(2S,3S,4S,5R,6S)-4-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-3-yl acetate

• ChemBase ID: 177795
• Molecular Formular: C25H24O12
• Molecular Mass: 516.45086
• Monoisotopic Mass: 516.12677621
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H]([C@@H](O1)Oc1c(oc2c(c1=O)c(cc(c2)O)O)c1ccc(cc1)O)O)OC(=O)C)OC(=O)C)C
• Canonical SMILES: CC(=O)O[C@H]1[C@H](C)O[C@H]([C@@H]([C@H]1OC(=O)C)O)Oc1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(cc1)O
• InChI: InChI=1S/C25H24O12/c1-10-21(34-11(2)26)24(35-12(3)27)20(32)25(33-10)37-23-19(31)18-16(30)8-15(29)9-17(18)36-22(23)13-4-6-14(28)7-5-13/h4-10,20-21,24-25,28-30,32H,1-3H3/t10-,20+,21-,24-,25-/m0/s1
• InChIKey: SXOZSDJHGMAEGZ-IGKKHSBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-4-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-3-yl acetate
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-4-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-3-yl acetate
• Synonyms: 3-[(3,4-Di-O-acetyl-6-deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Kaempferol; 3'',4''-Di-O-acetylafzelin; SL0101

Database IDs

• CAS Number: 77307-50-7
• PubChem SID: 164233705
• PubChem CID: 10459196

CALCULATED PROPERTIES

• Acid pKa: 6.4338903
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 2.0403767
• LogD (pH = 7.4): 1.0711181
• Log P: 2.0878909
• Molar Refractivity: 124.0539 cm^3
• Polarizability: 48.54771 Å^3
• Polar Surface Area: 178.28 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Ethyl Acetate; Methanol
• Apperance: Tan to Yellow Solid
• Melting Point: 128-132°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - S560000

A potent and selective inhibitor of p90 Rsk, without inhibiting the function of upstream kinases such as MEK, Raf, or PKC.

REFERENCES

• Maloney, D.J. and Hecht, S.M.: Organic Letters, 7, 6, 1097 (2005)