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Identification
NameUridine Diphosphate Galactose
Accession NumberDB03501  (EXPT01576)
TypeSmall Molecule
GroupsExperimental
Description

A nucleoside diphosphate sugar which can be epimerized into UDPglucose for entry into the mainstream of carbohydrate metabolism. Serves as a source of galactose in the synthesis of lipopolysaccharides, cerebrosides, and lactose. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
GALACTOSE-URIDINE-5'-DIPHOSPHATENot AvailableNot Available
GDUNot AvailableNot Available
UDP galactoseNot AvailableNot Available
UDP-alpha-d-galactoseNot AvailableNot Available
UDP-D-GalactopyranoseNot AvailableNot Available
UDP-d-galactoseNot AvailableNot Available
UDP-galNot AvailableNot Available
UDP-galactopyranoseNot AvailableNot Available
UDP-galactoseNot AvailableNot Available
UDPgalNot AvailableNot Available
UPGNot AvailableNot Available
Uridine 5'-diphosphate galactoseNot AvailableNot Available
Uridine 5'-diphosphogalactoseNot AvailableNot Available
Uridine diphosphate-d-galactoseNot AvailableNot Available
Uridine diphosphogalactoseNot AvailableNot Available
Uridine pyrophosphogalactoseNot AvailableNot Available
Uridinediphosphate galactoseNot AvailableNot Available
UridinediphosphogalactoseNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number2956-16-3
WeightAverage: 566.3018
Monoisotopic: 566.055020376
Chemical FormulaC15H24N2O17P2
InChI KeyHSCJRCZFDFQWRP-LJMZODOWSA-N
InChI
InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11+,12-,13+,14+/m0/s1
IUPAC Name
[({[(2S,3R,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
SMILES
OC[C@@H]1O[C@H](O[P@](O)(=O)O[P@@](O)(=O)OC[C@@H]2O[C@H]([C@H](O)[C@H]2O)N2C=CC(=O)NC2=O)[C@@H](O)[C@H](O)[C@H]1O
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydropyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Urea
  • Secondary alcohol
  • Polyol
  • Lactam
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9663
Blood Brain Barrier+0.5056
Caco-2 permeable-0.8009
P-glycoprotein substrateNon-substrate0.7431
P-glycoprotein inhibitor INon-inhibitor0.8247
P-glycoprotein inhibitor IINon-inhibitor0.9557
Renal organic cation transporterNon-inhibitor0.9359
CYP450 2C9 substrateNon-substrate0.6584
CYP450 2D6 substrateNon-substrate0.8534
CYP450 3A4 substrateNon-substrate0.5483
CYP450 1A2 substrateNon-inhibitor0.8601
CYP450 2C9 substrateNon-inhibitor0.8605
CYP450 2D6 substrateNon-inhibitor0.8544
CYP450 2C19 substrateNon-inhibitor0.8096
CYP450 3A4 substrateInhibitor0.5
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7607
Ames testNon AMES toxic0.7638
CarcinogenicityNon-carcinogens0.8879
BiodegradationNot ready biodegradable0.5412
Rat acute toxicity2.4144 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9574
hERG inhibition (predictor II)Non-inhibitor0.5158
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility15.0 mg/mLALOGPS
logP-1.4ALOGPS
logP-5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area291.54 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.46 m3·mol-1ChemAxon
Polarizability46.81 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Histo-blood group ABO system transferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Histo-blood group ABO system transferase P16442 Details

References:

  1. Nguyen HP, Seto NO, Cai Y, Leinala EK, Borisova SN, Palcic MM, Evans SV: The influence of an intramolecular hydrogen bond in differential recognition of inhibitory acceptor analogs by human ABO blood group A and B glycosyltransferases. J Biol Chem. 2003 Dec 5;278(49):49191-5. Epub 2003 Sep 11. Pubmed

2. UDP-glucose 4-epimerase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
UDP-glucose 4-epimerase Q14376 Details

References:

  1. Thoden JB, Wohlers TM, Fridovich-Keil JL, Holden HM: Molecular basis for severe epimerase deficiency galactosemia. X-ray structure of the human V94m-substituted UDP-galactose 4-epimerase. J Biol Chem. 2001 Jun 8;276(23):20617-23. Epub 2001 Mar 7. Pubmed

3. Beta-1,4-galactosyltransferase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-1,4-galactosyltransferase 1 P15291 Details

References:

  1. Ramakrishnan B, Balaji PV, Qasba PK: Crystal structure of beta1,4-galactosyltransferase complex with UDP-Gal reveals an oligosaccharide acceptor binding site. J Mol Biol. 2002 Apr 26;318(2):491-502. Pubmed
  2. 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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:21