Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:24 UTC |
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HMDB ID | HMDB0004956 |
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Secondary Accession Numbers | - HMDB0000831
- HMDB00831
- HMDB04956
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Metabolite Identification |
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Common Name | Cer(d18:1/24:0) |
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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. |
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Structure | [H][C@@](CO)(NC(=O)CCCCCCCCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC InChI=1S/C42H83NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-42(46)43-40(39-44)41(45)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,40-41,44-45H,3-34,36,38-39H2,1-2H3,(H,43,46)/b37-35+/t40-,41+/m0/s1 |
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Synonyms | Value | Source |
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C24 Cer | ChEBI | Cer(d18:1/24:0) | ChEBI | N-(Tetracosanoyl)-sphing-4-enine | ChEBI | N-(Tetracosanoyl)ceramide | ChEBI | N-(Tetracosanoyl)sphing-4-enine | ChEBI | N-Lignoceroylsphingosine | ChEBI | N-Tetracosanoylsphing-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 | N-Acylsphingosine | HMDB | N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-octadecanamide | HMDB | Ceramide (d18:1/24:0) | ChEBI | C24-Ceramide | HMDB | C24:0 Ceramide | HMDB | Cer d18:1/24:0 | HMDB | Ceramide (d18:1,C24:0) | HMDB | Ceramide 24 | HMDB | Ceramide d18:1/24:0 | HMDB | Ceramide(d18:1/24:0) | HMDB | D-erythro-1,3-Dihydroxy-2-tetracosanoylamido-trans-4-octadecene | HMDB | N-Tetracosanoyl C18-sphingosine | HMDB |
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Chemical Formula | C42H83NO3 |
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Average Molecular Weight | 650.1133 |
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Monoisotopic Molecular Weight | 649.637295527 |
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IUPAC Name | N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]tetracosanamide |
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Traditional Name | C24 cer |
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CAS Registry Number | 34435-05-7 |
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SMILES | [H][C@@](CO)(NC(=O)CCCCCCCCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C42H83NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-42(46)43-40(39-44)41(45)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,40-41,44-45H,3-34,36,38-39H2,1-2H3,(H,43,46)/b37-35+/t40-,41+/m0/s1 |
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InChI Key | ZJVVOYPTFQEGPH-AUTSUKAISA-N |
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Chemical Taxonomy |
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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 | |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0 | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Cer(d18:1/24:0),1TMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 5012.6 | Semi standard non polar | 33892256 | Cer(d18:1/24:0),1TMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 4737.4 | Standard non polar | 33892256 | Cer(d18:1/24:0),1TMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 5405.7 | Standard polar | 33892256 | Cer(d18:1/24:0),1TMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 5037.0 | Semi standard non polar | 33892256 | Cer(d18:1/24:0),1TMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 4673.0 | Standard non polar | 33892256 | Cer(d18:1/24:0),1TMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 5138.8 | Standard polar | 33892256 | Cer(d18:1/24:0),1TMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C | 4870.9 | Semi standard non polar | 33892256 | Cer(d18:1/24:0),1TMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C | 4697.0 | Standard non polar | 33892256 | Cer(d18:1/24:0),1TMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C | 5367.1 | Standard polar | 33892256 | Cer(d18:1/24:0),2TMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 4981.3 | Semi standard non polar | 33892256 | Cer(d18:1/24:0),2TMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 4532.8 | Standard non polar | 33892256 | Cer(d18:1/24:0),2TMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 4845.4 | Standard polar | 33892256 | Cer(d18:1/24:0),2TMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C | 4866.5 | Semi standard non polar | 33892256 | Cer(d18:1/24:0),2TMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C | 4609.2 | Standard non polar | 33892256 | Cer(d18:1/24:0),2TMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C | 5103.1 | Standard polar | 33892256 | Cer(d18:1/24:0),2TMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C | 4909.3 | Semi standard non polar | 33892256 | Cer(d18:1/24:0),2TMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C | 4547.2 | Standard non polar | 33892256 | Cer(d18:1/24:0),2TMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C | 4853.4 | Standard polar | 33892256 | Cer(d18:1/24:0),3TMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C | 4898.3 | Semi standard non polar | 33892256 | Cer(d18:1/24:0),3TMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C | 4516.7 | Standard non polar | 33892256 | Cer(d18:1/24:0),3TMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C | 4627.2 | Standard polar | 33892256 | Cer(d18:1/24:0),1TBDMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 5223.7 | Semi standard non polar | 33892256 | Cer(d18:1/24:0),1TBDMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 4853.3 | Standard non polar | 33892256 | Cer(d18:1/24:0),1TBDMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 5347.3 | Standard polar | 33892256 | Cer(d18:1/24:0),1TBDMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 5223.3 | Semi standard non polar | 33892256 | Cer(d18:1/24:0),1TBDMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 4765.8 | Standard non polar | 33892256 | Cer(d18:1/24:0),1TBDMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 5123.2 | Standard polar | 33892256 | Cer(d18:1/24:0),1TBDMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C | 5122.5 | Semi standard non polar | 33892256 | Cer(d18:1/24:0),1TBDMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C | 4812.4 | Standard non polar | 33892256 | Cer(d18:1/24:0),1TBDMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C | 5309.1 | Standard polar | 33892256 | Cer(d18:1/24:0),2TBDMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 5486.2 | Semi standard non polar | 33892256 | Cer(d18:1/24:0),2TBDMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 4747.8 | Standard non polar | 33892256 | Cer(d18:1/24:0),2TBDMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 4913.0 | Standard polar | 33892256 | Cer(d18:1/24:0),2TBDMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C | 5396.8 | Semi standard non polar | 33892256 | Cer(d18:1/24:0),2TBDMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C | 4815.1 | Standard non polar | 33892256 | Cer(d18:1/24:0),2TBDMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C | 5135.6 | Standard polar | 33892256 | Cer(d18:1/24:0),2TBDMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C | 5410.8 | Semi standard non polar | 33892256 | Cer(d18:1/24:0),2TBDMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C | 4772.8 | Standard non polar | 33892256 | Cer(d18:1/24:0),2TBDMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C | 4936.5 | Standard polar | 33892256 |
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