SM(d18:0/16:1(9Z)(OH)) (CHEM041259)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:17:55 UTC
Update Date2016-11-09 01:22:26 UTC
Accession NumberCHEM041259
Identification
Common NameSM(d18:0/16:1(9Z)(OH))
ClassSmall Molecule
DescriptionAn N-hydroxyhexadecenoylsphingosine-1-phosphocholine in which the N-acyl group is specified as (9Z)-3-hydroxyhexadec-9-enoyl.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
C16:1-OH SphingomyelinChEBI
Hydroxysphingomyeline C16:1ChEBI
N-[(9Z)-3-Hydroxyhexadec-9-enoyl]sphing-4-enine-1-phosphocholineChEBI
SM(D18:1/16:1(9Z)(OH))ChEBI
N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholineHMDB
SphingomyelinMetBuilder
N-(3-Hydroxy-9Z-hexadecenoyl)-1-phosphocholine-sphinganineMetBuilder
Sphingomyelin(D18:0/16:1(9Z)(OH))MetBuilder
N-(3-Hydroxy-9Z-hexadecenoyl)-1-phosphocholine-dihydrosphingosineMetBuilder
N-(3-Hydroxy-9Z-hexadecenoyl)-1-phosphocholine-D-erythro-sphinganineMetBuilder
Chemical FormulaC39H77N2O7P
Average Molecular Mass717.012 g/mol
Monoisotopic Mass716.547 g/mol
CAS Registry NumberNot Available
IUPAC Name(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxyhexadec-9-enamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxyhexadec-9-enamido]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)CCCCC\C=C/CCCCCC
InChI IdentifierInChI=1S/C39H77N2O7P/c1-6-8-10-12-14-16-18-19-21-23-25-27-29-31-38(43)37(35-48-49(45,46)47-33-32-41(3,4)5)40-39(44)34-36(42)30-28-26-24-22-20-17-15-13-11-9-7-2/h17,20,29,31,36-38,42-43H,6-16,18-19,21-28,30,32-35H2,1-5H3,(H-,40,44,45,46)/b20-17-,31-29+/t36?,37-,38+/m0/s1
InChI KeyLPHMSPONPQCKTL-FKUNDBCPSA-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 Solubility4.8e-05 g/LALOGPS
logP4.38ALOGPS
logP5.38ChemAxon
logS-7.2ALOGPS
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 Count35ChemAxon
Refractivity216.57 m³·mol⁻¹ChemAxon
Polarizability87.13 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 GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 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 GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00m1-5020195100-75c4428f308b70e492a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-2140191000-1a1ed63feed3f152dcdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-8190032000-c1f385095a959e7e14beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0010004900-03516550d63a4b14a21dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02u0-1172149200-27f568a6bfc192cf91f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-9183120000-1d21406c331bfb554143Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000011900-4aa51f66c591f10a45d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a50-0000092900-3dc7f7c1babd46a42d93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0000091100-d0b9a75fac9ff500e6c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000900-282d41e16428007043d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0020003900-41188580822b70887c3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9282000000-d0383bad10de3658c4d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000011900-913b25a99091d7742381Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00do-0000092900-807f48801e76940db556Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0000091100-11de640103dd3b340f84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0600000900-a4544d9a891eec8a2b0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0600000900-a4544d9a891eec8a2b0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900001100-59b07f8576eaafa65901Spectrum
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 IDHMDB0013463
FooDB IDFDB029463
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 ID90007
PubChem Compound ID53481779
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. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78.
4. Hannun YA: The sphingomyelin cycle and the second messenger function of ceramide. J Biol Chem. 1994 Feb 4;269(5):3125-8.
5. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50.
6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
7. 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.
8. 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.
9. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
10. Phospholipids Handbook
11. The lipid handbook with CD-ROM