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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 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
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 Properties
PropertyValueSource
logP-1.4ALOGPS
logP-5.3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area300.41 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity117.56 m³·mol⁻¹ChemAxon
Polarizability50.39 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (n TMS)splash10-00di-9620000000-18841b4db9b69a91db36View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-18841b4db9b69a91db36View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f96-5924660000-c11cc7fa21a050c0f373View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03di-5501619000-8584f57aecb61fc3e5b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-5543009000-8a176d160a1f074ab319View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-05cr-4796000000-6c09aa3a2dac66281973View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-5543009000-8a176d160a1f074ab319View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-05cr-4796000000-6c09aa3a2dac66281973View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910020000-b4f448790a5adc1b2231View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3921000000-b1ea97b129b6c701887eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5910000000-af36b4483c7d5529ce86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01pc-9801421000-87db24d9515a2033d9b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01po-9605020000-323a53bc8a8e293636d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5911000000-aee8e2f7d665fa10b3b1View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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