1-Hydroxy-2,6-dimethoxy-8-[(6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]-9H-xanthen-9-one

Details

• Internal ID: e43d4238-831c-4e8b-a324-4dc4ac635449
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1-hydroxy-2,6-dimethoxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyxanthen-9-one
• SMILES (Canonical): COC1=C(C2=C(C=C1)OC3=C(C2=O)C(=CC(=C3)OC)OC4C(C(C(C(O4)COC5C(C(C(CO5)O)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C2=C(C=C1)OC3=C(C2=O)C(=CC(=C3)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)O)O)O)O
• InChI: InChI=1S/C26H30O15/c1-35-9-5-13-16(21(31)17-11(39-13)3-4-12(36-2)19(17)29)14(6-9)40-26-24(34)22(32)20(30)15(41-26)8-38-25-23(33)18(28)10(27)7-37-25/h3-6,10,15,18,20,22-30,32-34H,7-8H2,1-2H3/t10-,15-,18+,20-,22+,23-,24-,25+,26-/m1/s1
• InChI Key: NNYKTKDAAWADQG-HBSGFRINSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₁₅
• Molecular Weight: 582.50 g/mol
• Exact Mass: 582.15847025 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.69
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• alpha-Glucosidase-IN-24
• orb1981828
• CHEMBL2409519
• HY-N11512
• 1-O-[beta-D-Xylopyranosyl-(1-6)-beta-D-glucopyranosyl]-8-hydroxy-3,7-dimethoxyxanthone
• 9H-Xanthen-9-one, 1-hydroxy-2,6-dimethoxy-8-[(6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]-
• CS-0648475
• E80548
• T75612
• 1-HYDROXY-2,6-DIMETHOXY-8-[(6-O-BETA-D-XYLOPYRANOSYL-BETA-D-GLUCOPYRANOSYL)OXY]-9H-XANTHEN-9-ONE
• 9H-Xanthen-9-one, 1-hydroxy-2,6-dimethoxy-8-[(6-O-|A-D-xylopyranosyl-|A-D-glucopyranosyl)oxy]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5181	51.81%
Caco-2	-	0.8901	89.01%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5700	57.00%
OATP2B1 inhibitior	-	0.5863	58.63%
OATP1B1 inhibitior	+	0.8869	88.69%
OATP1B3 inhibitior	+	0.9535	95.35%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6129	61.29%
P-glycoprotein inhibitior	-	0.5957	59.57%
P-glycoprotein substrate	-	0.5216	52.16%
CYP3A4 substrate	+	0.6420	64.20%
CYP2C9 substrate	-	0.8664	86.64%
CYP2D6 substrate	-	0.8478	84.78%
CYP3A4 inhibition	-	0.9082	90.82%
CYP2C9 inhibition	-	0.9593	95.93%
CYP2C19 inhibition	-	0.9192	91.92%
CYP2D6 inhibition	-	0.8843	88.43%
CYP1A2 inhibition	-	0.8533	85.33%
CYP2C8 inhibition	+	0.5489	54.89%
CYP inhibitory promiscuity	-	0.9119	91.19%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7055	70.55%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9275	92.75%
Skin irritation	-	0.8390	83.90%
Skin corrosion	-	0.9633	96.33%
Ames mutagenesis	+	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6874	68.74%
Micronuclear	+	0.5574	55.74%
Hepatotoxicity	-	0.8101	81.01%
skin sensitisation	-	0.8974	89.74%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9585	95.85%
Acute Oral Toxicity (c)	III	0.7230	72.30%
Estrogen receptor binding	+	0.8344	83.44%
Androgen receptor binding	+	0.5671	56.71%
Thyroid receptor binding	+	0.5133	51.33%
Glucocorticoid receptor binding	+	0.6232	62.32%
Aromatase binding	+	0.6312	63.12%
PPAR gamma	+	0.7249	72.49%
Honey bee toxicity	-	0.8138	81.38%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6649	66.49%
Fish aquatic toxicity	+	0.8120	81.20%

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	99.07%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.51%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.52%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.74%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.36%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.69%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.33%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.94%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.95%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.90%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.84%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.04%	89.62%
CHEMBL4208	P20618	Proteasome component C5	86.83%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	85.69%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.99%	97.36%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.91%	96.00%
CHEMBL2535	P11166	Glucose transporter	82.33%	98.75%
CHEMBL220	P22303	Acetylcholinesterase	82.19%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.93%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.70%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.30%	86.92%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.22%	90.71%

Plants that contains it

• Swertia kouitchensis

Cross-Links

• PubChem: 72163130
• LOTUS: LTS0226127
• wikiData: Q105182387