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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

Cordycepin

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 Formula	C₁₀H₁₃N₅O₃
Molecular Weight	251.24 g/mol
XLogP3	-1.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Exact Mass	251.10183929 g/mol
Monoisotopic Mass	251.10183929 g/mol
Topological Polar Surface Area	119 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	307
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.)

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