Uridine-Diphosphate-N-Acetylgalactosamine

Identification

Name
Uridine-Diphosphate-N-Acetylgalactosamine
Accession Number
DB02196  (EXPT03169)
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-NESSUJCYSA-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,5R,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-glucose 4-epimeraseNot AvailableHuman
UUDP-N-acetylglucosamine 2-epimeraseNot AvailableEscherichia coli (strain K12)
UHisto-blood group ABO system transferaseNot AvailableHuman
UUDP-N-acetylglucosamine--N-acetylmuramyl-(pentapeptide) pyrophosphoryl-undecaprenol N-acetylglucosamine transferaseNot AvailableEscherichia coli (strain K12)
UExostosin-like 2Not AvailableHuman
UWbpPNot AvailablePseudomonas aeruginosa
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
HMDB60522
PubChem Compound
23700
PubChem Substance
46508676
ChemSpider
22161
ChEBI
67168
HET
UD2
PDB Entries
1jv3 / 1jvg / 1omz / 1oqm / 1r81 / 1sb8 / 2z87 / 3lu1 / 3ruc / 3swi
show 3 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
Polarizability51.05 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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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-5332109000-51407a00f408770ec019
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-05cr-5796100000-28a7cdf50cd872a70c19
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udr-1960000000-6ceaa442b144ea3c15f7

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-N-acetyl-D-galactosamine (CHEBI:67168)

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
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-n-acetylglucosamine 2-epimerase activity
Specific Function
Catalyzes the reversible epimerization at C-2 of UDP-N-acetylglucosamine (UDP-GlcNAc) and thereby provides bacteria with UDP-N-acetylmannosamine (UDP-ManNAc), the activated donor of ManNAc residues...
Gene Name
wecB
Uniprot ID
P27828
Uniprot Name
UDP-N-acetylglucosamine 2-epimerase
Molecular Weight
42244.235 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
This protein is the basis of the ABO blood group system. The histo-blood group ABO involves three carbohydrate antigens: A, B, and H. A, B, and AB individuals express a glycosyltransferase activity...
Gene Name
ABO
Uniprot ID
P16442
Uniprot Name
Histo-blood group ABO system transferase
Molecular Weight
40933.555 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
Undecaprenyldiphospho-muramoylpentapeptide beta-n-acetylglucosaminyltransferase activity
Specific Function
Cell wall formation. Catalyzes the transfer of a GlcNAc subunit on undecaprenyl-pyrophosphoryl-MurNAc-pentapeptide (lipid intermediate I) to form undecaprenyl-pyrophosphoryl-MurNAc-(pentapeptide)Gl...
Gene Name
murG
Uniprot ID
P17443
Uniprot Name
UDP-N-acetylglucosamine--N-acetylmuramyl-(pentapeptide) pyrophosphoryl-undecaprenol N-acetylglucosamine transferase
Molecular Weight
37814.49 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
Pseudomonas aeruginosa
Pharmacological action
Unknown
General Function
Racemase and epimerase activity, acting on carbohydrates and derivatives
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q8KN66
Uniprot Name
WbpP
Molecular Weight
37748.31 Da

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:11