1,5-Dihydroxy-2,3,4-trimethoxyxanthen-9-one

Details

• Internal ID: e7f89350-ae70-4b7f-aa04-c5af44729fa7
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,5-dihydroxy-2,3,4-trimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1O)C(=O)C3=C(O2)C(=CC=C3)O)OC)OC
• SMILES (Isomeric): COC1=C(C(=C2C(=C1O)C(=O)C3=C(O2)C(=CC=C3)O)OC)OC
• InChI: InChI=1S/C16H14O7/c1-20-14-11(19)9-10(18)7-5-4-6-8(17)12(7)23-13(9)15(21-2)16(14)22-3/h4-6,17,19H,1-3H3
• InChI Key: YXCUBCSFRXZFSG-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): 94.50 Ų
• XlogP: 2.70
• 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	+	0.9617	96.17%
Caco-2	+	0.6460	64.60%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7093	70.93%
OATP2B1 inhibitior	-	0.7116	71.16%
OATP1B1 inhibitior	+	0.9439	94.39%
OATP1B3 inhibitior	+	0.9698	96.98%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6686	66.86%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8682	86.82%
CYP3A4 substrate	+	0.5321	53.21%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.7782	77.82%
CYP2C9 inhibition	-	0.9325	93.25%
CYP2C19 inhibition	-	0.5514	55.14%
CYP2D6 inhibition	-	0.7363	73.63%
CYP1A2 inhibition	+	0.9561	95.61%
CYP2C8 inhibition	-	0.6381	63.81%
CYP inhibitory promiscuity	+	0.5753	57.53%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6097	60.97%
Eye corrosion	-	0.9746	97.46%
Eye irritation	+	0.8143	81.43%
Skin irritation	-	0.6975	69.75%
Skin corrosion	-	0.9788	97.88%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6629	66.29%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.9328	93.28%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7826	78.26%
Acute Oral Toxicity (c)	II	0.4834	48.34%
Estrogen receptor binding	+	0.6437	64.37%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6856	68.56%
Glucocorticoid receptor binding	+	0.7820	78.20%
Aromatase binding	+	0.5677	56.77%
PPAR gamma	+	0.7144	71.44%
Honey bee toxicity	-	0.9101	91.01%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8676	86.76%

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	97.51%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	96.43%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.24%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.13%	94.00%
CHEMBL2581	P07339	Cathepsin D	92.59%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.40%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.64%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	91.44%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.34%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	89.40%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.48%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.74%	86.33%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.42%	93.65%
CHEMBL2535	P11166	Glucose transporter	83.38%	98.75%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	82.89%	98.11%

Plants that contains it

• Halenia elliptica

Cross-Links

• PubChem: 162893843
• LOTUS: LTS0054013
• wikiData: Q105367503