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Showing Compound N-(2-Hydroxybenzoyl)glycine (FDB010505)

Record Information
Version1.0
Creation date2010-04-08 22:09:09 UTC
Update date2019-11-26 03:03:40 UTC
Primary IDFDB010505
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-(2-Hydroxybenzoyl)glycine
DescriptionConstituent of milk Salicyluric 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; The induction of the salicyluric acid formation is one of the saturable pathways of salicylate elimination.; The formation of the methyl ester of salicyluric acid is observed during the quantitation of salicyluric acid and other salicylate metabolites in urine by high-pressure liquid chromatography. This methyl ester formation causes artificially low values for salicyluric acid and high values for salicylic acid.; (PMID: 6101164, 6857178). N-(2-Hydroxybenzoyl)glycine is found in milk and milk products.
CAS Number487-54-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
N-(2-Hydroxybenzoyl)-glycineChEBI
N-SalicyloylglycineChEBI
O-Hydroxyhippuric acidChEBI
SalicyloylglycineChEBI
SalicylurateChEBI
O-HydroxyhippateGenerator
O-Hydroxyhippic acidGenerator
SalicylateGenerator
Salicylic acidGenerator
((2-Hydroxybenzoyl)amino)acetic acidHMDB
(2-Hydroxybenzoyl)glycineHMDB
2-HydroxybenzoylaminoacetateHMDB
2-Hydroxybenzoylaminoacetic acidHMDB
2-HydroxybenzoylglycineHMDB
2-HydroxyhippurateHMDB
2-Hydroxyhippuric acidHMDB
N-O-HydroxybenzoylglycineHMDB
O-Hydroxy-hippurateHMDB
O-Hydroxy-hippuric acidHMDB
O-HydroxyhippurateHMDB
Ortho-hydroxyhippurateHMDB
Ortho-hydroxyhippuric acidHMDB
SalicylglycineHMDB
[(2-Hydroxybenzoyl)amino]acetateHMDB
[(2-Hydroxybenzoyl)amino]acetic acidHMDB
Salicylurate, monosodium saltHMDB
N-(O-Hydroxybenzoyl)glycineHMDB
2-[(2-Hydroxybenzoyl)amino]acetic acidHMDB
2'-Hydroxyhippuric acidHMDB
((2-hydroxybenzoyl)amino)acetic acidbiospider
(2-hydroxybenzamido)acetic acidbiospider
2-Hydroxybenzamidoacetic aciddb_source
2-hydroxybenzoylaminoacetatebiospider
2-hydroxybenzoylaminoacetic acidbiospider
Glycine, N-(2-hydroxybenzoyl)-biospider
Glycine, N-(2-hydroxybenzoyl)- (9CI)biospider
Glycine, n-salicyloyl-biospider
Hippuric acid, o-hydroxy-biospider
N-o-hydroxybenzoylglycinebiospider
N-salicyloylglycinebiospider
O-hydroxy-hippuratebiospider
O-hydroxy-hippuric acidbiospider
O-hydroxyhippuratebiospider
O-hydroxyhippuric acidbiospider
o-Hydroxyhippuric acid, 8CIdb_source
Salicyloylaminoacetic aciddb_source
Salicyluric aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility4.04 g/LALOGPS
logP0.51ALOGPS
logP0.87ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.27ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.1 m³·mol⁻¹ChemAxon
Polarizability18.4 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H9NO4
IUPAC name2-[(2-hydroxyphenyl)formamido]acetic acid
InChI IdentifierInChI=1S/C9H9NO4/c11-7-4-2-1-3-6(7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)
InChI KeyONJSZLXSECQROL-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CNC(=O)C1=CC=CC=C1O
Average Molecular Weight195.1721
Monoisotopic Molecular Weight195.053157781
Classification
Description Belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHippuric acids
Alternative Parents
Substituents
  • Hippuric acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Salicylic acid or derivatives
  • Salicylamide
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 55.39%; H 4.65%; N 7.18%; O 32.79%DFC
    Melting PointMp 170-172°DFC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logP0.95HANSCH,C ET AL. (1995)
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    GC-MSN-(2-Hydroxybenzoyl)glycine, 3 TMS, GC-MS Spectrumsplash10-0006-1921000000-494271209c45ba6e054eSpectrum
    GC-MSN-(2-Hydroxybenzoyl)glycine, 2 TMS, GC-MS Spectrumsplash10-0a4l-3942000000-04aa13977839f7430e87Spectrum
    GC-MSN-(2-Hydroxybenzoyl)glycine, non-derivatized, GC-MS Spectrumsplash10-0006-1921000000-494271209c45ba6e054eSpectrum
    GC-MSN-(2-Hydroxybenzoyl)glycine, non-derivatized, GC-MS Spectrumsplash10-0a4l-3942000000-04aa13977839f7430e87Spectrum
    GC-MSN-(2-Hydroxybenzoyl)glycine, non-derivatized, GC-MS Spectrumsplash10-0006-0921000000-3ee04ebbc6ba044f6e25Spectrum
    GC-MSN-(2-Hydroxybenzoyl)glycine, non-derivatized, GC-MS Spectrumsplash10-0a4l-1942000000-14e4da43f05418868f3dSpectrum
    Predicted GC-MSN-(2-Hydroxybenzoyl)glycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-2900000000-558ece7e40b6a2505e9bSpectrum
    Predicted GC-MSN-(2-Hydroxybenzoyl)glycine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-7972000000-6d3342d12b15e7739ff0Spectrum
    Predicted GC-MSN-(2-Hydroxybenzoyl)glycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSN-(2-Hydroxybenzoyl)glycine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSN-(2-Hydroxybenzoyl)glycine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSN-(2-Hydroxybenzoyl)glycine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSN-(2-Hydroxybenzoyl)glycine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSN-(2-Hydroxybenzoyl)glycine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSN-(2-Hydroxybenzoyl)glycine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSN-(2-Hydroxybenzoyl)glycine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSN-(2-Hydroxybenzoyl)glycine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSN-(2-Hydroxybenzoyl)glycine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSN-(2-Hydroxybenzoyl)glycine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSN-(2-Hydroxybenzoyl)glycine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-5fc858fcdd858768270f2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-3900000000-05f9fa1a8cebedcf52c92012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01bc-9200000000-169ad1809ba2a4accf082012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-d6d7f1809f1779d278b32012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-2900000000-d099d157b6253af681d32012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9100000000-96900edd4f6aa1f2c3b92012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-511684503214f5c466682012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-8daa85624d5a460188582012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-d6d7f1809f1779d278b32017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-2900000000-d099d157b6253af681d32017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9100000000-96900edd4f6aa1f2c3b92017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-511684503214f5c466682017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-8daa85624d5a460188582017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-0900000000-7f8ca4379a27c9d6fad92017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-9b88237d9c8a1f5864a82021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-5f0973db56ba7f4637a52021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9100000000-8d96e93a2efb83a5b59b2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-9000000000-b7f5fb721797c78801422021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e41d3042048b1bf5a6372021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-2900000000-329e9ccbe80298c87ec22016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-5900000000-be142fe17e5fc055f83c2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fu-9200000000-1490fe4359681e391fd32016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-47cf95d67574e923d0002016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-3900000000-65d91bbe9e076cff41772016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9100000000-e75a3b91d96f8d45614e2016-09-12View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider ID9835
    ChEMBL IDCHEMBL586
    KEGG Compound IDC07588
    Pubchem Compound ID10253
    Pubchem Substance IDNot Available
    ChEBI ID9008
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB00840
    CRC / DFC (Dictionary of Food Compounds) IDFBR99-Y:FBR99-Y
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID928
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    Enzymes
    NameGene NameUniProt ID
    Glycine N-acyltransferaseGLYATQ6IB77
    Glycine N-acyltransferase-like protein 1GLYATL1Q969I3
    Glycine N-acyltransferase-like protein 2GLYATL2Q8WU03
    Glycine N-acyltransferase-like protein 3GLYATL3Q5SZD4
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference