(3R)-3-hydroxy-2,2,3-trimethyl-4H-pyrano[3,2-c]xanthen-7-one

Details

• Internal ID: faa2e14a-1511-457e-99fb-7abbc951003c
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > Pyranoxanthones
• IUPAC Name: (3R)-3-hydroxy-2,2,3-trimethyl-4H-pyrano[3,2-c]xanthen-7-one
• SMILES (Canonical): CC1(C(CC2=C(O1)C3=C(C=C2)C(=O)C4=CC=CC=C4O3)(C)O)C
• SMILES (Isomeric): C[C@]1(CC2=C(C3=C(C=C2)C(=O)C4=CC=CC=C4O3)OC1(C)C)O
• InChI: InChI=1S/C19H18O4/c1-18(2)19(3,21)10-11-8-9-13-15(20)12-6-4-5-7-14(12)22-17(13)16(11)23-18/h4-9,21H,10H2,1-3H3/t19-/m1/s1
• InChI Key: IIWLXMFDLGCBFC-LJQANCHMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₄
• Molecular Weight: 310.30 g/mol
• Exact Mass: 310.12050905 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.41
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• (3R)-3-hydroxy-2,2,3-trimethyl-4H-pyrano[3,2-c]xanthen-7-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	+	0.6007	60.07%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6105	61.05%
OATP2B1 inhibitior	-	0.7213	72.13%
OATP1B1 inhibitior	+	0.9061	90.61%
OATP1B3 inhibitior	+	0.9733	97.33%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.4713	47.13%
P-glycoprotein inhibitior	-	0.6102	61.02%
P-glycoprotein substrate	-	0.7414	74.14%
CYP3A4 substrate	+	0.6251	62.51%
CYP2C9 substrate	-	0.8221	82.21%
CYP2D6 substrate	-	0.7659	76.59%
CYP3A4 inhibition	-	0.7737	77.37%
CYP2C9 inhibition	-	0.9449	94.49%
CYP2C19 inhibition	-	0.8764	87.64%
CYP2D6 inhibition	-	0.8385	83.85%
CYP1A2 inhibition	+	0.6630	66.30%
CYP2C8 inhibition	-	0.7849	78.49%
CYP inhibitory promiscuity	-	0.9483	94.83%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6153	61.53%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.7903	79.03%
Skin irritation	-	0.6787	67.87%
Skin corrosion	-	0.9335	93.35%
Ames mutagenesis	+	0.5230	52.30%
Human Ether-a-go-go-Related Gene inhibition	-	0.6819	68.19%
Micronuclear	-	0.6041	60.41%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7608	76.08%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.4880	48.80%
Acute Oral Toxicity (c)	III	0.7573	75.73%
Estrogen receptor binding	+	0.8241	82.41%
Androgen receptor binding	+	0.8031	80.31%
Thyroid receptor binding	+	0.6482	64.82%
Glucocorticoid receptor binding	+	0.7909	79.09%
Aromatase binding	+	0.6879	68.79%
PPAR gamma	+	0.8569	85.69%
Honey bee toxicity	-	0.9367	93.67%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9421	94.21%

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	99.45%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.41%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.40%	99.23%
CHEMBL2581	P07339	Cathepsin D	92.05%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.33%	89.00%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	85.23%	85.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.86%	94.45%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	84.50%	93.65%
CHEMBL3401	O75469	Pregnane X receptor	81.92%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.65%	94.00%
CHEMBL4208	P20618	Proteasome component C5	81.46%	90.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.41%	93.99%

Plants that contains it

• Calophyllum caledonicum

Cross-Links

• PubChem: 493292
• LOTUS: LTS0105195
• wikiData: Q105113797