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Details

Stereochemistry ABSOLUTE
Molecular Formula C41H32O26
Molecular Weight 940.6788
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENTAGALLOYLGLUCOSE

SMILES

c1c(cc(c(c1O)O)O)C(=O)OC[C@]2([H])[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])(O2)OC(=O)c3cc(c(c(c3)O)O)O)OC(=O)c4cc(c(c(c4)O)O)O)OC(=O)c5cc(c(c(c5)O)O)O)OC(=O)c6cc(c(c(c6)O)O)O

InChI

InChIKey=QJYNZEYHSMRWBK-NIKIMHBISA-N
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

HIDE SMILES / InChI

Molecular Formula C41H32O26
Molecular Weight 940.6788
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Targets

Targets

PubMed

PubMed

TitleDatePubMed
Inhibition of human immunodeficiency viral replication by tannins and related compounds.
1992 May
Prolyl endopeptidase inhibitors from the underground part of Rhodiola sachalinensis.
2001 Apr
Inhibitory effects of ellagi- and gallotannins on rat intestinal alpha-glucosidase complexes.
2001 Mar
Identification of hydrolysable tannins in the reaction zone of Eucalyptus nitens wood by high performance liquid chromatography--electrospray ionisation mass spectrometry.
2001 Mar-Apr
Seasonal variation in the content of hydrolysable tannins in leaves of Betula pubescens.
2001 May
Respiratory syncytial virus infection induces matrix metalloproteinase-9 expression in epithelial cells.
2002
1,2,3,4,6-Penta-O-galloyl-beta-D-glucose protects rat neuronal cells (Neuro 2A) from hydrogen peroxide-mediated cell death via the induction of heme oxygenase-1.
2002 Aug 9
Two new and four known polyphenolics obtained as new cell-cycle inhibitors from Rubus aleaefolius Poir.
2002 Dec
Penta-O-galloyl-beta-D-glucose inhibits the invasion of mouse melanoma by suppressing metalloproteinase-9 through down-regulation of activator protein-1.
2002 Oct 25
Oxidation of pentagalloylglucose to the ellagitannin, tellimagrandin II, by a phenol oxidase from Tellima grandiflora leaves.
2003 Feb
Inhibitory effects of the root cortex of Paeonia suffruticosa on interleukin-8 and macrophage chemoattractant protein-1 secretions in U937 cells.
2003 Jan
Paeonianins A-E, new dimeric and monomeric ellagitannins from the fruits of Paeonia lactiflora.
2003 Jun
Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 activity by 1,2,3,4,6-penta-O-galloyl-beta-D-glucose in murine macrophage cells.
2003 Oct
Antiviral compounds from traditional Chinese medicines Galla Chinese as inhibitors of HCV NS3 protease.
2004 Dec 20
Theaflavin-3,3'-digallate and penta-O-galloyl-beta-D-glucose inhibit rat liver microsomal 5alpha-reductase activity and the expression of androgen receptor in LNCaP prostate cancer cells.
2004 Jul
Penta-O-galloyl-beta-D-glucose inhibits phorbol myristate acetate-induced interleukin-8 [correction of intereukin-8] gene expression in human monocytic U937 cells through its inactivation of nuclear factor-kappaB.
2004 Mar
1,2,3,4,6-Penta-O-galloyl-beta-D-glucose blocks endothelial cell growth and tube formation through inhibition of VEGF binding to VEGF receptor.
2004 May 10
Green tea: Health benefits as cancer preventive for humans.
2005
Penta-O-galloyl-beta-D-glucose suppresses tumor growth via inhibition of angiogenesis and stimulation of apoptosis: roles of cyclooxygenase-2 and mitogen-activated protein kinase pathways.
2005 Aug
Chemical identification of the sources of commercial Fructus Chebulae.
2005 Jul-Aug
Enzymology of gallotannin and ellagitannin biosynthesis.
2005 Sep
1,2,3,4,6-penta-O-galloyl-beta-D-glucose up-regulates heme oxygenase-1 expression by stimulating Nrf2 nuclear translocation in an extracellular signal-regulated kinase-dependent manner in HepG2 cells.
2006 Jan 14
In vitro antiviral activity of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose against hepatitis B virus.
2006 Oct
The isolation of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose from Acer truncatum Bunge by high-speed counter-current chromatography.
2007 May 1
Bioactivity-guided isolation of the active compounds from Rosa nutkana and quantitative analysis of ascorbic acid by HPLC.
2007 Sep
Antioxidative activity of geranium (Pelargonium inquinans Ait) and its active component, 1,2,3,4,6-penta-O-galloyl-beta-D-glucose.
2008 Apr
Elaeocarpus sylvestris modulates gamma-ray-induced immunosuppression in mice: implications in radioprotection.
2008 Aug
1,2,3,4,6-penta-O-galloyl-beta-D-glucose from Galla Rhois protects primary rat hepatocytes from necrosis and apoptosis.
2008 Sep
Novel biological properties of Oenothera paradoxa defatted seed extracts: effects on metallopeptidase activity.
2008 Sep 10
Penta-O-galloyl-beta-D-glucose suppresses prostate cancer bone metastasis by transcriptionally repressing EGF-induced MMP-9 expression.
2009 Apr 22
Melanogenesis inhibition by gallotannins from Chinese galls in B16 mouse melanoma cells.
2009 Aug
Antioxidant and hepatoprotective activities of thai mango seed kernel extract.
2009 Aug
A traditional medicinal herb Paeonia suffruticosa and its active constituent 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose have potent anti-aggregation effects on Alzheimer's amyloid beta proteins in vitro and in vivo.
2009 Jun
1,2,3,4,6-penta-O-galloyl-beta-D-glucose attenuates renal cell migration, hyaluronan expression, and crystal adhesion.
2009 Mar 15
Penta-O-galloyl-beta-D-glucose induces S- and G(1)-cell cycle arrests in prostate cancer cells targeting DNA replication and cyclin D1.
2009 May
Tyrosinase inhibitors isolated from the roots of Paeonia suffruticosa.
2009 May-Jun
[Chemical constituents from roots of Distylium myricoides].
2009 Sep
Suppression of thymus- and activation-regulated chemokine (TARC/CCL17) production by 1,2,3,4,6-penta-O-galloyl-beta-D-glucose via blockade of NF-kappaB and STAT1 activation in the HaCaT cells.
2009 Sep 11
1,2,3,4,6-Penta-O-galloly-beta-D-glucose suppresses hypoxia-induced accumulation of hypoxia-inducible factor-1α and signaling in LNCaP prostate cancer cells.
2010
Penta-O-galloyl-beta-D-glucose induces G1 arrest and DNA replicative S-phase arrest independently of cyclin-dependent kinase inhibitor 1A, cyclin-dependent kinase inhibitor 1B and P53 in human breast cancer cells and is orally active against triple negative xenograft growth.
2010
1,2,3,4,6-penta-O-galloyl-beta-D-glucose protects splenocytes against radiation-induced apoptosis in murine splenocytes.
2010
Simple in vitro assays to identify amyloid-beta aggregation blockers for Alzheimer's disease therapy.
2010
Antioxidant effects of secondary metabolites from Geranium psilostemon.
2010 Jun
Effect of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose on elastase and hyaluronidase activities and its type II collagen expression.
2010 Mar-Apr
Intestinal alpha-glucosidase inhibitory activity and toxicological evaluation of Nymphaea stellata flowers extract.
2010 Sep 15
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Jun 26 04:58:26 UTC 2021
Edited
by admin
on Sat Jun 26 04:58:26 UTC 2021
Record UNII
3UI3K8W93I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PENTAGALLOYLGLUCOSE
Common Name English
1,2,3,4,6-PENTAKIS-O-(3,4,5-TRIHYDROXYBENZOYL)-.BETA.-D-GLUCOPYRANOSE
Systematic Name English
BETA-PENTA-O-GALLOYL-GLUCOSE
Common Name English
1,2,3,4,6-PENTAGALLOYL-.BETA.-D-GLUCOPYRANOSE
Common Name English
1,2,3,4,6-PENTA-O-GALLOYL-.BETA.-GLUCOSE
Systematic Name English
5GG
Common Name English
C04576
Code English
1,2,3,4,6-PENTA-O-GALLOYL-D-GLUCOPYRANOSE
Common Name English
1,2,3,4,6-PENTAGALLOYL GLUCOSE
Common Name English
1,2,3,4,6-PENTAGALLOYL GLUCOSE (CONSTITUENT OF BANABA LEAF) [DSC]
Common Name English
.BETA.-1,2,3,4,6-PENTAGALLOYLGLUCOSE
Common Name English
J277.746K
Code English
PENTA-O-GALLOYL-.BETA.-D-GLUCOPYRANOSE
Common Name English
GALLOTANNIN 15
Common Name English
PGG
Common Name English
PENTAGALLOYL-BETA-D-GLUCOSE
Common Name English
1,2,3,4,6-PENTA-O-GALLOYL-.BETA.-D-GLUCOPYRANOSE
Systematic Name English
PENTAGALLOYL GLUCOSE
Common Name English
1,2,3,4,6-PENTAGALLOYL-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
.BETA.-D-GLUCOPYRANOSE, 1,2,3,4,6-PENTAKIS(3,4,5-TRIHYDROXYBENZOATE)
Systematic Name English
Code System Code Type Description
FDA UNII
3UI3K8W93I
Created by admin on Sat Jun 26 04:58:26 UTC 2021 , Edited by admin on Sat Jun 26 04:58:26 UTC 2021
PRIMARY
CAS
131647-34-2
Created by admin on Sat Jun 26 04:58:26 UTC 2021 , Edited by admin on Sat Jun 26 04:58:26 UTC 2021
SUPERSEDED
CAS
102694-50-8
Created by admin on Sat Jun 26 04:58:26 UTC 2021 , Edited by admin on Sat Jun 26 04:58:26 UTC 2021
SUPERSEDED
CAS
99935-72-5
Created by admin on Sat Jun 26 04:58:26 UTC 2021 , Edited by admin on Sat Jun 26 04:58:26 UTC 2021
SUPERSEDED
CAS
14937-32-7
Created by admin on Sat Jun 26 04:58:26 UTC 2021 , Edited by admin on Sat Jun 26 04:58:26 UTC 2021
PRIMARY
CAS
98731-29-4
Created by admin on Sat Jun 26 04:58:26 UTC 2021 , Edited by admin on Sat Jun 26 04:58:26 UTC 2021
SUPERSEDED
CAS
94008-28-3
Created by admin on Sat Jun 26 04:58:26 UTC 2021 , Edited by admin on Sat Jun 26 04:58:26 UTC 2021
SUPERSEDED
PUBCHEM
65238
Created by admin on Sat Jun 26 04:58:26 UTC 2021 , Edited by admin on Sat Jun 26 04:58:26 UTC 2021
PRIMARY
Related Record Type Details
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PGG decreased the level of extracellular HBV (IC50, 1.0m g/ml) in a dose-dependent manner. PGG also reduced the HBsAg level by 25% at a concentration of 4m g/ml.
PARENT -> CONSTITUENT ALWAYS PRESENT
MIC 160 mg/L of ATCC 700392 and ATCC 700824 strains of H. pylori
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The inhibition of protein tyrosine phosphatase 1B (PTP1B) is of substantial interest for the treatment of type-2 diabetes mellitus. Using an in vitro enzyme assay with human recombinant PTP1B 1,2,3,4,6-penta-O-galloyl-D-glucopyranose(1) was isolated from the roots of Paeonia lactiflora as an inhibitor of PTP1B, with an IC50 value of 4.8 uM.