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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 21:35:28 UTC
Update Date2022-11-23 22:29:18 UTC
HMDB IDHMDB0259130
Secondary Accession NumbersNone
Metabolite Identification
Common Namepyroglutamyl-histidyl-prolyl-glycyl-lysine
Descriptionpyroglutamyl-histidyl-prolyl-glycyl-lysine, also known as thyrotropin releasing hormone precursor or pglu-his-pro-gly-lys, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Based on a literature review very few articles have been published on pyroglutamyl-histidyl-prolyl-glycyl-lysine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pyroglutamyl-histidyl-prolyl-glycyl-lysine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically pyroglutamyl-histidyl-prolyl-glycyl-lysine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
2,5-Diamino-3-[4-amino-1-(5-hydroxy-3,4-dihydro-2H-pyrrol-2-yl)-1-oxobutan-2-yl]-2-(2-aminoacetyl)-6-(1H-imidazol-5-yl)-4-oxo-3-(pyrrolidine-2-carbonyl)hexanoateHMDB
Thyrotropin releasing hormone precursorHMDB
Pro-thyrotropin releasing hormoneHMDB
PGlu-his-pro-gly-lysHMDB
Pro-TRHHMDB
Pyroglutamyl-histidyl-prolyl-glycyl-lysineMeSH
Chemical FormulaC24H36N8O7
Average Molecular Weight548.601
Monoisotopic Molecular Weight548.270695531
IUPAC Name2,5-diamino-3-[4-amino-1-oxo-1-(5-oxopyrrolidin-2-yl)butan-2-yl]-2-(2-aminoacetyl)-6-(1H-imidazol-5-yl)-4-oxo-3-(pyrrolidine-2-carbonyl)hexanoic acid
Traditional Name2,5-diamino-3-[4-amino-1-oxo-1-(5-oxopyrrolidin-2-yl)butan-2-yl]-2-(2-aminoacetyl)-6-(3H-imidazol-4-yl)-4-oxo-3-(pyrrolidine-2-carbonyl)hexanoic acid
CAS Registry NumberNot Available
SMILES
NCCC(C(=O)C1CCC(=O)N1)C(C(=O)C(N)CC1=CN=CN1)(C(=O)C1CCCN1)C(N)(C(O)=O)C(=O)CN
InChI Identifier
InChI=1S/C24H36N8O7/c25-6-5-13(19(35)15-3-4-18(34)32-15)23(21(37)16-2-1-7-30-16,24(28,22(38)39)17(33)9-26)20(36)14(27)8-12-10-29-11-31-12/h10-11,13-16,30H,1-9,25-28H2,(H,29,31)(H,32,34)(H,38,39)
InChI KeyQTDGQKIQGPGWNF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Medium-chain keto acid
  • Imidazolyl carboxylic acid derivative
  • Gamma-keto acid
  • Amino fatty acid
  • Heterocyclic fatty acid
  • Branched fatty acid
  • Aralkylamine
  • Beta-keto acid
  • Beta-aminoketone
  • Beta-hydroxy ketone
  • 2-pyrrolidone
  • Pyrrolidone
  • Keto acid
  • Fatty acyl
  • Gamma-aminoketone
  • Azole
  • Pyrrolidine
  • Heteroaromatic compound
  • Alpha-aminoketone
  • Imidazole
  • Ketone
  • Amino acid
  • Lactam
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Primary amine
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected 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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID17334382
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16206211
PDB IDNot Available
ChEBI IDNot Available
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]