Classification Term: 3377

Gallic acid and derivatives (ontology term: CHEMONTID:0001251)

Compounds containing a 3,4,5-trihydroxybenzoic acid moiety." []

found 21 associated metabolites at family metabolite taxonomy ontology rank level.

Ancestor: Hydroxybenzoic acid derivatives

Child Taxonomies: Gallic acids, Galloyl esters

Leonurine

Benzoic acid, 4-hydroxy-3,5-dimethoxy-, 4-((aminoiminomethyl)amino)butyl ester

C14H21N3O5 (311.1481136)


Leonurine is a trihydroxybenzoic acid. Leonurine is a natural product found in Leonotis leonurus and Leonurus sibiricus with data available. Leonurine is an alkaloid isolated from Leonurus artemisia, with anti-oxidative and anti-inflammatory. Leonurine is an alkaloid isolated from Leonurus artemisia, with anti-oxidative and anti-inflammatory.

   

Syringic acid

InChI=1/C9H10O5/c1-13-6-3-5(9(11)12)4-7(14-2)8(6)10/h3-4,10H,1-2H3,(H,11,12

C9H10O5 (198.052821)


Syringic acid, also known as syringate or cedar acid, belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. Outside of the human body, Syringic acid is found, on average, in the highest concentration within a few different foods, such as common walnuts, swiss chards, and olives and in a lower concentration in apples, tarragons, and peanuts. Syringic acid has also been detected, but not quantified in several different foods, such as sweet marjorams, silver lindens, bulgurs, annual wild rices, and barley. This could make syringic acid a potential biomarker for the consumption of these foods. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. Research suggests that phenolics from wine may play a positive role against oxidation of low-density lipoprotein (LDL), which is a key step in the development of atherosclerosis. Syringic acid is a phenol present in some distilled alcohol beverages. It is also a product of microbial (gut) metabolism of anthocyanins and other polyphenols that have been consumed (in fruits and alcoholic beverages - PMID:18767860). Syringic acid is also a microbial metabolite that can be found in Bifidobacterium (PMID:24958563). Syringic acid is a dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid. It has a role as a plant metabolite. It is a member of benzoic acids, a dimethoxybenzene and a member of phenols. It is functionally related to a gallic acid. It is a conjugate acid of a syringate. Syringic acid is a natural product found in Visnea mocanera, Pittosporum illicioides, and other organisms with data available. Syringic acid is a metabolite found in or produced by Saccharomyces cerevisiae. Present in various plants free and combined, e.g. principal phenolic constituent of soyabean meal (Glycine max) A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents KEIO_ID S018 Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation.

   

Eudesmic acid

Trimebutine Imp. B (EP); Trimethoprim Imp. J (EP); 3,4,5-Trimethoxybenzoic Acid; Trimebutine Maleate Impurity B; Trimethoprim Impurity J

C10H12O5 (212.06847019999998)


3,4,5-trimethoxybenzoic acid is a benzoic acid derivative carrying 3-, 4- and 5-methoxy substituents. It has a role as a plant metabolite, a human xenobiotic metabolite and a human urinary metabolite. It is a member of benzoic acids and a member of methoxybenzenes. It is functionally related to a benzoic acid. It is a conjugate acid of a 3,4,5-trimethoxybenzoate. 3,4,5-Trimethoxybenzoic acid is a natural product found in Verbesina myriocephala, Engelhardia roxburghiana, and other organisms with data available. Eudesmic acid is found in olive. Eudesmic acid is isolated from eucalyptus oil etc. A benzoic acid derivative carrying 3-, 4- and 5-methoxy substituents. Isolated from eucalyptus oil etc. Eudesmic acid is found in olive. 3,4,5-Trimethoxybenzoic acid (Eudesmic acid;Trimethylgallic Acid) is a benzoic acid derivative. A building block in medicine and organic synthesis. 3,4,5-Trimethoxybenzoic acid (Eudesmic acid;Trimethylgallic Acid) is a benzoic acid derivative. A building block in medicine and organic synthesis.

   

Ethyl 3,4,5-trimethoxybenzoate

3,4,5-Trimethoxybenzoic Acid Ethyl Ester

C12H16O5 (240.0997686)


Ethyl 3,4,5-trimethoxybenzoate is isolated from cashew gum. Ethyl 3,4,5-trimethoxybenzoate is a trihydroxybenzoic acid. Isolated from cashew gum Ethyl 3,4,5-trimethoxybenzoate is a natural compound isolated from the roots of Rauvolfia yunnanensis Tsiang[1].

   

3-Methoxy-4,5-methylenedioxybenzoic acid

7-methoxy-2H-1,3-benzodioxole-5-carboxylic acid

C9H8O5 (196.0371718)


3-Methoxy-4,5-methylenedioxybenzoic acid is found in green vegetables. 3-Methoxy-4,5-methylenedioxybenzoic acid is isolated from seeds of Apium graveolen

   

4-O-Methylgallic acid

3,5-Dihydroxy-4-methoxy-benzoic acid

C8H8O5 (184.0371718)


4-O-Methyl gallic acid (4-OMGA) has first been identified as a major methyl derivative of gallic acid in human plasma and urine. More recently, 4-O-methyl gallic acid (4-OMGA) has been found in urine during regular black tea ingestion and in plasma after moderate red wine consumption. PMID: 15527792. 4-O-methylgallic acid (4-OMGA), a major metabolite of gallic acid abundant in red wine. 4-OMGA inhibited the expression of intercellular adhesion molecule-1(ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1) in human umbilical vein endothelial cells (HUVECs) stimulated with tumor necrosis factor-alpha (TNF-alpha), resulting in the suppression of leukocyte adhesion to HUVECs (PMID: 17027748). 4-O-Methyl gallic acid has been found to be a metabolite of Beauveria and Pantoea (PMID: 17111140) (https://www.researchgate.net/publication/275561863_Microbial_Degradation_of_Bergenin_a_Phenolic_C-Glucoside). 4-O-Methyl gallic acid (4-OMGA) has first been identified as a major methyl derivative of gallic acid in human plasma and urine. More recently, 4-O-methyl gallic acid (4-OMGA) has been found in urine during regular black tea ingestion and in plasma after moderate red wine consumption. PMID: 15527792

   

3,4-O-Dimethylgallic acid

3-Hydroxy-4,5-dimethoxybenzoic acid

C9H10O5 (198.052821)


3,4-O-Dimethylgallic acid is a polyphenol metabolite detected in biological fluids (PMID: 20428313). A polyphenol metabolite detected in biological fluids [PhenolExplorer]

   

3'-O-Methylepicatechin 7-O-glucuronide

(2S,3S,4S,5R,6S)-6-{[(2R,3R)-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

C22H24O12 (480.1267704)


3-O-Methylepicatechin 7-O-glucuronide (3ME7G) belongs to the class of organic compounds known as flavonoid-7-O-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. 3-O-Methyl-(-)-epicatechin 7-O-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). (−)-Epicatechin is taken up by HUVECs (i.e. endothelial cells) and intracellularly metabolized into 3ME7G and 3-O-methylepicatechin 7-O-sulfate (3ME7S) (PMID: 24717599). 3ME7G is a polyphenol metabolite detected in biological fluids (PMID: 20428313).

   

Methylgallic acid-O-sulphate

(3,4,5-Trihydroxy-2-methylbenzoyloxy)sulphonic acid

C8H8O8S (263.9939888)


Methylgallic acid-O-sulphate is a conjugate of methylgallic acid and sulphate. methylgallic acid is a methyl ester of gallic acid. Gallic acid is a trihydroxybenzoic acid, a type of phenolic acid, a type of organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula is C6H2(OH)3COOH. Gallic acid is found both free and as part of hydrolyzable tannins. (Wikipedia)

   

3,5-dihydroxy-4-(sulfooxy)benzoic acid

3,5-Dihydroxy-4-(sulphooxy)benzoic acid

C7H6O8S (249.9783396)


3,5-dihydroxy-4-(sulfooxy)benzoic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3,4,5-trihydroxybenzoic acid. It is generated by Sulfotransferase 1A3 (P0DMM9) and Sulfotransferase enzymes via a -4-O-sulfation-of-phenolic-compound reaction. This -4-O-sulfation-of-phenolic-compound occurs in humans.

   

3,5-dimethoxy-4-(sulfooxy)benzoic acid

3,5-Dimethoxy-4-(sulphooxy)benzoic acid

C9H10O8S (278.00963800000005)


3,5-dimethoxy-4-(sulfooxy)benzoic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 4-hydroxy-3,5-dimethoxybenzoic acid. It is generated by Sulfotransferase 1A3 (P0DMM9) and Sulfotransferase enzymes via a -4-O-sulfation-of-phenolic-compound reaction. This -4-O-sulfation-of-phenolic-compound occurs in humans.

   

4-Methylgallic acid 3-sulfate

3-Hydroxy-4-methoxy-5-(sulfooxy)benzoic acid

C8H8O8S (263.9939888)


4-o-methylgallic acid 3-o-sulphate belongs to gallic acid and derivatives class of compounds. Those are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. 4-o-methylgallic acid 3-o-sulphate is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa).

   

Ethyl gallate 3-sulfate

[5-(Ethoxycarbonyl)-2,3-dihydroxyphenyl]oxidanesulphonic acid

C9H10O8S (278.00963800000005)


   

Gallic acid 3-sulfate

3,4-dihydroxy-5-(sulfooxy)benzoic acid

C7H6O8S (249.9783396)


   

bergenin

5,6,12,14-tetrahydroxy-4-(hydroxymethyl)-13-methoxy-3,8-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(14),10,12-trien-9-one

C14H16O9 (328.0794286)


   

Dilazep

3-[4-[3-(3,4,5-Trimethoxybenzoyl)oxypropyl]-1,4-diazepan-1-yl]propyl 3,4,5-trimethoxybenzoic acid

C31H44N2O10 (604.2995804)


C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C87053 - Adrenergic Agonist C - Cardiovascular system > C01 - Cardiac therapy > C01D - Vasodilators used in cardiac diseases D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents

   

Hexobendine

3-[Methyl(2-{methyl[3-(3,4,5-trimethoxybenzoyloxy)propyl]amino}ethyl)amino]propyl 3,4,5-trimethoxybenzoic acid

C30H44N2O10 (592.2995804)


C - Cardiovascular system > C01 - Cardiac therapy > C01D - Vasodilators used in cardiac diseases C78274 - Agent Affecting Cardiovascular System > C29707 - Vasodilating Agent D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents

   

Methyl syringate

Methyl 4-hydroxy-3,5-dimethoxybenzoic acid

C10H12O5 (212.06847019999998)


Methyl syringate, a chemical marker of asphodel monofloral honey, is an efficient phenolic mediator for bacterial and fungal laccases. Methyl syringate is a TRPA1 agonist[1][2][3]. Methyl syringate, a chemical marker of asphodel monofloral honey, is an efficient phenolic mediator for bacterial and fungal laccases. Methyl syringate is a TRPA1 agonist[1][2][3].

   

N-Desmethyltrimebutine

Benzoic acid, 3,4,5-trimethoxy-, 2-(methylamino)-2-phenylbutyl ester

C21H27NO5 (373.18891320000006)


   

Pirozadil

{6-[(3,4,5-trimethoxybenzoyloxy)methyl]pyridin-2-yl}methyl 3,4,5-trimethoxybenzoic acid

C27H29NO10 (527.1791374000001)


   

trimebutine

2-(Dimethylamino)-2-phenylbutyl 3,4,5-trimethoxybenzoic acid

C22H29NO5 (387.20456240000004)


A - Alimentary tract and metabolism > A03 - Drugs for functional gastrointestinal disorders > A03A - Drugs for functional gastrointestinal disorders > A03AA - Synthetic anticholinergics, esters with tertiary amino group D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist D005765 - Gastrointestinal Agents Trimebutine is a drug with antimuscarinic and weak mu opioid agonist effects. Target: Opioid Receptor Trimebutine is an agonist of peripheral mu, kappa and delta opiate receptors, used as spasmolytic agent for treatment of both acute and chronic abdominal pain [1]. The major product from drug metabolism of trimebutine in human beings is nor-trimebutine, which comes from removal of one of the methyl groups attached to nitrogen. Trimebutine exerts its effects in part due to causing a premature activation of phase III of the migrating motor complex in the digestive tract [2, 3].