2,7-Dimethoxy-1,3,6,8-tetrahydroxyxanthone

Details

• Internal ID: 585692b9-06b5-46e4-9ffd-47519016d914
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,3,6,8-tetrahydroxy-2,7-dimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C2=C(C=C1O)OC3=C(C2=O)C(=C(C(=C3)O)OC)O)O
• SMILES (Isomeric): COC1=C(C2=C(C=C1O)OC3=C(C2=O)C(=C(C(=C3)O)OC)O)O
• InChI: InChI=1S/C15H12O8/c1-21-14-5(16)3-7-9(12(14)19)11(18)10-8(23-7)4-6(17)15(22-2)13(10)20/h3-4,16-17,19-20H,1-2H3
• InChI Key: LYCMTRLSGDVTRF-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₈
• Molecular Weight: 320.25 g/mol
• Exact Mass: 320.05321734 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.79
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 1,3,6,8-tetrahydroxy-2,7-dimethoxyxanthone
• 1,3,6,8-tetrahydroxy-2,7-dimethoxyxanthen-9-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9261	92.61%
Caco-2	+	0.8048	80.48%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5592	55.92%
OATP2B1 inhibitior	-	0.6935	69.35%
OATP1B1 inhibitior	+	0.9290	92.90%
OATP1B3 inhibitior	+	0.9627	96.27%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9348	93.48%
P-glycoprotein inhibitior	-	0.6808	68.08%
P-glycoprotein substrate	-	0.9634	96.34%
CYP3A4 substrate	-	0.5984	59.84%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.6908	69.08%
CYP2C9 inhibition	-	0.7416	74.16%
CYP2C19 inhibition	+	0.6596	65.96%
CYP2D6 inhibition	-	0.5311	53.11%
CYP1A2 inhibition	+	0.9466	94.66%
CYP2C8 inhibition	-	0.8270	82.70%
CYP inhibitory promiscuity	+	0.7479	74.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6775	67.75%
Eye corrosion	-	0.9667	96.67%
Eye irritation	+	0.8907	89.07%
Skin irritation	-	0.6148	61.48%
Skin corrosion	-	0.9417	94.17%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6896	68.96%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8849	88.49%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8086	80.86%
Acute Oral Toxicity (c)	III	0.6228	62.28%
Estrogen receptor binding	+	0.8161	81.61%
Androgen receptor binding	+	0.5566	55.66%
Thyroid receptor binding	+	0.5305	53.05%
Glucocorticoid receptor binding	+	0.8271	82.71%
Aromatase binding	+	0.7163	71.63%
PPAR gamma	+	0.6838	68.38%
Honey bee toxicity	-	0.9099	90.99%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8268	82.68%

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	98.34%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.05%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.88%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.49%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.46%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.36%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.31%	94.45%
CHEMBL3194	P02766	Transthyretin	83.22%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.19%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	82.38%	94.73%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.35%	93.99%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.09%	99.15%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.39%	94.42%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.07%	99.17%

Plants that contains it

• Eriocaulon buergerianum
• Polygala cyparissias

Cross-Links

• PubChem: 15380735
• LOTUS: LTS0049364
• wikiData: Q105159224