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Glycyl-Cysteine

July 21, 2017
Common Name

Glycyl-Cysteine Description

Glycyl-Cysteine is a dipeptide composed of glycine and cysteine. 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 HMDB28838 (Glycyl-Cysteine)

Synonyms

Value Source g-C DipeptideHMDB GC DipeptideHMDB Gly-cysHMDB Glycine cysteine dipeptideHMDB Glycine-cysteine dipeptideHMDB GlycylcysteineHMDB L-Glycyl-L-cysteineHMDB

Chemical Formlia

C5H10N2O3S Average Molecliar Weight

178.21 Monoisotopic Molecliar Weight

178.041212886 IUPAC Name

2-(2-aminoacetamido)-3-slifanylpropanoic acid Traditional Name

2-(2-aminoacetamido)-3-slifanylpropanoic acid CAS Registry Number

Not Available SMILES

NCC(=O)NC(CS)C(O)=O

InChI Identifier

InChI=1S/C5H10N2O3S/c6-1-4(8)7-3(2-11)5(9)10/h3,11H,1-2,6H2,(H,7,8)(H,9,10)

InChI Key

MFBYPDKTAJXHNI-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

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

    • Substituents

  • Alpha-dipeptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid or derivatives
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Alkylthiol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organoslifur compound
  • Primary aliphatic amine
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • 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-3.9Extrapolated

    Predicted Properties

    Property Value Source Water Solubility6.82 mg/mLALOGPS logP-2.6ALOGPS logP-3.9ChemAxon logS-1.4ALOGPS pKa (Strongest Acidic)3.54ChemAxon pKa (Strongest Basic)8.13ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area92.42 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity41.03 m3·mol-1ChemAxon Polarizability16.79 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

    HMDB28838 Metagene Link

    HMDB28838 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Thyroxine sulfate

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Daly TA, Almeida PF, Regen SL: Sorting of lipidated peptides in fluid bilayers: a molecular-level investigation. J Am Chem Soc. 2012 Oct 17;134(41):17245-52. doi: 10.1021/ja3074825. Epub 2012 Oct 4. [PubMed:22998217 ]
    2. Ferro VA, OGrady JE, Notman J, Stimson WH: Development of a hormone neutralizing vaccine, using GnRH-glycys-PPD, for use in the treatment of oestrogen-dependent disorders. Ther Immunol. 1995 Jun;2(3):147-57. [PubMed:8885133 ]
    3. Ferro VA, Stimson WH: Effects of adjuvant, dose and carrier pre-sensitisation on the immunisation efficacy of a GnRH analogue. Drug Des Discov. 1996 Dec;14(3):179-95. [PubMed:9017362 ]
    4. Ferro VA, Stimson WH: Investigation into suitable carrier molecules for use in an anti-gonadotrophin releasing hormone vaccine. Vaccine. 1998 Jul;16(11-12):1095-102. [PubMed:9682364 ]
    5. Ke Y, Zhao J, Siu KW, Hopkinson AC: Dissociation of copper(II) ternary complexes containing cystine. Phys Chem Chem Phys. 2010 Aug 21;12(31):9017-28. doi: 10.1039/c001908a. Epub 2010 Jun 10. [PubMed:20539872 ]
    6. Greenfield NJ, Stafford WF, Hitchcock-DeGregori SE: The effect of N-terminal acetylation on the structure of an N-terminal tropomyosin peptide and alpha alpha-tropomyosin. Protein Sci. 1994 Mar;3(3):402-10. [PubMed:8019411 ]
    7. Ferro VA, Stimson WH: Immunoneutralisation of gonadotrophin releasing hormone: a potential treatment for oestrogen-dependent breast cancer. Eur J Cancer. 1997 Aug;33(9):1468-78. [PubMed:9337691 ]
    8. Ferro VA, OGrady JE, Notman J, Stimson WH: An investigation into the immunogenicity of a GnRH analogue in male rats: a comparison of the toxicity of various adjuvants used in conjunction with GnRH-glycys. Vaccine. 1996 Apr;14(5):451-7. [PubMed:8735559 ]
    9. Green DE: The reduction potentials of cysteine, glutathione and glycylcysteine. Biochem J. 1933;27(3):678-89. [PubMed:16745144 ]
    10. Dringen R, Kranich O, Loschmann PA, Hamprecht B: Use of dipeptides for the synthesis of glutathione by astroglia-rich primary cultures. J Neurochem. 1997 Aug;69(2):868-74. [PubMed:9231749 ]

    PMID: 17101120

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