Showing metabocard for SM(d18:1/20:0) (BMDB0012102)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:32:19 UTC
Update Date2020-05-11 20:42:42 UTC
BMDB IDBMDB0012102
Secondary Accession Numbers
  • BMDB12102
Metabolite Identification
Common NameSM(d18:1/20:0)
Description(2-{[(2S,4E)-3-hydroxy-2-[(1-hydroxyicosylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group. Based on a literature review very few articles have been published on (2-{[(2S,4E)-3-hydroxy-2-[(1-hydroxyicosylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SphingomyelinMetBuilder
N-(Eicosanoyl)-1-phosphocholine-sphing-4-enineMetBuilder
Sphingomyelin(D18:1/20:0)MetBuilder
N-(Eicosanoyl)-1-phosphocholine-sphingosineMetBuilder
N-(Eicosanoyl)-1-phosphocholine-D-erythro-sphingosineMetBuilder
N-(Eicosanoyl)-1-phosphocholine-4-sphingenineMetBuilder
N-(Eicosanoyl)-1-phosphocholine-D-sphingosineMetBuilder
N-(Eicosanoyl)-1-phosphocholine-sphingenineMetBuilder
N-(Eicosanoyl)-1-phosphocholine-erythro-4-sphingenineMetBuilder
Chemical FormulaC43H87N2O6P
Average Molecular Weight759.151
Monoisotopic Molecular Weight758.630175527
IUPAC Name(2-{[(2S,4E)-3-hydroxy-2-icosanamidooctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2S,4E)-3-hydroxy-2-icosanamidooctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)C(O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C43H87N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-43(47)44-41(40-51-52(48,49)50-39-38-45(3,4)5)42(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h34,36,41-42,46H,6-33,35,37-40H2,1-5H3,(H-,44,47,48,49)/b36-34+/t41-,42?/m0/s1
InChI KeyAADLTHQNYQJHQV-VFZJAREDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassPhosphosphingolipids
Direct ParentPhosphosphingolipids
Alternative Parents
Substituents
  • Sphingoid-1-phosphate or derivatives
  • Phosphocholine
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • N-acyl-amine
  • Fatty amide
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organic zwitterion
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Axon
  • Cell membrane
  • Endosome
  • Membrane
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.8ALOGPS
logP8.75ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area107.92 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity232.35 m³·mol⁻¹ChemAxon
Polarizability96.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7r-6030190400-37b4a69afd8b212a3895View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0561-2070191000-2c0e4d3d043470f12ce2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00m0-6091012000-1fae6b22107c70f18819View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000003900-b5dcf091c61258b4d907View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-11b9-2033149200-d0ecbd86b7cb9e2ccaf1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-9156020000-02560c20f114d018616fView in MoNA
Biological Properties
Cellular Locations
  • Axon
  • Cell membrane
  • Endosome
  • Membrane
  • Myelin sheath
Biospecimen Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available