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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:02:12 UTC
Update Date2021-09-14 15:45:02 UTC
HMDB IDHMDB0028712
Secondary Accession Numbers
  • HMDB28712
Metabolite Identification
Common NameArginylisoleucine
DescriptionArginylisoleucine, also known as RI or L-arg-L-ile, 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. Arginylisoleucine 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 arginylisoleucine a potential biomarker for the consumption of these foods. Arginylisoleucine 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 very few articles have been published on Arginylisoleucine.
Structure
Data?1582753329
Synonyms
ValueSource
Arginyl-isoleucineChEBI
L-Arg-L-ileChEBI
RIChEBI
Arg-ileHMDB
Arginine isoleucine dipeptideHMDB
Arginine-isoleucine dipeptideHMDB
L-Arginyl-L-isoleucineHMDB
N-ArginylisoleucineHMDB
N-L-Arginyl-L-isoleucineHMDB
R-I dipeptideHMDB
RI dipeptideHMDB
ArginylisoleucineChEBI
Chemical FormulaC12H25N5O3
Average Molecular Weight287.364
Monoisotopic Molecular Weight287.195739685
IUPAC Name(2S,3S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-methylpentanoic acid
Traditional Name(2S,3S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-methylpentanoic acid
CAS Registry Number62632-70-6
SMILES
CC[C@H](C)[C@H](NC(=O)[C@@H](N)CCCNC(N)=N)C(O)=O
InChI Identifier
InChI=1S/C12H25N5O3/c1-3-7(2)9(11(19)20)17-10(18)8(13)5-4-6-16-12(14)15/h7-9H,3-6,13H2,1-2H3,(H,17,18)(H,19,20)(H4,14,15,16)/t7-,8-,9-/m0/s1
InChI KeyQYLJIYOGHRGUIH-CIUDSAMLSA-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
  • Isoleucine 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.35Extrapolated
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)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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 IDFDB111769
KNApSAcK IDNot Available
Chemspider ID5373133
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7009553
PDB IDNot Available
ChEBI ID73814
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. Kanapka JA, Kleinberg I: Catabolism of arginine by the mixed bacteria in human salivary sediment under conditions of low and high glucose concentration. Arch Oral Biol. 1983;28(11):1007-15. [PubMed:6419713 ]