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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 21:03:41 UTC
Update Date2021-09-14 15:37:03 UTC
HMDB IDHMDB0029099
Secondary Accession Numbers
  • HMDB29099
Metabolite Identification
Common NameTyrosyl-Arginine
DescriptionTyrosyl-Arginine is a dipeptide composed of tyrosine and arginine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite.
Structure
Data?1582753375
Synonyms
ValueSource
L-Tyrosyl-L-arginineHMDB, MeSH
Tyr-argHMDB, MeSH
Tyrosine arginine dipeptideHMDB
Tyrosine-arginine dipeptideHMDB
TyrosylarginineHMDB
Y-R dipeptideHMDB
YR dipeptideHMDB
Kyotorphin, 3H-labeled, (L-tyr-D-arg)-isomerMeSH, HMDB
Kyotorphin, (L-tyr-D-arg)-isomerMeSH, HMDB
D-KyotorphinMeSH, HMDB
Kyotorphin, 3H-labeled, (L-tyr-L-arg)-isomerMeSH, HMDB
L-Tyrosyl-D-arginineMeSH, HMDB
KyotorphinMeSH, HMDB
(D-Arg(2))-kyotorphinMeSH, HMDB
Kyotorphin, 14C-labeled, (L-tyr-L-arg)-isomerMeSH, HMDB
2-{[2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-5-carbamimidamidopentanoateGenerator, HMDB
Chemical FormulaC15H23N5O4
Average Molecular Weight337.3742
Monoisotopic Molecular Weight337.175004249
IUPAC Name2-[2-amino-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanoic acid
Traditional Name2-[2-amino-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanoic acid
CAS Registry NumberNot Available
SMILES
NC(CC1=CC=C(O)C=C1)C(=O)NC(CCCNC(N)=N)C(O)=O
InChI Identifier
InChI=1S/C15H23N5O4/c16-11(8-9-3-5-10(21)6-4-9)13(22)20-12(14(23)24)2-1-7-19-15(17)18/h3-6,11-12,21H,1-2,7-8,16H2,(H,20,22)(H,23,24)(H4,17,18,19)
InChI KeyJXNRXNCCROJZFB-UHFFFAOYSA-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
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Fatty amide
  • Fatty acyl
  • Guanidine
  • Amino acid
  • Amino acid or derivatives
  • 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 DescriptorsNot Available
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-2.48Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112103
KNApSAcK IDNot Available
Chemspider ID2829
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2932
PDB IDNot Available
ChEBI IDNot Available
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. Kee AJ, Smith RC: Addition of tyrosyl-arginine to parenteral nutrition is anabolic in unstressed rats. Nutrition. 2000 May;16(5):361-7. [PubMed:10793305 ]
  2. Schwarz A, Wandrey C, Steinke D, Kula MR: A two-step enzymatic synthesis of dipeptides. Biotechnol Bioeng. 1992 Jan 20;39(2):132-40. [PubMed:18600923 ]
  3. Kee AJ, Smith RC, Gross AS, Madsen DC, Rowe B: The effect of dipeptide structure on dipeptide and amino acid clearance in rats. Metabolism. 1994 Nov;43(11):1373-8. [PubMed:7968592 ]
  4. Kee AJ, Smith RC: Organ clearance of tyrosyl-arginine and its effect on amino acid metabolism in young sheep. Metabolism. 1993 Aug;42(8):958-66. [PubMed:8345819 ]
  5. Simpkins C: A new cytochrome C reducing dipeptide. J Natl Med Assoc. 1990 Feb;82(2):113-6. [PubMed:2154586 ]