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Chemistry

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Also known as: 52-39-1, Electrocortin, Aldocortin, Aldocorten, Aldocortene, (+)-aldosterone

Molecular Formula

C₂₁H₂₈O₅

Molecular Weight

360.4 g/mol

InChI Key

PQSUYGKTWSAVDQ-ZVIOFETBSA-N

FDA UNII

4964P6T9RB

A hormone secreted by the ADRENAL CORTEX that regulates electrolyte and water balance by increasing the renal retention of sodium and the excretion of potassium.

1 2D Structure

Aldosterone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8S,9S,10R,11S,13R,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10-methyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-13-carbaldehyde

2.1.2 InChI

InChI=1S/C21H28O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,11,14-17,19,22,25H,2-7,9-10H2,1H3/t14-,15-,16+,17-,19+,20-,21+/m0/s1

2.1.3 InChI Key

PQSUYGKTWSAVDQ-ZVIOFETBSA-N

2.1.4 Canonical SMILES

CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4C(=O)CO)C=O)O

2.1.5 Isomeric SMILES

C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@H]4C(=O)CO)C=O)O

2.2 Other Identifiers

2.2.1 UNII

4964P6T9RB

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Aldosterone, (+-)-isomer

2. Aldosterone, (11 Beta,17 Alpha)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 52-39-1

2. Electrocortin

3. Aldocortin

4. Aldocorten

5. Aldocortene

6. (+)-aldosterone

7. Reichstein X

8. Elektrocortin

9. D-aldosterone

10. 18-oxocorticosterone

11. Aldosteronum

12. [3h]aldosterone

13. 11beta,21-dihydroxypregn-4-ene-3,18,20-trione

14. 11beta,21-dihydroxy-3,20-diketo-4-pregnen-18-al

15. 11beta,21-dihydroxy-3,20-diketopregn-4-ene-18-al

16. 18-formyl-11beta,21-dihydroxy-4-pregnene-3,20-dione

17. Pregn-4-en-18-al, 11,21-dihydroxy-3,20-dioxo-, (11b)-

18. (11beta)-11,21-dihydroxy-3,20-dioxopregn-4-en-18-al

19. Nsc 73856

20. 11beta,21-dihydroxy-3,20-dioxo-4-pregnen-18-al

21. Nsc-73856

22. (8s,9s,10r,11s,13r,14s,17s)-11-hydroxy-17-(2-hydroxyacetyl)-10-methyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-13-carbaldehyde

23. 11beta,21-dihydroxy-3,20-dioxo-4-pregnen-18-al, 18,11-halbacetal

24. 11beta,21-dihydroxy-3,20-dioxopregn-4-en-18-al

25. 11beta,21-dihydroxy-3,20-dioxo-pregn-4-ene-18-al

26. Chebi:27584

27. 4964p6t9rb

28. Aldosterone (inn)

29. 11.beta.,21-dihydroxypregn-4-ene-3,18,20-trione

30. Pregn-4-en-18-al, 11,21-dihydroxy-3,20-dioxo-, (11beta)-

31. Aldosteronum [inn-latin]

32. Aldosterona

33. Aldosterona [inn-spanish]

34. 18-aldocorticosterone

35. Aldosterone [inn]

36. Aldosterone [inn:ban:dcf]

37. [3h]-aldosterone

38. Smr000857170

39. Einecs 200-139-9

40. Brn 3224996

41. Unii-4964p6t9rb

42. Delta-aldosterone

43. Aldosterone Solution

44. 18-ketocorticosterone

45. 11,21-dihydroxy-3,20-dioxopregn-4-en-18-al

46. Aldosterone [mi]

47. Schembl1675

48. Aldosterone [mart.]

49. Aldosterone [who-dd]

50. 11b,21-dihydroxy-3,20-dioxo-pregn-4-en-18-al

51. 4-08-00-03491 (beilstein Handbook Reference)

52. Mls001333163

53. Mls001333164

54. Bidd:er0511

55. Chembl273453

56. Gtpl2872

57. Gtpl3452

58. Dtxsid7022419

59. Aldosterone, >=95% (hplc)

60. Bdbm19214

61. (11beta)-11,21-dihydroxy-3,20-dioxo-pregn-4-en-18-al

62. Hms2233d14

63. Nsc73856

64. Zinc3833824

65. Lmst02030026

66. Akos024462706

67. Db04630

68. Ncgc00164236-01

69. As-69489

70. Aldosterone 100 Microg/ml In Acetonitrile

71. Hy-113313

72. Cs-0059576

73. C01780

74. D10528

75. Q184564

76. Sr-01000838883

77. Sr-01000838883-2

78. 11beta,21-dihydroxy-3,20-dioxo-pregn-4-en-18-al

79. (11b)-11,21-dihydroxy-3,20-dioxo-pregn-4-en-18-al

80. Pregn-4-en-18-al,21-dihydroxy-3,20-dioxo-, (11.beta.)-

81. Pregn-4-ene-3,20-dione, 11beta,18-epoxy-18,21-dihydroxy-

82. (11alpha,14beta,17alpha)-11,21-dihydroxy-3,20-dioxopregn-4-en-18-al

83. (1s,2r,10s,11s,14s,15r,17s)-17-hydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadec-6-ene-15-carbaldehyde

84. 11-hydroxy-17-(2-hydroxyacetyl)-10-methyl-3-oxo-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-13-carbaldehyde

85. Aldosterone Solution, 100 Mug/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₈O₅
Molecular Weight	360.4 g/mol
XLogP3	1.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	360.19367399 g/mol
Monoisotopic Mass	360.19367399 g/mol
Topological Polar Surface Area	91.7 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	682
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
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 Pharmacology

At the late distal tubule and collecting duct, aldosterone has two main actions: 1) aldosterone acts on mineralocorticoid receptors (MR) on principal cells in the distal tubule of the kidney nephron, increasing the permeability of their apical (luminal) membrane to potassium and sodium and activates their basolateral Na+/K+ pumps, stimulating ATP hydrolysis leading to phosphorylation of the pump and a conformational change in the pump exposes the Na+ ions to the outside. The phosphorylated form of the pump has a low affinity for Na+ ions, hence reabsorbing sodium (Na+) ions and water into the blood, and secreting potassium (K+) ions into the urine; 2) aldosterone stimulates H+ secretion by intercalated cells in the collecting duct, regulating plasma bicarbonate (HCO3) levels and its acid/base balance; and 3) aldosterone may act on the central nervous system via the posterior pituitary gland to release vasopressin (ADH) which serves to conserve water by direct actions on renal tubular resorption.

4.2 ATC Code

H - Systemic hormonal preparations, excl. sex hormones and insulins

H02 - Corticosteroids for systemic use

H02A - Corticosteroids for systemic use, plain

H02AA - Mineralocorticoids

H02AA01 - Aldosterone

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