Galactose-uridine-5'-diphosphate

Identification

Name
Galactose-uridine-5'-diphosphate
Accession Number
DB03501  (EXPT01576)
Type
Small Molecule
Groups
Experimental
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.

Structure
Thumb
Synonyms
  • UDP galactose
  • UDP-alpha-D-galactose
  • UDP-D-galactopyranose
  • UDP-galactose
  • UDP-α-D-galactopyranose
  • UDP-α-D-galactose
  • UDPgal
  • Uridine diphosphate galactose
  • Uridine diphosphategalactose
  • Uridine diphosphogalactose
  • Uridine pyrophosphogalactose
  • Uridinediphosphogalactose
Categories
UNII
Not Available
CAS number
2956-16-3
Weight
Average: 566.3018
Monoisotopic: 566.055020376
Chemical Formula
C15H24N2O17P2
InChI Key
HSCJRCZFDFQWRP-ABVWGUQPSA-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-/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,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHisto-blood group ABO system transferaseNot AvailableHuman
UUDP-glucose 4-epimeraseNot AvailableHuman
UBeta-1,4-galactosyltransferase 1Not AvailableHuman
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
  • Humans and other mammals
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
HMDB00302
KEGG Compound
C00052
PubChem Compound
18068
PubChem Substance
46507114
ChemSpider
17069
BindingDB
50209668
ChEBI
67119
ChEMBL
CHEMBL439009
HET
GDU
PDB Entries
1fr8 / 1gup / 1i3l / 1o0r / 1r82 / 1tvy / 1tw1 / 1yro / 2fyc / 2gna
show 24 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 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
Polarizability45.05 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9663
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 inhibitorNon-inhibitor0.8605
CYP450 2D6 inhibitorNon-inhibitor0.8544
CYP450 2C19 inhibitorNon-inhibitor0.8096
CYP450 3A4 inhibitorInhibitor0.5
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
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
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0100-9428070000-ad4101fafd847dad3677
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
1H NMR Spectrum1D 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 / Glycosylamines / Organic pyrophosphates / Monosaccharide phosphates / Pyrimidones / Hydroxypyrimidines / Monoalkyl phosphates / Oxanes / Hydropyrimidines
show 11 more
Substituents
Pyrimidine nucleotide sugar / Pyrimidine ribonucleoside diphosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / Monosaccharide phosphate / Organic pyrophosphate / Hydroxypyrimidine / Pyrimidone
show 25 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
UDP-D-galactose (CHEBI:67119)

Targets

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. 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(H) blood group A and B glycosyltransferases. J Biol Chem. 2003 Dec 5;278(49):49191-5. Epub 2003 Sep 11. [PubMed:12972418]
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. 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:11279193]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Udp-galactosyltransferase activity
Specific Function
The Golgi complex form catalyzes the production of lactose in the lactating mammary gland and could also be responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoprot...
Gene Name
B4GALT1
Uniprot ID
P15291
Uniprot Name
Beta-1,4-galactosyltransferase 1
Molecular Weight
43919.895 Da
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:12051854]
  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:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:29