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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:17 UTC
HMDB IDHMDB0000894
Secondary Accession Numbers
  • HMDB0006723
  • HMDB0006724
  • HMDB00894
  • HMDB06723
  • HMDB06724
Metabolite Identification
Common NameVinylacetylglycine
DescriptionVinylacetylglycine 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. Vinylacetylglycine is a human metabolite that had been identified in a GC/MS urine screen. Increased amounts of this metabolite in the urine has been linked to a metabolomic disorder termed Isovaleric acidemia. (Gas-Chromatographic Method of Analysis for Urinary Organic Acids. I. Retention indices of 155 metaboically Important Compounds; Kay Tanaka, David G. Hine, Agnes West-Dull, and Theodore B. Lynn.).
Structure
Data?1676999717
Synonyms
ValueSource
2-(But-3-enamido)acetic acidChEBI
2-(But-3-enamido)acetateGenerator
Chemical FormulaC6H9NO3
Average Molecular Weight143.1406
Monoisotopic Molecular Weight143.058243159
IUPAC Name2-(but-3-enamido)acetic acid
Traditional Namebut-3-enamidoacetic acid
CAS Registry Number73122-61-9
SMILES
OC(=O)CNC(=O)CC=C
InChI Identifier
InChI=1S/C6H9NO3/c1-2-3-5(8)7-4-6(9)10/h2H,1,3-4H2,(H,7,8)(H,9,10)
InChI KeyUKISAGFGRDHYFO-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
  • N-acyl-amine
  • 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 Descriptors
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 Solubility55.3 g/LALOGPS
logP-0.48ALOGPS
logP-0.49ChemAxon
logS-0.41ALOGPS
pKa (Strongest Acidic)3.98ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.72 m³·mol⁻¹ChemAxon
Polarizability13.8 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]+131.88731661259
DarkChem[M-H]-128.69931661259
AllCCS[M+H]+133.3532859911
AllCCS[M-H]-129.72932859911
DeepCCS[M+H]+132.60130932474
DeepCCS[M-H]-130.28930932474
DeepCCS[M-2H]-166.18830932474
DeepCCS[M+Na]+141.10130932474
AllCCS[M+H]+133.332859911
AllCCS[M+H-H2O]+129.332859911
AllCCS[M+NH4]+137.132859911
AllCCS[M+Na]+138.232859911
AllCCS[M-H]-129.732859911
AllCCS[M+Na-2H]-132.032859911
AllCCS[M+HCOO]-134.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VinylacetylglycineOC(=O)CNC(=O)CC=C2334.0Standard polar33892256
VinylacetylglycineOC(=O)CNC(=O)CC=C1223.9Standard non polar33892256
VinylacetylglycineOC(=O)CNC(=O)CC=C1417.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Vinylacetylglycine,1TMS,isomer #1C=CCC(=O)NCC(=O)O[Si](C)(C)C1420.6Semi standard non polar33892256
Vinylacetylglycine,1TMS,isomer #2C=CCC(=O)N(CC(=O)O)[Si](C)(C)C1423.9Semi standard non polar33892256
Vinylacetylglycine,2TMS,isomer #1C=CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1462.2Semi standard non polar33892256
Vinylacetylglycine,2TMS,isomer #1C=CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1477.8Standard non polar33892256
Vinylacetylglycine,2TMS,isomer #1C=CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1645.5Standard polar33892256
Vinylacetylglycine,1TBDMS,isomer #1C=CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C1652.1Semi standard non polar33892256
Vinylacetylglycine,1TBDMS,isomer #2C=CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C1660.5Semi standard non polar33892256
Vinylacetylglycine,2TBDMS,isomer #1C=CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1918.9Semi standard non polar33892256
Vinylacetylglycine,2TBDMS,isomer #1C=CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1890.2Standard non polar33892256
Vinylacetylglycine,2TBDMS,isomer #1C=CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1924.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vinylacetylglycine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-9000000000-ee4dafe242d7b3a25b372017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vinylacetylglycine GC-MS (1 TMS) - 70eV, Positivesplash10-01bd-9200000000-d5452b4615c0101900f12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vinylacetylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vinylacetylglycine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vinylacetylglycine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vinylacetylglycine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Vinylacetylglycine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-9000000000-a3036bdbe74f1665bb9b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vinylacetylglycine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-014r-9000000000-d09a783c09e0f2b1061b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vinylacetylglycine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014r-9000000000-6c0914193049d59e43052012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vinylacetylglycine 10V, Positive-QTOFsplash10-002f-9800000000-5aefea4a1f59581279552017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vinylacetylglycine 20V, Positive-QTOFsplash10-056u-9000000000-7282b4d50a81e85e26fd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vinylacetylglycine 40V, Positive-QTOFsplash10-054o-9000000000-e011facd59167c71ef222017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vinylacetylglycine 10V, Negative-QTOFsplash10-0006-2900000000-62444f45e0908221bc672017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vinylacetylglycine 20V, Negative-QTOFsplash10-006x-9700000000-8371d2bb5ea318537d212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vinylacetylglycine 40V, Negative-QTOFsplash10-05fu-9000000000-69be79618946966c31c72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vinylacetylglycine 10V, Positive-QTOFsplash10-0006-9000000000-279914ea2f886d4d7d282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vinylacetylglycine 20V, Positive-QTOFsplash10-00kf-9000000000-bfb50c5c1402d0b8ef302021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vinylacetylglycine 40V, Positive-QTOFsplash10-052f-9000000000-8a0e8da17968af912e482021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vinylacetylglycine 10V, Negative-QTOFsplash10-0002-9200000000-793087dba3b379b67ea72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vinylacetylglycine 20V, Negative-QTOFsplash10-006t-9000000000-0f9e57db8b82bb8feae42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vinylacetylglycine 40V, Negative-QTOFsplash10-00dl-9000000000-0860c46254feca10147d2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart 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 LocationsNot Available
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 IDFDB022303
KNApSAcK IDNot Available
Chemspider ID27976741
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5851
PubChem Compound53477718
PDB IDNot Available
ChEBI ID74435
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, Baretz BH, Tanaka K: Mass spectrometric studies of twenty-one metabolically important acylglycines. Biomed Mass Spectrom. 1977 Aug;4(4):220-5. [PubMed:912020 ]

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