SM(d18:0/22:2(13Z,16Z)(OH)) (CHEM041263)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:18:00 UTC
Update Date2016-11-09 01:22:26 UTC
Accession NumberCHEM041263
Identification
Common NameSM(d18:0/22:2(13Z,16Z)(OH))
ClassSmall Molecule
DescriptionAn N-hydroxydocosadienoylsphingosine-1-phosphocholine in which the N-acyl group is specified as (13Z,16Z)-3-hydroxydocosa-13,16-enoyl.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
C22:2-OH SphingomyelinChEBI
Hydroxysphingomyeline C22:2ChEBI
N-[(13Z,16Z)-3-Hydroxydocosa-13,16-enoyl]sphing-4-enine-1-phosphocholineChEBI
SM(D18:1/22:2(13Z,16Z)(OH))ChEBI
N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholineHMDB
SphingomyelinMetBuilder
N-(3-Hydroxy-13Z,16Z-docosenoyl)-1-phosphocholine-sphinganineMetBuilder
Sphingomyelin(D18:0/22:2(13Z,16Z)(OH))MetBuilder
N-(3-Hydroxy-13Z,16Z-docosenoyl)-1-phosphocholine-dihydrosphingosineMetBuilder
N-(3-Hydroxy-13Z,16Z-docosenoyl)-1-phosphocholine-D-erythro-sphinganineMetBuilder
Chemical FormulaC45H87N2O7P
Average Molecular Mass799.155 g/mol
Monoisotopic Mass798.625 g/mol
CAS Registry NumberNot Available
IUPAC Name(2-{[(2S,3R,4E)-3-hydroxy-2-[(13Z,16Z)-3-hydroxydocosa-13,16-dienamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2S,3R,4E)-3-hydroxy-2-[(13Z,16Z)-3-hydroxydocosa-13,16-dienamido]octadec-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)CC(O)CCCCCCCCC\C=C/C\C=C/CCCCC
InChI IdentifierInChI=1S/C45H87N2O7P/c1-6-8-10-12-14-16-18-20-21-22-23-25-26-28-30-32-34-36-42(48)40-45(50)46-43(41-54-55(51,52)53-39-38-47(3,4)5)44(49)37-35-33-31-29-27-24-19-17-15-13-11-9-7-2/h14,16,20-21,35,37,42-44,48-49H,6-13,15,17-19,22-34,36,38-41H2,1-5H3,(H-,46,50,51,52)/b16-14-,21-20-,37-35+/t42?,43-,44+/m0/s1
InChI KeyDRKCMBAZIYFIGX-ZWLRGCNFSA-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
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 Solubility3.7e-05 g/LALOGPS
logP5.48ALOGPS
logP7.69ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.15 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity245.3 m³·mol⁻¹ChemAxon
Polarizability98.78 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
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 GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0012-7011156900-59f57d1195e03f2c36a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-3262169200-e160ef1cde477bc1e9f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-9183012100-3720247adae3a413f2e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000001900-559fc5cc139f5f32636fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01p7-2046329800-16481575b3d31e9075d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-8129003000-57feb73b7ccaa8c7653aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000900-660cae17b4d35c24b5e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0012000900-83e7b7d1498d9989153fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002o-9053100000-0361dcc7ca7110485dfeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0600000900-30eed8331af5bacc2bebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0600000900-30eed8331af5bacc2bebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000300-b40420bbdef3c1464c6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000001190-dc352a899cda0a07b1a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ai0-0000009290-3b303ea7b058cdc54119Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0000019110-55eff114f0faed1ce593Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000001190-5779ca3e94feeaed7287Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e0-0000009290-9891327c4e39239d6046Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0000019110-f56ce78bf55ca621a041Spectrum
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 IDHMDB0013467
FooDB IDFDB029467
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSphingomyelin
Chemspider IDNot Available
ChEBI ID90003
PubChem Compound ID53481787
Kegg Compound IDC00550
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22546835
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24023812
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. 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.
5. 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.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78.
8. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50.
9. Hannun YA: The sphingomyelin cycle and the second messenger function of ceramide. J Biol Chem. 1994 Feb 4;269(5):3125-8.
10. Phospholipids Handbook
11. The lipid handbook with CD-ROM