4,6-Dihydroxy-2,3-dimethoxyxanthone

Details

• Internal ID: 6d9aee3d-5fd5-4a30-a9de-1223dd91c9ef
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 4,6-dihydroxy-2,3-dimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)C(=O)C3=C(O2)C=C(C=C3)O)O)OC
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)C(=O)C3=C(O2)C=C(C=C3)O)O)OC
• InChI: InChI=1S/C15H12O6/c1-19-11-6-9-12(17)8-4-3-7(16)5-10(8)21-14(9)13(18)15(11)20-2/h3-6,16,18H,1-2H3
• InChI Key: NSFBDGHGPHBJPY-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₆
• Molecular Weight: 288.25 g/mol
• Exact Mass: 288.06338810 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9642	96.42%
Caco-2	+	0.7579	75.79%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7364	73.64%
OATP2B1 inhibitior	-	0.7037	70.37%
OATP1B1 inhibitior	+	0.9020	90.20%
OATP1B3 inhibitior	+	0.9851	98.51%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7883	78.83%
P-glycoprotein inhibitior	-	0.5601	56.01%
P-glycoprotein substrate	-	0.6911	69.11%
CYP3A4 substrate	+	0.5207	52.07%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	-	0.6420	64.20%
CYP2C9 inhibition	-	0.7071	70.71%
CYP2C19 inhibition	+	0.7531	75.31%
CYP2D6 inhibition	-	0.6235	62.35%
CYP1A2 inhibition	+	0.9606	96.06%
CYP2C8 inhibition	+	0.6612	66.12%
CYP inhibitory promiscuity	+	0.6446	64.46%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6331	63.31%
Eye corrosion	-	0.9655	96.55%
Eye irritation	+	0.8765	87.65%
Skin irritation	-	0.6099	60.99%
Skin corrosion	-	0.9698	96.98%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7176	71.76%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.9149	91.49%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7889	78.89%
Acute Oral Toxicity (c)	III	0.5708	57.08%
Estrogen receptor binding	+	0.7224	72.24%
Androgen receptor binding	+	0.7625	76.25%
Thyroid receptor binding	+	0.6094	60.94%
Glucocorticoid receptor binding	+	0.8702	87.02%
Aromatase binding	+	0.8329	83.29%
PPAR gamma	+	0.7352	73.52%
Honey bee toxicity	-	0.8848	88.48%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8585	85.85%

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	98.94%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.14%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.08%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.84%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.37%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.62%	86.33%
CHEMBL2535	P11166	Glucose transporter	88.38%	98.75%
CHEMBL2581	P07339	Cathepsin D	88.32%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.62%	99.17%
CHEMBL3194	P02766	Transthyretin	86.56%	90.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.85%	89.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.75%	99.23%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.55%	80.78%

Plants that contains it

• Cratoxylum cochinchinense

Cross-Links

• PubChem: 16105267
• LOTUS: LTS0221144
• wikiData: Q105184991