8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one

Details

• Internal ID: 47890c9f-b337-4a58-8294-80f07dd54ce9
• 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,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-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)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)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]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C28H32O17/c1-40-15-4-9(2-3-10(15)31)14-6-12(33)18-11(32)5-13(34)24(25(18)41-14)44-28-26(22(38)20(36)17(8-30)43-28)45-27-23(39)21(37)19(35)16(7-29)42-27/h2-6,16-17,19-23,26-32,34-39H,7-8H2,1H3/t16-,17-,19-,20-,21+,22+,23-,26-,27+,28+/m1/s1
• InChI Key: DFCXLWVWSHBLPT-OTMKDXJRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₇
• Molecular Weight: 640.50 g/mol
• Exact Mass: 640.16394955 g/mol
• Topological Polar Surface Area (TPSA): 275.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -2.41
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5457	54.57%
Caco-2	-	0.9160	91.60%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	0.5755	57.55%
OATP1B1 inhibitior	+	0.8822	88.22%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6239	62.39%
P-glycoprotein inhibitior	-	0.5597	55.97%
P-glycoprotein substrate	-	0.6050	60.50%
CYP3A4 substrate	+	0.6318	63.18%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9437	94.37%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.9150	91.50%
CYP2C8 inhibition	+	0.6797	67.97%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9234	92.34%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	-	0.5392	53.92%
Human Ether-a-go-go-Related Gene inhibition	-	0.3680	36.80%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8821	88.21%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.8316	83.16%
Androgen receptor binding	+	0.6713	67.13%
Thyroid receptor binding	+	0.5151	51.51%
Glucocorticoid receptor binding	+	0.5922	59.22%
Aromatase binding	+	0.6346	63.46%
PPAR gamma	+	0.7587	75.87%
Honey bee toxicity	-	0.6854	68.54%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.6698	66.98%

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	99.05%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.25%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.17%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.69%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.57%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.63%	85.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.55%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.99%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.79%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.96%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.51%	96.21%
CHEMBL1951	P21397	Monoamine oxidase A	87.37%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.18%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.10%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.84%	94.45%
CHEMBL3194	P02766	Transthyretin	83.31%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.39%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.43%	95.89%

Plants that contains it

• Setaria italica

Cross-Links

• PubChem: 162989371
• LOTUS: LTS0033984
• wikiData: Q104977751