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]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

Details

• Internal ID: 821c8ce9-8cba-4d32-85d1-6aa38c533513
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-8-O-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]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(C=C(C4=C3OC(=CC4=O)C5=CC=C(C=C5)O)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C(C=C(C4=C3OC(=CC4=O)C5=CC=C(C=C5)O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C26H28O15/c27-7-16-19(34)20(35)24(41-25-21(36)18(33)14(32)8-37-25)26(39-16)40-22-13(31)5-11(29)17-12(30)6-15(38-23(17)22)9-1-3-10(28)4-2-9/h1-6,14,16,18-21,24-29,31-36H,7-8H2/t14-,16-,18+,19-,20+,21-,24-,25+,26+/m1/s1
• InChI Key: VPFZYCNBWXGXHL-JXYLQRTFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₅
• Molecular Weight: 580.50 g/mol
• Exact Mass: 580.14282018 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -1.78
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5110	51.10%
Caco-2	-	0.9324	93.24%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.4988	49.88%
OATP2B1 inhibitior	-	0.5570	55.70%
OATP1B1 inhibitior	+	0.8827	88.27%
OATP1B3 inhibitior	+	0.9174	91.74%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6810	68.10%
P-glycoprotein inhibitior	-	0.6236	62.36%
P-glycoprotein substrate	-	0.6055	60.55%
CYP3A4 substrate	+	0.6546	65.46%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9373	93.73%
CYP2C9 inhibition	-	0.9644	96.44%
CYP2C19 inhibition	-	0.9395	93.95%
CYP2D6 inhibition	-	0.9332	93.32%
CYP1A2 inhibition	-	0.9304	93.04%
CYP2C8 inhibition	+	0.6484	64.84%
CYP inhibitory promiscuity	-	0.8779	87.79%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6882	68.82%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.9109	91.09%
Skin irritation	-	0.8205	82.05%
Skin corrosion	-	0.9667	96.67%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4282	42.82%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7288	72.88%
skin sensitisation	-	0.9071	90.71%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9402	94.02%
Acute Oral Toxicity (c)	III	0.4508	45.08%
Estrogen receptor binding	+	0.8336	83.36%
Androgen receptor binding	+	0.7185	71.85%
Thyroid receptor binding	+	0.5577	55.77%
Glucocorticoid receptor binding	+	0.5785	57.85%
Aromatase binding	+	0.7058	70.58%
PPAR gamma	+	0.7660	76.60%
Honey bee toxicity	-	0.6590	65.90%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6750	67.50%
Fish aquatic toxicity	+	0.7253	72.53%

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	99.57%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.47%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.95%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.94%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.41%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.88%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.74%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.26%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.88%	86.92%
CHEMBL242	Q92731	Estrogen receptor beta	90.55%	98.35%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	88.31%	83.57%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.60%	95.83%
CHEMBL3194	P02766	Transthyretin	84.95%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.83%	99.17%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	84.13%	80.33%
CHEMBL3401	O75469	Pregnane X receptor	84.12%	94.73%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.01%	97.28%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.38%	86.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.90%	95.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.38%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.08%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.91%	96.21%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	81.88%	89.23%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.73%	91.71%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.59%	91.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.50%	95.89%

Plants that contains it

• Setaria italica

Cross-Links

• PubChem: 162995270
• LOTUS: LTS0255490
• wikiData: Q105290767