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    Technical details about Tigilanol Tiglate, learn more about the structure, uses, toxicity, action, side effects and more

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    Tigilanol Tiglate

    APIs // Active Pharmaceutical Ingredients

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    DIGITAL CONTENT

    PharmaCompass

    Inke S.A: APIs manufacturing plant.

    ChemWerth works in generic API development & supply, non-infringement patent strategy development and regulatory support.

    2D Structure
    1. Also known as: Ebc-46, Ebi-46, Tigilanol tiglate [usan], 943001-56-7, R1zjt87990, 12-tigloyl-13-(2-methylbutanoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tiglian-3-one
    Molecular Formula
    C30H42O10
    Molecular Weight
    562.6  g/mol
    InChI Key
    YLQZMOUMDYVSQR-FOWZUWBHSA-N
    FDA UNII
    R1ZJT87990
    Tigilanol Tiglate is a short-chain diterpene ester isolated from the seed of Fontainea picrosperma, with potential antineoplastic activity. Upon intratumoral administration, tigilanol tiglate disrupts mitochondrial functioning and induces mitochondrial swelling, which leads to oncolysis of tumor cells that are in direct contact of the agent. In addition, tigilanol tiglate activates protein kinase C (PKC) signaling cascade, which leads to an acute inflammatory response. This results in hypoxia and activates innate immune cells including neutrophils and macrophages, thereby further killing tumor cells. The activation of the beta-II isoform of PKC (PKC beta II ) also increases tumor vasculature permeability, which leads to the destruction of tumor vasculature.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(1R,2S,4R,5S,6S,10S,11R,12R,13R,14S,16R)-5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-[(E)-2-methylbut-2-enoyl]oxy-7-oxo-3-oxapentacyclo[9.5.0.02,4.06,10.014,16]hexadec-8-en-14-yl] (2S)-2-methylbutanoate
    2.1.2 InChI
    InChI=1S/C30H42O10/c1-9-13(3)23(33)38-21-16(6)28(36)17-11-15(5)20(32)29(17,37)25(35)27(12-31)22(39-27)18(28)19-26(7,8)30(19,21)40-24(34)14(4)10-2/h9,11,14,16-19,21-22,25,31,35-37H,10,12H2,1-8H3/b13-9+/t14-,16+,17-,18+,19+,21+,22-,25+,27-,28-,29+,30+/m0/s1
    2.1.3 InChI Key
    YLQZMOUMDYVSQR-FOWZUWBHSA-N
    2.1.4 Canonical SMILES
    CCC(C)C(=O)OC12C(C1(C)C)C3C4C(O4)(C(C5(C(C3(C(C2OC(=O)C(=CC)C)C)O)C=C(C5=O)C)O)O)CO
    2.1.5 Isomeric SMILES
    CC[C@H](C)C(=O)O[C@@]12[C@@H](C1(C)C)[C@@H]3[C@H]4[C@](O4)([C@H]([C@]5([C@H]([C@]3([C@@H]([C@H]2OC(=O)/C(=C/C)/C)C)O)C=C(C5=O)C)O)O)CO
    2.2 Other Identifiers
    2.2.1 UNII
    R1ZJT87990
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 12-tigloyl-13-(2-methylbutanoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tigliaen-3-one

    2. Ebc-46

    2.3.2 Depositor-Supplied Synonyms

    1. Ebc-46

    2. Ebi-46

    3. Tigilanol Tiglate [usan]

    4. 943001-56-7

    5. R1zjt87990

    6. 12-tigloyl-13-(2-methylbutanoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tiglian-3-one

    7. (4s,5s,6r,7s,8r,9r,10s,11r,12r,13s,14r)-12-(2e)-2-methyl-2-enoatyl-13((2s)-2-methylbutyroyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tigliaen-3-one

    8. Unii-r1zjt87990

    9. Tigilanol Tiglate [mi]

    10. Tigilanol Tiglate (usan/inn)

    11. Tigilanol Tiglate [inn]

    12. Chembl3989916

    13. Dtxsid601029530

    14. Tigilanol Tiglate [who-dd]

    15. D11191

    16. (1ar,1br,1cs,2ar,3s,3as,6as,6br,7r,8r,8as)-3,3a,6b-trihydroxy-2a-(hydroxymethyl)-1,1,5,7-tetramethyl-4-oxo-1,1a,1b,1c,2a,3,3a,4,6a,6b,7,8-dodecahydro-8ah-cyclopropa(5',6')benzo(1',2':7,8)azuleno(5,6-b)oxirene-8,8a-diyl 8a-((2s)-2-methylbutanoate) 8-((2e)-2-methylbut-2-enoate)

    2.4 Create Date
    2015-12-04
    3 Chemical and Physical Properties
    Molecular Weight 562.6 g/mol
    Molecular Formula C30H42O10
    XLogP32.1
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count8
    Exact Mass562.27779753 g/mol
    Monoisotopic Mass562.27779753 g/mol
    Topological Polar Surface Area163 Ų
    Heavy Atom Count40
    Formal Charge0
    Complexity1220
    Isotope Atom Count0
    Defined Atom Stereocenter Count12
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of non-resectable, non-metastatic (WHO staging) subcutaneous mast cell tumours located at or distal to the elbow or the hock, and non-resectable, non metastatic cutaneous mast cell tumours in dogs.

    5 Pharmacology and Biochemistry
    5.1 ATC Code

    QL01XX

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