2,4-Dihydroxy-3,6-dimethoxyxanthone

Details

• Internal ID: 09a300ff-27f5-4702-8a01-773be5899366
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 2,4-dihydroxy-3,6-dimethoxyxanthen-9-one
• SMILES (Canonical): COC1=CC2=C(C=C1)C(=O)C3=CC(=C(C(=C3O2)O)OC)O
• SMILES (Isomeric): COC1=CC2=C(C=C1)C(=O)C3=CC(=C(C(=C3O2)O)OC)O
• InChI: InChI=1S/C15H12O6/c1-19-7-3-4-8-11(5-7)21-14-9(12(8)17)6-10(16)15(20-2)13(14)18/h3-6,16,18H,1-2H3
• InChI Key: ZXBBHUMRKRZKQC-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: 2.20
• 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	+	0.9261	92.61%
Caco-2	+	0.8207	82.07%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5592	55.92%
OATP2B1 inhibitior	-	0.7061	70.61%
OATP1B1 inhibitior	+	0.9265	92.65%
OATP1B3 inhibitior	+	0.9627	96.27%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8721	87.21%
P-glycoprotein inhibitior	-	0.5365	53.65%
P-glycoprotein substrate	-	0.8785	87.85%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
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	-	0.6946	69.46%
CYP inhibitory promiscuity	+	0.7479	74.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6775	67.75%
Eye corrosion	-	0.9667	96.67%
Eye irritation	+	0.8243	82.43%
Skin irritation	-	0.6148	61.48%
Skin corrosion	-	0.9417	94.17%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6422	64.22%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.5560	55.60%
skin sensitisation	-	0.8849	88.49%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8078	80.78%
Acute Oral Toxicity (c)	III	0.6228	62.28%
Estrogen receptor binding	+	0.7556	75.56%
Androgen receptor binding	+	0.7749	77.49%
Thyroid receptor binding	+	0.5452	54.52%
Glucocorticoid receptor binding	+	0.8809	88.09%
Aromatase binding	+	0.8192	81.92%
PPAR gamma	+	0.8179	81.79%
Honey bee toxicity	-	0.9134	91.34%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
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	99.69%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.73%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.14%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.90%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.82%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.10%	94.45%
CHEMBL2581	P07339	Cathepsin D	88.54%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.39%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.60%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.97%	93.99%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.66%	80.78%
CHEMBL4208	P20618	Proteasome component C5	84.94%	90.00%
CHEMBL1907	P15144	Aminopeptidase N	84.57%	93.31%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.61%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.23%	99.17%
CHEMBL2535	P11166	Glucose transporter	83.14%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	81.45%	94.73%

Plants that contains it

• Hypericum reflexum

Cross-Links

• PubChem: 14757912
• LOTUS: LTS0180499
• wikiData: Q105385369