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-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

Details

• Internal ID: b1bc478e-85ce-4a9b-ba9b-5db7a18086c7
• 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-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-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)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)O)CO)O)O)O)O)O
• InChI: InChI=1S/C26H28O16/c27-6-16-19(35)20(36)24(42-25-21(37)18(34)14(33)7-38-25)26(40-16)41-22-13(32)4-11(30)17-12(31)5-15(39-23(17)22)8-1-2-9(28)10(29)3-8/h1-5,14,16,18-21,24-30,32-37H,6-7H2/t14-,16-,18+,19-,20+,21-,24-,25+,26+/m1/s1
• InChI Key: YWBYOKPVBQBJDO-JXYLQRTFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₆
• Molecular Weight: 596.50 g/mol
• Exact Mass: 596.13773480 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.08
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• 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	-	0.9309	93.09%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.4988	49.88%
OATP2B1 inhibitior	-	0.5567	55.67%
OATP1B1 inhibitior	+	0.9016	90.16%
OATP1B3 inhibitior	+	0.9174	91.74%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6777	67.77%
P-glycoprotein inhibitior	-	0.5995	59.95%
P-glycoprotein substrate	-	0.6052	60.52%
CYP3A4 substrate	+	0.6484	64.84%
CYP2C9 substrate	-	0.6709	67.09%
CYP2D6 substrate	-	0.8582	85.82%
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	+	0.6126	61.26%
CYP inhibitory promiscuity	-	0.8779	87.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6882	68.82%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.9046	90.46%
Skin irritation	-	0.8205	82.05%
Skin corrosion	-	0.9667	96.67%
Ames mutagenesis	+	0.6036	60.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.6477	64.77%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7288	72.88%
skin sensitisation	-	0.9071	90.71%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9558	95.58%
Acute Oral Toxicity (c)	III	0.4508	45.08%
Estrogen receptor binding	+	0.8372	83.72%
Androgen receptor binding	+	0.6803	68.03%
Thyroid receptor binding	+	0.5596	55.96%
Glucocorticoid receptor binding	+	0.5560	55.60%
Aromatase binding	+	0.6507	65.07%
PPAR gamma	+	0.7642	76.42%
Honey bee toxicity	-	0.6438	64.38%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6850	68.50%
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	99.79%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.22%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.29%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.04%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.12%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.06%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.40%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.24%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.94%	94.45%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.72%	95.83%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	86.04%	80.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.00%	91.24%
CHEMBL3401	O75469	Pregnane X receptor	85.06%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.40%	86.33%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	83.35%	83.57%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.17%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.07%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.28%	99.17%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.11%	97.28%
CHEMBL3194	P02766	Transthyretin	80.87%	90.71%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	80.22%	89.23%

Plants that contains it

• Setaria italica

Cross-Links

• PubChem: 162983153
• LOTUS: LTS0263655
• wikiData: Q105366419