(2S)-7-{[(2S,4S,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(3R,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: 175023
• Molecular Formular: C27H32O14
• Molecular Mass: 580.53458
• Monoisotopic Mass: 580.1792057
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)Oc1cc(c2c(c1)O[C@@H](CC2=O)c1ccc(cc1)O)O)OC1[C@@H](C([C@H]([C@@H](O1)C)O)O)O)O)O
• Canonical SMILES: OCC1O[C@@H](Oc2cc(O)c3c(c2)O[C@@H](CC3=O)c2ccc(cc2)O)C([C@H]([C@@H]1O)O)OC1O[C@@H](C)[C@@H](C([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-JMEBPUETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-7-{[(2S,4S,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(3R,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: (2S)-7-{[(2S,4S,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(3R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one
• Synonyms: (S)-7-[[2-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one Hydrate; Naringenin 7-Neohesperidoside Hydrate; Aurantiin Hydrate; Naringin Hydrate

Database IDs

• CAS Number: 132203-74-8
• PubChem SID: 164230933
• PubChem CID: 71750953

CALCULATED PROPERTIES

• Acid pKa: 9.315869
• H Acceptors: 14
• H Donor: 8
• LogD (pH = 5.5): -0.15695165
• LogD (pH = 7.4): -0.16210435
• 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

DETAILS

Toronto Research Chemicals - N378980

The major flavonoid found in grapefruit juice. It has antioxidant, lipid lowering, and anticancer activities. It is also an inhibitor of cytochrome P450 enzymes, affecting drug metabolism and thus drug absorption in humans.

REFERENCES

• Su, Z., et al.: J. Pharm. Biomed. Anal., 53, 454 (2010)
• Carino-Cortes, R., et al.: Biol. Pharm. Bull., 33, 697 (2010)
• Jordan, M., et al.: J. Agric. Food Chem., 58, 8265 (2010)