1-Hydroxyxanthone

Details

• Internal ID: 2a0d681f-3acb-430f-91f3-4ad235551954
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1-hydroxyxanthen-9-one
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)C3=C(C=CC=C3O2)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)C3=C(C=CC=C3O2)O
• InChI: InChI=1S/C13H8O3/c14-9-5-3-7-11-12(9)13(15)8-4-1-2-6-10(8)16-11/h1-7,14H
• InChI Key: BNLRKUSVMCIOGU-UHFFFAOYSA-N
• Popularity: 69 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₈O₃
• Molecular Weight: 212.20 g/mol
• Exact Mass: 212.047344113 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 2.65
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 719-41-5
• 1-hydroxyxanthen-9-one
• 1-Hydroxy-9H-xanthen-9-one
• 9H-Xanthen-9-one, 1-hydroxy-
• CHEMBL187368
• hydroxyxanthone
• Xanthen-9-one, 1-hydroxy-
• 1-Hydroxy-xanthen-9-one
• SCHEMBL873750
• 1-Hydroxy-9H-xanthen-9-one #
• DTXSID30222157
• BNLRKUSVMCIOGU-UHFFFAOYSA-N
• BDBM50155415
• XH161861
• InChI=1/C13H8O3/c14-9-5-3-7-11-12(9)13(15)8-4-1-2-6-10(8)16-11/h1-7,14

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9955	99.55%
Caco-2	+	0.7535	75.35%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6018	60.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9149	91.49%
OATP1B3 inhibitior	+	0.9938	99.38%
MATE1 inhibitior	-	0.5200	52.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8138	81.38%
P-glycoprotein inhibitior	-	0.8618	86.18%
P-glycoprotein substrate	-	0.9389	93.89%
CYP3A4 substrate	-	0.5554	55.54%
CYP2C9 substrate	-	0.6265	62.65%
CYP2D6 substrate	-	0.8495	84.95%
CYP3A4 inhibition	-	0.6607	66.07%
CYP2C9 inhibition	-	0.7608	76.08%
CYP2C19 inhibition	+	0.6440	64.40%
CYP2D6 inhibition	-	0.9207	92.07%
CYP1A2 inhibition	+	0.9767	97.67%
CYP2C8 inhibition	-	0.8504	85.04%
CYP inhibitory promiscuity	-	0.7610	76.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9313	93.13%
Carcinogenicity (trinary)	Non-required	0.4615	46.15%
Eye corrosion	-	0.9269	92.69%
Eye irritation	+	0.9654	96.54%
Skin irritation	+	0.7953	79.53%
Skin corrosion	-	0.9929	99.29%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8782	87.82%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.7677	76.77%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.5283	52.83%
Acute Oral Toxicity (c)	III	0.6975	69.75%
Estrogen receptor binding	+	0.8819	88.19%
Androgen receptor binding	+	0.6169	61.69%
Thyroid receptor binding	+	0.7373	73.73%
Glucocorticoid receptor binding	+	0.8617	86.17%
Aromatase binding	+	0.8786	87.86%
PPAR gamma	+	0.9034	90.34%
Honey bee toxicity	-	0.9442	94.42%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.7626	76.26%

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	96.56%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.01%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.97%	93.99%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.94%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.49%	89.00%
CHEMBL2581	P07339	Cathepsin D	90.92%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	88.54%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.39%	94.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.22%	93.65%

Plants that contains it

• Hedychium gardnerianum
• Hypericum beanii
• Hypericum geminiflorum
• Hypericum henryi
• Rhachidosorus mesosorus

Cross-Links

• PubChem: 5376036
• LOTUS: LTS0191503
• wikiData: Q83100326