Human Metabolome Database Version 3.5

Showing metabocard for Gallic acid (HMDB05807)

Record Information
Version 3.5
Creation Date 2007-01-23 06:04:37 -0700
Update Date 2013-02-08 17:14:20 -0700
HMDB ID HMDB05807
Secondary Accession Numbers None
Metabolite Identification
Common Name Gallic acid
Description Gallic 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3,4,5-Trihydroxy-Benzoate
  2. 3,4,5-Trihydroxy-Benzoic acid
  3. 3,4,5-Trihydroxybenzoate
  4. 3,4,5-Trihydroxybenzoic acid
  5. 3,4,5-Trihydroxybenzoic acid (ACD/Name 4.0)
  6. Gallate
  7. Gallic acid
  8. Gallic acid polymer
  9. Gallic acid tech.
  10. Galop
  11. Pyrogallol-5-carboxylic acid
Chemical Formula C7H6O5
Average Molecular Weight 170.1195
Monoisotopic Molecular Weight 170.021523302
IUPAC Name 3,4,5-trihydroxybenzoic acid
Traditional IUPAC Name gallic acid
CAS Registry Number 149-91-7
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 Key LNTHITQWFMADLM-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Benzoic Acid and Derivatives
Sub Class Hydroxybenzoic Acid Derivatives
Other Descriptors
  • Gallotannins(KEGG)
  • Hydroxybenzoic Acid Derivatives
  • trihydroxybenzoic acid(ChEBI)
Substituents
  • 1,2 Diphenol
  • Benzoyl
  • Carboxylic Acid
  • Phenol
  • Phenol Derivative
  • Pyrogallol Derivative
  • Resorcinol
Direct Parent Gallic Acid and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Plant
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 258 - 265 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 11.9 mg/mL at 20 °C Not Available
LogP 0.70 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 4.94 g/L ALOGPS
LogP 1.17 ALOGPS
LogP 0.72 ChemAxon
LogS -1.54 ALOGPS
pKa (strongest acidic) 3.94 ChemAxon
pKa (strongest basic) -6 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 97.99 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 39.26 ChemAxon
Polarizability 14.75 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI M-52)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.008 +/- 0.005 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.003 +/- 0.001 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.01 +/- 0.005 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.007 +/- 0.003 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.002 +/- 0 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.002 +/- 0 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.001 +/- 0 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.005 +/- 0.004 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
2.09 +/- 0.22 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
80 umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
110 umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
0.019 +/- 0.052 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.38 +/- 0.092 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.003 +/- 0 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Normal
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 413
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 413
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 413
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 413
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 413
  • Not Applicable
Urine Detected and Quantified
0.003 +/- 0.001 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
Urine Detected and Quantified
0.006 +/- 0.001 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID 413 Link_out
Phenol Explorer Metabolite ID 413 Link_out
FoodDB ID FDB000662
KNApSAcK ID C00002647 Link_out
Chemspider ID 361 Link_out
KEGG Compound ID C01424 Link_out
BioCyc ID 1-O6-O-DIGALLOYL-BETA-D-GLUCOSE Link_out
BiGG ID Not Available
Wikipedia Link Gallic acid Link_out
NuGOwiki Link HMDB05807 Link_out
Metagene Link HMDB05807 Link_out
METLIN ID 3295 Link_out
PubChem Compound 370 Link_out
PDB ID Not Available
ChEBI ID 30778 Link_out
References
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)
General References Not Available