Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 06:42:21 UTC |
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Update Date | 2016-11-09 01:21:23 UTC |
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Accession Number | CHEM035827 |
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Identification |
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Common Name | Glucosylceramide (d18:1/12:0) |
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Class | Small Molecule |
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Description | A D-glucosyl-N-acylsphingosine in which the ceramide N-acyl group is dodecanoyl. |
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Contaminant Sources | |
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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1-O-beta-D-Glucopyranosyl-N-(dodecanoyl)sphingosine | ChEBI | beta-D-Glucosyl-N-dodecanoylsphing-4E-enine | ChEBI | beta-GlcCer (C12) | ChEBI | beta-GlcCer (C12:0) | ChEBI | C12 beta-GlcCer | ChEBI | C12-beta-Glucosyl ceramide | ChEBI | 1-O-b-D-Glucopyranosyl-N-(dodecanoyl)sphingosine | Generator | 1-O-Β-D-glucopyranosyl-N-(dodecanoyl)sphingosine | Generator | b-D-Glucosyl-N-dodecanoylsphing-4E-enine | Generator | Β-D-glucosyl-N-dodecanoylsphing-4E-enine | Generator | b-GlcCer (C12) | Generator | Β-glccer (C12) | Generator | b-GlcCer (C12:0) | Generator | Β-glccer (C12:0) | Generator | C12 b-GlcCer | Generator | C12 Β-glccer | Generator | C12-b-Glucosyl ceramide | Generator | C12-Β-glucosyl ceramide | Generator | b-D-Glucosyl-N-(dodecanoyl)sphingosine | HMDB | Β-D-glucosyl-N-(dodecanoyl)sphingosine | HMDB | 1-O-b-D-Glucopyranosyl-ceramide | HMDB | 1-O-beta-delta-Glucopyranosyl-ceramide | HMDB | Ganglioside GL1a | HMDB | Gaucher cerebroside | HMDB | GLC-beta1->1'cer | HMDB | GlcCeramide | HMDB | Glucocerebroside | HMDB | Glucosylceramide | HMDB |
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Chemical Formula | C36H69NO8 |
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Average Molecular Mass | 643.935 g/mol |
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Monoisotopic Mass | 643.502 g/mol |
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CAS Registry Number | Not Available |
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IUPAC Name | N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]dodecanamide |
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Traditional Name | N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]dodecanamide |
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SMILES | CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC |
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InChI Identifier | InChI=1S/C36H69NO8/c1-3-5-7-9-11-13-14-15-16-18-19-21-23-25-30(39)29(28-44-36-35(43)34(42)33(41)31(27-38)45-36)37-32(40)26-24-22-20-17-12-10-8-6-4-2/h23,25,29-31,33-36,38-39,41-43H,3-22,24,26-28H2,1-2H3,(H,37,40)/b25-23+/t29-,30+,31+,33+,34-,35+,36+/m0/s1 |
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InChI Key | IYCYEZLMOLRFAN-IUGLYQEMSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety. |
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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 | Glycosphingolipids |
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Direct Parent | Glycosyl-N-acylsphingosines |
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Alternative Parents | |
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Substituents | - Glycosyl-n-acylsphingosine
- Fatty acyl glycoside
- Fatty acyl glycoside of mono- or disaccharide
- Alkyl glycoside
- Hexose monosaccharide
- Glycosyl compound
- O-glycosyl compound
- Fatty amide
- Fatty acyl
- Monosaccharide
- N-acyl-amine
- Oxane
- Carboxamide group
- Secondary carboxylic acid amide
- Secondary alcohol
- Acetal
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Alcohol
- Organic oxygen compound
- Organic nitrogen compound
- Primary alcohol
- Carbonyl group
- Organooxygen compound
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0000009000-73ad3734d340dbe8da71 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-5200359000-c9a259147d1d08aec73d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0536-8490310000-3be3d89c4510e266eac9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-3100509000-718041c2ea7044038c59 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03fv-4200936000-2ec404cd171c2c95c023 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9100200000-67b21ea07363eca8b255 | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0004969 |
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FooDB ID | FDB023556 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | GLUCOSYL_CERAMIDE |
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METLIN ID | 7222 |
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PDB ID | Not Available |
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Wikipedia Link | Not Available |
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Chemspider ID | 16744954 |
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ChEBI ID | 76297 |
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PubChem Compound ID | 20057354 |
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Kegg Compound ID | C01190 |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24076636 | 2. Hara A, Kitazawa N, Taketomi T: Abnormalities of glycosphingolipids in mucopolysaccharidosis type III B. J Lipid Res. 1984 Feb;25(2):175-84. | 3. Beutler E: Gaucher disease. Blood Rev. 1988 Mar;2(1):59-70. | 4. Kaye EM, Ullman MD, Wilson ER, Barranger JA: Type 2 and type 3 Gaucher disease: a morphological and biochemical study. Ann Neurol. 1986 Aug;20(2):223-30. | 5. Conradi NG, Kalimo H, Sourander P: Reactions of vessel walls and brain parenchyma to the accumulation of Gaucher cells in the Norrbottnian type (type III) of Gaucher disease. Acta Neuropathol. 1988;75(4):385-90. | 6. Smith RL, Hutchins GM, Sack GH Jr, Ridolfi RL: Unusual cardiac, renal and pulmonary involvement in Gaucher's disease. Intersitial glucocerebroside accumulation, pulmonary hypertension and fatal bone marrow embolization. Am J Med. 1978 Aug;65(2):352-60. | 7. Ohashi T: [Gene therapy for Gaucher disease]. Nihon Rinsho. 1995 Dec;53(12):3089-94. | 8. Nishimura RN, Barranger JA: Neurologic complications of Gaucher's disease, type 3. Arch Neurol. 1980 Feb;37(2):92-3. | 9. Eto Y, Ida H: [Molecular studies of Gaucher disease]. Rinsho Byori. 1996 Apr;44(4):327-34. | 10. Naito M, Takahashi K, Hojo H: An ultrastructural and experimental study on the development of tubular structures in the lysosomes of Gaucher cells. Lab Invest. 1988 May;58(5):590-8. | 11. Mariani G, Filocamo M, Giona F, Villa G, Amendola A, Erba P, Buffoni F, Copello F, Pierini A, Minichilli F, Gatti R, Brady RO: Severity of bone marrow involvement in patients with Gaucher's disease evaluated by scintigraphy with 99mTc-sestamibi. J Nucl Med. 2003 Aug;44(8):1253-62. | 12. Soffer D, Yamanaka T, Wenger DA, Suzuki K, Suzuki K: Central nervous system involvement in adult-onset Gaucher's disease. Acta Neuropathol. 1980;49(1):1-6. | 13. Ohashi T: [Gaucher disease]. Nihon Rinsho. 1995 Dec;53(12):2943-6. | 14. Starzl TE, Demetris AJ, Trucco M, Ricordi C, Ildstad S, Terasaki PI, Murase N, Kendall RS, Kocova M, Rudert WA, et al.: Chimerism after liver transplantation for type IV glycogen storage disease and type 1 Gaucher's disease. N Engl J Med. 1993 Mar 18;328(11):745-9. | 15. Pilz H, Heipertz R: [Differential diagnosis of congenital lipidoses by lipid analyses of body fluids, biopsy and autopsy tissue]. Fortschr Neurol Psychiatr Grenzgeb. 1975 Nov;43(11):602-17. | 16. Nilsson O, Grabowski GA, Ludman MD, Desnick RJ, Svennerholm L: Glycosphingolipid studies of visceral tissues and brain from type 1 Gaucher disease variants. Clin Genet. 1985 May;27(5):443-50. | 17. Harzer K, Massenkeil G, Frohlich E: Concurrent increase of cholesterol, sphingomyelin and glucosylceramide in the spleen from non-neurologic Niemann-Pick type C patients but also patients possibly affected with other lipid trafficking disorders. FEBS Lett. 2003 Feb 27;537(1-3):177-81. | 18. Dawson G, Kruski AW, Scanu AM: Distribution of glycosphingolipids in the serum lipoproteins of normal human subjects and patients with hypo- and hyperlipidemias. J Lipid Res. 1976 Mar;17(2):125-31. | 19. Adar T, Ben-Ami R, Elstein D, Zimran A, Berliner S, Yedgar S, Barshtein G: Aggregation of red blood cells in patients with Gaucher disease. Br J Haematol. 2006 Aug;134(4):432-7. Epub 2006 Jul 10. | 20. Dolen EG, Berdon WE, Ruzal-Shapiro C: "Cold bone scans" as a sign of hemorrhagic infarcts of the spine in Gaucher's disease. Pediatr Radiol. 1997 Jun;27(6):514-6. | 21. Daniels LB, Coyle PJ, Glew RH, Radin NS, Labow RS: Brain glucocerebrosidase in Gaucher's disease. Arch Neurol. 1982 Sep;39(9):550-6. | 22. Stirnemann J, Belmatoug N: [Adult Gaucher disease]. Rev Med Interne. 2001 Dec;22 Suppl 3:374s-383s. | 23. Erickson JS, Radin NS: N-hexyl-O-glucosyl sphingosine, an inhibitor of glucosyl ceramide -glucosidase. J Lipid Res. 1973 Mar;14(2):133-7. | 24. Deguchi H, Bouma BN, Middeldorp S, Lee YM, Griffin JH: Decreased plasma sensitivity to activated protein C by oral contraceptives is associated with decreases in plasma glucosylceramide. J Thromb Haemost. 2005 May;3(5):935-8. | 25. Shoenfeld Y, Gallant LA, Shaklai M, Livni E, Djaldetti M, Pinkhas J: Gaucher's disease: a disease with chronic stimulation of the immune system. Arch Pathol Lab Med. 1982 Aug;106(8):388-91. | 26. Ringden O, Groth CG, Erikson A, Granqvist S, Mansson JE, Sparrelid E: Ten years' experience of bone marrow transplantation for Gaucher disease. Transplantation. 1995 Mar 27;59(6):864-70. | 27. Nilsson O, Mansson JE, Hakansson G, Svennerholm L: The occurrence of psychosine and other glycolipids in spleen and liver from the three major types of Gaucher's disease. Biochim Biophys Acta. 1982 Sep 14;712(3):453-63. | 28. Dann K, Althaus C, Kersten A, vom Dahl S, Sundmacher R: [Uveitis masquerade syndrome in Gaucher disease. Causal treatment by alglucerase substitution therapy]. Klin Monbl Augenheilkd. 1998 Dec;213(6):358-61. | 29. Conradi NG, Sourander P, Nilsson O, Svennerholm L, Erikson A: Neuropathology of the Norrbottnian type of Gaucher disease. Morphological and biochemical studies. Acta Neuropathol. 1984;65(2):99-109. | 30. Beutler E: Gaucher disease: new molecular approaches to diagnosis and treatment. Science. 1992 May 8;256(5058):794-9. | 31. Owada M, Sakiyama T, Kitagawa T: Neuropathic Gaucher's disease with normal 4-methylumbelliferyl-beta-glucosidase activity in the liver. Pediatr Res. 1977 May;11(5):641-6. | 32. Nilsson O, Svennerholm L: Accumulation of glucosylceramide and glucosylsphingosine (psychosine) in cerebrum and cerebellum in infantile and juvenile Gaucher disease. J Neurochem. 1982 Sep;39(3):709-18. | 33. Liu Y, Suzuki K, Reed JD, Grinberg A, Westphal H, Hoffmann A, Doring T, Sandhoff K, Proia RL: Mice with type 2 and 3 Gaucher disease point mutations generated by a single insertion mutagenesis procedure. Proc Natl Acad Sci U S A. 1998 Mar 3;95(5):2503-8. | 34. Poll LW, Maas M, Terk MR, Roca-Espiau M, Bembi B, Ciana G, Weinreb NJ: Response of Gaucher bone disease to enzyme replacement therapy. Br J Radiol. 2002;75 Suppl 1:A25-36. | 35. Campbell PE, Harris CM, Harris CM, Sirimanna T, Vellodi A: A model of neuronopathic Gaucher disease. J Inherit Metab Dis. 2003;26(7):629-39. | 36. Schaison G, Caubel I, Belmatoug N, Billette de Villemeur T, Saudubray JM: [French results of enzyme replacement therapy in Gaucher's disease]. Bull Acad Natl Med. 2002;186(5):851-61; discussion 861-3. | 37. Hollak CE, Boot RG, Poorthuis BJ, Aerts JM: [From gene to disease; Gaucher disease]. Ned Tijdschr Geneeskd. 2005 Sep 24;149(39):2163-6. |
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