Phenylpropionylglycine (CHEM021837)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:13:42 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021837
Identification
Common NamePhenylpropionylglycine
ClassSmall Molecule
DescriptionPhenylpropionylglycine 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 detection of phenylpropionylglycine in urine after an oral load of phenylpropionic acid can be used to diagnose deficiency of medium-chain acyl-CoA dehydrogenase, a frequent and treatable metabolic defect. (PMID 9234867) [HMDB]
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-[(1-Hydroxy-3-phenylpropylidene)amino]acetateHMDB
(3-Phenyl-propionylamino)-acetateHMDB
(3-Phenyl-propionylamino)-acetic acidHMDB
(3-Phenylpropionyl)glycineHMDB
N-(3-Phenyl-propionyl)-glycineHMDB
N-(3-Phenylpropanoyl)glycineHMDB
3-PhenylpropionylglycineHMDB
Chemical FormulaC11H13NO3
Average Molecular Mass207.226 g/mol
Monoisotopic Mass207.090 g/mol
CAS Registry Number56613-60-6
IUPAC Name2-(3-phenylpropanamido)acetic acid
Traditional Namephenylpropionylglycine
SMILESOC(=O)CNC(=O)CCC1=CC=CC=C1
InChI IdentifierInChI=1S/C11H13NO3/c13-10(12-8-11(14)15)7-6-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)(H,14,15)
InChI KeyYEIQSAXUPKPPBN-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
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP0.93ALOGPS
logP0.95ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity54.77 m³·mol⁻¹ChemAxon
Polarizability21.47 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-6900000000-49e6bd1ae55ef730be57Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03l3-7910000000-288e575c4d82667708e6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-056r-9510000000-857882337db8707be6daSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-3900000000-ac64df3f4f25d003198bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-056u-9400000000-ba5317e2dcb281f5ad7fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-5232244a5f1e32f44bfaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-9120000000-3ad79b9ff64c3f9402d4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-952c82e2b34ef96383e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-5980000000-e671cd58f497ac7faac9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9600000000-f46c69e1694bd406aed7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9300000000-614fceaf9ffefb201233Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-aa434ae4ae70d3eae4bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-6970000000-55314833bc2ceca004c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9200000000-26dcb24e7bc9b913dd22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1690000000-8b2f04f031ae7c4b49e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-8910000000-18d0ad5b9e5aa8c4284cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9100000000-9feb6c67f526b26df373Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-3920000000-f55c3c8e5ea50cbea724Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-8900000000-da57702d9fb756c9d7e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-9600000000-6de90f0cc8c6eaf079f4Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000860
FooDB IDFDB022286
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5823
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID134261
ChEBI ID266653
PubChem Compound ID152323
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Geurts, Muriel; Poupaert, Jacques H.; Scriba, Gerhard K. E.; Lambert, Didier M. N-(Benzyloxycarbonyl)glycine Esters and Amides as New Anticonvulsants. Journal of Medicinal Chemistry (1998), 41(1), 24-30.
2. Green A, Preece MA, de Sousa C, Pollitt RJ: Possible deleterious effect of L-carnitine supplementation in a patient with mild multiple acyl-CoA dehydrogenation deficiency (ethylmalonic-adipic aciduria). J Inherit Metab Dis. 1991;14(5):691-7.
3. Rocchiccioli F, Cartier PH, Bougneres PF: Mass spectrometric identification of abnormal aromatic compounds in the urine of a child with Reye's like syndrome. Biomed Mass Spectrom. 1984 Mar;11(3):127-31.
4. Flath B, Rolinski B, Roscher AA: Simple high-performance liquid chromatographic method for the detection of phenylpropionylglycine in urine as a diagnostic tool in inherited medium-chain acyl-coenzyme A dehydrogenase deficiency. J Chromatogr B Biomed Sci Appl. 1997 Jun 20;694(1):227-32.
5. Gregersen N, Winter V, Lyonnet S, Saudubray JM, Wendel U, Jensen TG, Andresen BS, Kolvraa S, Lehnert W, Bolund L, et al.: Molecular genetic characterization and urinary excretion pattern of metabolites in two families with MCAD deficiency due to compound heterozygosity with a 13 base pair insertion in one allele. J Inherit Metab Dis. 1994;17(2):169-84.
6. Rinaldo P, O'Shea JJ, Coates PM, Hale DE, Stanley CA, Tanaka K: Medium-chain acyl-CoA dehydrogenase deficiency. Diagnosis by stable-isotope dilution measurement of urinary n-hexanoylglycine and 3-phenylpropionylglycine. N Engl J Med. 1988 Nov 17;319(20):1308-13.
7. Penzien JM, Molz G, Wiesmann UN, Colombo JP, Buhlmann R, Wermuth B: Medium-chain acyl-CoA dehydrogenase deficiency does not correlate with apparent life-threatening events and the sudden infant death syndrome: results from phenylpropionate loading tests and DNA analysis. Eur J Pediatr. 1994 May;153(5):352-7.