Showing metabocard for SM(d18:0/22:3(10Z,13Z,16Z)) (LMDB00629)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:54:07 UTC
Update Date2016-09-23 18:45:40 UTC
LmdbLMDB00629
Secondary Accession NumbersNone
Metabolite Identification
Common NameSM(d18:0/22:3(10Z,13Z,16Z))
DescriptionSphingomyelin (d18:0/22:3(10Z,13Z,16Z)) or SM (d18:0/22:3(10Z,13Z,16Z)) 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
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
C22:3 SphingomyelinHMDB
N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholineHMDB
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 FormulaC45H85N2O6P
Average Molecular Weight781.14
Monoisotopic Molecular Weight780.614524974
IUPAC Name(2-{[(2S,3R,4E)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienamido]-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2S,3R,4E)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienamido]-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](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/C45H85N2O6P/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/h14,16,20-21,23-24,36,38,43-44,48H,6-13,15,17-19,22,25-35,37,39-42H2,1-5H3,(H-,46,49,50,51)/b16-14-,21-20-,24-23-,38-36+/t43-,44+/m0/s1
InChI KeyYTQGMICAWXIKQI-OIMFMVRSSA-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 DescriptorsNot Available
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
logP5.98ALOGPS
logP9.65ChemAxon
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 Count39ChemAxon
Refractivity244.9 m³·mol⁻¹ChemAxon
Polarizability96.72 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001s-6021191400-557ab4f38846192585b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2161191000-e8ddd0e535990eddb776Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-7092002100-416f5929569024596c7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000002900-b481cc5dc0793e7568aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2025149400-92a80422f0b7499c6608Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9137020000-98df2cfb2cd00650eab4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0600000900-439c211144ee1643a11eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-439c211144ee1643a11eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000300-0be8560f723dfe5abeb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000001900-f50cae3af91435376f21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue0-0000007900-e5e7b187daad04a4b8f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0000039300-7d0b50ab5745ea11438fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-d0a8ce956fa8a5c76189Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000001900-8ba6482033b3c0fcd8fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010301000-5aad112432764041bbc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000001190-447388101896927c60d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ur0-0000009290-6006512be3a0badac22eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0000039110-df7ab7feb7903afd44d9Spectrum
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
Ruminal FluidDetected and Quantified0.001 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified0.001 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified0.003 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified0.003 uMNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
DrugBank IDNot Available
HMDB IDHMDB0013468
FooDB IDFDB029468
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID90002
PubChem Compound ID53481789
Kegg Compound IDC00550
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available