MiMeDB: Showing metabocard for N(5)-methyl-L-glutamine (MMDBc0054598)

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:20:18 UTC

Update Date

2025-10-07 16:08:35 UTC

Metabolite ID

MMDBc0054598

Metabolite Identification

Common Name

N(5)-methyl-L-glutamine

Description

N(5)-methyl-L-glutamine is a non-proteinogenic amino acid belonging to the class of amino acid derivatives. There is limited literature available on this metabolite, indicating a need for further research to fully understand its biological significance and potential applications.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
gamma-Methylglutamine	ChEBI
N(delta)-Methylglutamine	ChEBI
N-Methylglutamine	ChEBI
N5-Methyl-L-glutamine	ChEBI
g-Methylglutamine	Generator
Γ-methylglutamine	Generator
N(Δ)-methylglutamine	Generator
N5-METHYLGLUTAMINE	ChEBI
(2S)-2-Amino-4-(methyl-C-hydroxycarbonimidoyl)butanoate	Generator

Molecular Formula

C₆H₁₂N₂O₃

Average Mass

160.1711

Monoisotopic Mass

160.08479226

IUPAC Name

(2S)-2-amino-4-(methylcarbamoyl)butanoic acid

Traditional Name

N5-methylglutamine

CAS Registry Number

Not Available

SMILES

CNC(=O)CC[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C6H12N2O3/c1-8-5(9)3-2-4(7)6(10)11/h4H,2-3,7H2,1H3,(H,8,9)(H,10,11)/t4-/m0/s1

InChI Key

ONXPDKGXOOORHB-BYPYZUCNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine 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

Glutamine and derivatives

Alternative Parents

Substituents

Glutamine or derivatives
Alpha-amino acid
L-alpha-amino acid
Fatty amide
N-acyl-amine
Fatty acid
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Organic oxide
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N(5)-alkyl-L-glutamine (CHEBI:17592 )
N-methyl-amino acid (CHEBI:17592 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	56.5 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-3.8	ChemAxon
logS	-0.45	ALOGPS
pKa (Strongest Acidic)	2.26	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	38.01 m³·mol⁻¹	ChemAxon
Polarizability	15.86 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0543-9200000000-6cdf49cd0e4b15fd20d5	2017-08-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02tl-3900000000-e3200e4c3350a7e09e88	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-9700000000-7b47e3d9b43649b4f885	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-6d55a5030a08a37908ec	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1900000000-c50b14fcac5529a3fccd	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a5c-3900000000-29f6be27853599a05fb2	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fu-9000000000-4d1e0288806422103c38	2017-07-26	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	481.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	350.2
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	40.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	230.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	267.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	265.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	453.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	795.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	620.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	152.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	482.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	166.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	55.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	351.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	679.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	48.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	207.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	668.1
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	554.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_1	CNC(=O)CC[C@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1947.76
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_2	CNC(=O)CC[C@H](N[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1838.47
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_3	CN(C(=O)CC[C@H](N)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2100.12
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_4	CNC(=O)CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1921.89
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_5	CN(C(=O)CC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1909.35
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_6	CN(C(=O)CC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2049.68
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_7	CNC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1920.37
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_8	CN(C(=O)CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1693.21
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_9	CNC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2535.83
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_10	CN(C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1640.13
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_11	CN(C(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1681.78
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_1	CNC(=O)CC[C@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2308.11
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_2	CNC(=O)CC[C@H](N[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	1861.18
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_3	CN(C(=O)CC[C@H](N)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	1624.87
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_4	CNC(=O)CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2100.13
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_5	CN(C(=O)CC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2473.92
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_6	CN(C(=O)CC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2315.09
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_7	CNC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2077.54
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_8	CN(C(=O)CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2355.11
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_9	CNC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2654.65
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_10	CN(C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1991.39
Gas Chromatography	N(5)-methyl-L-glutamine_TMS_11	CN(C(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1982.29

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human feces
Bacteria/Eubacteria	Proteobacteria	1	Human feces

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

DB03473

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C03153

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439925

PDB ID

Not Available

ChEBI ID

17592

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for N(5)-methyl-L-glutamine (MMDBc0054598)

MOL for #<Metabolite:0x00007fc977efaa40>

3D MOL for #<Metabolite:0x00007fc977efaa40>

3D SDF for #<Metabolite:0x00007fc977efaa40>

3D-SDF for #<Metabolite:0x00007fc977efaa40>

PDB for #<Metabolite:0x00007fc977efaa40>

3D PDB for #<Metabolite:0x00007fc977efaa40>

SMILES for #<Metabolite:0x00007fc977efaa40>

INCHI for #<Metabolite:0x00007fc977efaa40>

Structure for #<Metabolite:0x00007fc977efaa40>

3D Structure for #<Metabolite:0x00007fc977efaa40>