Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:08 UTC |
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HMDB ID | HMDB0001196 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N,N'-Diacetylchitobiosyldiphosphodolichol |
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Description | Diacetylchitobiosyldiphosphodolichol is an intermediate in the N-glycan biosynthesis, a series of reactions catalyzed by the enzymes chitobiosyldiphosphodolichol beta-mannosyltransferases (EC 2.4.1.141, EC 2.4.1.142). (KEGG). This compound and its corresponding enzymes are implicated in Congenital disorders of glycosylation (CDGs) , that comprise a group of multisystem diseases with mostly severe psychomotor and mental retardation. Type I CDG comprises those disorders in which there are defects that affect biosynthesis of dolichol-linked oligosaccharides in the cytosol or the endoplasmic reticulum (ER), as well as defects involving the transfer of oligosaccharides onto nascent glycoproteins. Type II CDG comprises all defects of further trimming and elongation of N-linked oligosaccharides in the ER and Golgi. (OMIM 608540 ). |
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Structure | OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(O)=O)[C@@H](O[C@@H]2CO)OP(=O)(O)OP(O)(=O)OCCC(C)CC\C=C(/C)CC=C(C)C)[C@H](NC(O)=O)[C@@H](O)[C@@H]1O InChI=1S/C28H50N2O19P2/c1-14(2)8-9-15(3)6-5-7-16(4)10-11-44-50(40,41)49-51(42,43)48-26-20(30-28(38)39)23(35)24(18(13-32)46-26)47-25-19(29-27(36)37)22(34)21(33)17(12-31)45-25/h6,8,16-26,29-35H,5,7,9-13H2,1-4H3,(H,36,37)(H,38,39)(H,40,41)(H,42,43)/b15-6+/t16?,17-,18-,19-,20-,21-,22-,23-,24-,25+,26+/m1/s1 |
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Synonyms | Value | Source |
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Chitobiosyldiphosphodolichol | HMDB | [(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-(carboxyamino)-4-hydroxy-6-{[hydroxy({[hydroxy({[(6E)-3,7,10-trimethylundeca-6,9-dien-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]carbamate | HMDB |
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Chemical Formula | C28H50N2O19P2 |
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Average Molecular Weight | 780.6461 |
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Monoisotopic Molecular Weight | 780.248300452 |
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IUPAC Name | [(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-(carboxyamino)-4-hydroxy-6-{[hydroxy({[hydroxy({[(6E)-3,7,10-trimethylundeca-6,9-dien-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]carbamic acid |
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Traditional Name | (2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-(carboxyamino)-4-hydroxy-6-{[hydroxy({hydroxy[(6E)-3,7,10-trimethylundeca-6,9-dien-1-yl]oxyphosphoryl}oxy)phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-ylcarbamic acid |
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CAS Registry Number | Not Available |
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SMILES | OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(O)=O)[C@@H](O[C@@H]2CO)OP(=O)(O)OP(O)(=O)OCCC(C)CC\C=C(/C)CC=C(C)C)[C@H](NC(O)=O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C28H50N2O19P2/c1-14(2)8-9-15(3)6-5-7-16(4)10-11-44-50(40,41)49-51(42,43)48-26-20(30-28(38)39)23(35)24(18(13-32)46-26)47-25-19(29-27(36)37)22(34)21(33)17(12-31)45-25/h6,8,16-26,29-35H,5,7,9-13H2,1-4H3,(H,36,37)(H,38,39)(H,40,41)(H,42,43)/b15-6+/t16?,17-,18-,19-,20-,21-,22-,23-,24-,25+,26+/m1/s1 |
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InChI Key | YBYNXPYEWMVKMB-HNLAPQKRSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as disaccharide phosphates. These are disaccharides carrying one or more phosphate group on a sugar unit. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Disaccharide phosphates |
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Alternative Parents | |
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Substituents | - Disaccharide phosphate
- Glycosyl compound
- O-glycosyl compound
- Monocyclic monoterpenoid
- Monoterpenoid
- Organic pyrophosphate
- Monoalkyl phosphate
- Alkyl phosphate
- Phosphoric acid ester
- Oxane
- Organic phosphoric acid derivative
- Secondary alcohol
- Carbamic acid
- Carbonic acid derivative
- Carbamic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Acetal
- Hydrocarbon derivative
- Alcohol
- Organopnictogen compound
- Organic nitrogen compound
- Carbonyl group
- Organic oxide
- Organonitrogen 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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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0kib-2635051900-244e3b9848fc8432a321 | 2017-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TMS_1_5) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TMS_1_6) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TMS_1_7) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TMS_1_8) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TMS_1_9) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TMS_1_10) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TMS_1_11) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TBDMS_1_4) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TBDMS_1_5) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TBDMS_1_6) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TBDMS_1_7) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TBDMS_1_8) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TBDMS_1_9) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TBDMS_1_10) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol GC-MS (TBDMS_1_11) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol 10V, Positive-QTOF | splash10-029f-0301010900-83c5f092c20bb9fc1fe2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol 20V, Positive-QTOF | splash10-0006-1911120200-4b83c57a91436ddfc8c4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol 40V, Positive-QTOF | splash10-00kf-2901012400-5d49124eb1cbb704d66c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol 10V, Negative-QTOF | splash10-00mo-1193001100-37bbf93a2f9fca829143 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol 20V, Negative-QTOF | splash10-03di-9426281500-1dc3c430f2aa0cfe74de | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol 40V, Negative-QTOF | splash10-0r2c-5923200000-18fcf041af6f188c6e07 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol 10V, Positive-QTOF | splash10-001r-0010001900-5a7af0115dce2e08aeb1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol 20V, Positive-QTOF | splash10-05rc-9000021600-c1d22d443ae9092b28e5 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol 40V, Positive-QTOF | splash10-002f-9210110000-f54019f09b686230fdeb | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol 10V, Negative-QTOF | splash10-01t9-0000010900-be8f42ec18f6c9ca45ea | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol 20V, Negative-QTOF | splash10-00kr-2200069800-1520b2a884ac541a95b7 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N'-Diacetylchitobiosyldiphosphodolichol 40V, Negative-QTOF | splash10-0kdi-9314020000-9f37a4cf90400290195b | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum |
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