Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Uridine-Diphosphate-N-Acetylglucosamine
- DrugBank Accession Number
- DB03397
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Uridine-Diphosphate-N-Acetylglucosamine (DB03397)
- Weight
- Average: 607.3537
Monoisotopic: 607.081569477 - Chemical Formula
- C17H27N3O17P2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AUDP-N-acetylglucosamine 1-carboxyvinyltransferase inhibitorEscherichia coli (strain K12) UUDP-N-acetylhexosamine pyrophosphorylase Not Available Humans UUDP-N-acetylglucosamine 1-carboxyvinyltransferase Not Available Shigella flexneri UUDP-glucose 4-epimerase Not Available Humans UUDP-glucose 4-epimerase Not Available Escherichia coli (strain K12) UExostosin-like 2 Not Available Humans UAlpha-1,3-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferase Not Available Humans UBifunctional protein GlmU Not Available Escherichia coli (strain K12) UBifunctional protein GlmU Not Available Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Pyrimidine nucleotides
- Sub Class
- Pyrimidine nucleotide sugars
- Direct Parent
- Pyrimidine nucleotide sugars
- Alternative Parents
- Pyrimidine ribonucleoside diphosphates / Pentose phosphates / N-acyl-alpha-hexosamines / Glycosylamines / Monosaccharide phosphates / Organic pyrophosphates / Monoalkyl phosphates / Pyrimidones / Hydropyrimidines / Oxanes show 16 more
- Substituents
- Acetamide / Alcohol / Alkyl phosphate / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Glycosyl compound / Heteroaromatic compound show 32 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- UDP-amino sugar (CHEBI:16264)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- LFTYTUAZOPRMMI-CFRASDGPSA-N
- 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
- IUPAC Name
- {[(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
- 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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000290
- KEGG Compound
- C00043
- PubChem Compound
- 445675
- PubChem Substance
- 46506870
- ChemSpider
- 393240
- ChEBI
- 16264
- ChEMBL
- CHEMBL388154
- ZINC
- ZINC000008551100
- PDBe Ligand
- UD1
- PDB Entries
- 1foa / 1fwy / 1g97 / 1hm9 / 1hv9 / 1hzj / 1i3m / 1i3n / 1jv1 / 1jvd … show 95 more
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 11.4 mg/mL ALOGPS logP -1.4 ALOGPS logP -5.3 Chemaxon logS -1.7 ALOGPS pKa (Strongest Acidic) 1.74 Chemaxon pKa (Strongest Basic) -3.5 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 14 Chemaxon Hydrogen Donor Count 9 Chemaxon Polar Surface Area 300.41 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 117.56 m3·mol-1 Chemaxon Polarizability 50.39 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9428 Blood Brain Barrier - 0.6722 Caco-2 permeable - 0.8058 P-glycoprotein substrate Non-substrate 0.6736 P-glycoprotein inhibitor I Non-inhibitor 0.8213 P-glycoprotein inhibitor II Non-inhibitor 0.9728 Renal organic cation transporter Non-inhibitor 0.9423 CYP450 2C9 substrate Non-substrate 0.5768 CYP450 2D6 substrate Non-substrate 0.8558 CYP450 3A4 substrate Non-substrate 0.5166 CYP450 1A2 substrate Non-inhibitor 0.8604 CYP450 2C9 inhibitor Non-inhibitor 0.8426 CYP450 2D6 inhibitor Non-inhibitor 0.8425 CYP450 2C19 inhibitor Non-inhibitor 0.7877 CYP450 3A4 inhibitor Inhibitor 0.5327 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7107 Ames test Non AMES toxic 0.7602 Carcinogenicity Non-carcinogens 0.8747 Biodegradation Not ready biodegradable 0.6335 Rat acute toxicity 2.3962 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9511 hERG inhibition (predictor II) Non-inhibitor 0.5183
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 228.4832302 predictedDarkChem Lite v0.1.0 [M-H]- 221.2249302 predictedDarkChem Lite v0.1.0 [M-H]- 218.64851 predictedDeepCCS 1.0 (2019) [M+H]+ 227.7121302 predictedDarkChem Lite v0.1.0 [M+H]+ 219.8389302 predictedDarkChem Lite v0.1.0 [M+H]+ 220.39781 predictedDeepCCS 1.0 (2019) [M+Na]+ 227.7667302 predictedDarkChem Lite v0.1.0 [M+Na]+ 219.7769302 predictedDarkChem Lite v0.1.0 [M+Na]+ 228.10152 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Cell wall formation (PubMed:1512209). Adds enolpyruvyl to UDP-N-acetylglucosamine (PubMed:1512209, PubMed:20392080). Target for the antibiotic fosfomycin.
- Specific Function
- UDP-N-acetylglucosamine 1-carboxyvinyltransferase activity
- Gene Name
- murA
- Uniprot ID
- P0A749
- Uniprot Name
- UDP-N-acetylglucosamine 1-carboxyvinyltransferase
- Molecular Weight
- 44817.24 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Catalyzes the last step in biosynthesis of uridine diphosphate-N-acetylglucosamine (UDP-GlcNAc) by converting UTP and glucosamine 1-phosphate (GlcNAc-1-P) to the sugar nucleotide (PubMed:9603950, PubMed:9765219). Also converts UTP and galactosamine 1-phosphate (GalNAc-1-P) into uridine diphosphate-N-acetylgalactosamine (UDP-GalNAc) (PubMed:9765219). In addition to its role in metabolism, acts as a regulator of innate immunity in response to virus infection by mediating pyrophosphorylation of IRF3: catalyzes pyrophosphorylation of IRF3 phosphorylated at 'Ser-386' by TBK1, promoting IRF3 dimerization and activation, leading to type I interferon responses (PubMed:36603579)
- Specific Function
- identical protein binding
- Gene Name
- UAP1
- Uniprot ID
- Q16222
- Uniprot Name
- UDP-N-acetylhexosamine pyrophosphorylase
- Molecular Weight
- 58768.705 Da
References
- Kind
- Protein
- Organism
- Shigella flexneri
- Pharmacological action
- Unknown
- General Function
- Cell wall formation. Adds enolpyruvyl to UDP-N-acetylglucosamine.
- Specific Function
- UDP-N-acetylglucosamine 1-carboxyvinyltransferase activity
- Gene Name
- murA
- Uniprot ID
- P0A751
- Uniprot Name
- UDP-N-acetylglucosamine 1-carboxyvinyltransferase
- Molecular Weight
- 44817.24 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Catalyzes two distinct but analogous reactions: the reversible epimerization of UDP-glucose to UDP-galactose and the reversible epimerization of UDP-N-acetylglucosamine to UDP-N-acetylgalactosamine. The reaction with UDP-Gal plays a critical role in the Leloir pathway of galactose catabolism in which galactose is converted to the glycolytic intermediate glucose 6-phosphate. It contributes to the catabolism of dietary galactose and enables the endogenous biosynthesis of both UDP-Gal and UDP-GalNAc when exogenous sources are limited. Both UDP-sugar interconversions are important in the synthesis of glycoproteins and glycolipids
- Specific Function
- identical protein binding
- Gene Name
- GALE
- Uniprot ID
- Q14376
- Uniprot Name
- UDP-glucose 4-epimerase
- Molecular Weight
- 38281.435 Da
References
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Involved in the metabolism of galactose. Catalyzes the conversion of UDP-galactose (UDP-Gal) to UDP-glucose (UDP-Glc) through a mechanism involving the transient reduction of NAD. It is only active on UDP-galactose and UDP-glucose.
- Specific Function
- identical protein binding
- Gene Name
- galE
- Uniprot ID
- P09147
- Uniprot Name
- UDP-glucose 4-epimerase
- Molecular Weight
- 37264.875 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Glycosyltransferase required for the biosynthesis of heparan-sulfate and responsible for the alternating addition of beta-1-4-linked glucuronic acid (GlcA) and alpha-1-4-linked N-acetylglucosamine (GlcNAc) units to nascent heparan sulfate chains
- Specific Function
- alpha-1,4-N-acetylgalactosaminyltransferase activity
- Gene Name
- EXTL2
- Uniprot ID
- Q9UBQ6
- Uniprot Name
- Exostosin-like 2
- Molecular Weight
- 37465.365 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Initiates complex N-linked carbohydrate formation. Essential for the conversion of high-mannose to hybrid and complex N-glycans
- Specific Function
- acetylglucosaminyltransferase activity
- Gene Name
- MGAT1
- Uniprot ID
- P26572
- Uniprot Name
- Alpha-1,3-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferase
- Molecular Weight
- 50877.88 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Catalyzes the last two sequential reactions in the de novo biosynthetic pathway for UDP-N-acetylglucosamine (UDP-GlcNAc). The C-terminal domain catalyzes the transfer of acetyl group from acetyl coenzyme A to glucosamine-1-phosphate (GlcN-1-P) to produce N-acetylglucosamine-1-phosphate (GlcNAc-1-P), which is converted into UDP-GlcNAc by the transfer of uridine 5-monophosphate (from uridine 5-triphosphate), a reaction catalyzed by the N-terminal domain.
- Specific Function
- glucosamine-1-phosphate N-acetyltransferase activity
- Gene Name
- glmU
- Uniprot ID
- P0ACC7
- Uniprot Name
- Bifunctional protein GlmU
- Molecular Weight
- 49189.765 Da
References
- Kind
- Protein
- Organism
- Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
- Pharmacological action
- Unknown
- General Function
- Catalyzes the last two sequential reactions in the de novo biosynthetic pathway for UDP-N-acetylglucosamine (UDP-GlcNAc). The C-terminal domain catalyzes the transfer of acetyl group from acetyl coenzyme A to glucosamine-1-phosphate (GlcN-1-P) to produce N-acetylglucosamine-1-phosphate (GlcNAc-1-P), which is converted into UDP-GlcNAc by the transfer of uridine 5-monophosphate (from uridine 5-triphosphate), a reaction catalyzed by the N-terminal domain.
- Specific Function
- glucosamine-1-phosphate N-acetyltransferase activity
- Gene Name
- glmU
- Uniprot ID
- Q97R46
- Uniprot Name
- Bifunctional protein GlmU
- Molecular Weight
- 49344.4 Da
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22