3,4-Dihydroxy-2-methoxyxanthone

Details

• Internal ID: e8117b80-19fa-404e-94a4-c1c8b71456b7
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 3,4-dihydroxy-2-methoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)C(=O)C3=CC=CC=C3O2)O)O
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)C(=O)C3=CC=CC=C3O2)O)O
• InChI: InChI=1S/C14H10O5/c1-18-10-6-8-11(15)7-4-2-3-5-9(7)19-14(8)13(17)12(10)16/h2-6,16-17H,1H3
• InChI Key: QVBMBJBJZWDNSK-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: 2.20
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 6702-55-2
• 3,4-dihydroxy-2-methoxyxanthen-9-one
• 3,4-dihydroxy-2-methoxy-9H-xanthen-9-one
• starbld0019873
• CHEMBL3813706
• AKOS040761063

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9448	94.48%
Caco-2	-	0.5888	58.88%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7176	71.76%
OATP2B1 inhibitior	-	0.7105	71.05%
OATP1B1 inhibitior	+	0.8913	89.13%
OATP1B3 inhibitior	+	1.0000	100.00%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8212	82.12%
P-glycoprotein inhibitior	-	0.6392	63.92%
P-glycoprotein substrate	-	0.8215	82.15%
CYP3A4 substrate	+	0.5318	53.18%
CYP2C9 substrate	-	0.8397	83.97%
CYP2D6 substrate	-	0.7876	78.76%
CYP3A4 inhibition	-	0.7681	76.81%
CYP2C9 inhibition	-	0.8896	88.96%
CYP2C19 inhibition	-	0.5820	58.20%
CYP2D6 inhibition	-	0.8589	85.89%
CYP1A2 inhibition	+	0.9796	97.96%
CYP2C8 inhibition	-	0.5710	57.10%
CYP inhibitory promiscuity	-	0.5398	53.98%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5599	55.99%
Eye corrosion	-	0.9632	96.32%
Eye irritation	+	0.7980	79.80%
Skin irritation	-	0.5421	54.21%
Skin corrosion	-	0.9458	94.58%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7501	75.01%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8982	89.82%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7176	71.76%
Acute Oral Toxicity (c)	III	0.7485	74.85%
Estrogen receptor binding	+	0.8901	89.01%
Androgen receptor binding	+	0.7330	73.30%
Thyroid receptor binding	+	0.6227	62.27%
Glucocorticoid receptor binding	+	0.9405	94.05%
Aromatase binding	+	0.8817	88.17%
PPAR gamma	+	0.7523	75.23%
Honey bee toxicity	-	0.8901	89.01%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.8510	85.10%

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	99.52%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.70%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.37%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.15%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.94%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.61%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.91%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.59%	99.23%
CHEMBL2535	P11166	Glucose transporter	88.11%	98.75%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	86.73%	98.21%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.85%	92.62%
CHEMBL3401	O75469	Pregnane X receptor	84.75%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.41%	95.50%

Plants that contains it

• Cratoxylum cochinchinense
• Hypericum reflexum

Cross-Links

• PubChem: 10038117
• LOTUS: LTS0014704
• wikiData: Q105228548