Hesperetin 7-O-glucoside

Details

• Internal ID: 59d6ce7b-658b-4706-990c-208c214133ad
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)[C@@H]2CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C22H24O11/c1-30-14-3-2-9(4-11(14)24)15-7-13(26)18-12(25)5-10(6-16(18)32-15)31-22-21(29)20(28)19(27)17(8-23)33-22/h2-6,15,17,19-25,27-29H,7-8H2,1H3/t15-,17+,19+,20-,21+,22+/m0/s1
• InChI Key: ADSYMQORONDIDD-ZJHVPRRPSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₄O₁₁
• Molecular Weight: 464.40 g/mol
• Exact Mass: 464.13186158 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.01
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• 31712-49-9
• Eriodictiol-7-glucoside
• hesperetin 7-O-beta-D-glucoside
• CHEMBL4460302
• (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl beta-D-glucopyranoside
• 4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-
• Hesperitin-7-beta-D-glucoside
• SCHEMBL14167583
• CHEBI:59015
• DTXSID80953661
• BDBM50503752
• AKOS032948812
• (2S)-hesperetin 7-O-beta-D-glucoside
• MS-28548
• HY-125130
• CS-0089420
• E80554
• A934558
• Q23055243
• 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4855	48.55%
Caco-2	-	0.8751	87.51%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	-	0.5706	57.06%
OATP1B1 inhibitior	+	0.9454	94.54%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6373	63.73%
P-glycoprotein inhibitior	-	0.7223	72.23%
P-glycoprotein substrate	-	0.7634	76.34%
CYP3A4 substrate	+	0.6192	61.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8374	83.74%
CYP3A4 inhibition	-	0.9108	91.08%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9173	91.73%
CYP2D6 inhibition	-	0.9514	95.14%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.4902	49.02%
CYP inhibitory promiscuity	-	0.7292	72.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8840	88.40%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6583	65.83%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.5102	51.02%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.7971	79.71%
Androgen receptor binding	-	0.6838	68.38%
Thyroid receptor binding	+	0.5345	53.45%
Glucocorticoid receptor binding	+	0.5722	57.22%
Aromatase binding	-	0.5233	52.33%
PPAR gamma	+	0.7153	71.53%
Honey bee toxicity	-	0.7282	72.82%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6549	65.49%
Fish aquatic toxicity	+	0.7079	70.79%

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	98.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.61%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.19%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	94.31%	96.21%
CHEMBL2581	P07339	Cathepsin D	93.99%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.95%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.97%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.79%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.71%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.61%	94.45%
CHEMBL4208	P20618	Proteasome component C5	90.33%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.32%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.41%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.23%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.79%	99.17%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.26%	95.78%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.32%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.36%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.09%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	81.10%	94.73%

Plants that contains it

• Citrus × aurantium

Cross-Links

• PubChem: 147394
• LOTUS: LTS0134734
• wikiData: Q23055243