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    Utidelone

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    2D Structure
    Also known as: 189453-10-9, Desoxyepothilone b, (-)-desoxyepothilone b, Kos-862, 12,13-desoxyepothilone b, (-)-epothilone d
    Molecular Formula
    C27H41NO5S
    Molecular Weight
    491.7  g/mol
    InChI Key
    XOZIUKBZLSUILX-GIQCAXHBSA-N
    FDA UNII
    T0358E0YUF
    microtubule-targeted antitumor agent; lacking the epoxide of epothilone B; may be equiv to epothilone D
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
    2.1.2 InChI
    InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22-,23-,25-/m0/s1
    2.1.3 InChI Key
    XOZIUKBZLSUILX-GIQCAXHBSA-N
    2.2 Other Identifiers
    2.2.1 UNII
    T0358E0YUF
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Desoxyepothilone B

    2. 12,13-desoxyepothilone B

    3. Depob Cpd

    4. Epothilon D

    5. Epothiolone D

    6. Epothilone B, Desoxy

    7. Kos 862

    8. Kos-862

    9. Kos862

    2.3.2 Depositor-Supplied Synonyms

    1. 189453-10-9

    2. Desoxyepothilone B

    3. (-)-desoxyepothilone B

    4. Kos-862

    5. 12,13-desoxyepothilone B

    6. (-)-epothilone D

    7. Epothilon D

    8. Nsc-703147

    9. Kos 862

    10. 12,13-deoxyepothilone B

    11. Epothiolone D

    12. Depob Cpd

    13. Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4s,7r,8s,9s,13z,16s)-

    14. Nsc 703147

    15. T0358e0yuf

    16. Epothilone B, Desoxy

    17. 12,13-desoxyepothilone B, Cis

    18. Kos862

    19. R1492

    20. Chebi:29579

    21. Dtxsid70880053

    22. Nsc703147

    23. (4s,7r,8s,9s,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

    24. Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-((1e)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (4s,7r,8s,9s,13z,16s)-

    25. (4s,7r,8s,9s,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-((e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl)-1-oxacyclohexadec-13-ene-2,6-dione

    26. Refchem:137339

    27. Dtxcid901022595

    28. (4s-(4r*,7s,8r*,9r*,13z,16r*(e)))-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-(1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)oxacyclohexadec-13-ene-2,6-dione

    29. R-1492

    30. Mfcd27976357

    31. (4s,7r,8s,9s,16s,z)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-((e)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)oxacyclohexadec-13-ene-2,6-dione

    32. Epothilone D (synthetic)

    33. (4s,7r,8s,9s,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(e)-1-methyl-2-(2-methylthiazol-4-yl)vinyl]-1-oxacyclohexadec-13-ene-2,6-dione

    34. Epd

    35. Unii-t0358e0yuf

    36. Utidelone

    37. Epothilone-d

    38. Depob

    39. Utidelone [inn]

    40. Epo D

    41. Epothilone D [mi]

    42. Schembl4415

    43. 12,13-desoxy-epothilone B

    44. Chembl96172

    45. Z-12,13-desoxyepothilone B

    46. Epothilone D [who-dd]

    47. C27h41no5s

    48. Orb1679023

    49. Ex-a495

    50. Glxc-06445

    51. Biologically Synthesized Epothilone D

    52. Lmpk04000001

    53. Nsc721085

    54. Akos025401598

    55. Cs-0655

    56. Db01873

    57. Fe22752

    58. Nsc-721085

    59. Ac-22616

    60. Hy-15278

    61. Brd-k52762805-001-01-2

    62. (4s,7r,8s,9s,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-(1e)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-oxacyclohexadec-13-ene-2,6-dione

    63. (4s,7r,8s,9s,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

    64. (4s,7r,8s,9s,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]oxacyclohexadec-13-ene-2,6-dione

    65. (4s,7r,8s,9s,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]oxacyclohexadec-13-ene- 2,6-dione

    66. (4s,7r,8s,9s,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]oxacyclohexadec-13-ene-2,6-dione; (-)-desoxyepothilone B; (-)-epothilone D; 12,13-deoxyepo

    67. (4s,7r,8s,9s,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(e)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxacyclohexadec-13-ene-2,6-dione

    68. (4s-(4r*,8r*,9r*,13z,16r*(e)))-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-(1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)oxacyclohexadec-13-ene-2,6-dione

    69. Oxacyclohexadec-13-ene-2,6-dione, 4,6-dihydroxy-5,5,7,9,13-pentamethyl-16-((1e)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (4s,7r,8s,9s,13z,16s)-

    70. Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-(1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (4s-(4r*,7s,8r*,9r*,13z,16r*(e)))-

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 491.7 g/mol
    Molecular Formula C27H41NO5S
    XLogP35
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count2
    Exact Mass Da
    Monoisotopic Mass Da
    Topological Polar Surface Area125
    Heavy Atom Count34
    Formal Charge0
    Complexity777
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count2
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in colorectal cancer, lung cancer, breast cancer, solid tumors, and prostate cancer.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Tubulin Modulators

    Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.

    5.2 ATC Code

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01D - Cytotoxic antibiotics and related substances

    L01DC - Other cytotoxic antibiotics

    L01DC05 - Utidelone

    ATCvet Code

    QL - Antineoplastic and immunomodulating agents

    QL01 - Antineoplastic agents

    QL01D - Cytotoxic antibiotics and related substances

    QL01DC - Other cytotoxic antibiotics

    QL01DC05 - Utidelone

    5.3 Mechanism of Action

    The principal mechanism of the epothilone class is inhibition of microtubule function. Microtubules are essential to cell division, and epothilones therefore stop cells from properly dividing.

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