(1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid

• ChemBase ID: 306280
• Molecular Formular: C25H24O12
• Molecular Mass: 516.45086
• Monoisotopic Mass: 516.12677621
• SMILES: C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/c1cc(c(cc1)O)O)O)OC(=O)/C=C/c1cc(c(cc1)O)O
• Canonical SMILES: O=C(O[C@@H]1C[C@@](O)(C[C@H]([C@H]1O)OC(=O)/C=C/c1ccc(c(c1)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
• InChI: InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
• InChIKey: KRZBCHWVBQOTNZ-PSEXTPKNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid
• IUPAC Traditional name: (1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid
• Synonyms: Isochlorogenic acid A; 3,5-Di-O-caffeoylquinic acid

Database IDs

• CAS Number: 2450-53-5

CALCULATED PROPERTIES

• LogD (pH = 7.4): -1.2861438
• Log P: 2.1582303
• Molar Refractivity: 126.7642 cm^3
• Polarizability: 48.731434 Å^3
• Polar Surface Area: 211.28 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false
• Acid pKa: 3.2760208
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -0.047524065

PROPERTIES

Physical Property

• Apperance: Powder