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Record Information
Version4.0
Creation Date2007-01-23 13:04:37 UTC
Update Date2017-09-25 21:19:49 UTC
HMDB IDHMDB0005807
Secondary Accession Numbers
  • HMDB05807
StatusDetected and Quantified
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 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. (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
3,4,5-Trihydroxybenzoic acidChEBI
Pyrogallol-5-carboxylic acidChEBI
3,4,5-TrihydroxybenzoateGenerator
GallateGenerator
Pyrogallol-5-carboxylateGenerator
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, gallicMeSH
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
DescriptionThis compound 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
Biological Location:
Source:
Biofluid and excreta:
Biological:
Plant:
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.26 m3·mol-1ChemAxon
Polarizability14.75 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-001i-0791200000-4d3e1baed2effb0bf15bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-053r-0491700000-68a1d17dd1d0bb6c5354View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-0fk9-5900000000-6b43adb858d50b520ba7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-001i-0791200000-4d3e1baed2effb0bf15bView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-053r-0491700000-68a1d17dd1d0bb6c5354View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-001i-0691200000-8b11cbd28f656c4426b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0umi-0900000000-e8e6e57cdaf8d518781aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-9600000000-8b3c3dc9e263c174a0acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ue9-9000000000-da4704e31ba4de6b3acaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0fk9-5900000000-425a258abda96a507ea0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-951aa8106825faaca3f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-bdedf4b4b4fd922ec704View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-5900000000-46d7a232b169910da462View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9300000000-010429242e38b1b28c13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0g29-9100000000-fb4dc241b26c248950f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , PositiveNot Available
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , NegativeNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-880097b21bcd57ec8f77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-bdedf4b4b4fd922ec704View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-5900000000-bf4cb2a480d9abb570d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9300000000-63bfcc112fc600a150deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0g29-9100000000-fb4dc241b26c248950f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-6a9289e729e66d03cf50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-175241488c5f0956df1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0kor-0900000000-1ceb76e12bc399878e0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0fk9-2900000000-1949ca7ce1b8b610c278View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 +/- 0 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.002 +/- 0 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.001 +/- 0 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.005 +/- 0.004 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.09 +/- 0.22 uMAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified11.874 +/- 0.353 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified12.0504 +/- 0.0588 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified12.873 +/- 1.411 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified13.873 +/- 4.526 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
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 +/- 0 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 +/- 0 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
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID413
Phenol Explorer Metabolite ID413
FoodDB IDFDB000662
KNApSAcK IDC00002647
Chemspider ID361
KEGG Compound IDC01424
BioCyc IDCPD-183
BiGG IDNot Available
Wikipedia LinkGallic acid
NuGOwiki LinkHMDB0005807
METLIN ID3295
PubChem Compound370
PDB IDNot Available
ChEBI ID30778
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 ReferencesNot Available