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Sphingophospholipid

(total 31)
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No Structure COMMON NAME NAME DATA No INFORMANT SYMBOL FORMULA MOL.WT(ave) Download BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINT BOILING POINT DENSITY REFRACTIVE INDEX OPTICAL ROTATION SOLUBILITY UV SPECTRA IR SPECTRA NMR SPECTRA MASS SPECTRA OTHER SPECTRA
1
N-Palmitoyl-D,L-Dihydrosphingomyelin
PSP3095
Keizo Waku
C39H81N2O7P 721.043 Download ChemDraw structure file

224-225degC (Ref. 3017)





This compound was synthesized from N-palmitoyl-3-O-benzoyl-D,L-sphinganin with b-bromoethylphosphoryldichloride and for the subsequent reaction with trimethylamine. (Ref. 3017)



2
N-Oleoyl-D,L-Dihydrosphingomyelin
PSP3096
Keizo Waku
C41H85N2O7P 749.097 Download ChemDraw structure file

208-210degC (Ref. 3017)





This compound was synthesized from N-oleoyl-3-O-benzoyl-D,L-sphinganine with b -bromoethylphosphoryldichloride and for the subsequent reaction with trimethylamine. (Ref. 3017)



3
N-(2'D,L-Hydroxypalmitoyl)D,L-Dihydrosphingomyelin
PSP3097
Keizo Waku
C39H83N2O7P 723.059 Download ChemDraw structure file

228-230degC (Ref. 3017)





This compound was synthesized from N-(2'D,L-Hydroxypalmitoyl)-3-O-benzoyl-D,L-sphinganine with b -bromoethylphosphoryldichloride and for the subsequent reaction with trimethylamine. (Ref. 3017)



4
N-(trans-2-Hexadecenoyl)-D,L-Dihydrosphingomyelin
PSP3098
Keizo Waku
C39H81N2O7P 721.043 Download ChemDraw structure file

205-206degC (Ref. 3017)





This compound was synthesized from N-(trans-2-hexadecenoyl)-3-O-benzoyl-D,L-sphinganine with b-bromoethylphosphoryldichloride and for the subsequent reaction with trimethylamine. (Ref. 3017)



5
N-Palmitoyl-D,L-Sphingomyelin
PSP3099
Keizo Waku
C39H79N2O6P 703.028 Download ChemDraw structure file

209-210degC (Ref. 3017)





This compound was synthesized from N-palmitoyl-3-O-benzoyl-D,L-sphingenine with b -bromoethylphosphoryldichloride and for the subsequent reaction with trimethylamine. (Ref. 3017)



6
N-Oleoyl-D,L-Sphingomyelin
PSP3100
Keizo Waku
C41H83N2O7P 747.081 Download ChemDraw structure file

188-190degC (Ref. 3017)





This compound was synthesized from N-palmitoyl-3-O-benzoyl-D,L-sphinganin with b -bromoethylphosphoryldichloride and for the subsequent reaction with trimethylamine. (Ref. 3017)



7
N-(2'DL-Hydroxypalmitoyl)-D,L-Sphingomyelin
PSP3101
Keizo Waku
Download ChemDraw structure file

219-221degC (Ref. 3017)





This compound was synthesized from N-(2'DL-hydroxypalmitoyl)-3-O-benzoyl-D,L-sphingenine with



8
Dihydrosphingomyelin
dihydroceramide-1-phosphorylcholine
PSP5012
Kentaro Hanada
DSM
Download ChemDraw structure file

insoluble in water; solble in chloroform




Ubiquitous in mammalian (probably ubiquitous in vertebrates)(Ref. 5001)

DSM is formed by phosphorylcholine transfer from phosphatidylcholine to dihydroceramide. In general, the DSM level in cells is lower than the level of sphingomyelin.(Ref. 5002)


9
Sphingomyelin
Ceramide-1-phosphorylcholine
PSP5013
Kentaro Hanada
SM
Download ChemDraw structure file
Essential for mammlian cell growth(Ref. 5037/5038) Formation of detergent-resistant lipid-rafts(Ref. 5039/5040) A reservoir of ceramide in ceramide-mediated signalling(Ref. 5017/5035/5036) Anti-colon cancer effect of dietary SM(Ref. 5041) Influences on cholesterol metabolism(Ref. 5042/5043) In hibition of lecthin-cholesterol acyltransferase activity(Ref. 5044) Interaction between cells and substrata(Ref. 5045) Binding to procollagen(Ref. 5046) A receptor to lysenin (an earthworm-derived cytolysin)(Ref. 5047/5038)
196-198degC(Ref. 5012)
+6 to 7 (in chloroform/methanol)(Ref. 5012)
insoluble in water, diethylether, acetone soluble in chloroform, hot ethanol, hot ethylacetate(Ref. 5012)




Ubiquitous in mammalian (probably ubiquitous in vertebtates)

SM is formed by phosphorylcholine transfer from phosphatidylcholine to ceramide. SM is degradated to ceramide by acid sphingomyelinase in lysosome, or by neutral sphingomyelinase in the plasma membrane.(Ref. 5002)
Acid sphingomyelinase (mouse and human) (Ref. 5022/5023) An isoform of neutral sphingomyelinase (mouse and human)(Ref. 5048) Genetic defects in acid sphingomyelinase cause Niemann-Pick disease type A and B.(Ref. 5022/5023/5049)

10
sphingosine 1-phosphate
PSP6001
Takehiko Yokomizo
S1P/ SPP/ Sph-1-P
C18H38NO5P 379.472 Download ChemDraw structure file
Acts either extracellularly on Edg receptors (Edg1, 3, 5, 6, 8) (Ref. 6005/6007) or intracellularly to cause pleiotropic biological responses (Ref. 6004). Mobilizes intracellular calcium (Ref. 6004). Decreases cAMP. Suppresses ceramide-mediated apoptosis (Ref. 6006). Activates MAP kinasse and phospholipase D (Ref. 6001/6005). Inhibits chemotactic motility and invasiveness of tumor cells (Ref. 6002). Stimulates cell growth (Ref. 6003).
It is difficult to suspend S1P using organic solvents so typically it is suspended in methanol to aliquot, the methanol dried and the residue dispersed using fatty acid free BSA solution. The solubility of stock solutions may be increased by the addition of dimethylamine.

ESI/MS (Ref. 4509).




Synthesized by sphingosine kinase, and dephosphorylated by S1P phosphatase (Ref. 6001). S1P is also converted into fatty aldehyde and phosphoethanolamine by S1P lyase (Ref. 6001).


11
lysosphingomyelin
sphingosylphosphorylcholine
PSP6002
Takehiko Yokomizo
SPC
C23H49N2O5P 464.619 Download ChemDraw structure file
Mobilizes intracellular calcium stores (Ref. 6008) probably via several G protein-coupled receptors, such as OGR1 and GPR4 (Ref. 6014/6015). It regulates numerous cellular functions including cell proliferation (Ref. 6009), cell growth inhibition, smooth muscle contraction, neurite outgrowth (Ref. 6010), and actin rearrangement (Ref. 6013). Activates MAP kinase (Ref. 6012) and transcription factor AP-1 (Ref. 6011).
It is difficult to suspend SPC using organic solvents so typically it is suspended in methanol to aliquot, the methanol dried and the residue dispersed using fatty acid free BSA solution. The solubility of stock solutions may be increased by the addition of dimethylamine.

ESI/MS (Ref. 4509).




Synthesized by sphingomyelin deacetylase (undiscovered enzyme) (Ref. 6008/6010).


12
D-erythro-sphinganine-1-phosphate
dihydrosphingosine-1-phosphate
PSP6003
Takehiko Yokomizo
DHS-1-P/ HSPP
C18H40NO5P 381.488 Download ChemDraw structure file
Saturated analog of sphingosine-1-phosphate displaying 20-fold lower activity (Binds to Edg1 receptor but not functional) (Ref. 6017/6018/6019). Induces chemotaxis in HUVECs (Ref. 6018). May be used as a negative control for intracellular effects of sphingosine-1-phosphate.
Stimulate proliferation and resistance to stress in yeast (Ref. 6021/6022).
It is difficult to suspend sphinganine-1-phosphate using organic solvents so typically it is suspended in methanol to aliquot, the methanol dried and the residue dispersed using fatty acid free BSA solution. The solubility of stock solutions may be increased by the addition of dimethylamine.






Synthesized by sphinganine kinase, and dephosphorylated by sphingosine phosphatase (Ref. 6016).


13
phytosphingosine -1-phosphate
4-hydroxy-D-erythro-sphinganine-1-phosphate
PSP6004
Takehiko Yokomizo
PHS-1-P
C18H40NO6P 397.487 Download ChemDraw structure file
A potential modulator of cellular processes (Ref. 6020). Stimulate proliferation and resistance to stress in yeast (Ref. 6021/6022).
It is difficult to suspend phytosphingosine-1-phosphate using organic solvents so typically it is suspended in methanol to aliquot, the methanol dried and the residue dispersed using fatty acid free BSA solution. The solubility of stock solutions may be increased by the addition of dimethylamine.









14
C8 Ceramide-1-phosphate
D-erythro-C8 ceramide-1-phosphate
PSP6005
Takehiko Yokomizo
C8 ceramide-1-P
C26H52NO6P 505.668 Download ChemDraw structure file
Stimulates DNA synthesis when added exogenously to cultured fibroblasts (Ref. 6023). Mitogenic activity is antagonized by cell permeable ceramides (Ref. 6023).
Soluble in DMSO and ethanol.









15
Ceramide 2-aminoethylphosphonate (Ref. 8001/8003)
PSP8001
Akira Hayashi
CAEPn
Download ChemDraw structure file

IR of CAEPn, pressed in KBr (Ref. 8004);

GC-MS of TMS-2-aminoethylphosphonic acid and of TMS-ceramides obtained from CAEP (Ref. 8001); GC-MA of TMS-CAEP (long-chain base originated ions and ceramide originated ions) (Ref. 8001); FAB-MS of CAEP (m/z 126 ion, long-chain base ions, ceramide ions and [M+H] + ions in positive ion mode and m/z 124 ion and [M-H]- ions in negative ion mode(Ref. 8002/8003)

Silicic acid column chromatography of oyster adductor lipids eluted ceramide aminoethylphosphonate in chloroform-methanol (9:1, v/v) fraction. (Ref. 8001) ; TLC of CAEPn (Ref. 8004); TLC of CAEPn from Turbo cornutus (Ref. 8008)
Oyster visceral tissues (Ref. 8004); Oyster adductor (Ref. 8001); Euhadra hickonis (Ref. 0005); Oyster (Ostrea gigas), adductor (+++), gills (+++), mantle (+++) and viscera (+++) (Ref. 8003/8006/8012/8019) Protozoa , Tetrahymena pyriformis W (+) (Ref. 8006/8010/8019); Protozoa, Tetrahymena pyriformis WH-14(++) (Ref. 8006/8013/8019); Mollusca, Liolophura japonica (++) (Ref. 8006/8012/8019); Mollusca, Tegla lischkei (+) (Ref. 8006/8012/8019); Mollusca, Conomurex luhuanun (+++) (Ref. 8006/8012/8019); Mollusca, Cellanaeucosmia (+++) (Ref. 8006/8012/8019); Mollusca, Mytilus edulis (+++) (Ref. 8006/8012/8019); Mollusca, Hyriopsis schlegelli, Ova (++) (Ref. 8013/8006/8019), spermatozoa (++) (Ref. 8006/8014/8015/8019); Scallop, Hennifes giganteum (+++) (Ref. 8006/8016/8019); Pink abalone, Haliotis corrugata (++) (Ref. 8006/8016/8019); Coelenterata, Anthopleura elegantissima (+++) (Ref. 8006/8017/8019); Coelenterata, Metridium senile (++) (Ref. 8006/8018/8019)



Fatty acid composition (Ref. 0004/8001/8003); Long-chain base composition (Ref. 8001/8003)
16
N-Hexadecanoyl-hexadecasphingosine 2-aminoethylphosphonate (Ref. 8001)
PSP8002
Akira Hayashi
C16:0-d16:1-AEPn
C34H69O5N2P1 616.896 Download ChemDraw structure file


GC-EI-MS of TMS-Ceramide(0C16:0-d16:1) (Ref. 8001); GC-EI-MS of TMS-CAEP (C16:0-d16:1-AEP) (Ref. 8001)


Oyster adductor (Ref. 8001); Oyster gills, mantle a,d viscera (Ref. 8003)




17
N-Heptadecanoyl-4-hexadecasphingenine 2-aminoethylphosphonate (Ref. 8001)
PSP8003
Akira Hayashi
C17:0-d16:1-AEPn
C36H72O5N2P1 643.941 Download ChemDraw structure file


GC-EI-MS of TMS-Ceramide (C17:0-d16:1) (Ref. 8001); GC-EI-MS of TMS-CAEP (C17:0-d16:1-AEP) (Ref. 8001)


Oyster adductor (Ref. 8001) Oyster gills, mantle and viscera (Ref. 8003)




18
N-Octadecanoyl-4,8-sphingadienine 2-aminoethylphosphonate (Ref. 8001)
PSP8004
Akira Hayashi
C18:0-d18:2-AEPn
C38H74O5N2P1 669.978 Download ChemDraw structure file


GC-EI-MS of TMS-Ceramide (C18:0-d18:2) (Ref. 8001); GC-EI-MS-of TMS-CAEP (C18:0-d18:2-AEP) (Ref. 8001)


Oyster adductor (Ref. 8001) Oyster gills, mantle and viscera (Ref. 8003)




19
N-Octadecanoyl-4-sphingosine 2-aminoethylphosphonate (Ref. 8001)
PSP8005
Akira Hayashi
C18:0-d18:1-AEPn
C35H70O5N2P1 629.915 Download ChemDraw structure file


GC-EI-MS of TMS-Ceramide (C18:0-d18:1) (Ref. 8001); GC-EI-MS of TMS-CAEP (C18:0-d18:1-AEP) (Ref. 8001)


Oyster adductor (Ref. 8001); Oyster gills, mantle and viscera (Ref. 8003)




20
N-Hexadecanoyl 4-sphingosine 2-aminoethylphosphonate (Ref. 8003)
PSP8006
Akira Hayashi
C16:0-d18:1-AEPn
C36H72O5N2P1 643.941 Download ChemDraw structure file


GC-EI-MS of TMS-Ceramide (C16:0-d18:1) (Ref. 8001); GC-EI-MS of TMS-CAEPn (C16:0-d18:1-AEPn) (Ref. 8001)


Oyster adductor, mantle, gills and viscera (Ref. 8003)




21
N-Hexadecanoyl-4, 8-sphingadienine 2-aminoethylphosphonate (Ref. 8003)
PSP8007
Akira Hayashi
C16:0-d18:2-AEPn
C36H70O5N2P1 641.925 Download ChemDraw structure file


GC-EI-MS of TMS-Ceramide (C16:0-d18:2) (Ref. 8001); GC-EI-MS of TMS-CAEPn (C16:0-d18:2-AEPn) (Ref. 8001)


Oyster adductor, gills, mantle and viscera (Ref. 8003)




22
Ceramide 2-N-methylaminoethyl phosphonate (Ref. 8006/8007/8008/8009)
PSP8008
Akira Hayashi
CMAEPn
Download ChemDraw structure file

IR of CMAEPn from Turbo coenutus, pressed in KBr (Ref. 8007); IR of CMAEPn I and II (Ref. 8008)

GC-EI-MS of TMS-Ceramides (2-hydroxy fatty acids -phytosphingosine) derived from CMAEPn II (Ref. 8008);, GC-EI-MS of TMS-ceramide (Normal fatty acids-dihydroxy long-chain bases) (Ref. 8009)

TLC of CMAEPn I, II, and III (Ref. 8008/8009)
Turbo cornutus (Ref. 8008/8009); Viscera of Turbo cornutus (Ref. 8007); Protozoa, Tetrahymena pyriformis W (++) (Ref. 8006/8010/8019); Protozoa, Tetrahymena pyriformis WH-14 (+) (Ref. 8006/8011/8019); Mollusca, Liolophura japonica (+) (Ref. 8006/8012/8019); Mollusca, Turbo cornutus, muscle (+++), viscera (+++) (Ref. 8006/8012/8019); Mollusca, Monodonta labio (+++) (Ref. 8006/8012/8019); Mollusca, Tegli lischkei (++) (Ref. 8006/8012/8019); Mollusca, Hiriopsis schlegelli, ova (+) (Ref. 8006/8013/8019), spermatozoa (+) (Ref. 8006/8014/8012/8019); Coelenterata, Metridium senile (+) (Ref. 8006/8018/8019); Land snail, Euhadra hickonis (Ref. 8005)



Fatty acid composition(Ref. 8007/8008/8009); Long chain base composition (Ref. 8008/8009)
23
N-Hexadecanoyl-hexadecasphinga-4-enine 2-N-methylaminoethylphosphonate (Ref. 8009)
PSP8009
Akira Hayashi
C16:0-d16:1-MAEPn
C35H70O5N2P1 629.915 Download ChemDraw structure file


GC-EI-MS of TMS-Ceramide (C16:0-d16:1) (Ref. 8009)


Viscera of Turbo cornutus (Ref. 8009)




24
N-Hexadecanoyl heptadeca-4-sphingenine 2-N-methylaminoethylphosphonate (Ref. 8009)
PSP8010
Akira Hayashi
C16:0-d17:1-MAEPn
C36H72O5N2P1 643.941 Download ChemDraw structure file


GC-EI-MA of TMS-Ceramide (C16:0-d17:1) (Ref. 8009)


Viscera of Turbo Cornutus (Ref. 8009)




25
N-Hexadecanoyl branched sphingosine 2-N-methylaminoethylphosphonate (Ref. 8009)
PSP8011
Akira Hayashi
C16:0-br-d18:1-MAEPn
C37H74O5N2P1 657.968 Download ChemDraw structure file


GC-EI-MS of TMS-Ceramide (C16:0-br-d18:1) (Ref. 8009)


Viscera of Turbo Cornutus (Ref. 8009)




26
N-Hexadecanoylsphingosine 2-N-methylaminoethylphosphonate (Ref. 8009)
PSP8012
Akira Hayashi
C16:0-d18:1-MAEPn
C37H74O5N2P1 657.968 Download ChemDraw structure file


GC-EI-MS of TMS-ceramide (C16:0-br-d18:1) (Ref. 8009)


Viscera of Turbo cornutus (Ref. 8009)




27
N-Hexadecanoyl sphingadienine 2-N-methylaminoethylphosphonate (Ref. 8009)
PSP8013
Akira Hayashi
c16:0-d18:2-MAEPn
C37H72O5N2P1 655.952 Download ChemDraw structure file


GC-EI-MS- of TMS-Ceramide (C16:0-d18:1) (Ref. 8009)


Viscera of Turbo cornutus (Ref. 8009)




28
N-Hexadecanoyldocosasphingadienine 2-N-methylaminoethylphosphonate (Ref. 8009)
PSP8014
Akira Hayashi
C16:0-d22:2-MAEPn
C41H80O5N2P1 712.058 Download ChemDraw structure file


GC-EI-MS of TMS-Ceramide (C16:0-d22:2) (Ref. 8009)


Viscera of Turbo cornutus (Ref. 8009)




29
N-2-Hydroxyhexadecanoylphytosphingosine 2-N-methylaminoethylphosphonate (Ref. 8008)
PSP8015
Akira Hayashi
h-C16:0-t18:0-MAEPn
C37H77O7N2P1 692.990 Download ChemDraw structure file


GC-EI-MS of TMS-ceramide (h-C16:0-t18:0) (Ref. 8008)


Viscera of Turbo cornutus (Ref. 8008)




30
N-2-hydroxyhexadecanoyl-4-hydroxynonadecasphinganine 2-N-methyaminoethylphosphonate (Ref. 8008)
PSP8016
Akira Hayashi
h-C16:0-t19:0-MAEPn
C38H79O7N2P1 707.017 Download ChemDraw structure file


GC-EI-MS of TMS-Ceramide (h-C16:0-t19:0) (Ref. 8008)


Viscera of Turbo cornutus (Ref. 8008)




31
N-2-Hydroxyhexadecanoyl-4-hydroxydocosasphingenine 2-N-methylaminoethylphosphonate (Ref. 8008)
PSP8017
Akira Hayashi
h-C16:0-t22:1-MAEPn
C41H83O7N2P1 747.081 Download ChemDraw structure file


GC-EI-MS of TMS-Ceramide (h-C16:0-t22:1) (Ref. 8008)


ViscerA of Turbo cornutus (Ref. 8008)





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