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    Also known as: Pirarubicin, 72496-41-4, Pinorubicin, Pinorubin, Pirarubicin, >=95% (hplc), (7s,9s)-7-[(2r,4s,5s,6s)-4-amino-6-methyl-5-(oxan-2-yloxy)oxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione
    Molecular Formula
    C32H37NO12
    Molecular Weight
    627.6  g/mol
    InChI Key
    KMSKQZKKOZQFFG-NCXNULAVSA-N
    Therarubicin Tn
    Pirarubicin is an analogue of the anthracycline antineoplastic antibiotic doxorubicin. Pirarubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. This agent is less cardiotoxic than doxorubicin and exhibits activity against some doxorubicin-resistant cell lines. (NCI04)
    1 2D Structure

    Therarubicin Tn

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-(oxan-2-yloxy)oxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
    2.1.2 InChI
    InChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21?,22-,31+,32-/m0/s1
    2.1.3 InChI Key
    KMSKQZKKOZQFFG-NCXNULAVSA-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(=O)CO)O)N)OC6CCCCO6
    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(=O)CO)O)N)OC6CCCCO6
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. 4'-o-tetrahydropyranyladriamycin

    2. 4'-o-tetrahydropyranyldoxorubicin

    3. 4'-o-tetrapyranyldoxorubicin

    4. Pirarubicin

    5. Pirarubicin Hydrochloride

    6. Thprubicine

    7. Thepirubicin

    8. Theprubicin

    9. Thp-adm

    10. Thp-adriamycin

    11. Thp-dox

    12. Thp-doxorubicin

    2.2.2 Depositor-Supplied Synonyms

    1. Pirarubicin

    2. 72496-41-4

    3. Pinorubicin

    4. Pinorubin

    5. Pirarubicin, >=95% (hplc)

    6. (7s,9s)-7-[(2r,4s,5s,6s)-4-amino-6-methyl-5-(oxan-2-yloxy)oxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione

    7. Sr-01000944915

    8. Sr-01000944915-1

    2.3 Create Date
    2006-07-28
    3 Chemical and Physical Properties
    Molecular Weight 627.6 g/mol
    Molecular Formula C32H37NO12
    XLogP32.7
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count7
    Exact Mass627.23157562 g/mol
    Monoisotopic Mass627.23157562 g/mol
    Topological Polar Surface Area204 Ų
    Heavy Atom Count45
    Formal Charge0
    Complexity1120
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    4.2 ATC Code

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01D - Cytotoxic antibiotics and related substances

    L01DB - Anthracyclines and related substances

    L01DB08 - Pirarubicin

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