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Record Information
Version1.0
Creation Date2016-09-30 22:27:53 UTC
Update Date2020-06-04 20:24:15 UTC
BMDB IDBMDB0000290
Secondary Accession Numbers
  • BMDB00290
Metabolite Identification
Common NameUridine diphosphate-N-acetylglucosamine
DescriptionUridine 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.
Structure
Thumb
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
Chemical FormulaC17H27N3O17P2
Average Molecular Weight607.3537
Monoisotopic Molecular Weight607.081569477
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number528-04-1
SMILESNot Available
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
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine nucleotide sugars
Alternative Parents
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
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Golgi
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Golgi
Biospecimen Locations
  • Adipose Tissue
  • Liver
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
  • Not Applicable
details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
  • Not Applicable
details
TestisDetected and Quantified268 +/- 40 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000290
DrugBank IDDB03397
Phenol Explorer Compound IDNot Available
FooDB IDFDB021930
KNApSAcK IDC00019358
Chemspider ID393240
KEGG Compound IDC00043
BioCyc IDUDP-N-ACETYL-D-GLUCOSAMINE
BiGG ID33638
Wikipedia LinkNot Available
METLIN ID5281
PubChem Compound445675
PDB IDNot Available
ChEBI ID16264
References
Synthesis ReferenceTakenouchi, Kenji; Ishige, Kazuya; Midorikawa, Yuichiro; Okuyama, Kiyoshi; Hamamoto, Tomoki; Noguchi, Toshitada. Process for producing uridine diphosphate-N-acetylglucosamine. PCT Int. Appl. (1999), 38 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in alpha-1,3-mannosylglycoprotein 2-beta-N-ace
Specific function:
Participates in O-mannosyl glycosylation by catalyzing the addition of N-acetylglucosamine to O-linked mannose on glycoproteins. Catalyzes the synthesis of the GlcNAc(beta1-2)Man(alpha1-)O-Ser/Thr moiety on alpha-dystroglycan and other O-mannosylated proteins, providing the necessary basis for the addition of further carbohydrate moieties. Is specific for alpha linked terminal mannose.
Gene Name:
POMGNT1
Uniprot ID:
Q5EAB6
Molecular weight:
75077.0
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Catalyzes the initial step of dolichol-linked oligosaccharide biosynthesis in N-linked protein glycosylation pathway: transfers GlcNAc-1-P from UDP-GlcNAc onto the carrier lipid dolichyl phosphate (P-dolichol), yielding GlcNAc-P-P-dolichol.
Gene Name:
DPAGT1
Uniprot ID:
Q5EA65
Molecular weight:
46045.0
General function:
Involved in glucuronosyl-N-acetylglucosaminyl-proteogly
Specific function:
Glycosyltransferase required for the biosynthesis of heparan-sulfate. The EXT1/EXT2 complex possesses substantially higher glycosyltransferase activity than EXT1 or EXT2 alone. Appears to be a tumor suppressor. Required for the exosomal release of SDCBP, CD63 and syndecan.
Gene Name:
EXT2
Uniprot ID:
O77783
Molecular weight:
81887.0
General function:
Involved in glucuronosyl-N-acetylglucosaminyl-proteogly
Specific function:
Glycosyltransferase required for the biosynthesis of heparan-sulfate. The EXT1/EXT2 complex possesses substantially higher glycosyltransferase activity than EXT1 or EXT2 alone. Required for the exosomal release of SDCBP, CD63 and syndecan (By similarity).
Gene Name:
EXT1
Uniprot ID:
A5D7I4
Molecular weight:
86299.0
General function:
Involved in alpha-1,3-mannosylglycoprotein 4-beta-N-ace
Specific function:
Glycosyltransferase that participates in the transfer of N-acetylglucosamine (GlcNAc) to the core mannose residues of N-linked glycans. Catalyzes the formation of the GlcNAcbeta1-4 branch on the GlcNAcbeta1-2Manalpha1-3 arm of the core structure of N-linked glycans. Essential for the production of tri- and tetra-antennary N-linked sugar chains. Involved in glucose transport by mediating SLC2A2/GLUT2 glycosylation, thereby controlling cell-surface expression of SLC2A2 in pancreatic beta cells.
Gene Name:
MGAT4A
Uniprot ID:
O77836
Molecular weight:
61618.0
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGH
Uniprot ID:
Q32L89
Molecular weight:
21006.0
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Involved in GPI anchor biosynthesis. Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGC
Uniprot ID:
Q3ZBX1
Molecular weight:
33628.0
General function:
Involved in beta-1,3-galactosyl-O-glycosyl-glycoprotein
Specific function:
Glycosyltransferase that catalyzes the transfer of an N-acetylglucosamine moiety onto mucin-type core 1 O-glycan to form the branched mucin-type core 2 O-glycan. Mucin-type core 2 O-glycans play an important role in leukocyte extravasation as they serve as scaffolds for the display of the selectin ligand sialyl Lewis X by leukocytes.
Gene Name:
GCNT1
Uniprot ID:
Q92180
Molecular weight:
49734.0
General function:
Involved in beta-1,3-galactosyl-O-glycosyl-glycoprotein
Specific function:
Glycosyltransferase that can synthesize all known mucin beta 6 N-acetylglucosaminides. Mediates core 2 and core 4 O-glycan branching, 2 important steps in mucin-type biosynthesis. Has also I-branching enzyme activity by converting linear into branched poly-N-acetyllactosaminoglycans, leading to introduce the blood group I antigen during embryonic development.
Gene Name:
GCNT3
Uniprot ID:
Q7YQE1
Molecular weight:
50953.0
General function:
Involved in N-acetyllactosaminide beta-1,3-N-acetylgluc
Specific function:
Beta-1,4-glucuronyltransferase involved in O-mannosylation of alpha-dystroglycan (DAG1). Transfers a glucuronic acid (GlcA) residue onto a xylose (Xyl) acceptor to produce the glucuronyl-beta-1,4-xylose-beta disaccharide primer, which is further elongated by LARGE1, during synthesis of phosphorylated O-mannosyl glycan. Phosphorylated O-mannosyl glycan is a carbohydrate is a carbohydrate structure present in alpha-dystroglycan (DAG1), which is required for binding laminin G-like domain-containing extracellular proteins with high affinity. Required for axon guidance; via its function in O-mannosylation of alpha-dystroglycan (DAG1).
Gene Name:
B4GAT1
Uniprot ID:
Q5EA01
Molecular weight:
47231.0
General function:
Carbohydrate transport and metabolism
Specific function:
Uridine diphosphate-N-acetylglucosamine (UDP-GlcNAc) transporter in the Golgi apparatus. May supply UDP-GlcNAc as substrate for Golgi-resident glycosyltransferases that generate branching of diantennary oligosaccharides (By similarity).
Gene Name:
SLC35A3
Uniprot ID:
Q6YC49
Molecular weight:
36067.0
General function:
Not Available
Specific function:
Not Available
Gene Name:
UAP1
Uniprot ID:
F1MJP7
Molecular weight:
58623.0
Reactions
N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate → Uridine diphosphate-N-acetylglucosamine + Pyrophosphatedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
GNE
Uniprot ID:
F1MIL9
Molecular weight:
79390.0
Reactions
Uridine diphosphate-N-acetylglucosamine + Water → N-Acetyl-D-mannosamine + Uridine 5'-diphosphatedetails