12-[(2S)-2,3-dihydroxy-3-methylbutyl]-5,8,9-trihydroxy-7-[(E)-4-hydroxy-3-methylbut-2-enyl]-2,2-dimethylpyrano[3,2-b]xanthen-6-one

Details

• Internal ID: d2b9ae14-79bc-41dd-a5b3-4815888730ee
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 8-prenylated xanthones
• IUPAC Name: 12-[(2S)-2,3-dihydroxy-3-methylbutyl]-5,8,9-trihydroxy-7-[(E)-4-hydroxy-3-methylbut-2-enyl]-2,2-dimethylpyrano[3,2-b]xanthen-6-one
• SMILES (Canonical): CC(=CCC1=C(C(=CC2=C1C(=O)C3=C(O2)C(=C4C(=C3O)C=CC(O4)(C)C)CC(C(C)(C)O)O)O)O)CO
• SMILES (Isomeric): C/C(=C\CC1=C(C(=CC2=C1C(=O)C3=C(O2)C(=C4C(=C3O)C=CC(O4)(C)C)C[C@@H](C(C)(C)O)O)O)O)/CO
• InChI: InChI=1S/C28H32O9/c1-13(12-29)6-7-14-20-18(11-17(30)22(14)32)36-26-16(10-19(31)28(4,5)35)25-15(8-9-27(2,3)37-25)23(33)21(26)24(20)34/h6,8-9,11,19,29-33,35H,7,10,12H2,1-5H3/b13-6+/t19-/m0/s1
• InChI Key: WCAZWPKNYZBYGB-HBYKMFCXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₉
• Molecular Weight: 512.50 g/mol
• Exact Mass: 512.20463259 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.40
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9752	97.52%
Caco-2	-	0.7330	73.30%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7351	73.51%
OATP2B1 inhibitior	+	0.5735	57.35%
OATP1B1 inhibitior	+	0.8534	85.34%
OATP1B3 inhibitior	+	0.9522	95.22%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8521	85.21%
P-glycoprotein inhibitior	+	0.6865	68.65%
P-glycoprotein substrate	+	0.5835	58.35%
CYP3A4 substrate	+	0.6550	65.50%
CYP2C9 substrate	-	0.6100	61.00%
CYP2D6 substrate	-	0.8322	83.22%
CYP3A4 inhibition	-	0.7679	76.79%
CYP2C9 inhibition	-	0.7380	73.80%
CYP2C19 inhibition	-	0.5591	55.91%
CYP2D6 inhibition	-	0.8346	83.46%
CYP1A2 inhibition	+	0.5201	52.01%
CYP2C8 inhibition	+	0.6490	64.90%
CYP inhibitory promiscuity	-	0.8492	84.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6606	66.06%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.8166	81.66%
Skin irritation	-	0.7393	73.93%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8125	81.25%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7944	79.44%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8019	80.19%
Acute Oral Toxicity (c)	III	0.6314	63.14%
Estrogen receptor binding	+	0.8681	86.81%
Androgen receptor binding	+	0.7284	72.84%
Thyroid receptor binding	+	0.5822	58.22%
Glucocorticoid receptor binding	+	0.8208	82.08%
Aromatase binding	+	0.7560	75.60%
PPAR gamma	+	0.7739	77.39%
Honey bee toxicity	-	0.7548	75.48%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9886	98.86%

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	99.83%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.31%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	95.37%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.15%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.12%	89.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	94.88%	89.34%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.57%	85.14%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	92.29%	80.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.92%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.25%	94.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.92%	95.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.69%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.99%	99.23%
CHEMBL233	P35372	Mu opioid receptor	83.37%	97.93%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.22%	96.90%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.96%	100.00%
CHEMBL4581	P52732	Kinesin-like protein 1	82.75%	93.18%
CHEMBL1951	P21397	Monoamine oxidase A	82.39%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.36%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.02%	99.15%

Plants that contains it

• Garcinia xipshuanbannaensis

Cross-Links

• PubChem: 162944950
• LOTUS: LTS0147475
• wikiData: Q105301275