GABAReceptorInhibitorgabareceptorinhibitor

Gentisic acid

By rofalproject
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. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 2,5-DihydroxybenzoateChEBI 5-Hydroxysalicylic acidChEBI GentisateChEBI Hydroquinonecarboxylic acidChEBI 2,5-Dihydroxybenzoic acidGenerator 5-HydroxysalicylateGenerator HydroquinonecarboxylateGenerator 2,5-DioxybenzoateHMDB 2,5-Dioxybenzoic acidHMDB 3,6-DihydroxybenzoateHMDB 3,6-Dihydroxybenzoic acidHMDB 5-Hydroxy-salicylateHMDB 5-Hydroxy-salicylic acidHMDB CarboxyhydroquinoneHMDB DihydroxybenzoicacidHMDB GensigenHMDB GensigonHMDB GentisinateHMDB Gentisinic acidHMDB 2,5-Dihydroxybenzoic acid, monosodium saltMeSH Lithium 2,5-dihydroxybenzoateMeSH

Chemical Formlia

C7H6O4 Average Molecliar Weight

154.121 Monoisotopic Molecliar Weight

154.026608673 IUPAC Name

2,5-dihydroxybenzoic acid Traditional Name

2,5-dihydroxybenzoic acid CAS Registry Number

490-79-9 SMILES

OC(=O)C1=C(O)C=CC(O)=C1

InChI Identifier

InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)

InChI Key

WXTMDXOMEHJXQO-UHFFFAOYSA-N Chemical Taxonomy Classification

Not classified Ontology Status

Detected and Quantified Origin

  • Endogenous

    • Biofunction

    Not Available Application

    Not Available Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point199.5 °CNot Available Boiling PointNot AvailableNot Available Water Solubility5.0 mg/mL at 5 °CNot Available LogP1.74SANGSTER (1994)

    Predicted Properties

    Property Value Source Water Solubility12.3 mg/mLALOGPS logP1.23ALOGPS logP1.67ChemAxon logS-1.1ALOGPS pKa (Strongest Acidic)2.53ChemAxon pKa (Strongest Basic)-5.9ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area77.76 Å2ChemAxon Rotatable Bond Count1ChemAxon Refractivity37.28 m3·mol-1ChemAxon Polarizability13.78 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key GC-MS

    GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0a4i-0849000000-d6f7b541cabdb5e20dd6View in MoNA GC-MS

    GC-MS Spectrum – GC-MS (3 TMS)splash10-0a4i-3955000000-215d684d2fae395f2e76View in MoNA GC-MS

    GC-MS Spectrum – EI-Bsplash10-03di-2009080030-be174b5f8728c96650e7View in MoNA GC-MS

    GC-MS Spectrum – EI-Bsplash10-0a4i-0229000000-a4712abe7c7db86a97beView in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOFsplash10-0a4i-1946000000-be25f693c540abb01bdeView in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOFsplash10-0a4i-1946000000-be25f693c540abb01bdeView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-0900000000-816a84a65cefa1b31731View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-1900000000-977e85749e8fa31315c5View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-1900000000-086d66fbe2d41a2d725cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-e3a62163a69461ab2cffView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-0900000000-06431a9cf0c877732fe5View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-0900000000-e938fddf26a9bb2cd9e3View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-0900000000-38ef6d9660431bec9b3bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-0900000000-ac95d834c95477f325a7View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Positivesplash10-004r-1913000000-eba82100caa3c2664508View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negativesplash10-0udi-0902000000-6cc114aa94b58c53c123View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Positivesplash10-0k9i-0930000000-4388abc8fe86bc940e89View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negativesplash10-0udi-0901000000-077381dba9d80706a097View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Positivesplash10-0fri-0930000000-4e24b1261f33fba704e2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000b-9800000000-35424c6ac43370b30b89View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0900000000-56fe39ec90c2e54662dbView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-TOF , negativesplash10-0a4i-0900000000-a0b5d2185d831113c59aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-TOF , negativesplash10-0a4i-0900000000-ddf5ec6162fb4b835c3aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-TOF , negativesplash10-0a4i-0900000000-ddf5ec6162fb4b835c3aView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available MS

    Mass Spectrum (Electron Ionization)splash10-0f79-7900000000-4ac54ba9a72c8707055dView in MoNA 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    13C NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Feces
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified0.65 +/- 0.19 uMAdlit (>18 years old)MaleNormal

  • 7668368

    • details BloodDetected and Quantified1.0 +/- 0.31 uMAdlit (>18 years old)FemaleNormal

  • 7668368

    • details FecesDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 20809621

    • details FecesDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 20809621

    • details FecesDetected but not Quantified Not SpecifiedNot Specified

    Normal

  • 20669995

    • details FecesDetected but not Quantified Adlit (>18 years old)FemaleNormal

  • 26709303

    • details UrineDetected and Quantified1.35 +/- 0.79 umol/mmol creatinineAdlit (>18 years old)BothNormal

  • 9212290

    • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified0.31 +/- 0.19 uMAdlit (>18 years old)BothIdiopathic oro-facial pain

  • 9212290

    • details UrineDetected and Quantified1.48 +/- 0.69 umol/mmol creatinineAdlit (>18 years old)BothIdiopathic oro-facial pain

  • 9212290

    • details

    Associated Disorders and Diseases Disease References

    Idiopathic oro-facial pain

    1. Aghabeigi B, Haque M, Wasil M, Hodges SJ, Henderson B, Harris M: The role of oxygen free radicals in idiopathic facial pain. Br J Oral Maxillofac Surg. 1997 Jun;35(3):161-5. [PubMed:9212290 ]

    Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    416 Phenol Explorer Metabolite ID

    416 FoodDB ID

    FDB000844 KNApSAcK ID

    C00002648 Chemspider ID

    3350 KEGG Compound ID

    C00628 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Gentisic acid NuGOwiki Link

    HMDB00152 Metagene Link

    HMDB00152 METLIN ID

    618 PubChem Compound

    3469 PDB ID

    GTQ ChEBI ID

    17189

    Product: Vps34-PIK-III

    References Synthesis Reference Morris, Steward G. Preparation of gentisic acid and its fatty alcohol esters.Journal of the American Chemical Society (1949), 71 2056-7 Material Safety Data Sheet (MSDS) Download (PDF) General References
    1. Ohsako M, Matsumoto Y, Goto S: Transport of aspirin and its metabolites through human erythrocyte membrane. Biol Pharm Bull. 1993 Feb;16(2):154-7. [PubMed:8364451 ]
    2. Almaas R, Rootwelt T, Oyasaeter S, Saugstad OD: Ascorbic acid enhances hydroxyl radical formation in iron-fortified infant cereals and infant formulas. Eur J Pediatr. 1997 Jun;156(6):488-92. [PubMed:9208249 ]
    3. Verhaeghe BJ, Lefevere MF, De Leenheer AP: Solid-phase extraction with strong anion-exchange columns for selective isolation and concentration of urinary organic acids. Clin Chem. 1988 Jun;34(6):1077-83. [PubMed:3378323 ]
    4. Palumbo G, Carlucci G, Mazzeo P, Frieri G, Pimpo MT, Fanini D: Simultaneous determination of 5-aminosalicylic acid, acetyl-5-aminosalicylic acid and 2,5-dihydroxybenzoic acid in endoscopic intestinal biopsy samples in humans by high-performance liquid chromatography with electrochemical detection. J Pharm Biomed Anal. 1995 Dec;14(1-2):175-80. [PubMed:8833980 ]
    5. Grootveld M, Halliwell B: Aromatic hydroxylation as a potential measure of hydroxyl-radical formation in vivo. Identification of hydroxylated derivatives of salicylate in human body fluids. Biochem J. 1986 Jul 15;237(2):499-504. [PubMed:3026319 ]
    6. Peleg H, Noble AC: Perceptual properties of benzoic acid derivatives. Chem Senses. 1995 Aug;20(4):393-400. [PubMed:8590024 ]
    7. Buskin JN, Upton RA, Williams RL: Improved liquid-chromatography of aspirin, salicylate, and salicyluric acid in plasma, with a modification for determining aspirin metabolites in urine. Clin Chem. 1982 May;28(5):1200-3. [PubMed:7074905 ]
    8. Liu JH, Smith PC: Direct analysis of salicylic acid, salicyl acyl glucuronide, salicyluric acid and gentisic acid in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Jan 12;675(1):61-70. [PubMed:8634769 ]
    9. Coudray C, Talla M, Martin S, Fatome M, Favier A: High-performance liquid chromatography-electrochemical determination of salicylate hydroxylation products as an in vivo marker of oxidative stress. Anal Biochem. 1995 May 1;227(1):101-11. [PubMed:7668368 ]
    10. Bochner F, Graham GG, Cham BE, Imhoff DM, Haavisto TM: Salicylate metabolite kinetics after several salicylates. Clin Pharmacol Ther. 1981 Aug;30(2):266-75. [PubMed:7249509 ]
    11. Cham BE, Bochner F, Imhoff DM, Johns D, Rowland M: Simultaneous liquid-chromatographic quantitation of salicylic acid, salicyluric acid, and gentisic acid in urine. Clin Chem. 1980 Jan;26(1):111-4. [PubMed:7356541 ]

    Enzymes

    General function:
    Involved in oxidoreductase activity
    Specific function:
    Not Available
    Gene Name:
    AOX1
    Uniprot ID:
    Q06278
    Molecular weight:
    147916.735
    Reactions
    Gentisic acid + Hydrogen peroxide → Gentisate aldehyde + Oxygen + Water details

    PMID: 6290821

    By rofalproject

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