Details
Stereochemistry | ACHIRAL |
Molecular Formula | C7H6O5 |
Molecular Weight | 170.1195 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=CC(O)=C(O)C(O)=C1
InChI
InChIKey=LNTHITQWFMADLM-UHFFFAOYSA-N
InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
Molecular Formula | C7H6O5 |
Molecular Weight | 170.1195 |
Charge | 0 |
Count |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Gallic acid is a polyphenol found in a variety of foods and herbs. Several studies have shown thta gallic acid has neuroprotective and anti-oxidant properties and can be a promising candidate for the treatment of cancer, cardiovascular diseases, neurodegenerative disorders, fatty liver disease and many others. Gallic acid acts by protecting cells against oxidative damage caused by reactive species often encountered in biological systems including, hydroxyl, superoxide and peroxyl and the non-radicals, hydrogen peroxide and hypochlorous acid. However, its ability to induce apoptosis, is mainly associated with its prooxidant, rather than antioxidant behavior.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:1990000 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27303604 |
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Target ID: GO:0008631 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27303604 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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1.83 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285327/ |
0.3 mmol single, oral dose: 0.3 mmol route of administration: Oral experiment type: SINGLE co-administered: |
GALLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
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2.09 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285327/ |
0.3 mmol single, oral dose: 0.3 mmol route of administration: Oral experiment type: SINGLE co-administered: |
GALLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
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4.29 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285327/ |
0.3 mmol single, oral dose: 0.3 mmol route of administration: Oral experiment type: SINGLE co-administered: |
GALLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
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4.55 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285327/ |
0.3 mmol single, oral dose: 0.3 mmol route of administration: Oral experiment type: SINGLE co-administered: |
GALLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
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1.19 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285327/ |
0.3 mmol single, oral dose: 0.3 mmol route of administration: Oral experiment type: SINGLE co-administered: |
GALLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
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1.06 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285327/ |
0.3 mmol single, oral dose: 0.3 mmol route of administration: Oral experiment type: SINGLE co-administered: |
GALLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
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likely | yes (co-administration study) Comment: No Ic50/Ki value given; Coadministration with linagliptin: increase in Cmax, AUC, AUMC, AUCtotal and t1/2 of linagliptin was found to be 1.89-fold, 2.45-fold, 1.76-fold, 1.54-fold and 0.5-fold, respectively Sources: https://pubmed.ncbi.nlm.nih.gov/28766866/ |
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yes [IC50 394 uM] | ||||
yes [IC50 461 uM] |
PubMed
Title | Date | PubMed |
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Reaction rate constants of superoxide scavenging by plant antioxidants. | 2003 Dec 15 |
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Application of isomorphous replacement in the structure determination of a cubic liquid crystal phase and location of counterions. | 2003 Dec 24 |
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Epigallocatechin gallate, the main component of tea polyphenol, binds to CD4 and interferes with gp120 binding. | 2003 Nov |
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(-)-Epigallocatechin gallate causes oxidative damage to isolated and cellular DNA. | 2003 Nov 1 |
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The galloyl moiety of green tea catechins is the critical structural feature to inhibit fatty-acid synthase. | 2003 Nov 15 |
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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 |
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Effects of platelet inhibitors on propyl gallate-induced platelet aggregation, protein tyrosine phosphorylation, and platelet factor 3 activation. | 2004 Apr |
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Catechin gallates inhibit multidrug resistance (MDR) in Staphylococcus aureus. | 2004 Dec |
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Immunomodulatory activity of a new family of antioxidants obtained from grape polyphenols. | 2004 Dec 1 |
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Gallium halide induced heterocycle expansion of dihalodiphosphadiaryldiazanes [(XPNR)2] to the corresponding triphosphatriazanes [(XPNR)3]. | 2004 Dec 27 |
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Exobasidium vexans infection of Camellia sinensis increased 2,3-cis isomerisation and gallate esterification of proanthocyanidins. | 2004 Nov |
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Anti-Staphylococcus aureus activity and oxacillin resistance modulating capacity of 3-O-acyl-catechins. | 2004 Oct |
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Anticancer activity of 3-O-acyl and alkyl-(-)-epicatechin derivatives. | 2004 Oct 18 |
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Two pyranocoumarins from the seeds of Calophyllum polyanthum. | 2004 Sep |
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Phosphatidylinositol-3 kinase/Akt and GSK-3 mediated cytoprotective effect of epigallocatechin gallate on oxidative stress-injured neuronal-differentiated N18D3 cells. | 2004 Sep |
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Protective effect of epigallocatechin gallate on brain damage after transient middle cerebral artery occlusion in rats. | 2004 Sep 3 |
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Synergistic effect of green tea catechins on cell growth and apoptosis induction in gastric carcinoma cells. | 2005 Apr |
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(-)-Epigallocatechin gallate and polyphenon E inhibit growth and activation of the epidermal growth factor receptor and human epidermal growth factor receptor-2 signaling pathways in human colon cancer cells. | 2005 Apr 1 |
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The intermediate filament protein vimentin is a new target for epigallocatechin gallate. | 2005 Apr 29 |
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Epigallocatechin-3-gallate suppresses galactose-alpha1,4-galactose-1beta,4-glucose ceramide expression in TNF-alpha stimulated human intestinal epithelial cells through inhibition of MAPKs and NF-kappaB. | 2005 Aug |
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Examination of the anti-oxidative effect in renal tubular cells and apoptosis by oxidative stress. | 2005 Aug |
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Effect of new antioxidant cysteinyl-flavanol conjugates on skin cancer cells. | 2005 Aug 15 |
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Methyl gallate and chemicals structurally related to methyl gallate protect human umbilical vein endothelial cells from oxidative stress. | 2005 Aug 31 |
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Inhibitory effects of epigallocatechin gallate on compound 48/80-induced mast cell activation and passive cutaneous anaphylaxis. | 2005 Aug 31 |
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Synthesis of cyclo-2,4,6-triarsa-1,3,5-triazanes from cyclo-2,4-diarsa-1,3-diazanes demonstrating the general influence of substituent steric strain on the relative stability of pnictazane oligomers. | 2005 Aug 8 |
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Complexation of epigallocatechin gallate (a green tea extract, egcg) with Mn2+: nuclear spin relaxation by the paramagnetic ion. | 2005 Feb |
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Neuroprotective effects of (-)-epigallocatechin gallate following hypoxia-ischemia-induced brain damage: novel mechanisms of action. | 2005 Feb |
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Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives. | 2005 Feb 15 |
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Oxidation of tea extracts and tea catechins by molecular oxygen. | 2005 Jun 1 |
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Procyanidin fractions from pine (Pinus pinaster) bark: radical scavenging power in solution, antioxidant activity in emulsion, and antiproliferative effect in melanoma cells. | 2005 Jun 15 |
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In vivo effect of interleukin-1beta and interleukin-1RA on oocyte cytoplasmic maturation, ovulation, and early embryonic development in the mare. | 2005 Jun 22 |
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Structure-activity relationship of the tocopherol-regeneration reaction by catechins. | 2005 May 1 |
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Synthesis and structure identification of thiol conjugates of (-)-epigallocatechin gallate and their urinary levels in mice. | 2005 Nov |
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Bioflavonoids effectively inhibit smooth muscle cell-mediated contraction of collagen matrix induced by angiotensin II. | 2005 Nov |
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Activation of rat liver microsomal glutathione S-transferase by gallic acid. | 2005 Nov 19 |
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cGMP-independent nitric oxide signaling and regulation of the cell cycle. | 2005 Nov 3 |
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In vivo treatment of acute Chlamydia pneumoniae infection with the flavonoids quercetin and luteolin and an alkyl gallate, octyl gallate, in a mouse model. | 2005 Oct 15 |
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Molecular characterization of the gallate dioxygenase from Pseudomonas putida KT2440. The prototype of a new subgroup of extradiol dioxygenases. | 2005 Oct 21 |
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[Effect of polyphenols from the Mediterranean diet on proliferation and mediators of in vitro invasiveness of the MB-49 murine bladder cancer cell line]. | 2005 Sep |
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Kinetic study of the quenching reaction of singlet oxygen by tea catechins in ethanol solution. | 2005 Sep 15 |
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Anti-HIV protease activity from rosa family plant extracts and rosamultin from Rosa rugosa. | 2005 Spring |
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Modulation of hepatic phase II phenol sulfotransferase and antioxidant status by phenolic acids in rats. | 2006 Aug |
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A link between meiotic prophase progression and crossover control. | 2006 Feb |
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(-)-Epigallocatechin gallate attenuates acute stress responses through GABAergic system in the brain. | 2006 Feb 15 |
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Epigallocatechin gallate increases the formation of cytosolic lipid droplets and decreases the secretion of apoB-100 VLDL. | 2006 Jan |
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Novel inhibitors of fatty-acid synthase from green tea (Camellia sinensis Xihu Longjing) with high activity and a new reacting site. | 2006 Jan |
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The effect of epigallocatechin gallate on suppressing disease progression of ALS model mice. | 2006 Mar 6 |
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Effect of liposome encapsulation of tea catechins on their accumulation in basal cell carcinomas. | 2006 May |
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Involvement of p38 MAPK and Nrf2 in phenolic acid-induced P-form phenol sulfotransferase expression in human hepatoma HepG2 cells. | 2006 May |
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Dual function of (--)-epigallocatechin gallate (EGCG) in healthy human lymphocytes. | 2006 Sep 28 |
Patents
Sample Use Guides
In a preclinical study rats were treated with galic acid at a dose of 100mg/kg, p.o. for 10 days (model of vascular dementia) or with 50, 100, and 200 mg/kg, p.o. for 10 days (model of Alzheimer disease). Mice were treated with 50 and 100 mg/kg/day, orally (nonalcoholic fatty liver disease model) or with 0.3% and 1% (w/v) gallic acid until 24 weeks of age (cancer model).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24843386
In MTT assay human cervical cancer HeLa and HTB-35 cells were treated with varying concentrations (0, 10, 15, 20, 25, 30 and 40 ug/ml) of gallic acid for 24 h. Treatment of HeLa and HTB-35 human cancer cells with gallic acid decreased cell viability in a dose-dependent manner. Gallic acid reduced cell viability to 92, 84 and 66% of the control in the HeLa cells and to 94, 88 and 64% of the control in the HTB-35 cells at concentrations of 5, 10 and 15 ug/ml, respectively. At concentrations of 10, 15, and 20 ug/ml, gallic acid was able to dramatically inhibit cell migration to 73, 40 and 34% in the HeLa cells and to 45, 22 and 17% in the HTB-35 cells, respectively
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:39:03 GMT 2023
by
admin
on
Fri Dec 15 15:39:03 GMT 2023
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Record UNII |
632XD903SP
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C275
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DSLD |
1414 (Number of products:4)
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NCI_THESAURUS |
C68539
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149-91-7
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674319
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205-749-9
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1311389
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CHEMBL288114
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30778
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GALLIC ACID
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2117
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632XD903SP
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370
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632XD903SP
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100000127361
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m5645
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D005707
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DTXSID0020650
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20103
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C63648
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
1,1-Diphenyl-2-picrylhydrazyl radical scavenging assay(DPPH) IC50 expressed as ug/mL = 3.7 +/- 0.4.
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SALT/SOLVATE -> PARENT | |||
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SOLVATE->ANHYDROUS | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Gallic acid exhibited a significant free radical scavenging effect against 1,1-diphenyl-2-picryl hydrazine (DPPH) radical generation and had an inhibitory effect on lipid peroxidation, as measured by the level of malondialdehyde (MDA) formation.
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SALT/SOLVATE -> PARENT |
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METABOLITE -> PARENT |
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ACTIVE MOIETY |