GABAReceptorInhibitorgabareceptorinhibitor

Homogentisic acid

By rofalproject
Common Name

Homogentisic acid Description

Homogentisic acid is an intermediate of the metabolic breakdown of tyrosine and phenylalanine; it occurs in the urine in cases of alkaptonuria. (OMIN 203500) Homogentisic acid is the primary precursor of melanin synthesis in Vibrio cholerae. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 2,5-Dihydroxyphenylacetic acidChEBI 2-(3,6-DIHYDROXYPHENYL)acetIC ACIDChEBI 2,5-DihydroxyphenylacetateGenerator HomogentisateGenerator 2-(3,6-DIHYDROXYPHENYL)acetateGenerator (2,5-Dihydroxyphenyl)-acetateHMDB (2,5-Dihydroxyphenyl)-acetic acidHMDB 2,5-Dihydroxy-a-toluateHMDB 2,5-Dihydroxy-a-toluic acidHMDB 2,5-Dihydroxy-alpha-toluateHMDB 2,5-Dihydroxy-alpha-toluic acidHMDB 2,5-Dihydroxy-benzeneacetateHMDB 2,5-Dihydroxy-benzeneacetic acidHMDB AlcaptonHMDB Homogentisate acidHMDB HomogentisinateHMDB Homogentisinic acidHMDB Melanic acidHMDB Acid, homogentisicMeSH

Chemical Formlia

C8H8O4 Average Molecliar Weight

168.1467 Monoisotopic Molecliar Weight

168.042258744 IUPAC Name

2-(2,5-dihydroxyphenyl)acetic acid Traditional Name

homogentisic acid CAS Registry Number

451-13-8 SMILES

OC(=O)CC1=C(O)C=CC(O)=C1

InChI Identifier

InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)

InChI Key

IGMNYECMUMZDDF-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

2(hydroxyphenyl)acetic acids Alternative Parents

  • Hydroquinones
  • 1-hydroxy-2-unsubstituted benzenoids
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • 2(hydroxyphenyl)acetic acid
  • Hydroquinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • hydroquinones (CHEBI:44747 )
  • dihydroxyphenylacetic acid (CHEBI:44747 )

    • Ontology Status

    Detected and Quantified Origin

  • Endogenous

    • Biofunction

  • Component of Phenylalanine metabolism
  • Component of Tyrosine metabolism

    • Application

    Not Available Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point153 °CNot Available Boiling PointNot AvailableNot Available Water Solubility850 mg/mL at 25 °CNot Available LogP0.86SANGSTER (1994)

    Predicted Properties

    Property Value Source Water Solubility8.1 mg/mLALOGPS logP0.81ALOGPS logP1ChemAxon logS-1.3ALOGPS pKa (Strongest Acidic)3.57ChemAxon pKa (Strongest Basic)-5.9ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area77.76 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity41.33 m3·mol-1ChemAxon Polarizability15.57 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)splash10-000t-0945000000-2f4b9ef9c9ee6e7cd1edView in MoNA GC-MS

    GC-MS Spectrum – GC-MS (3 TMS)splash10-0016-3955000000-1cdc64ab3032ff29df29View in MoNA GC-MS

    GC-MS Spectrum – EI-Bsplash10-0a5c-0679000000-97890865f85a79efa2e6View in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOFsplash10-0002-0944000000-fd48cc27da661ce24833View in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOFsplash10-0002-0944000000-fd48cc27da661ce24833View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-9c395aa569b4b54f8681View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-00xs-9500000000-ab92286f0d5bc843814bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-35740a40f4fdf3e84c3cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-f4eba60d63bd99e18b8bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-12e330dc18f0b128b961View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-0900000000-4bd53b0472edd31e8609View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-0900000000-7121173193a9ba3751a4View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00di-1900000000-04eca21bf25c671b8b6eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00di-0900000000-780d3740762c2ff89d9aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-00di-0900000000-9c85164306514c6d4c4bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-TOF , negativesplash10-00di-0900000000-867a4e32ba2d14fd0aadView in MoNA 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    13C NMR SpectrumNot Available 2D NMR

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

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

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Feces
  • Urine

    • Tissue Location

  • Cartilage
  • Connective Tissue
  • Kidney

    • Pathways

    Name SMPDB Link KEGG Link AlkaptonuriaSMP00169Not Available Dislifiram PathwaySMP00429Not Available Dopamine beta-hydroxylase deficiencySMP00498Not Available HawkinsinuriaSMP00190Not Available Monoamine oxidase-a deficiency (MAO-A)SMP00533Not Available Phenylalanine and Tyrosine MetabolismSMP00008map00360 PhenylketonuriaSMP00206Not Available Tyrosine MetabolismSMP00006map00350 Tyrosinemia Type 2 (or Richner-Hanhart syndrome)SMP00369Not Available Tyrosinemia Type 3 (TYRO3)SMP00370Not Available Tyrosinemia Type ISMP00218Not Available Tyrosinemia, transient, of the newbornSMP00494Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified0.043 (0.014 – 0.071) uMAdlit (>18 years old)BothNormal

  • 8925087

    • details FecesDetected but not Quantified Not SpecifiedNot Specified

    Normal

  • 19573517

    • details FecesDetected but not Quantified Not SpecifiedNot Specified

    Normal

  • 19573517

    • details FecesDetected but not Quantified Not SpecifiedNot Specified

    Normal

  • 20669995

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

  • 26709303

    • details UrineDetected and Quantified0.04 +/- 0.17 umol/mmol creatinineInfant (0-1 year old)BothNormal

  • 2026685

    • details UrineDetected and Quantified1.70 (0.5 – 2.8) umol/mmol creatinineAdlit (>18 years old)Both

    Normal

  • 24023812

    • details UrineDetected and Quantified0.0 umol/mmol creatinineChildren (1 – 18 years old)Both

    Normal

  • BC Children's Hos…

    • details UrineDetected and Quantified1.917 +/- 1.061 umol/mmol creatinineChildren (1 – 13 years old)Not Specified

    Normal

  • Mordechai, Hien, …

    • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified35.5 (33.0 – 38.0) uMAdlit (>18 years old)BothAlkaptonuria

  • 2383921

    • details UrineDetected and Quantified1.0 (0.0-2.0) umol/mmol creatinineAdlit (>18 years old)BothAlkaptonuria

  • MetaGene

    • details UrineDetected and Quantified3000.0 (1000.0-5000.0) umol/mmol creatinineChildren (1-13 years old)BothHomogentisic Acid Oxidase deficiency (Alkaptonuria)

  • MetaGene

    • details UrineDetected and Quantified1819 (1134 – 2504) umol/mmol creatinineAdlit (>18 years old)BothAlkaptonuria

  • 12501223

    • details UrineDetected and Quantified> 2780 umol/mmol creatinineAdlit (>18 years old)BothAlkaptonuria

  • 9529368

    • details UrineDetected and Quantified3.009 +/- 1.469 umol/mmol creatinineChildren (1 – 13 years old)Not Specified

    Eosinophilic esophagitis

  • Mordechai, Hien, …

    • details

    Associated Disorders and Diseases Disease References

    Alkaptonuria

    1. Phornphutkli C, Introne WJ, Perry MB, Bernardini I, Murphey MD, Fitzpatrick DL, Anderson PD, Huizing M, Anikster Y, Gerber LH, Gahl WA: Natural history of alkaptonuria. N Engl J Med. 2002 Dec 26;347(26):2111-21. [PubMed:12501223 ]
    2. La Du BN Jr: Are we ready to try to cure alkaptonuria? Am J Hum Genet. 1998 Apr;62(4):765-7. [PubMed:9529368 ]
    3. Bory C, Boliieu R, Chantin C, Mathieu M: Diagnosis of alcaptonuria: rapid analysis of homogentisic acid by HPLC. Clin Chim Acta. 1990 Jli;189(1):7-11. [PubMed:2383921 ]
    4. MetaGene [Link]

    Associated OMIM IDs

  • 203500 (Alkaptonuria)

    • External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB021899 KNApSAcK ID

    Not Available Chemspider ID

    759 KEGG Compound ID

    C00544 BioCyc ID

    Not Available BiGG ID

    1485308 Wikipedia Link

    Homogentisic acid NuGOwiki Link

    HMDB00130 Metagene Link

    HMDB00130 METLIN ID

    331 PubChem Compound

    780 PDB ID

    OMD ChEBI ID

    44747

    Product: GAL-021

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Download (PDF) General References
    1. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
    2. Phornphutkul C, Introne WJ, Perry MB, Bernardini I, Murphey MD, Fitzpatrick DL, Anderson PD, Huizing M, Anikster Y, Gerber LH, Gahl WA: Natural history of alkaptonuria. N Engl J Med. 2002 Dec 26;347(26):2111-21. [PubMed:12501223 ]
    3. La Du BN Jr: Are we ready to try to cure alkaptonuria? Am J Hum Genet. 1998 Apr;62(4):765-7. [PubMed:9529368 ]
    4. Concepcion Masip T, Banares Baudet F, Traba ML, Rodriguez de Minon Cifuentes JL: [Alkaptonuria, prostatic calculi, and ectopic ureter]. Actas Urol Esp. 1997 Feb;21(2):167-70. [PubMed:9214216 ]
    5. Ehongo A, Schrooyen M, Pereleux A: [Important bilateral corneal astigmatism in a case of ocular ochronosis]. Bull Soc Belge Ophtalmol. 2005;(295):17-21. [PubMed:15849984 ]
    6. Deutsch JC, Santhosh-Kumar CR: Quantitation of homogentisic acid in normal human plasma. J Chromatogr B Biomed Appl. 1996 Feb 23;677(1):147-51. [PubMed:8925087 ]
    7. Janocha S, Wolz W, Srsen S, Srsnova K, Montagutelli X, Guenet JL, Grimm T, Kress W, Muller CR: The human gene for alkaptonuria (AKU) maps to chromosome 3q. Genomics. 1994 Jan 1;19(1):5-8. [PubMed:8188241 ]
    8. de Haas V, Carbasius Weber EC, de Klerk JB, Bakker HD, Smit GP, Huijbers WA, Duran M, Poll-The BT: The success of dietary protein restriction in alkaptonuria patients is age-dependent. J Inherit Metab Dis. 1998 Dec;21(8):791-8. [PubMed:9870204 ]
    9. Hegedus ZL, Nayak U: Homogentisic acid and structurally related compounds as intermediates in plasma soluble melanin formation and in tissue toxicities. Arch Int Physiol Biochim Biophys. 1994 May-Jun;102(3):175-81. [PubMed:8000039 ]
    10. Venkataseshan VS, Chandra B, Graziano V, Steinlauf P, Marquet E, Irmiere V, Needle MA: Alkaptonuria and renal failure: a case report and review of the literature. Mod Pathol. 1992 Jul;5(4):464-71. [PubMed:1495952 ]
    11. Bory C, Boulieu R, Chantin C, Mathieu M: Diagnosis of alcaptonuria: rapid analysis of homogentisic acid by HPLC. Clin Chim Acta. 1990 Jul;189(1):7-11. [PubMed:2383921 ]

    Enzymes

    General function:
    Involved in 4-hydroxyphenylpyruvate dioxygenase activity
    Specific function:
    Key enzyme in the degradation of tyrosine.
    Gene Name:
    HPD
    Uniprot ID:
    P32754
    Molecular weight:
    40497.105
    Reactions
    4-Hydroxyphenylpyruvic acid + Oxygen → Homogentisic acid + CO(2) details 4-Hydroxyphenylpyruvic acid + Oxygen → Homogentisic acid + Carbon dioxide details
    General function:
    Involved in homogentisate 1,2-dioxygenase activity
    Specific function:
    Not Available
    Gene Name:
    HGD
    Uniprot ID:
    Q93099
    Molecular weight:
    49963.41
    Reactions
    Homogentisic acid + Oxygen → Maleylacetoacetic acid details

    PMID: 12526815

    By rofalproject

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