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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:29 UTC
Update Date2020-02-26 21:37:03 UTC
HMDB IDHMDB0012175
Secondary Accession Numbers
  • HMDB12175
Metabolite Identification
Common Name5-Acetamidovalerate
Description5-Acetamidovalerate is involved in the lysine degradation III pathway. It can be generated from the enzymatic reduction of 5-aminopentanoate or enzymatic oxidation of 2-keto-6-acetamidocaproate. Experiment using DL-{4,5-3H}lysine showed 5-acetamidovalerate as the major product. If radiolabeled N6-acetyl-L-lysine was used with added α-ketoglutarate, and pyridoxal phosphate, radiolabeled 2-keto-6-acetamidocaproate was produced. α-Ketoglutarate was preferred over pyruvate, and there was little or no dependence on pyridoxal phosphate. If thiamine pyrophosphate and NAD were added to a similar reaction, virtually all of the label was in 5-acetamidovalerate. If labeled 5-acetamidovalerate was used, labeled 5-aminovalerate (5-aminopentanoate) was identified. In addition, whole cell cultures of R. leguminicola incubated with labeled 5-acetamidovalerate accumulated radiolabeled glutarate. Whole cell cultures incubated with radiolabeled glutarate produced a mixture of tricarboxylic acid cycle acids and other carboxylic acids.
Structure
Data?1582753023
Synonyms
ValueSource
5-Acetamidovaleric acidGenerator
5-AcetamidopentanoateHMDB
5-Acetamidopentanoic acidHMDB
Chemical FormulaC7H13NO3
Average Molecular Weight159.183
Monoisotopic Molecular Weight159.089543287
IUPAC Name5-acetamidopentanoic acid
Traditional Name5-acetamidopentanoic acid
CAS Registry NumberNot Available
SMILES
CC(=O)NCCCCC(O)=O
InChI Identifier
InChI=1S/C7H13NO3/c1-6(9)8-5-3-2-4-7(10)11/h2-5H2,1H3,(H,8,9)(H,10,11)
InChI KeyTZZSWAXSIGWXOS-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
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.38 g/LALOGPS
logP-0.07ALOGPS
logP-0.36ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.59ChemAxon
pKa (Strongest Basic)-0.63ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.5 m³·mol⁻¹ChemAxon
Polarizability16.88 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-a0c945a55189dc0b5f84Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00r6-9300000000-db46ea751d90a55021d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gvo-0900000000-81e251b1e76b54d2d776Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-4900000000-98a16f866bc20ccf222bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-6b007ccfdfff6745a5caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-aecd97b33c6bf04fdca4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-6900000000-9bd2790a6596e2944e71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-603ec01906bf2465ceddSpectrum
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 IDFDB028829
KNApSAcK IDNot Available
Chemspider ID388937
KEGG Compound IDC03087
BioCyc ID5-ACETAMIDOVALERATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439903
PDB IDNot Available
ChEBI ID2024
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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.