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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2017-03-23 05:23:51 UTC
Update Date2022-03-07 03:17:57 UTC
HMDB IDHMDB0062660
Secondary Accession Numbers
  • HMDB62660
Metabolite Identification
Common NameN-methyl-L-glutamic Acid
DescriptionN-methyl-L-glutamic Acid, also known as N-Methylglutamate or (2S)-2-(methylamino)Pentanedioic acid, is classified as a glutamic acid or a Glutamic acid derivative. Glutamic acids are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-methyl-L-glutamic Acid is considered to be soluble (in water) and acidic
Structure
Data?1563866343
Synonyms
ValueSource
(2S)-2-(Methylamino)pentanedioic acidChEBI
N-Methylglutamic acidChEBI
(2S)-2-(Methylamino)pentanedioateGenerator
N-MethylglutamateGenerator
N-Methyl-L-glutamateGenerator
N-Methyl-D-glutamateHMDB
Chemical FormulaC6H11NO4
Average Molecular Weight161.1558
Monoisotopic Molecular Weight161.068807845
IUPAC Name(2S)-2-(methylamino)pentanedioic acid
Traditional NameN-methyl-L-glutamic acid
CAS Registry Number35989-16-3
SMILES
CN[C@@H](CCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H11NO4/c1-7-4(6(10)11)2-3-5(8)9/h4,7H,2-3H2,1H3,(H,8,9)(H,10,11)/t4-/m0/s1
InChI KeyXLBVNMSMFQMKEY-BYPYZUCNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid 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 ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Amino fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Secondary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility32.1 g/lALOGPS
LogP-2.56ALOGPS
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Baker133.71530932474
[M-H]-Not Available130.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00001948
[M+H]+Not Available132.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00001948
Predicted Molecular Properties
PropertyValueSource
logP-2.6ALOGPS
logP-3ChemAxon
logS-0.7ALOGPS
pKa (Strongest Acidic)1.58ChemAxon
pKa (Strongest Basic)10.62ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.06 m³·mol⁻¹ChemAxon
Polarizability15.24 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]+136.0231661259
DarkChem[M-H]-131.69531661259
DeepCCS[M+H]+130.830932474
DeepCCS[M-H]-126.97330932474
DeepCCS[M-2H]-164.53930932474
DeepCCS[M+Na]+140.07830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-methyl-L-glutamic AcidCN[C@@H](CCC(O)=O)C(O)=O2481.5Standard polar33892256
N-methyl-L-glutamic AcidCN[C@@H](CCC(O)=O)C(O)=O1325.7Standard non polar33892256
N-methyl-L-glutamic AcidCN[C@@H](CCC(O)=O)C(O)=O1513.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-methyl-L-glutamic Acid,1TMS,isomer #1CN[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O1514.4Semi standard non polar33892256
N-methyl-L-glutamic Acid,1TMS,isomer #2CN[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C1483.2Semi standard non polar33892256
N-methyl-L-glutamic Acid,1TMS,isomer #3CN([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C1605.5Semi standard non polar33892256
N-methyl-L-glutamic Acid,2TMS,isomer #1CN[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1526.1Semi standard non polar33892256
N-methyl-L-glutamic Acid,2TMS,isomer #2CN([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C1658.6Semi standard non polar33892256
N-methyl-L-glutamic Acid,2TMS,isomer #3CN([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C1639.6Semi standard non polar33892256
N-methyl-L-glutamic Acid,3TMS,isomer #1CN([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1654.3Semi standard non polar33892256
N-methyl-L-glutamic Acid,3TMS,isomer #1CN([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1659.1Standard non polar33892256
N-methyl-L-glutamic Acid,3TMS,isomer #1CN([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1754.6Standard polar33892256
N-methyl-L-glutamic Acid,1TBDMS,isomer #1CN[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1764.4Semi standard non polar33892256
N-methyl-L-glutamic Acid,1TBDMS,isomer #2CN[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C1737.0Semi standard non polar33892256
N-methyl-L-glutamic Acid,1TBDMS,isomer #3CN([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C1846.1Semi standard non polar33892256
N-methyl-L-glutamic Acid,2TBDMS,isomer #1CN[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1987.1Semi standard non polar33892256
N-methyl-L-glutamic Acid,2TBDMS,isomer #2CN([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2138.7Semi standard non polar33892256
N-methyl-L-glutamic Acid,2TBDMS,isomer #3CN([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2121.5Semi standard non polar33892256
N-methyl-L-glutamic Acid,3TBDMS,isomer #1CN([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2338.3Semi standard non polar33892256
N-methyl-L-glutamic Acid,3TBDMS,isomer #1CN([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2297.3Standard non polar33892256
N-methyl-L-glutamic Acid,3TBDMS,isomer #1CN([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2173.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - N-methyl-L-glutamic Acid GC-MS (2 TMS)splash10-0002-9200000000-0c4b235999d1960527882014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-methyl-L-glutamic Acid GC-MS (3 TMS)splash10-01ot-9650000000-a98eccbc47ede44d59d22014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-methyl-L-glutamic Acid GC-EI-TOF (Non-derivatized)splash10-0002-8950000000-b1c9c156a92482c687352017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-methyl-L-glutamic Acid GC-EI-TOF (Non-derivatized)splash10-0udi-2490000000-5ddd6b15534301c95e082017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-methyl-L-glutamic Acid GC-EI-TOF (Non-derivatized)splash10-0002-9000000000-c907e2adba5812c4e3c92017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-methyl-L-glutamic Acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-871bf7957f4dcb17943d2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-methyl-L-glutamic Acid GC-MS (2 TMS) - 70eV, Positivesplash10-00du-9410000000-0b43a69921d90fa675942017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-methyl-L-glutamic 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-L-glutamic Acid LC-ESI-QQ , negative-QTOFsplash10-03di-0900000000-7b507ba28cfa8e63b0d02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid LC-ESI-QQ , negative-QTOFsplash10-00kf-0900000000-4c41bb8d74f7aa1402562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid LC-ESI-QQ , negative-QTOFsplash10-014i-1900000000-51948d38ac6cd62f280a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid LC-ESI-QQ , negative-QTOFsplash10-066r-9700000000-3a6a7edac0b0847066f12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid LC-ESI-QQ , negative-QTOFsplash10-0ab9-9000000000-581b43d5f7cfdc468c7b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid , negative-QTOFsplash10-00kf-0900000000-732f1e6be747e1b6f2de2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid 35V, Negative-QTOFsplash10-00kf-0900000000-8954c58bdd0379f241122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid 20V, Negative-QTOFsplash10-066r-5900000000-7cf329dad1e06171cb4d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid 10V, Negative-QTOFsplash10-00kf-0900000000-c37a5f22b912f98feabb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid LC-ESI-QQ , positive-QTOFsplash10-03di-0900000000-000b100afdb47d44de152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid LC-ESI-QQ , positive-QTOFsplash10-0002-9800000000-f5492c9a9081f3c562022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid LC-ESI-QQ , positive-QTOFsplash10-0002-9100000000-bd08fe273639d913c18e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid LC-ESI-QQ , positive-QTOFsplash10-00dj-9100000000-1ff447da2161f69251b72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid LC-ESI-QQ , positive-QTOFsplash10-00di-9100000000-e5d8b8d3e6a1a207c4542017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid , positive-QTOFsplash10-0295-4900000000-15244bdad069dd71de4b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid 20V, Positive-QTOFsplash10-0002-9000000000-7373351234612b0fad7b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid 40V, Positive-QTOFsplash10-006x-9000000000-19ecec1def5e2f2aeeff2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid 10V, Positive-QTOFsplash10-00kb-8900000000-4c65b49ca0f5fa819c892021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid 35V, Positive-QTOFsplash10-0295-4900000000-13d8487e1c605a46a5fe2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid 20V, Positive-QTOFsplash10-0002-9000000000-c7d83ccfc3fc1720dd342021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid 40V, Positive-QTOFsplash10-006x-9000000000-69bae6e8a352e4399b5d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-methyl-L-glutamic Acid 10V, Positive-QTOFsplash10-00kb-6900000000-4785a7f145762fccb3a72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-methyl-L-glutamic Acid 10V, Negative-QTOFsplash10-03di-0900000000-484ef250f8d9e2e9b2a72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-methyl-L-glutamic Acid 20V, Negative-QTOFsplash10-03xu-3900000000-c8ee4dd07183089986782017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-methyl-L-glutamic Acid 40V, Negative-QTOFsplash10-0abm-9300000000-da4d09190f7dd28a11ca2017-10-06Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01046
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Methyl-L-glutamic_acid
METLIN IDNot Available
PubChem Compound439377
PDB IDEME
ChEBI ID16440
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 ReferencesNot Available