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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:33 UTC
Update Date2023-02-21 17:16:05 UTC
HMDB IDHMDB0002042
Secondary Accession Numbers
  • HMDB02042
Metabolite Identification
Common Name3-Phenylpropionylglycine
Description3-Phenylpropionylglycine 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-acylglycineUrinary excretion of 3-phenylpropionylglycine is a diagnostic marker for medium-chain acyl-CoA dehydrogenase deficiency. 3-phenylpropionylglycine is derived from 3-phenylpropionic acid, a product of anaerobic bacterial metabolism in the gut. (PMID 1541011 ).
Structure
Data?1676999765
Synonyms
ValueSource
2-[(3-oxo-3-Phenylpropyl)amino]acetateHMDB
Chemical FormulaC11H13NO3
Average Molecular Weight207.2258
Monoisotopic Molecular Weight207.089543287
IUPAC Name2-[(3-oxo-3-phenylpropyl)amino]acetic acid
Traditional Name3-phenylpropionylglycine
CAS Registry Number20989-69-9
SMILES
OC(=O)CNCCC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C11H13NO3/c13-10(6-7-12-8-11(14)15)9-4-2-1-3-5-9/h1-5,12H,6-8H2,(H,14,15)
InChI KeyXHSURMJJKAFELI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Benzoyl
  • Aryl alkyl ketone
  • Monocyclic benzene moiety
  • Benzenoid
  • Beta-aminoketone
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Secondary amine
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxide
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 Solubility0.52 g/LALOGPS
logP-1.3ALOGPS
logP-1.7ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)1.55ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity55.38 m³·mol⁻¹ChemAxon
Polarizability21.63 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+147.12631661259
DarkChem[M-H]-143.55831661259
DeepCCS[M+H]+144.52930932474
DeepCCS[M-H]-142.13330932474
DeepCCS[M-2H]-177.17530932474
DeepCCS[M+Na]+151.67530932474
AllCCS[M+H]+145.332859911
AllCCS[M+H-H2O]+141.332859911
AllCCS[M+NH4]+148.932859911
AllCCS[M+Na]+150.032859911
AllCCS[M-H]-148.132859911
AllCCS[M+Na-2H]-148.632859911
AllCCS[M+HCOO]-149.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-PhenylpropionylglycineOC(=O)CNCCC(=O)C1=CC=CC=C12968.8Standard polar33892256
3-PhenylpropionylglycineOC(=O)CNCCC(=O)C1=CC=CC=C11603.7Standard non polar33892256
3-PhenylpropionylglycineOC(=O)CNCCC(=O)C1=CC=CC=C11972.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Phenylpropionylglycine,1TMS,isomer #1C[Si](C)(C)OC(=O)CNCCC(=O)C1=CC=CC=C11980.2Semi standard non polar33892256
3-Phenylpropionylglycine,1TMS,isomer #2C[Si](C)(C)N(CCC(=O)C1=CC=CC=C1)CC(=O)O2038.6Semi standard non polar33892256
3-Phenylpropionylglycine,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(CCC(=O)C1=CC=CC=C1)[Si](C)(C)C2028.0Semi standard non polar33892256
3-Phenylpropionylglycine,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(CCC(=O)C1=CC=CC=C1)[Si](C)(C)C2064.1Standard non polar33892256
3-Phenylpropionylglycine,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(CCC(=O)C1=CC=CC=C1)[Si](C)(C)C2390.6Standard polar33892256
3-Phenylpropionylglycine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNCCC(=O)C1=CC=CC=C12220.7Semi standard non polar33892256
3-Phenylpropionylglycine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCC(=O)C1=CC=CC=C1)CC(=O)O2284.0Semi standard non polar33892256
3-Phenylpropionylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(CCC(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2538.9Semi standard non polar33892256
3-Phenylpropionylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(CCC(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2509.1Standard non polar33892256
3-Phenylpropionylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(CCC(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2609.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Phenylpropionylglycine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-1304cc30fc89579372e52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Phenylpropionylglycine GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-6920000000-e02a1f77435b7d9a5e602017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Phenylpropionylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylpropionylglycine 10V, Positive-QTOFsplash10-0bt9-0950000000-d2c03fd3aafa149855362017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylpropionylglycine 20V, Positive-QTOFsplash10-0bu0-2900000000-4cce4e73d5ba872725e22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylpropionylglycine 40V, Positive-QTOFsplash10-0a4i-9500000000-124697a522d2d530772e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylpropionylglycine 10V, Negative-QTOFsplash10-0a4i-0290000000-0a7de399ee46744c1e572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylpropionylglycine 20V, Negative-QTOFsplash10-0ab9-9780000000-1e1b52f843008771cdc62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylpropionylglycine 40V, Negative-QTOFsplash10-05fr-9100000000-7c69f9ac256c40d756bc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylpropionylglycine 10V, Positive-QTOFsplash10-053r-2920000000-5dcd0d3d4cb1e45be37a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylpropionylglycine 20V, Positive-QTOFsplash10-053r-5900000000-f447bc2ad22dea0a99012021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylpropionylglycine 40V, Positive-QTOFsplash10-004i-9500000000-5be781928cdaa97b4e582021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylpropionylglycine 10V, Negative-QTOFsplash10-0a4i-0190000000-854712f80fb03b7ddc6d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylpropionylglycine 20V, Negative-QTOFsplash10-014r-5910000000-357fec7c0b8fe74cf3de2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylpropionylglycine 40V, Negative-QTOFsplash10-004l-9200000000-23948b066aab57341f6b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022813
KNApSAcK IDNot Available
Chemspider ID1296138
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6455
PubChem Compound1608346
PDB IDNot Available
ChEBI IDNot Available
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. Rinaldo P, O'Shea JJ, Welch RD, Tanaka K: Stable isotope dilution analysis of n-hexanoylglycine, 3-phenylpropionylglycine and suberylglycine in human urine using chemical ionization gas chromatography/mass spectrometry selected ion monitoring. Biomed Environ Mass Spectrom. 1989 Jul;18(7):471-7. [PubMed:2775902 ]
  2. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628 ]
  3. Rinaldo P, O'Shea JJ, Welch RD, Tanaka K: The enzymatic basis for the dehydrogenation of 3-phenylpropionic acid: in vitro reaction of 3-phenylpropionyl-CoA with various acyl-CoA dehydrogenases. Pediatr Res. 1990 May;27(5):501-7. [PubMed:2345678 ]
  4. Bennett MJ, Bhala A, Poirier SF, Ragni MC, Willi SM, Hale DE: When do gut flora in the newborn produce 3-phenylpropionic acid? Implications for early diagnosis of medium-chain acyl-CoA dehydrogenase deficiency. Clin Chem. 1992 Feb;38(2):278-81. [PubMed:1541011 ]

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