1,4,8-Trihydroxy-2,3,6-trimethoxyxanthen-9-one

Details

• Internal ID: c90d2359-7983-41b3-bed5-d26a876f3da3
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,4,8-trihydroxy-2,3,6-trimethoxyxanthen-9-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC3=C(C(=C(C(=C3C2=O)O)OC)OC)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC3=C(C(=C(C(=C3C2=O)O)OC)OC)O)O
• InChI: InChI=1S/C16H14O8/c1-21-6-4-7(17)9-8(5-6)24-14-10(11(9)18)12(19)15(22-2)16(23-3)13(14)20/h4-5,17,19-20H,1-3H3
• InChI Key: QAEDNOBQEIAWSV-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₈
• Molecular Weight: 334.28 g/mol
• Exact Mass: 334.06886740 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.09
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9617	96.17%
Caco-2	+	0.7276	72.76%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7093	70.93%
OATP2B1 inhibitior	-	0.6995	69.95%
OATP1B1 inhibitior	+	0.8842	88.42%
OATP1B3 inhibitior	+	0.9698	96.98%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7947	79.47%
P-glycoprotein inhibitior	-	0.5970	59.70%
P-glycoprotein substrate	-	0.9236	92.36%
CYP3A4 substrate	+	0.5055	50.55%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.7782	77.82%
CYP2C9 inhibition	-	0.9325	93.25%
CYP2C19 inhibition	-	0.5514	55.14%
CYP2D6 inhibition	-	0.7363	73.63%
CYP1A2 inhibition	+	0.9561	95.61%
CYP2C8 inhibition	+	0.4506	45.06%
CYP inhibitory promiscuity	+	0.5753	57.53%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6097	60.97%
Eye corrosion	-	0.9746	97.46%
Eye irritation	+	0.8291	82.91%
Skin irritation	-	0.6975	69.75%
Skin corrosion	-	0.9788	97.88%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7481	74.81%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.9328	93.28%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7528	75.28%
Acute Oral Toxicity (c)	II	0.4834	48.34%
Estrogen receptor binding	+	0.6583	65.83%
Androgen receptor binding	+	0.5753	57.53%
Thyroid receptor binding	+	0.5575	55.75%
Glucocorticoid receptor binding	+	0.8535	85.35%
Aromatase binding	+	0.7181	71.81%
PPAR gamma	+	0.7533	75.33%
Honey bee toxicity	-	0.9089	90.89%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8676	86.76%

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	98.88%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.01%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.55%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.31%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.48%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.38%	89.00%
CHEMBL3194	P02766	Transthyretin	88.09%	90.71%
CHEMBL2581	P07339	Cathepsin D	87.73%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.29%	93.99%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.96%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.51%	99.17%
CHEMBL4208	P20618	Proteasome component C5	86.19%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.38%	86.33%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.24%	94.42%
CHEMBL3401	O75469	Pregnane X receptor	83.83%	94.73%

Plants that contains it

• Schenkia spicata

Cross-Links

• PubChem: 162991657
• LOTUS: LTS0152620
• wikiData: Q105217351