Np mrd loader

Record Information
Version2.0
Created at2022-05-12 15:12:26 UTC
Updated at2022-05-12 15:12:26 UTC
NP-MRD IDNP0136355
Secondary Accession NumbersNone
Natural Product Identification
Common NameArginylphenylalanine
DescriptionArginylphenylalanine, also known as RF or L-arg-L-phe, 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 is a very strong basic compound (based on its pKa). Arginylphenylalanine was first documented in 1983 (PMID: 6137771). It is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 22945436).
Structure
Thumb
Synonyms
ValueSource
Arginyl-phenylalanineChEBI
L-Arg-L-pheChEBI
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 Mass321.3810 Da
Monoisotopic Mass321.18009 Da
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 NumberNot Available
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
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
  • 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
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-2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.7ChemAxon
pKa (Strongest Basic)12.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area154.32 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity95.84 m³·mol⁻¹ChemAxon
Polarizability34.23 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0028716
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 Compound150964
PDB IDNot Available
ChEBI ID73818
Good Scents IDNot Available
References
General References
  1. Kagebayashi T, Kontani N, Yamada Y, Mizushige T, Arai T, Kino K, Ohinata K: Novel CCK-dependent vasorelaxing dipeptide, Arg-Phe, decreases blood pressure and food intake in rodents. Mol Nutr Food Res. 2012 Sep;56(9):1456-63. doi: 10.1002/mnfr.201200168. Epub 2012 Aug 1. [PubMed:22945436 ]
  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. doi: 10.1038/305328a0. [PubMed:6137771 ]