(2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(3-hydroxy-5-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 73090
• Molecular Formular: C28H34O15
• Molecular Mass: 610.56056
• Monoisotopic Mass: 610.18977039
• SMILES: c1c(cc2c(c1O)C(=O)C[C@H](O2)c1cc(cc(c1)O)OC)O[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O[C@@H]1O[C@H]([C@@H]([C@H]([C@H]1O)O)O)C)O)O)CO
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)O[C@@H](CC3=O)c2cc(O)cc(c2)OC)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C28H34O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-14-6-15(31)20-16(32)8-17(41-18(20)7-14)11-3-12(30)5-13(4-11)38-2/h3-7,10,17,19,21-31,33-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
• InChIKey: TWAZWVPPDIUVOD-UZRWAPQLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(3-hydroxy-5-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: (2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(3-hydroxy-5-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one; (2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(3-hydroxy-5-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• Synonyms: Neohesperidin; (S)-7-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(3-hydroxy-5-methoxyphenyl )chroman-4-one; Hesperetin 7-neohesperidoside; Neohesperidin

Database IDs

• CAS Number: 13241-33-3
• PubChem SID: 162038010
• PubChem CID: 24721685

CALCULATED PROPERTIES

• Acid pKa: 9.203239
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): -0.31464243
• LogD (pH = 7.4): -0.32130903
• Log P: -0.314557
• Molar Refractivity: 140.767 cm^3
• Polarizability: 56.675926 Å^3
• Polar Surface Area: 234.29 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Mechanism of Action: Free radical scavenger

Product Information

• Salt Data: Free Base
• Biological Source: Constit. of Seville orange peel (Citrus aurantium) and other Citrus spp.
• Application(s): Anti-allergic; Antioxidant; Depressant; Flavouring agent

DETAILS

Selleck Chemicals - S2332

Research Area: Metabolic Disease
Biological Activity:
Neohesperidin is an antioxidant agent with an IC50 of 22.31 µg/ml in the 1,1-diphenyl-2-picryldydrazyl (DPPH) radical-scavenging assay.Neohesperidin (50 mg/kg) significantly inhibited 55.0% of HCl/ethanol-induced gastric lesions, and increased the mucus content. In pylorus ligated rats, neohesperidin (50 mg/kg) significantly decreased the volume of gastric secretion and gastric acid output, and increased the pH. In addition, neohesperidin inhibited the efflux of the P-glycoprotein substrate rhodamine 123 in a concentration-dependent manner. Neohesperidin also inhibits the growth of Caco-2, CEM/ADR5000 and CCRF-CEM leukaemia cells with IC50 of 0.17, 0.17 and 0.12 mM, respectively. Neohesperidin can be isolated from ethyl acetate fractions of C. jambhiri. [1][2]

REFERENCES

• Lee JH et al. Phytother Res. 2009 Dec;23(12):1748-53.
• 1. Ferna'ndez SP, Wasowski C, Loscalzo LM, Granger RE, Johnston GA, Paladini AC, Marder M. Central nervous system depressant action of flavonoid glycosides. Eur J Pharmacol. 2006 Jun 13;539(3):168-76.
• 2. Kubo M, Fujita T, Nishimura S, Tokunaga M, Matsuda H, Gato T, Tomohiro N, Sasaki K, Utsunomiya N. Seasonal variation in anti-allergic activity of citrus fruits and flavanone glycoside content.
• Natural Medicines 58 (2004), pp. 284?94.
• 3. Finotti E, Di Majo D. Influence of solvents on the antioxidant property of flavonoids. Nahrung. 2003 Jun;47(3):186-7.