1-Hydroxy-2,3-dimethoxy-9H-xanthen-9-one

Details

• Internal ID: 172bfe3c-075d-45dc-b886-64c6990a2d78
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1-hydroxy-2,3-dimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)OC3=CC=CC=C3C2=O)O)OC
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)OC3=CC=CC=C3C2=O)O)OC
• InChI: InChI=1S/C15H12O5/c1-18-11-7-10-12(14(17)15(11)19-2)13(16)8-5-3-4-6-9(8)20-10/h3-7,17H,1-2H3
• InChI Key: BQJUODDGBIJUDP-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.25 g/mol
• Exact Mass: 272.06847348 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.67
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 6747-02-0
• 9H-Xanthen-9-one, 1-hydroxy-2,3-dimethoxy-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9791	97.91%
Caco-2	+	0.8862	88.62%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7024	70.24%
OATP2B1 inhibitior	-	0.7243	72.43%
OATP1B1 inhibitior	+	0.9124	91.24%
OATP1B3 inhibitior	+	0.9932	99.32%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7325	73.25%
P-glycoprotein inhibitior	+	0.6455	64.55%
P-glycoprotein substrate	-	0.7494	74.94%
CYP3A4 substrate	+	0.5677	56.77%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.5215	52.15%
CYP2C9 inhibition	-	0.8938	89.38%
CYP2C19 inhibition	+	0.6902	69.02%
CYP2D6 inhibition	-	0.7703	77.03%
CYP1A2 inhibition	+	0.9595	95.95%
CYP2C8 inhibition	+	0.5805	58.05%
CYP inhibitory promiscuity	+	0.5264	52.64%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6210	62.10%
Eye corrosion	-	0.9551	95.51%
Eye irritation	+	0.8625	86.25%
Skin irritation	-	0.5807	58.07%
Skin corrosion	-	0.9822	98.22%
Ames mutagenesis	+	0.5936	59.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.5536	55.36%
Micronuclear	+	0.8959	89.59%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.9125	91.25%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8324	83.24%
Acute Oral Toxicity (c)	III	0.4994	49.94%
Estrogen receptor binding	+	0.7633	76.33%
Androgen receptor binding	+	0.7474	74.74%
Thyroid receptor binding	+	0.7129	71.29%
Glucocorticoid receptor binding	+	0.8955	89.55%
Aromatase binding	+	0.8747	87.47%
PPAR gamma	+	0.7641	76.41%
Honey bee toxicity	-	0.8919	89.19%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5851	58.51%
Fish aquatic toxicity	+	0.8492	84.92%

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	98.84%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.89%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.41%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.12%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.23%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.12%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.63%	93.99%
CHEMBL2581	P07339	Cathepsin D	89.60%	98.95%
CHEMBL2535	P11166	Glucose transporter	89.10%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.95%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.58%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	85.33%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.37%	95.50%

Plants that contains it

• Glaucium flavum
• Sesbania bispinosa

Cross-Links

• PubChem: 71439574
• NPASS: NPC115
• LOTUS: LTS0151867
• wikiData: Q104944397