SM(d18:0/16:0) (CHEM039479)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 17:12:05 UTC
Update Date2016-11-09 01:22:05 UTC
Accession NumberCHEM039479
Identification
Common NameSM(d18:0/16:0)
ClassSmall Molecule
DescriptionSM(d18:0/16:0) (d18:0/16:0) or SM(d18:0/16:0)is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. SM(18:0/16:0) consists of stearic acid attached to the C1 position and palmitic acid attached to the C2 position. In humans, SM(d18:0/16:0) is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SPH has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in SM(d18:0/16:0) and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a SM(d18:0/16:0) pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down SM(d18:0/16:0) into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be SM(d18:0/16:0) present there. SM(d18:0/16:0) can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme Sphingomyelinase, which causes the accumulation of SM(d18:0/16:0) in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by SM(d18:0/16:0) synthase.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
C16 SphingomyelinHMDB
N-(Hexadecanoyl)-sphing-4-enine-1-phosphocholineHMDB
SphingomyelinHMDB
Sphingomyelin (D18:0/16:0)HMDB
N-(Hexadecanoyl)-1-phosphocholine-sphinganineMetBuilder
Sphingomyelin(D18:0/16:0)MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-dihydrosphingosineMetBuilder
N-(Hexadecanoyl)-1-phosphocholine-D-erythro-sphinganineMetBuilder
Chemical FormulaC39H82N2O6P
Average Molecular Mass706.052 g/mol
Monoisotopic Mass705.591 g/mol
CAS Registry NumberNot Available
IUPAC Name{[(2S,3R)-2-hexadecanamido-3-hydroxyoctadecyl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid
Traditional Name[(2S,3R)-2-hexadecanamido-3-hydroxyoctadecyl]oxy(2-(trimethylammonio)ethoxy)phosphinic acid
SMILES[H][C@@](O)(CCCCCCCCCCCCCCC)[C@]([H])(COP(O)(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCCCCCC
InChI IdentifierInChI=1S/C39H81N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h37-38,42H,6-36H2,1-5H3,(H-,40,43,44,45)/p+1/t37-,38+/m0/s1
InChI KeyQHZIGNLCLJPLCU-QPPIDDCLSA-O
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 amide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic salt
  • Amine
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.2e-05 g/LALOGPS
logP4.93ALOGPS
logP8.27ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)0.025ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.09 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity214.1 m³·mol⁻¹ChemAxon
Polarizability89.86 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0010168
FooDB IDFDB027351
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4446704
ChEBI ID17636
PubChem Compound ID5283591
Kegg Compound IDC00550
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available