| Version |
1.0 |
| Creation Date |
2010-03-24 17:57:20 |
| Update Date |
2010-05-12 12:02:40 |
| Accession Number |
BMDB13462 |
| Common Name |
SM(d18:0/14:1(9Z)(OH)) |
| Description |
Sphingomyelin (d18:0/14:1(9Z)(OH)) or SM(d18:0/14:1(9Z)(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. |
| Synonyms |
- C14:1-OH Sphingomyelin
- N-(15Z-tetracosenoyl)-sphing-4-enine-1-phosphocholine
|
| Chemical IUPAC Name |
Not Available |
| Chemical Formula |
C37H73N2O7P |
| Chemical Structure |
 |
| Chemical Taxonomy |
| Kingdom |
|
| Super Class |
|
| Class |
|
| Sub Class |
|
| Family |
|
| Species |
- cation; anion; secondary alcohol; quaternary ammonium salt; secondary carboxylic acid amide; phosphoric acid ester; alkene
|
| Biofunction |
- Membrane component; Energy source; Cell signaling
|
| Application |
| — |
| Source |
|
|
| Average Molecular Weight |
688.958 |
| Monoisotopic Molecular Weight |
688.515564 |
| Isomeric SMILES |
CCCCCCCCCCCCCC=C[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CC(O)CCCCCC=C/CCCC |
| Canonical SMILES |
CCCCCCCCCCCCCC=CC(O)C(COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CC(O)CCCCCC=CCCCC |
| KEGG Compound ID |
C00550  |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Sphingomyelin |
| METLIN ID |
Not Available |
| PubChem Compound |
Not Available |
| PubChem Substance |
Not Available |
| ChEBI ID |
Not Available |
| CAS Registry Number |
Not Available |
| InChI Identifier |
InChI=1/C37H73N2O7P/c1-6-8-10-12-14-16-17-18-19-21-23-25-27-29-36(41)35(33-46-47(43,44)45-31-30-39(3,4)5)38-37(42)32-34(40)28-26-24-22-20-15-13-11-9-7-2/h13,15,27,29,34-36,40-41H,6-12,14,16-26,28,30-33H2,1-5H3,(H-,38,42,43,44)/b15-13-,29-27+/t34?,35-,36+/m0/s1 |
| Synthesis Reference |
Not Available |
| Melting Point (Experimental) |
Not Available |
| Experimental Water Solubility |
Not Available
Source: PhysProp
|
| Predicted Water Solubility |
5.96e-05 mg/mL [Predicted by ALOGPS]
Calculated using ALOGPS
|
| Physiological Charge |
0 |
| State |
Solid |
| Experimental LogP/Hydrophobicity |
Not Available
Source: PhysProp
|
| Predicted LogP/Hydrophobicity |
3.91 [Predicted by ALOGPS]
Calculated using ALOGPS
|
| Material Safety Data Sheet (MSDS) |
Not Available |
| MOL File |
Show |
| SDF File |
Show |
| PDB File |
Show |
| 2D Structure |
|
| 3D Structure |
|
| Experimental PDB ID |
Not Available |
| Experimental 1H NMR Spectrum |
Not Available |
| Experimental 13C NMR Spectrum |
Not Available |
| Experimental 13C HSQC Spectrum |
Not Available |
| Predicted 1H NMR Spectrum |
Not Available
Not Available
|
| Predicted 13C NMR Spectrum |
Not Available
Not Available
|
| Mass Spectrum |
Not Available |
| Simplified TOCSY Spectrum |
Not Available |
| BMRB Spectrum |
Not Available |
| Cellular Location |
|
| Biofluid Location |
|
| Tissue Location |
Not Available |
| Concentrations (Normal) |
| Biofluid |
Breast_Milk |
| Value |
1.71 +/- 0.047 uM |
| Age |
N/A |
| Sex |
N/A |
| Condition |
Normal |
| Comments |
Quantified by DFI-MS in 1% milk |
| References |
|
| Biofluid |
Breast_Milk |
| Value |
1.583 +/- 0.042 uM |
| Age |
N/A |
| Sex |
N/A |
| Condition |
Normal |
| Comments |
Quantified by DFI-MS in skim milk |
| References |
|
| Biofluid |
Breast_Milk |
| Value |
1.144 +/- 0.03 uM |
| Age |
N/A |
| Sex |
N/A |
| Condition |
Normal |
| Comments |
Quantified by DFI-MS in 2% milk |
| References |
|
| Biofluid |
Breast_Milk |
| Value |
1.86 +/- 0.03 uM |
| Age |
N/A |
| Sex |
N/A |
| Condition |
Normal |
| Comments |
Quantified by DFI-MS in 3.25% milk |
| References |
|
| Biofluid |
Rumen |
| Value |
0.001 +/- 0.002 uM |
| Age |
N/A |
| Sex |
N/A |
| Condition |
Normal |
| Comments |
Not Available |
| References |
- The rumen metabolome (in preparation)
|
|
| Concentrations (Abnormal) |
Not Available |
| Pathway Names |
Not Available |
| HMDB Pathways |
Not Available |
| KEGG Pathways |
Not Available |
| SimCell Pathways |
Not Available |
| General References |
- Wikipedia
|
