1-(4-{[(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}-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one dihydrate

• ChemBase ID: 179894
• Molecular Formular: C28H40O17
• Molecular Mass: 648.607
• Monoisotopic Mass: 648.22654982
• SMILES: [C@@H]1([C@@H](O[C@@H]([C@H]([C@@H]1O)O)CO)Oc1cc(c(c(c1)O)C(=O)CCc1cc(c(cc1)OC)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O.O.O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc(O)c(c(c2)O)C(=O)CCc2ccc(c(c2)O)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.O.O
• InChI: InChI=1S/C28H36O15.2H2O/c1-11-21(34)23(36)25(38)27(40-11)43-26-24(37)22(35)19(10-29)42-28(26)41-13-8-16(32)20(17(33)9-13)14(30)5-3-12-4-6-18(39-2)15(31)7-12;;/h4,6-9,11,19,21-29,31-38H,3,5,10H2,1-2H3;2*1H2/t11-,19+,21-,22+,23+,24-,25+,26+,27-,28+;;/m0../s1
• InChIKey: GLCRRKNUKQYFJC-NXBIYWLGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-{[(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}-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one dihydrate
• IUPAC Traditional name: 1-(4-{[(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}-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one dihydrate
• Synonyms: Hesperetin 7-neohesperidoside; Neohesperidin dihydrochalcone

Database IDs

• CAS Number: 20702-77-6
• PubChem SID: 164235804
• PubChem CID: 51052080

CALCULATED PROPERTIES

• Acid pKa: 9.56446
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): 0.74583834
• LogD (pH = 7.4): 0.74292827
• Log P: 0.7458755
• Molar Refractivity: 143.1845 cm^3
• Polarizability: 57.317883 Å^3
• Polar Surface Area: 245.29 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Activates the human sweet receptor TAS1R2+TAS1R3; Radical scavenger

Product Information

• Salt Data: 2 H2O
• Biological Source: Derived semisynthetically from 3',5,7-Trihydroxy-4'-methoxyflavanone
• Application(s): Antioxidant; Artificial sweetener; Flavour enhancer

REFERENCES

• 1. Winnig M, Bufe B, Kratochwil NA, Slack JP, Meyerhof W. The binding site for neohesperidin dihydrochalcone at the human sweet taste receptor. BMC Struct Biol. 2007 Oct 12;7:66.
• 2. Choi JM, Yoon BS, Lee SK, Hwang JK, Ryang R.
• Antioxidant properties of neohesperidin dihydrochalcone: inhibition of hypochlorous acid-induced DNA strand breakage, protein degradation, and cell death. Biol Pharm Bull. 2007 Feb;30(2):324-30.