Showing metabocard for SM(d18:0/22:3(10Z,13Z,16Z)) (BMDB0013468)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:39:20 UTC
Update Date2020-06-04 19:00:53 UTC
BMDB IDBMDB0013468
Secondary Accession Numbers
  • BMDB13468
Metabolite Identification
Common NameSM(d18:0/22:3(10Z,13Z,16Z))
Description(2-{[(2S)-3-hydroxy-2-{[(10Z,13Z,16Z)-1-hydroxydocosa-10,13,16-trien-1-ylidene]amino}octadecyl 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)-3-hydroxy-2-{[(10Z,13Z,16Z)-1-hydroxydocosa-10,13,16-trien-1-ylidene]amino}octadecyl phosphonato]oxy}ethyl)trimethylazanium.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SphingomyelinMetBuilder
N-(10Z,13Z,16Z-Docosenoyl)-1-phosphocholine-sphinganineMetBuilder
Sphingomyelin(D18:0/22:3(10Z,13Z,16Z))MetBuilder
N-(10Z,13Z,16Z-Docosenoyl)-1-phosphocholine-dihydrosphingosineMetBuilder
N-(10Z,13Z,16Z-Docosenoyl)-1-phosphocholine-D-erythro-sphinganineMetBuilder
Chemical FormulaC45H87N2O6P
Average Molecular Weight783.173
Monoisotopic Molecular Weight782.630175527
IUPAC Name(2-{[(2S)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienamido]-3-hydroxyoctadecyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2S)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienamido]-3-hydroxyoctadecyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C45H87N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-29-31-33-35-37-39-45(49)46-43(42-53-54(50,51)52-41-40-47(3,4)5)44(48)38-36-34-32-30-28-26-19-17-15-13-11-9-7-2/h14,16,20-21,23-24,43-44,48H,6-13,15,17-19,22,25-42H2,1-5H3,(H-,46,49,50,51)/b16-14-,21-20-,24-23-/t43-,44?/m0/s1
InChI KeyNPGHIRWPKWLHRU-OTJUQMLZSA-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
StatusDetected and 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
logP5.97ALOGPS
logP8.76ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area107.92 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity243.94 m³·mol⁻¹ChemAxon
Polarizability97.65 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, Positivesplash10-001r-9031167600-0757f45c1ec13df67395View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3191186100-ea881d95f982aa016a8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-8192003100-6e3ca20b936b23ede51aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000002900-21d307853db7bbdcda00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-2024139400-b65320dc32426680c29aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9137020000-4dad3bb5b24f516b347eView in MoNA
Biological Properties
Cellular Locations
  • Axon
  • Cell membrane
  • Endosome
  • Membrane
  • Myelin sheath
Biospecimen Locations
  • Blood
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.003 +/- 0.01 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
 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