Record Information |
---|
Version | 1.0 |
---|
Creation Date | 2016-05-25 22:48:33 UTC |
---|
Update Date | 2016-11-09 01:18:13 UTC |
---|
Accession Number | CHEM026130 |
---|
Identification |
---|
Common Name | Ceramide |
---|
Class | Small Molecule |
---|
Description | |
---|
Contaminant Sources | |
---|
Contaminant Type | Not Available |
---|
Chemical Structure | |
---|
Synonyms | Value | Source |
---|
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 |
|
---|
Chemical Formula | C30H59NO3 |
---|
Average Molecular Mass | 481.794 g/mol |
---|
Monoisotopic Mass | 481.449 g/mol |
---|
CAS Registry Number | 74713-60-3 |
---|
IUPAC Name | N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]dodecanamide |
---|
Traditional Name | N-(dodecanoyl)-ceramide |
---|
SMILES | CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCC |
---|
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 |
---|
InChI Key | HXFPPRPLRSPNIB-VARSQMIESA-N |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Sphingolipids |
---|
Sub Class | Ceramides |
---|
Direct Parent | Ceramides |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Biological Properties |
---|
Status | Detected and Not Quantified |
---|
Origin | Not Available |
---|
Cellular Locations | Not Available |
---|
Biofluid Locations | Not Available |
---|
Tissue Locations | Not Available |
---|
Pathways | Not Available |
---|
Applications | Not Available |
---|
Biological Roles | Not Available |
---|
Chemical Roles | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Appearance | Not Available |
---|
Experimental Properties | Property | Value |
---|
Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
|
---|
Predicted Properties | |
---|
Spectra |
---|
Spectra | Spectrum Type | Description | Splash Key | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-022i-5785598000-7031136168734e1ef5ee | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-03di-2090000000-ae80000c40a296a1c5d8 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-03di-2090000000-a13bd310025f03a29721 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-03di-2090000000-8d5084b0da3675b3f3f3 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-03di-2090000000-d4824df02fcc2092417c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-03di-2090000000-f919f09dc660be85f13e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0000900000-fe0f573db63b1b90fd2f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-0050900000-612b7fe1fb533df6232b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03e9-0090600000-9abebdbdb27db5a25cb2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0000900000-fa0543ff22d51d18b573 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0010900000-3de9968cb166260af69f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001k-0220900000-1f62f1430f619c4887d9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0000900000-2b1019f1dfd77202b1a5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0000900000-2b1019f1dfd77202b1a5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-0000900000-aa4c78e902645a2bb092 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0000900000-5acec5af0818f408e044 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-0050900000-f3ad47a5043cb0aa6c70 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03e9-0090600000-797db203768da46183b0 | Spectrum |
|
---|
Toxicity Profile |
---|
Route of Exposure | Not Available |
---|
Mechanism of Toxicity | Not Available |
---|
Metabolism | Not Available |
---|
Toxicity Values | Not Available |
---|
Lethal Dose | Not Available |
---|
Carcinogenicity (IARC Classification) | Not Available |
---|
Uses/Sources | Not Available |
---|
Minimum Risk Level | Not Available |
---|
Health Effects | Not Available |
---|
Symptoms | Not Available |
---|
Treatment | Not Available |
---|
Concentrations |
---|
| Not Available |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB0004947 |
---|
FooDB ID | FDB006397 |
---|
Phenol Explorer ID | Not Available |
---|
KNApSAcK ID | Not Available |
---|
BiGG ID | Not Available |
---|
BioCyc ID | CERAMIDE |
---|
METLIN ID | 7200 |
---|
PDB ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
Chemspider ID | 4446675 |
---|
ChEBI ID | 72956 |
---|
PubChem Compound ID | 5283562 |
---|
Kegg Compound ID | C00195 |
---|
YMDB ID | Not Available |
---|
ECMDB ID | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
MSDS | Not Available |
---|
General References | 1. Deguchi H, Yegneswaran S, Griffin JH: Sphingolipids as bioactive regulators of thrombin generation. J Biol Chem. 2004 Mar 26;279(13):12036-42. Epub 2004 Jan 13. | 2. Watanabe R, Wu K, Paul P, Marks DL, Kobayashi T, Pittelkow MR, Pagano RE: Up-regulation of glucosylceramide synthase expression and activity during human keratinocyte differentiation. J Biol Chem. 1998 Apr 17;273(16):9651-5. | 3. Mari M, Colell A, Morales A, Paneda C, Varela-Nieto I, Garcia-Ruiz C, Fernandez-Checa JC: Acidic sphingomyelinase downregulates the liver-specific methionine adenosyltransferase 1A, contributing to tumor necrosis factor-induced lethal hepatitis. J Clin Invest. 2004 Mar;113(6):895-904. | 4. Adams JM 2nd, Pratipanawatr T, Berria R, Wang E, DeFronzo RA, Sullards MC, Mandarino LJ: Ceramide content is increased in skeletal muscle from obese insulin-resistant humans. Diabetes. 2004 Jan;53(1):25-31. | 5. Holleran WM, Ginns EI, Menon GK, Grundmann JU, Fartasch M, McKinney CE, Elias PM, Sidransky E: Consequences of beta-glucocerebrosidase deficiency in epidermis. Ultrastructure and permeability barrier alterations in Gaucher disease. J Clin Invest. 1994 Apr;93(4):1756-64. | 6. Marchesini S, Demasi L, Cestone P, Preti A, Agmon V, Dagan A, Navon R, Gatt S: Sulforhodamine GM1-ganglioside: synthesis and physicochemical properties. Chem Phys Lipids. 1994 Aug 8;72(2):143-52. | 7. Poliak S, Gollan L, Salomon D, Berglund EO, Ohara R, Ranscht B, Peles E: Localization of Caspr2 in myelinated nerves depends on axon-glia interactions and the generation of barriers along the axon. J Neurosci. 2001 Oct 1;21(19):7568-75. | 8. Ohnishi Y, Okino N, Ito M, Imayama S: Ceramidase activity in bacterial skin flora as a possible cause of ceramide deficiency in atopic dermatitis. Clin Diagn Lab Immunol. 1999 Jan;6(1):101-4. | 9. Humbert P: [Functional consequences of cutaneous lipid perturbation]. Pathol Biol (Paris). 2003 Jul;51(5):271-4. | 10. Ghadially R, Brown BE, Sequeira-Martin SM, Feingold KR, Elias PM: The aged epidermal permeability barrier. Structural, functional, and lipid biochemical abnormalities in humans and a senescent murine model. J Clin Invest. 1995 May;95(5):2281-90. | 11. Ogawa-Goto K, Funamoto N, Abe T, Nagashima K: Different ceramide compositions of gangliosides between human motor and sensory nerves. J Neurochem. 1990 Nov;55(5):1486-93. | 12. Cho Y, Lew BL, Seong K, Kim NI: An inverse relationship between ceramide synthesis and clinical severity in patients with psoriasis. J Korean Med Sci. 2004 Dec;19(6):859-63. | 13. Bouwstra JA, Honeywell-Nguyen PL, Gooris GS, Ponec M: Structure of the skin barrier and its modulation by vesicular formulations. Prog Lipid Res. 2003 Jan;42(1):1-36. | 14. Uchida Y, Behne M, Quiec D, Elias PM, Holleran WM: Vitamin C stimulates sphingolipid production and markers of barrier formation in submerged human keratinocyte cultures. J Invest Dermatol. 2001 Nov;117(5):1307-13. | 15. Petrache I, Natarajan V, Zhen L, Medler TR, Richter AT, Cho C, Hubbard WC, Berdyshev EV, Tuder RM: Ceramide upregulation causes pulmonary cell apoptosis and emphysema-like disease in mice. Nat Med. 2005 May;11(5):491-8. Epub 2005 Apr 24. | 16. Demarchi F, Bertoli C, Greer PA, Schneider C: Ceramide triggers an NF-kappaB-dependent survival pathway through calpain. Cell Death Differ. 2005 May;12(5):512-22. | 17. Schafer A, Harzer K, Kattner E, Schafer HJ, Stoltenburg G, Lietz H: [Disseminated lipogranulomatosis (Farber disease) with hydrops fetalis]. Pathologe. 1996 Mar;17(2):145-9. | 18. Pettus BJ, Baes M, Busman M, Hannun YA, Van Veldhoven PP: Mass spectrometric analysis of ceramide perturbations in brain and fibroblasts of mice and human patients with peroxisomal disorders. Rapid Commun Mass Spectrom. 2004;18(14):1569-74. | 19. Okamoto R, Arikawa J, Ishibashi M, Kawashima M, Takagi Y, Imokawa G: Sphingosylphosphorylcholine is upregulated in the stratum corneum of patients with atopic dermatitis. J Lipid Res. 2003 Jan;44(1):93-102. | 20. Lew BL, Cho Y, Kim J, Sim WY, Kim NI: Ceramides and cell signaling molecules in psoriatic epidermis: reduced levels of ceramides, PKC-alpha, and JNK. J Korean Med Sci. 2006 Feb;21(1):95-9. | 21. van Lijnschoten G, Groener JE, Maas SM, Ben-Yoseph Y, Dingemans KP, Offerhaus GJ: Intrauterine fetal death due to Farber disease: case report. Pediatr Dev Pathol. 2000 Nov-Dec;3(6):597-602. | 22. Jana A, Pahan K: Human immunodeficiency virus type 1 gp120 induces apoptosis in human primary neurons through redox-regulated activation of neutral sphingomyelinase. J Neurosci. 2004 Oct 27;24(43):9531-40. | 23. Klein J: Functions and pathophysiological roles of phospholipase D in the brain. J Neurochem. 2005 Sep;94(6):1473-87. Epub 2005 Jul 22. | 24. Yatomi Y, Yamamura S, Hisano N, Nakahara K, Igarashi Y, Ozaki Y: Sphingosine 1-phosphate breakdown in platelets. J Biochem. 2004 Oct;136(4):495-502. | 25. Grether-Beck S, Bonizzi G, Schmitt-Brenden H, Felsner I, Timmer A, Sies H, Johnson JP, Piette J, Krutmann J: Non-enzymatic triggering of the ceramide signalling cascade by solar UVA radiation. EMBO J. 2000 Nov 1;19(21):5793-800. | 26. Ogawa-Goto K, Ohta Y, Kubota K, Funamoto N, Abe T, Taki T, Nagashima K: Glycosphingolipids of human peripheral nervous system myelins isolated from cauda equina. J Neurochem. 1993 Oct;61(4):1398-403. | 27. Satoi H, Tomimoto H, Ohtani R, Kitano T, Kondo T, Watanabe M, Oka N, Akiguchi I, Furuya S, Hirabayashi Y, Okazaki T: Astroglial expression of ceramide in Alzheimer's disease brains: a role during neuronal apoptosis. Neuroscience. 2005;130(3):657-66. | 28. Garcia-Ruiz C, Mari M, Morales A, Colell A, Ardite E, Fernandez-Checa JC: Human placenta sphingomyelinase, an exogenous acidic pH-optimum sphingomyelinase, induces oxidative stress, glutathione depletion, and apoptosis in rat hepatocytes. Hepatology. 2000 Jul;32(1):56-65. | 29. Gill JS, Windebank AJ: Suramin induced ceramide accumulation leads to apoptotic cell death in dorsal root ganglion neurons. Cell Death Differ. 1998 Oct;5(10):876-83. | 30. Both DM, Goodtzova K, Yarosh DB, Brown DA: Liposome-encapsulated ursolic acid increases ceramides and collagen in human skin cells. Arch Dermatol Res. 2002 Jan;293(11):569-75. | 31. Yarosh DB, Both D, Brown D: Liposomal ursolic acid (merotaine) increases ceramides and collagen in human skin. Horm Res. 2000;54(5-6):318-21. | 32. Dunn HG, Dolman CL, Farrell DF, Tischler B, Hasinoff C, Woolf LI: Krabbe's leukodystrophy without globoid cells. Neurology. 1976 Nov;26(11):1035-41. | 33. Persaud-Sawin DA, Boustany RM: Cell death pathways in juvenile Batten disease. Apoptosis. 2005 Oct;10(5):973-85. | 34. Di Marzio L, Cinque B, De Simone C, Cifone MG: Effect of the lactic acid bacterium Streptococcus thermophilus on ceramide levels in human keratinocytes in vitro and stratum corneum in vivo. J Invest Dermatol. 1999 Jul;113(1):98-106. | 35. Kirby RJ, Zheng S, Tso P, Howles PN, Hui DY: Bile salt-stimulated carboxyl ester lipase influences lipoprotein assembly and secretion in intestine: a process mediated via ceramide hydrolysis. J Biol Chem. 2002 Feb 8;277(6):4104-9. Epub 2001 Dec 3. | 36. Tanno O, Ota Y, Kitamura N, Katsube T, Inoue S: Nicotinamide increases biosynthesis of ceramides as well as other stratum corneum lipids to improve the epidermal permeability barrier. Br J Dermatol. 2000 Sep;143(3):524-31. | 37. Malagarie-Cazenave S, Segui B, Leveque S, Garcia V, Carpentier S, Altie MF, Brouchet A, Gouaze V, Andrieu-Abadie N, Barreira Y, Benoist H, Levade T: Role of FAN in tumor necrosis factor-alpha and lipopolysaccharide-induced interleukin-6 secretion and lethality in D-galactosamine-sensitized mice. J Biol Chem. 2004 Apr 30;279(18):18648-55. Epub 2004 Feb 25. | 38. Farina F, Cappello F, Todaro M, Bucchieri F, Peri G, Zummo G, Stassi G: Involvement of caspase-3 and GD3 ganglioside in ceramide-induced apoptosis in Farber disease. J Histochem Cytochem. 2000 Jan;48(1):57-62. | 39. Sugiki H, Hozumi Y, Maeshima H, Katagata Y, Mitsuhashi Y, Kondo S: C2-ceramide induces apoptosis in a human squamous cell carcinoma cell line. Br J Dermatol. 2000 Dec;143(6):1154-63. | 40. Chavez JA, Holland WL, Bar J, Sandhoff K, Summers SA: Acid ceramidase overexpression prevents the inhibitory effects of saturated fatty acids on insulin signaling. J Biol Chem. 2005 May 20;280(20):20148-53. Epub 2005 Mar 17. | 41. Saito M, Saito M, Cooper TB, Vadasz C: Ethanol-induced changes in the content of triglycerides, ceramides, and glucosylceramides in cultured neurons. Alcohol Clin Exp Res. 2005 Aug;29(8):1374-83. | 42. Maurer BJ, Melton L, Billups C, Cabot MC, Reynolds CP: Synergistic cytotoxicity in solid tumor cell lines between N-(4-hydroxyphenyl)retinamide and modulators of ceramide metabolism. J Natl Cancer Inst. 2000 Dec 6;92(23):1897-909. | 43. Lee HK, Nam GW, Kim SH, Lee SH: Phytocomponents of triterpenoids, oleanolic acid and ursolic acid, regulated differently the processing of epidermal keratinocytes via PPAR-alpha pathway. Exp Dermatol. 2006 Jan;15(1):66-73. | 44. Di Marzio L, Centi C, Cinque B, Masci S, Giuliani M, Arcieri A, Zicari L, De Simone C, Cifone MG: Effect of the lactic acid bacterium Streptococcus thermophilus on stratum corneum ceramide levels and signs and symptoms of atopic dermatitis patients. Exp Dermatol. 2003 Oct;12(5):615-20. | 45. Sando GN, Howard EJ, Madison KC: Induction of ceramide glucosyltransferase activity in cultured human keratinocytes. Correlation with culture differentiation. J Biol Chem. 1996 Sep 6;271(36):22044-51. | 46. Helge JW, Dobrzyn A, Saltin B, Gorski J: Exercise and training effects on ceramide metabolism in human skeletal muscle. Exp Physiol. 2004 Jan;89(1):119-27. | 47. Bektas M, Orfanos CE, Geilen CC: Different vitamin D analogues induce sphingomyelin hydrolysis and apoptosis in the human keratinocyte cell line HaCaT. Cell Mol Biol (Noisy-le-grand). 2000 Feb;46(1):111-9. | 48. Guchhait P, Lopez JA, Thiagarajan P: Characterization of autoantibodies against sulfatide from a V-gene phage-display library derived from patients with systemic lupus erythematosus. J Immunol Methods. 2004 Dec;295(1-2):129-37. Epub 2004 Oct 26. | 49. Erdreich-Epstein A, Tran LB, Cox OT, Huang EY, Laug WE, Shimada H, Millard M: Endothelial apoptosis induced by inhibition of integrins alphavbeta3 and alphavbeta5 involves ceramide metabolic pathways. Blood. 2005 Jun 1;105(11):4353-61. Epub 2005 Feb 10. | 50. Herr I, Martin-Villalba A, Kurz E, Roncaioli P, Schenkel J, Cifone MG, Debatin KM: FK506 prevents stroke-induced generation of ceramide and apoptosis signaling. Brain Res. 1999 May 1;826(2):210-9. | 51. Futerman AH: The roles of ceramide in the regulation of neuronal growth and development. Biochemistry (Mosc). 1998 Jan;63(1):74-83. | 52. Vielhaber G, Pfeiffer S, Brade L, Lindner B, Goldmann T, Vollmer E, Hintze U, Wittern KP, Wepf R: Localization of ceramide and glucosylceramide in human epidermis by immunogold electron microscopy. J Invest Dermatol. 2001 Nov;117(5):1126-36. | 53. Tojo K, Oota M, Honda H, Shibasaki T, Sakai O: Possible thyroidal involvement in a case of Fabry disease. Intern Med. 1994 Mar;33(3):172-6. | 54. Bowser PA, Gray GM: Sphingomyelinase in pig and human epidermis. J Invest Dermatol. 1978 Jun;70(6):331-5. | 55. 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. |
|
---|