LBF20306CV02: Difference between revisions

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{{Lipid/Header}}
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|LipidBank=XPR8041
|LipidBank=XPR8041
|LipidMaps=LMFA03120022
|LipidMaps=LMFA03120022
|SysName= (R) -4-{ (E) -3- [ (1R,2S) -2- [ (Z) -2-octenyl ] -5-oxo-3-cyclopentenyl ] -1-propenyl}-4-butanolide
|SysName=4R- {trans-3- [ (1R,2S) -2- (cis-2-Octenyl) -5-oxo-3-cyclopentenyl] -1-propenyl} -4-butanolide
|Common Name=&&preclavulone lactone II&& (R) -4-{ (E) -3- [ (1R,2S) -2- [ (Z) -2-octenyl ] -5-oxo-3-cyclopentenyl ] -1-propenyl}-4-butanolide&&
|Common Name=&&Preclavulone lactone II&&4R- {3E- [ (1R,2S) -2- (2Z-Octenyl) -5-oxo-3-cyclopentenyl] -1-propenyl}-4-butanolide&&
|Reflactive=[<FONT FACE="Symbol">a</FONT>]<SUB><FONT SIZE=-1>D</FONT></SUB> -110°[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|Optical=[ alpha ]_D  -110°[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(500MHz,CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>)<FONT FACE="Symbol">d</FONT>ppm0.89(3H,t,J=7.2Hz),1.2-1.4(6H,m),1.96(1H,m),2.00(2H,brq,J=7.3Hz),2.11(1H,m),2.27(1H,m),2.32(1H,m),2.37(1H,m),2.50(2H,m),2.52(2H,m),2.67(1H,qt,J=2.4,7.0Hz),4.89(1H,q,J=6.7Hz),5.33(1H,brtd,J=7.8,10.9Hz),5.52(1H,brtd,J=7.3,10.9Hz),5.58(1H,brdd,J=6.7,15.2Hz),5.76(1H,brtd,J=7.7,15.2Hz),6.15(1H,dd,J=2.4,5.8Hz),7.58(1H,dd,J=2.4,5.8Hz).[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]] <SUP><FONT SIZE=-1>1</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP>C-NMR(125MHz,CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>)<FONT FACE="Symbol">d</FONT>ppm14.0,22.5,27.3,28.5,28.7,29.2,31.3,31.5,33.1,46.9,50.2,80.4,125.2,130.1,131.5,133.0,133.1,166.9,176.8,210.6[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|NMR Spectra=^1 H-NMR(500MHz,CDCl_3 ) delta ppm0.89(3H,t,J=7.2Hz),1.2-1.4(6H,m),1.96(1H,m),2.00(2H,brq,J=7.3Hz),2.11(1H,m),2.27(1H,m),2.32(1H,m),2.37(1H,m),2.50(2H,m),2.52(2H,m),2.67(1H,qt,J=2.4,7.0Hz),4.89(1H,q,J=6.7Hz),5.33(1H,brtd,J=7.8,10.9Hz),5.52(1H,brtd,J=7.3,10.9Hz),5.58(1H,brdd,J=6.7,15.2Hz),5.76(1H,brtd,J=7.7,15.2Hz),6.15(1H,dd,J=2.4,5.8Hz),7.58(1H,dd,J=2.4,5.8Hz).[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]] ^{13}C-NMR(125MHz,CDCl_3 ) delta ppm14.0,22.5,27.3,28.5,28.7,29.2,31.3,31.5,33.1,46.9,50.2,80.4,125.2,130.1,131.5,133.0,133.1,166.9,176.8,210.6[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|Source=Preclavulone lactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|Chemical Synthesis=
|Metabolism=Preclavulone lactone may possibly be biosynthesized from preclavulon A. Clavulones may be biosynthesized from preclavulone lactones via clavulolactones by oxygenation at C-12, dehydration between C-7 and C-8, and esterification at C-1 and C-4. [[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
}}
}}
{{Lipid/Footer}}

Latest revision as of 05:42, 21 October 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR8041
LipidMaps LMFA03120022
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20306CV02
Preclavulone lactone II
LBF20306CV02.png
Structural Information
4R- {trans-3- [ (1R,2S) -2- (cis-2-Octenyl) -5-oxo-3-cyclopentenyl] -1-propenyl} -4-butanolide
  • Preclavulone lactone II
  • 4R- {3E- [ (1R,2S) -2- (2Z-Octenyl) -5-oxo-3-cyclopentenyl] -1-propenyl}-4-butanolide
Formula C20H28O3
Exact Mass 316.203844762
Average Mass 316.43452
SMILES C(CC=CC[C@@H]([C@@H]1CC=C[C@@H](C2)OC(=O)C2)C=CC(=O)1)CCC
Physicochemical Information
[ α ]D -110° IwashimaMet al.
Preclavulone lactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard. Iwashima_M et al.
Preclavulone lactone may possibly be biosynthesized from preclavulon A. Clavulones may be biosynthesized from preclavulone lactones via clavulolactones by oxygenation at C-12, dehydration between C-7 and C-8, and esterification at C-1 and C-4. Iwashima_M et al.
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra 1H-NMR(500MHz,CDCl3) δ ppm0.89(3H,t,J=7.2Hz),1.2-1.4(6H,m),1.96(1H,m),2.00(2H,brq,J=7.3Hz),2.11(1H,m),2.27(1H,m),2.32(1H,m),2.37(1H,m),2.50(2H,m),2.52(2H,m),2.67(1H,qt,J=2.4,7.0Hz),4.89(1H,q,J=6.7Hz),5.33(1H,brtd,J=7.8,10.9Hz),5.52(1H,brtd,J=7.3,10.9Hz),5.58(1H,brdd,J=6.7,15.2Hz),5.76(1H,brtd,J=7.7,15.2Hz),6.15(1H,dd,J=2.4,5.8Hz),7.58(1H,dd,J=2.4,5.8Hz). IwashimaMet al. 13C-NMR(125MHz,CDCl3) δ ppm14.0,22.5,27.3,28.5,28.7,29.2,31.3,31.5,33.1,46.9,50.2,80.4,125.2,130.1,131.5,133.0,133.1,166.9,176.8,210.6 IwashimaMet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20306CV02 See above. Iwashima_M et al. 1997


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