3,8-Dihydroxy-1,2-dimethoxy-9H-xanthen-9-one

Details

• Internal ID: 558c9277-354c-4bd9-8bf2-e770c17ac3fa
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 3,8-dihydroxy-1,2-dimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C2=C(C=C1O)OC3=CC=CC(=C3C2=O)O)OC
• SMILES (Isomeric): COC1=C(C2=C(C=C1O)OC3=CC=CC(=C3C2=O)O)OC
• InChI: InChI=1S/C15H12O6/c1-19-14-8(17)6-10-12(15(14)20-2)13(18)11-7(16)4-3-5-9(11)21-10/h3-6,16-17H,1-2H3
• InChI Key: WGHXAVBNSLELQQ-UHFFFAOYSA-N
• Popularity: 15 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

• 1,6-dihydroxy-7,8-dimethoxyxanthone
• 3,8-Dihydroxy-1,2-dimethoxy-9H-xanthen-9-one
• 34211-52-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9642	96.42%
Caco-2	+	0.8099	80.99%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7364	73.64%
OATP2B1 inhibitior	-	0.7091	70.91%
OATP1B1 inhibitior	+	0.9297	92.97%
OATP1B3 inhibitior	+	0.9851	98.51%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8309	83.09%
P-glycoprotein inhibitior	-	0.5666	56.66%
P-glycoprotein substrate	-	0.9157	91.57%
CYP3A4 substrate	-	0.5165	51.65%
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	-	0.6518	65.18%
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	+	0.7991	79.91%
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	-	0.5708	57.08%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.6449	64.49%
skin sensitisation	-	0.9149	91.49%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6817	68.17%
Acute Oral Toxicity (c)	III	0.5708	57.08%
Estrogen receptor binding	+	0.8711	87.11%
Androgen receptor binding	+	0.6593	65.93%
Thyroid receptor binding	+	0.7022	70.22%
Glucocorticoid receptor binding	+	0.9148	91.48%
Aromatase binding	+	0.7831	78.31%
PPAR gamma	+	0.7621	76.21%
Honey bee toxicity	-	0.9503	95.03%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
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	96.78%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.70%	93.99%
CHEMBL2581	P07339	Cathepsin D	93.59%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.97%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.57%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.68%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.11%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	87.08%	83.82%
CHEMBL2535	P11166	Glucose transporter	86.76%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.85%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.95%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	83.61%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.76%	99.15%

Plants that contains it

• Bonnetia paniculata
• Calophyllum apetalum
• Calophyllum brasiliense
• Calophyllum teysmannii
• Cratoxylum cochinchinense
• Polygala nyikensis

Cross-Links

• PubChem: 14630572
• LOTUS: LTS0055171
• wikiData: Q105304511