Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2008-09-26 14:11:32 UTC |
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Update Date | 2022-11-30 19:03:54 UTC |
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HMDB ID | HMDB0010697 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cer(t18:0/16:0) |
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Description | Cer(t18:0/16:0), also known as N-hexadecanoyl-4R-hydroxy-sphinganine, 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(t18:0/16:0) is a colorless solid that consists of a saturated 18-carbon sphingoid base with an attached saturated hexadecanoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481 ). |
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Structure | [H][C@@](O)(C(O)CCCCCCCCCCCCCC)[C@]([H])(CO)NC(=O)CCCCCCCCCCCCCCC InChI=1S/C34H69NO4/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(38)35-31(30-36)34(39)32(37)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h31-32,34,36-37,39H,3-30H2,1-2H3,(H,35,38)/t31-,32?,34-/m0/s1 |
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Synonyms | Value | Source |
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Ceramide (t18:0/16:0) | HMDB | Ceramide | HMDB | N-(Hexadecanoyl)-4R-hydroxy-sphinganine | HMDB | Ceramide(t18:0/16:0) | HMDB | N-(Hexadecanoyl)-4R-hydroxy-dihydrosphingosine | HMDB | N-(Hexadecanoyl)-4R-hydroxy-D-erythro-sphinganine | HMDB | N-[(2S,3S)-1,3,4-Trihydroxyoctadecan-2-yl]hexadecanimidate | HMDB |
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Chemical Formula | C34H69NO4 |
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Average Molecular Weight | 555.916 |
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Monoisotopic Molecular Weight | 555.522659701 |
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IUPAC Name | N-[(2S,3S)-1,3,4-trihydroxyoctadecan-2-yl]hexadecanamide |
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Traditional Name | N-[(2S,3S)-1,3,4-trihydroxyoctadecan-2-yl]hexadecanamide |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](O)(C(O)CCCCCCCCCCCCCC)[C@]([H])(CO)NC(=O)CCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C34H69NO4/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(38)35-31(30-36)34(39)32(37)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h31-32,34,36-37,39H,3-30H2,1-2H3,(H,35,38)/t31-,32?,34-/m0/s1 |
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InChI Key | IVBULNXGVIHEKN-AUOMWKRBSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phytoceramides. These are n-acylated 4-hydroxysphinganine. |
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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 | Phytoceramides |
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Alternative Parents | |
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Substituents | - N-acyl-4-hydroxysphinganine
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Carboxamide group
- Secondary alcohol
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Polyol
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Alcohol
- Organic nitrogen compound
- Carbonyl group
- Primary alcohol
- Hydrocarbon derivative
- 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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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 | Not Available | 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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Cer(t18:0/16:0),1TMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O[Si](C)(C)C)C(O)CCCCCCCCCCCCCC | 4204.0 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),1TMS,isomer #2 | CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C(CCCCCCCCCCCCCC)O[Si](C)(C)C | 4217.8 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),1TMS,isomer #3 | CCCCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C)[C@H](O)C(O)CCCCCCCCCCCCCC | 4164.4 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),1TMS,isomer #4 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@H](O)C(O)CCCCCCCCCCCCCC)[Si](C)(C)C | 4122.8 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),2TMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(O)CCCCCCCCCCCCCC | 4165.8 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),2TMS,isomer #2 | CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O[Si](C)(C)C)C(CCCCCCCCCCCCCC)O[Si](C)(C)C | 4152.2 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),2TMS,isomer #3 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@H](O[Si](C)(C)C)C(O)CCCCCCCCCCCCCC)[Si](C)(C)C | 4193.0 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),2TMS,isomer #4 | CCCCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C)[C@H](O)C(CCCCCCCCCCCCCC)O[Si](C)(C)C | 4150.1 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),2TMS,isomer #5 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@H](O)C(CCCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C | 4167.9 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),2TMS,isomer #6 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@H](O)C(O)CCCCCCCCCCCCCC)[Si](C)(C)C | 4133.5 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),3TMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(CCCCCCCCCCCCCC)O[Si](C)(C)C | 4150.7 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),3TMS,isomer #2 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(O)CCCCCCCCCCCCCC)[Si](C)(C)C | 4200.1 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),3TMS,isomer #3 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@H](O[Si](C)(C)C)C(CCCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C | 4201.1 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),3TMS,isomer #4 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@H](O)C(CCCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C | 4193.6 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),4TMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(CCCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C | 4217.2 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),4TMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(CCCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C | 4008.3 | Standard non polar | 33892256 | Cer(t18:0/16:0),4TMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(CCCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C | 4079.6 | Standard polar | 33892256 | Cer(t18:0/16:0),1TBDMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)C(O)CCCCCCCCCCCCCC | 4466.3 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),1TBDMS,isomer #2 | CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C(CCCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C | 4498.8 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),1TBDMS,isomer #3 | CCCCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](O)C(O)CCCCCCCCCCCCCC | 4464.4 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),1TBDMS,isomer #4 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@H](O)C(O)CCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C | 4396.3 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),2TBDMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(O)CCCCCCCCCCCCCC | 4708.4 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),2TBDMS,isomer #2 | CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)C(CCCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C | 4734.3 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),2TBDMS,isomer #3 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)C(O)CCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C | 4657.1 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),2TBDMS,isomer #4 | CCCCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](O)C(CCCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C | 4707.2 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),2TBDMS,isomer #5 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@H](O)C(CCCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 4658.6 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),2TBDMS,isomer #6 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](O)C(O)CCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C | 4613.1 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),3TBDMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(CCCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C | 4942.1 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),3TBDMS,isomer #2 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(O)CCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C | 4879.8 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),3TBDMS,isomer #3 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)C(CCCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 4909.5 | Semi standard non polar | 33892256 | Cer(t18:0/16:0),3TBDMS,isomer #4 | CCCCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](O)C(CCCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 4900.6 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (1 TMS) - 70eV, Positive | splash10-020s-2342893000-3f15f4057672b8300b42 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS ("Cer(t18:0/16:0),1TMS,#1" TMS) - 70eV, Positive | Not Available | 2021-10-14 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TMS_2_5) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TMS_2_6) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TMS_3_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TMS_3_2) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TMS_3_3) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TMS_3_4) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TBDMS_1_4) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TBDMS_2_4) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TBDMS_2_5) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cer(t18:0/16:0) GC-MS (TBDMS_2_6) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cer(t18:0/16:0) 10V, Negative-QTOF | splash10-0udi-0000090000-5c13869ee8700a11d1e7 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cer(t18:0/16:0) 20V, Negative-QTOF | splash10-0fa2-0091040000-c73438973678bb3720d8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cer(t18:0/16:0) 40V, Negative-QTOF | splash10-001i-1090000000-cf30b6887f4521911de3 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cer(t18:0/16:0) 10V, Positive-QTOF | splash10-0a4r-1010090000-11fd82136e0ff138cb0e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cer(t18:0/16:0) 20V, Positive-QTOF | splash10-0abi-9244050000-b99f74d2112c95dbee26 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cer(t18:0/16:0) 40V, Positive-QTOF | splash10-0pi0-9312000000-920a4430e331aea381a6 | 2021-09-24 | Wishart Lab | View Spectrum |
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General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
- Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
- Pruett ST, Bushnev A, Hagedorn K, Adiga M, Haynes CA, Sullards MC, Liotta DC, Merrill AH Jr: Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols. J Lipid Res. 2008 Aug;49(8):1621-39. doi: 10.1194/jlr.R800012-JLR200. Epub 2008 May 21. [PubMed:18499644 ]
- Hannun YA, Obeid LM: Ceramide: an intracellular signal for apoptosis. Trends Biochem Sci. 1995 Feb;20(2):73-7. [PubMed:7701566 ]
- Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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