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Chemistry

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Also known as: Gibberellic acid, Gibberellin a3, 77-06-5, Berelex, Brellin, Gib-sol

Molecular Formula

C₁₉H₂₂O₆

Molecular Weight

346.4 g/mol

InChI Key

IXORZMNAPKEEDV-OBDJNFEBSA-N

FDA UNII

BU0A7MWB6L

RN given refers to (1alpha,2beta,4aalpha,4bbeta,10beta)-isomer; structure

1 2D Structure

(+)-Gibberellic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,2R,5S,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-13-ene-9-carboxylic acid

2.1.2 InChI

InChI=1S/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16-,17+,18+,19-/m1/s1

2.1.3 InChI Key

IXORZMNAPKEEDV-OBDJNFEBSA-N

2.2 Other Identifiers

2.2.1 UNII

BU0A7MWB6L

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Gibberellic Acid

2. Gibberellin A3

3. Ga3 Gibberellin

4. Ga(3) Gibberellin

2.3.2 Depositor-Supplied Synonyms

1. Gibberellic Acid

2. Gibberellin A3

3. 77-06-5

4. Berelex

5. Brellin

6. Gib-sol

7. Cekugib

8. Gibberellin X

9. Gib-tabs

10. Gibberellic Acid Ga3

11. Gibreskol

12. Grocel

13. Pro-gibb

14. Pro-gibb Plus

15. Gibberellins A4a7

16. Gibrescol

17. Gibefol

18. Regulex

19. Ryzup

20. Activol Ga

21. Acide Gibberellique

22. Gibb-3-ene-1,10-dicarboxylic Acid, 2,4a,7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,2beta,4aalpha,4bbeta,10beta)-

23. Chebi:28833

24. Gibberellin 3

25. Bu0a7mwb6l

26. Nci-c55823

27. Dtxsid0020656

28. Nsc-14190

29. Dtxcid40656

30. Gibrel

31. 2,4a,7-trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylic Acid 1,4a-lactone

32. (1alpha,2beta,4aalpha,4bbeta,10beta)-2,4a,7-trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylic Acid 1,4a-lactone

33. 2beta,4alpha,7-trihydroxy-1-methylene-4aalpha,4bbeta-gibb-3-ene-1alpha,10beta-dicarboxylic Acid 1,4a-lactone

34. Ga3 Gibberellin

35. (1r,2r,5s,8s,9s,10r,11s,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo(9.3.2.15,8.01,10.02,8)heptadec-13-ene-9-carboxylic Acid

36. (1r,2r,5s,8s,9s,10r,11s,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-13-ene-9-carboxylic Acid

37. Ga(3) Gibberellin

38. Refchem:5857

39. 2,4 Alpha,7-trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10 Beta-dicarboxylic Acid 1,4 Alpha-lactone

40. 201-001-0

41. Gibberellinsaeure

42. Pgr-iv

43. Ga3

44. Mfcd00079329

45. Gibberelic Acid

46. Acide Gibberellique [iso-french]

47. Gibbrel

48. Gibberellic Acid [bsi:iso]

49. Ai3-52922

50. Gibberellic Acid, 90%

51. Nsc14190

52. (3s,3as,4s,4as,6s,8ar,8br,11s)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno(1,2-b)furan-4-carboxylic Acid

53. Ncgc00091033-01

54. Gibberellic Acid 100 Microg/ml In Acetonitrile

55. Gibb-3-ene-1,10-dicarboxylic Acid, 2,4a,7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone

56. Gibberellate

57. (3s,3ar,4s,4as,7s,9ar,9br,12s)-7,12-dihydroxy-3-methyl-6-methylene-2-oxoperhydro-4a,7-methano-9b,3-propenoazuleno(1,2-b)furan-4-carboxylic Acid

58. (3s,3as,4s,4as,6s,8as,8bs,11s)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno(1,2-b)furan-4-carboxylic Acid

59. (3s,3as,4s,4as,7s,9ar,9br,12s)-7,12-dihydroxy-3-methyl-6-methylene-2-oxoperhydro-4a,7-methano-9b,3-propeno(1,2-b)furan-4-carboxylic Acid

60. 2beta,4aalpha,7-trihydroxy-1beta-methyl-8-methylene-4aalpha,4bbeta-gibb-3-ene-1alpha,10beta-dicarboxylic Acid 1,4a-lactone

61. 2beta,4alpha,7-trihydroxy-1-methyl-8-methylene-4aalpha,4bbeta-gibb-3-ene-1alpha,10beta-dicarboxylic Acid 1,4a-lactone

62. Giberellin

63. (3s,3as,4s,4as,6s,8ar,8br,11s)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic Acid

64. 2,4alpha,7-trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10 Beta-dicarboxylic Acid 1,4alpha-lactone

65. Caswell No. 467

66. Unii-bu0a7mwb6l

67. Gibberelate

68. Gibberelin

69. Gibberillate

70. Ga [plant Growth Regulator]

71. Gibberellic Acid [iso:bsi]

72. Nsc19450

73. Ccris 4820

74. Gibberillic Acid

75. Hsdb 712

76. Gibb-tabs

77. Gibberellic A3

78. 4psb

79. 2,7-trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-carboxylic Acid 1-4-lactone

80. Cas-77-06-5

81. Gibberellin (ga)

82. (1s,2s,4ar,4br,7s,9as,10s,10ar)-2,7-dihydroxy-1-methyl-8-methylene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic Acid

83. Gibb-3-ene-1, 2,4a,7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1.alpha.,2.beta.,4a.alpha.,4b.beta.,10.beta.)-

84. Gibb-3-ene-1,10-dicarboxylic Acid, 2,4a,7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1.alpha.,2.beta.,4a.alpha.,4b.beta.,10.beta.)-

85. Einecs 201-001-0

86. Nsc 14190

87. Epa Pesticide Chemical Code 043801

88. Gibberellin A3;ga3

89. Giberillic Acid

90. Brn 0054346

91. Spectrum_000628

92. 4q0k

93. Specplus_000148

94. 2b-hydroxygibberellin 1

95. Gibberellinsa Currencyure

96. Ps49_supelco

97. Prestwick0_000965

98. Prestwick1_000965

99. Prestwick2_000965

100. Prestwick3_000965

101. Spectrum2_000311

102. Spectrum3_001301

103. Spectrum4_001444

104. Spectrum5_000027

105. Gibberellic Acid (ga-3)

106. Bmse000317

107. Schembl15577

108. Bspbio_000969

109. Bspbio_002961

110. Kbiogr_001927

111. Kbioss_001108

112. 5-18-09-00269 (beilstein Handbook Reference)

113. Mls001055447

114. Mls002154076

115. Divk1c_006244

116. G7645_sigma

117. Gibberellic Acid [mi]

118. Spbio_000302

119. Spbio_002890

120. Gibberellic Acid [iso]

121. Bpbio1_001067

122. Megxm0_000440

123. Orb1304803

124. Gibberellic Acid [hsdb]

125. Chembl1232952

126. Acon0_000224

127. Acon1_000551

128. Bcbcmap01_000012

129. Kbio1_001188

130. Kbio2_001108

131. Kbio2_003676

132. Kbio2_006244

133. Kbio3_002181

134. Gibberellic Acid [usp-rs]

135. Hms1571a11

136. Hms2098a11

137. Hms2231j16

138. Hms3039m06

139. (1r,2r,5s,8s,9s,10r,11s,12s)-5,12-dihydroxy-11-methyl-6-methylene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-13-ene-9-carboxylic Acid

140. Hy-n1964

141. Msk21129

142. Tox21_202052

143. Tox21_303023

144. Bdbm50561592

145. Geo-04261

146. Md-920

147. Nsc-19450

148. S4766

149. Akos024464812

150. Akos025310145

151. Ccg-208472

152. Db07814

153. Fg30500

154. Smp1_000136

155. Ncgc00091033-02

156. Ncgc00091033-03

157. Ncgc00091033-04

158. Ncgc00091033-05

159. Ncgc00091033-06

160. Ncgc00091033-07

161. Ncgc00091033-09

162. Ncgc00256446-01

163. Ncgc00259601-01

164. As-14216

165. Nci60_000922

166. Smr000686070

167. Smr001233386

168. Ab00513979

169. Cs-0018282

170. A11801

171. G-2700

172. Gibberellin, 80% Gibberellin A3 Basis (tlc)

173. Gibberellic Acid 1000 Microg/ml In Acetonitrile

174. 079g329

175. Dihydroxy-methyl-methylene-oxo-[?]carboxylic Acid

176. En300-19631964

177. F463838

178. Q411138

179. Gibberellic Acid, 90% Gibberellin A3 Basis (hplc)

180. Gibberellic Acid, Pestanal(r), Analytical Standard

181. Brd-k92758126-001-05-5

182. Brd-k92758126-001-06-3

183. Brd-k92758126-001-17-0

184. Brd-k92758126-001-18-8

185. 6f94d8a8-3230-4ab5-93c1-46f5e84fe343

186. Gibberellic Acid, Pharmaceutical Secondary Standard; Certified Reference Material

187. (1.alpha.,2.beta.,4a.alpha.,4b.beta.,10.beta.)-2,4a,7-trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylic Acid 1,4a-lactone

188. (1r,2r,5s,8s,9s,10r,11s,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1(5,8).0(1,10).0(2,8)]heptadec-13-ene-9-carboxylic Acid

189. (1r,2r,5s,8s,9s,10r,11s,12s)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-13-ene-9-carboxylic Acid

190. (1s,2s,4ar,4br,7s,9as,10s,10ar)-2,7-dihydroxy-1-methyl-8-methylidene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic Acid

191. 2,4.alpha.,7-trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylic Acid 1,4-.alpha.-lactone

192. 2beta,7alpha-dihydroxy-1beta-methyl-8-methylidene-13-oxo-4a,1alpha-epoxymethano-4aalpha,4bbeta-gibb-3-ene-10beta-carboxylic Acid

193. Gibberellic Acid, Plant Cell Culture Tested, Bioreagent, >=90% Gibberellin A3 Basis (of Total Gibberellins.)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₂O₆
Molecular Weight	346.4 g/mol
XLogP3	0.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	1
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	104
Heavy Atom Count	25
Formal Charge	0
Complexity	772
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
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

Plant Growth Regulators

Any of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.

4.2 Absorption, Distribution and Excretion

Translocated /in plants/.

Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A797/Aug 87

4.3 Mechanism of Action

Gibberellic acid enhanced activity of rat lung guanylate cyclase, an enzyme associated with growth.

PMID:6104850 Vesely DL, Rochat MH; Res Commun Chem Pathol Pharmacol 28 (1): 123-32 (1980)

Gibberellic acid has androgenic activity in chicks.

PMID:7134120 Anderson DL et al; Poult Sci 61 (8): 1660-6 (1982)

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