MiMeDB: Showing metabocard for N6-Stearoyl-L-lysine (MMDBc0057181)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-11-09 19:26:20 UTC

Update Date

2025-10-07 16:09:55 UTC

Metabolite ID

MMDBc0057181

Metabolite Identification

Common Name

N6-Stearoyl-L-lysine

Description

N6-Stearoyl-L-lysine is a synthetic muramyl dipeptide derivative belonging to the class of immunomodulatory compounds. Its chemical structure features a stearoyl group attached to the nitrogen at the sixth position of L-lysine, contributing to its lipophilicity and biological activity. This compound, also known as MDP-Lys or romurtide, functions as a macrophage activator, enhancing the immune response by stimulating cells of the monocyte-macrophage lineage (PMID:11061343 ). It has been shown to induce the production of various cytokines, including interleukin-1 (IL-1) and tumor necrosis factor (TNF), which are critical in inflammatory pathways (PMID:10688489 ). Additionally, repeated subcutaneous administration of MDP-Lys has been observed to increase the counts of peripheral neutrophils and monocytes, indicating its role in modulating immune cell populations (PMID:2049113 ). Furthermore, it has been reported to augment the production of complement components, such as C1q, which are essential for the opsonization and clearance of pathogens (PMID:2340001 ). Overall, N6-stearoyl-L-lysine exemplifies the intersection of synthetic chemistry and immunology, with significant implications for therapeutic applications.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₂₄H₄₈N₂O₃

Average Mass

412.659

Monoisotopic Mass

412.366493414

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

Not Available

InChI Key

PQOQDGZTLPYXJD-QFIPXVFZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Not Available

Spectra

Not Available

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	251.9
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	61.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	608.5
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	652.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	743.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	263.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	2859.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	516.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (retained)	2025-10-24	261.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	654.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	186.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	174.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	236.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (retained)	2025-10-24	9.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	296.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	561.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	460.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1744.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	1822.5

Retention Indices

Not Available

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

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

104260

PDB ID

Not Available

ChEBI ID

Not Available

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 N6-Stearoyl-L-lysine (MMDBc0057181)

MOL for #<Metabolite:0x00007f2e383ca100>

3D MOL for #<Metabolite:0x00007f2e383ca100>

3D SDF for #<Metabolite:0x00007f2e383ca100>

3D-SDF for #<Metabolite:0x00007f2e383ca100>

PDB for #<Metabolite:0x00007f2e383ca100>

3D PDB for #<Metabolite:0x00007f2e383ca100>

SMILES for #<Metabolite:0x00007f2e383ca100>

INCHI for #<Metabolite:0x00007f2e383ca100>

Structure for #<Metabolite:0x00007f2e383ca100>

3D Structure for #<Metabolite:0x00007f2e383ca100>