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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:27 UTC
HMDB IDHMDB0000860
Secondary Accession Numbers
  • HMDB00860
Metabolite Identification
Common NamePhenylpropionylglycine
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 ).
Structure
Data?1582752160
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 Weight207.2258
Monoisotopic Molecular Weight207.089543287
IUPAC Name2-(3-phenylpropanamido)acetic acid
Traditional Namephenylpropionylglycine
CAS Registry Number56613-60-6
SMILES
OC(=O)CNC(=O)CCC1=CC=CC=C1
InChI Identifier
InChI=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
Ontology
Physiological effect

Adverse health effect

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 Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M-H]-MetCCS_train_neg153.29730932474
AllCCS[M-H]-Not Available153.297http://allccs.zhulab.cn/database/detail?ID=AllCCS00000036
AllCCS[M+H]+Not Available149.466http://allccs.zhulab.cn/database/detail?ID=AllCCS00000036
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP10(0.93) g/LALOGPS
logP10(0.95) g/LChemAxon
logS10(-2.9) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.98731661259
DarkChem[M-H]-145.45531661259
AllCCS[M+H]+145.40932859911
AllCCS[M-H]-147.79532859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phenylpropionylglycine,1TMS,#1C[Si](C)(C)OC(=O)CNC(=O)CCC1=CC=CC=C12024.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Phenylpropionylglycine,1TMS,#2C[Si](C)(C)N(CC(=O)O)C(=O)CCC1=CC=CC=C11994.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Phenylpropionylglycine,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CCC1=CC=CC=C12271.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Phenylpropionylglycine,1TBDMS,#2CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)CCC1=CC=CC=C12215.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phenylpropionylglycine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-6900000000-49e6bd1ae55ef730be572017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenylpropionylglycine GC-MS (1 TMS) - 70eV, Positivesplash10-03l3-7910000000-288e575c4d82667708e62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenylpropionylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropionylglycine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-056r-9510000000-857882337db8707be6da2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropionylglycine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-3900000000-ac64df3f4f25d003198b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropionylglycine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-056u-9400000000-ba5317e2dcb281f5ad7f2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropionylglycine 20V, Negative-QTOFsplash10-00di-9000000000-5232244a5f1e32f44bfa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropionylglycine 10V, Negative-QTOFsplash10-00di-9120000000-3ad79b9ff64c3f9402d42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropionylglycine 40V, Negative-QTOFsplash10-00di-9000000000-952c82e2b34ef96383e82021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropionylglycine 10V, Positive-QTOFsplash10-0a4i-5980000000-e671cd58f497ac7faac92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropionylglycine 20V, Positive-QTOFsplash10-0a6r-9600000000-f46c69e1694bd406aed72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropionylglycine 40V, Positive-QTOFsplash10-0a6r-9300000000-614fceaf9ffefb2012332017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropionylglycine 10V, Negative-QTOFsplash10-0a4i-0390000000-aa434ae4ae70d3eae4bf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropionylglycine 20V, Negative-QTOFsplash10-0ab9-6970000000-55314833bc2ceca004c02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropionylglycine 40V, Negative-QTOFsplash10-0ab9-9200000000-26dcb24e7bc9b913dd222017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropionylglycine 10V, Negative-QTOFsplash10-0a4i-1690000000-8b2f04f031ae7c4b49e22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropionylglycine 20V, Negative-QTOFsplash10-0a4l-8910000000-18d0ad5b9e5aa8c4284c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropionylglycine 40V, Negative-QTOFsplash10-004l-9100000000-9feb6c67f526b26df3732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropionylglycine 10V, Positive-QTOFsplash10-0a4l-3920000000-f55c3c8e5ea50cbea7242021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropionylglycine 20V, Positive-QTOFsplash10-0a4l-8900000000-da57702d9fb756c9d7e32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropionylglycine 40V, Positive-QTOFsplash10-0a6u-9600000000-6de90f0cc8c6eaf079f42021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified<0.0010–0.0656 umol/mmol creatinineAdult (25-30 years old)Both
Not Available
details
UrineDetected and Quantified<0.0010–0.0657 umol/mmol creatinineAdult (25-30 years old)Both
Not Available
details
UrineDetected and Quantified0.0020–0.0573 umol/mmol creatinineAdult (25-30 years old)Both
Not Available
details
UrineDetected but not QuantifiedNot QuantifiedAdult (24-38years old)Not SpecifiedNormal details
UrineDetected and Quantified0.01 (0-0-42) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified<0.13 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified1.00 (0.00-2.00) umol/mmol creatinineAdult (>18 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency
    • MetaGene: Metabol...
details
UrineDetected and Quantified0.03 umol/mmol creatinineAdult (>18 years old)Not Specified
Propionic acidemia
details
UrineDetected and Quantified3.819 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified12.00295 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified18.00442 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified20.732 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified32.735 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
Associated Disorders and Diseases
Disease References
Medium Chain Acyl-CoA Dehydrogenase Deficiency
  1. 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 ]
  2. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Propionic acidemia
  1. Riemersma M, Hazebroek MR, Helderman-van den Enden ATJM, Salomons GS, Ferdinandusse S, Brouwers MCGJ, van der Ploeg L, Heymans S, Glatz JFC, van den Wijngaard A, Krapels IPC, Bierau J, Brunner HG: Propionic acidemia as a cause of adult-onset dilated cardiomyopathy. Eur J Hum Genet. 2017 Nov;25(11):1195-1201. doi: 10.1038/ejhg.2017.127. Epub 2017 Aug 30. [PubMed:28853722 ]
Associated OMIM IDs
  • 201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
  • 606054 (Propionic acidemia)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022286
KNApSAcK IDNot Available
Chemspider ID134261
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5823
PubChem Compound152323
PDB IDNot Available
ChEBI ID266653
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029990
Good Scents IDNot Available
References
Synthesis ReferenceGeurts, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:1779616 ]
  2. 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. [PubMed:6722284 ]
  3. 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. [PubMed:9234867 ]
  4. 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. [PubMed:7967471 ]
  5. 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. [PubMed:3054550 ]
  6. 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. [PubMed:8033926 ]

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