UDP-alpha-D-xylose

Identification

Name
UDP-alpha-D-xylose
Accession Number
DB01713  (EXPT03173)
Type
Small Molecule
Groups
Experimental
Description

The decarboxylation product of UDPglucuronic acid, which is used for formation of the xylosides of seryl hydroxyl groups in mucoprotein synthesis. Also forms plant xylans.

Structure
Thumb
Synonyms
  • UDP-xylose
  • Uridine-5'-diphosphate-xylopyranose
Categories
Not Available
UNII
Not Available
CAS number
3616-06-6
Weight
Average: 536.2758
Monoisotopic: 536.04445569
Chemical Formula
C14H22N2O16P2
InChI Key
DQQDLYVHOTZLOR-OCIMBMBZSA-N
InChI
InChI=1S/C14H22N2O16P2/c17-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)16-2-1-7(18)15-14(16)23/h1-2,5-6,8-13,17,19-22H,3-4H2,(H,24,25)(H,26,27)(H,15,18,23)/t5-,6-,8+,9-,10-,11-,12-,13-/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({[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid
SMILES
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2OC[C@@H](O)[C@H](O)[C@H]2O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UUDP-glucose 6-dehydrogenaseNot AvailableStreptococcus pyogenes
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
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

References

General References
Not Available
External Links
PubChem Compound
19235
PubChem Substance
46508749
ChemSpider
18152
ChEBI
16082
ZINC
ZINC000008551129
PDBe Ligand
UDX
PDB Entries
1dli / 3prj / 3ptz / 4wnh / 5ux7 / 5vr8 / 6c58 / 6ej7 / 6kvj / 6om8

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 Solubility13.6 mg/mLALOGPS
logP-1.3ALOGPS
logP-4.4ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area271.31 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity100.49 m3·mol-1ChemAxon
Polarizability42.12 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9734
Blood Brain Barrier-0.6363
Caco-2 permeable-0.7969
P-glycoprotein substrateNon-substrate0.6773
P-glycoprotein inhibitor INon-inhibitor0.7846
P-glycoprotein inhibitor IINon-inhibitor0.9495
Renal organic cation transporterNon-inhibitor0.9462
CYP450 2C9 substrateNon-substrate0.6781
CYP450 2D6 substrateNon-substrate0.8531
CYP450 3A4 substrateNon-substrate0.5325
CYP450 1A2 substrateNon-inhibitor0.8602
CYP450 2C9 inhibitorNon-inhibitor0.8619
CYP450 2D6 inhibitorNon-inhibitor0.8559
CYP450 2C19 inhibitorNon-inhibitor0.8138
CYP450 3A4 inhibitorNon-inhibitor0.5592
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8115
Ames testNon AMES toxic0.7786
CarcinogenicityNon-carcinogens0.8941
BiodegradationNot ready biodegradable0.6101
Rat acute toxicity2.3521 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9692
hERG inhibition (predictor II)Non-inhibitor0.5268
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 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

Taxonomy

Description
This compound belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine ribonucleotides
Direct Parent
Pyrimidine ribonucleoside diphosphates
Alternative Parents
Pentose phosphates / Glycosylamines / Monosaccharide phosphates / Organic pyrophosphates / Hydroxypyrimidines / Pyrimidones / Monoalkyl phosphates / Hydropyrimidines / Oxanes / Tetrahydrofurans
show 9 more
Substituents
Pyrimidine ribonucleoside diphosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / Monosaccharide phosphate / Organic pyrophosphate / Monoalkyl phosphate / Pyrimidone / Hydroxypyrimidine
show 23 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
UDP-sugar (CHEBI:16082)

Targets

Kind
Protein
Organism
Streptococcus pyogenes
Pharmacological action
Unknown
General Function
Udp-glucose 6-dehydrogenase activity
Specific Function
Catalyzes the formation of UDP-glucuronic acid which is required for capsular hyaluronic acid synthesis.
Gene Name
hasB
Uniprot ID
P0C0F4
Uniprot Name
UDP-glucose 6-dehydrogenase
Molecular Weight
45482.795 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]

Drug created on June 13, 2005 07:24 / Updated on March 01, 2020 18:45

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