Structure via PubChem · Public domain (PubChem)
sphingosine 1-phosphate
Sign in to saveAlso known as S1P, (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 1-(dihydrogen phosphate), sphingosine-1-phosphate, C18-Sphingosine 1-phosphate, Sphingosine 1-phosphic acid, (2-amino-3-hydroxy-octadec-4-enoxy)phosphonic acid, D-erythro-sphingosine 1-phosphate, D-Erythro-Sphingosine-1-phosphate
Sphingosine-1-phosphate (S1P) is a signaling sphingolipid, also known as lysosphingolipid. It is also referred to as a bioactive lipid mediator. Sphingolipids at large form a class of lipids characterized by a particular aliphatic aminoalcohol, which is sphingosine.
Chemical data
- Formula
- C18H38NO5P
- Molecular weight
- 379.5 g/mol
- IUPAC name
- [(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enyl] dihydrogen phosphate
- SMILES
- CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(O)O)N)O
- InChIKey
- DUYSYHSSBDVJSM-KRWOKUGFSA-N
- XLogP
- 1.9
- Polar surface area
- 113 Ų
- H-bond donors
- 4
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
9,820 papersvia PubMed
Wikidata facts
- Mass
- 379.249
Show 4 more facts
- chemical formula
- C₁₈H₃₈NO₅P
- isomeric SMILES
- CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(O)O)N)O
- canonical SMILES
- CCCCCCCCCCCCCC=CC(C(COP(=O)(O)O)N)O
- found in taxon
- Phaseolus vulgaris
via Wikidata · CC0
~7 min read
Encyclopedic overview
12 sectionsContents
- Production
- Metabolism and degradation
- Function
- Clinical significance
- As a drug
- As a drug target
- S1P receptor(s) as a drug target
- S1P receptor modulators
- See also
- Notes
- References
- Further reading
Sphingosine-1-phosphate (S1P) is a signaling sphingolipid, also known as lysosphingolipid. It is also referred to as a bioactive lipid mediator. Sphingolipids at large form a class of lipids characterized by a particular aliphatic aminoalcohol, which is sphingosine.
==Production== S1P is formed from ceramide, which is composed of a sphingosine and a fatty acid. Ceramidase, an enzyme primarily present in plasma membrane, will convert ceramide to sphingosine. Sphingosine is then phosphorylated by sphingosine kinase (SK) isoenzymes. There are two identified mammalian isoenzymes: SK1 and SK2. These two enzymes have different tissue distribution. SK1 is highly expressed in spleen, lung and leukocytes, while SK2 is highly expressed in liver and kidney. SK2 is located mainly in the mitochondrion, nucleus and the endoplasmic reticulum, whereas SK1 is mainly located in cytoplasm and the cell membrane.
Excerpted from Wikipedia’s “sphingosine 1-phosphate” article, available under the CC BY-SA 4.0 licence.