1,2,5-Trihydroxyxanthone

Details

• Internal ID: 0bbb80be-fd10-4451-a151-80aa7be9e670
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,2,5-trihydroxyxanthen-9-one
• SMILES (Canonical): C1=CC2=C(C(=C1)O)OC3=C(C2=O)C(=C(C=C3)O)O
• SMILES (Isomeric): C1=CC2=C(C(=C1)O)OC3=C(C2=O)C(=C(C=C3)O)O
• InChI: InChI=1S/C13H8O5/c14-7-4-5-9-10(12(7)17)11(16)6-2-1-3-8(15)13(6)18-9/h1-5,14-15,17H
• InChI Key: WRYMABXVDKBFIK-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₈O₅
• Molecular Weight: 244.20 g/mol
• Exact Mass: 244.03717335 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.06
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• 156640-23-2
• 1,2,5-trihydroxyxanthen-9-one
• 1,2,5-trihydroxy-9H-xanthen-9-one
• 9H-Xanthen-9-one, 1,2,5-trihydroxy-
• starbld0026808
• CHEMBL4209205
• CHEBI:66268
• DTXSID901300020
• AKOS040760863
• Q27134811

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9438	94.38%
Caco-2	-	0.8767	87.67%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7026	70.26%
OATP2B1 inhibitior	-	0.6752	67.52%
OATP1B1 inhibitior	+	0.9374	93.74%
OATP1B3 inhibitior	+	0.9936	99.36%
MATE1 inhibitior	-	0.5000	50.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8479	84.79%
P-glycoprotein inhibitior	-	0.8899	88.99%
P-glycoprotein substrate	-	0.9466	94.66%
CYP3A4 substrate	-	0.5641	56.41%
CYP2C9 substrate	-	0.6803	68.03%
CYP2D6 substrate	-	0.8540	85.40%
CYP3A4 inhibition	-	0.7624	76.24%
CYP2C9 inhibition	-	0.5560	55.60%
CYP2C19 inhibition	-	0.8199	81.99%
CYP2D6 inhibition	-	0.8877	88.77%
CYP1A2 inhibition	+	0.9683	96.83%
CYP2C8 inhibition	-	0.8121	81.21%
CYP inhibitory promiscuity	-	0.6892	68.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5787	57.87%
Eye corrosion	-	0.9831	98.31%
Eye irritation	+	0.9432	94.32%
Skin irritation	+	0.6757	67.57%
Skin corrosion	-	0.9607	96.07%
Ames mutagenesis	+	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8741	87.41%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.6642	66.42%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8193	81.93%
Acute Oral Toxicity (c)	II	0.5564	55.64%
Estrogen receptor binding	+	0.7322	73.22%
Androgen receptor binding	+	0.6695	66.95%
Thyroid receptor binding	+	0.6558	65.58%
Glucocorticoid receptor binding	+	0.9083	90.83%
Aromatase binding	+	0.7547	75.47%
PPAR gamma	+	0.8504	85.04%
Honey bee toxicity	-	0.9252	92.52%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9101	91.01%

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	98.61%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.36%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.82%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	94.51%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.20%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.70%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.23%	93.99%
CHEMBL2581	P07339	Cathepsin D	88.64%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	88.54%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.53%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.66%	94.45%

Plants that contains it

• Garcinia subelliptica
• Hypericum beanii
• Hypericum henryi
• Hypericum monogynum

Cross-Links

• PubChem: 10060362
• NPASS: NPC156481
• LOTUS: LTS0179616
• wikiData: Q27134811