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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-04-06 16:20:29 UTC
Update Date2023-02-21 17:17:42 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?1676999862
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
Physiological effectNot Available
Disposition
Process
Role
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 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.97331661259
DarkChem[M-H]-130.50731661259
DeepCCS[M+H]+133.67430932474
DeepCCS[M-H]-130.23430932474
DeepCCS[M-2H]-166.8430932474
DeepCCS[M+Na]+142.26830932474
AllCCS[M+H]+136.032859911
AllCCS[M+H-H2O]+132.132859911
AllCCS[M+NH4]+139.632859911
AllCCS[M+Na]+140.732859911
AllCCS[M-H]-135.532859911
AllCCS[M+Na-2H]-137.432859911
AllCCS[M+HCOO]-139.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-AcetamidovalerateCC(=O)NCCCCC(O)=O2474.8Standard polar33892256
5-AcetamidovalerateCC(=O)NCCCCC(O)=O1605.2Standard non polar33892256
5-AcetamidovalerateCC(=O)NCCCCC(O)=O1600.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Acetamidovalerate,1TMS,isomer #1CC(=O)NCCCCC(=O)O[Si](C)(C)C1586.0Semi standard non polar33892256
5-Acetamidovalerate,1TMS,isomer #2CC(=O)N(CCCCC(=O)O)[Si](C)(C)C1606.5Semi standard non polar33892256
5-Acetamidovalerate,2TMS,isomer #1CC(=O)N(CCCCC(=O)O[Si](C)(C)C)[Si](C)(C)C1613.9Semi standard non polar33892256
5-Acetamidovalerate,2TMS,isomer #1CC(=O)N(CCCCC(=O)O[Si](C)(C)C)[Si](C)(C)C1661.7Standard non polar33892256
5-Acetamidovalerate,2TMS,isomer #1CC(=O)N(CCCCC(=O)O[Si](C)(C)C)[Si](C)(C)C1781.5Standard polar33892256
5-Acetamidovalerate,1TBDMS,isomer #1CC(=O)NCCCCC(=O)O[Si](C)(C)C(C)(C)C1835.7Semi standard non polar33892256
5-Acetamidovalerate,1TBDMS,isomer #2CC(=O)N(CCCCC(=O)O)[Si](C)(C)C(C)(C)C1819.1Semi standard non polar33892256
5-Acetamidovalerate,2TBDMS,isomer #1CC(=O)N(CCCCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2079.8Semi standard non polar33892256
5-Acetamidovalerate,2TBDMS,isomer #1CC(=O)N(CCCCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2087.7Standard non polar33892256
5-Acetamidovalerate,2TBDMS,isomer #1CC(=O)N(CCCCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2036.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Acetamidovalerate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-a0c945a55189dc0b5f842017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Acetamidovalerate GC-MS (1 TMS) - 70eV, Positivesplash10-00r6-9300000000-db46ea751d90a55021d92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Acetamidovalerate 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 - 5-Acetamidovalerate 10V, Positive-QTOFsplash10-0gvo-0900000000-81e251b1e76b54d2d7762017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetamidovalerate 20V, Positive-QTOFsplash10-0udi-4900000000-98a16f866bc20ccf222b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetamidovalerate 40V, Positive-QTOFsplash10-0a4l-9000000000-6b007ccfdfff6745a5ca2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetamidovalerate 10V, Negative-QTOFsplash10-0a4i-1900000000-aecd97b33c6bf04fdca42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetamidovalerate 20V, Negative-QTOFsplash10-0a4i-6900000000-9bd2790a6596e2944e712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetamidovalerate 40V, Negative-QTOFsplash10-052f-9000000000-603ec01906bf2465cedd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetamidovalerate 10V, Positive-QTOFsplash10-03di-0900000000-8862d840bf7881285eb82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetamidovalerate 20V, Positive-QTOFsplash10-0kmi-9300000000-7afa196912756b5f41d72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetamidovalerate 40V, Positive-QTOFsplash10-0a4i-9000000000-61d7a43928ef50a8d2672021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetamidovalerate 10V, Negative-QTOFsplash10-0005-9800000000-bec529e5ccfbe11569212021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetamidovalerate 20V, Negative-QTOFsplash10-0002-9100000000-4a3501ef9152bb3168672021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetamidovalerate 40V, Negative-QTOFsplash10-052f-9000000000-37570202422e908429892021-09-24Wishart 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

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 Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
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 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.