9-Hydroxy-3,3-dimethylpyrano[3,2-a]xanthen-12(3H)-one

Details

• Internal ID: 92b747c2-e9a9-4101-b40b-13ada510acee
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > Pyranoxanthones
• IUPAC Name: 9-hydroxy-3,3-dimethylpyrano[3,2-a]xanthen-12-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C=CC3=C2C(=O)C4=C(O3)C=C(C=C4)O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=CC3=C2C(=O)C4=C(O3)C=C(C=C4)O)C
• InChI: InChI=1S/C18H14O4/c1-18(2)8-7-11-13(22-18)5-6-14-16(11)17(20)12-4-3-10(19)9-15(12)21-14/h3-9,19H,1-2H3
• InChI Key: WUBJQVSGRLKHQK-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₄O₄
• Molecular Weight: 294.30 g/mol
• Exact Mass: 294.08920892 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.84
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 9-Hydroxy-3,3-dimethylpyrano[3,2-a]xanthen-12(3H)-one
• 131189-44-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9927	99.27%
Caco-2	+	0.7449	74.49%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7856	78.56%
OATP2B1 inhibitior	-	0.5890	58.90%
OATP1B1 inhibitior	+	0.8560	85.60%
OATP1B3 inhibitior	+	0.9898	98.98%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5580	55.80%
P-glycoprotein inhibitior	+	0.6264	62.64%
P-glycoprotein substrate	-	0.5885	58.85%
CYP3A4 substrate	+	0.5690	56.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8317	83.17%
CYP3A4 inhibition	+	0.6382	63.82%
CYP2C9 inhibition	+	0.5632	56.32%
CYP2C19 inhibition	+	0.5466	54.66%
CYP2D6 inhibition	-	0.8005	80.05%
CYP1A2 inhibition	+	0.6007	60.07%
CYP2C8 inhibition	-	0.5716	57.16%
CYP inhibitory promiscuity	-	0.5425	54.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9713	97.13%
Carcinogenicity (trinary)	Non-required	0.5742	57.42%
Eye corrosion	-	0.9826	98.26%
Eye irritation	+	0.7934	79.34%
Skin irritation	-	0.6576	65.76%
Skin corrosion	-	0.9612	96.12%
Ames mutagenesis	+	0.5963	59.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5774	57.74%
Micronuclear	+	0.6959	69.59%
Hepatotoxicity	+	0.5158	51.58%
skin sensitisation	-	0.7053	70.53%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6289	62.89%
Acute Oral Toxicity (c)	III	0.6414	64.14%
Estrogen receptor binding	+	0.9622	96.22%
Androgen receptor binding	+	0.8727	87.27%
Thyroid receptor binding	+	0.8249	82.49%
Glucocorticoid receptor binding	+	0.9274	92.74%
Aromatase binding	+	0.8881	88.81%
PPAR gamma	+	0.9016	90.16%
Honey bee toxicity	-	0.8622	86.22%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9599	95.99%

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	98.67%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.63%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.00%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.64%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.73%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	88.04%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.92%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.68%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	84.76%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.35%	94.00%
CHEMBL242	Q92731	Estrogen receptor beta	83.77%	98.35%
CHEMBL2535	P11166	Glucose transporter	81.80%	98.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.46%	93.99%
CHEMBL4208	P20618	Proteasome component C5	80.36%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.04%	85.14%

Plants that contains it

• Hypericum reflexum

Cross-Links

• PubChem: 14757908
• LOTUS: LTS0219510
• wikiData: Q105312947