Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 06:14:03 UTC |
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Update Date | 2016-11-09 01:21:22 UTC |
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Accession Number | CHEM035746 |
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Identification |
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Common Name | Lactosylceramide (d18:1/12:0) |
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Class | Small Molecule |
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Description | Lactosylceramide (d18:1/12:0) is a lactosylceramide or LacCer. Lactosylceramides are the most important and abundant of the diosylceramides. Lactosylceramides (LacCer) were originally called 'cytolipin H'. It is found in small amounts only in most animal tissues, but it has a number of significant biological functions and it is of great importance as the biosynthetic precursor of most of the neutral oligoglycosylceramides, sulfatides and gangliosides. In animal tissues, biosynthesis of lactosylceramide involves addition of the second monosaccharides unit (galactose) as its nucleotide derivative to monoglucosylceramide, catalysed by a specific beta-1,4-galactosyltransferase on the lumenal side of the Golgi apparatus. The glucosylceramide precursor must first cross from the cytosolic side of the membrane, possibly via the action of a flippase. The lactosylceramide produced can be further glycosylated or transferred to the plasma membrane. Lactosylceramide may assist in stabilizing the plasma membrane and activating receptor molecules in the special micro-domains or rafts, as with the cerebrosides. It may also have its own specialized function in the immunological system in that it is known to bind to specific bacteria. In addition, it is believed that a number of pro-inflammatory factors activate lactosylceramide synthase to generate lactosylceramide, which in turn activates "oxygen-sensitive" signalling pathways that affect such cellular processes as proliferation, adhesion, migration and angiogenesis. Dysfunctions in these pathways can affect several diseases of the cardiovascular system, cancer and inflammatory states, so lactosylceramide metabolism is a potential target for new therapeutic treatments. beta-D-Galactosyl-1,4-beta-D-glucosylceramide is the second to last step in the synthesis of N-Acylsphingosine and is converted
from Glucosylceramide via the enzyme beta-1,4-galactosyltransferase 6(EC:2.4.1.-). It can be converted to Glucosylceramide via the enzyme beta-galactosidase (EC:3.2.1.23). [HMDB] |
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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-(4-O-b-D-Galactopyranosyl-b-D-glucopyranosyl)-ceramide | HMDB | 1-O-(4-O-beta-D-Galactopyranosyl-beta-glucopyranosyl)ceramide | HMDB | 1-O-(4-O-beta-delta-Galactopyranosyl-beta-delta-glucopyranosyl)-ceramide | HMDB | 1-O-(4-O-beta-delta-Galactopyranosyl-beta-glucopyranosyl)ceramide | HMDB | 1Ylce-O-(4-O-beta-delta-galactopyranosyl-beta-glucopyranosyl)ceramide | HMDB | beta-D-Galactosyl-1,4-beta-D-glucosylceramide | HMDB | beta-delta-Galactosyl-1,4-beta-delta-glucosramide | HMDB | beta-delta-Galactosyl-1,4-beta-delta-glucosylceramide | HMDB | CDH | HMDB | CDW17 Antigen | HMDB | Cytolipin H | HMDB | D-Galactosyl-1,4-beta-D-glucosylceramide | HMDB | delta-Galactosyl-1,4-beta-delta-glucosylceramide | HMDB | Gal-beta1->4GLC-beta1->1'cer | HMDB | LacCer | HMDB | Lactosyl ceramide (D18:1/12:0) | HMDB | Lactosyl-N-acylsphingosine | HMDB | Lactosylceramide | HMDB | N-(Dodecanoyl)-1-b-lactosyl-sphing-4-enine | HMDB | N-(Dodecanoyl)-1-beta-lactosyl-sphing-4-enine | HMDB | N-Lignoceryl sphingosyl lactoside | HMDB | N-(Dodecanoyl)-1-β-lactosyl-sphing-4-enine | MetBuilder | Lactosylceramide(D18:1/12:0) | MetBuilder | N-(Dodecanoyl)-1-β-lactosyl-sphingosine | MetBuilder | N-(Dodecanoyl)-1-β-lactosyl-D-erythro-sphingosine | MetBuilder | N-(Dodecanoyl)-1-β-lactosyl-4-sphingenine | MetBuilder | N-(Dodecanoyl)-1-β-lactosyl-D-sphingosine | MetBuilder | N-(Dodecanoyl)-1-β-lactosyl-sphingenine | MetBuilder | N-(Dodecanoyl)-1-β-lactosyl-erythro-4-sphingenine | MetBuilder | LacCer(D18:1/12:0) | HMDB |
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Chemical Formula | C42H79NO13 |
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Average Molecular Mass | 806.076 g/mol |
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Monoisotopic Mass | 805.555 g/mol |
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CAS Registry Number | Not Available |
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IUPAC Name | N-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]dodecanamide |
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Traditional Name | N-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-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]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)C1O)NC(=O)CCCCCCCCCCC |
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InChI Identifier | InChI=1S/C42H79NO13/c1-3-5-7-9-11-13-14-15-16-18-19-21-23-25-31(46)30(43-34(47)26-24-22-20-17-12-10-8-6-4-2)29-53-41-39(52)37(50)40(33(28-45)55-41)56-42-38(51)36(49)35(48)32(27-44)54-42/h23,25,30-33,35-42,44-46,48-52H,3-22,24,26-29H2,1-2H3,(H,43,47)/b25-23+/t30-,31+,32+,33+,35-,36-,37+,38+,39?,40+,41+,42-/m0/s1 |
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InChI Key | KNWHKVBHCLQVFX-QXWNENIHSA-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
- Disaccharide
- Glycosyl compound
- O-glycosyl compound
- Fatty amide
- N-acyl-amine
- Oxane
- Fatty acyl
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Organoheterocyclic compound
- Polyol
- Oxacycle
- Carboxylic acid derivative
- Acetal
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Alcohol
- Organonitrogen compound
- Carbonyl group
- Organooxygen compound
- Primary alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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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 GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0550-0200309610-f6c301e7c9c570cf4fe7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01t9-0410609200-b7f26710a13afd5225ac | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-1920705300-3cd1c8617421be9f0342 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0ukl-1512409570-3d65cc4bae3641087992 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00dr-3703519300-898303877ac86d41dfad | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004l-4900302000-222d0bf59eaa278c1a4a | 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 | HMDB0004866 |
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FooDB ID | FDB023465 |
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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 | CYTOLIPIN_H |
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METLIN ID | 7123 |
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PDB ID | Not Available |
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Wikipedia Link | Not Available |
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Chemspider ID | 16744880 |
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ChEBI ID | 89446 |
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PubChem Compound ID | 20057304 |
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Kegg Compound ID | C01290 |
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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. Nicolaou, K. C.; Caulfield, T.; Kataoka, H.; Kumazawa, T. A practical and enantioselective synthesis of glycosphingolipids and related compounds. Total synthesis of globotriaosylceramide (Gb3). Journal of the American Chemical Society (1988), 110(23), 791 | 2. Moore RM, Silver RJ, Moore JJ: Physiological apoptotic agents have different effects upon human amnion epithelial and mesenchymal cells. Placenta. 2003 Feb-Mar;24(2-3):173-80. | 3. Stevens CR, Oberholzer VG, Walker-Smith JA, Phillips AD: Lactosylceramide in inflammatory bowel disease: a biochemical study. Gut. 1988 May;29(5):580-7. | 4. Prinetti A, Basso L, Appierto V, Villani MG, Valsecchi M, Loberto N, Prioni S, Chigorno V, Cavadini E, Formelli F, Sonnino S: Altered sphingolipid metabolism in N-(4-hydroxyphenyl)-retinamide-resistant A2780 human ovarian carcinoma cells. J Biol Chem. 2003 Feb 21;278(8):5574-83. Epub 2002 Dec 16. | 5. Furukawa K, Takamiya K, Furukawa K: Beta1,4-N-acetylgalactosaminyltransferase--GM2/GD2 synthase: a key enzyme to control the synthesis of brain-enriched complex gangliosides. Biochim Biophys Acta. 2002 Dec 19;1573(3):356-62. | 6. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. | 7. Choudhury A, Dominguez M, Puri V, Sharma DK, Narita K, Wheatley CL, Marks DL, Pagano RE: Rab proteins mediate Golgi transport of caveola-internalized glycosphingolipids and correct lipid trafficking in Niemann-Pick C cells. J Clin Invest. 2002 Jun;109(12):1541-50. | 8. Ledvinova J, Poupetova H, Hanackova A, Pisacka M, Elleder M: Blood group B glycosphingolipids in alpha-galactosidase deficiency (Fabry disease): influence of secretor status. Biochim Biophys Acta. 1997 Apr 1;1345(2):180-7. | 9. Hulkova H, Ledvinova J, Asfaw B, Koubek K, Kopriva K, Elleder M: Lactosylceramide in lysosomal storage disorders: a comparative immunohistochemical and biochemical study. Virchows Arch. 2005 Jul;447(1):31-44. Epub 2005 May 26. | 10. Komagome R, Sawa H, Suzuki T, Suzuki Y, Tanaka S, Atwood WJ, Nagashima K: Oligosaccharides as receptors for JC virus. J Virol. 2002 Dec;76(24):12992-3000. | 11. Tanaka H, Suzuki K: Lactosylceramidase assays for diagnosis of globoid cell leukodystrophy and GM1-gangliosidosis. Clin Chim Acta. 1977 Mar 1;75(2):267-74. | 12. Sharma DK, Brown JC, Cheng Z, Holicky EL, Marks DL, Pagano RE: The glycosphingolipid, lactosylceramide, regulates beta1-integrin clustering and endocytosis. Cancer Res. 2005 Sep 15;65(18):8233-41. | 13. Takizawa M, Nomura T, Wakisaka E, Yoshizuka N, Aoki J, Arai H, Inoue K, Hattori M, Matsuo N: cDNA cloning and expression of human lactosylceramide synthase. Biochim Biophys Acta. 1999 May 18;1438(2):301-4. | 14. Sala G, Dupre T, Seta N, Codogno P, Ghidoni R: Increased biosynthesis of glycosphingolipids in congenital disorder of glycosylation Ia (CDG-Ia) fibroblasts. Pediatr Res. 2002 Nov;52(5):645-51. |
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