Showing metabocard for LysoSM(d18:1) (BMDB0006482)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:22:23 UTC
Update Date2020-04-22 15:17:33 UTC
BMDB IDBMDB0006482
Secondary Accession Numbers
  • BMDB06482
Metabolite Identification
Common NameLysoSM(d18:1)
DescriptionLysoSM(d18:1), also known as lysosphingomyelin, belongs to the class of organic compounds known as sphingosylphosphorylcholines. These are sphingolipids containing a sphingosine attached to the phosphate group of a phosphocholine. Based on a literature review very few articles have been published on LysoSM(d18:1).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Sphing-4-enine-1-phosphocholineChEBI
Sphingosyl-phosphocholineChEBI
SphingosylphosphocholineChEBI
LysosphingomyelinMeSH
Sphingosine phosphorylcholineMeSH
C18-Sphingosine phosphocholineHMDB
D-erythro-SphingosylphosphorylcholineHMDB
SM(D18:1/0:0)HMDB
Sphingenyl-1-phosphorylcholineHMDB
Sphingomyelin(D18:1/0:0)HMDB
SphingosylphosphorylcholineMeSH, HMDB
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 Namelysosphingomyelin
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
Description belongs to the class of organic compounds known as sphingosylphosphorylcholines. These are sphingolipids containing a sphingosine attached to the phosphate group of a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassPhosphosphingolipids
Direct ParentSphingosylphosphorylcholines
Alternative Parents
Substituents
  • Sphingosylphosphorylcholine
  • Phosphocholine
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • Alcohol
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Endosome
  • 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
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 Area102.01 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity141.18 m³·mol⁻¹ChemAxon
Polarizability55.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen Locations
  • Blood
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Hepatic lipidosis		 details
HMDB IDHMDB0006482
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023932
KNApSAcK IDNot Available
Chemspider ID4444221
KEGG Compound IDC03640
BioCyc IDNot Available
BiGG ID2704995
Wikipedia LinkNot Available
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 ReferencesNot Available