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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2014-04-16 20:46:51 UTC
Update Date2023-02-21 17:30:26 UTC
HMDB IDHMDB0061716
Secondary Accession Numbers
  • HMDB61716
Metabolite Identification
Common NameN-methylvaline
DescriptionN-methylvaline, also known as maval, belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-methylvaline is a very strong basic compound (based on its pKa). An optically active form of N-methylvaline having L-configuration.
Structure
Data?1677000626
Synonyms
ValueSource
(2S)-3-Methyl-2-(methylamino)butanoic acidChEBI
MaValChEBI
MethylvalineChEBI
(2S)-3-Methyl-2-(methylamino)butanoateGenerator
MeValMeSH
3-Methyl-2-(methylamino)butanoic acidMeSH
N-MethylvalineChEBI
Chemical FormulaC6H13NO2
Average Molecular Weight131.1729
Monoisotopic Molecular Weight131.094628665
IUPAC Name(2S)-3-methyl-2-(methylamino)butanoic acid
Traditional Name(2S)-3-methyl-2-(methylamino)butanoic acid
CAS Registry NumberNot Available
SMILES
CN[C@@H](C(C)C)C(O)=O
InChI Identifier
InChI=1S/C6H13NO2/c1-4(2)5(7-3)6(8)9/h4-5,7H,1-3H3,(H,8,9)/t5-/m0/s1
InChI KeyAKCRVYNORCOYQT-YFKPBYRVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentValine and derivatives
Alternative Parents
Substituents
  • Valine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Secondary aliphatic amine
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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 Solubility119 g/LALOGPS
logP-1.8ALOGPS
logP-1.7ChemAxon
logS-0.04ALOGPS
pKa (Strongest Acidic)2.35ChemAxon
pKa (Strongest Basic)10.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.27 m³·mol⁻¹ChemAxon
Polarizability14.21 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]+129.05231661259
DarkChem[M-H]-125.79531661259
DeepCCS[M+H]+128.82530932474
DeepCCS[M-H]-124.99630932474
DeepCCS[M-2H]-162.11430932474
DeepCCS[M+Na]+137.52430932474
AllCCS[M+H]+132.432859911
AllCCS[M+H-H2O]+128.332859911
AllCCS[M+NH4]+136.132859911
AllCCS[M+Na]+137.232859911
AllCCS[M-H]-129.232859911
AllCCS[M+Na-2H]-132.132859911
AllCCS[M+HCOO]-135.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-methylvalineCN[C@@H](C(C)C)C(O)=O1834.3Standard polar33892256
N-methylvalineCN[C@@H](C(C)C)C(O)=O1115.9Standard non polar33892256
N-methylvalineCN[C@@H](C(C)C)C(O)=O1083.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-methylvaline,1TMS,isomer #1CN[C@H](C(=O)O[Si](C)(C)C)C(C)C1092.2Semi standard non polar33892256
N-methylvaline,1TMS,isomer #2CC(C)[C@@H](C(=O)O)N(C)[Si](C)(C)C1232.4Semi standard non polar33892256
N-methylvaline,2TMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C)[Si](C)(C)C1263.9Semi standard non polar33892256
N-methylvaline,2TMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C)[Si](C)(C)C1216.0Standard non polar33892256
N-methylvaline,2TMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C)[Si](C)(C)C1278.7Standard polar33892256
N-methylvaline,1TBDMS,isomer #1CN[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)C1318.7Semi standard non polar33892256
N-methylvaline,1TBDMS,isomer #2CC(C)[C@@H](C(=O)O)N(C)[Si](C)(C)C(C)(C)C1463.8Semi standard non polar33892256
N-methylvaline,2TBDMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C1723.4Semi standard non polar33892256
N-methylvaline,2TBDMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C1678.7Standard non polar33892256
N-methylvaline,2TBDMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C1604.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-methylvaline GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9000000000-2e57b58ca4ffbac540162017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-methylvaline GC-MS (1 TMS) - 70eV, Positivesplash10-000f-9100000000-9c606f603835e37934502017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-methylvaline 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 - N-methylvaline 10V, Positive-QTOFsplash10-01qi-4900000000-1b1d110012b65191b57c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-methylvaline 20V, Positive-QTOFsplash10-000i-9300000000-ec3dce11c5e5d8e97e842017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-methylvaline 40V, Positive-QTOFsplash10-05fr-9000000000-95d5856ba1ad371112772017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-methylvaline 10V, Negative-QTOFsplash10-001r-4900000000-fbf697d8663079eed26f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-methylvaline 20V, Negative-QTOFsplash10-01qi-6900000000-282ec83fd2cc5d1dcf2f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-methylvaline 40V, Negative-QTOFsplash10-0083-9100000000-89b2da916a1d7a5f7ce82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-methylvaline 10V, Positive-QTOFsplash10-000i-9100000000-f4dd10fa5b3ccd6c34472021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-methylvaline 20V, Positive-QTOFsplash10-000i-9000000000-d28054a44ad67728c56b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-methylvaline 40V, Positive-QTOFsplash10-0006-9000000000-e247e1fc6423397264142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-methylvaline 10V, Negative-QTOFsplash10-001i-0900000000-06466c9190b13de8e4be2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-methylvaline 20V, Negative-QTOFsplash10-001i-0900000000-1fad5f5fc44cfc94ec812021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-methylvaline 40V, Negative-QTOFsplash10-0006-9100000000-140dc49f5377093c54a72021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD0-1059
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound444080
PDB IDMVA
ChEBI ID44212
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. Bader M, Lewalter J, Angerer J: Analysis of N-alkylated amino acids in human hemoglobin: evidence for elevated N-methylvaline levels in smokers. Int Arch Occup Environ Health. 1995;67(4):237-42. [PubMed:7591184 ]