SM(d18:0/26:1(17Z)) (CHEM041257)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:17:52 UTC
Update Date2016-11-09 01:22:26 UTC
Accession NumberCHEM041257
Identification
Common NameSM(d18:0/26:1(17Z))
ClassSmall Molecule
DescriptionA N-hexacosenoylsphingosine-1-phosphocholine consisting of sphingosine as the sphingoid base acylated at the N atom by a (17Z)-hexacosenoyl group.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
C26:1 SphingomyelinChEBI
N-(17Z-Hexacosenoyl)-sphing-4-enine-1-phosphocholineChEBI
N-(Tricosanoyl)-sphing-4-enine-1-phosphocholineHMDB
SphingomyelinHMDB
N-(17Z-Hexacosenoyl)-1-phosphocholine-sphing-4-enineMetBuilder
Sphingomyelin(D18:1/26:1(17Z))MetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-sphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-D-erythro-sphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-4-sphingenineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-D-sphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-sphingenineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-erythro-4-sphingenineMetBuilder
SM(D18:1/26:1(17Z))ChEBI
N-(17Z-Hexacosenoyl)-1-phosphocholine-sphinganineMetBuilder
Sphingomyelin(D18:0/26:1(17Z))MetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-dihydrosphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-D-erythro-sphinganineMetBuilder
Chemical FormulaC49H97N2O6P
Average Molecular Mass841.278 g/mol
Monoisotopic Mass840.708 g/mol
CAS Registry NumberNot Available
IUPAC Name(2-{[(2S,3R,4E)-2-[(17Z)-hexacos-17-enamido]-3-hydroxyoctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2S,3R,4E)-2-[(17Z)-hexacos-17-enamido]-3-hydroxyoctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium
SMILESCCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCCCCCC\C=C/CCCCCCCC
InChI IdentifierInChI=1S/C49H97N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-28-29-31-33-35-37-39-41-43-49(53)50-47(46-57-58(54,55)56-45-44-51(3,4)5)48(52)42-40-38-36-34-32-30-19-17-15-13-11-9-7-2/h20-21,40,42,47-48,52H,6-19,22-39,41,43-46H2,1-5H3,(H-,50,53,54,55)/b21-20-,42-40+/t47-,48+/m0/s1
InChI KeyYXEXWUZHFGYOHJ-UOJCCMJYSA-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
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 Solubility2.6e-05 g/LALOGPS
logP6.53ALOGPS
logP11.06ChemAxon
logS-7.5ALOGPS
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 Count45ChemAxon
Refractivity261.07 m³·mol⁻¹ChemAxon
Polarizability108.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053l-6011109040-78d43e222f56260422feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0536-2142109100-86de838a540453f018fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001s-9166002300-ec56b7022d6302efcb2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000490-cb91e2cdfa0fc1ef0e53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2015004920-8dd85b3408ce46984d72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9128002000-1f1df5bc5b2e61edb1daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000001190-852973a8181afd58aa19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dk-0000009290-2a89ec676a087342ac72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000009110-41d912ffebeab2f9e19cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000x-0600000090-f3afb84c3623381e151fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0600000090-f3afb84c3623381e151fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000030-ea80282a636c1f91d6e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-dbddecc32b1e8eef807dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000000390-a19ee8177a5c774ca039Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9001030100-33cf30aa4edf3e21f80cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000001090-b6e3615b7d0d42bfc294Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03f0-0000007090-7266def15f5db339d557Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0000009020-fbc8eda2d3b38d2ae7b9Spectrum
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 IDHMDB0013461
FooDB IDFDB029461
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24846876
ChEBI ID84476
PubChem Compound ID44260128
Kegg Compound IDC00550
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78.
6. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50.
7. Hannun YA: The sphingomyelin cycle and the second messenger function of ceramide. J Biol Chem. 1994 Feb 4;269(5):3125-8.
8. Phospholipids Handbook
9. The lipid handbook with CD-ROM