| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:14:13 UTC |
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| Update Date | 2020-05-11 20:54:22 UTC |
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| BMDB ID | BMDB0004976 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Glucosylceramide (d18:1/26:1(17Z)) |
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| Description | Glucosylceramide (d18:1/26:1(17Z)), also known as C26:1 glccer or glccer(D18:1/26:1(17Z)), 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. Glucosylceramide (d18:1/26:1(17Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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| Structure | |
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| Synonyms | | Value | Source |
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| C26:1 GlcCer | ChEBI | | GlcCer(D18:1/26:1(17Z)) | ChEBI | | N-(17Z-Hexacosenoyl)-1-beta-glucosyl-sphing-4-enine | ChEBI | | N-(17Z-Hexacosenoyl)-1-b-glucosyl-sphing-4-enine | Generator | | N-(17Z-Hexacosenoyl)-1-β-glucosyl-sphing-4-enine | Generator | | b-D-Glucosyl-N-[(17Z)-hexacosenoyl]sphingosine | HMDB | | Β-D-glucosyl-N-[(17Z)-hexacosenoyl]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 | | GLC-beta1->1'cer(D18:1/26:1 | HMDB | | GlcCeramide | HMDB | | Glucocerebroside | HMDB | | Glucosylceramide | HMDB |
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| Chemical Formula | C50H95NO8 |
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| Average Molecular Weight | 838.2912 |
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| Monoisotopic Molecular Weight | 837.705769021 |
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| IUPAC Name | (17Z)-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]hexacos-17-enamide |
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| Traditional Name | (17Z)-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]hexacos-17-enamide |
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| CAS Registry Number | 85305-87-9 |
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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)CCCCCCCCCCCCCCC\C=C/CCCCCCCC |
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| InChI Identifier | InChI=1S/C50H95NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-46(54)51-43(42-58-50-49(57)48(56)47(55)45(41-52)59-50)44(53)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2/h17-18,37,39,43-45,47-50,52-53,55-57H,3-16,19-36,38,40-42H2,1-2H3,(H,51,54)/b18-17-,39-37+/t43-,44+,45+,47+,48-,49+,50+/m0/s1 |
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| InChI Key | LVROXDRMMJVBGH-WLPLOMEJSA-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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| Ontology |
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| Status | Expected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cell membrane
- Endosome
- Membrane
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Insoluble | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00dr-0102203090-abb2f14609f2d3313384 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4m-0223309230-b8cce9a560f904b858d7 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0035-1498204710-82c97eda4b44ed0aed3e | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-1300004090-6887acda90201d7212bb | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0403-5814349140-264b076d056596f4fc16 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9414001000-ebf0783174edd200782d | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05br-1001005190-acdd28f3d172dfb9ae7b | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4l-2101009340-64fe99861ac0b001d3de | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9500004000-54e7f7a9705476312fb7 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0000000090-cb2667c55d459b0f936a | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-6200103590-e78b709e889e3cc71965 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a7l-9412701000-29278b3475e07ff07ef6 | View in MoNA |
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