2,6,8-Trihydroxy-1-(3-hydroxy-3-methylbutyl)xanthen-9-one

Details

• Internal ID: 1617e93d-70fa-4f26-bf99-497fec01182b
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 8-prenylated xanthones
• IUPAC Name: 2,6,8-trihydroxy-1-(3-hydroxy-3-methylbutyl)xanthen-9-one
• SMILES (Canonical): CC(C)(CCC1=C(C=CC2=C1C(=O)C3=C(C=C(C=C3O2)O)O)O)O
• SMILES (Isomeric): CC(C)(CCC1=C(C=CC2=C1C(=O)C3=C(C=C(C=C3O2)O)O)O)O
• InChI: InChI=1S/C18H18O6/c1-18(2,23)6-5-10-11(20)3-4-13-15(10)17(22)16-12(21)7-9(19)8-14(16)24-13/h3-4,7-8,19-21,23H,5-6H2,1-2H3
• InChI Key: HBLDDRXQYPHQQU-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈O₆
• Molecular Weight: 330.30 g/mol
• Exact Mass: 330.11033829 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.77
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9667	96.67%
Caco-2	+	0.6621	66.21%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7255	72.55%
OATP2B1 inhibitior	+	0.5753	57.53%
OATP1B1 inhibitior	+	0.8137	81.37%
OATP1B3 inhibitior	+	0.9579	95.79%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7879	78.79%
P-glycoprotein inhibitior	-	0.8107	81.07%
P-glycoprotein substrate	-	0.7618	76.18%
CYP3A4 substrate	+	0.5084	50.84%
CYP2C9 substrate	-	0.5797	57.97%
CYP2D6 substrate	-	0.8350	83.50%
CYP3A4 inhibition	+	0.5957	59.57%
CYP2C9 inhibition	-	0.7539	75.39%
CYP2C19 inhibition	-	0.7851	78.51%
CYP2D6 inhibition	-	0.8086	80.86%
CYP1A2 inhibition	+	0.6440	64.40%
CYP2C8 inhibition	+	0.6424	64.24%
CYP inhibitory promiscuity	-	0.7343	73.43%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6906	69.06%
Eye corrosion	-	0.9916	99.16%
Eye irritation	+	0.6397	63.97%
Skin irritation	-	0.7066	70.66%
Skin corrosion	-	0.8736	87.36%
Ames mutagenesis	+	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4593	45.93%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8154	81.54%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7846	78.46%
Acute Oral Toxicity (c)	III	0.6031	60.31%
Estrogen receptor binding	+	0.8806	88.06%
Androgen receptor binding	+	0.8501	85.01%
Thyroid receptor binding	+	0.5647	56.47%
Glucocorticoid receptor binding	+	0.9277	92.77%
Aromatase binding	+	0.7850	78.50%
PPAR gamma	+	0.9463	94.63%
Honey bee toxicity	-	0.9123	91.23%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9473	94.73%

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	98.02%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.08%	98.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	94.70%	96.12%
CHEMBL3401	O75469	Pregnane X receptor	94.03%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.72%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.33%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.59%	95.56%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	87.49%	93.65%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.67%	94.00%
CHEMBL3194	P02766	Transthyretin	85.33%	90.71%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.47%	93.99%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.54%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.17%	80.78%
CHEMBL4208	P20618	Proteasome component C5	80.38%	90.00%

Plants that contains it

• Garcinia nigrolineata

Cross-Links

• PubChem: 21576569
• LOTUS: LTS0151883
• wikiData: Q105025360