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Bovine Metabolome Database



Showing metabocard for Gentisic acid (BMDB00152)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:43
Accession Number BMDB00152
Common Name Gentisic acid
Description Gentisic acid is a dihydroxybenzoic acid. It is a crystalline powder that forms monoclinic prism in water solution. Gentisic acid is an active metabolite of salicylic acid degradation. There is an increasing amount of evidence indicating that gentisic acid has a broad spectrum of biological activity, such as anti-inflammatory, antirheumatic and antioxidant properties. Gentisic acid is also a byproduct of tyrosine and benzoate metabolism.
Synonyms
  1. 2,5-Dihydroxybenzoate
  2. 2,5-Dihydroxybenzoic acid
  3. 2,5-Dioxybenzoate
  4. 2,5-Dioxybenzoic acid
  5. 3,6-Dihydroxybenzoate
  6. 3,6-Dihydroxybenzoic acid
  7. 5-Hydroxysalicylate
  8. 5-Hydroxysalicylic acid
  9. 5-hydroxy-Salicylate
  10. 5-hydroxy-Salicylic acid
  11. Carboxyhydroquinone
  12. Dihydroxybenzoicacid
  13. Gensigen
  14. Gensigon
  15. Gentisate
  16. Gentisic acid
  17. Gentisinate
  18. Gentisinic acid
  19. Hydroquinonecarboxylate
  20. Hydroquinonecarboxylic acid
Chemical IUPAC Name 2,5-dihydroxybenzoic acid
Chemical Formula C7H6O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Aromatic Acids
Sub Class
  • Phenolic acids
Family
  • Mammalian_Metabolite
Species
  • phenol or hydroxyhetarene; carboxylic acid; aromatic compound
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 154.120
Monoisotopic Molecular Weight 154.026611
Isomeric SMILES OC(=O)C1=CC(O)=CC=C1O
Canonical SMILES OC(=O)C1=CC(O)=CC=C1O
KEGG Compound ID C00628 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Gentisic acid Link Image
METLIN ID 618 Link Image
PubChem Compound 3469 Link Image
PubChem Substance 11335713 Link Image
ChEBI ID 17189 Link Image
CAS Registry Number 490-79-9
InChI Identifier InChI=1/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
Synthesis Reference Morris, Steward G. Preparation of gentisic acid and its fatty alcohol esters.Journal of the American Chemical Society (1949), 71 2056-7
Melting Point (Experimental) 199.5 oC
Experimental Water Solubility 5.0 mg/mL at 5 oC [MERCK (1989)] Source: PhysProp
Predicted Water Solubility 12.3 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity 1.74 [SANGSTER (1994)] Source: PhysProp
Predicted LogP/Hydrophobicity 1.23 [Predicted by ALOGPS]; 1.386 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Tyrosine Metabolism
HMDB Pathways
Name Tyrosine Metabolism
Image Show Link Image
KEGG Pathways
Name Tyrosine Metabolism
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SimCell Pathways
Name Tyrosine Metabolism
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Graph
SBML
General References
  1. Wikipedia Link Image