1,3-Dihydroxy-6,7-dimethoxyxanthen-9-one

Details

• Internal ID: d856ca60-35f0-4213-8e06-cc547654691a
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,3-dihydroxy-6,7-dimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C(=O)C3=C(C=C(C=C3O2)O)O)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C(=O)C3=C(C=C(C=C3O2)O)O)OC
• InChI: InChI=1S/C15H12O6/c1-19-11-5-8-10(6-12(11)20-2)21-13-4-7(16)3-9(17)14(13)15(8)18/h3-6,16-17H,1-2H3
• InChI Key: LOZIYAQUVDQPDB-UHFFFAOYSA-N
• Popularity: 4 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

• CHEMBL3357571

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9261	92.61%
Caco-2	+	0.8958	89.58%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5592	55.92%
OATP2B1 inhibitior	-	0.7052	70.52%
OATP1B1 inhibitior	+	0.9017	90.17%
OATP1B3 inhibitior	+	0.9627	96.27%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8267	82.67%
P-glycoprotein inhibitior	-	0.6170	61.70%
P-glycoprotein substrate	-	0.7101	71.01%
CYP3A4 substrate	-	0.5000	50.00%
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	+	0.4764	47.64%
CYP inhibitory promiscuity	+	0.7479	74.79%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6775	67.75%
Eye corrosion	-	0.9667	96.67%
Eye irritation	+	0.8698	86.98%
Skin irritation	-	0.6148	61.48%
Skin corrosion	-	0.9417	94.17%
Ames mutagenesis	+	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4904	49.04%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8849	88.49%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7136	71.36%
Acute Oral Toxicity (c)	III	0.6228	62.28%
Estrogen receptor binding	+	0.7982	79.82%
Androgen receptor binding	+	0.6768	67.68%
Thyroid receptor binding	+	0.7358	73.58%
Glucocorticoid receptor binding	+	0.8903	89.03%
Aromatase binding	+	0.8119	81.19%
PPAR gamma	+	0.7574	75.74%
Honey bee toxicity	-	0.8781	87.81%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5549	55.49%
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	96.88%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.15%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.99%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.98%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.61%	98.95%
CHEMBL3194	P02766	Transthyretin	88.45%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.23%	99.17%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.23%	93.99%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.78%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.91%	99.23%
CHEMBL2535	P11166	Glucose transporter	85.86%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.61%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.98%	94.45%
CHEMBL1929	P47989	Xanthine dehydrogenase	81.75%	96.12%
CHEMBL3401	O75469	Pregnane X receptor	80.94%	94.73%

Plants that contains it

• Lawsonia inermis
• Maclura tricuspidata

Cross-Links

• PubChem: 69866203
• NPASS: NPC179183
• LOTUS: LTS0099334
• wikiData: Q105154998