2,5-Dihydroxy-1-methoxyxanthone

Details

• Internal ID: 528eab7c-893d-429e-b014-91c0f833ed20
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 2,5-dihydroxy-1-methoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C=CC2=C1C(=O)C3=C(O2)C(=CC=C3)O)O
• SMILES (Isomeric): COC1=C(C=CC2=C1C(=O)C3=C(O2)C(=CC=C3)O)O
• InChI: InChI=1S/C14H10O5/c1-18-14-9(16)5-6-10-11(14)12(17)7-3-2-4-8(15)13(7)19-10/h2-6,15-16H,1H3
• InChI Key: AIXALMAGQFXNBO-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₀O₅
• Molecular Weight: 258.23 g/mol
• Exact Mass: 258.05282342 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 173220-32-1
• 2,5-dihydroxy-1-methoxyxanthen-9-one
• 2,5-dihydroxy-1-methoxy-9h-xanthen-9-one
• CHEMBL4204339
• AKOS040760992

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	-	0.6273	62.73%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7377	73.77%
OATP2B1 inhibitior	-	0.7131	71.31%
OATP1B1 inhibitior	+	0.9582	95.82%
OATP1B3 inhibitior	+	0.9934	99.34%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7133	71.33%
P-glycoprotein inhibitior	-	0.7262	72.62%
P-glycoprotein substrate	-	0.9336	93.36%
CYP3A4 substrate	+	0.5194	51.94%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	-	0.7181	71.81%
CYP2C9 inhibition	-	0.5805	58.05%
CYP2C19 inhibition	+	0.7909	79.09%
CYP2D6 inhibition	-	0.7438	74.38%
CYP1A2 inhibition	+	0.9811	98.11%
CYP2C8 inhibition	-	0.7268	72.68%
CYP inhibitory promiscuity	+	0.6572	65.72%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5675	56.75%
Eye corrosion	-	0.9577	95.77%
Eye irritation	+	0.8042	80.42%
Skin irritation	-	0.5200	52.00%
Skin corrosion	-	0.9642	96.42%
Ames mutagenesis	+	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7422	74.22%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.9205	92.05%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8078	80.78%
Acute Oral Toxicity (c)	III	0.8197	81.97%
Estrogen receptor binding	+	0.8091	80.91%
Androgen receptor binding	+	0.5714	57.14%
Thyroid receptor binding	-	0.4898	48.98%
Glucocorticoid receptor binding	+	0.8978	89.78%
Aromatase binding	+	0.7441	74.41%
PPAR gamma	+	0.7544	75.44%
Honey bee toxicity	-	0.9004	90.04%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.8258	82.58%

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	98.17%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.99%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.67%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.93%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.86%	94.00%
CHEMBL2581	P07339	Cathepsin D	90.44%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.20%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.06%	94.45%
CHEMBL2535	P11166	Glucose transporter	89.81%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.37%	99.15%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.02%	80.78%
CHEMBL3401	O75469	Pregnane X receptor	85.88%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.41%	86.33%
CHEMBL1907	P15144	Aminopeptidase N	82.91%	93.31%

Plants that contains it

• Cratoxylum cochinchinense
• Garcinia dulcis
• Garcinia subelliptica

Cross-Links

• PubChem: 10848779
• LOTUS: LTS0276127
• wikiData: Q104913013