3-Hydroxy-1,5,6-trimethoxyxanthen-9-one

Details

• Internal ID: 615a2997-d94c-499e-9404-ce1fce846772
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 3-hydroxy-1,5,6-trimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C(C2=C(C=C1)C(=O)C3=C(O2)C=C(C=C3OC)O)OC
• SMILES (Isomeric): COC1=C(C2=C(C=C1)C(=O)C3=C(O2)C=C(C=C3OC)O)OC
• InChI: InChI=1S/C16H14O6/c1-19-10-5-4-9-14(18)13-11(20-2)6-8(17)7-12(13)22-15(9)16(10)21-3/h4-7,17H,1-3H3
• InChI Key: DAPPJIWHYPGZBD-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₆
• Molecular Weight: 302.28 g/mol
• Exact Mass: 302.07903816 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.68
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9769	97.69%
Caco-2	+	0.7781	77.81%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6863	68.63%
OATP2B1 inhibitior	-	0.7223	72.23%
OATP1B1 inhibitior	+	0.9436	94.36%
OATP1B3 inhibitior	+	0.9884	98.84%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5647	56.47%
P-glycoprotein inhibitior	-	0.4660	46.60%
P-glycoprotein substrate	-	0.8008	80.08%
CYP3A4 substrate	+	0.5201	52.01%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	-	0.6511	65.11%
CYP2C9 inhibition	-	0.9806	98.06%
CYP2C19 inhibition	-	0.6277	62.77%
CYP2D6 inhibition	-	0.8588	85.88%
CYP1A2 inhibition	+	0.9585	95.85%
CYP2C8 inhibition	+	0.6297	62.97%
CYP inhibitory promiscuity	-	0.5523	55.23%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6004	60.04%
Eye corrosion	-	0.9679	96.79%
Eye irritation	+	0.8737	87.37%
Skin irritation	-	0.6803	68.03%
Skin corrosion	-	0.9860	98.60%
Ames mutagenesis	+	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5774	57.74%
Micronuclear	+	0.8359	83.59%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.9331	93.31%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6426	64.26%
Acute Oral Toxicity (c)	II	0.5755	57.55%
Estrogen receptor binding	+	0.8693	86.93%
Androgen receptor binding	+	0.8052	80.52%
Thyroid receptor binding	+	0.6793	67.93%
Glucocorticoid receptor binding	+	0.8440	84.40%
Aromatase binding	+	0.8394	83.94%
PPAR gamma	+	0.7203	72.03%
Honey bee toxicity	-	0.8874	88.74%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5249	52.49%
Fish aquatic toxicity	+	0.8585	85.85%

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	97.06%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.23%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.41%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.35%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.87%	89.00%
CHEMBL2535	P11166	Glucose transporter	90.53%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.41%	86.33%
CHEMBL3194	P02766	Transthyretin	87.70%	90.71%
CHEMBL4040	P28482	MAP kinase ERK2	86.84%	83.82%
CHEMBL2581	P07339	Cathepsin D	86.76%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.98%	93.99%
CHEMBL1255126	O15151	Protein Mdm4	85.85%	90.20%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.61%	99.23%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.28%	80.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.81%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	80.38%	91.49%

Plants that contains it

• Haploclathra leiantha
• Kielmeyera rupestris

Cross-Links

• PubChem: 15910546
• LOTUS: LTS0097903
• wikiData: Q104973825