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    Distamycin A

    ACTIVE PHARMA INGREDIENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: Distamycin a, Distamycin, 636-47-5, Herperetin, Stallimycin [inn], Dst-a
    Molecular Formula
    C22H27N9O4
    Molecular Weight
    481.5  g/mol
    InChI Key
    UPBAOYRENQEPJO-UHFFFAOYSA-N
    FDA UNII
    80O63P88IS
    Stallimycin is an oligopeptide antineoplastic antibiotic isolated from the bacterium Streptomyces distallicus. Distamycin preferentially binds to adenine-thymine (A-T) rich sequences in the minor groove of DNA, thereby inhibiting DNA replication and RNA transcription. In addition to antitumor effects, distamycin also possesses antiviral and antiprotozoal activities and is used as a chromosome dye. (NCI04)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[5-[[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-formamido-1-methylpyrrole-2-carboxamide
    2.1.2 InChI
    InChI=1S/C22H27N9O4/c1-29-9-13(26-12-32)6-17(29)21(34)28-15-8-18(31(3)11-15)22(35)27-14-7-16(30(2)10-14)20(33)25-5-4-19(23)24/h6-12H,4-5H2,1-3H3,(H3,23,24)(H,25,33)(H,26,32)(H,27,35)(H,28,34)
    2.1.3 InChI Key
    UPBAOYRENQEPJO-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1C=C(C=C1C(=O)NC2=CN(C(=C2)C(=O)NC3=CN(C(=C3)C(=O)NCCC(=N)N)C)C)NC=O
    2.2 Other Identifiers
    2.2.1 UNII
    80O63P88IS
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Distamycin

    2. Distamycin A

    3. Stallimycin Hydrochloride

    4. Stallimycin Monohydrochloride

    2.3.2 Depositor-Supplied Synonyms

    1. Distamycin A

    2. Distamycin

    3. 636-47-5

    4. Herperetin

    5. Stallimycin [inn]

    6. Dst-a

    7. Nsc82150

    8. Nsc-82150

    9. Fi 6426

    10. Chembl11252

    11. 80o63p88is

    12. N-[5-[[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-formamido-1-methylpyrrole-2-carboxamide

    13. Ncgc00018292-04

    14. Distamycin 3

    15. Nsc 150528

    16. Estalimicina

    17. Stallimicina

    18. Stallimycine

    19. Stallimycinum

    20. Distamicina A

    21. Distamycin Hydrochloride

    22. 1h-pyrrole-2-carboxamide, N-(5-(((3-amino-3-iminopropyl)amino)carbonyl)-1-methyl-1h-pyrrol-3-yl)-4-(((4-(formylamino)-1-methyl-1h-pyrrol-2-yl)carbonyl)amino)-1-methyl-

    23. 1h-pyrrole-2-carboxamide, N-[5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1h-pyrrol-3-yl]-4-[[[4-(formylamino)-1-methyl-1h-pyrrol-2-yl]carbonyl]amino]-1-methyl-

    24. Nsc150528

    25. Stallimicina [dcit]

    26. Distamicina A [italian]

    27. Stallimycine [inn-french]

    28. Stallimycinum [inn-latin]

    29. Estalimicina [inn-spanish]

    30. Unii-80o63p88is

    31. Nsc 82150

    32. Brn 0468437

    33. Dst-3

    34. Distamycin A [mi]

    35. Dsstox_cid_25637

    36. Dsstox_rid_81018

    37. Dsstox_gsid_45637

    38. Distamycin; Stallimycin

    39. Schembl108585

    40. Dtxsid9045637

    41. Cid_6602691

    42. Zinc3872327

    43. Tox21_110857

    44. Bdbm50055659

    45. Ccg-36393

    46. N''-(2-amidinoethyl)-4-formamido-1,1',1''-trimethyl-n-4':n'-4''-ter-(2-pyrrolcarboxamid)

    47. Ncgc00018292-01

    48. Ncgc00018292-02

    49. Ncgc00018292-03

    50. Ncgc00018292-05

    51. Ncgc00024382-03

    52. Cas-636-47-5

    53. Nci60_041805

    54. Sr-01000000269

    55. Sr-01000000269-3

    56. Q27269162

    57. N,4''-ter[pyrrole-2-carboxamide], N''-(2-amidinoethyl)-4-formamido-1,1',1''-trimethyl-

    58. (n,4':n',4''-terpyrrole)-2-carboxamide, N''-(2-amidinoethyl)-4-formamido-1,1',1''-trimethyl-

    59. 2n-(3,3-aminoiminopropyl)-4-[4-(4-formamido-1-methyl-1h-2-pyrrolylcarboxamido)-1-methyl-1h-2-pyrrolylcarboxamido]-1-methyl-1h-2-pyrrolecarboxamide

    60. 2n-[5-(3-amino-3-iminopropylcarbamoyl)-1-methyl-1h-3-pyrrolyl]-4-(4-formamido-1-methyl-1h-2-pyrrolylcarboxamido)-1-methyl-1h-2-pyrrolecarboxamide

    61. 2n-[5-(3-amino-3-iminopropylcarbamoyl)-1-methyl-1h-3-pyrrolyl]-4-(4-formamido-1-methyl-1h-2-pyrrolylcarboxamido)-1-methyl-1h-2-pyrrolecarboxamide(distamycin A)

    62. 2n-[5-(3-amino-3-iminopropylcarbamoyl)-1-methyl-1h-3-pyrrolyl]-4-(4-formamido-1-methyl-1h-2-pyrrolylcarboxamido)-1-methyl-1h-2-pyrrolecarboxamide(distamycin)

    63. 39389-47-4

    64. 4n-[5-(3-amino-3-iminopropylcarbamoyl)-1-methyl-1h-2-pyrrolyl]-2-(4-formamido-1-methyl-1h-2-pyrrolylcarboxamido)-1-methyl-1h-4-pyrrolecarboxamide

    65. 5n-[5-(3-amino-3-iminopropylcarbamoyl)-1-methyl-2,3-dihydro-1h-3-pyrrolyl]-3-(4-formamido-1-methyl-1h-2-pyrrolylcarboxamido)-1-methyl-2,3-dihydro-1h-5-pyrrolecarboxamide

    66. N''-(2-amidinoethyl)-4-formamido-1,1',1''-trimethyl-n,4':n',4''-ter(pyrrole-2-carboxamide)

    67. N-(3-amino-3-iminopropyl)-4-(4-(4-formamido-1-methyl-1h-pyrrole-2-carboxamido)-1-methyl-1h-pyrrole-2-carboxamido)-1-methyl-1h-pyrrole-2-carboxamide

    68. N-[5-({5-[(3-amino-3-iminopropyl)carbamoyl]-1-methyl-1h-pyrrol-3-yl}carbamoyl)-1-methyl-1h-pyrrol-3-yl]-4-(formylamino)-1-methyl-1h-pyrrole-2-carboxamide

    69. N-[5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1h-pyrrol-3-yl]-4-[[[4-(formylamino)-methyl-1h-pyrrol-2-yl]carbonyl]amino]-1h-pyrrole-2-carboxamide

    70. N-[5-[[(amino-3-iminopropyl)amino]carbonyl]-1-methyl-1h-pyrrol-3-yl-4-[[(4-(formylamino)-1-methyl-1h-pyrrol-2yl]carbonyl]amino]-1h-pyrrole-2-carboxamide

    71. N-[5-[[5-[(3-amino-3-imino-propyl)carbamoyl]-1-methyl-pyrrol-3-yl]carbamoyl]-1-methyl-pyrrol-3-yl]-4-formamido-1-methyl-pyrrole-2-carboxamide

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 481.5 g/mol
    Molecular Formula C22H27N9O4
    XLogP3-1.8
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count9
    Exact Mass481.21860038 g/mol
    Monoisotopic Mass481.21860038 g/mol
    Topological Polar Surface Area181 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity825
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    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

    Antiviral Agents

    Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)