Gallic acid (PAMDB000452)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000452
Identification
Name: Gallic acid
Description:Gallic acid (GA) 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. Plants, bacteria and fungi are capable of synthesizing gallic acid. Shikimate dehydrogenase (SDH), a shikimate pathway enzyme essential for aromatic amino acid synthesis, is required for gallic acid production in Pseudomonas aeruginosa. SDH catalyzes NADPH-dependent reduction of 3-DHS (3-dehydroshikimate) to shikimic acid (SA), which is ultimately used to produce the aromatic amino acids l-tyrosine, l-tryptophan, and l-phenylalanine. SDH also catalyzes NADP+-dependent dehydrogenation of SA to 3-DHS, but also the dehydrogenation of 3-DHS to GA.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 3,4,5-Trihydroxy-Benzoate
  • 3,4,5-Trihydroxy-Benzoic acid
  • 3,4,5-Trihydroxybenzoate
  • 3,4,5-Trihydroxybenzoate (acd/name 4.0)
  • 3,4,5-Trihydroxybenzoic acid
  • 3,4,5-trihydroxybenzoic acid (ACD/Name 4.0)
  • Gallate
  • Gallate polymer
  • Gallate tech.
  • Gallic acid
  • Gallic acid polymer
  • Gallic acid tech.
  • Galop
  • Pyrogallol-5-carboxylate
  • Pyrogallol-5-carboxylic acid
Chemical Formula: C7H6O5
Average Molecular Weight: 170.1195
Monoisotopic Molecular Weight: 170.021523302
InChI Key: LNTHITQWFMADLM-UHFFFAOYSA-N
InChI:InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
CAS number: 149-91-7
IUPAC Name:3,4,5-trihydroxybenzoic acid
Traditional IUPAC Name: galop
SMILES:OC(=O)C1=CC(O)=C(O)C(O)=C1
Chemical Taxonomy
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.
Kingdom Organic compounds
Super ClassBenzenoids
Class Benzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct Parent Gallic acids
Alternative Parents
Substituents
  • Gallic acid
  • Pyrogallol derivative
  • Benzoic acid
  • Benzenetriol
  • 1,2-diphenol
  • Benzoyl
  • Phenol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular Framework Aromatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 258-265 °C
Experimental Properties:
PropertyValueSource
Water Solubility:11.9 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:0.70 [HANSCH,C ET AL. (1995)]PhysProp
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
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
  • 1,4-Dichlorobenzene degradation pae00627
  • Microbial metabolism in diverse environments pae01120
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
GC-MSGC-MS Spectrum - GC-MSNot Available
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
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
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference: Cheng 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)
External Links:
ResourceLink
CHEBI ID30778
HMDB IDHMDB05807
Pubchem Compound ID370
Kegg IDC01424
ChemSpider ID361
WikipediaGallic acid
BioCyc IDCPD-183
EcoCyc IDCPD-183