2-Hydroxy-3-methoxyxanthone

Details

• Internal ID: 548d09d8-693f-4153-b7f8-8f454ba787d2
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 2-hydroxy-3-methoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)OC3=CC=CC=C3C2=O)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1)OC3=CC=CC=C3C2=O)O
• InChI: InChI=1S/C14H10O4/c1-17-13-7-12-9(6-10(13)15)14(16)8-4-2-3-5-11(8)18-12/h2-7,15H,1H3
• InChI Key: ZXVAPEXGRPGWCF-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₀O₄
• Molecular Weight: 242.23 g/mol
• Exact Mass: 242.05790880 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.66
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 33018-31-4
• 9H-Xanthen-9-one, 2-hydroxy-3-methoxy-
• DTXSID00480762

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9836	98.36%
Caco-2	+	0.7636	76.36%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7146	71.46%
OATP2B1 inhibitior	-	0.8655	86.55%
OATP1B1 inhibitior	+	0.9212	92.12%
OATP1B3 inhibitior	+	0.9973	99.73%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8347	83.47%
P-glycoprotein inhibitior	-	0.6715	67.15%
P-glycoprotein substrate	-	0.7909	79.09%
CYP3A4 substrate	+	0.5251	52.51%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	-	0.5835	58.35%
CYP2C9 inhibition	-	0.8319	83.19%
CYP2C19 inhibition	+	0.7001	70.01%
CYP2D6 inhibition	-	0.8533	85.33%
CYP1A2 inhibition	+	0.9798	97.98%
CYP2C8 inhibition	-	0.6679	66.79%
CYP inhibitory promiscuity	+	0.5273	52.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5441	54.41%
Eye corrosion	-	0.9412	94.12%
Eye irritation	+	0.9201	92.01%
Skin irritation	+	0.5142	51.42%
Skin corrosion	-	0.9802	98.02%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7973	79.73%
Micronuclear	+	0.8959	89.59%
Hepatotoxicity	-	0.6803	68.03%
skin sensitisation	-	0.9229	92.29%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6331	63.31%
Acute Oral Toxicity (c)	III	0.8366	83.66%
Estrogen receptor binding	+	0.9183	91.83%
Androgen receptor binding	+	0.7610	76.10%
Thyroid receptor binding	+	0.6423	64.23%
Glucocorticoid receptor binding	+	0.9117	91.17%
Aromatase binding	+	0.9093	90.93%
PPAR gamma	+	0.7627	76.27%
Honey bee toxicity	-	0.9044	90.44%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5351	53.51%
Fish aquatic toxicity	+	0.8149	81.49%

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	99.27%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.21%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.26%	94.00%
CHEMBL2581	P07339	Cathepsin D	92.98%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.41%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.74%	89.00%
CHEMBL2535	P11166	Glucose transporter	90.05%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.19%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.05%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	84.75%	94.73%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.91%	93.99%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.81%	99.17%

Plants that contains it

• Dalbergia sissoides
• Hypericum hookerianum

Cross-Links

• PubChem: 12214327
• LOTUS: LTS0155562
• wikiData: Q82315821