8-(2-O-beta-D-Xylopyranosyl-beta-D-glucopyranosyl)-4',5,7-trihydroxy-3'-methoxyflavone

Details

• Internal ID: d33f06db-80b6-4ee9-9ff6-9e01104021f3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4C(C(C(C(O4)CO)O)O)OC5C(C(C(CO5)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-38-16-4-9(2-3-10(16)29)15-6-13(32)18-11(30)5-12(31)19(24(18)40-15)25-26(22(36)21(35)17(7-28)41-25)42-27-23(37)20(34)14(33)8-39-27/h2-6,14,17,20-23,25-31,33-37H,7-8H2,1H3/t14-,17-,20+,21-,22+,23-,25+,26-,27+/m1/s1
• InChI Key: ZMXRYFUILUMXHH-GWHYTMBFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -1.44
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

• 8-(2-O-beta-D-Xylopyranosyl-beta-D-glucopyranosyl)-4',5,7-trihydroxy-3'-methoxyflavone
• 124934-30-1
• 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-(2-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4761	47.61%
Caco-2	-	0.9228	92.28%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5114	51.14%
OATP2B1 inhibitior	-	0.7091	70.91%
OATP1B1 inhibitior	+	0.8599	85.99%
OATP1B3 inhibitior	+	0.9679	96.79%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7751	77.51%
P-glycoprotein inhibitior	-	0.5711	57.11%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6570	65.70%
CYP2C9 substrate	-	0.8389	83.89%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9417	94.17%
CYP2C9 inhibition	-	0.9488	94.88%
CYP2C19 inhibition	-	0.9370	93.70%
CYP2D6 inhibition	-	0.9411	94.11%
CYP1A2 inhibition	-	0.9224	92.24%
CYP2C8 inhibition	+	0.6531	65.31%
CYP inhibitory promiscuity	-	0.8596	85.96%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6677	66.77%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9165	91.65%
Skin irritation	-	0.8242	82.42%
Skin corrosion	-	0.9582	95.82%
Ames mutagenesis	+	0.5544	55.44%
Human Ether-a-go-go-Related Gene inhibition	-	0.3750	37.50%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9265	92.65%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8890	88.90%
Acute Oral Toxicity (c)	III	0.7135	71.35%
Estrogen receptor binding	+	0.8399	83.99%
Androgen receptor binding	+	0.7013	70.13%
Thyroid receptor binding	-	0.4872	48.72%
Glucocorticoid receptor binding	+	0.6382	63.82%
Aromatase binding	+	0.6358	63.58%
PPAR gamma	+	0.7137	71.37%
Honey bee toxicity	-	0.7245	72.45%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	-	0.4193	41.93%

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	99.51%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.90%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.75%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.82%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.63%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.86%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.77%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.07%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.48%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.64%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.27%	85.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.19%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.06%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.84%	97.14%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.98%	96.21%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	82.89%	89.23%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.60%	91.24%
CHEMBL3401	O75469	Pregnane X receptor	82.50%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	81.94%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.66%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.59%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.32%	96.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.44%	90.71%

Plants that contains it

• Derris reticulata
• Eucalyptus ovata
• Gentiana arisanensis
• Panzerina lanata
• Solanum dulcamara

Cross-Links

• PubChem: 101429641
• NPASS: NPC143014