3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

• ChemBase ID: 154733
• Molecular Formular: C21H20O11
• Molecular Mass: 448.3769
• Monoisotopic Mass: 448.10056146
• SMILES: c1cc(ccc1c1c(c(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)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
• InChI: InChI=1S/C21H20O11/c22-7-13-15(25)17(27)19(29)21(32-13)30-10-5-11(24)14-12(6-10)31-20(18(28)16(14)26)8-1-3-9(23)4-2-8/h1-6,13,15,17,19,21-25,27-29H,7H2/t13-,15-,17+,19-,21-/m1/s1
• InChIKey: YPWHZCPMOQGCDQ-HMGRVEAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: 3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one
• Synonyms: 7-(β-D-Glucopyranosyloxy)-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Kaempferol 7-O-glucoside; Populnin; Kaempferol 7-O-β -D-glucopyranoside

Database IDs

• CAS Number: 16290-07-6
• MDL Number: MFCD08459623
• Beilstein Number: 68205
• PubChem SID: 162248871
• PubChem CID: 10095180

CALCULATED PROPERTIES

• Acid pKa: 8.005597
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): 0.19045046
• LogD (pH = 7.4): 0.09229139
• Log P: 0.19179669
• Molar Refractivity: 107.0257 cm^3
• Polarizability: 41.515594 Å^3
• Polar Surface Area: 186.37 Å^2
• Rotatable Bonds: 4
• 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: ≥90.0% (HPLC)
• Empirical Formula (Hill Notation): C21H20O11

DETAILS

Sigma Aldrich - 18854

Biochem/physiol Actions
A flavonoid glycoside, found in plants such as aspen bark and leaves and poplar buds and bark, contains antimicrobial activities1, and investigated for anticancer activities.2