma	+	0.5291	52.91%
Honey bee toxicity	-	0.9133	91.33%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9585	95.85%

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	95.84%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.20%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.57%	94.00%
CHEMBL2581	P07339	Cathepsin D	89.98%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.40%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.12%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.96%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	83.32%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.17%	86.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 136814281
• LOTUS: LTS0256655
• wikiData: Q104194821