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{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
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|LipidBank=XPR7055
|LipidBank=XPR7055
|LipidMaps=LMFA08020041
|LipidMaps=LMFA08020041
|SysName=N- (2-methyl-2-hydroxyethyl) arachidonoylamide (S)  
|SysName=N-2S-Methyl-2-hydroxyethyl- (cis-5,cis-8,cis-11,cis-14) -eicosatetraenoylamine
|Common Name=&&N- (2-methyl-2-hydroxyethyl) arachidonoylamide (S) &&
|Common Name=&&N- (S) -2-Methyl-2-hydroxyethylarachidonoylamide&&N- (S) -2-Methyl-2-hydroxyethyl- (5Z,8Z,11Z,14Z) -eicosatetraenoylamine&&
|Melting Point=colorless oil [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]]
|Melting Point=colorless oil [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]]
|Reflactive=dX<sub>4</sub><sup>25</sup>= +9.44° [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]]
|Optical=[ alpha ]^{25}_4 = +9.44° [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H NMR (200 MHz, CDCl3) <FONT FACE="Symbol">d</FONT>(TMS)6.42 (m, 1H), 5.46-5.30 (m, 8H), 3.93-3.85 (m, 1H), 3.47-3.36 (m, 1H), 3.16-3.03 (m, 1H), 2.83-2.80 (m, 6H), 2.26-2.01 (m, 6H), 1.78-1.64 (m, 2H), 1.39-1.25 (m, 6H), 1.18 (d, J=3.18Hz, 3H), 0.89 (t, J=6.43 Hz, 3H) [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]]
|NMR Spectra=^1 H NMR (200 MHz, CDCl3) delta (TMS)6.42 (m, 1H), 5.46-5.30 (m, 8H), 3.93-3.85 (m, 1H), 3.47-3.36 (m, 1H), 3.16-3.03 (m, 1H), 2.83-2.80 (m, 6H), 2.26-2.01 (m, 6H), 1.78-1.64 (m, 2H), 1.39-1.25 (m, 6H), 1.18 (d, J=3.18Hz, 3H), 0.89 (t, J=6.43 Hz, 3H) [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]]
|Chromatograms=Rf 0.3(5% MeOH/CHCl3)
|Chromatograms=Rf 0.3(5% MeOH/CHCl3)
|Source=
|Chemical Synthesis=This compound was synthesized from arachidonic acid and (S)-(+)-l-amino-2-propanol in 63% yield. [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]]
|Metabolism=
|Biological Activity={{Image200|LBF20406AM38FT7055.gif}} [[Reference:Seltzman_HH:Fleming_DN:Thomas_BF:Gilliam_AF:McCallion_DS:Pertwee_RG:Compton_DR:Martin_BR:,J. Med. Chem.,1997,40,3626|{{RelationTable/GetFirstAuthor|Reference:Seltzman_HH:Fleming_DN:Thomas_BF:Gilliam_AF:McCallion_DS:Pertwee_RG:Compton_DR:Martin_BR:,J. Med. Chem.,1997,40,3626}}]]
}}
}}
{{Lipid/Footer}}

Latest revision as of 04:49, 21 October 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR7055
LipidMaps LMFA08020041
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20406AM38
N- (S) -2-Methyl-2-hydroxyethylarachidonoylamide
LBF20406AM38.png
Structural Information
N-2S-Methyl-2-hydroxyethyl- (cis-5,cis-8,cis-11,cis-14) -eicosatetraenoylamine
  • N- (S) -2-Methyl-2-hydroxyethylarachidonoylamide
  • N- (S) -2-Methyl-2-hydroxyethyl- (5Z,8Z,11Z,14Z) -eicosatetraenoylamine
Formula C23H39NO2
Exact Mass 361.298079497
Average Mass 361.5613
SMILES C(CCC=CCC=CCC=CCC=CCCCCC)C(NC[C@H](C)O)=O
Physicochemical Information
colorless oil Abadji_V et al.
[ α ]25
4   = +9.44° AbadjiVet al.
This compound was synthesized from arachidonic acid and (S)-(+)-l-amino-2-propanol in 63% yield. Abadji_V et al.

LBF20406AM38FT7055.gif
Seltzman_HH et al.
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra 1H NMR (200 MHz, CDCl3) δ (TMS)6.42 (m, 1H), 5.46-5.30 (m, 8H), 3.93-3.85 (m, 1H), 3.47-3.36 (m, 1H), 3.16-3.03 (m, 1H), 2.83-2.80 (m, 6H), 2.26-2.01 (m, 6H), 1.78-1.64 (m, 2H), 1.39-1.25 (m, 6H), 1.18 (d, J=3.18Hz, 3H), 0.89 (t, J=6.43 Hz, 3H) AbadjiVet al.
Other Spectra
Chromatograms Rf 0.3(5% MeOH/CHCl3)
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406AM38 See above. Abadji_V et al. 1994
n.a. LBF20406AM38 See above. Seltzman_HH et al. 1997


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