Np mrd loader

Record Information
Version2.0
Created at2022-05-12 15:20:48 UTC
Updated at2022-05-12 15:20:48 UTC
NP-MRD IDNP0136682
Secondary Accession NumbersNone
Natural Product Identification
Common NameTyrosyl-Arginine
DescriptionTyrosyl-Arginine, also known as y-R dipeptide or D-kyotorphin, 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. Tyrosyl-Arginine is a very strong basic compound (based on its pKa). This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite. It is an incomplete breakdown product of protein digestion or protein catabolism. Tyrosyl-Arginine is a dipeptide composed of tyrosine and arginine. Tyrosyl-Arginine was first documented in 1990 (PMID: 2154586). 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 (PMID: 10793305) (PMID: 18600923) (PMID: 8345819).
Structure
Thumb
Synonyms
ValueSource
L-Tyrosyl-L-arginineHMDB
Tyr-argHMDB
Tyrosine arginine dipeptideHMDB
Tyrosine-arginine dipeptideHMDB
TyrosylarginineHMDB
Y-R dipeptideHMDB
YR dipeptideHMDB
Kyotorphin, 3H-labeled, (L-tyr-D-arg)-isomerHMDB
Kyotorphin, (L-tyr-D-arg)-isomerHMDB
D-KyotorphinHMDB
Kyotorphin, 3H-labeled, (L-tyr-L-arg)-isomerHMDB
L-Tyrosyl-D-arginineHMDB
KyotorphinHMDB
(D-Arg(2))-kyotorphinHMDB
Kyotorphin, 14C-labeled, (L-tyr-L-arg)-isomerHMDB
2-{[2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-5-carbamimidamidopentanoateGenerator
Chemical FormulaC15H23N5O4
Average Mass337.3742 Da
Monoisotopic Mass337.17500 Da
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3.1ALOGPS
logP-2.5ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.51ChemAxon
pKa (Strongest Basic)12.1ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area174.55 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity97.82 m³·mol⁻¹ChemAxon
Polarizability35.51 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029099
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2932
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Simpkins C: A new cytochrome C reducing dipeptide. J Natl Med Assoc. 1990 Feb;82(2):113-6. [PubMed:2154586 ]
  2. Kee AJ, Smith RC: Addition of tyrosyl-arginine to parenteral nutrition is anabolic in unstressed rats. Nutrition. 2000 May;16(5):361-7. doi: 10.1016/s0899-9007(00)00232-x. [PubMed:10793305 ]
  3. Schwarz A, Wandrey C, Steinke D, Kula MR: A two-step enzymatic synthesis of dipeptides. Biotechnol Bioeng. 1992 Jan 20;39(2):132-40. doi: 10.1002/bit.260390203. [PubMed:18600923 ]
  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. doi: 10.1016/0026-0495(93)90007-b. [PubMed:8345819 ]