1,3,8-Trihydroxy-4-methoxy-9H-xanthen-9-one

Details

• Internal ID: 16c67cd1-22d8-4419-8d67-a5dbc3e5ec10
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,3,8-trihydroxy-4-methoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C=C(C2=C1OC3=CC=CC(=C3C2=O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C2=C1OC3=CC=CC(=C3C2=O)O)O)O
• InChI: InChI=1S/C14H10O6/c1-19-13-8(17)5-7(16)11-12(18)10-6(15)3-2-4-9(10)20-14(11)13/h2-5,15-17H,1H3
• InChI Key: VFHZSXCOKBPSHN-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-4-METHOXY-9H-XANTHEN-9-ONE
• DTXSID70758900
• 1,3,8-trihydroxy-4-methoxyxanthone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9378	93.78%
Caco-2	+	0.5637	56.37%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5512	55.12%
OATP2B1 inhibitior	-	0.6980	69.80%
OATP1B1 inhibitior	+	0.9240	92.40%
OATP1B3 inhibitior	+	0.9758	97.58%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7071	70.71%
P-glycoprotein inhibitior	-	0.7809	78.09%
P-glycoprotein substrate	-	0.8794	87.94%
CYP3A4 substrate	-	0.5195	51.95%
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	-	0.7097	70.97%
CYP inhibitory promiscuity	+	0.7640	76.40%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6276	62.76%
Eye corrosion	-	0.9630	96.30%
Eye irritation	+	0.8881	88.81%
Skin irritation	-	0.5358	53.58%
Skin corrosion	-	0.9315	93.15%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7199	71.99%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.8858	88.58%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6196	61.96%
Acute Oral Toxicity (c)	III	0.7996	79.96%
Estrogen receptor binding	+	0.9054	90.54%
Androgen receptor binding	+	0.6540	65.40%
Thyroid receptor binding	+	0.5326	53.26%
Glucocorticoid receptor binding	+	0.9591	95.91%
Aromatase binding	+	0.6920	69.20%
PPAR gamma	+	0.7667	76.67%
Honey bee toxicity	-	0.9460	94.60%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
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	97.42%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.94%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.23%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.70%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.15%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.28%	94.73%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.18%	93.99%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.77%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.34%	99.23%
CHEMBL2535	P11166	Glucose transporter	88.19%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.31%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.41%	99.15%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.22%	93.65%

Plants that contains it

• Hypericum geminiflorum

Cross-Links

• PubChem: 71330160
• LOTUS: LTS0211800
• wikiData: Q82712581