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14937-32-7(anhydrous) molecular structure
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[(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 and InChIs

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

Cite this record

CBID:154834 http://www.chembase.cn/molecule-154834.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
14937-32-7(anhydrous)
MDL Number
MFCD03788860
PubChem SID
162248972
PubChem CID
65238

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
G7548 external link Add to cart Please log in.
Data Source Data ID
PubChem 65238 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
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 cm3 Polarizability 82.56463 Å3
Polar Surface Area 444.18 Å2 Rotatable Bonds 16 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO: ≥20 mg/mL expand Show data source
Apperance
light brown powder expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥96% (HPLC) expand Show data source
Empirical Formula (Hill Notation)
C41H32O26 · xH2O expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - G7548 external link
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).

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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