2,5-Dihydroxyxanthone

Details

• Internal ID: 0a73f5b6-8b65-4b74-a2c2-64182c122d6f
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 2,5-dihydroxyxanthen-9-one
• SMILES (Canonical): C1=CC2=C(C(=C1)O)OC3=C(C2=O)C=C(C=C3)O
• SMILES (Isomeric): C1=CC2=C(C(=C1)O)OC3=C(C2=O)C=C(C=C3)O
• InChI: InChI=1S/C13H8O4/c14-7-4-5-11-9(6-7)12(16)8-2-1-3-10(15)13(8)17-11/h1-6,14-15H
• InChI Key: LXSIVSWCSPREMS-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₈O₄
• Molecular Weight: 228.20 g/mol
• Exact Mass: 228.04225873 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.36
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 35040-32-5
• 2,5-dihydroxyxanthen-9-one
• 2,5-Dihydroxy-9H-xanthen-9-one
• 4,7-Dihydroxyxanthon
• CHEMBL4061540
• DTXSID20188551
• 9H-Xanthen-9-one, 2,5-dihydroxy-
• AKOS040760993

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9717	97.17%
Caco-2	-	0.7100	71.00%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6458	64.58%
OATP2B1 inhibitior	-	0.7115	71.15%
OATP1B1 inhibitior	+	0.8967	89.67%
OATP1B3 inhibitior	+	0.9836	98.36%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8901	89.01%
P-glycoprotein inhibitior	-	0.8869	88.69%
P-glycoprotein substrate	-	0.8923	89.23%
CYP3A4 substrate	-	0.5231	52.31%
CYP2C9 substrate	-	0.8238	82.38%
CYP2D6 substrate	-	0.8051	80.51%
CYP3A4 inhibition	+	0.5297	52.97%
CYP2C9 inhibition	+	0.5447	54.47%
CYP2C19 inhibition	-	0.6827	68.27%
CYP2D6 inhibition	-	0.9006	90.06%
CYP1A2 inhibition	+	0.9448	94.48%
CYP2C8 inhibition	-	0.6360	63.60%
CYP inhibitory promiscuity	-	0.6121	61.21%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5084	50.84%
Eye corrosion	-	0.9693	96.93%
Eye irritation	+	0.9386	93.86%
Skin irritation	+	0.6448	64.48%
Skin corrosion	-	0.9838	98.38%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8915	89.15%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8100	81.00%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7829	78.29%
Acute Oral Toxicity (c)	III	0.6516	65.16%
Estrogen receptor binding	+	0.6664	66.64%
Androgen receptor binding	+	0.8522	85.22%
Thyroid receptor binding	+	0.6358	63.58%
Glucocorticoid receptor binding	+	0.8400	84.00%
Aromatase binding	+	0.7559	75.59%
PPAR gamma	+	0.8421	84.21%
Honey bee toxicity	-	0.8902	89.02%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.7742	77.42%

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	98.39%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.52%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.82%	99.23%
CHEMBL2581	P07339	Cathepsin D	93.29%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.46%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	89.88%	94.73%
CHEMBL2535	P11166	Glucose transporter	89.45%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.21%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.52%	99.15%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.03%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.65%	94.45%
CHEMBL3194	P02766	Transthyretin	80.42%	90.71%

Plants that contains it

• Cratoxylum cochinchinense
• Hypericum beanii
• Hypericum henryi

Cross-Links

• PubChem: 182216
• LOTUS: LTS0075826
• wikiData: Q105251740