1.0 2018-10-10 21:42:31 UTC 2020-06-04 19:22:32 UTC BMDB0063622 BMDB63622 Cer(d18:0/20:1(11Z)) Cer(d18:0/20:1(11Z)), also known as N-11Z-eicosenoyl-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(d18:0/20:1(11Z)) is a colorless solid that consists of a saturated 18-carbon sphingoid base with an attached unsaturated 11Z-eicosenoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481). Ceramide N-(11Z-Eicosenoyl)-sphinganine Ceramide(D18:0/20:1(11Z)) N-(11Z-Eicosenoyl)-dihydrosphingosine N-(11Z-Eicosenoyl)-D-erythro-sphinganine C38H75NO3 594.022 593.574695279 (11Z)-N-[(2S)-1,3-dihydroxyoctadecan-2-yl]icos-11-enamide (11Z)-N-[(2S)-1,3-dihydroxyoctadecan-2-yl]icos-11-enamide CCCCCCCCCCCCCCCC(O)[C@H](CO)NC(=O)CCCCCCCCC\C=C/CCCCCCCC InChI=1S/C38H75NO3/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-38(42)39-36(35-40)37(41)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h17-18,36-37,40-41H,3-16,19-35H2,1-2H3,(H,39,42)/b18-17-/t36-,37?/m0/s1 PULBITQLTXYVQX-VQNGLQQLSA-N belongs to the class of organic compounds known as long-chain ceramides. These are ceramides bearing a long chain fatty acid. Organic compounds Lipids and lipid-like molecules Sphingolipids Ceramides Long-chain ceramides Carbonyl compounds Hydrocarbon derivatives N-acyl amines Organic oxides Organonitrogen compounds Primary alcohols Secondary alcohols Secondary carboxylic acid amides Alcohol Aliphatic acyclic compound Carbonyl group Carboxamide group Carboxylic acid derivative Fatty acyl Fatty amide Hydrocarbon derivative Long-chain ceramide N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Primary alcohol Secondary alcohol Secondary carboxylic acid amide Aliphatic acyclic compounds logp 10.04 ALOGPS logs -7.35 ALOGPS logp 12.49 ChemAxon pka_strongest_acidic 13.83 ChemAxon pka_strongest_basic -1 ChemAxon iupac (11Z)-N-[(2S)-1,3-dihydroxyoctadecan-2-yl]icos-11-enamide ChemAxon average_mass 594.022 ChemAxon mono_mass 593.574695279 ChemAxon smiles CCCCCCCCCCCCCCCC(O)[C@H](CO)NC(=O)CCCCCCCCC\C=C/CCCCCCCC ChemAxon formula C38H75NO3 ChemAxon inchi InChI=1S/C38H75NO3/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-38(42)39-36(35-40)37(41)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h17-18,36-37,40-41H,3-16,19-35H2,1-2H3,(H,39,42)/b18-17-/t36-,37?/m0/s1 ChemAxon inchikey PULBITQLTXYVQX-VQNGLQQLSA-N ChemAxon polar_surface_area 69.56 ChemAxon refractivity 184.33 ChemAxon polarizability 80.49 ChemAxon rotatable_bond_count 34 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Milk 0.07 +/- 0.01 uM Commercial skim milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.12 +/- 0.01 uM Commercial 1% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.144 +/- 0.002 uM Commercial 2% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.22 +/- 0.01 uM Commercial 3.25% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 FDB097424 89054488 Dickson RC: Sphingolipid functions in Saccharomyces cerevisiae: comparison to mammals. Annu Rev Biochem. 1998;67:27-48. doi: 10.1146/annurev.biochem.67.1.27. 9759481 Bowser PA, Gray GM: Sphingomyelinase in pig and human epidermis. J Invest Dermatol. 1978 Jun;70(6):331-5. 25935 Tserng KY, Griffin RL: Ceramide metabolite, not intact ceramide molecule, may be responsible for cellular toxicity. Biochem J. 2004 Jun 15;380(Pt 3):715-22. doi: 10.1042/BJ20031733. 14998372