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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:02:13 UTC
Update Date2021-09-14 15:37:03 UTC
HMDB IDHMDB0028716
Secondary Accession Numbers
  • HMDB28716
Metabolite Identification
Common NameArginylphenylalanine
DescriptionArginylphenylalanine, also known as L-arg-L-phe or RF, 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. Arginylphenylalanine 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 arginylphenylalanine a potential biomarker for the consumption of these foods. Arginylphenylalanine 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 Arginylphenylalanine.
Structure
Data?1582753330
Synonyms
ValueSource
Arginyl-phenylalanineChEBI
L-Arg-L-pheChEBI
R-FChEBI
RFChEBI
Arg-pheHMDB
Arginine phenylalanine dipeptideHMDB
Arginine-phenylalanine dipeptideHMDB
L-Arginyl-L-phenylalanineHMDB
N-ArginylphenylalanineHMDB
N-L-Arginyl-3-phenylalanineHMDB
N-L-Arginyl-L-phenylalanineHMDB
R-F DipeptideHMDB
RF DipeptideHMDB
ArginylphenylalanineChEBI
Chemical FormulaC15H23N5O3
Average Molecular Weight321.381
Monoisotopic Molecular Weight321.180089621
IUPAC Name(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-phenylpropanoic acid
Traditional Name(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-phenylpropanoic acid
CAS Registry Number2047-13-4
SMILES
N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C15H23N5O3/c16-11(7-4-8-19-15(17)18)13(21)20-12(14(22)23)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9,16H2,(H,20,21)(H,22,23)(H4,17,18,19)/t11-,12-/m0/s1
InChI KeyPQBHGSGQZSOLIR-RYUDHWBXSA-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
  • Phenylalanine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • 3-phenylpropanoic-acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Monocyclic benzene moiety
  • N-acyl-amine
  • Benzenoid
  • Fatty amide
  • Fatty acyl
  • Guanidine
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Organic 1,3-dipolar compound
  • Carboxylic acid
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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-2.02Extrapolated
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 IDFDB111773
KNApSAcK IDNot Available
Chemspider ID133060
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound150964
PDB IDNot Available
ChEBI ID73818
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. 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 ]
  2. Dockray GJ, Reeve JR Jr, Shively J, Gayton RJ, Barnard CS: A novel active pentapeptide from chicken brain identified by antibodies to FMRFamide. Nature. 1983 Sep 22-28;305(5932):328-30. [PubMed:6137771 ]