1,5,8-Trihydroxy-3,4-dimethoxyxanthone

Details

• Internal ID: ea484a59-fa45-4bae-a68b-8170e8ba2c72
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,5,8-trihydroxy-3,4-dimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C2=C(C(=C1)O)C(=O)C3=C(C=CC(=C3O2)O)O)OC
• SMILES (Isomeric): COC1=C(C2=C(C(=C1)O)C(=O)C3=C(C=CC(=C3O2)O)O)OC
• InChI: InChI=1S/C15H12O7/c1-20-9-5-8(18)11-12(19)10-6(16)3-4-7(17)13(10)22-15(11)14(9)21-2/h3-5,16-18H,1-2H3
• InChI Key: ZXGKYKCGVKMAQK-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₇
• Molecular Weight: 304.25 g/mol
• Exact Mass: 304.05830272 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.08
• 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	+	0.9642	96.42%
Caco-2	+	0.6846	68.46%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7364	73.64%
OATP2B1 inhibitior	-	0.7005	70.05%
OATP1B1 inhibitior	+	0.9575	95.75%
OATP1B3 inhibitior	+	0.9851	98.51%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7706	77.06%
P-glycoprotein inhibitior	-	0.6550	65.50%
P-glycoprotein substrate	-	0.9243	92.43%
CYP3A4 substrate	-	0.5503	55.03%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.6420	64.20%
CYP2C9 inhibition	-	0.7071	70.71%
CYP2C19 inhibition	+	0.7531	75.31%
CYP2D6 inhibition	-	0.6235	62.35%
CYP1A2 inhibition	+	0.9606	96.06%
CYP2C8 inhibition	-	0.5650	56.50%
CYP inhibitory promiscuity	+	0.6446	64.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6331	63.31%
Eye corrosion	-	0.9655	96.55%
Eye irritation	+	0.8452	84.52%
Skin irritation	-	0.6099	60.99%
Skin corrosion	-	0.9698	96.98%
Ames mutagenesis	+	0.7136	71.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.7190	71.90%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.5053	50.53%
skin sensitisation	-	0.9149	91.49%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.4922	49.22%
Acute Oral Toxicity (c)	III	0.5708	57.08%
Estrogen receptor binding	+	0.7420	74.20%
Androgen receptor binding	+	0.6812	68.12%
Thyroid receptor binding	+	0.6098	60.98%
Glucocorticoid receptor binding	+	0.9051	90.51%
Aromatase binding	+	0.7320	73.20%
PPAR gamma	+	0.7734	77.34%
Honey bee toxicity	-	0.9156	91.56%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5749	57.49%
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	97.85%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.18%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.82%	94.00%
CHEMBL3194	P02766	Transthyretin	90.13%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.24%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.57%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.51%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.72%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.69%	99.15%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.80%	93.99%
CHEMBL2535	P11166	Glucose transporter	84.65%	98.75%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.20%	80.78%
CHEMBL4208	P20618	Proteasome component C5	81.69%	90.00%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	80.19%	98.11%
CHEMBL3401	O75469	Pregnane X receptor	80.07%	94.73%

Plants that contains it

• Gentiana algida
• Lomatogonium carinthiacum

Cross-Links

• PubChem: 86183532
• LOTUS: LTS0191358
• wikiData: Q105385525