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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:08 UTC
HMDB IDHMDB0000747
Secondary Accession Numbers
  • HMDB00747
Metabolite Identification
Common NameIsovalerylalanine
DescriptionIsovalerylalanine, also known as isopentanoylalanine, 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. Isovalerylalanine results from the formal condensation of the carboxy group of isovaleric acid with the amino group of L-alanine. Isovalerylalanine is one of the constituents of the organic acid profile in isovaleric acidemia, it is believed to be formed by the action of the enzyme glycine N-acylase on alanine, using isovaleryl-CoA as a substrate (PMID: 6197208 ). Isovaleric acidemia was the first organic acid acidemia to be documented in humans. It is an autosomal recessive inborn error in the metabolism of leucine, caused by a deficiency of the mitochondrial enzyme isovaleryl-CoA dehydrogenase (IVD) that results in the accumulation isovaleryl-CoA derivatives (PMID: 16602101). The excess of isovaleryl-CoA in plasma allows for the formation of condensation derivatives, such as isovalerylalanine which makes it one of the biomarkers for this condition.
Structure
Data?1676999708
Synonyms
ValueSource
(2S)-2-(3-Methylbutanamido)propanoic acidChEBI
IsopentanoylalanineChEBI
N-Isopentanoyl-L-alanineChEBI
N-IsopentanoylalanineChEBI
N-IsovalerylalanineChEBI
(2S)-2-(3-Methylbutanamido)propanoateGenerator
N-Isovaleryl-L-alanineHMDB
IsovalerylalanineChEBI
Chemical FormulaC8H15NO3
Average Molecular Weight173.2096
Monoisotopic Molecular Weight173.105193351
IUPAC Name(2S)-2-(3-methylbutanamido)propanoic acid
Traditional Nameisovalerylalanine
CAS Registry Number68219-63-6
SMILES
CC(C)CC(=O)N[C@@H](C)C(O)=O
InChI Identifier
InChI=1S/C8H15NO3/c1-5(2)4-7(10)9-6(3)8(11)12/h5-6H,4H2,1-3H3,(H,9,10)(H,11,12)/t6-/m0/s1
InChI KeyOJPSNARFDYTAEN-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
  • Alanine or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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 Solubility11 g/LALOGPS
logP0.8ALOGPS
logP0.67ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.21ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.72 m³·mol⁻¹ChemAxon
Polarizability18.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.51331661259
DarkChem[M-H]-137.2831661259
AllCCS[M+H]+140.64432859911
AllCCS[M-H]-139.40832859911
DeepCCS[M+H]+144.61430932474
DeepCCS[M-H]-140.78530932474
DeepCCS[M-2H]-178.00730932474
DeepCCS[M+Na]+153.66930932474
AllCCS[M+H]+140.632859911
AllCCS[M+H-H2O]+136.932859911
AllCCS[M+NH4]+144.132859911
AllCCS[M+Na]+145.132859911
AllCCS[M-H]-139.432859911
AllCCS[M+Na-2H]-141.232859911
AllCCS[M+HCOO]-143.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsovalerylalanineCC(C)CC(=O)N[C@@H](C)C(O)=O2310.7Standard polar33892256
IsovalerylalanineCC(C)CC(=O)N[C@@H](C)C(O)=O1343.6Standard non polar33892256
IsovalerylalanineCC(C)CC(=O)N[C@@H](C)C(O)=O1430.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isovalerylalanine,1TMS,isomer #1CC(C)CC(=O)N[C@@H](C)C(=O)O[Si](C)(C)C1453.1Semi standard non polar33892256
Isovalerylalanine,1TMS,isomer #2CC(C)CC(=O)N([C@@H](C)C(=O)O)[Si](C)(C)C1477.4Semi standard non polar33892256
Isovalerylalanine,2TMS,isomer #1CC(C)CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1490.0Semi standard non polar33892256
Isovalerylalanine,2TMS,isomer #1CC(C)CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1479.7Standard non polar33892256
Isovalerylalanine,2TMS,isomer #1CC(C)CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1579.8Standard polar33892256
Isovalerylalanine,1TBDMS,isomer #1CC(C)CC(=O)N[C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C1688.3Semi standard non polar33892256
Isovalerylalanine,1TBDMS,isomer #2CC(C)CC(=O)N([C@@H](C)C(=O)O)[Si](C)(C)C(C)(C)C1704.1Semi standard non polar33892256
Isovalerylalanine,2TBDMS,isomer #1CC(C)CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1958.2Semi standard non polar33892256
Isovalerylalanine,2TBDMS,isomer #1CC(C)CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1909.1Standard non polar33892256
Isovalerylalanine,2TBDMS,isomer #1CC(C)CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1901.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isovalerylalanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9200000000-0941d93d8b73095be3712017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isovalerylalanine GC-MS (1 TMS) - 70eV, Positivesplash10-00bl-9310000000-ff31ec8bcd2f767edd932017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isovalerylalanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isovalerylalanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isovalerylalanine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isovalerylalanine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isovalerylalanine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylalanine 10V, Positive-QTOFsplash10-05i0-4900000000-279a1567e1a63ff40f7b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylalanine 20V, Positive-QTOFsplash10-0006-9200000000-75f940b78c284e853b5c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylalanine 40V, Positive-QTOFsplash10-0a4l-9000000000-84fea44c8d0eeaff90592017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylalanine 10V, Negative-QTOFsplash10-00di-1900000000-c44e3552766c93b103352017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylalanine 20V, Negative-QTOFsplash10-0fki-7900000000-1dbfe9bbc6b7b04d91a62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylalanine 40V, Negative-QTOFsplash10-05g3-9000000000-f37b9b82877a21760d9f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylalanine 10V, Negative-QTOFsplash10-000i-9300000000-bf002906104d17589e4f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylalanine 20V, Negative-QTOFsplash10-000i-9000000000-eee2c525ead39ccdd1b12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylalanine 40V, Negative-QTOFsplash10-000f-9000000000-8f8a6b36163eb8d3cef22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylalanine 10V, Positive-QTOFsplash10-0006-9200000000-ac4c7b8b294dbcda83552021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylalanine 20V, Positive-QTOFsplash10-0006-9000000000-49ba66e461e13d06ddf72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylalanine 40V, Positive-QTOFsplash10-0006-9000000000-7987039666b0de647c542021-09-22Wishart 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)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)2012-12-05Wishart 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 IDFDB022219
KNApSAcK IDNot Available
Chemspider ID114516
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5715
PubChem Compound129285
PDB IDNot Available
ChEBI ID136818
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceChen, Shu-Hui; Lamar, Jason; Guo, Deqi; Kohn, Todd; Yang, Hsiu-Chiung; McGee, James; Timm, David; Erickson, Jon; Yip, Yvonne; May, Patrick; McCarthy, James. P3 cap modified Phe*-Ala series BACE inhibitors. Bioorganic & Medicinal Chemistry Letters (2004), 14(1), 245-250.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lehnert W: N-Isovalerylalanine and N-isovalerylsarcosine: two new minor metabolites in isovaleric acidemia. Clin Chim Acta. 1983 Oct 31;134(1-2):207-12. [PubMed:6197208 ]