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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-01-23 13:04:37 UTC
Update Date2021-09-07 17:05:25 UTC
HMDB IDHMDB0005807
Secondary Accession Numbers
  • HMDB05807
Metabolite Identification
Common NameGallic acid
DescriptionGallic acid is an 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)3CO2H. Gallic acid is widely distributed in plants and is found both free and as part of tannins. It is commonly used in the pharmaceutical industry. Gallic acid can also be used to synthesize the hallucinogenic alkaloid mescaline, also known as 3,4,5-trimethoxyphenethylamine. Salts and esters of gallic acid are termed gallates. Gallic acid has been found to be s metabolite of Aspergillus (PMID:24031294 ).
Structure
Data?1582752366
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
3,4,5-Hydroxybenzoic acidPhytoBank
Gallic acidHMDB
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 Molecular 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 Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M+H]+ExperimentalNot Available130.892http://allccs.zhulab.cn/database/detail?ID=AllCCS00000889
DarkChem[M+H]+PredictedNot Available136.83631661259
DarkChem[M-H]-PredictedNot Available132.27431661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Gallic acid,1TMS,#12023.1088https://arxiv.org/abs/1905.12712
Gallic acid,1TMS,#21918.8878https://arxiv.org/abs/1905.12712
Gallic acid,1TMS,#31950.751https://arxiv.org/abs/1905.12712
Gallic acid,2TMS,#11926.6732https://arxiv.org/abs/1905.12712
Gallic acid,2TMS,#21933.3875https://arxiv.org/abs/1905.12712
Gallic acid,2TMS,#31915.6752https://arxiv.org/abs/1905.12712
Gallic acid,2TMS,#41882.9236https://arxiv.org/abs/1905.12712
Gallic acid,3TMS,#11978.3196https://arxiv.org/abs/1905.12712
Gallic acid,3TMS,#21924.2097https://arxiv.org/abs/1905.12712
Gallic acid,3TMS,#31906.7876https://arxiv.org/abs/1905.12712
Gallic acid,4TMS,#11977.4038https://arxiv.org/abs/1905.12712
Gallic acid,1TBDMS,#12297.1265https://arxiv.org/abs/1905.12712
Gallic acid,1TBDMS,#22237.9602https://arxiv.org/abs/1905.12712
Gallic acid,1TBDMS,#32253.1914https://arxiv.org/abs/1905.12712
Gallic acid,2TBDMS,#12443.878https://arxiv.org/abs/1905.12712
Gallic acid,2TBDMS,#22473.93https://arxiv.org/abs/1905.12712
Gallic acid,2TBDMS,#32457.6138https://arxiv.org/abs/1905.12712
Gallic acid,2TBDMS,#42447.0332https://arxiv.org/abs/1905.12712
Gallic acid,3TBDMS,#12647.3005https://arxiv.org/abs/1905.12712
Gallic acid,3TBDMS,#22625.6208https://arxiv.org/abs/1905.12712
Gallic acid,3TBDMS,#32676.813https://arxiv.org/abs/1905.12712
Gallic acid,4TBDMS,#12844.7546https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001i-0791200000-4d3e1baed2effb0bf15b2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-053r-0491700000-68a1d17dd1d0bb6c53542014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fk9-5900000000-6b43adb858d50b520ba72017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0791200000-4d3e1baed2effb0bf15b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-053r-0491700000-68a1d17dd1d0bb6c53542017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0691200000-8b11cbd28f656c4426b42017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fmi-1900000000-56bf9b5e0a68a9c0776a2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00xu-4009300000-4326897e134d4856b1802017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0fk9-2900000000-1949ca7ce1b8b610c2782015-03-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb62021-09-18View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312ab2021-09-18View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0umi-0900000000-e8e6e57cdaf8d518781a2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-9600000000-8b3c3dc9e263c174a0ac2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ue9-9000000000-da4704e31ba4de6b3aca2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0fk9-5900000000-425a258abda96a507ea02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-951aa8106825faaca3f92012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-bdedf4b4b4fd922ec7042012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-5900000000-46d7a232b169910da4622012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9300000000-010429242e38b1b28c132012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0g29-9100000000-fb4dc241b26c248950f72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0ufr-0900000000-8e1ce790677a7c04e5802017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-004i-0900000000-8999270f1e2b746047f72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-880097b21bcd57ec8f772017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-bdedf4b4b4fd922ec7042017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-5900000000-bf4cb2a480d9abb570d42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9300000000-63bfcc112fc600a150de2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0g29-9100000000-fb4dc241b26c248950f72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-6a9289e729e66d03cf502017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-175241488c5f0956df1f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0kor-0900000000-1ceb76e12bc399878e0d2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-8e403dcee60bc20ba7b42016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0900000000-20a78444c2179ed7730f2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00os-9800000000-3011ae50626d9c15fadd2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-bceef5d1a34c38d340ed2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-0900000000-bbec391317d064ab4d892016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-8900000000-049b564c5923498a6f3e2016-09-12View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, experimental)2015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)2015-03-12View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
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
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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 QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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 but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413 details
UrineExpected but not QuantifiedNot QuantifiedNot 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 QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB 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
MarkerDB IDMDB00000474
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