3,8-Dihydroxy-1,4-dimethoxyxanthone

Details

• Internal ID: 704b1303-a226-4e20-a2e3-7e0ad9ca7651
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 3,8-dihydroxy-1,4-dimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C2C(=C(C(=C1)O)OC)OC3=CC=CC(=C3C2=O)O
• SMILES (Isomeric): COC1=C2C(=C(C(=C1)O)OC)OC3=CC=CC(=C3C2=O)O
• InChI: InChI=1S/C15H12O6/c1-19-10-6-8(17)14(20-2)15-12(10)13(18)11-7(16)4-3-5-9(11)21-15/h3-6,16-17H,1-2H3
• InChI Key: UTSXEYFPPZBRJQ-UHFFFAOYSA-N
• Popularity: 2 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: 2.70
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 3,8-dihydroxy-1,4-dimethoxyxanthone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9642	96.42%
Caco-2	+	0.8168	81.68%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7364	73.64%
OATP2B1 inhibitior	-	0.7074	70.74%
OATP1B1 inhibitior	+	0.9272	92.72%
OATP1B3 inhibitior	+	0.9851	98.51%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.4626	46.26%
P-glycoprotein inhibitior	-	0.5846	58.46%
P-glycoprotein substrate	-	0.8785	87.85%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
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	-	0.5826	58.26%
CYP inhibitory promiscuity	+	0.6446	64.46%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6331	63.31%
Eye corrosion	-	0.9655	96.55%
Eye irritation	+	0.8233	82.33%
Skin irritation	-	0.6099	60.99%
Skin corrosion	-	0.9698	96.98%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6212	62.12%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.5625	56.25%
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	-	0.5988	59.88%
Acute Oral Toxicity (c)	III	0.5708	57.08%
Estrogen receptor binding	+	0.8944	89.44%
Androgen receptor binding	+	0.6387	63.87%
Thyroid receptor binding	+	0.5976	59.76%
Glucocorticoid receptor binding	+	0.9323	93.23%
Aromatase binding	+	0.7745	77.45%
PPAR gamma	+	0.8074	80.74%
Honey bee toxicity	-	0.9319	93.19%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5949	59.49%
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	96.20%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.35%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.98%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.45%	86.33%
CHEMBL2581	P07339	Cathepsin D	92.38%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.29%	93.99%
CHEMBL2535	P11166	Glucose transporter	91.15%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.46%	89.00%
CHEMBL1255126	O15151	Protein Mdm4	87.81%	90.20%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.62%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	85.58%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.03%	94.45%
CHEMBL3194	P02766	Transthyretin	83.63%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.51%	99.17%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	82.17%	94.03%

Plants that contains it

• Swertia chirayta

Cross-Links

• PubChem: 86108288
• LOTUS: LTS0159168
• wikiData: Q105279072