2,3,6,8-tetrahydroxy-1-[(2R)-2-hydroxy-3-methylbut-3-enyl]xanthen-9-one

Details

• Internal ID: f7979106-ba21-4008-8ed5-704245643c15
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 8-prenylated xanthones
• IUPAC Name: 2,3,6,8-tetrahydroxy-1-[(2R)-2-hydroxy-3-methylbut-3-enyl]xanthen-9-one
• SMILES (Canonical): CC(=C)C(CC1=C(C(=CC2=C1C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O
• SMILES (Isomeric): CC(=C)[C@@H](CC1=C(C(=CC2=C1C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O
• InChI: InChI=1S/C18H16O7/c1-7(2)10(20)5-9-15-14(6-12(22)17(9)23)25-13-4-8(19)3-11(21)16(13)18(15)24/h3-4,6,10,19-23H,1,5H2,2H3/t10-/m1/s1
• InChI Key: GONMHOQVFDWXLV-SNVBAGLBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₇
• Molecular Weight: 344.30 g/mol
• Exact Mass: 344.08960285 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.25
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9295	92.95%
Caco-2	-	0.5830	58.30%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.4343	43.43%
OATP2B1 inhibitior	-	0.5497	54.97%
OATP1B1 inhibitior	+	0.7878	78.78%
OATP1B3 inhibitior	+	0.9823	98.23%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8984	89.84%
P-glycoprotein inhibitior	-	0.8777	87.77%
P-glycoprotein substrate	-	0.7120	71.20%
CYP3A4 substrate	+	0.5264	52.64%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8244	82.44%
CYP3A4 inhibition	-	0.6651	66.51%
CYP2C9 inhibition	-	0.6537	65.37%
CYP2C19 inhibition	-	0.6495	64.95%
CYP2D6 inhibition	-	0.7039	70.39%
CYP1A2 inhibition	+	0.5508	55.08%
CYP2C8 inhibition	+	0.5253	52.53%
CYP inhibitory promiscuity	-	0.5355	53.55%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6742	67.42%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.5687	56.87%
Skin irritation	-	0.6663	66.63%
Skin corrosion	-	0.8939	89.39%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6065	60.65%
Micronuclear	+	0.5718	57.18%
Hepatotoxicity	+	0.5328	53.28%
skin sensitisation	-	0.6712	67.12%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7743	77.43%
Acute Oral Toxicity (c)	III	0.3737	37.37%
Estrogen receptor binding	+	0.6910	69.10%
Androgen receptor binding	+	0.7087	70.87%
Thyroid receptor binding	+	0.5547	55.47%
Glucocorticoid receptor binding	+	0.8132	81.32%
Aromatase binding	+	0.5923	59.23%
PPAR gamma	+	0.7954	79.54%
Honey bee toxicity	-	0.8732	87.32%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9804	98.04%

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	99.02%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.14%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.44%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.04%	94.73%
CHEMBL1929	P47989	Xanthine dehydrogenase	88.43%	96.12%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.87%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.67%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.95%	95.56%
CHEMBL3194	P02766	Transthyretin	84.12%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.53%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.50%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	81.88%	91.49%

Plants that contains it

• Hypericum scabrum

Cross-Links

• PubChem: 162914967
• LOTUS: LTS0200740
• wikiData: Q105014276