3,6-Dihydroxy-1,5,7-trimethoxyxanthone

Details

• Internal ID: ce3c5b88-cc53-4e97-aabd-86191f4aa34b
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 3,6-dihydroxy-1,5,7-trimethoxyxanthen-9-one
• SMILES (Canonical): COC1=CC(=CC2=C1C(=O)C3=CC(=C(C(=C3O2)OC)O)OC)O
• SMILES (Isomeric): COC1=CC(=CC2=C1C(=O)C3=CC(=C(C(=C3O2)OC)O)OC)O
• InChI: InChI=1S/C16H14O7/c1-20-9-4-7(17)5-10-12(9)13(18)8-6-11(21-2)14(19)16(22-3)15(8)23-10/h4-6,17,19H,1-3H3
• InChI Key: QLHNHLVUYKOUKI-UHFFFAOYSA-N
• Popularity: 4 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): 94.50 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	+	0.9617	96.17%
Caco-2	+	0.5590	55.90%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7093	70.93%
OATP2B1 inhibitior	-	0.5738	57.38%
OATP1B1 inhibitior	+	0.8958	89.58%
OATP1B3 inhibitior	+	0.9698	96.98%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6922	69.22%
P-glycoprotein inhibitior	-	0.5405	54.05%
P-glycoprotein substrate	-	0.8040	80.40%
CYP3A4 substrate	+	0.5347	53.47%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
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	+	0.5475	54.75%
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	+	0.8813	88.13%
Skin irritation	-	0.6975	69.75%
Skin corrosion	-	0.9788	97.88%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6234	62.34%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.9328	93.28%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8328	83.28%
Acute Oral Toxicity (c)	II	0.4834	48.34%
Estrogen receptor binding	+	0.8714	87.14%
Androgen receptor binding	+	0.6826	68.26%
Thyroid receptor binding	+	0.6636	66.36%
Glucocorticoid receptor binding	+	0.8727	87.27%
Aromatase binding	+	0.7269	72.69%
PPAR gamma	+	0.7255	72.55%
Honey bee toxicity	-	0.8497	84.97%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
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	98.90%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.50%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.69%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.15%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.77%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.22%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.44%	99.23%
CHEMBL2535	P11166	Glucose transporter	86.18%	98.75%
CHEMBL2581	P07339	Cathepsin D	85.25%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.73%	99.17%
CHEMBL3194	P02766	Transthyretin	84.69%	90.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.17%	92.94%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	82.39%	98.11%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.41%	92.62%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	80.28%	98.21%

Plants that contains it

• Hypericum geminiflorum

Cross-Links

• PubChem: 91205255
• LOTUS: LTS0170226
• wikiData: Q105223584