Natural Product (NP) Details

General Information of the NP (ID: NP6554)
Name
Pentagalloylglucose
Synonyms
Pentagalloylglucose; 14937-32-7; 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose; 1,2,3,4,6-Pentagalloylglucose; Pentagalloyl glucose; 1,2,3,4,6-Penta-O-galloyl-beta-D-glucose; 1,2,3,4,6-Pgg; 1,2,3,4,6-o-Pentagalloylglucose; UNII-3UI3K8W93I; 1,2,3,4,6-Pentakis-O-galloyl-beta-D-glucose; beta-D-Glucopyranose pentakis(3,4,5-trihydroxybenzoate); 3UI3K8W93I; CHEMBL382408; CHEBI:18082; DB03208; 1,2,3,4,6-pentakis-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranose; beta-Penta-O-galloyl-glucose; 1,2,3,4,6-Penta-O-galloyl-b-D-glucose; penta-O-galloyl-beta-d-glucose hydrate; beta-D-pentagalloylglucose; 1,2,3,4,6-Penta-O-galloylglucose; BETA-1,2,3,4,6-PENTA-O-GALLOYL-D-GLUCOPYRANOSE; 1,2,3,4,6-Penta-O-galloyl beta-glucopyranose; [(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate; [(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]tetrahydropyran-2-yl]methyl 3,4,5-trihydroxybenzoate; Pentagalloyl-beta-D-glucose; SCHEMBL640108; MEGxp0_001051; ACon1_000145; HY-N0527; BDBM50241052; s9399; AKOS015896803; Beta-1,2,3,4,6-Pentagalloylglucose; ZINC169292785; CCG-270584; CS-5018; NCGC00180839-01; 1,2,3,4,6-Pentagalloyl beta-D-glucose; BS-15460; N2156; 1,2,3,4,6-pentakis-O-galloyl- -D-glucose; C04576; W-2305; Q4545645; 5GG
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Species Origin Paeonia suffruticosa ...     Click to Show/Hide
Paeonia suffruticosa
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Saxifragales
Family: Paeoniaceae
Genus: Paeonia
Species: Paeonia suffruticosa
Disease Rabies virus infection [ICD-11: 1C80] Investigative [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -8.02
 
MDCK Permeability
 -4.591
 
PAMPA
 +++
 
HIA
 - - -
 
Distribution
VDss
 -0.185
 
PPB
 72.1%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 +++
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 +++
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 - - -
 
Excretion
CLplasma
 6.89
 
T1/2
 3.962
Toxicity
DILI
 +++
 
Rat Oral Acute Toxicity
 - - -
 
FDAMDD
 +++
 
Respiratory
 - - -
 
Human Hepatotoxicity
 - - -
 
Ototoxicity
 +++
 
Drug-induced Nephrotoxicity
 - - -
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 - - -
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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Formula
C41H32O26
PubChem CID
65238
Canonical SMILES
C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C(C(C(C(O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)OC(=O)C6=CC(=C(C(=C6)O)O)O
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
CAS Number
CAS 14937-32-7
ChEBI ID
CHEBI:18082
Herb ID
HBIN039151
SymMap ID
SMIT10273
TTD Drug ID
D00QDR
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          5-fluorouracil      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression ABCB1  Molecule Info 
Pathway MAP
Down-regulation Expression BAX  Molecule Info 
Pathway MAP
Up-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Down-regulation Expression C1D  Molecule Info 
Pathway MAP
Up-regulation Expression CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression CASP9  Molecule Info 
Pathway MAP
Up-regulation Expression CCNB1  Molecule Info 
Pathway MAP
Down-regulation Expression CCNE1  Molecule Info 
Pathway MAP
Up-regulation Expression IFI27  Molecule Info 
Pathway MAP
                    In-vitro Model Hep-G2 CVCL_0027 Hepatocellular carcinoma Homo sapiens
                    Experimental
                    Result(s)		 The combination significantly downregulated MDR1 and LRP1, suggesting the potential to reverse the resistance to 5-FU.
Target and Pathway
Target(s) Coagulation factor IIa (F2)  Molecule Info  [3]
Coagulation factor Xa (F10)  Molecule Info  [3]
Squalene monooxygenase (SQLE)  Molecule Info  [4]
Xanthine dehydrogenase/oxidase (XDH)  Molecule Info  [5]
BioCyc Purine nucleotides degradation Click to Show/Hide
2 Urate biosynthesis/inosine 5'-phosphate degradation
3 Guanosine nucleotides degradation
4 Adenosine nucleotides degradation
5 Retinoate biosynthesis II
KEGG Pathway Steroid biosynthesis Click to Show/Hide
2 Sesquiterpenoid and triterpenoid biosynthesis
3 Metabolic pathways
4 Biosynthesis of secondary metabolites
5 Biosynthesis of antibiotics
6 Complement and coagulation cascades
7 Purine metabolism
8 Caffeine metabolism
9 Drug metabolism - other enzymes
10 Metabolic pathways
11 Peroxisome
12 Neuroactive ligand-receptor interaction
13 Regulation of actin cytoskeleton
NetPath Pathway TCR Signaling Pathway Click to Show/Hide
Panther Pathway Blood coagulation Click to Show/Hide
2 Adenine and hypoxanthine salvage pathway
3 Purine metabolism
Pathwhiz Pathway Steroid Biosynthesis Click to Show/Hide
2 Coagulation
3 Caffeine Metabolism
4 Purine Metabolism
5 Vitamin K Metabolism
Pathway Interaction Database Beta2 integrin cell surface interactions Click to Show/Hide
2 Thrombin/protease-activated receptor (PAR) pathway
3 Angiopoietin receptor Tie2-mediated signaling
4 FOXA2 and FOXA3 transcription factor networks
5 PAR4-mediated thrombin signaling events
6 Syndecan-4-mediated signaling events
7 PAR1-mediated thrombin signaling events
Reactome Cholesterol biosynthesis Click to Show/Hide
2 Activation of gene expression by SREBF (SREBP)
3 Extrinsic Pathway of Fibrin Clot Formation
4 Intrinsic Pathway of Fibrin Clot Formation
5 Common Pathway of Fibrin Clot Formation
6 Gamma-carboxylation of protein precursors
7 Transport of gamma-carboxylated protein precursors from the endoplasmic reticulum to the Golgi apparatus
8 Removal of aminoterminal propeptides from gamma-carboxylated proteins
9 Purine catabolism
10 Cell surface interactions at the vascular wall
11 Peptide ligand-binding receptors
12 Regulation of Insulin-like Growth Factor (IGF) transport and uptake by Insulin-like Growth Factor Binding Proteins (IGFBPs)
13 G alpha (q) signalling events
14 Thrombin signalling through proteinase activated receptors (PARs)
WikiPathways Complement and Coagulation Cascades Click to Show/Hide
2 Human Complement System
3 PTM: gamma carboxylation, hypusine formation and arylsulfatase activation
4 Blood Clotting Cascade
5 Formation of Fibrin Clot (Clotting Cascade)
6 Oxidative Stress
7 Effects of Nitric Oxide
8 Metabolism of nucleotides
9 Selenium Micronutrient Network
10 Regulation of Actin Cytoskeleton
11 IL1 and megakaryotyces in obesity
12 Regulation of Insulin-like Growth Factor (IGF) Transport and Uptake by Insulin-like Growth Factor Binding Proteins (IGFBPs)
13 Gastrin-CREB signalling pathway via PKC and MAPK
14 Thrombin signalling through proteinase activated receptors (PARs)
15 Platelet Aggregation (Plug Formation)
16 GPCR ligand binding
17 GPCR downstream signaling
18 Cell surface interactions at the vascular wall
19 Folate Metabolism
20 Vitamin B12 Metabolism
References
Reference 1 Pentagalloylglucose Inhibits the Replication of Rabies Virus via Mediation of the miR-455/SOCS3/STAT3/IL-6 Pathway. J Virol. 2019 Aug 28;93(18):e00539-19.
Reference 2 Inhibitory effects and molecular mechanisms of pentagalloyl glucose in combination with 5-FU on aggressive phenotypes of HepG2 cells. Nat Prod Res. 2021 Mar;35(5):815-818.
Reference 3 Effects of tannins from Geum japonicum on the catalytic activity of thrombin and factor Xa of blood coagulation cascade. J Nat Prod. 1998 Nov;61(11):1356-60.
Reference 4 Ellagitannins and hexahydroxydiphenoyl esters as inhibitors of vertebrate squalene epoxidase. J Nat Prod. 2001 Aug;64(8):1010-4.
Reference 5 Pentagalloylglucose, a xanthine oxidase inhibitor from a Paraguayan crude drug, "Molle-i" (Schinus terebinthifolius). J Nat Prod. 1989 Jan-Feb;52(1):210-1.
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