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    AVA6000

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    2D Structure
    Also known as: Ava6000, Ava-6000, Unii-7xpb9b6mua, 1841402-73-0, Schembl17345374
    Molecular Formula
    C41H44N4O14
    Molecular Weight
    816.8  g/mol
    InChI Key
    CNGRCGLLHXRRTQ-SXSFFGRISA-N
    FDA UNII
    7XPB9B6MUA
    Fibroblast Activation Protein Alpha-activated Doxorubicin Prodrug AVA6000 is a prodrug of the anthracycline antineoplastic antibiotic doxorubicin composed of doxorubicin covalently bonded to the dipeptide N-(pyridine-4-carbonyl)-D-Ala-L-Pro, with potential antineoplastic activity. Upon administration, fibroblast activation protein alpha (FAP)-activated doxorubicin prodrug AVA6000 is hydrolyzed by FAP, which is overexpressed on cancer-associated fibroblasts (CAFs) in the tumor microenvironment (TME). Doxorubicin is released in the TME, and intercalates into DNA and interacts with topoisomerase II. This leads to an inhibition of DNA replication and repair, and prevents RNA and protein synthesis. By targeting the delivery of doxorubicin directly to the tumor, AVA6000 may result in less systemic toxicities. FAP, a membrane-bound protease, is overexpressed on CAFs in various tumors but minimally expressed on normal, healthy cells.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[(2R)-1-[(2S)-2-[[(2S,3S,4S,6R)-3-hydroxy-2-methyl-6-[[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]oxan-4-yl]carbamoyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]pyridine-4-carboxamide
    2.1.2 InChI
    InChI=1S/C41H44N4O14/c1-18(43-38(53)20-9-11-42-12-10-20)40(55)45-13-5-7-24(45)39(54)44-23-14-28(58-19(2)33(23)48)59-26-16-41(56,27(47)17-46)15-22-30(26)37(52)32-31(35(22)50)34(49)21-6-4-8-25(57-3)29(21)36(32)51/h4,6,8-12,18-19,23-24,26,28,33,46,48,50,52,56H,5,7,13-17H2,1-3H3,(H,43,53)(H,44,54)/t18-,19+,23+,24+,26+,28+,33-,41+/m1/s1
    2.1.3 InChI Key
    CNGRCGLLHXRRTQ-SXSFFGRISA-N
    2.2 Other Identifiers
    2.2.1 UNII
    7XPB9B6MUA
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Ava6000

    2. Ava-6000

    3. Unii-7xpb9b6mua

    4. 1841402-73-0

    5. Schembl17345374

    2.4 Create Date
    2016-02-23
    3 Chemical and Physical Properties
    Molecular Weight 816.8 g/mol
    Molecular Formula C41H44N4O14
    XLogP31.9
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count15
    Rotatable Bond Count10
    Exact Mass Da
    Monoisotopic Mass Da
    Topological Polar Surface Area271
    Heavy Atom Count59
    Formal Charge0
    Complexity1630
    Isotope Atom Count0
    Defined Atom Stereocenter Count8
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
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