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

• ChemBase ID: 154834
• Molecular Formular: C41H32O26
• Molecular Mass: 940.67718
• Monoisotopic Mass: 940.11818114
• SMILES: c1c(cc(c(c1O)O)O)C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=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)OC(=O)c1cc(c(c(c1)O)O)O
• Canonical SMILES: O=C(c1cc(O)c(c(c1)O)O)O[C@@H]1O[C@H](COC(=O)c2cc(O)c(c(c2)O)O)[C@H]([C@@H]([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+/m1/s1
• InChIKey: QJYNZEYHSMRWBK-NIKIMHBISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• IUPAC Traditional name: 1,2,3,4,6-pentagalloylglucose
• Synonyms: 1,2,3,4,6-Penta-O-galloyl-b-D-glucopyranose; 1,2,3,4,6-pentakis(3,4,5-trihydroxybenzoate)-b-D-Glucopyranose; Gallic acid, pentaester with b-D-glucopyranose; Glucopyranose, pentagallate, b-D; PGG; Penta-1,2,3,4,6-O-galloyl-b-D-glucose; Penta-O-galloyl-beta-D-glucose; Penta-O-galloyl-β-D-glucose hydrate

Database IDs

• CAS Number: 14937-32-7(anhydrous)
• MDL Number: MFCD03788860
• PubChem SID: 162248972
• PubChem CID: 65238

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: DMSO: ≥20 mg/mL
• Apperance: light brown powder

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96% (HPLC)
• Empirical Formula (Hill Notation): C41H32O26 · xH2O

DETAILS

Sigma Aldrich - G7548

Biochem/physiol Actions
PGG induces predominantly (caspase dependent) apoptosis in DU145 and LNCaP cells, while inducing autophagy in more resistant PC3 and TRAMP-C2 cells. It appears that PGG targeted signaling downstream of rather than the mTOR itself. Polyphenolic pyranoses were reported (J Biol Chem. 2010, 285 (11), 7892-902) to inhibit the plasminogen activator inhibitor type 1 (PAI-1).