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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:02:40 UTC
Update Date2020-02-26 21:42:25 UTC
HMDB IDHMDB0028830
Secondary Accession Numbers
  • HMDB0094678
  • HMDB28830
  • HMDB94678
Metabolite Identification
Common NameGlutamyltryptophan
DescriptionGlutamyltryptophan is a dipeptide composed of glutamate and tryptophan, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Glutamyltryptophan 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. Glutamyltryptophan can be found in feces (PMID: 27015276 ). The synthetic version of this dipeptide is named Oglufanide. It was originally developed to treat severe infectious disease in Russia (where it is a registered pharmaceutical), and was extensively studied in cancer clinical trials in the United States before being acquired by Implicit Bioscience in 2005. Oglufanide works as a regulator of the body's immune response and is being given by intranasal administration to patients with chronic hepatitis C viral infection (DB05779).
Structure
Data?1582753345
Synonyms
ValueSource
alpha-Glu-TRPChEBI
alpha-GlutamyltryptophanChEBI
L-alpha-Glu-L-TRPChEBI
L-Glu-L-TRPChEBI
OglufanideChEBI
a-Glu-TRPGenerator
Α-glu-TRPGenerator
a-GlutamyltryptophanGenerator
Α-glutamyltryptophanGenerator
L-a-Glu-L-TRPGenerator
L-Α-glu-L-TRPGenerator
Glu-TRPHMDB
L-alpha-Glutamyl-L-tryptophanHMDB
Α-L-glu-L-TRPHMDB
Α-L-glutamyl-L-tryptophanHMDB
L-Α-glutamyl-L-tryptophanHMDB
N-Α-glutamyltryptophanHMDB
N-Α-L-glutamyl-L-tryptophanHMDB
N-L-Α-glutamyltryptophanHMDB
N-L-Α-glutamyl-L-tryptophanHMDB
alpha-L-Glu-L-TRPHMDB
alpha-L-Glutamyl-L-tryptophanHMDB
N-alpha-GlutamyltryptophanHMDB
N-alpha-L-Glutamyl-L-tryptophanHMDB
N-L-alpha-GlutamyltryptophanHMDB
N-L-alpha-Glutamyl-L-tryptophanHMDB
IM 862HMDB
NSC 334073HMDB
ThymogenHMDB
TimogenHMDB
L-Glutamyl-L-tryptophanHMDB
N-GlutamyltryptophanHMDB
N-L-Glutamyl-L-tryptophanHMDB
Glutamyl-tryptophanHMDB
Glutamic acid tryptophan dipeptideHMDB
Glutamate tryptophan dipeptideHMDB
Glutamic acid-tryptophan dipeptideHMDB
Glutamate-tryptophan dipeptideHMDB
e-W DipeptideHMDB
EW dipeptideHMDB
GlutamyltryptophanHMDB, ChEBI
Chemical FormulaC16H19N3O5
Average Molecular Weight333.344
Monoisotopic Molecular Weight333.132470724
IUPAC Name(4S)-4-amino-4-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}butanoic acid
Traditional Name(4S)-4-amino-4-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}butanoic acid
CAS Registry Number38101-59-6
SMILES
N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O
InChI Identifier
InChI=1S/C16H19N3O5/c17-11(5-6-14(20)21)15(22)19-13(16(23)24)7-9-8-18-12-4-2-1-3-10(9)12/h1-4,8,11,13,18H,5-7,17H2,(H,19,22)(H,20,21)(H,23,24)/t11-,13-/m0/s1
InChI KeyLLEUXCDZPQOJMY-AAEUAGOBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Gamma amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Amino fatty acid
  • Dicarboxylic acid or derivatives
  • Substituted pyrrole
  • Fatty acyl
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.24Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility1 g/LALOGPS
logP-1.5ALOGPS
logP-2.2ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.44ChemAxon
pKa (Strongest Basic)8.45ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.51 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity84.29 m³·mol⁻¹ChemAxon
Polarizability33.6 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9x-9740000000-890ec1661e76a8511c69Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-5603950000-2672a79cdac72505e866Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0149000000-893a0bec966cfacdfeb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gx9-1794000000-9555ad44530c570861fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldi-8940000000-f108096aed88532c6fb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gc0-1479000000-5d81dd7a46786c547807Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zg0-3961000000-b5e369ea4e2f59f3c5dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-7900000000-25dc629d07f36eb5a571Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDDB05779
Phenol Explorer Compound IDNot Available
FooDB 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 Compound100094
PDB IDNot Available
ChEBI ID73512
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Belokrylov GA, Derevnina OY, Molchanova IV, Sorochinskaya EI: Immuno-, phagocytosis-modulating, and antitoxic properties of amino acids and peptide preparations. Drug Dev Ind Pharm. 1998 Feb;24(2):115-27. [PubMed:15605441 ]
  2. Belokrylov GA, Popova OYa, Sorochinskaya EI: Immuno-, phagocytosis-modulating and antitoxic properties of dipeptides are defined by the activity of their constituent amino acids. Int J Immunopharmacol. 1999 Dec;21(12):879-83. [PubMed:10606007 ]
  3. Deigin VI, Semenets TN, Zamulaeva IA, Maliutina YV, Selivanova EI, Saenko AS, Semina OV: The effects of the EW dipeptide optical and chemical isomers on the CFU-S population in intact and irradiated mice. Int Immunopharmacol. 2007 Mar;7(3):375-82. Epub 2006 Dec 20. [PubMed:17276896 ]
  4. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  5. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]