Namodenoson

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Also known as: 2-cl-ib-meca, 163042-96-4, Namodenoson, Cl-ib-meca, Cf-102, Cf102

Molecular Formula

C₁₈H₁₈ClIN₆O₄

Molecular Weight

544.7 g/mol

InChI Key

IPSYPUKKXMNCNQ-PFHKOEEOSA-N

FDA UNII

Z07JR07J6C

Namodenoson is an orally bioavailable, synthetic, highly selective adenosine A3 receptor (A3AR) agonist with potential antineoplastic activity. Namodenoson selectively binds to and activates the cell surface-expressed A3AR, deregulating Wnt and NF-kB signal transduction pathways downstream, which may result in apoptosis of A3AR-expressing tumor cells. A3AR, a G protein-coupled receptor, is highly expressed on the cell surfaces of various solid tumor cell types, including hepatocellular carcinoma (HCC) cells, and plays an important role in cellular proliferation.

1 2D Structure

Namodenoson

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3S,4R,5R)-5-[2-chloro-6-[(3-iodophenyl)methylamino]purin-9-yl]-3,4-dihydroxy-N-methyloxolane-2-carboxamide

2.1.2 InChI

InChI=1S/C18H18ClIN6O4/c1-21-16(29)13-11(27)12(28)17(30-13)26-7-23-10-14(24-18(19)25-15(10)26)22-6-8-3-2-4-9(20)5-8/h2-5,7,11-13,17,27-28H,6H2,1H3,(H,21,29)(H,22,24,25)/t11-,12+,13-,17+/m0/s1

2.1.3 InChI Key

IPSYPUKKXMNCNQ-PFHKOEEOSA-N

2.1.4 Canonical SMILES

CNC(=O)C1C(C(C(O1)N2C=NC3=C(N=C(N=C32)Cl)NCC4=CC(=CC=C4)I)O)O

2.1.5 Isomeric SMILES

CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=C(N=C32)Cl)NCC4=CC(=CC=C4)I)O)O

2.2 Other Identifiers

2.2.1 UNII

Z07JR07J6C

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-chloro-n(6)-(3-iodobenzyl)-9-(5-(methylcarbamoyl)-beta-d-ribofuranosyl)adenine

2. 2-chloro-n(6)-(3-iodobenzyl)adenosine-5'-n-methyluronamide

3. 2-chloro-n6-(3-iodobenzyl)adenosine-5'-n-methylcarboxamide

4. 2-cl-ib-meca

5. C-ibza-mu

6. Cf102 Compound

2.3.2 Depositor-Supplied Synonyms

1. 2-cl-ib-meca

2. 163042-96-4

3. Namodenoson

4. Cl-ib-meca

5. Cf-102

6. Cf102

7. C-ibza-mu

8. (2s,3s,4r,5r)-5-(2-chloro-6-((3-iodobenzyl)amino)-9h-purin-9-yl)-3,4-dihydroxy-n-methyltetrahydrofuran-2-carboxamide

9. Ci-ib-meca

10. 2-chloro-n(6)-(3-iodobenzyl)adenosine-5'-n-methyluronamide

11. Namodenoson [usan]

12. 2cl-ib-meca

13. (2s,3s,4r,5r)-5-[2-chloro-6-[(3-iodophenyl)methylamino]purin-9-yl]-3,4-dihydroxy-n-methyloxolane-2-carboxamide

14. Chembl431733

15. Z07jr07j6c

16. 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9h-purin-9-yl]-1-deoxy-n-methyl-beta-d-ribofuranuronamide

17. Unii-z07jr07j6c

18. 1-(2-chloro-6-(((3-iodophenyl)methyl)amino)-9h-purin-9-yl)-1-deoxy-n-methyl-beta-d-ribofuranuronamide

19. Beta-d-ribofuranuronamide, 1-(2-chloro-6-(((3-iodophenyl)methyl)amino)-9h-purin-9-yl)-1-deoxy-n-methyl-

20. Beta-d-ribofuranuronamide, 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9h-purin-9-yl]-1-deoxy-n-methyl-

21. Cf 102

22. 2-chloro-n6-(3-iodobenzyl)adenosine-5'-n-methylcarboxamide

23. Namodenoson [inn]

24. Namodenoson (cf-102)

25. Namodenoson (usan/inn)

26. C1-ib-meca

27. 2-chloro-n(6)-(3-iodobenzyl)-9-(5-(methylcarbamoyl)-beta-d-ribofuranosyl)adenine

28. Gtpl457

29. Namodenoson [who-dd]

30. Mls002153535

31. Schembl1170028

32. Bdbm21221

33. 2-chloro-n6-(3-iodobenzyl)adenosine-5'-n-methyluronamide

34. Cf-102;2-cl-ib-meca

35. Dtxsid80167504

36. Hms2235l10

37. Hms3412i05

38. Hms3676i05

39. Cf-102(2-cl-ib-meca)

40. Ex-a2882

41. Zinc3995845

42. Mfcd01861178

43. Akos022181265

44. Am84557

45. Cs-5932

46. Db12885

47. Ncgc00025001-02

48. Ac-27390

49. Ds-16397

50. Hy-12365

51. Smr001230862

52. Chloro-ib-meca, Solid, >=98% (hplc)

53. B6597

54. C3601

55. S0498

56. D11128

57. P10208

58. A848899

59. J-009992

60. Q27076097

61. 2-chloro-n6-(3-iodobenzyl)adenosine-5-n-methylcarboxamide

62. (2s,3s,4r,5r)-5-(2-chloro-6-(3-iodobenzylamino)-9h-purin-9-yl)-3,4-dihydroxy-n-methyltetrahydrofuran-2-carboxamide

63. (2s,3s,4r,5r)-5-(2-chloro-6-{[(3-iodophenyl)methyl]amino}-9h-purin-9-yl)-3,4-dihydroxy-n-methyloxolane-2-carboxamide

64. (2s,3s,4r,5r)-5-(6-(3-iodobenzylamino)-2-chloro-9h-purin-9-yl)-3,4-dihydroxy-n-methyl-tetrahydrofuran-2-carboxamide

65. .beta.-d-ribofuranuronamide, 1-(2-chloro-6-(((3-iodophenyl)methyl)amino)-9h-purin-9-yl)-1-deoxy-n-methyl-

66. 1-(2-chloro-6-(((3-iodophenyl)methyl)amino)-9h-purin-9-yl)-1-deoxy-n-methyl-.beta.-d-ribofuranuronamide

67. 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9h-purin-9-yl]-1-deoxy-n-methyl-?-d-ribofuranuronamide

68. 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9h-purin-9-yl]-1-deoxy-n-methyl-beta-d-ribofuranuronamide;2-chloro-n6-(3-iodobenzyl)adenosine-5'-n-methyluronamide;2-cl-ib-meca;2-cl-ib-meca

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₈ClIN₆O₄
Molecular Weight	544.7 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Exact Mass	544.01228 g/mol
Monoisotopic Mass	544.01228 g/mol
Topological Polar Surface Area	134 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	623
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1