2-Hydroxy-1,6,8-trimethoxyxanthone

Details

• Internal ID: bbe6fe0c-9f33-4854-a375-715453f0de8e
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 2-hydroxy-1,6,8-trimethoxyxanthen-9-one
• SMILES (Canonical): COC1=CC2=C(C(=C1)OC)C(=O)C3=C(O2)C=CC(=C3OC)O
• SMILES (Isomeric): COC1=CC2=C(C(=C1)OC)C(=O)C3=C(O2)C=CC(=C3OC)O
• InChI: InChI=1S/C16H14O6/c1-19-8-6-11(20-2)13-12(7-8)22-10-5-4-9(17)16(21-3)14(10)15(13)18/h4-7,17H,1-3H3
• InChI Key: MBVZBXIYTFWCIV-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₆
• Molecular Weight: 302.28 g/mol
• Exact Mass: 302.07903816 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.68
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 2-hydroxy-1,6,8-trimethoxyxanthone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9769	97.69%
Caco-2	+	0.7967	79.67%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6863	68.63%
OATP2B1 inhibitior	-	0.7211	72.11%
OATP1B1 inhibitior	+	0.9518	95.18%
OATP1B3 inhibitior	+	0.9884	98.84%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8432	84.32%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.9468	94.68%
CYP3A4 substrate	-	0.5307	53.07%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	-	0.6511	65.11%
CYP2C9 inhibition	-	0.9806	98.06%
CYP2C19 inhibition	-	0.6277	62.77%
CYP2D6 inhibition	-	0.8588	85.88%
CYP1A2 inhibition	+	0.9585	95.85%
CYP2C8 inhibition	-	0.5824	58.24%
CYP inhibitory promiscuity	-	0.5523	55.23%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6004	60.04%
Eye corrosion	-	0.9679	96.79%
Eye irritation	+	0.7257	72.57%
Skin irritation	-	0.6803	68.03%
Skin corrosion	-	0.9860	98.60%
Ames mutagenesis	+	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4889	48.89%
Micronuclear	+	0.8359	83.59%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.9331	93.31%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7521	75.21%
Acute Oral Toxicity (c)	II	0.5755	57.55%
Estrogen receptor binding	+	0.8006	80.06%
Androgen receptor binding	+	0.7656	76.56%
Thyroid receptor binding	+	0.5621	56.21%
Glucocorticoid receptor binding	+	0.8841	88.41%
Aromatase binding	+	0.8827	88.27%
PPAR gamma	+	0.7498	74.98%
Honey bee toxicity	-	0.9175	91.75%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
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	98.44%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.43%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.12%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.47%	99.15%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.23%	93.99%
CHEMBL2535	P11166	Glucose transporter	88.87%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.98%	89.00%
CHEMBL4208	P20618	Proteasome component C5	86.95%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.73%	94.45%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.30%	80.78%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.55%	86.33%
CHEMBL3194	P02766	Transthyretin	83.49%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.31%	99.23%
CHEMBL2581	P07339	Cathepsin D	82.97%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.97%	99.17%

Plants that contains it

• Haploclathra leiantha

Cross-Links

• PubChem: 13965887
• LOTUS: LTS0173110
• wikiData: Q105160983