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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:52 UTC
Update Date2017-10-23 19:04:19 UTC
HMDB IDHMDB0006116
Secondary Accession Numbers
  • HMDB06116
Metabolite Identification
Common Name3-Hydroxyhippuric acid
Description3-Hydroxyhippuric acid is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine. 3-Hydroxyhippuric acid is an organic acid found in normal human urine. 3-Hydroxyhippuric acid is a metabolite of rutin detected in urine after consumption of tomato juice (a source of rutin). 3-Hydroxyhippuric acid has its origin in dietary procyanidins (a major source of polyphenols consisting of elementary flavan-3-ol (epi)catechin units). 3-Hydroxyhippuric acid is a microbial aromatic acid metabolite derived from dietary polyphenols, found in normal human urine. (PMID: 12592675 , 2338430 , 17015248 , 14556848 , 12742116 ).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC9H9NO4
Average Molecular Weight195.1721
Monoisotopic Molecular Weight195.053157781
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number1637-75-8
SMILESNot Available
InChI Identifier
InChI=1S/C9H9NO4/c11-7-3-1-2-6(4-7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)
InChI KeyXDOFWFNMYJRHEW-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point164 - 169 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.95HANSCH,C ET AL. (1995)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1900000000-49e4d27497eeeff45809View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-7982000000-7959bea2ab616ece8756View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-899450f53ef2c1cb3e4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-4900000000-0ce4cb09039d70fe8e8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9300000000-264f280344785775dc13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-caff5245d469f41c4da8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-8a379c794edd9eeb0a03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9300000000-74897c8ed9e9ff09d06bView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 927 details
    BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 927 details
    BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 927 details
    BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 927 details
    BloodDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)BothNot Available details
    UrineDetected and Quantified15.06 +/- 10.91 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified0.51-51.27 umol/mmol creatinineAdult (>18 years old)BothNormal
      • David F. Putnam C...
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 927 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 927 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 927 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 927 details
    UrineDetected and Quantified5.7 ± 4.7 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
    UrineDetected and Quantified1.28 (0.1 - 6.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified2.5 (0.2 -5.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    UrineDetected and Quantified6.1(4.1-7.8) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified7.4(5.7-9.1) umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified19.604 +/- 13.104 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified17.247 +/- 12.596 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Gastroesophageal reflux disease
      • Mordechai, Hien, ...
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Hypertension (mild)
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Hypertension (mild)
    details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite ID927
    FoodDB IDFDB023830
    KNApSAcK IDNot Available
    Chemspider ID396603
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound450268
    PDB ID3XH
    ChEBI ID594277
    References
    Synthesis ReferenceVan Brussel, W.; Van Sumere, C. F. N-Acylamino acids and peptides. VI. A simple synthesis of N-acylglycines of the benzoyl and cinnamyl type. Bulletin des Societes Chimiques Belges (1978), 87(10), 791-7.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Liebich HM, Forst C: Basic profiles of organic acids in urine. J Chromatogr. 1990 Jan 26;525(1):1-14. [PubMed:2338430 ]
    2. Rechner AR, Kuhnle G, Hu H, Roedig-Penman A, van den Braak MH, Moore KP, Rice-Evans CA: The metabolism of dietary polyphenols and the relevance to circulating levels of conjugated metabolites. Free Radic Res. 2002 Nov;36(11):1229-41. [PubMed:12592675 ]
    3. Jaganath IB, Mullen W, Edwards CA, Crozier A: The relative contribution of the small and large intestine to the absorption and metabolism of rutin in man. Free Radic Res. 2006 Oct;40(10):1035-46. [PubMed:17015248 ]
    4. Gonthier MP, Donovan JL, Texier O, Felgines C, Remesy C, Scalbert A: Metabolism of dietary procyanidins in rats. Free Radic Biol Med. 2003 Oct 15;35(8):837-44. [PubMed:14556848 ]
    5. Gonthier MP, Rios LY, Verny M, Remesy C, Scalbert A: Novel liquid chromatography-electrospray ionization mass spectrometry method for the quantification in human urine of microbial aromatic acid metabolites derived from dietary polyphenols. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jun 15;789(2):247-55. [PubMed:12742116 ]

    Enzymes

    General function:
    Involved in glycine N-acyltransferase activity
    Specific function:
    Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
    Gene Name:
    GLYAT
    Uniprot ID:
    Q6IB77
    Molecular weight:
    18506.33
    Reactions
    3-Hydroxybenzoic acid → 3-Hydroxyhippuric aciddetails
    General function:
    Involved in glycine N-acyltransferase activity
    Specific function:
    Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
    Gene Name:
    GLYATL1
    Uniprot ID:
    Q969I3
    Molecular weight:
    35100.895
    General function:
    Involved in glycine N-acyltransferase activity
    Specific function:
    Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
    Gene Name:
    GLYATL2
    Uniprot ID:
    Q8WU03
    Molecular weight:
    34277.055
    General function:
    Involved in glycine N-acyltransferase activity
    Specific function:
    Acyltransferase which transfers the acyl group to the N- terminus of glycine
    Gene Name:
    GLYATL3
    Uniprot ID:
    Q5SZD4
    Molecular weight:
    32703.3