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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:38 UTC
Update Date2021-09-07 16:45:32 UTC
HMDB IDHMDB0002141
Secondary Accession Numbers
  • HMDB02141
Metabolite Identification
Common NameN-Methyl-a-aminoisobutyric acid
DescriptionN-Methyl-a-aminoisobutyric acid, also known as 2-(methylamino)isobutyrate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). N-Methyl-a-aminoisobutyric acid is a drug. N-Methyl-a-aminoisobutyric acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make N-methyl-a-aminoisobutyric acid a potential biomarker for the consumption of these foods. N-Methyl-a-aminoisobutyric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on N-Methyl-a-aminoisobutyric acid.
Structure
Data?1582752231
Synonyms
ValueSource
2-(Methylamino)isobutyric acidChEBI
2-(Methylamino)isobutyrateGenerator
N-Methyl-a-aminoisobutyrateGenerator
N-Methylaminoisobutyric acidChEMBL, HMDB
N-MethylaminoisobutyrateGenerator, HMDB
N-Methyl-alpha-aminoisobutyrateHMDB, Generator
N-Methyl-alpha-aminoisobutyric acidHMDB
N-(methylamino)Isobutyric acidMeSH, HMDB
AMAIBMeSH, HMDB
N-Methyl alpha-aminoisobutyric acidMeSH, HMDB
alpha-MethylaminoisobutyrateMeSH, HMDB
alpha-(methylamino)IsobutyrateMeSH, Generator, HMDB
a-(Methylamino)isobutyrateGenerator, HMDB
a-(Methylamino)isobutyric acidGenerator, HMDB
Α-(methylamino)isobutyrateGenerator, HMDB
Α-(methylamino)isobutyric acidGenerator, HMDB
N-Methyl-a-aminoisobutyric acidGenerator
N-Methyl-α-aminoisobutyrateGenerator, HMDB
N-Methyl-α-aminoisobutyric acidGenerator, HMDB
Chemical FormulaC5H11NO2
Average Molecular Weight117.1463
Monoisotopic Molecular Weight117.078978601
IUPAC Name2-methyl-2-(methylamino)propanoic acid
Traditional Name2-(methylamino)isobutyric acid
CAS Registry Number2566-34-9
SMILES
CNC(C)(C)C(O)=O
InChI Identifier
InChI=1S/C5H11NO2/c1-5(2,6-3)4(7)8/h6H,1-3H3,(H,7,8)
InChI KeyDLAMVQGYEVKIRE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility136 g/LALOGPS
logP10(-2.1) g/LALOGPS
logP10(-2.2) g/LChemAxon
logS10(0.06) g/LALOGPS
pKa (Strongest Acidic)2.23ChemAxon
pKa (Strongest Basic)10.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.99 m³·mol⁻¹ChemAxon
Polarizability12.27 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]+125.94331661259
DarkChem[M-H]-121.93431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Methyl-a-aminoisobutyric acidCNC(C)(C)C(O)=O1814.9Standard polar33892256
N-Methyl-a-aminoisobutyric acidCNC(C)(C)C(O)=O944.0Standard non polar33892256
N-Methyl-a-aminoisobutyric acidCNC(C)(C)C(O)=O983.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Methyl-a-aminoisobutyric acid,1TMS,isomer #1CNC(C)(C)C(=O)O[Si](C)(C)C993.6Semi standard non polar33892256
N-Methyl-a-aminoisobutyric acid,1TMS,isomer #2CN(C(C)(C)C(=O)O)[Si](C)(C)C1167.0Semi standard non polar33892256
N-Methyl-a-aminoisobutyric acid,2TMS,isomer #1CN(C(C)(C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1194.8Semi standard non polar33892256
N-Methyl-a-aminoisobutyric acid,2TMS,isomer #1CN(C(C)(C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1166.8Standard non polar33892256
N-Methyl-a-aminoisobutyric acid,2TMS,isomer #1CN(C(C)(C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1211.6Standard polar33892256
N-Methyl-a-aminoisobutyric acid,1TBDMS,isomer #1CNC(C)(C)C(=O)O[Si](C)(C)C(C)(C)C1245.6Semi standard non polar33892256
N-Methyl-a-aminoisobutyric acid,1TBDMS,isomer #2CN(C(C)(C)C(=O)O)[Si](C)(C)C(C)(C)C1411.8Semi standard non polar33892256
N-Methyl-a-aminoisobutyric acid,2TBDMS,isomer #1CN(C(C)(C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1663.1Semi standard non polar33892256
N-Methyl-a-aminoisobutyric acid,2TBDMS,isomer #1CN(C(C)(C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1657.4Standard non polar33892256
N-Methyl-a-aminoisobutyric acid,2TBDMS,isomer #1CN(C(C)(C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1509.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Methyl-a-aminoisobutyric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9000000000-5fba0a2d2108e729bca62017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Methyl-a-aminoisobutyric acid GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9800000000-0eb03e70c976ad55c75a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Methyl-a-aminoisobutyric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-014i-0900000000-aa808db31e15719554e32012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-00di-9000000000-bab3ca61968c0f1655d72012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-00di-9100000000-a3b4db0612a98cb07c6e2012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid 10V, Positive-QTOFsplash10-00di-9200000000-08316a6d4782c3dd334a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid 20V, Positive-QTOFsplash10-00di-9000000000-f3b337147d8b8df303682017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid 40V, Positive-QTOFsplash10-05fu-9000000000-9b793144ee28f81da77e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid 10V, Negative-QTOFsplash10-014i-1900000000-22f34917de1c91b5309b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid 20V, Negative-QTOFsplash10-014i-6900000000-3e1e8105c25d0baac4f42017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid 40V, Negative-QTOFsplash10-05fu-9000000000-99c906e2c488e0c37b442017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid 10V, Negative-QTOFsplash10-014i-0900000000-92555825d99a6154218c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid 20V, Negative-QTOFsplash10-014i-4900000000-947b8ec1a2963201eda32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid 40V, Negative-QTOFsplash10-0006-9000000000-d948d5d95ae14e701f572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid 10V, Positive-QTOFsplash10-00di-9100000000-62cb4ab58b19ca6396802021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid 20V, Positive-QTOFsplash10-00di-9000000000-c286143495e50fa10a8d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-a-aminoisobutyric acid 40V, Positive-QTOFsplash10-0ab9-9000000000-71a5ffa96c5ec81f74682021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart 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 IDDB08832
Phenol Explorer Compound IDNot Available
FooDB IDFDB022865
KNApSAcK IDNot Available
Chemspider ID68242
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6508
PubChem Compound6951124
PDB IDNot Available
ChEBI ID134261
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Thongsong B, Subramanian RK, Ganapathy V, Prasad PD: Inhibition of amino acid transport system a by interleukin-1beta in trophoblasts. J Soc Gynecol Investig. 2005 Oct;12(7):495-503. [PubMed:16202926 ]