1-hydroxy-8-(hydroxymethyl)-3-methoxy-6-methyl-9H-xanthen-9-one

Details

• Internal ID: d7f04a40-5e44-4d94-a85b-5642ef07021a
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1-hydroxy-8-(hydroxymethyl)-3-methoxy-6-methylxanthen-9-one
• InChI: InChI=1S/C16H14O5/c1-8-3-9(7-17)14-12(4-8)21-13-6-10(20-2)5-11(18)15(13)16(14)19/h3-6,17-18H,7H2,1-2H3
• InChI Key: RWXQNINQKMVTEI-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.08412354 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.46
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• RefChem:76005
• CHEBI:200085
• 1-hydroxy-8-(hydroxymethyl)-3-methoxy-6-methylxanthen-9-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9623	96.23%
Caco-2	+	0.8148	81.48%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7315	73.15%
OATP2B1 inhibitior	-	0.7087	70.87%
OATP1B1 inhibitior	+	0.8824	88.24%
OATP1B3 inhibitior	+	0.9222	92.22%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5413	54.13%
P-glycoprotein inhibitior	-	0.7566	75.66%
P-glycoprotein substrate	-	0.9173	91.73%
CYP3A4 substrate	+	0.5396	53.96%
CYP2C9 substrate	-	0.6228	62.28%
CYP2D6 substrate	-	0.8394	83.94%
CYP3A4 inhibition	+	0.5466	54.66%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	+	0.6425	64.25%
CYP2D6 inhibition	-	0.7798	77.98%
CYP1A2 inhibition	+	0.8009	80.09%
CYP2C8 inhibition	-	0.6502	65.02%
CYP inhibitory promiscuity	+	0.7148	71.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9013	90.13%
Carcinogenicity (trinary)	Non-required	0.6763	67.63%
Eye corrosion	-	0.9644	96.44%
Eye irritation	+	0.7899	78.99%
Skin irritation	-	0.8092	80.92%
Skin corrosion	-	0.9824	98.24%
Ames mutagenesis	+	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6465	64.65%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.9014	90.14%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.6279	62.79%
Acute Oral Toxicity (c)	III	0.7843	78.43%
Estrogen receptor binding	+	0.8355	83.55%
Androgen receptor binding	+	0.7904	79.04%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.8809	88.09%
Aromatase binding	+	0.7935	79.35%
PPAR gamma	+	0.8688	86.88%
Honey bee toxicity	-	0.9042	90.42%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	-	0.3670	36.70%

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	98.16%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.81%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.45%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.96%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.67%	99.15%
CHEMBL2581	P07339	Cathepsin D	92.29%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.28%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.27%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.04%	99.17%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.25%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.04%	89.00%
CHEMBL4208	P20618	Proteasome component C5	87.13%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.28%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.81%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.64%	96.09%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.45%	93.65%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 46918633
• LOTUS: LTS0215277
• wikiData: Q75069150