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echinomycin


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  • Norine ID: NOR01126
  • DOI: 10.26097/nor01126
  • Family: quinomycin
  • Synonym(s): echinomycin;
  • Activity: antimicrobial, antitumor
  • Category: peptide
  • Formula: C51H64N12O12S2
  • Monoisotopic mass: 1100.420806972 g/mol
  • Comment: Echinomycin binds to DNA and inhibits RNA synthesis. Quinomycins contain a thioacetal cross bridge. In the tiostin analogues, a disulfide bond replaces the thioacetal cross-link.
  • Source: norine
  • Contributor (creation): Norine Team [CRIStAL (UMR CNRS 9189), ex-LIFL, France, Charles Viollette Institute, ProBioGEM team, Lille, France, University of Lille, France]
  • Entry information:
  • Type: partial cyclic
  • Number of monomers: 10
  • Smiles: CC(C)C6C(=O)OCC(NC(=O)c1cnc2ccccc2(n1))C(=O)NC(C)C(=O)N(C)C5C(=O)N(C)C(C(C)C)C(=O)OCC(NC(=O)c3cnc4ccccc4(n3))C(=O)NC(C)C(=O)N(C)C(CSC5SC)C(=O)N6(C)

  • Graph inference:



  • Monomeric composition and PDB SEQRES:
    1 2
    COOH-Qui D-Ser
    1
    QDS
    3
    Ala
    2
    ALA
    4
    diMe-Cys
    3
    N2C
    5
    NMe-Val
    4
    MVA
    6 7
    D-Ser COOH-Qui
    5
    QDS
    8
    Ala
    6
    ALA
    9
    NMe-Cys
    7
    NCY
    10
    NMe-Val
    8
    MVA
  • Graph representation: COOH-Qui,D-Ser,Ala,diMe-Cys,NMe-Val,D-Ser,COOH-Qui,Ala,NMe-Cys,NMe-Val @1 @0,2,9 @1,3 @2,4,8 @3,5 @4,6,7 @5 @5,8 @3,7,9 @1,8

  • Atomic structure:
    • Chemical structure
    rBAN vizualisation:
  • Streptomyces echinatus
  • gram: positive
  • taxid: 67293 (view NCBI taxonomy browser)

  • Links between organisms producing the echinomycin: Streptomyces echinatus
  • Diversification of echinomycin molecular structure by way of chemoenzymatic synthesis and heterologous expression of the engineered echinomycin biosynthetic pathway
    Watanabe K, Oguri H, Oikawa H, Current opinion in chemical biology , 2009, Apr,13(2):189-96.
    DOI: 10.1016/j.cbpa.2009.02.012
    pubMed: 19278894


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