2,3-Dihydroxy-1,6,7-trimethoxyxanthone

Details

• Internal ID: 231ec9b6-d2ed-4e80-b25f-900ace5651af
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 2,3-dihydroxy-1,6,7-trimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C(=O)C3=C(O2)C=C(C(=C3OC)O)O)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C(=O)C3=C(O2)C=C(C(=C3OC)O)O)OC
• InChI: InChI=1S/C16H14O7/c1-20-10-4-7-9(6-11(10)21-2)23-12-5-8(17)15(19)16(22-3)13(12)14(7)18/h4-6,17,19H,1-3H3
• InChI Key: HXDDCCDTVYUVJA-UHFFFAOYSA-N
• Popularity: 2 references 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): 94.40 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9294	92.94%
Caco-2	+	0.7073	70.73%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6932	69.32%
OATP2B1 inhibitior	-	0.7131	71.31%
OATP1B1 inhibitior	+	0.9385	93.85%
OATP1B3 inhibitior	+	0.9854	98.54%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7787	77.87%
P-glycoprotein inhibitior	-	0.6102	61.02%
P-glycoprotein substrate	-	0.7630	76.30%
CYP3A4 substrate	-	0.5216	52.16%
CYP2C9 substrate	-	0.8397	83.97%
CYP2D6 substrate	-	0.7876	78.76%
CYP3A4 inhibition	-	0.8238	82.38%
CYP2C9 inhibition	-	0.9803	98.03%
CYP2C19 inhibition	-	0.8316	83.16%
CYP2D6 inhibition	-	0.8437	84.37%
CYP1A2 inhibition	+	0.9413	94.13%
CYP2C8 inhibition	-	0.6492	64.92%
CYP inhibitory promiscuity	-	0.6287	62.87%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6169	61.69%
Eye corrosion	-	0.9768	97.68%
Eye irritation	+	0.8721	87.21%
Skin irritation	-	0.7008	70.08%
Skin corrosion	-	0.9660	96.60%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6799	67.99%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9167	91.67%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8952	89.52%
Acute Oral Toxicity (c)	II	0.4802	48.02%
Estrogen receptor binding	+	0.8158	81.58%
Androgen receptor binding	+	0.6432	64.32%
Thyroid receptor binding	+	0.5577	55.77%
Glucocorticoid receptor binding	+	0.8865	88.65%
Aromatase binding	+	0.8829	88.29%
PPAR gamma	+	0.7166	71.66%
Honey bee toxicity	-	0.9076	90.76%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5249	52.49%
Fish aquatic toxicity	+	0.8871	88.71%

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	99.14%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.31%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.86%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.68%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.97%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.44%	99.17%
CHEMBL3194	P02766	Transthyretin	84.40%	90.71%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.77%	93.99%
CHEMBL2581	P07339	Cathepsin D	83.51%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.27%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.27%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.22%	86.33%
CHEMBL2535	P11166	Glucose transporter	81.59%	98.75%
CHEMBL1255126	O15151	Protein Mdm4	80.48%	90.20%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.46%	80.78%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.16%	94.42%

Plants that contains it

• Hypericum geminiflorum

Cross-Links

• PubChem: 91508983
• LOTUS: LTS0238023
• wikiData: Q105034930