5,8-dihydroxy-6-methoxy-2-methylbenzo[g]chromen-4-one

Details

• Internal ID: 16112368-7971-4d30-9bd7-92fdfefb7ca9
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: 5,8-dihydroxy-6-methoxy-2-methylbenzo[g]chromen-4-one
• SMILES (Canonical): CC1=CC(=O)C2=C(C3=C(C=C(C=C3C=C2O1)O)OC)O
• SMILES (Isomeric): CC1=CC(=O)C2=C(C3=C(C=C(C=C3C=C2O1)O)OC)O
• InChI: InChI=1S/C15H12O5/c1-7-3-10(17)14-12(20-7)5-8-4-9(16)6-11(19-2)13(8)15(14)18/h3-6,16,18H,1-2H3
• InChI Key: KLKFLNXANXGSIT-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.25 g/mol
• Exact Mass: 272.06847348 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.67
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9773	97.73%
Caco-2	+	0.7403	74.03%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7452	74.52%
OATP2B1 inhibitior	-	0.7106	71.06%
OATP1B1 inhibitior	+	0.9273	92.73%
OATP1B3 inhibitior	+	0.9883	98.83%
MATE1 inhibitior	-	0.6000	60.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8534	85.34%
P-glycoprotein inhibitior	-	0.6918	69.18%
P-glycoprotein substrate	-	0.8634	86.34%
CYP3A4 substrate	+	0.5287	52.87%
CYP2C9 substrate	-	0.6360	63.60%
CYP2D6 substrate	-	0.8410	84.10%
CYP3A4 inhibition	+	0.6594	65.94%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	+	0.6485	64.85%
CYP2D6 inhibition	-	0.6581	65.81%
CYP1A2 inhibition	+	0.9384	93.84%
CYP2C8 inhibition	-	0.6424	64.24%
CYP inhibitory promiscuity	+	0.5835	58.35%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9113	91.13%
Carcinogenicity (trinary)	Non-required	0.5853	58.53%
Eye corrosion	-	0.9501	95.01%
Eye irritation	+	0.8788	87.88%
Skin irritation	-	0.6852	68.52%
Skin corrosion	-	0.9858	98.58%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5329	53.29%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.9553	95.53%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.5736	57.36%
Acute Oral Toxicity (c)	III	0.8166	81.66%
Estrogen receptor binding	+	0.7801	78.01%
Androgen receptor binding	+	0.7336	73.36%
Thyroid receptor binding	+	0.5552	55.52%
Glucocorticoid receptor binding	+	0.7922	79.22%
Aromatase binding	+	0.7687	76.87%
PPAR gamma	+	0.7117	71.17%
Honey bee toxicity	-	0.8878	88.78%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.7651	76.51%

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	96.68%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.15%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	90.84%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.57%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.04%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.70%	85.14%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	88.86%	94.42%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.59%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.88%	99.23%
CHEMBL2581	P07339	Cathepsin D	86.34%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.10%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.98%	90.71%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.63%	93.65%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10038860
• LOTUS: LTS0033185
• wikiData: Q82249075