beta-D-glucosyl-N-(dodecanoyl)sphingosine
PubChem CID: 20057354
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| Compound Synonyms | beta-D-glucosyl-N-(dodecanoyl)sphingosine, N-[(E,2S,3R)-3-hydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadec-4-en-2-yl]dodecanamide, C12 beta-GlcCer, beta-GlcCer (C12), D-glucosyl--1,1' N-lauroyl-D-erythro-sphingosine, beta-GlcCer (C12:0), C12-beta-glucosyl ceramide, CHEBI:76297, beta-D-glucosyl-N-dodecanoylsphing-4E-enine, 1-O-beta-D-glucopyranosyl-N-(dodecanoyl)sphingosine, Q27145864, N-[(2S,3S,4E)-1-(beta-D-glucopyranosyloxy)-3-hydroxyoctadec-4-en-2-yl]dodecanamide |
|---|---|
| Topological Polar Surface Area | 149.0 |
| Hydrogen Bond Donor Count | 6.0 |
| Heavy Atom Count | 45.0 |
| Description | A glycosphingolipid (ceramide and oligosaccharide)or oligoglycosylceramide with one or more sialic acids (i.e. n-acetylneuraminic acid) linked on the sugar chain. It is a component the cell plasma membrane which modulates cell signal transduction events. Gangliosides have been found to be highly important in immunology. Ganglioside GL1a carries a net-negative charge at pH 7.0 and is acidic. Gangliosides can amount to 6% of the weight of lipids from brain, but they are found at low levels in all animal tissues. Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease. [HMDB] |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 723.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;pubchem |
| Defined Atom Stereocenter Count | 7.0 |
| Enzyme Uniprot Id | P54803, P09848, Q9Y2B2, P17405, P16278, Q16739, Q9BRB3, P37287, Q14442, P57054, Q92535, Q13510, Q9Y5P4, P17900, P04062, P15812, P61916, P27544, P15813, Q9H3S5, Q7Z7B1, Q8TBF5, Q86VD9, Q9BYG0, Q9Y2C3, Q92521, Q07326, Q5H8A4, O95427, Q8TEQ8, Q96S52, Q969N2, Q9H490, Q9NUD9, Q3MUY2, P0C7U2, Q5QJU3, Q9NR71, Q9HCG7, Q8TDN7, Q92643 |
| Uniprot Id | P54803, P09848, Q8N5D6, Q9Y2B2, P17405, P16278, Q16739, Q9BRB3, P37287, Q14442, P57054, Q92535, Q13510, Q6UWV6, O60906, Q9Y5P4, P17900, P04062, Q13131, P15812, P61916, P27544, P15813, Q9H3S5, Q7Z7B1, Q8TBF5, Q86VD9, Q9BYG0, Q9NY59, Q9Y2C3, Q9UBX8, Q92521, Q07326, Q5H8A4, O95427, Q8TEQ8, Q96S52, Q969N2, Q9H490, Q9NUD9, Q3MUY2, Q96JA3, Q9NXE4, P0C7U2, Q5QJU3, Q9NR71, Q9HCG7, Q8TDN7, Q12918, Q8N5B7, Q8IZY2, Q92643, O43292, O95397, A6NH11, B5MDU3, P06126, Q5TA50, P29017, P18428, Q9UFH6, P29016, Q9NZD2 |
| Iupac Name | N-[(E,2S,3R)-3-hydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadec-4-en-2-yl]dodecanamide |
| Prediction Hob | 0.0 |
| Class | Sphingolipids |
| Xlogp | 9.1 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Glycosphingolipids |
| Molecular Formula | C36H69NO8 |
| Prediction Swissadme | 0.0 |
| Inchi Key | IYCYEZLMOLRFAN-IUGLYQEMSA-N |
| Fcsp3 | 0.9166666666666666 |
| Logs | -3.025 |
| Rotatable Bond Count | 29.0 |
| State | Solid |
| Logd | 4.507 |
| Synonyms | 1-O-b-D-Glucopyranosyl-N-(dodecanoyl)sphingosine, 1-O-beta-D-Glucopyranosyl-N-(dodecanoyl)sphingosine, 1-O-β-D-glucopyranosyl-N-(dodecanoyl)sphingosine, b-GlcCer (C12:0), b-GlcCer (C12), beta-GlcCer (C12:0), beta-GlcCer (C12), C12 b-GlcCer, C12 beta-GlcCer, C12 β-glccer, C12-b-Glucosyl ceramide, C12-beta-Glucosyl ceramide, C12-β-glucosyl ceramide, Glucosylceramide, β-glccer (C12:0), β-glccer (C12), beta-D-Glucosyl-N-dodecanoylsphing-4E-enine, 1-O-Β-D-glucopyranosyl-N-(dodecanoyl)sphingosine, b-D-Glucosyl-N-dodecanoylsphing-4E-enine, Β-D-glucosyl-N-dodecanoylsphing-4E-enine, Β-glccer (C12), Β-glccer (C12:0), C12 Β-glccer, C12-Β-glucosyl ceramide, b-D-Glucosyl-N-(dodecanoyl)sphingosine, Β-D-glucosyl-N-(dodecanoyl)sphingosine, 1-O-b-D-Glucopyranosyl-ceramide, 1-O-beta-delta-Glucopyranosyl-ceramide, Ganglioside GL1a, Gaucher cerebroside, GLC-beta1->1'cer, GlcCeramide, Glucocerebroside |
| Compound Name | beta-D-glucosyl-N-(dodecanoyl)sphingosine |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 643.502 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 643.502 |
| Hydrogen Bond Acceptor Count | 8.0 |
| Molecular Weight | 643.9 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 7.0 |
| Total Bond Stereocenter Count | 1.0 |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Esol | -7.8656714 |
| Inchi | 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 |
| Smiles | CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)NC(=O)CCCCCCCCCCC)O |
| Nring | 1.0 |
| Defined Bond Stereocenter Count | 1.0 |
| Taxonomy Direct Parent | Glycosyl-N-acylsphingosines |
- 1. Outgoing r'ship
FOUND_INto/from Arisaema Amurense (Plant) Rel Props:Source_db:cmaup_ingredients - 2. Outgoing r'ship
FOUND_INto/from Arisaema Erubescens (Plant) Rel Props:Source_db:cmaup_ingredients - 3. Outgoing r'ship
FOUND_INto/from Arisaema Heterophyllum (Plant) Rel Props:Source_db:cmaup_ingredients - 4. Outgoing r'ship
FOUND_INto/from Pinellia Ternata (Plant) Rel Props:Source_db:cmaup_ingredients