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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 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)Download (PDF)
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

General function:
Involved in hydrolase activity
Specific function:
Converts sphingomyelin to ceramide. Also has phospholipase C activities toward 1,2-diacylglycerolphosphocholine and 1,2-diacylglycerolphosphoglycerol. Isoform 2 and isoform 3 have lost catalytic activity.
Gene Name:
SMPD1
Uniprot ID:
P17405
Molecular weight:
69935.53
General function:
Involved in galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase activity
Specific function:
Involved in the biosynthesis of L2/HNK-1 carbohydrate epitope on glycoproteins. Can also play a role in glycosaminoglycan biosynthesis. Substrates include asialo-orosomucoid (ASOR), asialo-fetuin, and asialo-neural cell adhesion molecule. Requires sphingomyelin for activity: stearoyl-sphingomyelin was the most effective, followed by palmitoyl-sphingomyelin and lignoceroyl-sphingomyelin. Activity was demonstrated only for sphingomyelin with a saturated fatty acid and not for that with an unsaturated fatty acid, regardless of the length of the acyl group (By similarity).
Gene Name:
B3GAT1
Uniprot ID:
Q9P2W7
Molecular weight:
38255.675
General function:
Involved in catalytic activity
Specific function:
Converts sphingomyelin to ceramide. Also has phospholipase C activity toward palmitoyl lyso-phosphocholine. Does not appear to have nucleotide pyrophosphatase activity.
Gene Name:
ENPP7
Uniprot ID:
Q6UWV6
Molecular weight:
51493.415
General function:
Involved in metal ion binding
Specific function:
Converts sphingomyelin to ceramide. Hydrolyze 1-acyl-2-lyso-sn-glycero-3-phosphocholine (lyso-PC) and 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholine (lyso-platelet-activating factor). The physiological substrate seems to be Lyso-PAF.
Gene Name:
SMPD2
Uniprot ID:
O60906
Molecular weight:
47645.29
General function:
Involved in lipid metabolic process
Specific function:
Saposin-D is a specific sphingomyelin phosphodiesterase activator (EC 3.1.4.12)
Gene Name:
PSAP
Uniprot ID:
P07602
Molecular weight:
58112.1
General function:
Involved in calcium ion binding
Specific function:
Hydrolyzes the phosphatidylinositol 4,5-bisphosphate (PIP2) to generate 2 second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3). DAG mediates the activation of protein kinase C (PKC), while IP3 releases Ca(2+) from intracellular stores. Essential for trophoblast and placental development. May participate in cytokinesis by hydrolyzing PIP2 at the cleavage furrow.
Gene Name:
PLCD3
Uniprot ID:
Q8N3E9
Molecular weight:
89257.54
General function:
Involved in metal ion binding
Specific function:
Catalyzes the hydrolysis of sphingomyelin to form ceramide and phosphocholine. Ceramide mediates numerous cellular functions, such as apoptosis and growth arrest, and is capable of regulating these 2 cellular events independently. Also hydrolyzes sphingosylphosphocholine. Regulates the cell cycle by acting as a growth suppressor in confluent cells. Probably acts as a regulator of postnatal development and participates in bone and dentin mineralization.
Gene Name:
SMPD3
Uniprot ID:
Q9NY59
Molecular weight:
71080.1
General function:
Involved in metal ion binding
Specific function:
Catalyzes the hydrolysis of membrane sphingomyelin to form phosphorylcholine and ceramide.
Gene Name:
SMPD4
Uniprot ID:
Q9NXE4
Molecular weight:
86192.575
General function:
Involved in catalytic activity
Specific function:
Non-lysosomal glucosylceramidase that catalyzes the conversion of glucosylceramide to free glucose and ceramide. Involved in sphingomyelin generation and prevention of glycolipid accumulation. May also catalyze the hydrolysis of bile acid 3-O-glucosides, however, the relevance of such activity is unclear in vivo.
Gene Name:
GBA2
Uniprot ID:
Q9HCG7
Molecular weight:
104648.13
General function:
Involved in sphingomyelin biosynthetic process
Specific function:
Not Available
Gene Name:
SAMD8
Uniprot ID:
Q96LT4
Molecular weight:
48320.2