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    Aclarubicin

    DEVELOPMENTS

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    2D Structure
    Also known as: Aclacinomycin a, 57576-44-0, Aclarubicine, Aclarubicinum, Aclarubicina, Nsc-208734
    Molecular Formula
    C42H53NO15
    Molecular Weight
    811.9  g/mol
    InChI Key
    USZYSDMBJDPRIF-SVEJIMAYSA-N
    FDA UNII
    74KXF8I502
    An anthracycline produced by Streptomyces galilaeus. It has potent antineoplastic activity.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    methyl (1R,2R,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
    2.1.2 InChI
    InChI=1S/C42H53NO15/c1-8-42(51)17-28(33-22(35(42)41(50)52-7)14-23-34(38(33)49)37(48)32-21(36(23)47)10-9-11-26(32)45)56-30-15-24(43(5)6)39(19(3)54-30)58-31-16-27(46)40(20(4)55-31)57-29-13-12-25(44)18(2)53-29/h9-11,14,18-20,24,27-31,35,39-40,45-46,49,51H,8,12-13,15-17H2,1-7H3/t18-,19-,20-,24-,27-,28-,29-,30-,31-,35-,39+,40+,42+/m0/s1
    2.1.3 InChI Key
    USZYSDMBJDPRIF-SVEJIMAYSA-N
    2.2 Other Identifiers
    2.2.1 UNII
    74KXF8I502
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Aclacinomycin A

    2. Nsc-208734

    2.3.2 Depositor-Supplied Synonyms

    1. Aclacinomycin A

    2. 57576-44-0

    3. Aclarubicine

    4. Aclarubicinum

    5. Aclarubicina

    6. Nsc-208734

    7. Ma 144-a1

    8. 74kxf8i502

    9. Chebi:74619

    10. Nsc 208734

    11. Methyl (1r,2r,4s)-4-[(2r,4s,5s,6s)-4-(dimethylamino)-5-[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate

    12. Nsc208734

    13. 1-naphthacenecarboxylic Acid,(2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-((2,3,6-trideoxy-4-o-(2,6-dideoxy-4-o-((2r-trans)-tetrahydro-6-methyl-5-oxo-2h-pyran-2-yl)-alpha-l-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-l-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-l-lyxo-hexopyranosyl)oxy)-, Methyl Ester, (1r-(1alpha,2beta,4beta))-

    14. Antibiotic Ma144-a1

    15. Aclacinomycin-a

    16. Nsc240619

    17. Methyl (1r,2r,4s)-4-((2r,4s,5s,6s)-4-(dimethylamino)-5-((2s,4s,5s,6s)-4-hydroxy-6-methyl-5-((2r,6s)-6-methyl-5-oxooxan-2-yl)oxyoxan-2-yl)oxy-6-methyloxan-2-yl)oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate

    18. Acm-a

    19. Refchem:915045

    20. Glytoucan:g42541yc

    21. L01db04

    22. Ma144a1

    23. G42541yc

    24. Ma 144a1

    25. Ma144-a1

    26. (1r,2r,4s)-2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-((2,3,6-trideoxy-4-o-(2,6-dideoxy-4-o-((2r,trans)-tetrahydro-6-methyl-5-oxo-2h-pyran-2-yl)-alpha-l-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-l-lyxo-hexopyranosyl)oxy)-1-naphthacenecarboxylic Acid Methyl Ester

    27. (1r,2r,4s)-4-((2r,4s,5s,6s)-4-(dimethylazaniumyl)-5-((2s,4s,5s,6s)-4-hydroxy-6-methyl-5-((2r,6s)-6-methyl-5-oxooxan-2-yl)oxyoxan-2-yl)oxy-6-methyloxan-2-yl)oxy-2-ethyl-2,7-dihydroxy-1-methoxycarbonyl-6,11-dioxo-3,4-dihydro-1h-tetracen-5-olate

    28. 1-naphthacenecarboxylic Acid, 2-ethyl-1,2,3,4,6,11-hexahydro-2,5, 7-trihydroxy-6,11-dioxo-4-((2,3,6-trideoxy-4-o-(2,6-dideoxy-4-o-((2r-trans)-tetrahydro-6-methyl-5-oxo-2h-pyran-2-yl)-alpha-l-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-l-lyxo-hexopyranosyl)oxy)-, Methyl Ester,(1r-(1alpha,2beta,4beta))-

    29. 260-824-3

    30. Aclacur

    31. Antibiotic Ma 144a1

    32. Aclarubicino

    33. Aclacinomycin A1

    34. Methyl (1r,2r,4s)-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-4-{[2,3,6-trideoxy-4-o-{2,6-dideoxy-4-o-[(2r,6s)-6-methyl-5-oxotetrahydro-2h-pyran-2-yl]-alpha-l-lyxo-hexopyranosyl}-3-(dimethylamino)-alpha-l-lyxo-hexopyranosyl]oxy}-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

    35. Methyl (1r,2r,4s)-4-[(2r,4s,5s,6s)-4-(dimethylamino)-5-[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-[(2r,6s)-6-methyl-5-oxo-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-6-methyl-tetrahydropyran-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate

    36. Antibiotic Ma 144a

    37. Aclarubicine [inn-french]

    38. Aclarubicinum [inn-latin]

    39. Aclarubicino [inn-spanish]

    40. Aclarubicins

    41. C42h53no15

    42. Unii-74kxf8i502

    43. Aclarubicin [usan:inn:ban]

    44. Ccris 2262

    45. Mfcd00866250

    46. Einecs 260-824-3

    47. Spectrum_000467

    48. Spectrum2_001934

    49. Spectrum4_000768

    50. Spectrum5_001041

    51. Aclarubicin [inn]

    52. Aclarubicin [jan]

    53. Aclarubicin (usan/inn)

    54. Aclarubicin [usan]

    55. Aclacinomycin A (standard)

    56. Schembl4532

    57. Aclarubicin [mart.]

    58. Aclacinomycin A [mi]

    59. Aclarubicin [who-dd]

    60. Kbiogr_001156

    61. Kbioss_000947

    62. Spbio_001967

    63. Chembl502620

    64. Orb2276869

    65. Dtxsid1022554

    66. Schembl29390785

    67. Hy-n2306r

    68. Kbio2_000947

    69. Kbio2_003515

    70. Kbio2_006083

    71. Glxc-23058

    72. Hms2089b13

    73. Hy-n2306

    74. Aw8655

    75. Bdbm50368351

    76. Ccg-39864

    77. Aa08264

    78. Db11617

    79. Methyl (1r,2r,4s)-2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-((2,3,6-trideoxy-4-o-(2,6-dideoxy-4-o-((2r,6s)-tetrahydro-6-methyl-5-oxo-2h-pyran-2-yl)-alpha-l-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-l-lyxo-hexopyranosyl)oxy)-1-naphthacenecarboxylate

    80. Cs-0020062

    81. Ns00003246

    82. C18638

    83. D02756

    84. Ab00052311-02

    85. Q4674302

    86. 1-naphthacenecarboxylic Acid, 2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-((2,3,6-trideoxy-4-o-(2,6-dideoxy-4-o-((2r-trans)-tetrahydro-6-methyl-5-oxo-2h-pyran-2-yl)-alpha-l-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-l-lyxo-hexopyranosyl)oxy)-, Methyl Ester, (1r-(1alpha,2beta,4beta))-

    87. 2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-[[2,3,6-trideoxy-4-o-[2,6-dideoxy-4-o-[(2r-trans)-tetrahydro-6-methyl-5-oxo-2h-pyran-2-yl]-.alpha.-l-lyxo-hexopyranosyl]-3-(dimethylamino)-.alpha.-l-lyxo-hexopyranosyl]-oxy]-1-naphthacenecarboxalic Acid Methyl Ester

    88. Methyl (1r,2r,4s)-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-4-{[2,3,6-trideoxy-4-o-{2,6-dideoxy-4-o-[(2r,6s)-6-methyl-5-oxooxan-2-yl]-alpha-l-lyxo-hexopyranosyl}-3-(dimethylamino)-alpha-l-lyxo-hexopyranosyl]oxy}-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

    2.4 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 811.9 g/mol
    Molecular Formula C42H53NO15
    XLogP33.8
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count16
    Rotatable Bond Count10
    Exact Mass Da
    Monoisotopic Mass Da
    Topological Polar Surface Area217
    Heavy Atom Count58
    Formal Charge0
    Complexity1530
    Isotope Atom Count0
    Defined Atom Stereocenter Count13
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Antibiotics, Antineoplastic

    Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.

    Topoisomerase II Inhibitors

    Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II.

    4.2 ATC Code

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01D - Cytotoxic antibiotics and related substances

    L01DB - Anthracyclines and related substances

    L01DB04 - Aclarubicin

    ATCvet Code

    QL - Antineoplastic and immunomodulating agents

    QL01 - Antineoplastic agents

    QL01D - Cytotoxic antibiotics and related substances

    QL01DB - Anthracyclines and related substances

    QL01DB04 - Aclarubicin

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