(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-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 72962
• Molecular Formular: C27H32O14
• Molecular Mass: 580.53458
• Monoisotopic Mass: 580.1792057
• SMILES: c1c(cc2c(c1O)C(=O)C[C@H](O2)c1ccc(cc1)O)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)c2ccc(cc2)O)[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/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
• InChIKey: DFPMSGMNTNDNHN-ZPHOTFPESA-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-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: naringin
• Synonyms: Naringoside; Naringenine-7-rhamnosidoglucoside; Naringin; Naringin

Database IDs

• CAS Number: 10236-47-2
• PubChem SID: 162037882
• PubChem CID: 442428

CALCULATED PROPERTIES

• Acid pKa: 8.579344
• H Acceptors: 14
• H Donor: 8
• LogD (pH = 5.5): -0.15724456
• LogD (pH = 7.4): -0.18468763
• Log P: -0.15688573
• Molar Refractivity: 134.3038 cm^3
• Polarizability: 54.11746 Å^3
• Polar Surface Area: 225.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• Storage Condition: -20°C

Product Information

• Purity: 98.0
• Salt Data: Free Base
• Classification: Genuine Natural Compounds

DETAILS

Selleck Chemicals - S2329

Research Area: Cardiovascular Disease
Biological Activity:
Naringin (Naringoside) is a flavanone glycoside and is a major flavonoid in grapefruit and gives the grapefruit juice its bitter taste. Naringin (Naringoside) is metabolized to the flavanone naringenin in humans. Both naringenin and hesperetin, which are the aglycones of naringin and hesperidin, occur naturally in citrus fruits.Naringin exerts a variety of pharmacological effects such as antioxidant activity, blood lipid lowering, anticancer activity, and inhibition of selected cytochrome P450 enzymes, including CYP3A4 and CYP1A2. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Naringin