CAS 528-04-1 Uridine-Diphosphate-N-Acetylglucosamine (HCID 445675)

Substructure search Find similar structures

Basic information

CAS: 528-04-1
Standard SMILES: CC(=O)N[C@H]1[C@@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChIKey: LFTYTUAZOPRMMI-CFRASDGPSA-N
Molecular formula: C17H27N3O17P2
Average molar mass: 607.4 g/mol
Monoisotopic mass: 607.08156966

Overview

UDP-N-acetyl-alpha-D-glucosamine is a UDP-amino sugar having N-acetyl-alpha-D-glucosamine as the amino sugar component. It has a role as a mouse metabolite and an Escherichia coli metabolite. It is functionally related to an UDP-D-glucosamine. It is a conjugate acid of an UDP-N-acetyl-alpha-D-glucosamine(2-).

Names & identifiers

Preferred name: Uridine-Diphosphate-N-Acetylglucosamine
IUPAC: [(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
English name: [[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy
Molecular formula: C17H27N3O17P2
Molecular weight: 607.35

Names & synonyms

URIDINE-DIPHOSPHATE-N-ACETYLGLUCOSAMINERefChem:901487UDP-N-acetylglucosamineUDP-GlcNAcUDP-N-acetyl-D-glucosamineUDP-acetylglucosamineUPPAGUDP-alpha-D-N-acetylglucosamine528-04-1UDP-N-acetyl-alpha-D-glucosamine[(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 phosphateUDP-acetyl-D-glucosamine

Show more names

Uridine diphosphate-N-acetylglucosamineUridine Impurity 29Glutamic Acid Impurity 8UDP N-acetyl-alpha-D-glucosamineUridine 5'-(2-acetamido-2-deoxy-alpha-D-glucosyl pyrophosphate)[[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyUridinediphosphate-N-acetylglucosamineUridinediphosphate-N-acetylglucosamineUridine 5'-(trihydrogen diphosphate), P'-[2-(acetylamino)-2-deoxy-α-D-glucopyranosyl] ester

Properties

Computed structural properties

XLogP: -6.6
Topological polar surface area: 300 Å²
Hydrogen bond donors: 9
Hydrogen bond acceptors: 17
Rotatable bonds: 10
Heavy atoms: 39
Formal charge: 0
Complexity: 1,080

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

LipidsLipids -> Saccharolipids [SL] -> Acylaminosugars [SL01] -> Monoacylaminosugars [SL0101]

Physical DescriptionSolid

Collision Cross Section · 2 items

208.8 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

210.4 Å² [M+H]+

Physicochemical properties

Density: 1.86 · 1.86±0.1 g/cm3(Predicted)
pka: 1.1 · 1.10±0.50(Predicted)

Chemistry & industry

Pharmacology

Tissue LocationsAdipose Tissue

Cellular LocationsGolgi apparatus

Metabolite PathwaysAmino Sugar Metabolism

Applications

UsesUridine 5’-Diphospho-N-acetylglucosamine-13C,d3 is the isotope labelled analog of Uridine 5’-Diphospho-N-acetylglucosamine (U829925, Disodium Salt); a chemical reagent used in studies relating to the synthesis of immunogens.