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|LipidBank=XPR7018
|LipidBank=XPR7018
|LipidMaps=LMFA08020004
|LipidMaps=LMFA08020004
|SysName=N- (5-cis,8-cis,11-cis,14-cis-Eicosatetraenoyl) -D-serine
|SysName=N- (cis-5,cis-8,cis-11,cis-14) -Eicosatetraenoyl-D-serine
|Common Name=&&N- (5Z,8Z,11Z,14Z-Eicosatetraenoyl) -D-serine&&N-Arachidonoyl-D-serine&&
|Common Name=&&N-Arachidonoyl-D-serine&&
|Melting Point=colorless oil [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|{{RelationTable/GetFirstAuthor|Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659}}]]
N- (5Z,8Z,11Z,14Z) -Eicosatetraenoyl-D-serine&&|Melting Point=colorless oil [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|Sheskin_T et al.]]
|Optical=[ alpha ]^{25}_4 = -8.9°(C=1,CHCl3)[[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|{{RelationTable/GetFirstAuthor|Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659}}]]
|Optical=[ alpha ]^{25}_4 = -8.9°(C=1,CHCl3)[[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|Sheskin_T et al.]]
|NMR Spectra=^1 H NMR (CD3OD)  delta 5.30-5.43 (m, 8H), 4.49 (t, J=4.8Hz, 1H), 3.80-3.88 (m, 2H), 2.80-2.86 (m, 6H), 2.30 (t, J=6.6Hz, 2H), 2.04-2.18 (m, 4H), 1.66-1.72 (m, 2H), 1.29-1.39 (m, 6H), 0.90 (t, J=6.9Hz, 3H) [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|{{RelationTable/GetFirstAuthor|Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659}}]]
|NMR Spectra=^1 H NMR (CD3OD)  delta 5.30-5.43 (m, 8H), 4.49 (t, J=4.8Hz, 1H), 3.80-3.88 (m, 2H), 2.80-2.86 (m, 6H), 2.30 (t, J=6.6Hz, 2H), 2.04-2.18 (m, 4H), 1.66-1.72 (m, 2H), 1.29-1.39 (m, 6H), 0.90 (t, J=6.9Hz, 3H) [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|Sheskin_T et al.]]
|Source=
|Source=
|Chemical Synthesis=This compound was synthesized from D-serine and N-hydroxysuccinimide ester of arachidonic acid. The yield was 60 %. [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|{{RelationTable/GetFirstAuthor|Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659}}]]
|Chemical Synthesis=This compound was synthesized from D-serine and N-hydroxysuccinimide ester of arachidonic acid. The yield was 60 %. [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|Sheskin_T et al.]]
|Metabolism=
|Metabolism=
|Biological Activity=Binding of this compoud to the brain cannabinoid receptor (CBl), Ki(nM)>10000 [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|{{RelationTable/GetFirstAuthor|Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659}}]]
|Biological Activity=Binding of this compoud to the brain cannabinoid receptor (CBl), Ki(nM)>10000 [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|Sheskin_T et al.]]
}}
}}


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{{Lipid/Footer}}

Latest revision as of 11:36, 2 December 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR7018
LipidMaps LMFA08020004
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20406AM02
N-Arachidonoyl-D-serine
Structural Information
N- (cis-5,cis-8,cis-11,cis-14) -Eicosatetraenoyl-D-serine
  • N-Arachidonoyl-D-serine
  • N- (5Z,8Z,11Z,14Z) -Eicosatetraenoyl-D-serine
Formula C23H37NO4
Exact Mass 391.27225867699997
Average Mass 391.54422
SMILES [C@H](CO)(C(O)=O)NC(CCCC=CCC=CCC=CCC=CCCCCC)=O
Physicochemical Information
colorless oil Sheskin_T et al.
[ α ]25
4   = -8.9°(C=1,CHCl3)SheskinTet al.
This compound was synthesized from D-serine and N-hydroxysuccinimide ester of arachidonic acid. The yield was 60 %. Sheskin_T et al.
Binding of this compoud to the brain cannabinoid receptor (CBl), Ki(nM)>10000 Sheskin_T et al.
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra 1H NMR (CD3OD) δ 5.30-5.43 (m, 8H), 4.49 (t, J=4.8Hz, 1H), 3.80-3.88 (m, 2H), 2.80-2.86 (m, 6H), 2.30 (t, J=6.6Hz, 2H), 2.04-2.18 (m, 4H), 1.66-1.72 (m, 2H), 1.29-1.39 (m, 6H), 0.90 (t, J=6.9Hz, 3H) SheskinTet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406AM02 See above. Sheskin_T et al. 1997


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