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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-16 05:02:28 UTC
Update Date2022-11-30 20:07:14 UTC
HMDB IDHMDB0290593
Secondary Accession NumbersNone
Metabolite Identification
Common NameSM(d18:2(4E,14Z)/20:4(8Z,11Z,14Z,17Z)-2OH(5S,6R))
DescriptionSM(d18:2(4E,14Z)/20:4(8Z,11Z,14Z,17Z)-2OH(5S,6R)) is a type of oxidized sphingolipid found in animal cell membranes. It usually consists of phosphorylcholine and ceramide. SM(d18:2(4E,14Z)/20:4(8Z,11Z,14Z,17Z)-2OH(5S,6R)) consists of a sphingosine backbone and a 5,6-Dihydroxyeicosatetraenoyl chain. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SM 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 localize 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
SynonymsNot Available
Chemical FormulaC43H77N2O8P
Average Molecular Weight781.069
Monoisotopic Molecular Weight780.541754445
IUPAC Name(2-{[(2S,3R,4E,14Z)-2-[(5R,6R,8Z,11Z,14Z,17Z)-5,6-dihydroxyicosa-8,11,14,17-tetraenamido]-3-hydroxyoctadeca-4,14-dien-1-yl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2S,3R,4E,14Z)-2-[(5R,6R,8Z,11Z,14Z,17Z)-5,6-dihydroxyicosa-8,11,14,17-tetraenamido]-3-hydroxyoctadeca-4,14-dien-1-yl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](COP([O-])(=O)OCC[N+](C)(C)C)(NC(=O)CCC[C@@H](O)[C@H](O)C\C=C/C\C=C/C\C=C/C\C=C/CC)[C@H](O)\C=C\CCCCCCCC\C=C/CCC
InChI Identifier
InChI=1S/C43H77N2O8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-32-40(46)39(38-53-54(50,51)52-37-36-45(3,4)5)44-43(49)35-31-34-42(48)41(47)33-30-28-26-24-21-19-17-15-13-11-9-7-2/h9-12,15,17,21,24,28-30,32,39-42,46-48H,6-8,13-14,16,18-20,22-23,25-27,31,33-38H2,1-5H3,(H-,44,49,50,51)/b11-9-,12-10-,17-15-,24-21-,30-28-,32-29+/t39-,40+,41+,42+/m0/s1
InChI KeyCPNUZKRDKUAXFY-ASRKKTSPSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP4.19ALOGPS
logP4.48ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area148.38 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity240.96 m³·mol⁻¹ChemAxon
Polarizability90.67 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+288.73132859911
AllCCS[M+H-H2O]+288.54432859911
AllCCS[M+Na]+288.9132859911
AllCCS[M+NH4]+288.87432859911
AllCCS[M-H]-275.00532859911
AllCCS[M+Na-2H]-280.26732859911
AllCCS[M+HCOO]-286.04932859911
DeepCCS[M+H]+271.05430932474
DeepCCS[M-H]-268.65930932474
DeepCCS[M-2H]-302.15830932474
DeepCCS[M+Na]+276.96730932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - SM(d18:2(4E,14Z)/20:4(8Z,11Z,14Z,17Z)-2OH(5S,6R)) 10V, Positive-QTOFsplash10-001i-0600000900-8afcb46a9713ad79d6ac2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - SM(d18:2(4E,14Z)/20:4(8Z,11Z,14Z,17Z)-2OH(5S,6R)) 20V, Positive-QTOFsplash10-001i-0600000900-8afcb46a9713ad79d6ac2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - SM(d18:2(4E,14Z)/20:4(8Z,11Z,14Z,17Z)-2OH(5S,6R)) 40V, Positive-QTOFsplash10-001i-0900000300-2bb5c023d444e640d11f2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - SM(d18:2(4E,14Z)/20:4(8Z,11Z,14Z,17Z)-2OH(5S,6R)) 10V, Positive-QTOFsplash10-000i-0000001900-93c538f2e9ad78602bc92021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - SM(d18:2(4E,14Z)/20:4(8Z,11Z,14Z,17Z)-2OH(5S,6R)) 20V, Positive-QTOFsplash10-0ue0-0000007900-626a0a706eb00e55943f2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - SM(d18:2(4E,14Z)/20:4(8Z,11Z,14Z,17Z)-2OH(5S,6R)) 40V, Positive-QTOFsplash10-0udi-0000039300-a525febc429d49d6006e2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - SM(d18:2(4E,14Z)/20:4(8Z,11Z,14Z,17Z)-2OH(5S,6R)) 10V, Positive-QTOFsplash10-0udi-0000001190-63d5dc0f2d70908e51482021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - SM(d18:2(4E,14Z)/20:4(8Z,11Z,14Z,17Z)-2OH(5S,6R)) 20V, Positive-QTOFsplash10-0ur0-0000009290-3110a286a46703cefbc22021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - SM(d18:2(4E,14Z)/20:4(8Z,11Z,14Z,17Z)-2OH(5S,6R)) 40V, Positive-QTOFsplash10-00di-0000039110-60d8e9a1e9304c5ce96c2021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available