9H-Xanthen-9-one, 2-hydroxy-5-methoxy-

Details

• Internal ID: 87c7b7aa-a315-47be-a525-de03d4301c69
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 2-hydroxy-5-methoxyxanthen-9-one
• SMILES (Canonical): COC1=CC=CC2=C1OC3=C(C2=O)C=C(C=C3)O
• SMILES (Isomeric): COC1=CC=CC2=C1OC3=C(C2=O)C=C(C=C3)O
• InChI: InChI=1S/C14H10O4/c1-17-12-4-2-3-9-13(16)10-7-8(15)5-6-11(10)18-14(9)12/h2-7,15H,1H3
• InChI Key: CBMAAZVYXIBRLC-UHFFFAOYSA-N
• Popularity: 4 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

• 70786-46-8
• 2-hydroxy-5-methoxyxanthone
• DTXSID00221036

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9846	98.46%
Caco-2	-	0.5699	56.99%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6551	65.51%
OATP2B1 inhibitior	-	0.8687	86.87%
OATP1B1 inhibitior	+	0.9012	90.12%
OATP1B3 inhibitior	+	0.9952	99.52%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7711	77.11%
P-glycoprotein inhibitior	-	0.6913	69.13%
P-glycoprotein substrate	-	0.7682	76.82%
CYP3A4 substrate	+	0.5649	56.49%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	+	0.5981	59.81%
CYP2C9 inhibition	-	0.7716	77.16%
CYP2C19 inhibition	+	0.6254	62.54%
CYP2D6 inhibition	-	0.8637	86.37%
CYP1A2 inhibition	+	0.9667	96.67%
CYP2C8 inhibition	+	0.4852	48.52%
CYP inhibitory promiscuity	-	0.5933	59.33%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4627	46.27%
Eye corrosion	-	0.8980	89.80%
Eye irritation	+	0.7805	78.05%
Skin irritation	-	0.5327	53.27%
Skin corrosion	-	0.9840	98.40%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7062	70.62%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.9316	93.16%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6459	64.59%
Acute Oral Toxicity (c)	III	0.9193	91.93%
Estrogen receptor binding	+	0.7776	77.76%
Androgen receptor binding	+	0.9086	90.86%
Thyroid receptor binding	+	0.5635	56.35%
Glucocorticoid receptor binding	+	0.7384	73.84%
Aromatase binding	+	0.7425	74.25%
PPAR gamma	+	0.5943	59.43%
Honey bee toxicity	-	0.8796	87.96%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.6426	64.26%

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	98.21%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.94%	95.56%
CHEMBL2535	P11166	Glucose transporter	95.08%	98.75%
CHEMBL2581	P07339	Cathepsin D	94.53%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.39%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.99%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.83%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.07%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.00%	85.14%
CHEMBL1255126	O15151	Protein Mdm4	83.82%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.68%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	82.71%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.62%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.65%	95.50%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.38%	94.03%

Plants that contains it

• Cratoxylum cochinchinense
• Hypericum canariense

Cross-Links

• PubChem: 156048
• LOTUS: LTS0270518
• wikiData: Q83098617