Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 01:44:54 UTC |
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Update date | 2015-07-21 06:59:32 UTC |
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Primary ID | FDB028783 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (Mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol |
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Description | (Mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol (Man3GlcNAc2-Dol) is an isoprene-based lipid where an oligosaccharide moiety Man3GlcNAc2 is linked to dolichol lipid via a pyrophosphate linkage. Man3GlcNAc2-Dol is an intermediate in dolichyl-diphosphooligosaccaride biosynthesis pathway and synthesis of N-glycans. The biosynthetic pathway for this lipid-linked precursor begins with the phosphorylation of dolichol, followed by stepwise addition of sugar residues to form the product dolichyl-diphosphooligosaccharide. This pathway is of particular interest in humans, because defects in the glycosyltransferases involved lead to congenital disorders of N-glycosylation of proteins. In this pathway, (Mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol is formed from (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol via reaction with Dolichyl β-D-mannosyl phosphate. In the next step, one more mannose residue is added to Man3GlcNAc2-Dol via reaction with Dolichyl β-D-mannosyl phosphate. (Adapted from Human Cyc) [HMDB] |
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CAS Number | Not Available |
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Structure | |
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Synonyms | Synonym | Source |
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Not Available | Not Available |
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Predicted Properties | |
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Chemical Formula | C114H190N2O32P2 |
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IUPAC name | {[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-5-{[(2S,3S,4S,5R,6R)-3,5-dihydroxy-4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-({[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}[({[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid |
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InChI Identifier | InChI=1S/C114H190N2O32P2/c1-72(2)35-20-36-73(3)37-21-38-74(4)39-22-40-75(5)41-23-42-76(6)43-24-44-77(7)45-25-46-78(8)47-26-48-79(9)49-27-50-80(10)51-28-52-81(11)53-29-54-82(12)55-30-56-83(13)57-31-58-84(14)59-32-60-85(15)61-33-62-86(16)63-34-64-87(17)65-66-138-149(133,134)148-150(135,136)147-111-96(116-89(19)122)101(127)107(93(70-120)142-111)144-110-95(115-88(18)121)100(126)108(92(69-119)141-110)145-114-106(132)109(146-113-105(131)103(129)98(124)91(68-118)140-113)99(125)94(143-114)71-137-112-104(130)102(128)97(123)90(67-117)139-112/h35,37,39,41,43,45,47,49,51,53,55,57,59,61,63,87,90-114,117-120,123-132H,20-34,36,38,40,42,44,46,48,50,52,54,56,58,60,62,64-71H2,1-19H3,(H,115,121)(H,116,122)(H,133,134)(H,135,136)/b73-37+,74-39+,75-41+,76-43+,77-45+,78-47+,79-49+,80-51+,81-53+,82-55+,83-57+,84-59+,85-61+,86-63+/t87?,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102+,103+,104+,105+,106+,107-,108-,109+,110+,111+,112+,113-,114+/m1/s1 |
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InChI Key | BKUXVZCTYBVOAV-JLQUOVFMSA-N |
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Isomeric SMILES | OC[C@H]1O[C@H](OC[C@H]2O[C@@H](O[C@H]3[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]3CO)O[C@H]3[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]3CO)OP(=O)(O)OP(=O)(O)OCCC(C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@@H](O)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O |
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Average Molecular Weight | 2162.6701 |
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Monoisotopic Molecular Weight | 2161.277695018 |
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Classification |
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Description | Belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Polyprenols |
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Direct Parent | Polyprenyl phospho carbohydrates |
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Alternative Parents | |
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Substituents | - Polyprenyl phospho oligosaccharide
- Polyterpenoid
- Polyprenyl phospho carbohydrate
- Dolichyl diphosphate
- Oligosaccharide phosphate
- Polyprenyl monophosphate
- Oligosaccharide
- Polyprenyl phosphate skeleton
- N-acyl-alpha-hexosamine
- Glycosyl compound
- O-glycosyl compound
- Organic pyrophosphate
- Monoalkyl phosphate
- Organic phosphoric acid derivative
- Alkyl phosphate
- Oxane
- Phosphoric acid ester
- Acetamide
- Secondary alcohol
- Secondary carboxylic acid amide
- Carboxamide group
- Polyol
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Acetal
- Organic nitrogen compound
- Organic oxide
- Hydrocarbon derivative
- Alcohol
- Organonitrogen compound
- Organooxygen compound
- Carbonyl group
- Organic oxygen compound
- Organopnictogen 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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Disposition | Route of exposure: Biological location: Source: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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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 | splash10-0006-5900104003-09db0f060952139dc7c7 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9410304013-0ccd36300fab32eefc3f | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000x-9601208115-8c34bda60924b7a995f3 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-1551173900-05c62439a775de55a3c5 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01r7-4931211011-b7e680ec40e0c5a7c02f | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-054n-4940110000-ce57e0b0681f33bbdfb7 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-1900000000-52ce5860d1c565fc0e7f | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08fu-4900001001-44ab67fe16fadf8ed56a | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0pb9-3970345010-8dd8dba9d0a19515d233 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-4900000000-bf696591d9db91e0b7d1 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0w31-6700323129-6f809b436f6b934c6f80 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dj-9501737368-c54b73a653e73ea159e2 | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 53481371 |
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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 | HMDB12119 |
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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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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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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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