1-Hydroxy-3,6,8-trimethoxyxanthen-9-one

Details

• Internal ID: 014d6577-96eb-4929-b8c4-cc378f68bed3
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1-hydroxy-3,6,8-trimethoxyxanthen-9-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC3=C(C2=O)C(=CC(=C3)OC)OC)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC3=C(C2=O)C(=CC(=C3)OC)OC)O
• InChI: InChI=1S/C16H14O6/c1-19-8-4-10(17)14-12(6-8)22-13-7-9(20-2)5-11(21-3)15(13)16(14)18/h4-7,17H,1-3H3
• InChI Key: JBSFSRSYBUWRRZ-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₆
• Molecular Weight: 302.28 g/mol
• Exact Mass: 302.07903816 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.68
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9841	98.41%
Caco-2	+	0.8457	84.57%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6678	66.78%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.9230	92.30%
OATP1B3 inhibitior	+	0.9873	98.73%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6963	69.63%
P-glycoprotein inhibitior	-	0.4743	47.43%
P-glycoprotein substrate	-	0.9244	92.44%
CYP3A4 substrate	-	0.5406	54.06%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.5994	59.94%
CYP2C9 inhibition	-	0.9188	91.88%
CYP2C19 inhibition	-	0.6082	60.82%
CYP2D6 inhibition	-	0.8535	85.35%
CYP1A2 inhibition	+	0.9359	93.59%
CYP2C8 inhibition	-	0.6334	63.34%
CYP inhibitory promiscuity	-	0.6092	60.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9113	91.13%
Carcinogenicity (trinary)	Non-required	0.5650	56.50%
Eye corrosion	-	0.9482	94.82%
Eye irritation	+	0.8328	83.28%
Skin irritation	-	0.7107	71.07%
Skin corrosion	-	0.9915	99.15%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6841	68.41%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.9602	96.02%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.4669	46.69%
Acute Oral Toxicity (c)	III	0.5893	58.93%
Estrogen receptor binding	+	0.8424	84.24%
Androgen receptor binding	+	0.7244	72.44%
Thyroid receptor binding	+	0.7007	70.07%
Glucocorticoid receptor binding	+	0.7147	71.47%
Aromatase binding	+	0.8932	89.32%
PPAR gamma	+	0.7761	77.61%
Honey bee toxicity	-	0.9129	91.29%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5249	52.49%
Fish aquatic toxicity	+	0.7667	76.67%

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	96.22%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.61%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.52%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.73%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.81%	89.00%
CHEMBL3194	P02766	Transthyretin	87.46%	90.71%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.35%	93.99%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.17%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.33%	86.33%
CHEMBL4208	P20618	Proteasome component C5	85.98%	90.00%
CHEMBL2581	P07339	Cathepsin D	85.36%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.04%	99.17%
CHEMBL2535	P11166	Glucose transporter	84.76%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	82.22%	94.73%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.34%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.98%	99.23%

Plants that contains it

• Baccharis santelicis
• Halenia elliptica
• Helichrysum stoechas

Cross-Links

• PubChem: 14539318
• LOTUS: LTS0205618
• wikiData: Q105119036