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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 11:46:43 UTC
Update Date2021-09-14 15:46:13 UTC
HMDB IDHMDB0006488
Secondary Accession Numbers
  • HMDB06488
Metabolite Identification
Common NameN-Acetyl-L-glutamate 5-semialdehyde
DescriptionN-Acetyl-L-glutamate 5-semialdehyde, also known as 2-acetamido-5-oxovaleric acid or N-acetyl-5-oxo-L-norvaline, belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-Acetyl-L-glutamate 5-semialdehyde exists in all living species, ranging from bacteria to plants to humans. N-Acetyl-L-glutamate 5-semialdehyde has been detected, but not quantified in, several different foods, such as mixed nuts, yams (Dioscorea), bulgur, pepper (capsicum), and wampees (Clausena lansium). This could make N-acetyl-L-glutamate 5-semialdehyde a potential biomarker for the consumption of these foods. N-Acetyl-L-glutamate 5-semialdehyde is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on N-Acetyl-L-glutamate 5-semialdehyde.
Structure
Data?1592325841
Synonyms
ValueSource
2-Acetamido-5-oxovaleric acidChEBI
N-Acetyl-5-oxo-L-norvalineChEBI
2-Acetamido-5-oxopentanoateKegg
2-Acetamido-5-oxovalerateGenerator
2-Acetamido-5-oxopentanoic acidGenerator
N-Acetyl-L-glutamic acid 5-semialdehydeGenerator
N-Acetyl-L-glutamic acid gamma-semialdehydeMeSH, HMDB
Chemical FormulaC7H11NO4
Average Molecular Weight173.1665
Monoisotopic Molecular Weight173.068807845
IUPAC Name(2S)-2-acetamido-5-oxopentanoic acid
Traditional NameN-acetyl-5-oxo-L-norvaline
CAS Registry Number13074-21-0
SMILES
CC(=O)N[C@@H](CCC=O)C(O)=O
InChI Identifier
InChI=1S/C7H11NO4/c1-5(10)8-6(7(11)12)3-2-4-9/h4,6H,2-3H2,1H3,(H,8,10)(H,11,12)/t6-/m0/s1
InChI KeyBCPSFKBPHHBDAI-LURJTMIESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-L-alpha-amino acids
Alternative Parents
Substituents
  • N-acyl-l-alpha-amino acid
  • Fatty acid
  • Alpha-hydrogen aldehyde
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aldehyde
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

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 Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility18.6 g/LALOGPS
logP10(-0.43) g/LALOGPS
logP10(-1.3) g/LChemAxon
logS10(-0.97) g/LALOGPS
pKa (Strongest Acidic)3.72ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.47 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.81 m³·mol⁻¹ChemAxon
Polarizability16.46 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]+140.91831661259
DarkChem[M-H]-137.85731661259
DeepCCS[M+H]+135.28930932474
DeepCCS[M-H]-131.80530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Acetyl-L-glutamate 5-semialdehydeCC(=O)N[C@@H](CCC=O)C(O)=O2556.9Standard polar33892256
N-Acetyl-L-glutamate 5-semialdehydeCC(=O)N[C@@H](CCC=O)C(O)=O1406.4Standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehydeCC(=O)N[C@@H](CCC=O)C(O)=O1563.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetyl-L-glutamate 5-semialdehyde,1TMS,isomer #1CC(=O)N[C@@H](CCC=O)C(=O)O[Si](C)(C)C1540.8Semi standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,1TMS,isomer #2CC(=O)N[C@@H](CC=CO[Si](C)(C)C)C(=O)O1692.8Semi standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,1TMS,isomer #3CC(=O)N([C@@H](CCC=O)C(=O)O)[Si](C)(C)C1539.5Semi standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #1CC(=O)N[C@@H](CC=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C1731.9Semi standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #1CC(=O)N[C@@H](CC=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C1704.3Standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #1CC(=O)N[C@@H](CC=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C2146.6Standard polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #2CC(=O)N([C@@H](CCC=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C1566.5Semi standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #2CC(=O)N([C@@H](CCC=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C1594.2Standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #2CC(=O)N([C@@H](CCC=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C1875.3Standard polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #3CC(=O)N([C@@H](CC=CO[Si](C)(C)C)C(=O)O)[Si](C)(C)C1710.8Semi standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #3CC(=O)N([C@@H](CC=CO[Si](C)(C)C)C(=O)O)[Si](C)(C)C1757.1Standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #3CC(=O)N([C@@H](CC=CO[Si](C)(C)C)C(=O)O)[Si](C)(C)C2153.2Standard polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,3TMS,isomer #1CC(=O)N([C@@H](CC=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1719.9Semi standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,3TMS,isomer #1CC(=O)N([C@@H](CC=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1771.4Standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,3TMS,isomer #1CC(=O)N([C@@H](CC=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1902.3Standard polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,1TBDMS,isomer #1CC(=O)N[C@@H](CCC=O)C(=O)O[Si](C)(C)C(C)(C)C1766.9Semi standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,1TBDMS,isomer #2CC(=O)N[C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O1938.9Semi standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,1TBDMS,isomer #3CC(=O)N([C@@H](CCC=O)C(=O)O)[Si](C)(C)C(C)(C)C1773.9Semi standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #1CC(=O)N[C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2133.0Semi standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #1CC(=O)N[C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2136.6Standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #1CC(=O)N[C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2304.2Standard polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #2CC(=O)N([C@@H](CCC=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2036.7Semi standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #2CC(=O)N([C@@H](CCC=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2043.7Standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #2CC(=O)N([C@@H](CCC=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2126.2Standard polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #3CC(=O)N([C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2179.4Semi standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #3CC(=O)N([C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2179.6Standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #3CC(=O)N([C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2318.6Standard polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,3TBDMS,isomer #1CC(=O)N([C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2366.2Semi standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,3TBDMS,isomer #1CC(=O)N([C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2406.6Standard non polar33892256
N-Acetyl-L-glutamate 5-semialdehyde,3TBDMS,isomer #1CC(=O)N([C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2237.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9500000000-209b524fd8ef1d9e627f2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9420000000-8d264158e366f88d5d3e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 10V, Positive-QTOFsplash10-05fr-1900000000-cfaeff3cecd86134fd582015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 20V, Positive-QTOFsplash10-055r-6900000000-bb54f50a29e9a351858c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 40V, Positive-QTOFsplash10-02a6-9100000000-fe9c1618b7f81c2f9d5b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 10V, Negative-QTOFsplash10-00di-0900000000-f6338ed4d753ef0b744e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 20V, Negative-QTOFsplash10-0m89-3900000000-b5fbc1c314380afa8cc12015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 40V, Negative-QTOFsplash10-052f-9100000000-a529029ad524b613c9902015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 10V, Positive-QTOFsplash10-01q9-0900000000-1f0440fa922d5815c5d92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 20V, Positive-QTOFsplash10-03e9-5900000000-b295f71616c68600654d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 40V, Positive-QTOFsplash10-0006-9000000000-0d07a69d508963a4c2462021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 10V, Negative-QTOFsplash10-001i-2900000000-d1bb675eb0f08dff73042021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 20V, Negative-QTOFsplash10-01q9-3900000000-a872856bc77482a41b252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 40V, Negative-QTOFsplash10-052f-9000000000-76a9b5ce42ea1d2112d22021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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
Biological Properties
Cellular Locations
  • Mitochondria
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 IDFDB023938
KNApSAcK IDNot Available
Chemspider ID167387
KEGG Compound IDC01250
BioCyc IDCPD-469
BiGG ID37191
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound192878
PDB IDNot Available
ChEBI ID16319
Food Biomarker OntologyNot Available
VMH IDACG5SA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available