Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:31:22 UTC |
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Update date | 2017-03-11 23:00:28 UTC |
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Primary ID | FDB023542 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Ceramide (d18:1/26:0) |
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Description | Cer(d18:1/26:0), also known as N-hexacosanoyl-sphing-4-enine, is a ceramide (Cer). Ceramides are members of the class of compounds known as sphingolipids (SPs), or glycosylceramides. SPs are lipids containing a backbone of sphingoid bases (e.g. sphingosine or sphinganine) that are often covalently bound to a fatty acid derivative through N-acylation. SPs are found in cell membranes, particularly in peripheral nerve cells and the cells found in the central nervous system (including the brain and spinal cord). Sphingolipids are extremely versatile molecules that have functions controlling fundamental cellular processes such as cell division, differentiation, and cell death. Impairments associated with sphingolipid metabolism are associated with many common human diseases such as diabetes, various cancers, microbial infections, diseases of the cardiovascular and respiratory systems, Alzheimer’s disease and other neurological syndromes. The biosynthesis and catabolism of sphingolipids involves a large number of intermediate metabolites where many different enzymes are involved. Simple sphingolipids, which include the sphingoid bases and ceramides, make up the early products of the sphingolipid synthetic pathways, while complex sphingolipids may be formed by the addition of head groups to the ceramide template (Wikipedia). In humans, ceramides are phosphorylated to ceramide phosphates (CerPs) through the action of a specific ceramide kinase (CerK). Ceramide phosphates are important metabolites of ceramides as they act as a mediators of the inflammatory response. Ceramides are also one of the hydrolysis byproducts of sphingomyelins (SMs) through the action of the enzyme sphingomyelin phosphodiesterase, which has been identified in the subcellular fractions of human epidermis (PMID: 25935) and many other tissues. Ceramides can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID: 14998372). Ceramides are key in the biosynthesis of glycosphingolipids and gangliosides. In terms of its appearance and structure, Cer(d18:1/26:0) is a colorless solid that consists of an unsaturated 18-carbon sphingoid base with an attached saturated hexacosanoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481). |
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CAS Number | 104404-17-3 |
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Structure | |
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Synonyms | Synonym | Source |
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C26 Cer | ChEBI | N-(Hexacosanoyl)ceramide | ChEBI | N-(Hexacosanoyl)sphing-4-enine | ChEBI | N-Hexacosanoylsphing-4-enine | ChEBI | (2S,3R,4E)-2-Acylamino-1,3-octadec-4-enediol | HMDB | (2S,3R,4E)-2-Acylaminooctadec-4-ene-1,3-diol | HMDB | Cer | HMDB | Ceramide | HMDB | Ceramide (D18:1/26:0) | HMDB | N-Acylsphingosine | HMDB | N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-octadecanamide | HMDB | N-(Hexacosanoyl)-sphing-4-enine | HMDB | Ceramide(D18:1/26:0) | HMDB | N-(Hexacosanoyl)-sphingosine | HMDB | N-(Hexacosanoyl)-D-erythro-sphingosine | HMDB | N-(Hexacosanoyl)-4-sphingenine | HMDB | N-(Hexacosanoyl)-D-sphingosine | HMDB | N-(Hexacosanoyl)-sphingenine | HMDB | N-(Hexacosanoyl)-erythro-4-sphingenine | HMDB | Cer(D18:1/26:0) | ChEBI |
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Predicted Properties | |
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Chemical Formula | C44H87NO3 |
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IUPAC name | N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]hexacosanamide |
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InChI Identifier | InChI=1S/C44H87NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-44(48)45-42(41-46)43(47)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2/h37,39,42-43,46-47H,3-36,38,40-41H2,1-2H3,(H,45,48)/b39-37+/t42-,43+/m0/s1 |
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InChI Key | CJROVRTUSFQVMR-GVOPMEMSSA-N |
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Isomeric SMILES | CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)\C=C\CCCCCCCCCCCCC |
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Average Molecular Weight | 678.1665 |
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Monoisotopic Molecular Weight | 677.668595655 |
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Classification |
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Description | Belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid. |
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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 | Ceramides |
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Direct Parent | Ceramides |
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Alternative Parents | |
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Substituents | - Ceramide
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Carboxamide group
- Secondary alcohol
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Alcohol
- Organic nitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: Organoleptic effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Ceramide (d18:1/26:0), TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Ceramide (d18:1/26:0), TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Ceramide (d18:1/26:0), TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Ceramide (d18:1/26:0), TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Ceramide (d18:1/26:0), TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Ceramide (d18:1/26:0), TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Ceramide (d18:1/26:0), TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Ceramide (d18:1/26:0), TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Ceramide (d18:1/26:0), TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0000009000-fc12ec7f373bc36fecac | 2017-10-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01t9-0050009000-d7f4ac7869d9a81bad7d | 2017-10-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03e9-0090006000-71ee599024cabab4acfa | 2017-10-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0000009000-43e8b87ae8fa46301afa | 2021-09-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01t9-0050009000-1a4d3a44ae60d8fbe1af | 2021-09-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03e9-0090006000-be9ad25efee6e2eb7acd | 2021-09-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0000009000-db0e7db2b458c26e0c5f | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0000009000-db0e7db2b458c26e0c5f | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-0000009000-3eacb775e96413fc2495 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0000009000-ce52ccd5949c4f7977aa | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0010009000-804b0d55a7076709aa86 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004o-0022009000-7e3a5ca47cc429f981c7 | 2021-09-25 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 4446683 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C00195 |
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Pubchem Compound ID | 5283570 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB04955 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Lactase-phlorizin hydrolase | LCT | P09848 | Glucosylceramidase | GBA | P04062 | Acid ceramidase | ASAH1 | Q13510 | Putative neutral ceramidase C | ASAH2C | P0C7U2 | Alkaline ceramidase 2 | ACER2 | Q5QJU3 | Neutral ceramidase | ASAH2 | Q9NR71 | Alkaline ceramidase 1 | ACER1 | Q8TDN7 | Phosphatidylcholine:ceramide cholinephosphotransferase 2 | SGMS2 | Q8NHU3 | Phosphatidylcholine:ceramide cholinephosphotransferase 1 | SGMS1 | Q86VZ5 | Ganglioside GM2 activator | GM2A | P17900 | Sphingosine-1-phosphate lyase 1 | SGPL1 | O95470 | Galactocerebrosidase | GALC | P54803 | N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase | PIGL | Q9Y2B2 | Sphingomyelin phosphodiesterase | SMPD1 | P17405 | Ceramide glucosyltransferase | UGCG | Q16739 | Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q | PIGQ | Q9BRB3 | Phosphatidylinositol N-acetylglucosaminyltransferase subunit A | PIGA | P37287 | Phosphatidylinositol N-acetylglucosaminyltransferase subunit H | PIGH | Q14442 | Phosphatidylinositol N-acetylglucosaminyltransferase subunit P | PIGP | P57054 | Phosphatidylinositol N-acetylglucosaminyltransferase subunit C | PIGC | Q92535 | 2-hydroxyacylsphingosine 1-beta-galactosyltransferase | UGT8 | Q16880 | Collagen type IV alpha-3-binding protein | COL4A3BP | Q9Y5P4 | T-cell surface glycoprotein CD1e, membrane-associated | CD1E | P15812 | Epididymal secretory protein E1 | NPC2 | P61916 | Ceramide synthase 1 | CERS1 | P27544 | Antigen-presenting glycoprotein CD1d | CD1D | P15813 | GPI mannosyltransferase 1 | PIGM | Q9H3S5 | Phosphatidylinositol-glycan biosynthesis class W protein | PIGW | Q7Z7B1 | Phosphatidylinositol-glycan biosynthesis class X protein | PIGX | Q8TBF5 | GPI mannosyltransferase 4 | PIGZ | Q86VD9 | Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase | B3GNT5 | Q9BYG0 | Beta-1,3-galactosyltransferase 5 | B3GALT5 | Q9Y2C3 | GPI mannosyltransferase 3 | PIGB | Q92521 | Phosphatidylinositol-glycan biosynthesis class F protein | PIGF | Q07326 | GPI ethanolamine phosphate transferase 2 | PIGG | Q5H8A4 | GPI ethanolamine phosphate transferase 1 | PIGN | O95427 | GPI ethanolamine phosphate transferase 3 | PIGO | Q8TEQ8 | GPI transamidase component PIG-S | PIGS | Q96S52 | GPI transamidase component PIG-T | PIGT | Q969N2 | Phosphatidylinositol glycan anchor biosynthesis class U protein | PIGU | Q9H490 | GPI mannosyltransferase 2 | PIGV | Q9NUD9 | Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y | PIGY | Q3MUY2 | Non-lysosomal glucosylceramidase | GBA2 | Q9HCG7 | Protein FAN | NSMAF | Q92636 | GPI-anchor transamidase | PIGK | Q92643 |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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