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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-11-09 23:14:34 UTC
HMDB IDHMDB0000783
Secondary Accession Numbers
  • HMDB00783
Metabolite Identification
Common NamePropionylglycine
DescriptionPropionylglycine 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-acylglycineThe level of propionylglycine is elevated in patients with propionic acidemia, which is an inherited deficiency of propionyl-CoA carboxylase. (Disorders of propionate and methylmalonate metabolism. In The Metabolic and Molecular Bases of Inherited Disease).
Structure
Data?1582752156
Synonyms
ValueSource
2-Propanamidoacetic acidChEBI
N-Propionyl-glycineChEBI
N-PropionylglycineChEBI
Propanamidoacetic acidChEBI
PropanoylglycineChEBI
Propionylaminoacetic acidChEBI
2-PropanamidoacetateGenerator
PropanamidoacetateGenerator
PropionylaminoacetateGenerator
Chemical FormulaC5H9NO3
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
IUPAC Name2-propanamidoacetic acid
Traditional Namepropionylglycine
CAS Registry Number21709-90-0
SMILES
CCC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C5H9NO3/c1-2-4(7)6-3-5(8)9/h2-3H2,1H3,(H,6,7)(H,8,9)
InChI KeyWOMAZEJKVZLLFE-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
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot 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 Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg126.92830932474
[M-H]-Not Available126.928http://allccs.zhulab.cn/database/detail?ID=AllCCS00000033
Predicted Molecular Properties
PropertyValueSource
Water Solubility33.4 g/LALOGPS
logP-0.44ALOGPS
logP-0.63ChemAxon
logS-0.59ALOGPS
pKa (Strongest Acidic)3.93ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.07 m³·mol⁻¹ChemAxon
Polarizability12.6 ųChemAxon
Number of Rings0ChemAxon
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]+129.00331661259
DarkChem[M-H]-123.26131661259
AllCCS[M+H]+131.4232859911
AllCCS[M-H]-127.71132859911
DeepCCS[M+H]+128.52930932474
DeepCCS[M-H]-125.66530932474
DeepCCS[M-2H]-162.08630932474
DeepCCS[M+Na]+137.0730932474
AllCCS[M+H]+131.432859911
AllCCS[M+H-H2O]+127.332859911
AllCCS[M+NH4]+135.232859911
AllCCS[M+Na]+136.332859911
AllCCS[M-H]-127.732859911
AllCCS[M+Na-2H]-130.532859911
AllCCS[M+HCOO]-133.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PropionylglycineCCC(=O)NCC(O)=O2239.8Standard polar33892256
PropionylglycineCCC(=O)NCC(O)=O1241.0Standard non polar33892256
PropionylglycineCCC(=O)NCC(O)=O1401.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Propionylglycine,1TMS,isomer #1CCC(=O)NCC(=O)O[Si](C)(C)C1382.0Semi standard non polar33892256
Propionylglycine,1TMS,isomer #2CCC(=O)N(CC(=O)O)[Si](C)(C)C1385.1Semi standard non polar33892256
Propionylglycine,2TMS,isomer #1CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1418.5Semi standard non polar33892256
Propionylglycine,2TMS,isomer #1CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1427.5Standard non polar33892256
Propionylglycine,2TMS,isomer #1CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1560.6Standard polar33892256
Propionylglycine,1TBDMS,isomer #1CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C1622.9Semi standard non polar33892256
Propionylglycine,1TBDMS,isomer #2CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C1600.2Semi standard non polar33892256
Propionylglycine,2TBDMS,isomer #1CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1849.2Semi standard non polar33892256
Propionylglycine,2TBDMS,isomer #1CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1843.6Standard non polar33892256
Propionylglycine,2TBDMS,isomer #1CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1833.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Propionylglycine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-acef9a740ced48fb00e52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propionylglycine GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9200000000-3c7887407ce148e2cf1f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propionylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propionylglycine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propionylglycine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propionylglycine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Propionylglycine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-004i-9000000000-b5e80be4de97e1de49982012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propionylglycine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-9000000000-be56348c0dca03c022032012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propionylglycine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a4i-9000000000-39baca715a0a4ac09f6d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propionylglycine 40V, Positive-QTOFsplash10-0a4i-9000000000-a542f238b72f947107542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propionylglycine 35V, Positive-QTOFsplash10-0a4i-9000000000-f003324aa699706d41942021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propionylglycine 20V, Positive-QTOFsplash10-0a4i-9000000000-41c8ac7e6950711c9df32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propionylglycine 10V, Positive-QTOFsplash10-0a6r-9000000000-b0a4f15698d2fadefea42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propionylglycine 35V, Negative-QTOFsplash10-00di-9000000000-c7b66f7421e9853fc9942021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propionylglycine 10V, Positive-QTOFsplash10-053r-8900000000-60899826a66d302aa2372017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propionylglycine 20V, Positive-QTOFsplash10-0a6r-9000000000-a71e372fed182c0edcd02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propionylglycine 40V, Positive-QTOFsplash10-0a6r-9000000000-680ef8911029bf2b34212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propionylglycine 10V, Negative-QTOFsplash10-001i-2900000000-15bf873be2a495ed8e122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propionylglycine 20V, Negative-QTOFsplash10-0089-9800000000-e11bb20c11f7905d489f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propionylglycine 40V, Negative-QTOFsplash10-0ab9-9000000000-5714cacb51d7e4829db22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propionylglycine 10V, Positive-QTOFsplash10-004i-9000000000-f90d0d3f7ca3b7f6fcac2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propionylglycine 20V, Positive-QTOFsplash10-0a70-9000000000-b2276b1a1287ab61619d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propionylglycine 40V, Positive-QTOFsplash10-0a4i-9000000000-25bcb7a92417ed5e99382021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propionylglycine 10V, Negative-QTOFsplash10-00di-9100000000-0976ec7bea067ea09d0e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propionylglycine 20V, Negative-QTOFsplash10-05fr-9000000000-da3ce82cba870fdddfb22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propionylglycine 40V, Negative-QTOFsplash10-00dl-9000000000-fa643a49d9a9e8d5e94a2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • Physician's Guide...
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
UrineDetected and Quantified0.0864–0.3783 umol/mmol creatinineAdult (25-30 years old)Both
Not Available
details
UrineDetected and Quantified0.0591–0.4024 umol/mmol creatinineAdult (25-30 years old)Both
Not Available
details
UrineDetected and Quantified0.0609–0.6300 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 IDFDB022240
KNApSAcK IDNot Available
Chemspider ID89122
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5749
PubChem Compound98681
PDB IDNot Available
ChEBI ID89836
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKatz, J.; Lieberman, I.; Barker, H. A. Formation of propionyl-, butyryl-, and other acylglycines by enzymes of Clostridium kluyveri. Journal of Biological Chemistry (1953), 200 431-41.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bergstrom T, Greter J, Levin AH, Steen G, Tryding N, Wass U: Propionyl-CoA carboxylase deficiency: case report, effect of low-protein diet and identification of 3-oxo-2-methylvaleric acid 3-hydroxy-2-methylvaleric acid, and maleic acid in urine. Scand J Clin Lab Invest. 1981 Apr;41(2):117-26. [PubMed:7313494 ]
  2. Prasad C, Nurko S, Borovoy J, Korson MS: The importance of gut motility in the metabolic control of propionic acidemia. J Pediatr. 2004 Apr;144(4):532-5. [PubMed:15069406 ]
  3. (). Fenton, W.A., Gravel, R.A., Rosenblatt, D.S. Disorders of propionate and methylmalonate metabolism.. .
  4. (). Mayo Medical Laboratories 2005 Test Catalog. .

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