Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:27:53 UTC |
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Update Date | 2020-06-04 20:24:15 UTC |
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BMDB ID | BMDB0000290 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Uridine diphosphate-N-acetylglucosamine |
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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. |
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Structure | |
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Synonyms | Value | Source |
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(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) | ChEBI | UDP-GlcNAc | ChEBI | UDP-N-Acetyl-D-glucosamine | ChEBI | UDP-N-Acetylglucosamine | ChEBI | URIDINE-diphosphATE-N-acetylglucosamine | ChEBI | (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) | Generator | URIDINE-diphosphoric acid-N-acetylglucosamine | Generator | Uridine diphosphoric acid-N-acetylglucosamine | Generator | 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 | HMDB | UDP-a-D-N-Acetylglucosamine | HMDB | UDP-Acetyl-D-glucosamine | HMDB | UDP-Acetyl-delta-glucosamine | HMDB | UDP-Acetylglucosamine | HMDB | UDP-alpha-D-N-Acetylglucosamine | HMDB | UDP-alpha-delta-N-Acetylglucosamine | HMDB | UDP-N-Acetyl-delta-glucosamine | HMDB | UDP-N-Acetyl-glucosamine | HMDB | UPPAG | HMDB | Uridine 5'-diphospho-N-acetlyglucosamine | HMDB | Uridine 5'-diphospho-N-acetylglucosamine | HMDB | Uridine diphosphate N-acetyl-D-glucosamine | HMDB | Uridine diphosphate N-acetyl-delta-glucosamine | HMDB | Uridine diphosphate N-acetylglucosamine | HMDB | Uridine diphospho-2-acetamido-2-deoxy-D-glucose | HMDB | Uridine diphospho-2-acetamido-2-deoxy-delta-glucose | HMDB | Uridine diphospho-N-acetyl-D-glucosamine | HMDB | Uridine diphospho-N-acetyl-delta-glucosamine | HMDB | Uridine diphospho-N-acetylglucosamine | HMDB | Uridine diphosphoacetylglucosamine | HMDB | Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-glucopyranosyl ester | HMDB | Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl ester | HMDB | Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl ester | HMDB | Uridine pyrophosphoacetylglucosamine | HMDB | [[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 | HMDB | [[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 | HMDB | Acetylglucosamine, UDP | HMDB | Diphosphate N-acetylglucosamine, uridine | HMDB | Diphospho-N-acetylglucosamine, uridine | HMDB | N-Acetylglucosamine, uridine diphosphate | HMDB | Pyrophosphoacetylglucosamine, uridine | HMDB | UDP Acetylglucosamine | HMDB | UDPGNAc | HMDB | Uridine diphosphate N acetylglucosamine | HMDB | Uridine diphospho N acetylglucosamine | HMDB | UDP N-acetyl-alpha-D-glucosamine | HMDB | UDP N-acetyl-α-D-glucosamine | HMDB | UDP-α-D-N-acetylglucosamine | HMDB | Uridine 5'-(2-acetamido-2-deoxy-alpha-D-glucosyl pyrophosphate) | HMDB | Uridine 5'-(2-acetamido-2-deoxy-α-D-glucosyl pyrophosphate) | HMDB | Uridine 5’-(2-acetamido-2-deoxy-α-D-glucosyl pyrophosphate) | HMDB |
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Chemical Formula | C17H27N3O17P2 |
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Average Molecular Weight | 607.3537 |
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Monoisotopic Molecular Weight | 607.081569477 |
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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 Name | udp-N-acetyl-α-D-glucosamine |
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CAS Registry Number | 528-04-1 |
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SMILES | CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O |
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InChI Identifier | 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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InChI Key | LFTYTUAZOPRMMI-CFRASDGPSA-N |
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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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Ontology |
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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | |
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Physical Properties |
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State | Solid |
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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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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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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 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9620000000-18841b4db9b69a91db36 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0f96-5924660000-c11cc7fa21a050c0f373 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-03di-5501619000-8584f57aecb61fc3e5b6 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0a4i-5543009000-8a176d160a1f074ab319 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative | splash10-05cr-4796000000-6c09aa3a2dac66281973 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0a4i-5543009000-8a176d160a1f074ab319 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-05cr-4796000000-6c09aa3a2dac66281973 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0001009000-e88e6eea15ad8fc9b709 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00c0-9888000000-16b2da999d70ccc32a89 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0000009000-188ffcd0e9d1b77d6dad | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-05e9-8797000000-983e38107655bbf90446 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-2690000000-72b9c4b0b3951bc57b21 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-052r-4900000000-1c5f6fb7f312539ad699 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-05cr-4796000000-6c09aa3a2dac66281973 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0190000000-575647844027e90d57ad | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0910020000-b4f448790a5adc1b2231 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-3921000000-b1ea97b129b6c701887e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-5910000000-af36b4483c7d5529ce86 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-01pc-9801421000-87db24d9515a2033d9b0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01po-9605020000-323a53bc8a8e293636d7 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-06tf-5911000000-aee8e2f7d665fa10b3b1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0000029000-6a481f04b19fa3177889 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a6s-5100192000-07c7ec84c4bab85e334a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-053u-4719110000-3a1b07828c441361af2f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00mk-0000982000-8e4f05f581cea906b6bb | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0hi2-0213591000-da4a947496986866c59e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4j-6980020000-82befaa44d12d4c3c15d | View in MoNA |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | Not Available | View in JSpectraViewer |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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