Miscanthoside

Details

• Internal ID: d8072de7-f2eb-4924-9ae5-d351538176af
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=CC(=CC(=C2C1=O)O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC(=C(C=C4)O)O
• SMILES (Isomeric): C1C(OC2=CC(=CC(=C2C1=O)O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC(=C(C=C4)O)O
• InChI: InChI=1S/C21H22O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-5,14,16,18-25,27-29H,6-7H2
• InChI Key: RAFHNDRXYHOLSH-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₁₁
• Molecular Weight: 450.40 g/mol
• Exact Mass: 450.11621151 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): -0.31
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• Miscanthoside
• Eriodictyol 7-O-beta-D-glucoside
• 2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• Eriodictyol 7-O-glucoside
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-2,3-dihydro-5-hydroxy-, (S)-
• FT-0639507

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9296	92.96%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	-	0.5629	56.29%
OATP1B1 inhibitior	+	0.9562	95.62%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.5797	57.97%
P-glycoprotein inhibitior	-	0.7697	76.97%
P-glycoprotein substrate	-	0.9015	90.15%
CYP3A4 substrate	+	0.5877	58.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8398	83.98%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9084	90.84%
CYP2C8 inhibition	-	0.5905	59.05%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8595	85.95%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4936	49.36%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.4836	48.36%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7098	70.98%
Androgen receptor binding	-	0.5149	51.49%
Thyroid receptor binding	+	0.5665	56.65%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5406	54.06%
PPAR gamma	+	0.7601	76.01%
Honey bee toxicity	-	0.6682	66.82%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.8218	82.18%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4523129	O15056	Synaptojanin-2	874 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.70%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.36%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.82%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.51%	99.15%
CHEMBL2581	P07339	Cathepsin D	91.79%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.61%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.42%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.44%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.91%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.83%	86.92%
CHEMBL4208	P20618	Proteasome component C5	88.77%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.93%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.90%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	85.32%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.35%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.86%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.12%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.02%	94.80%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	81.51%	92.68%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.01%	95.78%

Plants that contains it

• Acer pictum subsp. mono
• Arnica longifolia
• Balanophora harlandii
• Balanophora tobiracola
• Bidens bipinnata
• Buphthalmum salicifolium
• Coleogyne ramosissima
• Crotalaria sessiliflora
• Dracocephalum tanguticum
• Malus pumila
• Phlomis nissolii
• Viscum articulatum
• Viscum coloratum

Cross-Links

• PubChem: 13254471
• LOTUS: LTS0254001
• wikiData: Q105232582