Record Information
Version3.6
Creation Date2007-05-23 11:19:36 UTC
Update Date2013-02-09 00:14:52 UTC
HMDB IDHMDB06482
Secondary Accession Numbers
  • HMDB12083
Metabolite Identification
Common NameLysoSM(d18:1)
DescriptionD-erythro-sphingosylphosphorylcholine is an intermediate in Sphingolipid metabolism. D-erythro-sphingosylphosphorylcholine is the 5th to last step in the synthesis of Digalactosylceramidesulfate and is converted from Sphingosine via the enzyme sphingosine cholinephosphotransferase ( EC 2.7.8.10). It is then converted to Sphingomyelin via the enzyme sphingosine N-acyltransferase (EC 2.3.1.24).
Structure
Thumb
Synonyms
  1. C18-Sphingosine phosphocholine
  2. D-Erythro-sphingosylphosphorylcholine
  3. Lysosphingomyelin
  4. SM(d18:1/0:0)
  5. Sphing-4-enine-1-phosphocholine
  6. Sphingenyl-1-phosphorylcholine
  7. Sphingomyelin(d18:1/0:0)
  8. Sphingosyl-phosphocholine
Chemical FormulaC23H50N2O5P
Average Molecular Weight465.6273
Monoisotopic Molecular Weight465.345734232
IUPAC Name{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid
Traditional IUPAC Name[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy(2-(trimethylaminio)ethoxy)phosphinic acid
CAS Registry Number1670-26-4
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(=O)(O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/p+1/b18-17+/t22-,23+/m0/s1
InChI KeyJLVSPVFPBBFMBE-HXSWCURESA-O
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSphingolipids
Sub ClassLysosphingomyelins and Lysoglycosphingolipids
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • 1,2 Aminoalcohol
  • Acyclic Alkene
  • Allyl Alcohol
  • Choline
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphocholine
  • Phosphoethanolamine
  • Phosphoric Acid Ester
  • Primary Aliphatic Amine (Alkylamine)
  • Quaternary Ammonium Salt
  • Secondary Alcohol
Direct ParentLysosphingomyelins and Lysoglycosphingolipids
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility8.420E-04 g/LALOGPS
logP1.3ALOGPS
logP-0.24ChemAxon
logS-5.8ALOGPS
pKa (strongest acidic)1.83ChemAxon
pKa (strongest basic)9.68ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count3ChemAxon
polar surface area102.01ChemAxon
rotatable bond count21ChemAxon
refractivity141.18ChemAxon
polarizability55.37ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023932
KNApSAcK IDNot Available
Chemspider ID4444221
KEGG Compound IDC03640
BioCyc IDNot Available
BiGG ID2704995
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06482
Metagene LinkHMDB06482
METLIN IDNot Available
PubChem Compound5280613
PDB IDSPU
ChEBI ID52897
References
Synthesis ReferenceSphingomyelin, intermediates thereof and methods for preparation of same. Rochlin, Elimelech; Hildesheim, Jean; Berlin, Alisa. (Biolab Ltd., Israel). PCT Int. Appl. (2005), 39 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Morita SY, Soda K, Teraoka R, Kitagawa S, Terada T: Specific and sensitive enzymatic measurement of sphingomyelin in cultured cells. Chem Phys Lipids. 2012 Jul;165(5):571-6. doi: 10.1016/j.chemphyslip.2012.06.003. Epub 2012 Jun 19. Pubmed: 22727956

Enzymes

Gene Name:
SMPD1
Uniprot ID:
P17405
Gene Name:
SMPD2
Uniprot ID:
O60906
Gene Name:
PSAP
Uniprot ID:
P07602
Gene Name:
SMPD3
Uniprot ID:
Q9NY59
Gene Name:
SMPD4
Uniprot ID:
Q9NXE4
Gene Name:
GBA2
Uniprot ID:
Q9HCG7