| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-11 16:46:52 UTC |
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| Updated at | 2022-05-11 16:46:52 UTC |
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| NP-MRD ID | NP0087335 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Glucosylceramide (d18:1/26:0) |
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| Description | GlcCer(d18:1/26:0), Also known as beta-glucosylceramide or beta-glccer, 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 (d18:1/26:0) was first documented in 1984 (PMID: 6423755). GlcCer(d18:1/26:0) Is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 12606053) (PMID: 3289655) (PMID: 3752966) (PMID: 3364161). |
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| Structure | CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCC InChI=1S/C50H97NO8/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/h37,39,43-45,47-50,52-53,55-57H,3-36,38,40-42H2,1-2H3,(H,51,54)/b39-37+/t43-,44+,45+,47+,48-,49+,50+/m0/s1 |
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| Synonyms | | Value | Source |
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| beta-D-Glucopyranosyl-N-(hexacosanoyl)sphingosine | ChEBI | | beta-D-Glucosyl-N-docosanoylsphingosine | ChEBI | | beta-GlcCer | ChEBI | | beta-Glucosylceramide | ChEBI | | Glucosylceramide (D18:1/26:0) | ChEBI | | N-(Hexacosanoyl)-1-beta-glucosyl-sphing-4-enine | ChEBI | | b-D-Glucopyranosyl-N-(hexacosanoyl)sphingosine | Generator | | Β-D-glucopyranosyl-N-(hexacosanoyl)sphingosine | Generator | | b-D-Glucosyl-N-docosanoylsphingosine | Generator | | Β-D-glucosyl-N-docosanoylsphingosine | Generator | | b-GlcCer | Generator | | Β-glccer | Generator | | b-Glucosylceramide | Generator | | Β-glucosylceramide | Generator | | N-(Hexacosanoyl)-1-b-glucosyl-sphing-4-enine | Generator | | N-(Hexacosanoyl)-1-β-glucosyl-sphing-4-enine | Generator | | b-D-Glucosyl-N-(hexacosanoyl)sphingosine | HMDB | | Β-D-glucosyl-N-(hexacosanoyl)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 | | Glucosylceramide(D18:1/26:0) | MetBuilder | | N-(Hexacosanoyl)-1-β-glucosyl-sphingosine | MetBuilder | | N-(Hexacosanoyl)-1-β-glucosyl-D-erythro-sphingosine | MetBuilder | | N-(Hexacosanoyl)-1-β-glucosyl-4-sphingenine | MetBuilder | | N-(Hexacosanoyl)-1-β-glucosyl-D-sphingosine | MetBuilder | | N-(Hexacosanoyl)-1-β-glucosyl-sphingenine | MetBuilder | | N-(Hexacosanoyl)-1-β-glucosyl-erythro-4-sphingenine | MetBuilder |
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| Chemical Formula | C50H97NO8 |
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| Average Mass | 840.3071 Da |
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| Monoisotopic Mass | 839.72142 Da |
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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]hexacosanamide |
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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]hexacosanamide |
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| CAS Registry Number | Not Available |
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| SMILES | CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCC |
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| InChI Identifier | InChI=1S/C50H97NO8/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/h37,39,43-45,47-50,52-53,55-57H,3-36,38,40-42H2,1-2H3,(H,51,54)/b39-37+/t43-,44+,45+,47+,48-,49+,50+/m0/s1 |
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| InChI Key | DOIOUJPHIXRQFM-WBOUPBNQSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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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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| Physical Properties |
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| State | Not Available |
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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 | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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