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    CAS-63358-49-6

    PharmaCompass
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    2D Structure
    Also known as: 63358-49-6, Aspoxicillan, Aspoxicilina, Aspoxicilline, Aspoxicillinum, Aspc
    Molecular Formula
    C21H27N5O7S
    Molecular Weight
    493.5  g/mol
    InChI Key
    BHELIUBJHYAEDK-OAIUPTLZSA-N
    FDA UNII
    0745KNO26J
    Aspoxicillin is a broad-spectrum, semisynthetic penicillin derivative with antibacterial activity. Aspoxicillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall, eventually causing cell lysis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,5R,6R)-6-[[(2R)-2-[[(2R)-2-amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C21H27N5O7S/c1-21(2)15(20(32)33)26-18(31)14(19(26)34-21)25-17(30)13(9-4-6-10(27)7-5-9)24-16(29)11(22)8-12(28)23-3/h4-7,11,13-15,19,27H,8,22H2,1-3H3,(H,23,28)(H,24,29)(H,25,30)(H,32,33)/t11-,13-,14-,15+,19-/m1/s1
    2.1.3 InChI Key
    BHELIUBJHYAEDK-OAIUPTLZSA-N
    2.1.4 Canonical SMILES
    CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)NC(=O)C(CC(=O)NC)N)C(=O)O)C
    2.1.5 Isomeric SMILES
    CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)NC(=O)[C@@H](CC(=O)NC)N)C(=O)O)C
    2.2 Other Identifiers
    2.2.1 UNII
    0745KNO26J
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. N(4)-methyl-d-asparaginylamoxicillin

    2. Ta 058

    3. Ta-058

    2.3.2 Depositor-Supplied Synonyms

    1. 63358-49-6

    2. Aspoxicillan

    3. Aspoxicilina

    4. Aspoxicilline

    5. Aspoxicillinum

    6. Aspc

    7. Doyle

    8. Doyle (tn)

    9. (2s,5r,6r)-6-[[(2r)-2-[[(2r)-2-amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    10. Chebi:31240

    11. 0745kno26j

    12. Ncgc00181352-01

    13. (2s,5r,6r)-6-((2r)-2-((2r)-2-amino-3-(methylcarbamoyl)propionamido)-2-(p-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid

    14. Aspoxicilina [spanish]

    15. Aspoxicilline [french]

    16. Aspoxicillinum [latin]

    17. Aspoxicillin [inn:jan]

    18. Ta 058

    19. Ccris 2514

    20. Unii-0745kno26j

    21. N(sup 4)-methyl-d-asparagininylamoxicillin

    22. Aspoxicillin (jan/inn)

    23. Aspoxicillin [mi]

    24. Aspoxicillin [inn]

    25. Dsstox_cid_26921

    26. Dsstox_rid_82017

    27. Dsstox_gsid_46921

    28. Schembl34176

    29. Aspoxicillin [mart.]

    30. Aspoxicillin [who-dd]

    31. Chembl1318150

    32. Dtxsid6046921

    33. Zinc3871610

    34. Tox21_112810

    35. Db13816

    36. Glycinamide, N-methyl-d-asparaginyl-n-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-d-2-(4-hydroxyphenyl)-, (2s-(2-alpha,5-alpha,6-beta))-

    37. Cas-63358-49-6

    38. Hy-135842

    39. Cs-0114376

    40. D07469

    41. Q27114235

    42. (2s,5r,6r)-6-[[(2r)-2-[[(2r)-2-amino-4-(methylamino)-4-oxo-butanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    43. (2s,5r,6r)-6-[[(2r)-2-[[(2r)-2-amino-4-methylamino-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 493.5 g/mol
    Molecular Formula C21H27N5O7S
    XLogP3-3.4
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count8
    Exact Mass493.16311939 g/mol
    Monoisotopic Mass493.16311939 g/mol
    Topological Polar Surface Area217 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity861
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01C - Beta-lactam antibacterials, penicillins

    J01CA - Penicillins with extended spectrum

    J01CA19 - Aspoxicillin