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Sphingophospholipid


DATA No : PSP6001 INFORMANT : Takehiko Yokomizo

NAME : sphingosine 1-phosphate

COMMON NAME:
SYMBOL: S1P/ SPP/ Sph-1-P
FORMULA: C18H38NO5P MOL.WT (average) : 379.472


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BIOLOGICAL ACTIVITY
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).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY: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.
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:ESI/MS (Ref. 4509).

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM
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).
GENETIC INFORMATION

NOTE

REFERENCES
[6001]
AUTHOR:Desai, N. N., Zhang, H., Olivera, A., Mattie, M. E., and Spiegel, S.
TITLE:Sphingosine-1-phosphate, a metabolite of sphingosine, increases phosphatidic acid levels by phospholipase D activation PubMed ID:1429659
JOURNAL:J Biol Chem.
VOL:267 PAGE : 23122-23128 (1992)
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[6002]
AUTHOR:Sadahira, Y., Ruan, F., Hakomori, S., and Igarashi, Y.
TITLE:Sphingosine 1-phosphate, a specific endogenous signaling molecule controlling cell motility and tumor cell invasiveness PubMed ID:1409683
JOURNAL:Proc Natl Acad Sci U S A.
VOL:89 PAGE : 9686-9690 (1992)
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[6003]
AUTHOR:Olivera, A., and Spiegel, S.
TITLE:Sphingosine-1-phosphate as second messenger in cell proliferation induced by PDGF and FCS mitogens PubMed ID:8413613
JOURNAL:Nature.
VOL:365 PAGE : 557-560 (1993)
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[6004]
AUTHOR:Mattie, M., Brooker, G., and Spiegel, S.
TITLE:Sphingosine-1-phosphate, a putative second messenger, mobilizes calcium from internal stores via an inositol trisphosphate-independent pathway PubMed ID:8106352
JOURNAL:J Biol Chem.
VOL:269 PAGE : 3181-3188 (1994)
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[6005]
AUTHOR:Wu, J., Spiegel, S., and Sturgill, T. W.
TITLE:Sphingosine 1-phosphate rapidly activates the mitogen-activated protein kinase pathway by a G protein-dependent mechanism PubMed ID:7744787
JOURNAL:J Biol Chem.
VOL:270 PAGE : 11484-11488 (1995)
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[6006]
AUTHOR:Cuvillier, O., Pirianov, G., Kleuser, B., Vanek, P. G., Coso, O. A., Gutkind, S., and Spiegel, S.
TITLE:Suppression of ceramide-mediated programmed cell death by sphingosine-1-phosphate PubMed ID:8657285
JOURNAL:Nature.
VOL:381 PAGE : 800-803 (1996)
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[6007]
AUTHOR:Lee, M. J., Van Brocklyn, J. R., Thangada, S., Liu, C. H., Hand, A. R., Menzeleev, R., Spiegel, S., and Hla, T.
TITLE:Sphingosine-1-phosphate as a ligand for the G protein-coupled receptor EDG-1 PubMed ID:9488656
JOURNAL:Science.
VOL:279 PAGE : 1552-1555 (1998)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.