2,5,7-Trihydroxy-1-methoxyxanthen-9-one

Details

• Internal ID: df426944-aa33-4ceb-805b-7e9a714cf2cb
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 2,5,7-trihydroxy-1-methoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C=CC2=C1C(=O)C3=C(O2)C(=CC(=C3)O)O)O
• SMILES (Isomeric): COC1=C(C=CC2=C1C(=O)C3=C(O2)C(=CC(=C3)O)O)O
• InChI: InChI=1S/C14H10O6/c1-19-14-8(16)2-3-10-11(14)12(18)7-4-6(15)5-9(17)13(7)20-10/h2-5,15-17H,1H3
• InChI Key: NRILZASOWLTOMQ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₀O₆
• Molecular Weight: 274.22 g/mol
• Exact Mass: 274.04773803 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.07
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9378	93.78%
Caco-2	-	0.6709	67.09%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5512	55.12%
OATP2B1 inhibitior	-	0.5693	56.93%
OATP1B1 inhibitior	+	0.9446	94.46%
OATP1B3 inhibitior	+	0.9758	97.58%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7732	77.32%
P-glycoprotein inhibitior	-	0.7561	75.61%
P-glycoprotein substrate	-	0.9313	93.13%
CYP3A4 substrate	-	0.5214	52.14%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	+	0.6321	63.21%
CYP2C9 inhibition	-	0.6549	65.49%
CYP2C19 inhibition	+	0.6923	69.23%
CYP2D6 inhibition	-	0.6476	64.76%
CYP1A2 inhibition	+	0.9724	97.24%
CYP2C8 inhibition	+	0.4443	44.43%
CYP inhibitory promiscuity	+	0.7640	76.40%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6276	62.76%
Eye corrosion	-	0.9630	96.30%
Eye irritation	+	0.8595	85.95%
Skin irritation	-	0.5358	53.58%
Skin corrosion	-	0.9315	93.15%
Ames mutagenesis	+	0.7436	74.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.7628	76.28%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8858	88.58%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7524	75.24%
Acute Oral Toxicity (c)	III	0.7996	79.96%
Estrogen receptor binding	+	0.7539	75.39%
Androgen receptor binding	+	0.7315	73.15%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.8506	85.06%
Aromatase binding	+	0.6753	67.53%
PPAR gamma	+	0.8541	85.41%
Honey bee toxicity	-	0.8388	83.88%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.7882	78.82%

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	98.84%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.51%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.36%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.55%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.47%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.42%	89.00%
CHEMBL2581	P07339	Cathepsin D	90.01%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.53%	99.15%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.65%	93.99%
CHEMBL2535	P11166	Glucose transporter	88.35%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.82%	86.33%
CHEMBL3194	P02766	Transthyretin	84.62%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.10%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.01%	80.78%
CHEMBL3401	O75469	Pregnane X receptor	80.83%	94.73%

Plants that contains it

• Lindera neesiana
• Maclura cochinchinensis

Cross-Links

• PubChem: 11579945
• LOTUS: LTS0096932
• wikiData: Q105184574