2,8-Dihydroxy-1-methoxyxanthone

Details

• Internal ID: be526d62-1a2d-4f56-9703-64617bc6f348
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 2,8-dihydroxy-1-methoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C=CC2=C1C(=O)C3=C(C=CC=C3O2)O)O
• SMILES (Isomeric): COC1=C(C=CC2=C1C(=O)C3=C(C=CC=C3O2)O)O
• InChI: InChI=1S/C14H10O5/c1-18-14-8(16)5-6-10-12(14)13(17)11-7(15)3-2-4-9(11)19-10/h2-6,15-16H,1H3
• InChI Key: HMNUZPXEMGNMTG-UHFFFAOYSA-N
• Popularity: 6 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: 2.80
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 1,7-Dihydroxy-8-methoxyxanthon
• CHEMBL1170235
• 2,8-dihydroxy-1-methoxyxanthone
• 1,7-Dihydroxy-8-methoxyxanthone
• NSC-661740
• 2,8-dihydroxy-1-methoxy-xanthen-9-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	+	0.5238	52.38%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7377	73.77%
OATP2B1 inhibitior	-	0.7135	71.35%
OATP1B1 inhibitior	+	0.9358	93.58%
OATP1B3 inhibitior	+	0.9934	99.34%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7899	78.99%
P-glycoprotein inhibitior	-	0.6484	64.84%
P-glycoprotein substrate	-	0.9555	95.55%
CYP3A4 substrate	-	0.5427	54.27%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
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	-	0.7544	75.44%
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	+	0.7977	79.77%
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	-	0.7256	72.56%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.9205	92.05%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.4548	45.48%
Acute Oral Toxicity (c)	III	0.8197	81.97%
Estrogen receptor binding	+	0.8464	84.64%
Androgen receptor binding	+	0.5873	58.73%
Thyroid receptor binding	+	0.6655	66.55%
Glucocorticoid receptor binding	+	0.8156	81.56%
Aromatase binding	+	0.8443	84.43%
PPAR gamma	+	0.7395	73.95%
Honey bee toxicity	-	0.9487	94.87%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
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	96.42%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.07%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.98%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.94%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.92%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.19%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.89%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.03%	94.45%
CHEMBL2535	P11166	Glucose transporter	85.75%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.89%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	84.67%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.98%	99.15%

Plants that contains it

• Bonnetia paniculata
• Calophyllum calaba
• Calophyllum teysmannii
• Cratoxylum formosum
• Cratoxylum maingayi
• Haploclathra leiantha
• Haploclathra paniculata
• Kielmeyera excelsa

Cross-Links

• PubChem: 5464640
• LOTUS: LTS0058413
• wikiData: Q104168003