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}-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

• ChemBase ID: 154732
• Molecular Formular: C27H30O15
• Molecular Mass: 594.5181
• Monoisotopic Mass: 594.15847026
• SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1Oc1cc(c2c(c1)oc(c(c2=O)O)c1ccc(cc1)O)O)CO)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(c(c3=O)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/C27H30O15/c1-9-17(31)20(34)23(37)26(38-9)42-25-21(35)18(32)15(8-28)41-27(25)39-12-6-13(30)16-14(7-12)40-24(22(36)19(16)33)10-2-4-11(29)5-3-10/h2-7,9,15,17-18,20-21,23,25-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,23+,25+,26-,27+/m0/s1
• InChIKey: ZEJXENDZTYVXDP-CSJHBIPPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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}-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: 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}-3,5-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• Synonyms: 3,4′,5,7-Tetrahydroxyflavone 7-[2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside]; 3,4′,5,7-Tetrahydroxyflavone 7-neohesperidoside; Kaempferol 7-O-neohesperidoside

Database IDs

• CAS Number: 17353-03-6
• EC Number: 241-377-3
• PubChem SID: 162248870
• PubChem CID: 5483905

CALCULATED PROPERTIES

• Acid pKa: 8.00558
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): -0.5334753
• LogD (pH = 7.4): -0.631638
• Log P: -0.532129
• Molar Refractivity: 137.8953 cm^3
• Polarizability: 54.610004 Å^3
• Polar Surface Area: 245.29 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Safety Statements: 22-24/25
• Storage Temperature: -20°C

Product Information

• Purity: ≥95.0% (HPLC)
• Empirical Formula (Hill Notation): C27H30O15

DETAILS

Sigma Aldrich - 92996

Biochem/physiol Actions
Bioflavonoid, that was shown to have in vitro antitumor activity against cancer cells and might also be involved in the antitumor activity of lychee seeds1.
Kaempferol 7-O-neohesperidoside was shown to have anti-proliferative effects on a variety of human cancer cell lines in vitro. 1
General description
Kaempferol 7-O-neohesperidoside is a flavonoid glycoside that was isolated from the seeds of the Litchi chinensis fruit. 1