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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-03-23 05:23:51 UTC

Update Date

2023-02-21 17:31:03 UTC

HMDB ID

HMDB0062660

Secondary Accession Numbers

HMDB62660

Metabolite Identification

Common Name

N-methyl-L-glutamic Acid

Description

N-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 17-JUL-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-18         0                                  
HETATM    1  C   UNK     0      11.288  -3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.287  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.954  -3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.621  -3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.621  -4.977   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       9.955  -2.667   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       3.286  -3.437   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.620  -1.127   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       9.955  -5.747   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.287  -5.747   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       7.287  -4.207   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6    7   12                                             
CONECT    5    3    8    9                                                  
CONECT    6    4   10   11                                                  
CONECT    7    1    4                                                       
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    4                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-(Methylamino)pentanedioic acid	ChEBI
N-Methylglutamic acid	ChEBI
(2S)-2-(Methylamino)pentanedioate	Generator
N-Methylglutamate	Generator
N-Methyl-L-glutamate	Generator
N-Methyl-D-glutamate	HMDB

Chemical Formula

C₆H₁₁NO₄

Average Molecular Weight

161.1558

Monoisotopic Molecular Weight

161.068807845

IUPAC Name

(2S)-2-(methylamino)pentanedioic acid

Traditional Name

N-methyl-L-glutamic acid

CAS Registry Number

35989-16-3

SMILES

[H][C@@](CCC(O)=O)(NC)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 Key

XLBVNMSMFQMKEY-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic 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 Framework

Aliphatic acyclic compounds

External Descriptors

N-methyl-L-alpha-amino acid (CHEBI:16440 )
L-glutamic acid derivative (CHEBI:16440 )

Ontology

Not Available

Urine (PMID: 27510537)
Feces (PMID: 27543620)

Source

Exogenous

Exogenous (HMDB: HMDB0062660)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	32.1 g/l	ALOGPS
LogP	-2.56	ALOGPS

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Baker	133.715	30932474
[M-H]-	Not Available	130.1	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001948
[M+H]+	Not Available	132.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001948

Predicted Molecular Properties

Property	Value	Source
logP	-2.6	ALOGPS
logP	-3	ChemAxon
logS	-0.7	ALOGPS
pKa (Strongest Acidic)	1.58	ChemAxon
pKa (Strongest Basic)	10.62	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	36.06 m³·mol⁻¹	ChemAxon
Polarizability	15.24 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.02	31661259
DarkChem	[M-H]-	131.695	31661259
DeepCCS	[M+H]+	130.8	30932474
DeepCCS	[M-H]-	126.973	30932474
DeepCCS	[M-2H]-	164.539	30932474
DeepCCS	[M+Na]+	140.078	30932474
AllCCS	[M+H]+	137.7	32859911
AllCCS	[M+H-H2O]+	133.8	32859911
AllCCS	[M+NH4]+	141.4	32859911
AllCCS	[M+Na]+	142.4	32859911
AllCCS	[M-H]-	131.6	32859911
AllCCS	[M+Na-2H]-	133.5	32859911
AllCCS	[M+HCOO]-	135.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.16 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2415 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.83 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-methyl-L-glutamic Acid	CN[C@@H](CCC(O)=O)C(O)=O	2481.5	Standard polar	33892256
N-methyl-L-glutamic Acid	CN[C@@H](CCC(O)=O)C(O)=O	1325.7	Standard non polar	33892256
N-methyl-L-glutamic Acid	CN[C@@H](CCC(O)=O)C(O)=O	1513.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-methyl-L-glutamic Acid,1TMS,isomer #1	CN[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O	1514.4	Semi standard non polar	33892256
N-methyl-L-glutamic Acid,1TMS,isomer #2	CN[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C	1483.2	Semi standard non polar	33892256
N-methyl-L-glutamic Acid,1TMS,isomer #3	CN([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C	1605.5	Semi standard non polar	33892256
N-methyl-L-glutamic Acid,2TMS,isomer #1	CN[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1526.1	Semi standard non polar	33892256
N-methyl-L-glutamic Acid,2TMS,isomer #2	CN([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1658.6	Semi standard non polar	33892256
N-methyl-L-glutamic Acid,2TMS,isomer #3	CN([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1639.6	Semi standard non polar	33892256
N-methyl-L-glutamic Acid,3TMS,isomer #1	CN([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1654.3	Semi standard non polar	33892256
N-methyl-L-glutamic Acid,3TMS,isomer #1	CN([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1659.1	Standard non polar	33892256
N-methyl-L-glutamic Acid,3TMS,isomer #1	CN([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1754.6	Standard polar	33892256
N-methyl-L-glutamic Acid,1TBDMS,isomer #1	CN[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1764.4	Semi standard non polar	33892256
N-methyl-L-glutamic Acid,1TBDMS,isomer #2	CN[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1737.0	Semi standard non polar	33892256
N-methyl-L-glutamic Acid,1TBDMS,isomer #3	CN([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	1846.1	Semi standard non polar	33892256
N-methyl-L-glutamic Acid,2TBDMS,isomer #1	CN[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1987.1	Semi standard non polar	33892256
N-methyl-L-glutamic Acid,2TBDMS,isomer #2	CN([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2138.7	Semi standard non polar	33892256
N-methyl-L-glutamic Acid,2TBDMS,isomer #3	CN([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2121.5	Semi standard non polar	33892256
N-methyl-L-glutamic Acid,3TBDMS,isomer #1	CN([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)C	2338.3	Semi standard non polar	33892256
N-methyl-L-glutamic Acid,3TBDMS,isomer #1	CN([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)C	2297.3	Standard non polar	33892256
N-methyl-L-glutamic Acid,3TBDMS,isomer #1	CN([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)C	2173.5	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
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

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C01046

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-Methyl-L-glutamic_acid

METLIN ID

Not Available

PubChem Compound

439377

PDB ID

EME

ChEBI ID

16440

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for N-methyl-L-glutamic Acid (HMDB0062660)

MOL for HMDB0062660 (N-methyl-L-glutamic Acid)

3D MOL for HMDB0062660 (N-methyl-L-glutamic Acid)

3D SDF for HMDB0062660 (N-methyl-L-glutamic Acid)

3D-SDF for HMDB0062660 (N-methyl-L-glutamic Acid)

PDB for HMDB0062660 (N-methyl-L-glutamic Acid)

3D PDB for HMDB0062660 (N-methyl-L-glutamic Acid)

SMILES for HMDB0062660 (N-methyl-L-glutamic Acid)

INCHI for HMDB0062660 (N-methyl-L-glutamic Acid)

Structure for HMDB0062660 (N-methyl-L-glutamic Acid)

3D Structure for HMDB0062660 (N-methyl-L-glutamic Acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized