Np mrd loader

Record Information
Version2.0
Created at2022-05-12 15:20:31 UTC
Updated at2022-05-12 15:20:31 UTC
NP-MRD IDNP0136671
Secondary Accession NumbersNone
Natural Product Identification
Common NameTryptophyl-Lysine
DescriptionTryptophyl-Lysine, also known as W-K dipeptide or TRP-lys, 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. Tryptophyl-Lysine is a very strong basic compound (based on its pKa). It is an incomplete breakdown product of protein digestion or protein catabolism. Tryptophyl-Lysine is a dipeptide composed of tryptophan and lysine. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite. Tryptophyl-Lysine was first documented in 1985 (PMID: 4052400). 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: 4052401).
Structure
Thumb
Synonyms
ValueSource
L-Tryptophyl-L-lysineHMDB
TRP-LysHMDB
Tryptophan lysine dipeptideHMDB
Tryptophan-lysine dipeptideHMDB
TryptophyllysineHMDB
W-K DipeptideHMDB
WK DipeptideHMDB
6-Amino-2-{[2-amino-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}hexanoateGenerator
Chemical FormulaC17H24N4O3
Average Mass332.3975 Da
Monoisotopic Mass332.18484 Da
IUPAC Name6-amino-2-[2-amino-3-(1H-indol-3-yl)propanamido]hexanoic acid
Traditional Name6-amino-2-[2-amino-3-(1H-indol-3-yl)propanamido]hexanoic acid
CAS Registry NumberNot Available
SMILES
NCCCCC(NC(=O)C(N)CC1=CNC2=C1C=CC=C2)C(O)=O
InChI Identifier
InChI=1S/C17H24N4O3/c18-8-4-3-7-15(17(23)24)21-16(22)13(19)9-11-10-20-14-6-2-1-5-12(11)14/h1-2,5-6,10,13,15,20H,3-4,7-9,18-19H2,(H,21,22)(H,23,24)
InChI KeyDZHDVYLBNKMLMB-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
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Triptan
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Medium-chain fatty acid
  • Amino fatty acid
  • Heterocyclic fatty acid
  • Aralkylamine
  • Fatty amide
  • Substituted pyrrole
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Organoheterocyclic compound
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Primary amine
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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-1.2ALOGPS
logP-1.8ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.79ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area134.23 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity90.81 m³·mol⁻¹ChemAxon
Polarizability35.57 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029088
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 Compound18799209
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Shine NR, James TL: Interactions of diastereomeric tripeptides of lysyl-5-fluorotryptophyllysine with DNA. 1. Optical and 19F NMR studies of native DNA complexes. Biochemistry. 1985 Jul 30;24(16):4333-41. doi: 10.1021/bi00337a012. [PubMed:4052400 ]
  2. Shine NR, Bubienko E, James TL: Interactions of diastereomeric tripeptides of lysyl-5-fluorotryptophyllysine with DNA. 2. Optical, 19F NMR, and strand cleavage studies of apurinic DNA complexes. Biochemistry. 1985 Jul 30;24(16):4341-5. doi: 10.1021/bi00337a013. [PubMed:4052401 ]