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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:27 UTC
Update Date2022-03-07 02:51:22 UTC
HMDB IDHMDB0012233
Secondary Accession Numbers
  • HMDB12233
Metabolite Identification
Common NameGlutarate semialdehyde
DescriptionIn the lysine degradation IV pathway, glutarate semialdehyde reacts with NADP+ and H2O to produce glutarate, NADPH, and H+. In this pathway, glutarate semialdehyde is produced by the reaction between 5-aminopentanoate and 2-ketoglutarate, with L-glutamate as a byproduct. The enzyme responsible for this reaction is 5-aminovalerate aminotransferase. In the lysine degradation III pathway, glutarate semialdehyde reacts with NAD+ and H2O to produce glutarate and NADH. In this pathway, glutarate semialdehyde is produced by the reaction between 5-aminopentanoate and 2-ketoglutarate, with L-glutamate as a byproduct. The enzyme responsible for this reaction is 5-aminovalerate aminotransferase.
Structure
Data?1582753031
Synonyms
ValueSource
2-Formylethylacetic acidChEBI
4-Formylbutyric acidChEBI
5-oxo-ValeriansaeureChEBI
5-oxo-Valeric acidChEBI
5-OxopentanoateChEBI
5-Oxovaleric acidChEBI
2-FormylethylacetateGenerator
4-FormylbutyrateGenerator
5-oxo-ValerateGenerator
5-Oxopentanoic acidGenerator
5-OxovalerateGenerator
Glutaric acid semialdehydeGenerator
5-oxo-PentanoateHMDB, Generator
5-oxo-Pentanoic acidHMDB
Glutarate semialdehydeChEBI
Chemical FormulaC5H8O3
Average Molecular Weight116.1152
Monoisotopic Molecular Weight116.047344122
IUPAC Name5-oxopentanoic acid
Traditional Name5-oxopentanoic acid
CAS Registry Number5746-02-1
SMILES
OC(=O)CCCC=O
InChI Identifier
InChI=1S/C5H8O3/c6-4-2-1-3-5(7)8/h4H,1-3H2,(H,7,8)
InChI KeyVBKPPDYGFUZOAJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentStraight chain fatty acids
Alternative Parents
Substituents
  • Straight chain fatty acid
  • Alpha-hydrogen aldehyde
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

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 Solubility103 g/LALOGPS
logP-0.07ALOGPS
logP-0.11ChemAxon
logS-0.05ALOGPS
pKa (Strongest Acidic)4.33ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity27.21 m³·mol⁻¹ChemAxon
Polarizability11.26 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]+124.21531661259
DarkChem[M-H]-120.29931661259
DeepCCS[M+H]+125.90430932474
DeepCCS[M-H]-123.76430932474
DeepCCS[M-2H]-159.37130932474
DeepCCS[M+Na]+134.15730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Glutarate semialdehydeOC(=O)CCCC=O2214.9Standard polar33892256
Glutarate semialdehydeOC(=O)CCCC=O926.1Standard non polar33892256
Glutarate semialdehydeOC(=O)CCCC=O1087.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glutarate semialdehyde,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCC=O1177.4Semi standard non polar33892256
Glutarate semialdehyde,1TMS,isomer #2C[Si](C)(C)OC=CCCC(=O)O1303.2Semi standard non polar33892256
Glutarate semialdehyde,2TMS,isomer #1C[Si](C)(C)OC=CCCC(=O)O[Si](C)(C)C1368.1Semi standard non polar33892256
Glutarate semialdehyde,2TMS,isomer #1C[Si](C)(C)OC=CCCC(=O)O[Si](C)(C)C1341.9Standard non polar33892256
Glutarate semialdehyde,2TMS,isomer #1C[Si](C)(C)OC=CCCC(=O)O[Si](C)(C)C1435.0Standard polar33892256
Glutarate semialdehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC=O1411.9Semi standard non polar33892256
Glutarate semialdehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=CCCC(=O)O1537.8Semi standard non polar33892256
Glutarate semialdehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCC(=O)O[Si](C)(C)C(C)(C)C1783.9Semi standard non polar33892256
Glutarate semialdehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCC(=O)O[Si](C)(C)C(C)(C)C1785.2Standard non polar33892256
Glutarate semialdehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCC(=O)O[Si](C)(C)C(C)(C)C1705.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Glutarate semialdehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9000000000-d31fc19221f57a1260962017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glutarate semialdehyde GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9300000000-3c7940e0ecc4c8f8e47e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glutarate 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 - Glutarate semialdehyde 10V, Positive-QTOFsplash10-0002-9200000000-f7b6804cb8f91e8494df2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutarate semialdehyde 20V, Positive-QTOFsplash10-006t-9000000000-4849c70b25a2d4f8af7c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutarate semialdehyde 40V, Positive-QTOFsplash10-054o-9000000000-7421063eb00645aa22832017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutarate semialdehyde 10V, Negative-QTOFsplash10-014i-5900000000-c1f4c5abe2f30f8c5b312017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutarate semialdehyde 20V, Negative-QTOFsplash10-014j-9400000000-a3a1cefada4e242ec22f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutarate semialdehyde 40V, Negative-QTOFsplash10-0006-9000000000-b82291299befed9ad4c52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutarate semialdehyde 10V, Positive-QTOFsplash10-006y-9000000000-2e6eade4cb5067e0ff572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutarate semialdehyde 20V, Positive-QTOFsplash10-0596-9000000000-5ccdfa4d862c64289ea52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutarate semialdehyde 40V, Positive-QTOFsplash10-0006-9000000000-233295c53b43e378a2772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutarate semialdehyde 10V, Negative-QTOFsplash10-0002-9100000000-832bd65f9e6872e77aad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutarate semialdehyde 20V, Negative-QTOFsplash10-0007-9000000000-2893696f938f857ab95d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutarate semialdehyde 40V, Negative-QTOFsplash10-0006-9000000000-7f6df800f91cc51402a12021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB028876
KNApSAcK IDNot Available
Chemspider ID388989
KEGG Compound IDC03273
BioCyc IDCPD-654
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439963
PDB IDNot Available
ChEBI ID39153
Food Biomarker OntologyNot Available
VMH IDOXPTN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.