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

• ChemBase ID: 154806
• Molecular Formular: C33H40O19
• Molecular Mass: 740.6593
• Monoisotopic Mass: 740.21637906
• SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)O)O)O)O)O)O)O
• Canonical SMILES: Oc1ccc(cc1)c1oc2cc(O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)cc(c2c(=O)c1O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@@H]([C@@H]([C@H]1O)O)O)O
• InChI: InChI=1S/C33H40O19/c1-10-19(36)23(40)26(43)31(47-10)46-9-17-21(38)25(42)28(45)33(51-17)52-30-22(39)18-15(35)7-14(49-32-27(44)24(41)20(37)11(2)48-32)8-16(18)50-29(30)12-3-5-13(34)6-4-12/h3-8,10-11,17,19-21,23-28,31-38,40-45H,9H2,1-2H3/t10-,11-,17+,19-,20-,21-,23+,24+,25-,26+,27+,28+,31+,32-,33-/m0/s1
• InChIKey: PEFASEPMJYRQBW-HKWQTAEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-7-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: robinin
• Synonyms: Kaempferol 3-O-robinoside-7-O-rhamnoside; Robinin

Database IDs

• CAS Number: 301-19-9
• EC Number: 206-113-3
• PubChem SID: 162248944
• PubChem CID: 5281693

CALCULATED PROPERTIES

• Acid pKa: 7.083348
• H Acceptors: 19
• H Donor: 11
• LogD (pH = 5.5): -1.797459
• LogD (pH = 7.4): -2.2864673
• Log P: -1.7863538
• Molar Refractivity: 168.7649 cm^3
• Polarizability: 67.70727 Å^3
• Polar Surface Area: 304.21 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Yellow powder

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): C33H40O19

DETAILS

Sigma Aldrich - 53609

Biochem/physiol Actions
Flavone glycoside from Robinia with antibacterial1 and diuretic 2 properties; derived from kaempferol.3,4
The ability of robinin to reverse the multidrug resistance of the human colon cancer cell line Colo 320 expreβing MDR1/LRP was explored by monitoring their uptake of Rhodamine 123, but was shown to have minimal effect. Robinin was detected in lysates of the human breast cancer cell line MCF-7 using liquid chromatography-tandem maβ spectrometry. 4