Uridine-Diphosphate-N-Acetylglucosamine
PubChem CID: 445675
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| Compound Synonyms | UDP-N-acetylglucosamine, URIDINE-DIPHOSPHATE-N-ACETYLGLUCOSAMINE, UDP-GlcNAc, UDP-N-acetyl-D-glucosamine, UDP-acetylglucosamine, UPPAG, UDP-N-acetyl-alpha-D-glucosamine, CHEBI:16264, uridine diphosphate N-acetylglucosamine, [(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate, UDP-acetyl-D-glucosamine, 528-04-1, 91183-98-1, Uridine diphospho-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 diphosphate (non-preferred name), UDP-a-D-N-acetylglucosamine, UDP-alpha-D-N-acetylglucosamine, Uridine diphosphoacetylglucosamine, UDP-N-acetyl-glucosamine, Udpx, Uridine 5'-diphospho-N-acetylglucosamine, Uridine diphospho-N-acetyl-D-glucosamine, 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, UD1, Uridine diphosphate N-acetyl-D-glucosamine, Uridine diphospho-2-acetamido-2-deoxy-D-glucose, UDP N-acetyl-glucosamine, UDP-acetyl-delta-glucosamine, UDP-, A-D-N-acetylglucosamine, CHEMBL388154, GTPL1779, SCHEMBL1521296, UDP-N-acetyl-delta-glucosamine, LFTYTUAZOPRMMI-CFRASDGPSA-N, UDP N-acetyl-alpha-D-glucosamine, UDP-alpha-delta-N-acetylglucosamine, DB03397, Uridine 5'-Diphospho-N-Acetlyglucosamine, Uridine diphospho-N-acetyl-delta-glucosamine, NS00015645, Uridine diphosphate N-acetyl-delta-glucosamine, C00043, Q312208, Uridine diphospho-2-acetamido-2-deoxy-delta-glucose, 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 5'-[3-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl) dihydrogen diphosphate], [[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, {[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid |
|---|---|
| Ghose Rule | False |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 300.0 |
| Hydrogen Bond Donor Count | 9.0 |
| Pfizer 3 75 Rule | True |
| Scaffold Graph Level | CC(CCC1CCC(C2CCC(C)CC2C)C1)CC(C)CC1CCCCC1 |
| Np Classifier Class | Aminosugars |
| Deep Smiles | OC[C@H]O[C@H]OP=O)OP=O)OC[C@H]O[C@H][C@@H][C@@H]5O))O))nccc=O)[nH]c6=O))))))))))))O)))O)))[C@@H][C@H][C@@H]6O))O))NC=O)C |
| Heavy Atom Count | 39.0 |
| Pathway Kegg Map Id | map00520 |
| Classyfire Class | Pyrimidine nucleotides |
| Description | Uridine 5'-diphosphate-GlcNAc (UDP-Glc-NAc )respond to nutrient excess to activate O-GlcNAcylation (addition of O-linked N-acetylglucosamine) in the hexosamine signaling pathway (HSP). O-GlcNAc addition (and removal) is key to histone remodeling, transcription, proliferation, apoptosis, and proteasomal degradation. This nutrient-responsive signaling pathway also modulates important cellular pathways, including the insulin signaling cascade in. Alterations in O-GlcNAc metabolism are associated with various human diseases including diabetes mellitus and neurodegeneration. (PMID: 16317114) The incidence of type 2 diabetes (non-insulin-dependent diabetes mellitus) has increased to epidemic proportions, being described as a disease of 'chronic overnutrition'. Due to the chemical makeup of UDP-GlcNAc,it is well positioned to serve as a glucose sensor in that it is a high-energy compound that requires and/or responds to glucose, amino acid, fatty acid and nucleotide metabolism for synthesis. UDP-Glc-NAc is the donor substrate for modification of nucleocytoplasmic proteins at serine and threonine residues with N-acetylglucosamine. Elevated levels of O-GlcNAc have an effect on insulin-stimulated glucose uptake. (PMID: 12678487) [HMDB] |
| Scaffold Graph Node Level | OC1CCN(C2CCC(COP(O)OP(O)OC3CCCCO3)O2)C(O)N1 |
| Classyfire Subclass | Pyrimidine nucleotide sugars |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 1080.0 |
| Database Name | fooddb_chem_all;hmdb_chem_all;imppat_phytochem;pubchem |
| Defined Atom Stereocenter Count | 9.0 |
| Enzyme Uniprot Id | Q9Y223, Q9BRB3, P37287, Q14442, P57054, Q92535, Q16222, Q9H3H5, Q10469, Q16394, O43909, Q93063, Q92935, O43505, Q09328, O15294, Q09327, Q06430, Q9Y2D2, Q9NY97, Q9UBQ6, Q9UM21, Q9UQ53, Q9BYG0, Q3T906, Q9NP73 |
| Uniprot Id | Q9Y223, Q9BRB3, P37287, Q14442, P57054, Q92535, Q16222, Q9H3H5, Q10469, Q16394, Q92839, O43909, Q93063, Q92935, O43505, Q09328, O15294, O00219, Q09327, Q92819, Q06430, Q9Y2D2, Q9NY97, Q9UBQ6, Q9UM21, Q9UQ53, Q9BYG0, Q8WZA1, Q3T906, Q9NP73, Q5NDL2, Q02742, O95395, Q9P109, Q8N0V5, Q8NFS9, Q8NAT1, P26572, Q9UBM8, Q3V5L5, Q3KQV9 |
| Iupac Name | [(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate |
| Class | Pyrimidine nucleotides |
| Veber Rule | False |
| Classyfire Superclass | Nucleosides, nucleotides, and analogues |
| Xlogp | -6.6 |
| Superclass | Nucleosides, nucleotides, and analogues |
| Subclass | Pyrimidine nucleotide sugars |
| Gsk 4 400 Rule | False |
| Molecular Formula | C17H27N3O17P2 |
| Scaffold Graph Node Bond Level | O=c1ccn(C2CCC(CO[PH](=O)O[PH](=O)OC3CCCCO3)O2)c(=O)[nH]1 |
| Inchi Key | LFTYTUAZOPRMMI-CFRASDGPSA-N |
| Silicos It Class | Soluble |
| Rotatable Bond Count | 10.0 |
| State | Solid |
| Synonyms | (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 diate (non-preferred name), (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 diic acid (non-preferred name), [[3-acetylamino-4,5-Dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-oryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]inate, [[3-acetylamino-4,5-Dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-oryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]inic acid, [[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-inoyl]oxy-hydroxy-inoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide, 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'-dio-N-acetlyglucosamine, Uridine 5'-dio-N-acetylglucosamine, Uridine 5'-Diphospho-N-Acetlyglucosamine, Uridine 5'-diphospho-N-acetylglucosamine, Uridine diate N-acetyl-D-glucosamine, Uridine diate N-acetyl-delta-glucosamine, Uridine diate N-acetylglucosamine, Uridine dio-2-acetamido-2-deoxy-D-glucose, Uridine dio-2-acetamido-2-deoxy-delta-glucose, Uridine dio-N-acetyl-D-glucosamine, Uridine dio-N-acetyl-delta-glucosamine, Uridine dio-N-acetylglucosamine, Uridine dioacetylglucosamine, 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 pyroate 2-acetamido-2-deoxy-a-D-glucopyranosyl ester, Uridine pyroate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl ester, Uridine pyroate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl ester, Uridine pyrooacetylglucosamine, 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, URIDINE-diATE-N-acetylglucosamine, URIDINE-diic acid-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 diphosphate (non-preferred name), UDP-N-Acetyl-D-glucosamine, UDP-N-Acetylglucosamine, 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, 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-N-Acetyl-delta-glucosamine, UDP-N-Acetyl-glucosamine, Uridine 5'-diphospho-N-acetlyglucosamine, Uridine diphosphoacetylglucosamine, [[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, 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), uridine diphosphate n-acetylglucosamine |
| Substituent Name | Pyrimidine nucleotide sugar, Pyrimidine ribonucleoside diphosphate, N-acyl-alpha-hexosamine, Glucosamine, Amino sugar, N-glycosyl compound, Glycosyl compound, Organic pyrophosphate, Monosaccharide phosphate, Monoalkyl phosphate, Amino saccharide, Pyrimidone, Alkyl phosphate, Pyrimidine, Phosphoric acid ester, Oxane, Organic phosphoric acid derivative, Organic phosphate, Monosaccharide, Hydropyrimidine, Saccharide, Heteroaromatic compound, Acetamide, Vinylogous amide, Oxolane, Urea, Secondary carboxylic acid amide, Secondary alcohol, Lactam, Carboxamide group, 1,2-diol, Oxacycle, Azacycle, Organoheterocyclic compound, Ether, Carboxylic acid derivative, Carboxylic acid amide, Hydrocarbon derivative, Primary alcohol, Organooxygen compound, Organonitrogen compound, Carbonyl group, Alcohol, Aromatic heteromonocyclic compound |
| Esol Class | Highly soluble |
| Functional Groups | CC(=O)NC, CO, COC, COP(=O)(O)OP(=O)(O)O[C@H](C)OC, c=O, c[nH]c, cn(c)C |
| Compound Name | Uridine-Diphosphate-N-Acetylglucosamine |
| Kingdom | Organic compounds |
| Exact Mass | 607.082 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 607.082 |
| Hydrogen Bond Acceptor Count | 17.0 |
| Molecular Weight | 607.4 |
| Gi Absorption | False |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 9.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Lipinski Rule Of 5 | False |
| 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 |
| Smiles | CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)CO)O)O |
| Np Classifier Biosynthetic Pathway | Carbohydrates |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | False |
| Taxonomy Direct Parent | Pyrimidine nucleotide sugars |
| Np Classifier Superclass | Aminosugars and aminoglycosides |
- 1. Outgoing r'ship
FOUND_INto/from Vigna Radiata (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/13475324