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

Details

• Internal ID: 3f7e517e-3316-4071-b529-ecc4d15b7c07
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: (2S)-7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-5-[(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(O2)C=C(C=C3OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)[C@@H]2CC(=O)C3=C(O2)C=C(C=C3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C22H24O11/c1-30-13-3-2-9(4-11(13)25)14-7-12(26)18-15(31-14)5-10(24)6-16(18)32-22-21(29)20(28)19(27)17(8-23)33-22/h2-6,14,17,19-25,27-29H,7-8H2,1H3/t14-,17+,19+,20-,21+,22+/m0/s1
• InChI Key: QSLBWGKNSBMTJL-YMTXFHFDSA-N
• Popularity: 3 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: 0.00
• Atomic LogP (AlogP): -0.01
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• Hesperetin 5-O-glucoside
• (2S)-7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• Hesperetin 5-glucoside
• (2S)-7-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-chroman-4-one
• CHEMBL463462
• DTXSID10989771
• (2S)-7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
• (S)-7-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-5-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one
• 4H-1-Benzopyran-4-one, 5-(beta-D-glucopyranosyloxy)-2,3-dihydro-7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-
• 7-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4855	48.55%
Caco-2	-	0.8918	89.18%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	-	0.5728	57.28%
OATP1B1 inhibitior	+	0.9372	93.72%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6107	61.07%
P-glycoprotein inhibitior	-	0.6625	66.25%
P-glycoprotein substrate	-	0.7717	77.17%
CYP3A4 substrate	+	0.6132	61.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8143	81.43%
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	+	0.4634	46.34%
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	-	0.8885	88.85%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3786	37.86%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.7323	73.23%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.5348	53.48%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.7955	79.55%
Androgen receptor binding	-	0.6499	64.99%
Thyroid receptor binding	+	0.5195	51.95%
Glucocorticoid receptor binding	+	0.6056	60.56%
Aromatase binding	-	0.5917	59.17%
PPAR gamma	+	0.6913	69.13%
Honey bee toxicity	-	0.7560	75.60%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6749	67.49%
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	98.60%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.18%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.91%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.22%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.58%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.83%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.71%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.01%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.40%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.77%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.44%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.16%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.56%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.48%	99.17%
CHEMBL4208	P20618	Proteasome component C5	85.58%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.15%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	84.14%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.74%	95.78%
CHEMBL2535	P11166	Glucose transporter	80.53%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.48%	97.14%

Plants that contains it

• Prunus davidiana

Cross-Links

• PubChem: 129663
• NPASS: NPC5778
• LOTUS: LTS0115792
• wikiData: Q72481525