スフィンゴシン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/08/13 16:00:51」(JST)
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Sphingosine
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Names |
IUPAC name
(2S,3R)-2-aminooctadec-4-ene-1,3-diol
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Identifiers |
CAS Registry Number
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123-78-4 Y |
ChEBI |
CHEBI:16393 N |
ChEMBL |
ChEMBL67166 Y |
ChemSpider |
4444047 Y |
InChI
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InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1 Y
Key: WWUZIQQURGPMPG-KRWOKUGFSA-N Y
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InChI=1/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1
Key: WWUZIQQURGPMPG-KRWOKUGFBW
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IUPHAR/BPS
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2452 |
Jmol-3D images |
Image |
PubChem |
5280335 |
SMILES
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CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
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Properties |
Chemical formula
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C18H37NO2 |
Molar mass |
299.50 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N verify (what is: Y/N?) |
Infobox references |
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Sphingosine (2-amino-4-octadecene-1,3-diol) is an 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids, a class of cell membrane lipids that include sphingomyelin, an important phospholipid.
Contents
- 1 Functions
- 2 Biosynthesis
- 3 See also
- 4 References
- 5 Additional images
- 6 External links
Functions
Sphingosine can be phosphorylated in vivo via two kinases, sphingosine kinase type 1 and sphingosine kinase type 2. This leads to the formation of sphingosine-1-phosphate, a potent signaling lipid.
Sphingolipid metabolites, such as ceramide, sphingosine and sphingosine-1-phosphate, are lipid signaling molecules involved in diverse cellular processes.
Biosynthesis
Sphingosine is synthesized from palmitoyl CoA and serine in a condensation required to yield dehydrosphingosine.
Dehydrosphingosine is then reduced by NADPH to dihydrosphingosine (sphinganine), and finally oxidized by FAD to sphingosine.
There is no direct route of synthesis from sphinganine to sphingosine; it has to be acylated first to dihydroceramide, which is then dehydrogenated to ceramide. Sphingosine is formed via degradation of sphingolipid in the lysosome.
See also
- Dimethylsphingosine
- Fingolimod
References
- Radin N (2003). "Killing tumours by ceramide-induced apoptosis: a critique of available drugs". Biochem J 371 (Pt 2): 243–56. doi:10.1042/BJ20021878. PMC 1223313. PMID 12558497. article
- Carter, H. E., F. J. Glick, W. P. Norris, and G. E. Phillips. 1947. Biochemistry of the sphingolipides. III. Structure of sphingosine. J. Biol. Chem. 170: 285–295
Additional images
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General structures of sphingolipids
External links
- Sphingosine at the US National Library of Medicine Medical Subject Headings (MeSH)
Amines, alcohols: amino alcohols
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- Ethanolamine
- Heptaminol
- Isoetarine
- Norepinephrine
- Propanolamine
- Sphingosine
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Glycoconjugates, lipids and glycolipids: sphingolipids and glycosphingolipids, and metabolic intermediates
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Ceramide |
- Cerebroside
- Galactocerebroside
- Glucocerebroside
- Lactosylceramide
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Ganglioside
pathway |
From ganglioside
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From globoside
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From sphingomyelin
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From sulfatide
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To sphingosine
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Other |
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Index of inborn errors of metabolism
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Description |
- Metabolism
- Enzymes and pathways: citric acid cycle
- pentose phosphate
- glycoproteins
- glycosaminoglycans
- phospholipid
- cholesterol and steroid
- sphingolipids
- eicosanoids
- amino acid
- urea cycle
- nucleotide
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Disorders |
- Citric acid cycle and electron transport chain
- Glycoprotein
- Proteoglycan
- Fatty-acid
- Phospholipid
- Cholesterol and steroid
- Eicosanoid
- Amino acid
- Purine-pyrimidine
- Heme metabolism
- Symptoms and signs
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Treatment |
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Index of biochemical families
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Carbohydrates |
- Alcohols
- Glycoproteins
- Glycosides
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Lipids |
- Eicosanoids
- Fatty acids
- Glycerides
- Phospholipids
- Sphingolipids
- Steroids
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Nucleic acids |
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Proteins |
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Other |
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Lysophospholipid signaling
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Receptor
(ligands) |
LPA |
- Agonists: 1-Oleoyl-LPA
- 1-Palmitoyl-LPA
- GRI-977143
- LPA
- OMPT
- Antagonists: H2L-5186303
- H2L-5765834
- Ki-16425
- TC-LPA5 4
- VPC-32183
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S1P |
- Agonists: Ceralifimod
- CS-2100
- CYM-5442
- CYM-5520
- CYM 5541
- CYM-50260
- CYM-50308
- Dihydro-S1P (sphinganine 1-phosphate)
- Fingolimod
- Fingolimod phosphate
- KRP-203
- Phyto-S1P
- Ponesimod
- RP-001
- RP-002
- RPC-1063
- SEW-2871
- Siponimod
- S1P
- SPC
- TC-G 1006
- TC-SP 14
- W-061
- XAX-162
- Antagonists: CS-0777
- CYM-50358
- JTE-013
- TY-52156
- VPC-23019
- W-146
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Enzyme
(inhibitors) |
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Others |
- Precursors: LPA: LPC; S1P: Palmitoyl-CoA
- Serine
- 3-Ketosphinganine (dehydrosphingosine)
- Dihydrosphingosine (sphinganine)
- Dihydroceramide
- Ceramide
- Sphingosine
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UpToDate Contents
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English Journal
- The role of the sphingosine-1-phosphate signaling pathway in osteocyte mechanotransduction.
- Zhang JN1, Zhao Y1, Liu C1, Han ES1, Yu X2, Lidington D3, Bolz SS4, You L5.
- Bone.Bone.2015 Oct;79:71-8. doi: 10.1016/j.bone.2015.05.017. Epub 2015 May 16.
- Osteocytes are proposed to be the mechanosensory cells that translate mechanical loading into biochemical signals during the process of bone adaptation. The lipid mediator sphingosine-1-phosphate (S1P) has been reported to play a role in the mechanotransduction process of blood vessels and also in t
- PMID 25988659
- Lysophospholipids in coronary artery and chronic ischemic heart disease.
- Abdel-Latif A1, Heron PM, Morris AJ, Smyth SS.
- Current opinion in lipidology.Curr Opin Lipidol.2015 Oct;26(5):432-7. doi: 10.1097/MOL.0000000000000226.
- PURPOSE OF REVIEW: The bioactive lysophospholipids, lysophosphatidic acid (LPA) and sphingosine 1 phosphate (S1P), have potent effects on blood and vascular cells. This review focuses their potential contributions to the development of atherosclerosis, acute complications such as acute myocardial in
- PMID 26270808
- Increased SPHK2 Transcription of Human Colon Cancer Cells in Serum-Depleted Culture: The Involvement of CREB Transcription Factor.
- Mizutani N1, Omori Y1, Tanaka K1, Ito H1, Takagi A1, Kojima T1, Nakatochi M2, Ogiso H3, Kawamoto Y4, Nakamura M5, Suzuki M6, Kyogashima M7, Tamiya-Koizumi K1, Nozawa Y8, Murate T1.
- Journal of cellular biochemistry.J Cell Biochem.2015 Oct;116(10):2227-38. doi: 10.1002/jcb.25173.
- Sphingosine kinases (SPHK) are important to determine cells' fate by producing sphingosine 1-phosphate. Reportedly, exogenous SPHK2 overexpression induces cell cycle arrest or cell death. However, the regulatory mechanism of SPHK2 expression has not been fully elucidated. Here, we analyzed this issu
- PMID 25808826
Japanese Journal
- Simultaneous Quantification of Sphingolipids in Small Quantities of Liver by LC-MS/MS (Mass Spectrometry) -- (Special Issue : The 62nd MSSJ Annual Conference)
- Journal of the Mass Spectrometry Society of Japan = 質量分析 63(2), 1-8, 2015-04
- NAID 40020425015
- Phosphatidylinositol 3-kinase class II α-isoform PI3K-C2α is required for transforming growth factor β-induced smad signaling in endothelial cells
- ISAC-1-4 Sphingosine kinase 1 as potential therapeutic target in epithelial ovarian cancer(Group 1 Oncology,IS Award Candidate,International Session)
Related Links
- Sphingosine definition, a basic unsaturated amino alcohol, C 1 8 H 3 3 (OH) 2 NH 2 , produced by the hydrolysis of sphingomyelin or gangliosides. See more. Thesaurus Translate Puzzles & Games Word of the Day Blog Apps by ...
- sphingosine [sfing´go-sēn] a basic amino alcohol present in sphingomyelin. sphin·go·sine (sfing'gō-sēn), The principal long-chain base found in sphingolipids. Synonym(s): , sphingol sphingosine /sphin·go·sine/ (sfing´go-sēn) a long ...
Related Pictures
![File:Sphingosine-2D-skeletal.png](https://1mg.info/0/g/4/1328.jpg)
![With sphingosine, the lipid that can be](https://1mg.info/0/g/4/1329.jpg)
![Sphingosine (4 sphingenine; 4-sphingenine)](https://1mg.info/0/g/4/1330.jpg)
![Biosynthesis of sphingosine -1-](https://1mg.info/0/g/4/1331.jpg)
![Sphingosine Sphingosine and](https://1mg.info/0/g/4/1332.jpg)
★リンクテーブル★
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- 英
- sphingosine
- 同
- スフィンゴール sphingol、スフィンゴシノール sphingosinol、スフィンゲニン sphingenine
- 関
- スフィンゴ脂質
[★]
スフィンゴシン-1-リン酸, スフィンゴシン一リン酸, S1P
[★]
スフィンゴシンキナーゼ
[★]
アシルスフィンゴシン