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{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
{{Hierarchy|{{PAGENAME}}}}


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|LipidBank=XPR2102
|LipidBank=XPR2102
|LipidMaps=LMFA03030006
|LipidMaps=LMFA03030006
|SysName=7- [ Tetrahydro-4 (S) ,6-dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) ,5 (Z) -octadienyl) -2H-pyran-3 (S) -yl ] -5 (Z) -heptenoic acid
|SysName=7- [Tetrahydro- (4S,6) -dihydroxy-2R- (3S-hydroxy- (trans-1,cis-5) -octadienyl) -2H-pyran-3S-yl] -cis-5-heptenoic acid
|Common Name=&&THROMBOXANE B3&&7- [ Tetrahydro-4 (S) ,6-dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) ,5 (Z) -octadienyl) -2H-pyran-3 (S) -yl ] -5 (Z) -heptenoic acid&&
|Common Name=&&Thromboxane B_3&&7- [Tetrahydro- (4S,6) -dihydroxy-2R- (3S-hydroxy- (1E,5Z) -octadienyl) -2H-pyran-3S-yl] -5(Z) -heptenoic acid&&
|Solubility=DIETHYL ETHER [[Reference:Hamberg_M:,Biochim. Biophys. Acta,1980,618,389|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:,Biochim. Biophys. Acta,1980,618,389}}]], ETHYL ACETATE, CHLOROFORM [[Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769|{{RelationTable/GetFirstAuthor|Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769}}]]
|Solubility=DIETHYL ETHER [[Reference:Hamberg_M:,Biochim. Biophys. Acta,1980,618,389|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:,Biochim. Biophys. Acta,1980,618,389}}]], ETHYL ACETATE, CHLOROFORM [[Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769|{{RelationTable/GetFirstAuthor|Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769}}]]
|Mass Spectra=FAB : m/e 351(M<SUP><FONT SIZE=-1>+</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>-H<SUB><FONT SIZE=-1>2</FONT></SUB>O), 333, 315, 307 [[Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769|{{RelationTable/GetFirstAuthor|Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769}}]]
|Mass Spectra=FAB : m/e 351(M^{+1}-H_2 O), 333, 315, 307 [[Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769|{{RelationTable/GetFirstAuthor|Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769}}]]
|IR Spectra=FILM : <FONT FACE="Symbol">n</FONT> 3392, 3010, 2932, 1713, 1407, 1363, 1231, 1154, 1104, 1024, 973, 895 cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP> [[Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769|{{RelationTable/GetFirstAuthor|Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769}}]]
|IR Spectra=FILM : nu  3392, 3010, 2932, 1713, 1407, 1363, 1231, 1154, 1104, 1024, 973, 895 cm^{-1} [[Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769|{{RelationTable/GetFirstAuthor|Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>, TMS) : <FONT FACE="Symbol">d</FONT> 5.85(dd, J=17.5, 6.3Hz,1H, 14-CH), 5.71(dd, J=17.5, 7.5Hz, 1H, 13-CH), 5.55(td, J=20.0, 12.5Hz, 1H, 18-CH), 5.48-5.31(m, 4H, 5,6,11,17-CH), 4.41(dd, J=12.5, 7.5Hz, 1H, 12-CH), 4.23(dt, J=12.5, 6.3Hz, 1H, 15-CH), 4.08(m, 1H, 9-CH), 2.40-2.24(m, 4H, 4,16-CH), 2.18-1.96(m, 7H, 2,7,10,19-CH), 1.81(m, 2H, 3-CH), 1.74-1.63(m, 2H, 3-CH), 1.45(tdd, J=8.8, 5.0, 5.0Hz, 1H, 8-CH), 0.96(t, J=7.5Hz, 3H, 20-CH) [[Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769|{{RelationTable/GetFirstAuthor|Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769}}]] <SUP><FONT SIZE=-1>1</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP>C-NMR(CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>) : 177.25, 136.52, 135.22, 130.75, 129.22, 127.49, 123.66, 123.59, 92.56, 71.58, 69.20, 64.95, 44.99, 36.01, 34.72, 32.89, 26.31, 24.80, 24.58, 24.58, 20.76, 14.21[[Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769|{{RelationTable/GetFirstAuthor|Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769}}]]
|NMR Spectra=^1 H-NMR(CDCl_3 , TMS) : delta  5.85(dd, J=17.5, 6.3Hz,1H, 14-CH), 5.71(dd, J=17.5, 7.5Hz, 1H, 13-CH), 5.55(td, J=20.0, 12.5Hz, 1H, 18-CH), 5.48-5.31(m, 4H, 5,6,11,17-CH), 4.41(dd, J=12.5, 7.5Hz, 1H, 12-CH), 4.23(dt, J=12.5, 6.3Hz, 1H, 15-CH), 4.08(m, 1H, 9-CH), 2.40-2.24(m, 4H, 4,16-CH), 2.18-1.96(m, 7H, 2,7,10,19-CH), 1.81(m, 2H, 3-CH), 1.74-1.63(m, 2H, 3-CH), 1.45(tdd, J=8.8, 5.0, 5.0Hz, 1H, 8-CH), 0.96(t, J=7.5Hz, 3H, 20-CH) [[Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769|{{RelationTable/GetFirstAuthor|Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769}}]] ^{13}C-NMR(CDCl_3 ) : 177.25, 136.52, 135.22, 130.75, 129.22, 127.49, 123.66, 123.59, 92.56, 71.58, 69.20, 64.95, 44.99, 36.01, 34.72, 32.89, 26.31, 24.80, 24.58, 24.58, 20.76, 14.21[[Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769|{{RelationTable/GetFirstAuthor|Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769}}]]
|Source=
|Chemical Synthesis=[[Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769|{{RelationTable/GetFirstAuthor|Reference:Nakamura_N:Nagai_H:Yoneda:M:Suga_H:Kawamura_M:Iguchi_S:,Chem. Pharm. Bull. (Tokyo),1993,41,1769}}]] {{Image200|LBF20303TX02FT0001.gif}}
|Metabolism=Prostaglandin H3 is produced from 5,8,11,14,17-eicosapentaenoic acid by the catalysis of fatty acid cyclooxygenase, and then transformed to unstable thromboxane A3 [[Reference:Needleman_P:Raz_A:Minkes_MS:Ferrendelli_JA:Sprecher_H:,Proc. Natl. Acad. Sci. U. S. A.,1979,76,944|{{RelationTable/GetFirstAuthor|Reference:Needleman_P:Raz_A:Minkes_MS:Ferrendelli_JA:Sprecher_H:,Proc. Natl. Acad. Sci. U. S. A.,1979,76,944}}]], which is converted non-enzymatically to stable thromboxane B3.
|Symbol=TXB3
}}
}}
{{Lipid/Footer}}

Latest revision as of 07:07, 21 October 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR2102
LipidMaps LMFA03030006
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20303TX02
Thromboxane B3
LBF20303TX02.png
Structural Information
7- [Tetrahydro- (4S,6) -dihydroxy-2R- (3S-hydroxy- (trans-1,cis-5) -octadienyl) -2H-pyran-3S-yl] -cis-5-heptenoic acid
  • Thromboxane B3
  • 7- [Tetrahydro- (4S,6) -dihydroxy-2R- (3S-hydroxy- (1E,5Z) -octadienyl) -2H-pyran-3S-yl] -5(Z) -heptenoic acid
 TXB3
Formula C20H32O6
Exact Mass 368.219888756
Average Mass 368.46448
SMILES C(=CC[C@@H](O)C=C[C@@H](O1)[C@H]([C@H](CC1O)O)CC=CCCCC(O)=O)CC
Physicochemical Information
DIETHYL ETHER HambergM, ETHYL ACETATE, CHLOROFORM NakamuraNet al.
Nakamura_N et al.
LBF20303TX02FT0001.gif
 Prostaglandin H3 is produced from 5,8,11,14,17-eicosapentaenoic acid by the catalysis of fatty acid cyclooxygenase, and then transformed to unstable thromboxane A3 Needleman_P et al., which is converted non-enzymatically to stable thromboxane B3.
Spectral Information
Mass Spectra FAB : m/e 351(M+1-H2O), 333, 315, 307 NakamuraNet al.
UV Spectra
IR Spectra FILM : ν 3392, 3010, 2932, 1713, 1407, 1363, 1231, 1154, 1104, 1024, 973, 895 cm-1 NakamuraNet al.
NMR Spectra 1H-NMR(CDCl3, TMS) : δ 5.85(dd, J=17.5, 6.3Hz,1H, 14-CH), 5.71(dd, J=17.5, 7.5Hz, 1H, 13-CH), 5.55(td, J=20.0, 12.5Hz, 1H, 18-CH), 5.48-5.31(m, 4H, 5,6,11,17-CH), 4.41(dd, J=12.5, 7.5Hz, 1H, 12-CH), 4.23(dt, J=12.5, 6.3Hz, 1H, 15-CH), 4.08(m, 1H, 9-CH), 2.40-2.24(m, 4H, 4,16-CH), 2.18-1.96(m, 7H, 2,7,10,19-CH), 1.81(m, 2H, 3-CH), 1.74-1.63(m, 2H, 3-CH), 1.45(tdd, J=8.8, 5.0, 5.0Hz, 1H, 8-CH), 0.96(t, J=7.5Hz, 3H, 20-CH) NakamuraNet al. 13C-NMR(CDCl3) : 177.25, 136.52, 135.22, 130.75, 129.22, 127.49, 123.66, 123.59, 92.56, 71.58, 69.20, 64.95, 44.99, 36.01, 34.72, 32.89, 26.31, 24.80, 24.58, 24.58, 20.76, 14.21 NakamuraNet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20303TX02 See above. Hamberg_M 1980
n.a. LBF20303TX02 See above. Nakamura_N et al. 1993
n.a. LBF20303TX02 See above. Needleman_P et al. 1979


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