Structure via PubChem · Public domain (PubChem)
sphingosine
Sign in to saveAlso known as cerebroside, D-erythrosphingosine, D-sphingosine, (4E)-sphing-4-enine, (2S,3R,4E)-2-amino-4-octadecene-1,3-diol, (4E)-sphingenine, trans-4-sphingenine, (E)-2-amino-4-octadecan-1,3-diol
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.
Chemical data
- Formula
- C18H37NO2
- Molecular weight
- 299.5 g/mol
- IUPAC name
- (E,2S,3R)-2-aminooctadec-4-ene-1,3-diol
- SMILES
- CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
- InChIKey
- WWUZIQQURGPMPG-KRWOKUGFSA-N
- XLogP
- 5.3
- Polar surface area
- 66.5 Ų
- H-bond donors
- 3
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
19,280 papers- Sphingosine 1-phosphate and cancer.Advances in biological regulation · 2018
- Sphingosine-1-Phosphate and Macrophage Biology-How the Sphinx Tames the Big Eater.Frontiers in immunology · 2019
- Drugging sphingosine kinases.ACS chemical biology · 2015
- Sphingosine in apoptosis signaling.Biochimica et biophysica acta · 2002
- Can another lipid, sphingosine-1-phosphate, treat atherosclerosis?Cardiovascular research · 2024
via PubMed
Wikidata facts
- Mass
- 299.282
Show 5 more facts
- Commons category
- Sphingosine
- chemical formula
- C₁₈H₃₇NO₂
- canonical SMILES
- CCCCCCCCCCCCCC=CC(C(CO)N)O
- isomeric SMILES
- CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
- melting point
- 67
via Wikidata · CC0
~1 min read
Article
6 sectionsContents
- Functions
- Biosynthesis
- Gallery
- See also
- Literature
- External links
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.
==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.