Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-11-09 23:14:25 UTC
HMDB IDHMDB0000735
Secondary Accession Numbers
  • HMDB00735
Metabolite Identification
Common NameHydroxyphenylacetylglycine
DescriptionHydroxyphenylacetylglycine 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. Hydroxyphenylacetylglycine is an endogenous human metabolite. It can be originated from the metabolism of tyramine, itself is a monoamine compound derived from the amino acid tyrosine. Hydroxyphenylacetylglycine can also be derived from the metabolism of 3,4-dihydroxyphenylalanine (L-DOPA). In the metabolism of tyrosine, this compound is involved in the reaction Hydroxyphenylacetyl-CoA + Glycine <=> Hydroxyphenylacetylglycine + CoA, catalyzed by acyltransferase enzymes (EC 2.3.1.-). Hydroxyphenylacetylglycine has been identified in human biofluids. (PMID: 14201174 , 912020 , 716472 , 7096501 , 7438429 , 7438430 ).
Structure
Data?1582752153
Synonyms
ValueSource
p-HydroxyphenylacetylglycineChEBI
4-HydroxyphenylacetylglycineKegg
N-[(4-Hydroxyphenyl)acetyl]-glycineHMDB
N-[(p-Hydroxyphenyl)acetyl]-glycineHMDB
[[(4-Hydroxyphenyl)acetyl]amino]acetateHMDB
[[(4-Hydroxyphenyl)acetyl]amino]acetic acidHMDB
Chemical FormulaC10H11NO4
Average Molecular Weight209.1986
Monoisotopic Molecular Weight209.068807845
IUPAC Name2-[2-(4-hydroxyphenyl)acetamido]acetic acid
Traditional Namep-hydroxyphenylacetylglycine
CAS Registry Number28116-23-6
SMILES
OC(=O)CNC(=O)CC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C10H11NO4/c12-8-3-1-7(2-4-8)5-9(13)11-6-10(14)15/h1-4,12H,5-6H2,(H,11,13)(H,14,15)
InChI KeyCPPDWYIPKSSNNM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Phenylacetamide
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2 g/LALOGPS
logP10(0.46) g/LALOGPS
logP10(0.2) g/LChemAxon
logS10(-2) g/LALOGPS
pKa (Strongest Acidic)3.54ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity52.15 m³·mol⁻¹ChemAxon
Polarizability20.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+148.43731661259
DarkChem[M-H]-143.64931661259
AllCCS[M+H]+145.12432859911
AllCCS[M-H]-146.38532859911
DeepCCS[M+H]+143.2330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HydroxyphenylacetylglycineOC(=O)CNC(=O)CC1=CC=C(O)C=C13576.5Standard polar33892256
HydroxyphenylacetylglycineOC(=O)CNC(=O)CC1=CC=C(O)C=C11922.9Standard non polar33892256
HydroxyphenylacetylglycineOC(=O)CNC(=O)CC1=CC=C(O)C=C12246.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hydroxyphenylacetylglycine,1TMS,isomer #1C[Si](C)(C)OC(=O)CNC(=O)CC1=CC=C(O)C=C12194.0Semi standard non polar33892256
Hydroxyphenylacetylglycine,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(CC(=O)NCC(=O)O)C=C12175.4Semi standard non polar33892256
Hydroxyphenylacetylglycine,1TMS,isomer #3C[Si](C)(C)N(CC(=O)O)C(=O)CC1=CC=C(O)C=C12178.4Semi standard non polar33892256
Hydroxyphenylacetylglycine,2TMS,isomer #1C[Si](C)(C)OC(=O)CNC(=O)CC1=CC=C(O[Si](C)(C)C)C=C12220.9Semi standard non polar33892256
Hydroxyphenylacetylglycine,2TMS,isomer #2C[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O)C=C1)[Si](C)(C)C2188.4Semi standard non polar33892256
Hydroxyphenylacetylglycine,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(CC(=O)N(CC(=O)O)[Si](C)(C)C)C=C12177.4Semi standard non polar33892256
Hydroxyphenylacetylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C2174.0Semi standard non polar33892256
Hydroxyphenylacetylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C2163.0Standard non polar33892256
Hydroxyphenylacetylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C2333.1Standard polar33892256
Hydroxyphenylacetylglycine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CC1=CC=C(O)C=C12435.1Semi standard non polar33892256
Hydroxyphenylacetylglycine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CC(=O)NCC(=O)O)C=C12440.3Semi standard non polar33892256
Hydroxyphenylacetylglycine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)CC1=CC=C(O)C=C12426.1Semi standard non polar33892256
Hydroxyphenylacetylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12732.4Semi standard non polar33892256
Hydroxyphenylacetylglycine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C2674.2Semi standard non polar33892256
Hydroxyphenylacetylglycine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(CC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)C=C12716.5Semi standard non polar33892256
Hydroxyphenylacetylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2892.1Semi standard non polar33892256
Hydroxyphenylacetylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2793.4Standard non polar33892256
Hydroxyphenylacetylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2669.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-2900000000-1415e9dae0fe852be5b22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (2 TMS) - 70eV, Positivesplash10-052r-4960000000-c259468bc9a07e18a1062017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenylacetylglycine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-056r-9610000000-cad7edd3bdf64818adae2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenylacetylglycine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-1900000000-fcf6e7a07522876233242012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenylacetylglycine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a6r-7900000000-7353e482e3f45a50129a2012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 10V, Positive-QTOFsplash10-03di-4970000000-eb650d805c8ca10605b92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 20V, Positive-QTOFsplash10-0a6r-9800000000-4e655164c76ffc2f0f8d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 40V, Positive-QTOFsplash10-056r-9400000000-f80f879428cd5b8e5a542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 10V, Negative-QTOFsplash10-0a4i-0490000000-adf532f32e7ca51dac4a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 20V, Negative-QTOFsplash10-0a4i-5950000000-715ae07076da0da3ca9b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 40V, Negative-QTOFsplash10-0ab9-9300000000-a87e01aa42a8a324261c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 10V, Negative-QTOFsplash10-0a4i-2290000000-8d71de795ba88cb985c12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 20V, Negative-QTOFsplash10-0a4i-2900000000-d1aba2e1917f49fbb5df2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 40V, Negative-QTOFsplash10-0a4l-9700000000-ceab54edfc0fa99b51612021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 10V, Positive-QTOFsplash10-052r-1910000000-1bd1fc053034b378cb722021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 20V, Positive-QTOFsplash10-0a4i-9700000000-85acdf94596569b8e7c42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 40V, Positive-QTOFsplash10-0a6r-9700000000-31e7a20a6025dcbd29d72021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
UrineDetected and Quantified<0.0025–0.0079 umol/mmol creatinineAdult (25-30 years old)Both
Not Available
details
UrineDetected and Quantified<0.0025–0.0097 umol/mmol creatinineAdult (25-30 years old)Both
Not Available
details
UrineDetected and Quantified<0.0025–0.0048 umol/mmol creatinineAdult (25-30 years old)Both
Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022212
KNApSAcK IDNot Available
Chemspider ID389604
KEGG Compound IDC05596
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440732
PDB IDNot Available
ChEBI ID28595
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ramsdell HS, Baretz BH, Tanaka K: Mass spectrometric studies of twenty-one metabolically important acylglycines. Biomed Mass Spectrom. 1977 Aug;4(4):220-5. [PubMed:912020 ]
  2. Tanaka K, Hine DG: Compilation of gas chromatographic retention indices of 163 metabolically important organic acids, and their use in detection of patients with organic acidurias. J Chromatogr. 1982 Apr 30;239:301-22. [PubMed:7096501 ]
  3. Tanaka K, West-Dull A, Hine DG, Lynn TB, Lowe T: Gas-chromatographic method of analysis for urinary organic acids. II. Description of the procedure, and its application to diagnosis of patients with organic acidurias. Clin Chem. 1980 Dec;26(13):1847-53. [PubMed:7438430 ]
  4. NAKAJIMA T, SANO I: NEW METABOLITES OF P-TYRAMINE FROM THE URINE OF RATS. Biochim Biophys Acta. 1964 Jul 15;90:37-44. [PubMed:14201174 ]
  5. Goodwin BL, Ruthven CR, King GS, Sandler M: Metabolism of 3, 4-dihydroxyphenylalanine, its metabolites and analogues in vivo in the rat: urinary excretion pattern. Xenobiotica. 1978 Oct;8(10):629-51. [PubMed:716472 ]
  6. Tanaka K, Hine DG, West-Dull A, Lynn TB: Gas-chromatographic method of analysis for urinary organic acids. I. Retention indices of 155 metabolically important compounds. Clin Chem. 1980 Dec;26(13):1839-46. [PubMed:7438429 ]

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
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
General function:
Involved in damaged DNA binding
Specific function:
Acetyltransferase required for the establishment of sister chromatid cohesion and couple the processes of cohesion and DNA replication to ensure that only sister chromatids become paired together. In contrast to the structural cohesins, the deposition and establishment factors are required only during S phase. Acts by mediating the acetylation of cohesin component SMC3
Gene Name:
ESCO1
Uniprot ID:
Q5FWF5
Molecular weight:
94982.2