6-Hydroxy-2,3,4-trimethoxyxanthone

Details

• Internal ID: 0c29a95d-1f13-41cf-baa0-9baae6f9279e
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 6-hydroxy-2,3,4-trimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)C(=O)C3=C(O2)C=C(C=C3)O)OC)OC
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)C(=O)C3=C(O2)C=C(C=C3)O)OC)OC
• InChI: InChI=1S/C16H14O6/c1-19-12-7-10-13(18)9-5-4-8(17)6-11(9)22-14(10)16(21-3)15(12)20-2/h4-7,17H,1-3H3
• InChI Key: CVRGANONEPHAFP-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₆
• Molecular Weight: 302.28 g/mol
• Exact Mass: 302.07903816 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.68
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9769	97.69%
Caco-2	+	0.7995	79.95%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6863	68.63%
OATP2B1 inhibitior	-	0.5852	58.52%
OATP1B1 inhibitior	+	0.9180	91.80%
OATP1B3 inhibitior	+	0.9884	98.84%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7467	74.67%
P-glycoprotein inhibitior	+	0.5899	58.99%
P-glycoprotein substrate	-	0.7357	73.57%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	-	0.6511	65.11%
CYP2C9 inhibition	-	0.9806	98.06%
CYP2C19 inhibition	-	0.6277	62.77%
CYP2D6 inhibition	-	0.8588	85.88%
CYP1A2 inhibition	+	0.9585	95.85%
CYP2C8 inhibition	+	0.6409	64.09%
CYP inhibitory promiscuity	-	0.5523	55.23%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6004	60.04%
Eye corrosion	-	0.9679	96.79%
Eye irritation	+	0.8422	84.22%
Skin irritation	-	0.6803	68.03%
Skin corrosion	-	0.9860	98.60%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5504	55.04%
Micronuclear	+	0.8359	83.59%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.9331	93.31%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6679	66.79%
Acute Oral Toxicity (c)	II	0.5755	57.55%
Estrogen receptor binding	+	0.7394	73.94%
Androgen receptor binding	+	0.8211	82.11%
Thyroid receptor binding	+	0.6443	64.43%
Glucocorticoid receptor binding	+	0.7831	78.31%
Aromatase binding	+	0.6930	69.30%
PPAR gamma	+	0.6460	64.60%
Honey bee toxicity	-	0.8793	87.93%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.8585	85.85%

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	98.30%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.83%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.96%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.43%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.22%	94.45%
CHEMBL2535	P11166	Glucose transporter	91.18%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.79%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.31%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.62%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.64%	99.23%
CHEMBL3194	P02766	Transthyretin	83.01%	90.71%
CHEMBL4040	P28482	MAP kinase ERK2	80.56%	83.82%

Plants that contains it

• Hypericum monogynum

Cross-Links

• PubChem: 16105271
• LOTUS: LTS0155206
• wikiData: Q104970948