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    Chemistry

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    Also known as: Mbi 226, 269062-93-3, Omiganan hcl, Unii-lx2p9rd54v, Mbi-226, Omiganan pentahydrochloride [usan]
    Molecular Formula
    C90H132Cl5N27O12
    Molecular Weight
    1961.4  g/mol
    InChI Key
    WTNSIKUBZJCPLJ-IQOWARLESA-N
    Omiganan Pentahydrochloride
    Omiganan Pentahydrochloride is a pentahydrochloride salt of omiganan, a synthetic cationic antimicrobial peptide with wide-spectrum activity against both gram-positive and gram-negative bacteria and fungi. Omiganan pentahydrochloride, an analog of indolicidin, acts by disrupting bacterial cytoplasmic membranes and has been tested in a topical gel for the prevention of catheter-related bloodstream infections.
    1 2D Structure

    Omiganan Pentahydrochloride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-amino-3-methylpentanoyl]amino]-4-methylpentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]-N-[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-1-[[(2S)-5-carbamimidamido-1-[[(2S)-5-carbamimidamido-1-[[(2S)-1,6-diamino-1-oxohexan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pyrrolidine-2-carboxamide;pentahydrochloride
    2.1.2 InChI
    InChI=1S/C90H127N27O12.5ClH/c1-5-51(4)75(92)85(127)113-68(41-50(2)3)80(122)109-67(32-18-38-102-90(98)99)79(121)114-71(44-54-48-105-62-27-12-8-23-58(54)62)86(128)116-39-19-34-74(116)84(126)112-70(43-53-47-104-61-26-11-7-22-57(53)61)82(124)115-72(45-55-49-106-63-28-13-9-24-59(55)63)87(129)117-40-20-33-73(117)83(125)111-69(42-52-46-103-60-25-10-6-21-56(52)60)81(123)110-66(31-17-37-101-89(96)97)78(120)108-65(30-16-36-100-88(94)95)77(119)107-64(76(93)118)29-14-15-35-91;;;;;/h6-13,21-28,46-51,64-75,103-106H,5,14-20,29-45,91-92H2,1-4H3,(H2,93,118)(H,107,119)(H,108,120)(H,109,122)(H,110,123)(H,111,125)(H,112,126)(H,113,127)(H,114,121)(H,115,124)(H4,94,95,100)(H4,96,97,101)(H4,98,99,102);5*1H/t51-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-;;;;;/m0...../s1
    2.1.3 InChI Key
    WTNSIKUBZJCPLJ-IQOWARLESA-N
    2.1.4 Canonical SMILES
    CCC(C)C(C(=O)NC(CC(C)C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)N3CCCC3C(=O)NC(CC4=CNC5=CC=CC=C54)C(=O)NC(CC6=CNC7=CC=CC=C76)C(=O)N8CCCC8C(=O)NC(CC9=CNC1=CC=CC=C19)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)N)N.Cl.Cl.Cl.Cl.Cl
    2.1.5 Isomeric SMILES
    CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC4=CNC5=CC=CC=C54)C(=O)N[C@@H](CC6=CNC7=CC=CC=C76)C(=O)N8CCC[C@H]8C(=O)N[C@@H](CC9=CNC1=CC=CC=C19)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N)N.Cl.Cl.Cl.Cl.Cl
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Ilrwpwwpwrrk-amide

    2. Mbi-226

    2.2.2 Depositor-Supplied Synonyms

    1. Mbi 226

    2. 269062-93-3

    3. Omiganan Hcl

    4. Unii-lx2p9rd54v

    5. Mbi-226

    6. Omiganan Pentahydrochloride [usan]

    7. Lx2p9rd54v

    8. Chembl1793889

    9. 626233-83-8

    10. L-isoleucyl-l-leucyl-l-arginyl-l-tryptophyl-l-prolyl-l-tryptophyl-l-tryptophyl-l-prolyl-l-tryptophyl-l-arginyl-l-arginyl-l-lysinamide Pentahydrochloride

    11. L-lysinamide, L-isoleucyl-l-leucyl-l-arginyl-l-tryptophyl-l-prolyl-l-tryptophyl-l-tryptophyl-l-prolyl-l-tryptophyl-l-arginyl-l-arginyl-, Hydrochloride (1:5)

    12. L-lysinamide, L-isoleucyl-l-leucyl-l-arginyl-l-tryptophyl-l-prolyl-l-tryptophyl-l-tryptophyl-l-prolyl-l-tryptophyl-l-arginyl-l-arginyl-, Pentahydrochloride

    2.3 Create Date
    2007-07-03
    3 Chemical and Physical Properties
    Molecular Weight 1961.4 g/mol
    Molecular Formula C90H132Cl5N27O12
    Hydrogen Bond Donor Count30
    Hydrogen Bond Acceptor Count17
    Rotatable Bond Count52
    Exact Mass1959.896191 g/mol
    Monoisotopic Mass1957.899141 g/mol
    Topological Polar Surface Area647 Ų
    Heavy Atom Count134
    Formal Charge0
    Complexity3790
    Isotope Atom Count0
    Defined Atom Stereocenter Count13
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count6
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Anti-Infective Agents

    Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

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