| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-07-13 19:42:42 UTC |
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| Update Date | 2016-07-20 20:56:38 UTC |
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| Lmdb | LMDB00116 |
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| Secondary Accession Numbers | None |
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| Metabolite Identification |
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| Common Name | Sphingosine |
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| Description | Sphingosine, also known as (4E)-sphingenine, belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. This leads to the formation of sphingosine-1-phosphate, a potent signaling lipid. Sphingosine is a 18-carbon amino alcohol with a long unsaturated hydrocarbon chain. Sphingosine is a very strong basic compound (based on its pKa). Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. Sphingosine exists in all eukaryotes, ranging from yeast to humans. Within humans, sphingosine participates in a number of enzymatic reactions. In particular, sphingosine can be converted into sphingosine 1-phosphate through the action of the enzyme sphingosine kinase 2. In addition, sphingosine can be biosynthesized from sphingosine 1-phosphate; which is mediated by the enzyme sphingosine-1-phosphate phosphatase 2. In humans, sphingosine is involved in the metabolic disorder called the fabry disease pathway. Outside of the human body, Sphingosine has been detected, but not quantified in, several different foods, such as towel gourds, common walnuts, sunburst squash (pattypan squash), common persimmons, and oil-seed camellia. This could make sphingosine a potential biomarker for the consumption of these foods. Sphingosine can be phosphorylated in vivo via two kinases, sphingosine kinase type 1 and sphingosine kinase type 2. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (-)-D-Erythro-sphingosine | HMDB | | (2S,3R)-Sphingosine | HMDB | | (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol | HMDB | | (4E)-Sphingenine | HMDB | | 4-Sphingenine | HMDB | | 4-trans-Sphingenine | HMDB | | [R-[R*,s*-(e)]]-2-amino-4-octadecene-1,3-diol | HMDB |
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| Chemical Formula | C18H37NO2 |
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| Average Molecular Weight | 299.4919 |
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| Monoisotopic Molecular Weight | 299.282429433 |
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| IUPAC Name | (4E)-2-aminooctadec-4-ene-1,3-diol |
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| Traditional Name | sphingosine |
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| CAS Registry Number | 123-78-4 |
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| SMILES | CCCCCCCCCCCCC\C=C\C(O)C(N)CO |
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| InChI Identifier | InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+ |
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| InChI Key | WWUZIQQURGPMPG-CCEZHUSRSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. |
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| Kingdom | Organic compounds |
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| Super Class | Organic nitrogen compounds |
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| Class | Organonitrogen compounds |
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| Sub Class | Amines |
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| Direct Parent | 1,2-aminoalcohols |
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| Alternative Parents | |
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| Substituents | - Secondary alcohol
- 1,2-aminoalcohol
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Primary alcohol
- Organooxygen compound
- Primary aliphatic amine
- Alcohol
- 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 but not 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 | | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03dr-9260000000-2ff04e0afd9e8b2f0851 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-003r-8915100000-51f94df9cbd9e00dbf76 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-001i-0090000000-67307f0b7f6f858af400 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a59-9010000000-e66065dfabaedfa9a7f2 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0api-9000000000-a5c7c01555839f61ab3d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f89-0092000000-c0188d9e3166e42d0a72 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-02ai-2390000000-23fd78f38dca1695f653 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4m-6940000000-bd71a7546dbbc9a6e83b | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0090000000-310f8ec2f529dd63e5b7 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-07d4-4090000000-3ec929924c6bbc7293e0 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9030000000-c344fe4fe9af07abf710 | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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