| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2010-03-24 10:57:27 -0600 |
| Update Date |
2013-02-08 17:30:19 -0700 |
| HMDB ID |
HMDB13469 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
SM(d18:0/24:1(15Z)(OH)) |
| Description |
Sphingomyelin (d18:0/24:1(15Z)(OH))or SM(d18:0/24:1(15Z)(OH)) 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 humans, 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- C24:1-OH Sphingomyelin
- N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholine
|
| Chemical Formula |
C47H93N2O7P |
| Average Molecular Weight |
829.2243 |
| Monoisotopic Molecular Weight |
828.672039852 |
| IUPAC Name |
(2-{[(2S,3R,4E)-3-hydroxy-2-[(15Z)-3-hydroxytetracos-15-enamido]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium |
| Traditional IUPAC Name |
(2-{[(2S,3R,4E)-3-hydroxy-2-[(15Z)-3-hydroxytetracos-15-enamido]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium |
| CAS Registry Number |
Not Available |
| SMILES |
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CC(O)CCCCCCCCCCC\C=C/CCCCCCCC |
| InChI Identifier |
InChI=1S/C47H93N2O7P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-28-30-32-34-36-38-44(50)42-47(52)48-45(43-56-57(53,54)55-41-40-49(3,4)5)46(51)39-37-35-33-31-29-26-19-17-15-13-11-9-7-2/h20-21,37,39,44-46,50-51H,6-19,22-36,38,40-43H2,1-5H3,(H-,48,52,53,54)/b21-20-,39-37+/t44?,45-,46+/m0/s1 |
| InChI Key |
IOOMOQUTKQGEFH-BSZNTFKYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Sphingolipids |
| Sub Class |
Sphingomyelins |
| Other Descriptors |
- Aliphatic Acyclic Compounds
|
| Substituents |
- 1,3 Aminoalcohol
- Acyclic Alkene
- Allyl Alcohol
- Carboxamide Group
- Ceramide
- Choline
- N Acyl Amine
- Organic Hypophosphite
- Organic Phosphite
- Phosphocholine
- Phosphoethanolamine
- Phosphoric Acid Ester
- Quaternary Ammonium Salt
- Secondary Alcohol
- Secondary Carboxylic Acid Amide
|
| Direct Parent |
Sphingomyelins |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Energy source
- Fuel and energy storage
- Fuel or energy source
- Membrane component
- Membrane integrity/stability
|
| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
|
| Cellular locations |
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
- Cerebrospinal Fluid (CSF)
- Urine
|
| Tissue Location |
Not Available
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.017 +/- 0.004 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.001 (0.00034-0.0025) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
by DFI-MS/MS (Biocrates kit)
|
|
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB029469 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
Not Available |
| KEGG Compound ID |
C00550  |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Sphingomyelin |
| NuGOwiki Link |
HMDB13469 |
| Metagene Link |
HMDB13469 |
| METLIN ID |
Not Available |
| PubChem Compound |
53481791 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available |
