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Chemistry

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Also known as: Pgd2, 41598-07-6, 11-dehydroprostaglandin f2-alpha, 11-dehydroprostaglandin f2alpha, Brn 2170623, (5z,13e,15s)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
Molecular Formula
C20H32O5
Molecular Weight
352.5  g/mol
InChI Key
BHMBVRSPMRCCGG-OUTUXVNYSA-N
FDA UNII
RXY07S6CZ2

Prostaglandin D2
The principal cyclooxygenase metabolite of arachidonic acid. It is released upon activation of mast cells and is also synthesized by alveolar macrophages. Among its many biological actions, the most important are its bronchoconstrictor, platelet-activating-factor-inhibitory, and cytotoxic effects.
1 2D Structure

Prostaglandin D2

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-3-oxocyclopentyl]hept-5-enoic acid
2.1.2 InChI
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1
2.1.3 InChI Key
BHMBVRSPMRCCGG-OUTUXVNYSA-N
2.1.4 Canonical SMILES
CCCCCC(C=CC1C(C(CC1=O)O)CC=CCCCC(=O)O)O
2.1.5 Isomeric SMILES
CCCCC[C@@H](/C=C/[C@@H]1[C@H]([C@H](CC1=O)O)C/C=C\CCCC(=O)O)O
2.2 Other Identifiers
2.2.1 UNII
RXY07S6CZ2
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 11 Dehydroprostaglandin F2 Alpha

2. 11 Dehydroprostaglandin F2alpha

3. 11-dehydroprostaglandin F2 Alpha

4. 11-dehydroprostaglandin F2alpha

5. Alpha, 11-dehydroprostaglandin F2

6. D2, Prostaglandin

7. F2 Alpha, 11-dehydroprostaglandin

8. F2alpha, 11-dehydroprostaglandin

9. Pgd2

2.3.2 Depositor-Supplied Synonyms

1. Pgd2

2. 41598-07-6

3. 11-dehydroprostaglandin F2-alpha

4. 11-dehydroprostaglandin F2alpha

5. Brn 2170623

6. (5z,13e,15s)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate

7. Rxy07s6cz2

8. (z)-7-[(1r,2r,5s)-5-hydroxy-2-[(e,3s)-3-hydroxyoct-1-enyl]-3-oxocyclopentyl]hept-5-enoic Acid

9. Chebi:15555

10. (5z,13e)-(15s)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate

11. 9s,15s-dihydroxy-11-oxo-5z,13e-prostadienoic Acid

12. [3h]pgd2

13. [3h]prostaglandin D2

14. Unii-rxy07s6cz2

15. (5z,13e)-(15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate

16. [3h]-pgd2

17. 11-dehydroprostaglandin F2 Alpha

18. Prosta-glandin D2

19. [3h]11-dehydroprostaglandin F2-alpha

20. Pgd2 (prostaglandin D2)

21. Bspbio_001486

22. Pg2

23. Bml1-f05

24. Gtpl1881

25. Gtpl1891

26. Schembl2508829

27. Chembl1235252

28. Bdbm21544

29. Dtxsid30897162

30. Hms1361k08

31. Hms1791k08

32. Hms1989k08

33. Hms3402k08

34. Hms3648m03

35. (5e,13e)-9,15-dihydroxy-11-oxoprosta-5,13-dien-1-oic Acid

36. Lmfa03010004

37. Zinc85994848

38. Prostaglandin D2, >=95%, Synthetic

39. Prostaglandin D2, Cell Culture Tested

40. Db02056

41. Idi1_033956

42. Prosta-5,13-dien-1-oic Acid, 9,15-dihydroxy-11-oxo-, (5z,9-alpha,13e,15s)-

43. Ncgc00161284-01

44. Ncgc00161284-02

45. Ncgc00161284-03

46. Hy-101988

47. Cs-0022427

48. C00696

49. 9s,15s-dihydroxy-11-oxo-5z,13e-prostadienoate

50. Q419750

51. Sr-01000946237

52. Sr-01000946237-1

53. 9alpha,15s-dihydroxy-11-oxo-prosta-5z,13e-dien-1-oic Acid

54. E8965369-341a-46f4-8677-2ceb4f9432ba

55. (5z,13e)-(15s)-9,15-dihydroxy-11-oxoprosta-5,13-dienoate

56. (5z,13e)-(15s)-9,15-dihydroxy-11-oxoprosta-5,13-dienoic Acid

57. (5z,13e)-(15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dienoate

58. (5z,13e)-(15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dienoic Acid

59. (5z,13e,15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate

60. (5z,13e,15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dien-1-oate

61. (5z,13e)-(15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic Acid

62. (5z,13e)-(15s)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic Acid

63. (5z,13e,15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic Acid

64. (5z,13e,15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dien-1-oic Acid

65. (5z,13e,15s)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dien-1-oic Acid

66. (5z,9-alpha,13e,15s)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oate

67. (5z,9alpha,13e,15s)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oate

68. (5z,9alpha,13e,15s)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oic Acid

69. (5z,9alpha,13e,15s)-9,15-dihydroxy-11-oxoprosta-5,13-dien-1-oic Acid

70. (5z,9-alpha,13e,15s)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oic Acid

71. 9,15- Dihydroxy-11-oxo-prosta-5,13-dien-1-oic Acid, (5z,9-.alpha.,13e,15s)

72. (5z)-7-[(1r,2r,5s)-5-hydroxy-2-[(1e,3s)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic Acid

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 352.5 g/mol
Molecular Formula C20H32O5
XLogP32.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count12
Exact Mass352.22497412 g/mol
Monoisotopic Mass352.22497412 g/mol
Topological Polar Surface Area94.8 Ų
Heavy Atom Count25
Formal Charge0
Complexity469
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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