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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:02:52 UTC
Update Date2020-02-26 21:42:31 UTC
HMDB IDHMDB0028885
Secondary Accession Numbers
  • HMDB28885
Metabolite Identification
Common NameHistidylglycine
DescriptionHistidylglycine is a dipeptide composed of histidine and glycine. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.
Structure
Data?1582753351
Synonyms
ValueSource
HGChEBI
Histidinyl-glycineChEBI
HistidylglycineChEBI
L-His-glyChEBI
H-G dipeptideHMDB
HG dipeptideHMDB
His-GlyHMDB
Histidine glycine dipeptideHMDB
Histidine-glycine dipeptideHMDB
HistidinylglycineHMDB
Histidyl-glycineHMDB
L-HistidinylglycineHMDB
L-HistidylglycineHMDB
N-(L-Histidyl)glycineHMDB
N-HistidinylglycineHMDB
N-HistidylglycineHMDB
N-L-HistidinylglycineHMDB
N-L-HistidylglycineHMDB
Chemical FormulaC8H12N4O3
Average Molecular Weight212.209
Monoisotopic Molecular Weight212.090940262
IUPAC Name2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]acetic acid
Traditional Name[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]acetic acid
CAS Registry Number2578-58-7
SMILES
N[C@@H](CC1=CNC=N1)C(=O)NCC(O)=O
InChI Identifier
InChI=1S/C8H12N4O3/c9-6(1-5-2-10-4-12-5)8(15)11-3-7(13)14/h2,4,6H,1,3,9H2,(H,10,12)(H,11,15)(H,13,14)/t6-/m0/s1
InChI KeyLYCVKHSJGDMDLM-LURJTMIESA-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
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-4.58Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility8.58 g/LALOGPS
logP-2.8ALOGPS
logP-4.3ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)7.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area121.1 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity50.3 m³·mol⁻¹ChemAxon
Polarizability20.48 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID91417
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101179
PDB IDNot Available
ChEBI ID73930
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wickrama Arachchilage AP, Wang F, Feyer V, Plekan O, Prince KC: Photoelectron spectra and structures of three cyclic dipeptides: PhePhe, TyrPro, and HisGly. J Chem Phys. 2012 Mar 28;136(12):124301. doi: 10.1063/1.3693763. [PubMed:22462851 ]
  2. Tesfai TM, Green BJ, Margerum DW: Decomposition kinetics of Ni(III)-peptide complexes with histidine and histamine as the third residue. Inorg Chem. 2004 Oct 18;43(21):6726-33. [PubMed:15476372 ]
  3. Hanaki A, Odani A: Transport of Cu(II) from an albumin mimic peptide, GlyGlyHisGly, to histidine and penicillamine. J Inorg Biochem. 2007 Oct;101(10):1428-37. Epub 2007 Jun 12. [PubMed:17643491 ]
  4. Burke SK, Xu Y, Margerum DW: Cu(II)Gly2HisGly oxidation by H2O2/ascorbic acid to the CuIII complex and its subsequent decay to alkene peptides. Inorg Chem. 2003 Sep 22;42(19):5807-17. [PubMed:12971748 ]
  5. Kapota C, Ohanessian G: The low energy tautomers and conformers of the dipeptides HisGly and GlyHis and of their sodium ion complexes in the gas phase. Phys Chem Chem Phys. 2005 Nov 7;7(21):3744-55. Epub 2005 Sep 9. [PubMed:16358024 ]
  6. Wang P, Wesdemiotis C, Kapota C, Ohanessian G: The sodium ion affinities of simple di-, tri-, and tetrapeptides. J Am Soc Mass Spectrom. 2007 Mar;18(3):541-52. Epub 2006 Dec 8. [PubMed:17157529 ]
  7. Green BJ, Tesfai TM, Margerum DW: Nickel(III) oxidation of its glycylglycylhistamine complex. Dalton Trans. 2004 Nov 7;(21):3508-14. Epub 2004 Sep 20. [PubMed:15510270 ]