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    Berubicin

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 677017-23-1, Wp 769, Berubicin [inn], 6qpn83hk2m, (7s,9s)-7-[(2r,4s,5s,6s)-4-amino-6-methyl-5-phenylmethoxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione, Unii-6qpn83hk2m
    Molecular Formula
    C34H35NO11
    Molecular Weight
    633.6  g/mol
    InChI Key
    FIGNGSHKNAHTSH-JJMFXPFOSA-N
    FDA UNII
    6QPN83HK2M
    Berubicin is a 4'-O-benzylated analogue of the anthracycline derivative doxorubicin, with potential antineoplastic activity. Berubicin intercalates into DNA and interrupts topoisomerase II activity, resulting in the inhibition of DNA replication and repair, as well as RNA and protein synthesis. Unlike other anthracycline derivatives, this agent crosses the blood-brain barrier (BBB) and can circumvent P glycoprotein/MRP1-mediated efflux.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-phenylmethoxyoxan-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/C34H35NO11/c1-16-33(44-15-17-7-4-3-5-8-17)20(35)11-24(45-16)46-22-13-34(42,23(37)14-36)12-19-26(22)32(41)28-27(30(19)39)29(38)18-9-6-10-21(43-2)25(18)31(28)40/h3-10,16,20,22,24,33,36,39,41-42H,11-15,35H2,1-2H3/t16-,20-,22-,24-,33+,34-/m0/s1
    2.1.3 InChI Key
    FIGNGSHKNAHTSH-JJMFXPFOSA-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)OCC6=CC=CC=C6
    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)OCC6=CC=CC=C6
    2.2 Other Identifiers
    2.2.1 UNII
    6QPN83HK2M
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 677017-23-1

    2. Wp 769

    3. Berubicin [inn]

    4. 6qpn83hk2m

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

    6. Unii-6qpn83hk2m

    7. Wp-769

    8. Berubicin [who-dd]

    9. Chembl2110580

    10. Dtxsid70217986

    11. Zinc72267022

    12. Bb178714

    13. Q27265347

    14. (8s,10s)-10-((3-amino-4-o-benzyl-2,3,6-trideoxy-a-l-lyxo-hexopyranosyl)oxy)-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione

    15. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-4-o-(phenylmethyl)-.alpha.-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8s,10s)-

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 633.6 g/mol
    Molecular Formula C34H35NO11
    XLogP33.3
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count8
    Exact Mass633.22101093 g/mol
    Monoisotopic Mass633.22101093 g/mol
    Topological Polar Surface Area195 Ų
    Heavy Atom Count46
    Formal Charge0
    Complexity1130
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1