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    Cordycepin

    PharmaCompass
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    2D Structure
    Also known as: 3'-deoxyadenosine, 73-03-0, Cordycepine, 9-cordyceposidoadenine, Adenosine, 3'-deoxy-, 9-(beta-d-3'-deoxyribofuranosyl)adenine
    Molecular Formula
    C10H13N5O3
    Molecular Weight
    251.24  g/mol
    InChI Key
    OFEZSBMBBKLLBJ-BAJZRUMYSA-N
    FDA UNII
    GZ8VF4M2J8
    Cordycepin is a purine nucleoside antimetabolite and antibiotic isolated from the fungus Cordyceps militaris with potential antineoplastic, antioxidant, and anti-inflammatory activities. Cordycepin is an inhibitor of polyadenylation, activates AMP-activated protein kinase (AMPK) and reduces mammalian target of rapamycin (mTOR) signaling, which may result in both the induction of tumor cell apoptosis and a decrease in tumor cell proliferation. mTOR, a serine/threonine kinase belonging to the phosphatidylinositol 3-kinase (PI3K)-related kinase (PIKK) family, plays an important role in the PI3K/AKT/mTOR signaling pathway that regulates cell growth and proliferation, and its expression or activity is frequently dysregulated in human cancers.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R,3R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
    2.1.2 InChI
    InChI=1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,10+/m0/s1
    2.1.3 InChI Key
    OFEZSBMBBKLLBJ-BAJZRUMYSA-N
    2.1.4 Canonical SMILES
    C1C(OC(C1O)N2C=NC3=C(N=CN=C32)N)CO
    2.1.5 Isomeric SMILES
    C1[C@H](O[C@H]([C@@H]1O)N2C=NC3=C(N=CN=C32)N)CO
    2.2 Other Identifiers
    2.2.1 UNII
    GZ8VF4M2J8
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3'-deoxyadenosine

    2. 9-cordyceposidoadenine

    3. Cordycepene

    4. Cordycepine

    2.3.2 Depositor-Supplied Synonyms

    1. 3'-deoxyadenosine

    2. 73-03-0

    3. Cordycepine

    4. 9-cordyceposidoadenine

    5. Adenosine, 3'-deoxy-

    6. 9-(beta-d-3'-deoxyribofuranosyl)adenine

    7. 9h-purine, 6-amino-9-(3-deoxy-beta-d-ribofuranosyl)-

    8. Nsc 401022

    9. Brn 0035194

    10. (2r,3r,5s)-2-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol

    11. Gz8vf4m2j8

    12. Chembl305686

    13. Chebi:29014

    14. Nsc-63984

    15. Nsc-401022

    16. Nsc 627047

    17. 9-(3-deoxy-b-d-erythro-pentofuranosyl)-9h-purin-6-amine

    18. Mfcd00037998

    19. (2r,3r,5s)-2-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol

    20. 3ad

    21. Smr000058644

    22. Ccris 3233

    23. Einecs 200-791-4

    24. Unii-gz8vf4m2j8

    25. Nsc627047

    26. Cordycepin,(s)

    27. Cordyceps 7%

    28. 3''-deoxyadenosine

    29. 3'-deoxy-adenosine

    30. Beta-d-erythro-pentofuranoside, Adenine-9 3-deoxy-

    31. Adenine Cordyceposide

    32. Starbld0009677

    33. 9-cordyceposidoadenosine

    34. Cordycepin [mi]

    35. 9h-purin-6-amine, 9-(3-deoxy-beta-d-erythro-pentofuranosyl)-

    36. Cordycepin [inci]

    37. 2'-oh-3'-da Erythro

    38. Schembl98323

    39. 2-(6-aminopurin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol

    40. 4-26-00-03594 (beilstein Handbook Reference)

    41. Mls001066343

    42. Mls006012047

    43. Amot0014

    44. Gtpl4630

    45. Dtxsid1041007

    46. Tcmdc-143080

    47. Hms2234e22

    48. Hms3413c16

    49. Hms3677c16

    50. Cordycepin, >=98.0% (hplc)

    51. Hy-n0262

    52. Zinc1319796

    53. Cordycepin, From Cordyceps Militaris

    54. (2r,3r,5s)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol

    55. Bdbm50144950

    56. Nsc 63984

    57. Pdsp1_001033

    58. Pdsp2_001017

    59. S3610

    60. (2r,3r,5s)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol

    61. 2'-hydroxy-3'-deoxyadenosine Erythro

    62. Akos015854875

    63. Akos015902254

    64. Am85418

    65. Ccg-266973

    66. Cs-w009017

    67. Db12156

    68. Ncgc00092360-03

    69. Ac-22613

    70. As-11189

    71. 9-(beta-d-3''-deoxyribofuranosyl)adenine

    72. N2808

    73. C08431

    74. 037c998

    75. A837698

    76. 9-(3-deoxy-.beta.-d-ribofuranosyl)adenine

    77. Q2256677

    78. Ncgc00092360-03_c10h13n5o3_3'-deoxyadenosine

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 251.24 g/mol
    Molecular Formula C10H13N5O3
    XLogP3-1.2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count2
    Exact Mass251.10183929 g/mol
    Monoisotopic Mass251.10183929 g/mol
    Topological Polar Surface Area119 Ų
    Heavy Atom Count18
    Formal Charge0
    Complexity307
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    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

    Antineoplastic Agents

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

    Mutagens

    Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. (See all compounds classified as Mutagens.)

    Antifungal Agents

    Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)