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Identification |
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YMDB ID | YMDB00277 |
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Name | Uridine diphosphate-N-acetylglucosamine |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Uridine diphosphate-N-acetylglucosamine, also known as UDP-N-acetyl-D-glucosamine or UDP-glcnac, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Uridine diphosphate-N-acetylglucosamine is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine diphosphate-N-acetylglucosamine exists in all living species, ranging from bacteria to humans. Within yeast, uridine diphosphate-N-acetylglucosamine participates in a number of enzymatic reactions. In particular, dolichol phosphate and uridine diphosphate-N-acetylglucosamine can be converted into uridine 5'-monophosphate and N-acetyl-α-D-glucosaminyl-diphosphodolichol; which is catalyzed by the enzyme UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase. In addition, N-acetyl-α-D-glucosaminyl-diphosphodolichol and uridine diphosphate-N-acetylglucosamine can be converted into (N-acetylglucosaminyl)2-diphosphodolichol and UDP; which is mediated by the enzyme N-acetylglucosaminyldiphosphodolichol N-acetylglucosaminyltransferase. In yeast, uridine diphosphate-N-acetylglucosamine is involved in the metabolic pathway called n-glycan biosynthesis pathway. |
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Structure | |
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Synonyms | - [[3-acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinate
- [[3-acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinic acid
- N-[2-[[[5-[(2,4-dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide
- UDP-a-D-N-acetylglucosamine
- UDP-acetyl-D-glucosamine
- UDP-acetyl-delta-glucosamine
- UDP-acetylglucosamine
- UDP-alpha-D-N-acetylglucosamine
- UDP-alpha-delta-N-acetylglucosamine
- UDP-GlcNAc
- UDP-N-acetyl-D-glucosamine
- UDP-N-acetyl-delta-glucosamine
- UDP-N-acetyl-glucosamine
- UDP-N-acetylglucosamine
- UPPAG
- Uridine 5'-Diphospho-N-Acetlyglucosamine
- Uridine 5'-diphospho-N-acetylglucosamine
- Uridine diphosphate N-acetyl-D-glucosamine
- Uridine diphosphate N-acetyl-delta-glucosamine
- Uridine diphosphate N-acetylglucosamine
- Uridine diphospho-2-acetamido-2-deoxy-D-glucose
- Uridine diphospho-2-acetamido-2-deoxy-delta-glucose
- Uridine diphospho-N-acetyl-D-glucosamine
- Uridine diphospho-N-acetyl-delta-glucosamine
- Uridine diphospho-N-acetylglucosamine
- uridine diphosphoacetylglucosamine
- Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-glucopyranosyl ester
- Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl ester
- Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl ester
- Uridine pyrophosphoacetylglucosamine
- (2R,3R,4R,5S,6R)-3-(Acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphate (non-preferred name)
- URIDINE-diphosphATE-N-acetylglucosamine
- (2R,3R,4R,5S,6R)-3-(Acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphoric acid (non-preferred name)
- URIDINE-diphosphoric acid-N-acetylglucosamine
- Uridine diphosphoric acid-N-acetylglucosamine
- Acetylglucosamine, UDP
- Diphosphate N-acetylglucosamine, uridine
- Diphospho-N-acetylglucosamine, uridine
- N-Acetylglucosamine, uridine diphosphate
- Pyrophosphoacetylglucosamine, uridine
- UDP Acetylglucosamine
- UDPGNAc
- Uridine diphosphate N acetylglucosamine
- Uridine diphospho N acetylglucosamine
- UDP N-acetyl-alpha-D-glucosamine
- UDP N-acetyl-α-D-glucosamine
- UDP-α-D-N-acetylglucosamine
- Uridine 5'-(2-acetamido-2-deoxy-alpha-D-glucosyl pyrophosphate)
- Uridine 5'-(2-acetamido-2-deoxy-α-D-glucosyl pyrophosphate)
- Uridine 5’-(2-acetamido-2-deoxy-α-D-glucosyl pyrophosphate)
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CAS number | 528-04-1 |
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Weight | Average: 607.3537 Monoisotopic: 607.081569477 |
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InChI Key | LFTYTUAZOPRMMI-CFRASDGPSA-N |
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InChI | InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1 |
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IUPAC Name | [({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid |
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Traditional IUPAC Name | udp-N-acetyl-α-D-glucosamine |
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Chemical Formula | C17H27N3O17P2 |
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SMILES | [H]OC([H])([H])[C@@]1([H])O[C@]([H])(OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])[C@@]2([H])O[C@@]([H])(N3C([H])=C([H])C(=O)N([H])C3=O)[C@]([H])(O[H])[C@]2([H])O[H])[C@]([H])(N([H])C(=O)C([H])([H])[H])[C@@]([H])(O[H])[C@]1([H])O[H] |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Pyrimidine nucleotides |
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Sub Class | Pyrimidine nucleotide sugars |
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Direct Parent | Pyrimidine nucleotide sugars |
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Alternative Parents | |
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Substituents | - Pyrimidine nucleotide sugar
- Pyrimidine ribonucleoside diphosphate
- Pentose phosphate
- Pentose-5-phosphate
- N-acyl-alpha-hexosamine
- Glycosyl compound
- N-glycosyl compound
- Monosaccharide phosphate
- Organic pyrophosphate
- Pyrimidone
- Monoalkyl phosphate
- Hydropyrimidine
- Monosaccharide
- Organic phosphoric acid derivative
- Oxane
- Phosphoric acid ester
- Pyrimidine
- Alkyl phosphate
- Vinylogous amide
- Acetamide
- Tetrahydrofuran
- Heteroaromatic compound
- Urea
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Lactam
- Azacycle
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Organopnictogen compound
- Organooxygen compound
- Alcohol
- Primary alcohol
- Organic nitrogen compound
- Organic oxygen compound
- Organic oxide
- Carbonyl group
- Hydrocarbon derivative
- Organonitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | Not Available |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | Not Available | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | Amino sugar and nucleotide sugar metabolism | PW002413 | | N-Glycan biosynthesis | PW002501 | |
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KEGG Pathways | Amino sugar and nucleotide sugar metabolism | ec00520 | | N-Glycan biosynthesis | ec00510 | |
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SMPDB Reactions | |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (n TMS) | splash10-00di-9620000000-18841b4db9b69a91db36 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9620000000-18841b4db9b69a91db36 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0f96-5924660000-c11cc7fa21a050c0f373 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-03di-5501619000-8584f57aecb61fc3e5b6 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0a4i-5543009000-8a176d160a1f074ab319 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative | splash10-05cr-4796000000-6c09aa3a2dac66281973 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0a4i-5543009000-8a176d160a1f074ab319 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-05cr-4796000000-6c09aa3a2dac66281973 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0001009000-e88e6eea15ad8fc9b709 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00c0-9888000000-16b2da999d70ccc32a89 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0000009000-188ffcd0e9d1b77d6dad | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-05e9-8797000000-983e38107655bbf90446 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-2690000000-72b9c4b0b3951bc57b21 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-052r-4900000000-1c5f6fb7f312539ad699 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-05cr-4796000000-6c09aa3a2dac66281973 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0190000000-575647844027e90d57ad | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0910020000-b4f448790a5adc1b2231 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-3921000000-b1ea97b129b6c701887e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-5910000000-af36b4483c7d5529ce86 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-01pc-9801421000-87db24d9515a2033d9b0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01po-9605020000-323a53bc8a8e293636d7 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-06tf-5911000000-aee8e2f7d665fa10b3b1 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0000029000-6a481f04b19fa3177889 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a6s-5100192000-07c7ec84c4bab85e334a | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-053u-4719110000-3a1b07828c441361af2f | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00mk-0000982000-8e4f05f581cea906b6bb | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0hi2-0213591000-da4a947496986866c59e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4j-6980020000-82befaa44d12d4c3c15d | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Milewski, S., Gabriel, I., Olchowy, J. (2006). "Enzymes of UDP-GlcNAc biosynthesis in yeast." Yeast 23:1-14.16408321
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Synthesis Reference: | Takenouchi, Kenji; Ishige, Kazuya; Midorikawa, Yuichiro; Okuyama, Kiyoshi; Hamamoto, Tomoki; Noguchi, Toshitada. Process for producing uridine diphosphate-N-acetylglucosamine. PCT Int. Appl. (1999), 38 pp. |
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