MiMeDB: Showing metabocard for Norleucine (MMDBc0033204)

Animal

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:38:57 UTC

Update Date

2025-01-15 19:19:49 UTC

Metabolite ID

MMDBc0033204

Metabolite Identification

Common Name

Norleucine

Description

L-Norleucine, also known as L-aminohexanoate or caprine, 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. Thus, L-norleucine is considered to be a fatty acid lipid molecule. An unnatural amino acid that is used experimentally to study protein structure and function. L-Norleucine is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. L-Norleucine exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, L-Norleucine has been detected, but not quantified in cow milk. This could make L-norleucine a potential biomarker for the consumption of these foods. It binds reversibly to the kringle domain of plasminogen and blocks the binding of plasminogen to fibrin and its activation to plasmin.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₆H₁₃NO₂

Average Mass

131.1729

Monoisotopic Mass

131.0946287

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

327-57-1

SMILES

Not Available

InChI Identifier

InChI=1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1

InChI Key

LRQKBLKVPFOOQJ-YFKPBYRVSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

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	412.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	320.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	178.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	281.6
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	289.2
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	320.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	765.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	613.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (retained)	2025-10-24	497.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	198.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	383.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	187.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	84.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	258.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	623.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	81.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	234.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	815.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	708.3

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Norleucine_TMS_1	CCCC[C@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1977.92
Gas Chromatography	Norleucine_TMS_2	CCCC[C@H](N[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1892.82
Gas Chromatography	Norleucine_TMS_3	CCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2287.83
Gas Chromatography	Norleucine_TMS_4	CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2095.97
Gas Chromatography	Norleucine_TMS_5	CCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1989.43
Gas Chromatography	Norleucine_TMS_1	CCCC[C@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2229.85
Gas Chromatography	Norleucine_TMS_2	CCCC[C@H](N[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2004.09
Gas Chromatography	Norleucine_TMS_3	CCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2234.01
Gas Chromatography	Norleucine_TMS_4	CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2385.56
Gas Chromatography	Norleucine_TMS_5	CCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2616.75

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Platelet
Testis
Urine

Tissue Locations

Platelet
Testis

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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown
Bacteria/Eubacteria	Proteobacteria	1	Human

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	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.0065	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Platelet	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597
Human Blood	Detected but not Quantified						HMDB

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

Not Available

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 Norleucine (MMDBc0033204)

MOL for #<Metabolite:0x00007f9a9db8a4b8>

3D MOL for #<Metabolite:0x00007f9a9db8a4b8>

3D SDF for #<Metabolite:0x00007f9a9db8a4b8>

3D-SDF for #<Metabolite:0x00007f9a9db8a4b8>

PDB for #<Metabolite:0x00007f9a9db8a4b8>

3D PDB for #<Metabolite:0x00007f9a9db8a4b8>

SMILES for #<Metabolite:0x00007f9a9db8a4b8>

INCHI for #<Metabolite:0x00007f9a9db8a4b8>

Structure for #<Metabolite:0x00007f9a9db8a4b8>

3D Structure for #<Metabolite:0x00007f9a9db8a4b8>