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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-01-23 13:04:37 UTC
Update Date2019-07-23 05:47:02 UTC
HMDB IDHMDB0005807
Secondary Accession Numbers
  • HMDB05807
Metabolite Identification
Common NameGallic acid
DescriptionGallic acid, also known as gallate or gallic acid tech., belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain a 3,4,5-trihydroxybenzoic acid moiety. Gallate 1-beta-glucosyltransferase is an enzyme that uses UDP-glucose and gallate, whereas its two products are UDP and 1-galloyl-beta-D-glucose. Gallic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Gallic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, gallic acid is found, on average, in the highest concentration in a few different foods, such as mango, pomegranates, and cloves and in a lower concentration in garden tomato, banana, and spearmints. gallic acid has also been detected, but not quantified in, several different foods, such as carobs, tarragons, german camomiles, sweet basils, and cardamoms. This could make gallic acid a potential biomarker for the consumption of these foods. Gallic acid can also be used as a starting material in the synthesis of the psychedelic alkaloid mescaline. Pliny the Elder (23-79 AD) describes the use of gallic acid as a means of detecting an adulteration of verdigris and writes that it was used to produce dyes. Gallic acid was first studied by the Swedish chemist Carl Wilhelm Scheele in 1786.
Structure
Data?1563860822
Synonyms
ValueSource
3,4,5-Trihydroxybenzoic acidChEBI
Pyrogallol-5-carboxylic acidChEBI
3,4,5-TrihydroxybenzoateKegg
Pyrogallol-5-carboxylateGenerator
GallateGenerator
3,4,5-Trihydroxy-benzoateHMDB
3,4,5-Trihydroxy-benzoic acidHMDB
3,4,5-Trihydroxybenzoic acid (acd/name 4.0)HMDB
Gallic acid polymerHMDB
Gallic acid tech.HMDB
GalopHMDB
Acid, gallicHMDB
Chemical FormulaC7H6O5
Average Molecular Weight170.12
Monoisotopic Molecular Weight170.021523293
IUPAC Name3,4,5-trihydroxybenzoic acid
Traditional Namegalop
CAS Registry Number149-91-7
SMILES
OC(=O)C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
InChI KeyLNTHITQWFMADLM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain a 3,4,5-trihydroxybenzoic acid moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentGallic acids
Alternative Parents
Substituents
  • Gallic acid
  • Benzenetriol
  • Benzoic acid
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point258 - 265 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.9 mg/mL at 20 °CNot Available
LogP0.70HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility4.94 g/LALOGPS
logP1.17ALOGPS
logP0.72ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.26 m³·mol⁻¹ChemAxon
Polarizability14.75 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001i-0791200000-4d3e1baed2effb0bf15bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-053r-0491700000-68a1d17dd1d0bb6c5354JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fk9-5900000000-6b43adb858d50b520ba7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0791200000-4d3e1baed2effb0bf15bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-053r-0491700000-68a1d17dd1d0bb6c5354JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0691200000-8b11cbd28f656c4426b4JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fmi-1900000000-56bf9b5e0a68a9c0776aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00xu-4009300000-4326897e134d4856b180JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0umi-0900000000-e8e6e57cdaf8d518781aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-9600000000-8b3c3dc9e263c174a0acJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ue9-9000000000-da4704e31ba4de6b3acaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0fk9-5900000000-425a258abda96a507ea0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-951aa8106825faaca3f9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-bdedf4b4b4fd922ec704JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-5900000000-46d7a232b169910da462JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9300000000-010429242e38b1b28c13JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0g29-9100000000-fb4dc241b26c248950f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0ufr-0900000000-8e1ce790677a7c04e580JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-004i-0900000000-8999270f1e2b746047f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-880097b21bcd57ec8f77JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-bdedf4b4b4fd922ec704JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-5900000000-bf4cb2a480d9abb570d4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9300000000-63bfcc112fc600a150deJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0g29-9100000000-fb4dc241b26c248950f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-6a9289e729e66d03cf50JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-175241488c5f0956df1fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0kor-0900000000-1ceb76e12bc399878e0dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-8e403dcee60bc20ba7b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0900000000-20a78444c2179ed7730fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00os-9800000000-3011ae50626d9c15faddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-bceef5d1a34c38d340edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-0900000000-bbec391317d064ab4d89JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-8900000000-049b564c5923498a6f3eJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0fk9-2900000000-1949ca7ce1b8b610c278JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.008 +/- 0.005 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.003 +/- 0.001 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.01 +/- 0.005 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.007 +/- 0.003 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.002 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.002 +/- 0 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.001 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.005 +/- 0.004 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0-0.058 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.09 +/- 0.22 uMAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified11.874 +/- 0.353 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified12.0504 +/- 0.0588 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified12.873 +/- 1.411 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified13.873 +/- 4.526 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0267 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.213 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.107 +/- 0.160 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.110 +/- 0.130 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0533 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.073 +/- 0.06 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.019 +/- 0.052 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.38 +/- 0.092 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0473 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0617 +/- 0.0740 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.003 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413 details
UrineDetected and Quantified0.003 +/- 0.001 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.006 +/- 0.001 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID413
FoodDB IDFDB000662
KNApSAcK IDC00002647
Chemspider ID361
KEGG Compound IDC01424
BioCyc IDCPD-183
BiGG IDNot Available
Wikipedia LinkGallic_acid
METLIN ID3295
PubChem Compound370
PDB IDNot Available
ChEBI ID30778
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceCheng K F; Yip C S; Yeung H W; Kong Y C Leonurine, an improved synthesis. Experientia (1979), 35(5), 571-2. PubMed ID 446644
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bajpai B, Patil S: A new approach to microbial production of gallic acid. Braz J Microbiol. 2008 Oct;39(4):708-11. doi: 10.1590/S1517-838220080004000021. Epub 2008 Dec 1. [PubMed:24031294 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Gallic acid → 6-(5-carboxy-2,3-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Gallic acid → 6-(4-carboxy-2,6-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Gallic acid → 3,4,5-trihydroxy-6-(3,4,5-trihydroxybenzoyloxy)oxane-2-carboxylic aciddetails
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
Gallic acid → 2-{[hydroxy(3,4,5-trihydroxyphenyl)methylidene]amino}acetic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Gallic acid → 3,5-dihydroxy-4-(sulfooxy)benzoic aciddetails