Sphingosyl-phosphorylcholine

HCID 5263

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Basic information

CAS: 1670-26-4
Standard SMILES: CCCCCCCCCCCCCC=CC(O)C(N)COP(=O)([O-])OCC[N+](C)(C)C
InChIKey: JLVSPVFPBBFMBE-UHFFFAOYSA-N
Molecular formula: C23H49N2O5P
Average molar mass: 464.6 g/mol
Monoisotopic mass: 464.33790967

Names & identifiers

Preferred name: Sphingosyl-phosphorylcholine
IUPAC: (2-amino-3-hydroxyoctadec-4-enyl) 2-(trimethylazaniumyl)ethyl phosphate
English name: Sphingosylphosphorylcholine
Molecular formula: C23H49N2O5P
Molecular weight: 464.62

Names & synonyms

Rac-Sphingosylphosphorylcholinesphingosyl-phosphorylcholineSCHEMBL195431orb1693085DTXSID402744602-Amino-3-hydroxyoctadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphateSphingosylphosphorylcholine (lyso-sphingomyelin)SPCMGC119002D-ERYTHRO-SPCLyso SM (d18:1)LYSO-SPHINGOMYELIN

Show more names

urocortin 3 (stresscopin)Lyso-Sphingomyelin (d18:1)spingosyl-phosphorylcholineSphingosylphosphorylcholineSphingenyl-1-phosphorylcholine

Database identifiers

CAS: 1670-26-4
PubChem CID: 5263
DTXSID: DTXSID40274460

Properties

Computed structural properties

XLogP: 4.7
Topological polar surface area: 105 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 6
Rotatable bonds: 21
Heavy atoms: 31
Formal charge: 0
Complexity: 489

Physicochemical properties

Melting point: 90 · 90-102°C
storage temp.: -20 °C · -20°C
solubility: chloroform/methanol (2:1): complete10 mg/ml, clear to slightly hazy, colorless to light yellow
form: powder
color: light yellow
biological source: goat
BRN: 7342520 · 7342520
InChIKey: JLVSPVFPBBFMBE-HXSWCURESA-N
SMILES: [H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(N)COP([O-])(OCC[N+](C)(C)C)=O
UNSPSC Code: 12352211 · 12352211
NACRES: 85 · NA.85
WGK Germany: 3 · 3
F: 1 · 1-8-10
Storage Class: 13 · 13 - Non Combustible Solids

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F: 1-8-10
wgk: 3
Storage Class: 13 - Non Combustible Solids

Chemistry & industry

Applications · 4 items

UsesInvolved in cell regulation, and transmembrane signaling. A putative lipid second messenger, connected via Protein Kinase C to the phosphatidylinositol-derived second messengers for signal transduction.

UsesNeurotrophic effects of Sphingosylphosphorylcholine were studied in cerebellar granule neurons of mice and PC-12 cells.

UsesLyso SM (d18:1) has been used: to study its effect on the skeletal muscle ryanodine receptor (RyR1), in the presence and absence of calmodulin through single channel recordings in planar lipid bilayersas an inhibitor of Ca2+ sensor calmodulin (CaM)as a standard in circular dichroism (CD) spectroscopy to determine lipid selectivity of the lipid-peptide interactions

General DescriptionLyso SM (d18:1), also known as sphingosylphosphorylcholine (SPC), is a bioactive lipid molecule. This lysophospholipid is present in normal blood plasma, ascites and various tissues.

Suppliers39 total

阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]

上海钰博生物科技有限公司021-60514606 18321282235 · [email protected]

宜昌众意泰贸易有限公司0717-6449896 13886658719 · [email protected]

Aladdin Scientific[email protected]

武汉易泰科技有限公司上海分公司18930552037 · [email protected]

Additional notes · 1 item

DefinitionChEBI: Sphingosine-1-phosphocholine is a phosphosphingolipid consisting of sphingosine having a phosphocholine moiety attached to its primary hydroxyl group. It is a phosphosphingolipid, a member of phosphocholines and an ammonium betaine. It is functionally related to a sphingosine. It is a conjugate base of a sphingosylphosphocholine acid and a sphingosine-1-phosphocholine(1+).

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