1,3,8-Trihydroxy-2-methoxyxanthone

Details

• Internal ID: 592c9284-3980-41b1-b8fe-a30bae1b9719
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,3,8-trihydroxy-2-methoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C2=C(C=C1O)OC3=CC=CC(=C3C2=O)O)O
• SMILES (Isomeric): COC1=C(C2=C(C=C1O)OC3=CC=CC(=C3C2=O)O)O
• InChI: InChI=1S/C14H10O6/c1-19-14-7(16)5-9-11(13(14)18)12(17)10-6(15)3-2-4-8(10)20-9/h2-5,15-16,18H,1H3
• InChI Key: SLPZRZRPLQECGV-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₀O₆
• Molecular Weight: 274.22 g/mol
• Exact Mass: 274.04773803 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.07
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 1,3,8-trihydroxy-2-methoxyxanthone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9378	93.78%
Caco-2	+	0.7371	73.71%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5512	55.12%
OATP2B1 inhibitior	-	0.6956	69.56%
OATP1B1 inhibitior	+	0.9122	91.22%
OATP1B3 inhibitior	+	0.9758	97.58%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9018	90.18%
P-glycoprotein inhibitior	-	0.6769	67.69%
P-glycoprotein substrate	-	0.9056	90.56%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.6321	63.21%
CYP2C9 inhibition	-	0.6549	65.49%
CYP2C19 inhibition	+	0.6923	69.23%
CYP2D6 inhibition	-	0.6476	64.76%
CYP1A2 inhibition	+	0.9724	97.24%
CYP2C8 inhibition	-	0.5614	56.14%
CYP inhibitory promiscuity	+	0.7640	76.40%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6276	62.76%
Eye corrosion	-	0.9630	96.30%
Eye irritation	+	0.8804	88.04%
Skin irritation	-	0.5358	53.58%
Skin corrosion	-	0.9315	93.15%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7107	71.07%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.8858	88.58%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7469	74.69%
Acute Oral Toxicity (c)	III	0.7996	79.96%
Estrogen receptor binding	+	0.8811	88.11%
Androgen receptor binding	+	0.6566	65.66%
Thyroid receptor binding	+	0.6584	65.84%
Glucocorticoid receptor binding	+	0.9505	95.05%
Aromatase binding	+	0.7421	74.21%
PPAR gamma	+	0.8444	84.44%
Honey bee toxicity	-	0.9392	93.92%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.7882	78.82%

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	97.41%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.97%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.97%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.54%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.39%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.28%	93.99%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.07%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	88.88%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.55%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.74%	99.23%
CHEMBL2535	P11166	Glucose transporter	84.65%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.34%	99.15%

Plants that contains it

• Hypericum geminiflorum

Cross-Links

• PubChem: 14756212
• LOTUS: LTS0067022
• wikiData: Q105255502