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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:02:12 UTC
Update Date2021-09-14 15:46:17 UTC
HMDB IDHMDB0028713
Secondary Accession Numbers
  • HMDB28713
Metabolite Identification
Common NameArginylleucine
DescriptionArginylleucine, also known as RL or L-arg-L-leu, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Arginylleucine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make arginylleucine a potential biomarker for the consumption of these foods. Arginylleucine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Arginylleucine.
Structure
Data?1582753330
Synonyms
ValueSource
Arginyl-leucineChEBI
L-Arg-L-leuChEBI
RLChEBI
Arg-leuHMDB
Arginine leucine dipeptideHMDB
Arginine-leucine dipeptideHMDB
L-Arginyl-L-leucineHMDB
N-ArginylleucineHMDB
N-L-Arginyl-L-leucineHMDB
R-L DipeptideHMDB
RL DipeptideHMDB
ArginylleucineChEBI
Chemical FormulaC12H25N5O3
Average Molecular Weight287.364
Monoisotopic Molecular Weight287.195739685
IUPAC Name(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-4-methylpentanoic acid
Traditional Name(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-4-methylpentanoic acid
CAS Registry Number1188-24-5
SMILES
CC(C)C[C@H](NC(=O)[C@@H](N)CCCNC(N)=N)C(O)=O
InChI Identifier
InChI=1S/C12H25N5O3/c1-7(2)6-9(11(19)20)17-10(18)8(13)4-3-5-16-12(14)15/h7-9H,3-6,13H2,1-2H3,(H,17,18)(H,19,20)(H4,14,15,16)/t8-,9-/m0/s1
InChI KeyWYBVBIHNJWOLCJ-IUCAKERBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Leucine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Fatty amide
  • N-acyl-amine
  • Guanidine
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Amino acid
  • Carboxamide group
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.43Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. 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 IDFDB111770
KNApSAcK IDNot Available
Chemspider ID5360693
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6992563
PDB IDNot Available
ChEBI ID73815
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 References
  1. Mironova NL, Pyshnyi DV, Ivanova EM, Zenkova MA, Gross HJ, Vlassov VV: Covalently attached oligodeoxyribonucleotides induce RNase activity of a short peptide and modulate its base specificity. Nucleic Acids Res. 2004 Mar 26;32(6):1928-36. Print 2004. [PubMed:15047859 ]
  2. Schug KA, Lindner W, Lemr K: Isomeric discrimination of arginine-containing dipeptides using electrospray ionization-ion trap mass spectrometry and the kinetic method. J Am Soc Mass Spectrom. 2004 Jun;15(6):840-7. [PubMed:15144973 ]
  3. Morgan WT, Riehm JP: The isolation and some enzymatic properties of des-arginylleucine-lysozyme. Biochem Biophys Res Commun. 1968 Jan 11;30(1):50-6. [PubMed:5688915 ]