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Sphingosine information


Sphingosine
Skeletal formula of sphingosine
Space-filling model of the sphingosine molecule
Names
Preferred IUPAC name
(2S,3R,4E)-2-Aminooctadec-4-ene-1,3-diol
Identifiers
CAS Number
  • 123-78-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16393 ☒N
ChEMBL
  • ChEMBL67166 checkY
ChemSpider
  • 4444047 checkY
ECHA InfoCard 100.004.230 Edit this at Wikidata
IUPHAR/BPS
  • 2452
PubChem CID
  • 5280335
UNII
  • NGZ37HRE42 checkY
CompTox Dashboard (EPA)
  • DTXSID90861763 Edit this at Wikidata
InChI
  • 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 checkY
    Key: WWUZIQQURGPMPG-KRWOKUGFSA-N checkY
  • 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
SMILES
  • CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
Properties
Chemical formula
C18H37NO2
Molar mass 299.499 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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Infobox references

Sphingosine (2-amino-4-trans-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.

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Sphingosine

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important phospholipid. Sphingosine can be phosphorylated in vivo via two kinases, sphingosine kinase type 1 and sphingosine kinase type 2. This leads...

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Lipid signaling

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that hydrolyze the phosphocholine group from the sphingosine backbone. Alternatively, this sphingosine-derived lipid (sphingolipid) can be synthesized...

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S1PR1

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Sphingosine-1-phosphate receptor 1 (S1P receptor 1 or S1PR1), also known as endothelial differentiation gene 1 (EDG1) is a protein that in humans is encoded...

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Sphingosine cholinephosphotransferase

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enzymology, a sphingosine cholinephosphotransferase (EC 2.7.8.10) is an enzyme that catalyzes the chemical reaction CDP-choline + sphingosine ⇌ {\displaystyle...

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Sphingosine kinase

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from the precursor sphingolipid sphingosine. Sphingolipid metabolites, such as ceramide, sphingosine and sphingosine-1-phosphate, are lipid second messengers...

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Sphingolipid

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sphingoid bases, which are a set of aliphatic amino alcohols that includes sphingosine. They were discovered in brain extracts in the 1870s and were named after...

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Kinase

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coordinated for this purpose. Sphingosine kinase (SK) is a lipid kinase that catalyzes the conversion of sphingosine to sphingosine-1-phosphate (S1P). Sphingolipids...

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Etrasimod

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that is used for the treatment of ulcerative colitis. It is a selective sphingosine-1-phosphate (S1P) receptor modulator that modifies the activity of the...

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Sphingosine kinase 1

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Sphingosine kinase 1 is an enzyme that in humans is encoded by the SPHK1 gene. Sphingosine kinase 1 phosphorylates sphingosine to sphingosine-1-phosphate...

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Ceramide

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Ceramides are a family of waxy lipid molecules. A ceramide is composed of sphingosine and a fatty acid joined by an amide bond. Ceramides are found in high...

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SGPL1

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Sphingosine-1-phosphate lyase 1 is an enzyme that in humans is encoded by the SGPL1 gene. GRCh38: Ensembl release 89: ENSG00000166224 – Ensembl, May 2017...

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SPHK2

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kinase isozymes that catalyze the phosphorylation of sphingosine into sphingosine 1-phosphate. Sphingosine 1-phosphate mediates many cellular processes including...

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SGPP1

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Sphingosine-1-phosphate phosphatase 1 is an enzyme that in humans is encoded by the SGPP1 gene. ENSG00000285281 GRCh38: Ensembl release 89: ENSG00000126821...

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Fingolimod

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medication, used for the treatment of multiple sclerosis. Fingolimod is a sphingosine-1-phosphate receptor modulator, which sequesters lymphocytes in lymph...

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Membrane lipid

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Sphingosine is an amino alcohol that contains a long, unsaturated hydrocarbon chain. In sphingomyelin and glycolipids, the amino group of sphingosine...

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S1PR3

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Sphingosine-1-phosphate receptor 3 also known as S1PR3 is a human gene which encodes a G protein-coupled receptor which binds the lipid signaling molecule...

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S1PR2

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Sphingosine-1-phosphate receptor 2, also known as S1PR2 or S1P2, is a human gene which encodes a G protein-coupled receptor which binds the lipid signaling...

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Sphingomyelin

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head group, a sphingosine, and a fatty acid. It is one of the few membrane phospholipids not synthesized from glycerol. The sphingosine and fatty acid...

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Opaganib

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Opaganib (ABC294640) is a drug which acts as an inhibitor of the enzyme sphingosine kinase 2. It is under development as a potential treatment agent for...

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Siponimod

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Siponimod, sold under the brand name Mayzent, is a selective sphingosine-1-phosphate receptor modulator for oral use that is used for multiple sclerosis...

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S1PR5

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Sphingosine-1-phosphate receptor 5 also known as S1PR5 is a human gene which encodes a G protein-coupled receptor which binds the lipid signaling molecule...

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Ceramidase

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acids from ceramide, producing sphingosine (SPH) which in turn is phosphorylated by a sphingosine kinase to form sphingosine-1-phosphate (S1P). Ceramide...

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Biosynthesis

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group of a sphingosine backbone. These ceramides are synthesized from the acylation of sphingosine. The biosynthetic pathway for sphingosine is found below:...

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Ozanimod

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of relapsing multiple sclerosis and ulcerative colitis. It acts as a sphingosine-1-phosphate receptor (S1PR) agonist, sequestering lymphocytes to peripheral...

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