Np mrd loader

Record Information
Version1.0
Created at2022-05-12 15:20:25 UTC
Updated at2022-05-12 15:20:25 UTC
NP-MRD IDNP0136667
Secondary Accession NumbersNone
Natural Product Identification
Common NameTryptophyl-Glycine
DescriptionTryptophyl-Glycine, also known as W-g dipeptide or TRP-gly, 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-Glycine is a very strong basic compound (based on its pKa). Tryptophyl-Glycine is a dipeptide composed of tryptophan and glycine. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite. 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. It was first documented in 1965 (PMID: 5879901). It is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 22888404) (PMID: 18950135) (PMID: 14323609) (PMID: 231893) (PMID: 14290281) (PMID: 9880037).
Structure
Thumb
Synonyms
ValueSource
L-Tryptophyl-L-glycineHMDB
TRP-GlyHMDB
Tryptophan glycine dipeptideHMDB
Tryptophan-glycine dipeptideHMDB
TryptophylglycineHMDB
W-g DipeptideHMDB
WG DipeptideHMDB
TryptophanylglycineHMDB
2-{[2-amino-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}acetateGenerator
Chemical FormulaC13H15N3O3
Average Mass261.2765 Da
Monoisotopic Mass261.11134 Da
IUPAC Name2-[2-amino-3-(1H-indol-3-yl)propanamido]acetic acid
Traditional Name[2-amino-3-(1H-indol-3-yl)propanamido]acetic acid
CAS Registry NumberNot Available
SMILES
NC(CC1=CNC2=C1C=CC=C2)C(=O)NCC(O)=O
InChI Identifier
InChI=1S/C13H15N3O3/c14-10(13(19)16-7-12(17)18)5-8-6-15-11-4-2-1-3-9(8)11/h1-4,6,10,15H,5,7,14H2,(H,16,19)(H,17,18)
InChI KeyUYKREHOKELZSPB-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
  • Aralkylamine
  • Fatty amide
  • Substituted pyrrole
  • Fatty acyl
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Amine
  • Primary 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-0.94ALOGPS
logP-2.2ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.72ChemAxon
pKa (Strongest Basic)7.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area108.21 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.01 m³·mol⁻¹ChemAxon
Polarizability26.81 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029083
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 Compound263471
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Eisenberg AS, Juszczak LJ: Correlation of TrpGly and GlyTrp Rotamer Structure with W7 and W10 UV Resonance Raman Modes and Fluorescence Emission Shifts. J Amino Acids. 2012;2012:735076. doi: 10.1155/2012/735076. Epub 2012 Jul 22. [PubMed:22888404 ]
  2. Pan Y, Birkedal H, Pattison P, Brown D, Chapuis G: Molecular dynamics study of tryptophylglycine: a dipeptide nanotube with confined water. J Phys Chem B. 2004 May 20;108(20):6458-66. doi: 10.1021/jp037219v. [PubMed:18950135 ]
  3. Yajima H, Kubo K: Studies on peptides. IV. The synthesis of D-histidyl-L-phenylalanyl-L- arginyl-L-tryptophylglycine and L-histidyl-L-phenylalanyl-L-arginyl-D-tryptophylglycine and their physiological properties in frog melanocyte in vitro. Chem Pharm Bull (Tokyo). 1965 Jul;13(7):759-64. doi: 10.1248/cpb.13.759. [PubMed:5879901 ]
  4. YAJIMA H, KUBO K: THE SYNTHESIS OF D-HISTIDYL-L-PHENYLALANYL-L-ARGINYL-L-TRYPTOPHYLGLYCINE AND L-HISTIDYL-L-PHENYLALANYL-L-ARGINYL-D-TRYPTOPHYLGLYCINE AND THEIR PHYSIOLOGICAL PROPERTIES IN FROG MELANOCYTE. Biochim Biophys Acta. 1965 Mar 8;97:596-7. doi: 10.1016/0304-4165(65)90176-5. [PubMed:14323609 ]
  5. Partanen S, Kaakkola S, Kaariainen I: Tryptophylglycine dipeptide in ACTH/MSH cells of the human hypophysis: its identification and studies on its antinociceptive effects in mice. Acta Physiol Scand. 1979 Nov;107(3):213-18. doi: 10.1111/j.1748-1716.1979.tb06465.x. [PubMed:231893 ]
  6. YAJIMA H, KUBO K: STUDIES ON PEPTIDES. II. SYNTHESIS AND PHYSIOLOGICAL PROPERTIES OF D-HISTIDYL-D-PHENYLALANYL-D-ARGINYL-D-TRYPTOPHYLGLYCINE, AN OPTICAL ANTIPODE OF AN ACTIVE FRAGMENT OF ALPHA-MELANOCYTE-STIMULATING HORMONE. J Am Chem Soc. 1965 May 5;87:2039-44. doi: 10.1021/ja01087a032. [PubMed:14290281 ]
  7. Goldmann W, Chong A, Foster J, Hope J, Hunter N: The shortest known prion protein gene allele occurs in goats, has only three octapeptide repeats and is non-pathogenic. J Gen Virol. 1998 Dec;79 ( Pt 12):3173-6. doi: 10.1099/0022-1317-79-12-3173. [PubMed:9880037 ]
  8. Hano K, Koida M, Yajima H, Kubo K, Oshima T: Sodium hydroxide treatment of L-histidyl-L-phenylalanyl-L-arginyl-L-tryptophylglycine and its potentiated melanocyte-stimulating activity in vitro. Biochim Biophys Acta. 1966 Feb 28;115(2):337-44. doi: 10.1016/0304-4165(66)90433-8. [PubMed:5943437 ]
  9. Russo FS, Persson AV, Wilson IB: A fluorogenic substrate for angiotensin-converting enzyme in plasma. Clin Chem. 1978 Sep;24(9):1539-42. [PubMed:210982 ]
  10. Tan HK, Wheeler WB, Wei CI: Reaction of chlorine dioxide with amino acids and peptides: kinetics and mutagenicity studies. Mutat Res. 1987 Aug;188(4):259-66. doi: 10.1016/0165-1218(87)90002-4. [PubMed:3302695 ]