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    2D Structure
    Also known as: Doxo-emch, Inno-206, Aldoxorubicin, C28mv4im0b, 151038-96-9, Unii-c28mv4im0b
    Molecular Formula
    C37H42N4O13
    Molecular Weight
    750.7  g/mol
    InChI Key
    OBMJQRLIQQTJLR-FRTGXRTISA-N
    Aldoxorubicin is a 6-maleimidocaproyl hydrazone derivative prodrug of the anthracycline antibiotic doxorubicin (DOXO-EMCH) with antineoplastic activity. Following intravenous administration, aldoxorubicin binds selectively to the cysteine-34 position of albumin via its maleimide moiety. Doxorubicin is released from the albumin carrier after cleavage of the acid-sensitive hydrazone linker within the acidic environment of tumors and, once located intracellularly, intercalates DNA, inhibits DNA synthesis, and induces apoptosis. Albumin tends to accumulate in solid tumors as a result of high metabolic turnover, rapid angiogenesis, hypervasculature, and impaired lymphatic drainage. Because of passive accumulation within tumors, this agent may improve the therapeutic effects of doxorubicin while minimizing systemic toxicity.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[[1-[(2S,4S)-4-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-hydroxyethylidene]amino]-6-(2,5-dioxopyrrol-1-yl)hexanamide
    2.1.2 InChI
    InChI=1S/C37H42N4O13/c1-17-32(46)20(38)13-27(53-17)54-22-15-37(51,23(16-42)39-40-24(43)9-4-3-5-12-41-25(44)10-11-26(41)45)14-19-29(22)36(50)31-30(34(19)48)33(47)18-7-6-8-21(52-2)28(18)35(31)49/h6-8,10-11,17,20,22,27,32,42,46,48,50-51H,3-5,9,12-16,38H2,1-2H3,(H,40,43)/t17-,20-,22-,27-,32+,37-/m0/s1
    2.1.3 InChI Key
    OBMJQRLIQQTJLR-FRTGXRTISA-N
    2.1.4 Canonical SMILES
    CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=NNC(=O)CCCCCN6C(=O)C=CC6=O)CO)O)N)O
    2.1.5 Isomeric SMILES
    C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=NNC(=O)CCCCCN6C(=O)C=CC6=O)CO)O)N)O
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Aldoxorubicin

    2. Doxo-emch

    3. Inno-206

    2.2.2 Depositor-Supplied Synonyms

    1. Doxo-emch

    2. Inno-206

    3. Aldoxorubicin

    4. C28mv4im0b

    5. 151038-96-9

    6. Unii-c28mv4im0b

    7. Aldoxorubicin [usan:inn]

    8. Inno 206

    9. Dtxsid301318641

    10. 1361644-26-9

    2.3 Create Date
    2013-04-19
    3 Chemical and Physical Properties
    Molecular Weight 750.7 g/mol
    Molecular Formula C37H42N4O13
    XLogP31.3
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count15
    Rotatable Bond Count12
    Exact Mass750.27483741 g/mol
    Monoisotopic Mass750.27483741 g/mol
    Topological Polar Surface Area268 Ų
    Heavy Atom Count54
    Formal Charge0
    Complexity1510
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count1
    Covalently Bonded Unit Count1