5,8-Dihydroxy-2-methyl-4H-naphtho[2,3-b]pyran-4,6,9-trione

Details

• Internal ID: b0640c16-9d66-4d69-a9cc-d4669c20c3dc
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: 5,6-dihydroxy-2-methylbenzo[g]chromene-4,8,9-trione
• InChI: InChI=1S/C14H8O6/c1-5-2-7(15)12-10(20-5)3-6-11(14(12)19)8(16)4-9(17)13(6)18/h2-4,16,19H,1H3
• InChI Key: NPUXQAACUNUHIX-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₈O₆
• Molecular Weight: 272.21 g/mol
• Exact Mass: 272.03208797 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.47
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 62681-86-1
• Canarion
• DTXSID30703895
• CHEBI:144210
• 5,6-Dihydroxy-2-methyl-4H-naphtho[2,3-b]pyran-4,8,9-trione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9587	95.87%
Caco-2	+	0.5905	59.05%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5545	55.45%
OATP2B1 inhibitior	-	0.7045	70.45%
OATP1B1 inhibitior	+	0.8839	88.39%
OATP1B3 inhibitior	+	0.9696	96.96%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9643	96.43%
P-glycoprotein inhibitior	-	0.8923	89.23%
P-glycoprotein substrate	-	0.8620	86.20%
CYP3A4 substrate	+	0.5277	52.77%
CYP2C9 substrate	-	0.6079	60.79%
CYP2D6 substrate	-	0.8754	87.54%
CYP3A4 inhibition	-	0.5608	56.08%
CYP2C9 inhibition	+	0.7949	79.49%
CYP2C19 inhibition	-	0.5212	52.12%
CYP2D6 inhibition	-	0.8697	86.97%
CYP1A2 inhibition	+	0.8728	87.28%
CYP2C8 inhibition	-	0.8320	83.20%
CYP inhibitory promiscuity	+	0.7862	78.62%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5626	56.26%
Eye corrosion	-	0.9884	98.84%
Eye irritation	+	0.8304	83.04%
Skin irritation	+	0.5153	51.53%
Skin corrosion	-	0.8671	86.71%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7920	79.20%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.6703	67.03%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.5657	56.57%
Acute Oral Toxicity (c)	III	0.4606	46.06%
Estrogen receptor binding	+	0.5767	57.67%
Androgen receptor binding	+	0.6110	61.10%
Thyroid receptor binding	-	0.7383	73.83%
Glucocorticoid receptor binding	+	0.8263	82.63%
Aromatase binding	-	0.6162	61.62%
PPAR gamma	+	0.5698	56.98%
Honey bee toxicity	-	0.9124	91.24%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9713	97.13%

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	96.48%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.62%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.47%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.58%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.18%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.84%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	89.83%	91.49%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	87.94%	96.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.62%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.21%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.78%	90.71%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	86.69%	93.65%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	85.34%	94.42%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.90%	86.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 53483342
• LOTUS: LTS0227371
• wikiData: Q82636158