(2S,3S,5S)-3,4,5-tris(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl 3,4,5-trihydroxybenzoate

• ChemBase ID: 176305
• Molecular Formular: C41H32O26
• Molecular Mass: 940.67718
• Monoisotopic Mass: 940.11818114
• SMILES: O1[C@@H](OC(=O)c2cc(c(c(c2)O)O)O)[C@H](OC(=O)c2cc(c(c(c2)O)O)O)C([C@H](C1COC(=O)c1cc(c(c(c1)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O
• Canonical SMILES: O=C(c1cc(O)c(c(c1)O)O)O[C@@H]1OC(COC(=O)c2cc(O)c(c(c2)O)O)[C@@H](C([C@H]1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O
• InChI: InChI=1S/C41H32O26/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16/h1-10,27,33-35,41-56H,11H2/t27?,33-,34?,35-,41-/m0/s1
• InChIKey: QJYNZEYHSMRWBK-CPKLCXDTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,5S)-3,4,5-tris(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl 3,4,5-trihydroxybenzoate
• IUPAC Traditional name: (2S,3S,5S)-3,4,5-tris(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl 3,4,5-trihydroxybenzoate
• Synonyms: PGG; 1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose >90%

Database IDs

• CAS Number: 14937-32-7
• PubChem SID: 164232215
• PubChem CID: 45040197

CALCULATED PROPERTIES

• Acid pKa: 7.4349327
• H Acceptors: 21
• H Donor: 15
• LogD (pH = 5.5): 4.9854827
• LogD (pH = 7.4): 4.6261144
• Log P: 4.9904804
• Molar Refractivity: 214.7469 cm^3
• Polarizability: 82.56463 Å^3
• Polar Surface Area: 444.18 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Grey Solid
• Melting Point: >180°C dec.

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - P270450

Found to exhibit in vitro growth-inhibiting effect on human hepatocellular carcinoma cell line, SK-HEP-1 cells.

REFERENCES

• Oh, G-S, et al.: Cancer Letters, 174, 17 ( 2001)