2,6,8-Trihydroxy-1-(3-methylbut-2-enyl)xanthen-9-one

Details

• Internal ID: 77aaa857-c9b9-4bac-a745-b76578d852a8
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 8-prenylated xanthones
• IUPAC Name: 2,6,8-trihydroxy-1-(3-methylbut-2-enyl)xanthen-9-one
• SMILES (Canonical): CC(=CCC1=C(C=CC2=C1C(=O)C3=C(C=C(C=C3O2)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC2=C1C(=O)C3=C(C=C(C=C3O2)O)O)O)C
• InChI: InChI=1S/C18H16O5/c1-9(2)3-4-11-12(20)5-6-14-16(11)18(22)17-13(21)7-10(19)8-15(17)23-14/h3,5-8,19-21H,4H2,1-2H3
• InChI Key: QFVPVZIXCWJODC-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₅
• Molecular Weight: 312.30 g/mol
• Exact Mass: 312.09977361 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 3.57
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 2,6,8-Trihydroxy-1-(3-methylbut-2-enyl)-9H-xanthen-9-one
• 2,6,8-trihydroxy-1-(3-methylbut-2-en-1-yl)-9h-xanthen-9-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9892	98.92%
Caco-2	+	0.8561	85.61%
Blood Brain Barrier	-	0.5379	53.79%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6949	69.49%
OATP2B1 inhibitior	-	0.5578	55.78%
OATP1B1 inhibitior	+	0.8703	87.03%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5590	55.90%
P-glycoprotein inhibitior	-	0.7580	75.80%
P-glycoprotein substrate	-	0.8526	85.26%
CYP3A4 substrate	-	0.5189	51.89%
CYP2C9 substrate	-	0.5755	57.55%
CYP2D6 substrate	-	0.8328	83.28%
CYP3A4 inhibition	+	0.5634	56.34%
CYP2C9 inhibition	+	0.9158	91.58%
CYP2C19 inhibition	+	0.9038	90.38%
CYP2D6 inhibition	-	0.5907	59.07%
CYP1A2 inhibition	+	0.9441	94.41%
CYP2C8 inhibition	+	0.4516	45.16%
CYP inhibitory promiscuity	+	0.9296	92.96%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7173	71.73%
Eye corrosion	-	0.9890	98.90%
Eye irritation	+	0.7242	72.42%
Skin irritation	-	0.6876	68.76%
Skin corrosion	-	0.9087	90.87%
Ames mutagenesis	+	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6536	65.36%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	+	0.5303	53.03%
skin sensitisation	-	0.6264	62.64%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6331	63.31%
Acute Oral Toxicity (c)	III	0.6473	64.73%
Estrogen receptor binding	+	0.9133	91.33%
Androgen receptor binding	+	0.8406	84.06%
Thyroid receptor binding	+	0.5912	59.12%
Glucocorticoid receptor binding	+	0.9118	91.18%
Aromatase binding	+	0.7659	76.59%
PPAR gamma	+	0.9339	93.39%
Honey bee toxicity	-	0.9054	90.54%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9929	99.29%

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	98.92%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	95.28%	94.73%
CHEMBL2581	P07339	Cathepsin D	95.24%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	94.95%	91.49%
CHEMBL1929	P47989	Xanthine dehydrogenase	94.66%	96.12%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.40%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.23%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.41%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.86%	95.56%
CHEMBL3038469	P24941	CDK2/Cyclin A	88.14%	91.38%
CHEMBL3194	P02766	Transthyretin	88.08%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.25%	99.17%
CHEMBL4208	P20618	Proteasome component C5	80.67%	90.00%

Plants that contains it

• Hypericum ellipticum

Cross-Links

• PubChem: 5493673
• LOTUS: LTS0150864
• wikiData: Q105219806