Psychosine

Psychosine

Names
IUPAC name (2S,3R,4E)-2-Amino-3-hydroxyoctadec-4-en-1-yl β-D-galactopyranoside
Systematic IUPAC name (2R,3R,4S,5R,6R)-2-{[(2S,3R,4E)-2-Amino-3-hydroxyoctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Identifiers
CAS Number	2238-90-6^N
3D model (JSmol)	Interactive image
Beilstein Reference	52571
ChEBI	CHEBI:16874
ChemSpider	4444111
ECHA InfoCard	100.164.357
EC Number	636-571-3
KEGG	C01747
PubChem CID	5280458
CompTox Dashboard (EPA)	DTXSID60896981
InChI InChI=1S/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/b15-14+/t18-,19+,20+,21-,22-,23+,24+/m0/s1 Key: HHJTWTPUPVQKNA-PIIMIWFASA-N
SMILES CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)N)O
Properties
Chemical formula	C24H47NO7
Molar mass	461.640 g·mol^−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332
Precautionary statements	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Psychosine is a highly cytotoxic lipid that accumulates in the nervous system in the absence of galactosylceramidase.[1]

Chemically, it is a galactoside of sphingosine.

References

1. Hawkins-Salsbury, J. A.; Parameswar, A. R.; Jiang, X; Schlesinger, P. H.; Bongarzone, E; Ory, D. S.; Demchenko, A. V.; Sands, M. S. (2013). "Psychosine, the cytotoxic sphingolipid that accumulates in globoid cell leukodystrophy, alters membrane architecture". The Journal of Lipid Research. 54 (12): 3303–3311. doi:10.1194/jlr.M039610. PMC 3826678. PMID 24006512.