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    Chemistry

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    Also known as: Thiostrepton, Thiactin, 1393-48-2, Sr-05000001899, Ncgc00016576-01, Cas-1393-48-2
    Molecular Formula
    C72H85N19O18S5
    Molecular Weight
    1664.9  g/mol
    InChI Key
    NSFFHOGKXHRQEW-DVRIZHICSA-N
    Thiostrepton
    One of the CYCLIC PEPTIDES from Streptomyces that is active against gram-positive bacteria. In veterinary medicine, it has been used in mastitis caused by gram-negative organisms and in dermatologic disorders.
    1 2D Structure

    Thiostrepton

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[3-[(3-amino-3-oxoprop-1-en-2-yl)amino]-3-oxoprop-1-en-2-yl]-2-[(11E)-37-butan-2-yl-18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-59-hydroxy-8,31-bis(1-hydroxyethyl)-26,40,46-trimethyl-43-methylidene-6,9,16,23,28,38,41,44,47-nonaoxo-27-oxa-3,13,20,56-tetrathia-7,10,17,24,36,39,42,45,48,52,58,61,62,63,64-pentadecazanonacyclo[23.23.9.329,35.12,5.112,15.119,22.154,57.01,53.032,60]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazole-4-carboxamide
    2.1.2 InChI
    InChI=1S/C72H85N19O18S5/c1-14-26(3)47-63(105)78-30(7)57(99)75-28(5)56(98)76-31(8)58(100)91-72-19-18-40(66-85-43(22-111-66)59(101)77-29(6)55(97)74-27(4)54(73)96)81-52(72)42-21-112-67(83-42)49(34(11)109-69(107)41-20-37(32(9)92)36-16-17-39(79-47)51(95)50(36)80-41)89-60(102)44-24-113-68(86-44)53(71(13,108)35(12)94)90-62(104)45-23-110-65(84-45)38(15-2)82-64(106)48(33(10)93)88-61(103)46-25-114-70(72)87-46/h15-17,20-22,24-26,30-35,39,45,47-49,51-53,79,92-95,108H,4-6,14,18-19,23H2,1-3,7-13H3,(H2,73,96)(H,74,97)(H,75,99)(H,76,98)(H,77,101)(H,78,105)(H,82,106)(H,88,103)(H,89,102)(H,90,104)(H,91,100)/b38-15+
    2.1.3 InChI Key
    NSFFHOGKXHRQEW-DVRIZHICSA-N
    2.1.4 Canonical SMILES
    CCC(C)C1C(=O)NC(C(=O)NC(=C)C(=O)NC(C(=O)NC23CCC(=NC2C4=CSC(=N4)C(C(OC(=O)C5=NC6=C(C=CC(C6O)N1)C(=C5)C(C)O)C)NC(=O)C7=CSC(=N7)C(NC(=O)C8CSC(=N8)C(=CC)NC(=O)C(NC(=O)C9=CSC3=N9)C(C)O)C(C)(C(C)O)O)C1=NC(=CS1)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C)C
    2.1.5 Isomeric SMILES
    CCC(C)C1C(=O)NC(C(=O)NC(=C)C(=O)NC(C(=O)NC23CCC(=NC2C4=CSC(=N4)C(C(OC(=O)C5=NC6=C(C=CC(C6O)N1)C(=C5)C(C)O)C)NC(=O)C7=CSC(=N7)C(NC(=O)C8CSC(=N8)/C(=C\C)/NC(=O)C(NC(=O)C9=CSC3=N9)C(C)O)C(C)(C(C)O)O)C1=NC(=CS1)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C)C
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Gargon

    2. Thiactin

    3. Thiostrepton

    2.2.2 Depositor-Supplied Synonyms

    1. Thiostrepton

    2. Thiactin

    3. 1393-48-2

    4. Sr-05000001899

    5. Ncgc00016576-01

    6. Cas-1393-48-2

    7. Prestwick2_000522

    8. Dsstox_cid_20625

    9. Dsstox_rid_79517

    10. Dsstox_gsid_40625

    11. Schembl25847

    12. Bspbio_002468

    13. Spectrum1505111

    14. Chembl410968

    15. Hms1569j05

    16. Hms2093i06

    17. Pharmakon1600-01505111

    18. Tox21_110504

    19. Nsc759821

    20. Akos026750174

    21. Ccg-213336

    22. Nsc-759821

    23. Ncgc00096010-01

    24. Ncgc00096010-02

    25. Sbi-0206784.p001

    26. Ab01563039_01

    27. Sr-05000001899-1

    28. Sr-05000001899-3

    29. Sr-05000001899-4

    2.3 Create Date
    2007-07-03
    3 Chemical and Physical Properties
    Molecular Weight 1664.9 g/mol
    Molecular Formula C72H85N19O18S5
    XLogP30.6
    Hydrogen Bond Donor Count17
    Hydrogen Bond Acceptor Count31
    Rotatable Bond Count12
    Exact Mass1663.4923528 g/mol
    Monoisotopic Mass1663.4923528 g/mol
    Topological Polar Surface Area701 Ų
    Heavy Atom Count114
    Formal Charge0
    Complexity3940
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count17
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

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