| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-07-13 19:51:46 UTC |
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| Update Date | 2021-04-30 20:57:40 UTC |
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| Lmdb | LMDB00524 |
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| Secondary Accession Numbers | None |
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| Metabolite Identification |
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| Common Name | SM(d18:1/16:0) |
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| Description | Sphingomyelin (d18:1/16:0) or SM(d18:1/16:0) is a sphingomyelin. Sphingomyelin (SM or SPH) 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. SM(18:1/16:0) consists of oleic acid attached to the C1 position and palmitic acid attached to the C2 position. In animals, 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. |
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| Structure | |
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| Synonyms | | Value | Source |
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| C16 Sphingomyelin | HMDB | | N-(Hexadecanoyl)-sphing-4-enine-1-phosphocholine | HMDB | | Sphingomyelin | HMDB | | Sphingomyelin (D18:1/16:0) | HMDB | | N-(Hexadecanoyl)-1-phosphocholine-sphing-4-enine | MetBuilder | | Sphingomyelin(D18:1/16:0) | MetBuilder | | N-(Hexadecanoyl)-1-phosphocholine-sphingosine | MetBuilder | | N-(Hexadecanoyl)-1-phosphocholine-D-erythro-sphingosine | MetBuilder | | N-(Hexadecanoyl)-1-phosphocholine-4-sphingenine | MetBuilder | | N-(Hexadecanoyl)-1-phosphocholine-D-sphingosine | MetBuilder | | N-(Hexadecanoyl)-1-phosphocholine-sphingenine | MetBuilder | | N-(Hexadecanoyl)-1-phosphocholine-erythro-4-sphingenine | MetBuilder |
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| Chemical Formula | C39H80N2O6P |
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| Average Molecular Weight | 704.0361 |
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| Monoisotopic Molecular Weight | 703.575399814 |
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| IUPAC Name | {[(2S,3R,4E)-2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid |
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| Traditional Name | [(2S,3R,4E)-2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl]oxy(2-(trimethylammonio)ethoxy)phosphinic acid |
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| CAS Registry Number | Not Available |
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| SMILES | CCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(O)(=O)OCC[N+](C)(C)C)[C@]([H])(O)\C=C\CCCCCCCCCCCCC |
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| InChI Identifier | InChI=1S/C39H79N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h30,32,37-38,42H,6-29,31,33-36H2,1-5H3,(H-,40,43,44,45)/p+1/b32-30+/t37-,38+/m0/s1 |
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| InChI Key | RWKUXQNLWDTSLO-GWQJGLRPSA-O |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Sphingolipids |
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| Sub Class | Phosphosphingolipids |
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| Direct Parent | Phosphosphingolipids |
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| Alternative Parents | |
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| 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 salt
- Amine
- Alcohol
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic cation
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | Not Available |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | Not Available |
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| Plasma | Detected but not Quantified | Not Applicable | Not Available | Bovine | | details | | Plasma | Detected but not Quantified | Not Applicable | Not Available | Bovine | | details | | Plasma | Detected but not Quantified | Not Applicable | Not Available | Ovine | | details | | Ruminal Fluid | Detected and Quantified | 0.002 +/- 0.006 uM | Not Available | Bovine | | details | | Ruminal Fluid | Detected and Quantified | 0.003 +/- 0.01 uM | Not Available | Bovine | | details | | Ruminal Fluid | Detected and Quantified | 0.01 +/- 0.01 uM | Not Available | Bovine | | details | | Ruminal Fluid | Detected and Quantified | 0.04 +/- 0.01 uM | Not Available | Bovine | | details | | Ruminal Fluid | Detected and Quantified | 0.04 +/- 0.01 uM | Not Available | Bovine | | details | | Ruminal Fluid | Detected and Quantified | 0.002 uM | Not Available | Bovine | | details | | Ruminal Fluid | Detected and Quantified | 0.003 uM | Not Available | Bovine | | details | | Ruminal Fluid | Detected and Quantified | 0.006 uM | Not Available | Bovine | | details | | Ruminal Fluid | Detected and Quantified | 0.011 uM | Not Available | Bovine | | details | | Serum | Detected and Quantified | 44.554 +/- 12.0565 uM | Normal | Ovine | | details | | Serum | Detected but not Quantified | Not Applicable | Not Available | Caprine | | details | | Serum | Detected and Quantified | 52.2967 +/- 30.1198 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 46.1561 +/- 19.9309 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 44.8085 +/- 11.3749 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 46.5749 +/- 14.3229 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 48.51 +/- 16.04 uM | Not Available | Ovine | | details | | Serum | Detected and Quantified | 47.5571 +/- 13.8235 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 40.3043 +/- 10.3061 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 48.8208 +/- 13.3975 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 42.0713 +/- 17.0498 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 43.6271 +/- 13.2608 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 44.7366 +/- 10.1035 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 42.8526 +/- 11.5519 uM | Normal | Ovine | | details |
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