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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:02:35 UTC
Update Date2022-09-22 18:34:55 UTC
HMDB IDHMDB0028813
Secondary Accession Numbers
  • HMDB28813
Metabolite Identification
Common NameGlutamylarginine
DescriptionGlutamylarginine is a dipeptide composed of glutamate and arginine, 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. Glutamylarginine 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.
Structure
Thumb
Synonyms
Chemical FormulaC11H21N5O5
Average Molecular Weight303.319
Monoisotopic Molecular Weight303.154268796
IUPAC Name(2S)-2-[(2S)-2-amino-4-carboxybutanamido]-5-carbamimidamidopentanoic acid
Traditional Name(2S)-2-[(2S)-2-amino-4-carboxybutanamido]-5-carbamimidamidopentanoic acid
CAS Registry Number7219-59-2
SMILES
N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O
InChI Identifier
InChI=1S/C11H21N5O5/c12-6(3-4-8(17)18)9(19)16-7(10(20)21)2-1-5-15-11(13)14/h6-7H,1-5,12H2,(H,16,19)(H,17,18)(H,20,21)(H4,13,14,15)/t6-,7-/m0/s1
InChI KeyMPZWMIIOPAPAKE-BQBZGAKWSA-N
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
  • Glutamic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Amino fatty acid
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Amino acid or derivatives
  • Carboxamide group
  • Guanidine
  • Secondary carboxylic acid amide
  • Organic 1,3-dipolar compound
  • Carboxylic acid
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Primary aliphatic amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-6.29Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB111858
KNApSAcK IDNot Available
Chemspider ID7972216
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9796450
PDB IDNot Available
ChEBI ID157844
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Varadarajan N, Rodriguez S, Hwang BY, Georgiou G, Iverson BL: Highly active and selective endopeptidases with programmed substrate specificities. Nat Chem Biol. 2008 May;4(5):290-4. doi: 10.1038/nchembio.80. [PubMed:18391948 ]
  2. Hsu EC, Dorig RE, Sarangi F, Marcil A, Iorio C, Richardson CD: Artificial mutations and natural variations in the CD46 molecules from human and monkey cells define regions important for measles virus binding. J Virol. 1997 Aug;71(8):6144-54. [PubMed:9223509 ]
  3. van Rossum EF, Koper JW, Huizenga NA, Uitterlinden AG, Janssen JA, Brinkmann AO, Grobbee DE, de Jong FH, van Duyn CM, Pols HA, Lamberts SW: A polymorphism in the glucocorticoid receptor gene, which decreases sensitivity to glucocorticoids in vivo, is associated with low insulin and cholesterol levels. Diabetes. 2002 Oct;51(10):3128-34. [PubMed:12351458 ]
  4. Russcher H, van Rossum EF, de Jong FH, Brinkmann AO, Lamberts SW, Koper JW: Increased expression of the glucocorticoid receptor-A translational isoform as a result of the ER22/23EK polymorphism. Mol Endocrinol. 2005 Jul;19(7):1687-96. Epub 2005 Mar 3. [PubMed:15746190 ]