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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-01-27 11:06:50 UTC
Update Date2020-02-26 21:23:31 UTC
HMDB IDHMDB0001843
Secondary Accession Numbers
  • HMDB01843
Metabolite Identification
Common NameN-Acryloylglycine
DescriptionN-Acryloylglycine 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. N-Acryloylglycine is an acylglycines found in normal human biofluids (PMID 7364920 ; 912020; 7438429).
Structure
Data?1582752211
Synonyms
ValueSource
1-Aminopropenal acetic acidHMDB
N-(1-oxo-2-Propenyl)-glycineHMDB
N-Acryloyl-glycineHMDB
APAAHMDB
2-[(1-Hydroxyprop-2-en-1-ylidene)amino]acetateHMDB
Chemical FormulaC5H7NO3
Average Molecular Weight129.114
Monoisotopic Molecular Weight129.042593095
IUPAC Name2-(prop-2-enamido)acetic acid
Traditional NameN-acryloylglycine
CAS Registry Number24599-25-5
SMILES
OC(=O)CNC(=O)C=C
InChI Identifier
InChI=1S/C5H7NO3/c1-2-4(7)6-3-5(8)9/h2H,1,3H2,(H,6,7)(H,8,9)
InChI KeyLZCXCXDOGAEFQX-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
  • Acrylic acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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 Solubility63.6 g/LALOGPS
logP-0.28ALOGPS
logP-0.57ChemAxon
logS-0.31ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
pKa (Strongest Basic)-0.63ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.09 m³·mol⁻¹ChemAxon
Polarizability11.92 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]+126.59831661259
DarkChem[M-H]-122.02131661259
AllCCS[M+H]+130.432859911
AllCCS[M-H]-125.55232859911
DeepCCS[M+H]+124.03930932474
DeepCCS[M-H]-120.6530932474
DeepCCS[M-2H]-157.79230932474
DeepCCS[M+Na]+132.91130932474
AllCCS[M+H]+130.432859911
AllCCS[M+H-H2O]+126.332859911
AllCCS[M+NH4]+134.332859911
AllCCS[M+Na]+135.432859911
AllCCS[M-H]-125.632859911
AllCCS[M+Na-2H]-128.332859911
AllCCS[M+HCOO]-131.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-AcryloylglycineOC(=O)CNC(=O)C=C2071.0Standard polar33892256
N-AcryloylglycineOC(=O)CNC(=O)C=C1106.5Standard non polar33892256
N-AcryloylglycineOC(=O)CNC(=O)C=C1388.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acryloylglycine,1TMS,isomer #1C=CC(=O)NCC(=O)O[Si](C)(C)C1371.3Semi standard non polar33892256
N-Acryloylglycine,1TMS,isomer #2C=CC(=O)N(CC(=O)O)[Si](C)(C)C1404.6Semi standard non polar33892256
N-Acryloylglycine,2TMS,isomer #1C=CC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1418.8Semi standard non polar33892256
N-Acryloylglycine,2TMS,isomer #1C=CC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1386.7Standard non polar33892256
N-Acryloylglycine,2TMS,isomer #1C=CC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1571.5Standard polar33892256
N-Acryloylglycine,1TBDMS,isomer #1C=CC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C1631.2Semi standard non polar33892256
N-Acryloylglycine,1TBDMS,isomer #2C=CC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C1627.1Semi standard non polar33892256
N-Acryloylglycine,2TBDMS,isomer #1C=CC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1878.2Semi standard non polar33892256
N-Acryloylglycine,2TBDMS,isomer #1C=CC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1801.9Standard non polar33892256
N-Acryloylglycine,2TBDMS,isomer #1C=CC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1854.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Acryloylglycine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-5696c0e42a06c47cf8b72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acryloylglycine GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9100000000-24a928243f8f9100db112017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acryloylglycine 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 - N-Acryloylglycine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-053r-9300000000-2802258cfc542054fcb42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acryloylglycine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-9000000000-7e7bd17503bfa7395d452012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acryloylglycine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a4i-9000000000-285bc2264e30ec8661e62012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acryloylglycine 10V, Positive-QTOFsplash10-053r-9800000000-8a9d3ec8bd310d5e10542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acryloylglycine 20V, Positive-QTOFsplash10-0a6r-9000000000-2e90beda6bee67bb94932017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acryloylglycine 40V, Positive-QTOFsplash10-0a6r-9000000000-4d8ae6a5538548b2ff802017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acryloylglycine 10V, Negative-QTOFsplash10-004i-2900000000-180967d33262d5a621152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acryloylglycine 20V, Negative-QTOFsplash10-00b9-9700000000-826ef5ca3fe09b06deb82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acryloylglycine 40V, Negative-QTOFsplash10-0ab9-9000000000-88dc019451d6fff02eec2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acryloylglycine 10V, Positive-QTOFsplash10-053r-9000000000-6ade5e377c74732a46732021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acryloylglycine 20V, Positive-QTOFsplash10-053r-9000000000-567c6ce87890d5f221462021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acryloylglycine 40V, Positive-QTOFsplash10-0a4i-9000000000-8a5d1614f47f2b0cf6a42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acryloylglycine 10V, Negative-QTOFsplash10-001i-9100000000-248ae8281c13b7a1405c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acryloylglycine 20V, Negative-QTOFsplash10-053r-9000000000-8e94320e0e497fc726e72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acryloylglycine 40V, Negative-QTOFsplash10-05fu-9000000000-2f13c8b54478f07e39ba2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
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
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 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 IDFDB022703
KNApSAcK IDNot Available
Chemspider ID90657
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6343
PubChem Compound100321
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. Ramsdell HS, Tanak K: Gas chromatographic retention indices of twenty metabolically important acylglycines as trimethylsilyl derivatives. J Chromatogr. 1980 Jan 11;181(1):90-4. [PubMed:7364920 ]

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