1,5-Dihydroxy-3,8-dimethoxy xanthone

Details

• Internal ID: d681b254-6821-4aee-b589-ee4cf55fe41d
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,5-dihydroxy-3,8-dimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C2C(=C(C=C1)O)OC3=CC(=CC(=C3C2=O)O)OC
• SMILES (Isomeric): COC1=C2C(=C(C=C1)O)OC3=CC(=CC(=C3C2=O)O)OC
• InChI: InChI=1S/C15H12O6/c1-19-7-5-9(17)12-11(6-7)21-15-8(16)3-4-10(20-2)13(15)14(12)18/h3-6,16-17H,1-2H3
• InChI Key: HCOBNXLXVQFNAR-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

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9667	96.67%
Caco-2	+	0.6652	66.52%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7124	71.24%
OATP2B1 inhibitior	-	0.7012	70.12%
OATP1B1 inhibitior	+	0.9225	92.25%
OATP1B3 inhibitior	+	0.9684	96.84%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7139	71.39%
P-glycoprotein inhibitior	-	0.5536	55.36%
P-glycoprotein substrate	-	0.9043	90.43%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.5761	57.61%
CYP2C9 inhibition	-	0.7134	71.34%
CYP2C19 inhibition	+	0.5920	59.20%
CYP2D6 inhibition	-	0.6221	62.21%
CYP1A2 inhibition	+	0.9017	90.17%
CYP2C8 inhibition	+	0.6020	60.20%
CYP inhibitory promiscuity	+	0.5329	53.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5697	56.97%
Eye corrosion	-	0.9515	95.15%
Eye irritation	+	0.8166	81.66%
Skin irritation	-	0.6608	66.08%
Skin corrosion	-	0.9812	98.12%
Ames mutagenesis	+	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7080	70.80%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9261	92.61%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.5609	56.09%
Acute Oral Toxicity (c)	III	0.7448	74.48%
Estrogen receptor binding	+	0.9009	90.09%
Androgen receptor binding	+	0.8530	85.30%
Thyroid receptor binding	+	0.6313	63.13%
Glucocorticoid receptor binding	+	0.9310	93.10%
Aromatase binding	+	0.8743	87.43%
PPAR gamma	+	0.8377	83.77%
Honey bee toxicity	-	0.9192	91.92%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5649	56.49%
Fish aquatic toxicity	+	0.7067	70.67%

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	96.38%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.53%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.00%	94.00%
CHEMBL3194	P02766	Transthyretin	93.56%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.03%	99.15%
CHEMBL2535	P11166	Glucose transporter	89.61%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.43%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.98%	89.00%
CHEMBL4208	P20618	Proteasome component C5	88.63%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.50%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.38%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.23%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.84%	99.23%
CHEMBL2581	P07339	Cathepsin D	83.64%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	82.96%	94.73%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.10%	93.65%

Plants that contains it

• Gentiana algida
• Swertia chirayta
• Swertia cuneata

Cross-Links

• PubChem: 10356746
• LOTUS: LTS0260443
• wikiData: Q105025876