Uridine-Diphosphate-N-Acetylglucosamine

Identification

Name
Uridine-Diphosphate-N-Acetylglucosamine
Accession Number
DB03397  (EXPT03168)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 607.3537
Monoisotopic: 607.081569477
Chemical Formula
C17H27N3O17P2
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}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UUDP-N-acetylhexosamine pyrophosphorylaseNot AvailableHuman
UUDP-N-acetylglucosamine 1-carboxyvinyltransferaseNot AvailableShigella flexneri
UUDP-glucose 4-epimeraseNot AvailableHuman
UUDP-glucose 4-epimeraseNot AvailableEscherichia coli (strain K12)
UExostosin-like 2Not AvailableHuman
UAlpha-1,3-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferaseNot AvailableHuman
UBifunctional protein GlmUNot AvailableEscherichia coli (strain K12)
UBifunctional protein GlmUNot AvailableStreptococcus 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB00290
KEGG Compound
C00043
PubChem Compound
445675
PubChem Substance
46506870
ChemSpider
393240
ChEBI
16264
HET
UD1
PDB Entries
1foa / 1fwy / 1g97 / 1hm9 / 1hv9 / 1hzj / 1i3m / 1i3n / 1jv1 / 1jvd
show 58 more

Clinical Trials

Clinical Trials
Not Available

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
PropertyValueSource
Water Solubility11.4 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity117.56 m3·mol-1ChemAxon
Polarizability50.35 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9428
Blood Brain Barrier-0.6722
Caco-2 permeable-0.8058
P-glycoprotein substrateNon-substrate0.6736
P-glycoprotein inhibitor INon-inhibitor0.8213
P-glycoprotein inhibitor IINon-inhibitor0.9728
Renal organic cation transporterNon-inhibitor0.9423
CYP450 2C9 substrateNon-substrate0.5768
CYP450 2D6 substrateNon-substrate0.8558
CYP450 3A4 substrateNon-substrate0.5166
CYP450 1A2 substrateNon-inhibitor0.8604
CYP450 2C9 inhibitorNon-inhibitor0.8426
CYP450 2D6 inhibitorNon-inhibitor0.8425
CYP450 2C19 inhibitorNon-inhibitor0.7877
CYP450 3A4 inhibitorInhibitor0.5327
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7107
Ames testNon AMES toxic0.7602
CarcinogenicityNon-carcinogens0.8747
BiodegradationNot ready biodegradable0.6335
Rat acute toxicity2.3962 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9511
hERG inhibition (predictor II)Non-inhibitor0.5183
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (n TMS)GC-MSsplash10-00di-9620000000-18841b4db9b69a91db36
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9620000000-18841b4db9b69a91db36
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0a4i-5543009000-8a176d160a1f074ab319
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, NegativeLC-MS/MSsplash10-05cr-4796000000-6c09aa3a2dac66281973
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-5543009000-8a176d160a1f074ab319
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-05cr-4796000000-6c09aa3a2dac66281973
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
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
show 32 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
UDP-amino sugar (CHEBI:16264)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Udp-n-acetylglucosamine diphosphorylase activity
Specific Function
Converts UDP and GlcNAc-1-P into UDP-GlcNAc, and UDP and GalNAc-1-P into UDP-GalNAc. Isoform AGX1 has 2 to 3 times higher activity towards GalNAc-1-P, while isoform AGX2 has 8 times more activity t...
Gene Name
UAP1
Uniprot ID
Q16222
Uniprot Name
UDP-N-acetylhexosamine pyrophosphorylase
Molecular Weight
58768.705 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Udp-n-acetylglucosamine 4-epimerase activity
Specific 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...
Gene Name
GALE
Uniprot ID
Q14376
Uniprot Name
UDP-glucose 4-epimerase
Molecular Weight
38281.435 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Udp-glucose 4-epimerase activity
Specific 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...
Gene Name
galE
Uniprot ID
P09147
Uniprot Name
UDP-glucose 4-epimerase
Molecular Weight
37264.875 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific 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 ...
Gene Name
EXTL2
Uniprot ID
Q9UBQ6
Uniprot Name
Exostosin-like 2
Molecular Weight
37465.365 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
  3. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Initiates complex N-linked carbohydrate formation. Essential for the conversion of high-mannose to hybrid and complex N-glycans.
Gene Name
MGAT1
Uniprot ID
P26572
Uniprot Name
Alpha-1,3-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferase
Molecular Weight
50877.88 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
  3. 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. [PubMed:10592235]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Udp-n-acetylglucosamine diphosphorylase activity
Specific 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 co...
Gene Name
glmU
Uniprot ID
P0ACC7
Uniprot Name
Bifunctional protein GlmU
Molecular Weight
49189.765 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Unknown
General Function
Udp-n-acetylglucosamine diphosphorylase activity
Specific 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 co...
Gene Name
glmU
Uniprot ID
Q97R46
Uniprot Name
Bifunctional protein GlmU
Molecular Weight
49344.4 Da

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:27