Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:24:29 UTC
Update Date2024-04-30 19:36:07 UTC
Metabolite IDMMDBc0029492
Metabolite Identification
Common NameUridine diphosphate-N-acetylglucosamine
DescriptionUridine diphosphate N-acetylglucosamine or UDP-GlcNAc is a nucleotide sugar and a coenzyme in metabolism. It is used by glycosyltransferases to transfer N-acetylglucosamine residues to substrates. D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of all nitrogen-containing sugars. Specifically, glucosamine-6-phosphate is synthesized from fructose 6-phosphate and glutamine as the first step of the hexosamine biosynthesis pathway. The end-product of this pathway is UDP-GlcNAc, which is then used for making glycosaminoglycans, proteoglycans, and glycolipids.
Structure
Synonyms
ValueSource
(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-GlcNAcChEBI
UDP-N-Acetyl-D-glucosamineChEBI
UDP-N-AcetylglucosamineChEBI
URIDINE-diphosphATE-N-acetylglucosamineChEBI
(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-acetylglucosamineGenerator
Uridine diphosphoric acid-N-acetylglucosamineGenerator
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]acetamideHMDB
UDP-a-D-N-AcetylglucosamineHMDB
UDP-Acetyl-D-glucosamineHMDB
UDP-Acetyl-delta-glucosamineHMDB
UDP-AcetylglucosamineHMDB
UDP-alpha-D-N-AcetylglucosamineHMDB
UDP-alpha-delta-N-AcetylglucosamineHMDB
UDP-N-Acetyl-delta-glucosamineHMDB
UDP-N-Acetyl-glucosamineHMDB
UPPAGHMDB
Uridine 5'-diphospho-N-acetlyglucosamineHMDB
Uridine 5'-diphospho-N-acetylglucosamineHMDB
Uridine diphosphate N-acetyl-D-glucosamineHMDB
Uridine diphosphate N-acetyl-delta-glucosamineHMDB
Uridine diphosphate N-acetylglucosamineHMDB
Uridine diphospho-2-acetamido-2-deoxy-D-glucoseHMDB
Uridine diphospho-2-acetamido-2-deoxy-delta-glucoseHMDB
Uridine diphospho-N-acetyl-D-glucosamineHMDB
Uridine diphospho-N-acetyl-delta-glucosamineHMDB
Uridine diphospho-N-acetylglucosamineHMDB
Uridine diphosphoacetylglucosamineHMDB
Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-glucopyranosyl esterHMDB
Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl esterHMDB
Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl esterHMDB
Uridine pyrophosphoacetylglucosamineHMDB
[[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]phosphinateHMDB
[[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 acidHMDB
Acetylglucosamine, UDPHMDB
Diphosphate N-acetylglucosamine, uridineHMDB
Diphospho-N-acetylglucosamine, uridineHMDB
N-Acetylglucosamine, uridine diphosphateHMDB
Pyrophosphoacetylglucosamine, uridineHMDB
UDP AcetylglucosamineHMDB
UDPGNAcHMDB
Uridine diphosphate N acetylglucosamineHMDB
Uridine diphospho N acetylglucosamineHMDB
UDP N-acetyl-alpha-D-glucosamineHMDB
UDP N-acetyl-α-D-glucosamineHMDB
UDP-α-D-N-acetylglucosamineHMDB
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
Molecular FormulaC17H27N3O17P2
Average Mass607.3537
Monoisotopic Mass607.081569477
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
Traditional Nameudp-N-acetyl-α-D-glucosamine
CAS Registry Number528-04-1
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
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
InChI KeyLFTYTUAZOPRMMI-CFRASDGPSA-N