Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:07:07 UTC |
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Update date | 2019-11-26 03:01:08 UTC |
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Primary ID | FDB006397 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Ceramide |
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Description | Ceramides (N-acylsphingosine) are one of the hydrolysis byproducts of sphingomyelin by the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis (PMID 25935) and many other tissues. They 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). Is key in the biosynthesis of glycosphingolipids and gangliosides. Ceramide is found in rice. |
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CAS Number | 74713-60-3 |
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Structure | |
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Synonyms | Synonym | Source |
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Cer(d18:1/12:0) | ChEBI | Dodecyl sphingosine | ChEBI | Laurylsphingosine | ChEBI | N-(Dodecanoyl)ceramide | ChEBI | N-(Dodecanoyl)sphing-4-enine | ChEBI | N-(Lauroyl)ceramide | ChEBI | N-(Lauroyl)sphing-4-enine | ChEBI | N-Dodecanoylsphing-4-enine | ChEBI | N-Lauroylsphing-4-enine | ChEBI | N-Lauroylsphingosine | 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 | N-Acylsphingosine | HMDB | N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-octadecanamide | HMDB | C12-Ceramide | HMDB | Cer d18:1/12:0 | HMDB | Ceramide (d18:1,C12:0) | HMDB | Ceramide (d18:1/12:0) | HMDB | Ceramide 12 | HMDB | Ceramide(d18:1/12:0) | HMDB | N-Lauroyl-D-erythro-sphingosine | HMDB | N-Laurylsphingosine | HMDB | (2S,3R,4E)-2-acylamino-1,3-octadec-4-enediol | biospider | (2S,3R,4E)-2-acylaminooctadec-4-ene-1,3-diol | biospider | CER | biospider | Cer(D18:1/12:0) | ChEBI | Ceramide (egg) | biospider | Ceramide 1-phosphate | biospider | Ceramide phosphate | biospider | Ceramides | biospider | N-((2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl)stearamide | biospider | N-[(1S,2R,3e)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-octadecanamide | HMDB | N-acylsphingosine | biospider | SPL | biospider |
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Predicted Properties | |
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Chemical Formula | C30H59NO3 |
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IUPAC name | N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]dodecanamide |
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InChI Identifier | InChI=1S/C30H59NO3/c1-3-5-7-9-11-13-14-15-16-18-19-21-23-25-29(33)28(27-32)31-30(34)26-24-22-20-17-12-10-8-6-4-2/h23,25,28-29,32-33H,3-22,24,26-27H2,1-2H3,(H,31,34)/b25-23+/t28-,29+/m0/s1 |
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InChI Key | HXFPPRPLRSPNIB-VARSQMIESA-N |
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Isomeric SMILES | CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCC |
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Average Molecular Weight | 481.7944 |
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Monoisotopic Molecular Weight | 481.449494759 |
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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 - Experimental |
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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, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-022i-5785598000-7031136168734e1ef5ee | Spectrum | Predicted GC-MS | Ceramide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-03di-2090000000-ae80000c40a296a1c5d8 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-03di-2090000000-a13bd310025f03a29721 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-03di-2090000000-8d5084b0da3675b3f3f3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-03di-2090000000-d4824df02fcc2092417c | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-03di-2090000000-f919f09dc660be85f13e | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0000900000-fe0f573db63b1b90fd2f | 2017-10-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-0050900000-612b7fe1fb533df6232b | 2017-10-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03e9-0090600000-9abebdbdb27db5a25cb2 | 2017-10-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0000900000-fa0543ff22d51d18b573 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0010900000-3de9968cb166260af69f | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001k-0220900000-1f62f1430f619c4887d9 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0000900000-2b1019f1dfd77202b1a5 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0000900000-2b1019f1dfd77202b1a5 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-0000900000-aa4c78e902645a2bb092 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0000900000-5acec5af0818f408e044 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-0050900000-f3ad47a5043cb0aa6c70 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03e9-0090600000-797db203768da46183b0 | 2021-09-25 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 4446675 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C00195 |
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Pubchem Compound ID | 5283562 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 16197 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB04947 |
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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 | CERAMIDE |
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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 | Cer |
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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 | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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