PENTAGALLOYLGLUCOSE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C41H32O26
Molecular Weight	940.6772
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC(=CC(O)=C1O)C(=O)OC[C@H]2O[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@@H](OC(=O)C5=CC(O)=C(O)C(O)=C5)[C@@H]2OC(=O)C6=CC(O)=C(O)C(O)=C6

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	940.6772
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
viral genome replication 4 Target ID: GO:0019079 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21479599 \| https://www.ncbi.nlm.nih.gov/pubmed/26166506	Inhibitor 8297

PubMed

Title	Date	PubMed
Inhibition of human immunodeficiency viral replication by tannins and related compounds.	1992 May	1416904
Respiratory syncytial virus infection induces matrix metalloproteinase-9 expression in epithelial cells.	2002	11890521
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	12133584
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	12398898
Inhibitory effects of the root cortex of Paeonia suffruticosa on interleukin-8 and macrophage chemoattractant protein-1 secretions in U937 cells.	2003 Jan	12499080
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	14609132
Antiviral compounds from traditional Chinese medicines Galla Chinese as inhibitors of HCV NS3 protease.	2004 Dec 20	15546725
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	14963012
Novel lipid-peroxidation- and cyclooxygenase-inhibitory tannins from Picrorhiza kurroa seeds.	2004 Mar	17191857
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	15037215
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	15105050
In vitro anti-HCV activities of Saxifraga melanocentra and its related polyphenolic compounds.	2005	16329286
Green tea: Health benefits as cancer preventive for humans.	2005	15889414
Chemical identification of the sources of commercial Fructus Chebulae.	2005 Jul-Aug	16042149
Phenolic constituents of galla Rhois with hepatoprotective effects on tacrine- and nitrofurantoin-induced cytotoxicity in Hep G2 cells.	2005 Nov	16272710
Protein binding and astringent taste of a polymeric procyanidin, 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose, castalagin, and grandinin.	2006 Dec 13	17147439
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	16482620
In vitro antiviral activity of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose against hepatitis B virus.	2006 Oct	17015965
Elastin stabilization for treatment of abdominal aortic aneurysms.	2007 Apr 3	17372168
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	17141590
Bioactivity-guided isolation of the active compounds from Rosa nutkana and quantitative analysis of ascorbic acid by HPLC.	2007 Sep	18066132
Antioxidative activity of geranium (Pelargonium inquinans Ait) and its active component, 1,2,3,4,6-penta-O-galloyl-beta-D-glucose.	2008 Apr	18386256
Elaeocarpus sylvestris modulates gamma-ray-induced immunosuppression in mice: implications in radioprotection.	2008 Aug	18570220
1,2,3,4,6-penta-O-galloyl-beta-D-glucose from Galla Rhois protects primary rat hepatocytes from necrosis and apoptosis.	2008 Sep	18622905
Novel biological properties of Oenothera paradoxa defatted seed extracts: effects on metallopeptidase activity.	2008 Sep 10	18707116
Melanogenesis inhibition by gallotannins from Chinese galls in B16 mouse melanoma cells.	2009 Aug	19652388
Tyrosinase inhibitors isolated from the roots of Paeonia suffruticosa.	2009 May-Jun	19586602
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	21048308
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	20809980
1,2,3,4,6-penta-O-galloyl-beta-D-glucose protects splenocytes against radiation-induced apoptosis in murine splenocytes.	2010	20606300
Simple in vitro assays to identify amyloid-beta aggregation blockers for Alzheimer's disease therapy.	2010	20061605
Antioxidant effects of secondary metabolites from Geranium psilostemon.	2010 Jun	20614819
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	20369791
Intestinal alpha-glucosidase inhibitory activity and toxicological evaluation of Nymphaea stellata flowers extract.	2010 Sep 15	20600753

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:04:51 GMT 2023` Edited by `admin` on `Sat Dec 16 09:04:51 GMT 2023`
Record UNII	3UI3K8W93I
Record Status	`Validated (UNII)`
Record Version

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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