Psychosine
Basic information
- CAS
2238-90-6- Standard SMILES
CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O- InChIKey
HHJTWTPUPVQKNA-PIIMIWFASA-N- Molecular formula
- C24H47NO7
- Average molar mass
- 461.6 g/mol
- Monoisotopic mass
- 461.33525284
Overview
Psychosine is a glycosylsphingoid consisting of sphingosine having a beta-D-galactosyl residue attached at the 1-position. It has a role as a human metabolite. It is functionally related to a sphingosine and a sphing-4-enine. It is a conjugate base of a psychosine(1+).
Names & identifiers
- Preferred name
- Psychosine
- IUPAC
- (2R,3R,4S,5R,6R)-2-[(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
- English name
- PSYCHOSINE
- Molecular formula
- C24H47NO7
- Molecular weight
- 461.63
Names & synonyms
PSYCHOSINE2238-90-6Sphingosine galactoside1-beta-D-galactosphingosine1-beta-D-Galactosylsphingosineerythro-PsychosineO-GalactosylsphingosineCHEBI:16874BG5A25U68L(2R,3R,4S,5R,6R)-2-[(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol1-beta-D-galactosyl-sphing-4-eninebeta-D-Galactopyranoside, 2-amino-3-hydroxy-4-octadecenyl, (R-(R*,S*-(E)))-
Show more names
PSYCHOSINPSYCHOSINE(RG)LYSO-CEREBROSIDEPSYCHOSINE USP/EP/BPPsychosine (free amine)LYSO-CERAMIDEGALACTOSIDE
Galactoside, SphingosineDTXSID60896981(2R,3R,4S,5R,6R)-2-((E,2S,3R)-2-amino-3-hydroxyoctadec-4-enoxy)-6-(hydroxymethyl)oxane-3,4,5-triolRefChem:177063DTXCID001326409Galactosylsphingosinebeta-psychosine1-O-beta-D-galactopyranosylsphingosine
Database identifiers
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 146 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 18
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 479
Experimental & physicochemical properties
Lipids
Lipids -> Sphingolipids [SP] -> Basic glycosphingolipids [SP07]
Lipids -> Sphingolipids [SP] -> Amphoteric glycosphingolipids [SP08]
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 190 °C · 190 °C (decomp)
- Boiling point
- 664.3 · 664.3±55.0 °C(Predicted)
- Density
- 1.14 · 1.14±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform/Methanol/DI water (5:1:0.1): soluble; Ethanol: soluble
- form
- lyophilized powder
- pka
- 11.74 · 11.74±0.45(Predicted)
- color
- White to off-white
- InChIKey
- HHJTWTPUPVQKNA-PIIMIWFASA-N
- SMILES
- [H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@](N)([H])CO[C@H](O1)[C@H](O)[C@@H](O)[C@H]([C@H]1CO)O
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Health EffectsChronically high levels of psychosine are associated with Globoid Cell Leukodystrophy.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- wgk
- 3
- risk_code
- 20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS06,GHS08
- hazard_code
- Xn
- safety_code
- 36
- Storage Class
- 3 - Flammable liquids
- Hazard statements
- H225-H301+H311+H331-H370
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Chemistry & industry
Pharmacology
Tissue LocationsBrain
Cellular LocationsExtracellular
Applications
DescriptionGalactosylsphingosine is a bioactive sphingolipid. It potentiates LPS-induced production of inflammatory cytokines, decreases the mitochondrial membrane potential, and induces cell death in mouse astrocytes, effects that can be reversed by the sphingosine-1-phosphate receptor agonist FTY720 phosphate . Galactosylsphingosine (0.1 and 1 μM) induces demyelination of mouse cerebellar slices. It inhibits PDGF-induced translocation of PKC to the cell surface and induces apoptosis in MO3.13 oligodendrocytes. Galactosylsphingosine (10 and 15 μM) inhibits gene transcription mediated by peroxisome proliferator-activated receptor α (PPARα) in reporter assays using C6 glial cells. Levels of galactosylsphingosine are increased in postmortem brain from patients with Krabbe disease, a lysosomal storage disorder characterized by a β-galactosylceramidase deficiency.[Matreya, LLC. Catalog No. 1305]
UsesPsychosine is a cationic lysosphingolipid that displays neuroprotective effects against quisqualate.
General DescriptionGalactosyl(β) Sphingosine (d18:1) is a substrate for the enzyme endoglycoceramidase I (EGCase I). It has sphingosine backbone with galactose attached to it and is a brain glycospingolipid.
Additional notes
DefinitionChEBI: A glycosylsphingoid consisting of sphingosine having a beta-D-galactosyl residue attached at the 1-position.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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