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Pregnenolone

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Also known as: 145-13-1, Arthenolone, 3beta-hydroxypregn-5-en-20-one, Pregnetan, Pregneton, Pregnolon

Molecular Formula

C₂₁H₃₂O₂

Molecular Weight

316.5 g/mol

InChI Key

ORNBQBCIOKFOEO-QGVNFLHTSA-N

FDA UNII

73R90F7MQ8

A 21-carbon steroid, derived from CHOLESTEROL and found in steroid hormone-producing tissues. Pregnenolone is the precursor to GONADAL STEROID HORMONES and the adrenal CORTICOSTEROIDS.

1 2D Structure

Pregnenolone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone

2.1.2 InChI

InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1

2.1.3 InChI Key

ORNBQBCIOKFOEO-QGVNFLHTSA-N

2.1.4 Canonical SMILES

CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C

2.1.5 Isomeric SMILES

CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C

2.2 Other Identifiers

2.2.1 UNII

73R90F7MQ8

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5 Pregnen 3 Beta Ol 20 One

2. 5-pregnen-3-beta-ol-20-one

2.3.2 Depositor-Supplied Synonyms

1. 145-13-1

2. Arthenolone

3. 3beta-hydroxypregn-5-en-20-one

4. Pregnetan

5. Pregneton

6. Pregnolon

7. Prenolon

8. Regnosone

9. Skinostelon

10. Enelone

11. 5-pregnen-3beta-ol-20-one

12. Natolone

13. Bina-skin

14. Delta5-pregnenolone

15. 5-pregnen-3-beta-ol-20-one

16. (3beta)-3-hydroxypregn-5-en-20-one

17. 5-pregnenolone

18. 3-beta-hydroxypregn-5-en-20-one

19. Nsc 1616

20. Prestwick_859

21. Pregn-5-en-20-one, 3-hydroxy-, (3beta)-

22. Prestwick3_000546

23. Pregnenolone (jan/inn)

24. Pregn-5-en-20-one, 3beta-hydroxy-

25. 3b-hydroxy-5-pregnen-20-one

26. 1-[(3s,8s,9s,10r,13s,14s,17s)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone

27. Pregn-5-en-20-one, 3-hydroxy-, (3b)-

28. Pregn-5-ene-3beta-ol-20-one

29. Chebi:16581

30. 73r90f7mq8

31. 3.beta.-hydroxypregn-5-en-20-one

32. 3beta-hydroxy-5-pregnen-20-one

33. Dsstox_cid_16541

34. Dsstox_rid_79287

35. Dsstox_gsid_36541

36. 5-pregnen-3beta;-ol-20-one

37. Pregnenolona

38. Pregnenolonum

39. Pregnenolone [inn:ban]

40. Pregnenolonum [inn-latin]

41. Pregnenolona [inn-spanish]

42. Plo

43. Smr000112161

44. .delta.5-pregnenolone

45. Pregnenolone (3beta-hydroxypregn-5-en-20-one)

46. Sr-05000002128

47. Einecs 205-647-4

48. 3-hydroxypregn-5-en-20-one

49. 5-pregnen-3.beta.-ol-20-one

50. Pregnolone

51. Nsc-1616

52. Unii-73r90f7mq8

53. Nsc-18158

54. Pregn-5-en-20-one, 3-hydroxy-, (3-beta)-

55. Ncgc00163125-02

56. Pregn-5-en-20-one, 3.beta.-hydroxy-

57. Cas-145-13-1

58. Pregn-5-en-20-one, 3-beta-hydroxy-

59. Prestwick0_000546

60. Prestwick1_000546

61. Prestwick2_000546

62. Spectrum5_002057

63. Pregnenolone [mi]

64. Pregnenolone [inn]

65. Pregnenolone [jan]

66. Bmse000476

67. 5-pregnen-3b-ol-20-one

68. Pregnenolone [vandf]

69. Bidd:pxr0019

70. Bspbio_000591

71. Mls002153868

72. Mls002207138

73. Pregn-5-en-3b-ol-20-one

74. Pregnenolone [who-dd]

75. Schembl129572

76. Pregn-5-ene-3b-ol-20-one

77. Spbio_002512

78. 3b-hydroxypregn-5-en-20-one

79. Bpbio1_000651

80. Chembl253363

81. Gtpl2376

82. Pregn-5-en-3beta-ol-20-one

83. Dtxsid1036541

84. Delta5-pregnen-3beta-ol-20-one

85. 3beta-hydroxy-5-pregenen-20-one

86. 3beta-hydroxy-5-pregnene-20-one

87. 3beta-hydroxypregn-5-ene-20-one

88. Hms1569n13

89. Hms2090j15

90. Hms2096n13

91. Hms2268a04

92. Hms3713n13

93. Hms3884g16

94. Delta5-pregenen-3beta-ol-20-one

95. Delta5-pregnene-3beta-ol-20-one

96. 1-((3s,8s,9s,10r,13s,14s,17s)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl)ethanone

97. 1-[(3s,8s,9s,10r,13s,14s,17s)-10,13-dimethyl-3-hydroxy-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone

98. Bcp23361

99. Hy-b0151

100. Zinc3861150

101. Tox21_112011

102. Tox21_302141

103. Bdbm50375319

104. Cmc_13393

105. Lmst02030088

106. Pregnenolone (progesterone Precursor)

107. S1914

108. 3beta-hydroxy-delta5-pregnen-20-one

109. Akos015841076

110. Akos015895418

111. Tox21_112011_1

112. (3b)-3-hydroxy-pregn-5-en-20-one

113. Ccg-220546

114. Cs-1970

115. Db02789

116. Ds-7794

117. Pregnenolone 0.1 Mg/ml In Acetonitrile

118. .delta.5-pregnen-3.beta.-ol-20-one

119. 5-pregnen-3beta-ol-20-one, >=98%

120. Ncgc00163125-03

121. Ncgc00163125-04

122. Ncgc00163125-06

123. Ncgc00255436-01

124. Ac-12806

125. Ac-32630

126. Bcp0726000217

127. Pregn-5-n-20-ne, 3-ydroxy-, (3)-

128. 3-hydroxypregn-5-en-20-one, (3.beta.)-

129. 3.beta.-hydroxy-.delta.5-pregnen-20-one

130. P0786

131. 3beta-3-hydroxy-pregn-5-en-20-one

132. (3alpha,8alpha)-3-hydroxypregn-5-en-20-one

133. C01953

134. D00143

135. 17beta-[1-ketoethyl]-delta5-androsten-3beta-ol

136. Pregn-5-en-20-one, 3-hydroxy-, (3.beta.)-

137. 145p131

138. Q412158

139. J-008059

140. Sr-05000002128-4

141. Sr-05000002128-5

142. .delta. Sup(5)-pregnen-3.beta.-ol-20-one

143. Brd-k43880410-001-14-4

144. 0f6367c4-e1fa-4aec-9846-7bcc5ada3417

145. Pregn-5-en-20-one, 3-(3-carboxy-, (3.beta.)-

146. 17.beta.-(1-ketoethyl)-.delta. Sup(5)-androsten-3.beta.-ol

147. 1-((3s,8s,10r,13s,17s)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl)-ethanone

148. 1-((3s,8s,9s,10r,13s,14s,17s)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl)ethan-1-one

149. 1-[(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16, 17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl)]ethanone

2.4 Create Date

2005-06-01

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₃₂O₂
Molecular Weight	316.5 g/mol
XLogP3	4.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Exact Mass	316.240230259 g/mol
Monoisotopic Mass	316.240230259 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	550
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 Metabolism/Metabolites

Pregnenolone has known human metabolites that include 1-(3,16-Dihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone, 2-Hydroxy-1-(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone, and Pregn-5-en-20-on-3b-yl sulfurate.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560