Human Metabolome Database Version 3.5

Showing metabocard for LysoSM(d18:1) (HMDB06482)

Record Information
Version 3.5
Creation Date 2007-05-23 05:19:36 -0600
Update Date 2013-02-08 17:14:52 -0700
HMDB ID HMDB06482
Secondary Accession Numbers
  • HMDB12083
Metabolite Identification
Common Name LysoSM(d18:1)
Description D-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C23H50N2O5P
Average Molecular Weight 465.6273
Monoisotopic Molecular Weight 465.345734232
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 Number 1670-26-4
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 Key JLVSPVFPBBFMBE-HXSWCURESA-O
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Sphingolipids
Sub Class Lysosphingomyelins 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 Parent Lysosphingomyelins and Lysoglycosphingolipids
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 8.420E-04 g/L ALOGPS
LogP 1.30 ALOGPS
LogP -0.24 ChemAxon
LogS -5.77 ALOGPS
pKa (strongest acidic) 1.83 ChemAxon
pKa (strongest basic) 9.68 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 102.01 A2 ChemAxon
Rotatable Bond Count 21 ChemAxon
Refractivity 141.18 ChemAxon
Polarizability 55.37 ChemAxon
Formal Charge 1 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023932
KNApSAcK ID Not Available
Chemspider ID 4444221 Link_out
KEGG Compound ID C03640 Link_out
BioCyc ID Not Available
BiGG ID 2704995 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06482 Link_out
Metagene Link HMDB06482 Link_out
METLIN ID Not Available
PubChem Compound 5280613 Link_out
PDB ID SPU Link_out
ChEBI ID 52897 Link_out
References
Synthesis Reference Sphingomyelin, 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 Link_out

Enzymes
Name: Sphingomyelin phosphodiesterase
Reactions: Not Available
Gene Name: SMPD1
Uniprot ID: P17405 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 1
Reactions: Not Available
Gene Name: B3GAT1
Uniprot ID: Q9P2W7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 7
Reactions: Not Available
Gene Name: ENPP7
Uniprot ID: Q6UWV6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase 2
Reactions: Not Available
Gene Name: SMPD2
Uniprot ID: O60906 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Proactivator polypeptide
Reactions: Not Available
Gene Name: PSAP
Uniprot ID: P07602 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3
Reactions: Not Available
Gene Name: PLCD3
Uniprot ID: Q8N3E9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase 3
Reactions: Not Available
Gene Name: SMPD3
Uniprot ID: Q9NY59 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase 4
Reactions: Not Available
Gene Name: SMPD4
Uniprot ID: Q9NXE4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Non-lysosomal glucosylceramidase
Reactions: Not Available
Gene Name: GBA2
Uniprot ID: Q9HCG7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin synthase-related protein 1
Reactions: Not Available
Gene Name: SAMD8
Uniprot ID: Q96LT4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA