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Record Information
Version1.0
Creation Date2016-07-13 19:52:46 UTC
Update Date2016-09-23 18:45:37 UTC
LmdbLMDB00570
Secondary Accession NumbersNone
Metabolite Identification
Common NameSM(d18:1/24:1(15Z))
DescriptionSphingomyelin (d18:1/24:1(15Z)) or SM(d18:1/24:1(15Z)) 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. In animals, sphingomyelin 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 sphingomyelin 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 sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down sphingomyelin into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin 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 Sphingomyelin 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 sphingomyelin synthase.
Structure
Thumb
Synonyms
ValueSource
C24:1 SphingomyelinChEBI
N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholineChEBI
N-(15Z-Tetracosenoyl)sphing-4-enine-1-phosphocholineChEBI
SphingomyelinHMDB
N-(15Z-Tetracosenoyl)-1-phosphocholine-sphing-4-enineHMDB
Sphingomyelin(D18:1/24:1(15Z))HMDB
N-(15Z-Tetracosenoyl)-1-phosphocholine-sphingosineHMDB
N-(15Z-Tetracosenoyl)-1-phosphocholine-D-erythro-sphingosineHMDB
N-(15Z-Tetracosenoyl)-1-phosphocholine-4-sphingenineHMDB
N-(15Z-Tetracosenoyl)-1-phosphocholine-D-sphingosineHMDB
N-(15Z-Tetracosenoyl)-1-phosphocholine-sphingenineHMDB
N-(15Z-Tetracosenoyl)-1-phosphocholine-erythro-4-sphingenineHMDB
SM D18:1/24:1(15Z)HMDB
Sphingomyelin (D18:1,C24:1(15Z))HMDB
Sphingomyelin (D18:1/24:1(15Z))HMDB
SM(D18:1/24:1(15Z))ChEBI
Chemical FormulaC47H93N2O6P
Average Molecular Weight813.2249
Monoisotopic Molecular Weight812.67712523
IUPAC Name(2-{[(2S,3R,4E)-3-hydroxy-2-[(15Z)-tetracos-15-enamido]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium
Traditional NameC24:1 sphingomyelin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C47H93N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-29-31-33-35-37-39-41-47(51)48-45(44-55-56(52,53)54-43-42-49(3,4)5)46(50)40-38-36-34-32-30-28-19-17-15-13-11-9-7-2/h20-21,38,40,45-46,50H,6-19,22-37,39,41-44H2,1-5H3,(H-,48,51,52,53)/b21-20-,40-38+/t45-,46+/m0/s1
InChI KeyWKZHECFHXLTOLJ-QYKFWSDSSA-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 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 zwitterion
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Amine
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.3ALOGPS
logP11.26ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)0.012ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area107.92 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity251.87 m³·mol⁻¹ChemAxon
Polarizability103.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qj-6011109310-e55f9a9b7fe1fa074f2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-2142109100-042e69121044cc723425Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-008i-9166003200-491572fa5edbe8ee5512Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000490-a68aba8c44804dba30ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08i0-2015104920-3eb8b1ec9c81fa6a1560Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-9128002000-95b79a4f5adbce3d07b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0600000090-139550ecb3809eb4819fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000090-139550ecb3809eb4819fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000110-5abb18835ee1db626837Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000001190-723e05c52172cf4b8083Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue0-0000009290-b3f9f3329970da774224Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0000009110-3e0915ce1af8e9733cfcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-fd44e397a6bdccec75d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000000390-a4ffc25b99b9424b0a4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9001300100-de705bb79d2d2a50b172Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000001190-469667d89771f34fe9cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0150-0000009290-7720669a8b116abc32beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0000009110-45ca65e6e07937c41807Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected and Quantified17.51 +/- 1.40-21.14+/-1.40 uMNot AvailablePorcine details
PlasmaDetected and Quantified18.8 +/- 1.46-16.74+/-1.46 uMNot AvailablePorcine details
Ruminal FluidDetected and Quantified0.01 +/- 0.005 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified0.02 +/- 0.07 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified0.03 +/- 0.06 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified0.04 +/- 0.01 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified0.04 +/- 0.01 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified0.006 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified0.009 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified0.024 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified0.034 uMNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
DrugBank IDNot Available
HMDB IDHMDB0012107
FooDB IDFDB028771
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24846874
ChEBI ID74535
PubChem Compound ID44260126
Kegg Compound IDC00550
YMDB IDYMDB01550
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available