3,6-Dihydroxy-1,2-dimethoxyxanthone

Details

• Internal ID: a0a7643b-587d-4aad-9057-a69ecc99188f
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 3,6-dihydroxy-1,2-dimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C2=C(C=C1O)OC3=C(C2=O)C=CC(=C3)O)OC
• SMILES (Isomeric): COC1=C(C2=C(C=C1O)OC3=C(C2=O)C=CC(=C3)O)OC
• InChI: InChI=1S/C15H12O6/c1-19-14-9(17)6-11-12(15(14)20-2)13(18)8-4-3-7(16)5-10(8)21-11/h3-6,16-17H,1-2H3
• InChI Key: KREQTBSQJOEUKA-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₆
• Molecular Weight: 288.25 g/mol
• Exact Mass: 288.06338810 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• BDBM50485138
• 3,6-dihydroxy-1,2-dimethoxyxanthone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9642	96.42%
Caco-2	+	0.7345	73.45%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7364	73.64%
OATP2B1 inhibitior	-	0.7118	71.18%
OATP1B1 inhibitior	+	0.9162	91.62%
OATP1B3 inhibitior	+	0.9851	98.51%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8446	84.46%
P-glycoprotein inhibitior	-	0.7245	72.45%
P-glycoprotein substrate	-	0.7435	74.35%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
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	+	0.4591	45.91%
CYP inhibitory promiscuity	+	0.6446	64.46%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6331	63.31%
Eye corrosion	-	0.9655	96.55%
Eye irritation	+	0.8619	86.19%
Skin irritation	-	0.6099	60.99%
Skin corrosion	-	0.9698	96.98%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6088	60.88%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.5822	58.22%
skin sensitisation	-	0.9149	91.49%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8050	80.50%
Acute Oral Toxicity (c)	III	0.5708	57.08%
Estrogen receptor binding	+	0.8164	81.64%
Androgen receptor binding	+	0.8126	81.26%
Thyroid receptor binding	+	0.6203	62.03%
Glucocorticoid receptor binding	+	0.8870	88.70%
Aromatase binding	+	0.7772	77.72%
PPAR gamma	+	0.6668	66.68%
Honey bee toxicity	-	0.8974	89.74%
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	98.41%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.20%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.99%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.99%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.63%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.49%	93.99%
CHEMBL2581	P07339	Cathepsin D	90.20%	98.95%
CHEMBL242	Q92731	Estrogen receptor beta	86.52%	98.35%
CHEMBL2535	P11166	Glucose transporter	86.30%	98.75%
CHEMBL3194	P02766	Transthyretin	85.96%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.06%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.99%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.42%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.66%	99.23%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.20%	80.78%

Plants that contains it

• Cratoxylum cochinchinense

Cross-Links

• PubChem: 16105269
• LOTUS: LTS0194890
• wikiData: Q105144953