(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编号: 175023
• 分子式: C27H32O14
• 平均质量: 580.53458
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: (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
• 别名: (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

登记号

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

理论计算性质

• Acid pKa: 9.315869
• 质子受体: 14
• 质子供体: 8
• LogD (pH = 5.5): -0.15695165
• LogD (pH = 7.4): -0.16210435
• Log P: -0.15688573
• 摩尔折射率: 134.3038 cm^3
• 极化性: 54.11746 Å^3
• 极化表面积: 225.06 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

详细说明

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.

参考文献

• 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)