1,3,6-Trihydroxy-4,5-dimethoxy-8-methylxanthen-9-one

Details

• Internal ID: 1a4fff9c-08a9-4506-af33-4470c1a5b3c5
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,3,6-trihydroxy-4,5-dimethoxy-8-methylxanthen-9-one
• SMILES (Canonical): CC1=CC(=C(C2=C1C(=O)C3=C(O2)C(=C(C=C3O)O)OC)OC)O
• SMILES (Isomeric): CC1=CC(=C(C2=C1C(=O)C3=C(O2)C(=C(C=C3O)O)OC)OC)O
• InChI: InChI=1S/C16H14O7/c1-6-4-8(18)13(21-2)15-10(6)12(20)11-7(17)5-9(19)14(22-3)16(11)23-15/h4-5,17-19H,1-3H3
• InChI Key: QWPLJWMHZGDSRF-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₇
• Molecular Weight: 318.28 g/mol
• Exact Mass: 318.07395278 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9232	92.32%
Caco-2	+	0.7157	71.57%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5279	52.79%
OATP2B1 inhibitior	-	0.7025	70.25%
OATP1B1 inhibitior	+	0.9444	94.44%
OATP1B3 inhibitior	+	0.9332	93.32%
MATE1 inhibitior	-	0.6000	60.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6918	69.18%
P-glycoprotein inhibitior	-	0.7102	71.02%
P-glycoprotein substrate	-	0.9440	94.40%
CYP3A4 substrate	-	0.5697	56.97%
CYP2C9 substrate	-	0.6360	63.60%
CYP2D6 substrate	-	0.8410	84.10%
CYP3A4 inhibition	+	0.5125	51.25%
CYP2C9 inhibition	-	0.9202	92.02%
CYP2C19 inhibition	-	0.6069	60.69%
CYP2D6 inhibition	-	0.6399	63.99%
CYP1A2 inhibition	+	0.9412	94.12%
CYP2C8 inhibition	-	0.8516	85.16%
CYP inhibitory promiscuity	+	0.6880	68.80%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6372	63.72%
Eye corrosion	-	0.9745	97.45%
Eye irritation	+	0.9532	95.32%
Skin irritation	-	0.6903	69.03%
Skin corrosion	-	0.9596	95.96%
Ames mutagenesis	-	0.5964	59.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.6849	68.49%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.9087	90.87%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6420	64.20%
Acute Oral Toxicity (c)	III	0.5195	51.95%
Estrogen receptor binding	+	0.8315	83.15%
Androgen receptor binding	-	0.5144	51.44%
Thyroid receptor binding	+	0.6293	62.93%
Glucocorticoid receptor binding	+	0.8566	85.66%
Aromatase binding	+	0.5729	57.29%
PPAR gamma	+	0.7029	70.29%
Honey bee toxicity	-	0.9066	90.66%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.8379	83.79%

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	97.54%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.15%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.74%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.64%	99.15%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	90.40%	93.65%
CHEMBL3401	O75469	Pregnane X receptor	87.86%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.13%	89.00%
CHEMBL2581	P07339	Cathepsin D	83.85%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.54%	86.33%
CHEMBL4208	P20618	Proteasome component C5	83.09%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.55%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.54%	99.17%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.95%	93.99%
CHEMBL3194	P02766	Transthyretin	80.51%	90.71%

Plants that contains it

• Drimiopsis maculata

Cross-Links

• PubChem: 11483958
• LOTUS: LTS0148446
• wikiData: Q105229325