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Methionyl-Glycine

July 21, 2017
Common Name

Methionyl-Glycine Description

Methionyl-Glycine is a dipeptide composed of methionine and glycine. It 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. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Structure for HMDB28973 (Methionyl-Glycine)

Synonyms

Value Source L-Methionyl-L-glycineHMDB m-g DipeptideHMDB Met-glyHMDB Methionine glycine dipeptideHMDB Methionine-glycine dipeptideHMDB MethionylglycineHMDB MG DipeptideHMDB

Chemical Formlia

C7H14N2O3S Average Molecliar Weight

206.263 Monoisotopic Molecliar Weight

206.072513014 IUPAC Name

2-[2-amino-4-(methylslifanyl)butanamido]acetic acid Traditional Name

[2-amino-4-(methylslifanyl)butanamido]acetic acid CAS Registry Number

Not Available SMILES

CSCCC(N)C(=O)NCC(O)=O

InChI Identifier

InChI=1S/C7H14N2O3S/c1-13-3-2-5(8)7(12)9-4-6(10)11/h5H,2-4,8H2,1H3,(H,9,12)(H,10,11)

InChI Key

QXOHLNCNYLGICT-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Dipeptides Alternative Parents

  • Methionine and derivatives
  • N-acyl-alpha amino acids
  • Alpha amino acid amides
  • N-acyl amines
  • Secondary carboxylic acid amides
  • Amino acids
  • Slifenyl compounds
  • Monocarboxylic acids and derivatives
  • Dialkylthioethers
  • Carboxylic acids
  • Organopnictogen compounds
  • Organic oxides
  • Monoalkylamines
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Alpha-dipeptide
  • Methionine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Dialkylthioether
  • Slifenyl compound
  • Thioether
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organoslifur compound
  • Primary amine
  • Aliphatic acyclic compound

    • Molecliar Framework

    Aliphatic acyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Endogenous

    • Biofunction

    Not Available Application

    Not Available Cellliar locations

    Not Available Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP-3.3Extrapolated

    Predicted Properties

    Property Value Source Water Solubility10.1 mg/mLALOGPS logP-1.9ALOGPS logP-3.3ChemAxon logS-1.3ALOGPS pKa (Strongest Acidic)3.78ChemAxon pKa (Strongest Basic)8.42ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area92.42 Å2ChemAxon Rotatable Bond Count6ChemAxon Refractivity50.39 m3·mol-1ChemAxon Polarizability21.23 Å3ChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

    Not Available Biofluid Locations

    Not Available Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    Not Available KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB28973 Metagene Link

    HMDB28973 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: C 87

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Morozova OB, Korchak SE, Vieth HM, Yurkovskaya AV: Photo-CIDNP study of transient radicals of Met-Gly and Gly-Met peptides in aqueous solution at variable pH. J Phys Chem B. 2009 May 21;113(20):7398-406. doi: 10.1021/jp8112182. [PubMed:19438284 ]
    2. Paquet A, Sarwar G: Determination of bioavailability of some long-chain N-substituted derivatives of L-methionine and L-lysine. Can J Biochem. 1980 Jul;58(7):577-80. [PubMed:6778594 ]
    3. Kaluderovic GN, Schmidt H, Paschke R, Kalinowski B, Dietrich A, Mueller T, Steinborn D: Platinum(II) complexes with l-methionylglycine and l-methionyl-l-leucine ligands: synthesis, characterization and in vitro antitumoral activity. J Inorg Biochem. 2007 Mar;101(3):543-9. Epub 2006 Nov 30. [PubMed:17223197 ]
    4. McCollum MQ, Webb KE Jr: Glycyl-L-sarcosine absorption across ovine omasal epithelium during coincubation with other peptide substrates and volatile fatty acids. J Anim Sci. 1998 Oct;76(10):2706-11. [PubMed:9814913 ]
    5. Bressan M, Ettorre R, Marchiori F, Valle G: Coordination chemistry of peptides. Part II. Crystal structure of cyclo-L-methionylglycine and studies of metal complexation. Int J Pept Protein Res. 1982 Apr;19(4):402-7. [PubMed:7118410 ]
    6. Matthews JC, Wong EA, Bender PK, Bloomquist JR, Webb KE Jr: Demonstration and characterization of dipeptide transport system activity in sheep omasal epithelium by expression of mRNA in Xenopus laevis oocytes. J Anim Sci. 1996 Jul;74(7):1720-7. [PubMed:8818821 ]
    7. Callaway JE, Lai J, Haselbeck B, Baltaian M, Bonnesen SP, Weickmann J, Wilcox G, Lei SP: Modification of the C terminus of cecropin is essential for broad-spectrum antimicrobial activity. Antimicrob Agents Chemother. 1993 Aug;37(8):1614-9. [PubMed:8215272 ]
    8. Moneton P, Sarthou P, Le Goffic F: Transport and hydrolysis of peptides in Saccharomyces cerevisiae. J Gen Microbiol. 1986 Aug;132(8):2147-53. [PubMed:3540196 ]
    9. Matthews JC, Webb KE Jr: Absorption of L-carnosine, L-methionine, and L-methionylglycine by isolated sheep ruminal and omasal epithelial tissue. J Anim Sci. 1995 Nov;73(11):3464-75. [PubMed:8586607 ]

    PMID: 9776361

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