Structure Database (LMSD)

Common Name
Sphingosine
Systematic Name
Sphing-4-enine
Synonyms
  • Sphingosine
  • 4-Sphingenine
  • D-erythro-Sphingosine
  • (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol
  • 4-trans-Sphingenine
  • Sphingenine
  • 2S-Amino-4E-octadecene-1,3R-diol
LM ID
LMSP01010001
Status
Active
Exact Mass
Calculate m/z
299.282429
Formula
C18H37NO2
Abbrev
SPB 18:1;O2
Show lipids differing only in stereochemistry/bond geometry
View MoNA MS spectra
Download as...
MDLMOL SDF CSV TSV
MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".

Main

Classification

Category
Main Class
Sub Class
Sphingolipids [SP]
Sphingoid bases [SP01]
Sphing-4-enines (Sphingosines) [SP0101]

String Representations

InChiKey (Click to copy)
WWUZIQQURGPMPG-KRWOKUGFSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
OC[C@]([H])(N)[C@]([H])(O)/C=C/CCCCCCCCCCCCC

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
Pubmed ID: 20671299

Other Databases

Wikipedia
Sphingosine
KEGG ID
C00319
HMDB ID
HMDB00252
CHEBI ID
16393
PubChem CID
5280335
SwissLipids ID
SLM:000000412
Cayman ID
10007907

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 345.90
Topological Polar Surface Area 66.48
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 2
logP 4.78
Molar Refractivity 92.80

Reactions

Click on an edge to display the reaction(s).
Reactions graph legend

Admin

Created at
-
Updated at
-