GALLIC ACID

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)

HIDE SMILES / InChI

Molecular Formula	C7H6O5
Molecular Weight	170.1195
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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
amyloid fibril formation 7	Inhibitor 8,297
intrinsic apoptotic signaling pathway in response to oxidative stress 3	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 272	Primary	Preclinical	Unknown
Vascular dementia 11	Primary	Preclinical	Unknown
Non-alcoholic fatty liver disease 30	Primary	Preclinical	Unknown
Cancer 592	Primary	Preclinical	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1.83 μM	0.3 mmol single, oral		GALLIC ACID plasma	Homo sapiens
2.09 μM	0.3 mmol single, oral		GALLIC ACID plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
4.29 μM × h	0.3 mmol single, oral		GALLIC ACID plasma	Homo sapiens
4.55 μM × h	0.3 mmol single, oral		GALLIC ACID plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.19 h	0.3 mmol single, oral		GALLIC ACID plasma	Homo sapiens
1.06 h	0.3 mmol single, oral		GALLIC ACID plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587		inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1,461

Drug as perpetrator

Show entries

Target	Modality	Activity	Clinical evidence
P-gp 1,650	inhibitor 3,277	likely	yes (co-administration study)
CYP3A4 1,925	inhibitor 3,277	yes [IC50 394 uM]
CYP2D6 1,891	inhibitor 3,277	yes [IC50 461 uM]

Showing 1 to 3 of 3 entries

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Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:30778	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:30778
ChemicalBook	CB0158671	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0158671
eMolecules	493996	https://www.emolecules.com/cgi-bin/more?vid=493996
MolPort	MolPort-000-881-260	https://www.molport.com/shop/molecule-link/MolPort-000-881-260
ZINC	ZINC000000001504	http://zinc15.docking.org/substances/ZINC000000001504

Showing 1 to 5 of 5 entries

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PubMed

Show entries

Title	Date	PubMed
Spin-trapping study on the hydroxyl radical formed from a tea catechin-Cu(II) system.	2001 Aug	11577706
Tannic acid potently inhibits tumor cell proteasome activity, increases p27 and Bax expression, and induces G1 arrest and apoptosis.	2001 Oct	11588135
The green tea polyphenol (-)-epigallocatechin-3-gallate blocks nuclear factor-kappa B activation by inhibiting I kappa B kinase activity in the intestinal epithelial cell line IEC-6.	2001 Sep	11502884
Prooxidant action of gallic acid compounds: copper-dependent strand breaks and the formation of 8-hydroxy-2'-deoxyguanosine in DNA.	2002 Dec	12423653
Antioxidant activity of dodecyl gallate.	2002 Jun 5	12033824

Showing 1 to 5 of 18 entries

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Patents

Sample Use Guides

In Vivo Use Guide

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

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