Uridine-diphosphate-N-acetylglucosamine

Details

• Internal ID: a8602aa5-0a25-44c7-93b3-076141339565
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleotides > Pyrimidine nucleotide sugars
• 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
• SMILES (Canonical): CC(=O)NC1C(C(C(OC1OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)CO)O)O
• SMILES (Isomeric): 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
• 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
• InChI Key: LFTYTUAZOPRMMI-CFRASDGPSA-N
• Popularity: 743 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₇N₃O₁₇P₂
• Molecular Weight: 607.40 g/mol
• Exact Mass: 607.08157040 g/mol
• Topological Polar Surface Area (TPSA): 300.00 Ų
• XlogP: -6.60

Synonyms

• UDP-N-acetyl-D-glucosamine
• UDP-GlcNAc
• URIDINE-DIPHOSPHATE-N-ACETYLGLUCOSAMINE
• UDP-acetylglucosamine
• UPPAG
• UDP-N-acetyl-alpha-D-glucosamine
• CHEBI:16264
• uridine diphosphate N-acetylglucosamine
• UDP-acetyl-D-glucosamine
• 528-04-1
• 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
• 91183-98-1
• 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
• [(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
• Uridine diphospho-N-acetyl-delta-glucosamine
• Uridine diphosphate N-acetyl-delta-glucosamine
• C00043
• Q312208
• J-700272
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4518	Q15391	Purinergic receptor P2Y14	810 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.35%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.09%	98.95%
CHEMBL2123	P51582	Pyrimidinergic receptor P2Y4	94.76%	93.39%
CHEMBL226	P30542	Adenosine A1 receptor	93.21%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	92.03%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.82%	91.11%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	86.39%	80.33%
CHEMBL255	P29275	Adenosine A2b receptor	86.11%	98.59%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	85.91%	87.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.32%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.91%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	84.44%	92.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.83%	93.04%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	83.61%	81.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.12%	94.45%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.49%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.62%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.24%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.47%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.32%	85.14%

Plants that contains it

• Helianthus tuberosus

Cross-Links

• PubChem: 445675
• LOTUS: LTS0269624
• wikiData: Q312208