4-Hydroxy-1,2-dimethoxyxanthone

Details

• Internal ID: c0415500-dd0f-4b03-a30b-13e68ce4530f
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 4-hydroxy-1,2-dimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C2=C(C(=C1)O)OC3=CC=CC=C3C2=O)OC
• SMILES (Isomeric): COC1=C(C2=C(C(=C1)O)OC3=CC=CC=C3C2=O)OC
• InChI: InChI=1S/C15H12O5/c1-18-11-7-9(16)14-12(15(11)19-2)13(17)8-5-3-4-6-10(8)20-14/h3-7,16H,1-2H3
• InChI Key: WUUDTDARGCSROI-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.25 g/mol
• Exact Mass: 272.06847348 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.67
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 4-Hydroxy-1,2-dimethoxyxanthone
• BDBM50485135

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9791	97.91%
Caco-2	+	0.6950	69.50%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7024	70.24%
OATP2B1 inhibitior	-	0.8642	86.42%
OATP1B1 inhibitior	+	0.9324	93.24%
OATP1B3 inhibitior	+	0.9932	99.32%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6030	60.30%
P-glycoprotein inhibitior	-	0.4452	44.52%
P-glycoprotein substrate	-	0.8643	86.43%
CYP3A4 substrate	+	0.5488	54.88%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	+	0.5215	52.15%
CYP2C9 inhibition	-	0.8938	89.38%
CYP2C19 inhibition	+	0.6902	69.02%
CYP2D6 inhibition	-	0.7703	77.03%
CYP1A2 inhibition	+	0.9595	95.95%
CYP2C8 inhibition	+	0.4530	45.30%
CYP inhibitory promiscuity	+	0.5264	52.64%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6210	62.10%
Eye corrosion	-	0.9551	95.51%
Eye irritation	+	0.8731	87.31%
Skin irritation	-	0.5807	58.07%
Skin corrosion	-	0.9822	98.22%
Ames mutagenesis	+	0.7036	70.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.6534	65.34%
Micronuclear	+	0.8959	89.59%
Hepatotoxicity	+	0.5322	53.22%
skin sensitisation	-	0.9125	91.25%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6605	66.05%
Acute Oral Toxicity (c)	III	0.4994	49.94%
Estrogen receptor binding	+	0.7891	78.91%
Androgen receptor binding	+	0.7106	71.06%
Thyroid receptor binding	+	0.6933	69.33%
Glucocorticoid receptor binding	+	0.8934	89.34%
Aromatase binding	+	0.8174	81.74%
PPAR gamma	+	0.8026	80.26%
Honey bee toxicity	-	0.8645	86.45%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5951	59.51%
Fish aquatic toxicity	+	0.8492	84.92%

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	99.13%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.29%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.71%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.98%	89.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.57%	93.99%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.87%	99.23%
CHEMBL2535	P11166	Glucose transporter	91.70%	98.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.28%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.00%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.50%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.18%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	83.89%	94.73%
CHEMBL1255126	O15151	Protein Mdm4	82.36%	90.20%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.91%	93.65%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.76%	80.78%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.79%	92.62%

Plants that contains it

• Hypericum geminiflorum

Cross-Links

• PubChem: 54450736
• LOTUS: LTS0002475
• wikiData: Q105313302