Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:30:24 UTC |
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Update date | 2017-03-11 23:00:23 UTC |
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Primary ID | FDB023471 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Trihexosylceramide (d18:1/9Z-18:1) |
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Description | Trihexosylceramide is a glycosphingolipid which contains a trisaccharide (galactose-galactose-glucose) moiety bound in glycosidic linkage to the hydroxyl group of ceramide as the polar head group. It accumulates in tissue due to a defect in ceramide trihexosidase and is the cause of angiokeratoma corporis diffusum (Fabry disease).
Although normal human colonic epithelial cells lack the glycosphingolipid globotriaosylceramide (Gb(3)), this molecule is highly expressed in metastatic colon cancer (PubMed ID 16365318 ) [HMDB] |
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CAS Number | 71965-57-6 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C54H99NO18 |
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IUPAC name | (9E)-N-[(4E)-1-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3-hydroxyoctadec-4-en-2-yl]octadec-9-enamide |
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InChI Identifier | InChI=1S/C54H99NO18/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-42(60)55-37(38(59)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)36-68-52-48(66)45(63)50(40(34-57)70-52)73-54-49(67)46(64)51(41(35-58)71-54)72-53-47(65)44(62)43(61)39(33-56)69-53/h17-18,29,31,37-41,43-54,56-59,61-67H,3-16,19-28,30,32-36H2,1-2H3,(H,55,60)/b18-17+,31-29+ |
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InChI Key | XRPQSEBNLXORQZ-LSUSWXEESA-N |
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Isomeric SMILES | CCCCCCCCCCCCC\C=C\C(O)C(COC1OC(CO)C(OC2OC(CO)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C(O)C1O)NC(=O)CCCCCCC\C=C\CCCCCCCC |
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Average Molecular Weight | 1050.3598 |
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Monoisotopic Molecular Weight | 1049.686215369 |
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Classification |
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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
- Oligosaccharide
- Fatty acyl glycoside
- Alkyl glycoside
- Glycosyl compound
- O-glycosyl compound
- Fatty amide
- N-acyl-amine
- Oxane
- Fatty acyl
- Secondary alcohol
- Secondary carboxylic acid amide
- Carboxamide group
- Oxacycle
- Polyol
- Organoheterocyclic compound
- Carboxylic acid derivative
- Acetal
- Primary alcohol
- Alcohol
- Organopnictogen compound
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Carbonyl group
- Organooxygen compound
- Organic nitrogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Organoleptic effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Not Available |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0w5a-9512020120-f38032a68e62d23c1316 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0h61-3901020120-9e0b089f425ad828be7a | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-029x-5900020000-81d92690f9dde25b087b | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000120-30de7c5e8d79ca081640 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-9501000123-4db88328dcede6967ee7 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-073c-7934131640-237243ecb1e3030f0902 | 2021-09-25 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 16744891 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C04737 |
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Pubchem Compound ID | 20057314 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB04878 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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