Identification
- Generic Name
- Galactose-uridine-5'-diphosphate
- DrugBank Accession Number
- DB03501
- Background
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.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Galactose-uridine-5'-diphosphate (DB03501)
- Weight
- Average: 566.3018
Monoisotopic: 566.055020376 - Chemical Formula
- C15H24N2O17P2
- 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
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UHisto-blood group ABO system transferase Not Available Humans UUDP-glucose 4-epimerase Not Available Humans UBeta-1,4-galactosyltransferase 1 Not Available Humans UUracil nucleotide/cysteinyl leukotriene receptor regulatorHumans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
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
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Alcohol / Alkyl phosphate / Aromatic heteromonocyclic compound / Azacycle / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Hydroxypyrimidine / Monoalkyl phosphate show 25 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- UDP-D-galactose (CHEBI:67119)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- O2HY4WY2W1
- CAS number
- 2956-16-3
- 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({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000302
- KEGG Compound
- C00052
- PubChem Compound
- 18068
- PubChem Substance
- 46507114
- ChemSpider
- 17069
- BindingDB
- 50209668
- ChEBI
- 67119
- ChEMBL
- CHEMBL439009
- ZINC
- ZINC000008551104
- PDBe Ligand
- GDU
- PDB Entries
- 1fr8 / 1gup / 1i3l / 1o0r / 1r82 / 1tvy / 1tw1 / 1yro / 2fyc / 2gna … show 33 more
Clinical Trials
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
Property Value Source Water Solubility 15.0 mg/mL ALOGPS logP -1.4 ALOGPS logP -5 Chemaxon logS -1.6 ALOGPS pKa (Strongest Acidic) 1.73 Chemaxon pKa (Strongest Basic) -3.6 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 14 Chemaxon Hydrogen Donor Count 9 Chemaxon Polar Surface Area 291.54 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 106.46 m3·mol-1 Chemaxon Polarizability 45.93 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9663 Blood Brain Barrier + 0.5056 Caco-2 permeable - 0.8009 P-glycoprotein substrate Non-substrate 0.7431 P-glycoprotein inhibitor I Non-inhibitor 0.8247 P-glycoprotein inhibitor II Non-inhibitor 0.9557 Renal organic cation transporter Non-inhibitor 0.9359 CYP450 2C9 substrate Non-substrate 0.6584 CYP450 2D6 substrate Non-substrate 0.8534 CYP450 3A4 substrate Non-substrate 0.5483 CYP450 1A2 substrate Non-inhibitor 0.8601 CYP450 2C9 inhibitor Non-inhibitor 0.8605 CYP450 2D6 inhibitor Non-inhibitor 0.8544 CYP450 2C19 inhibitor Non-inhibitor 0.8096 CYP450 3A4 inhibitor Inhibitor 0.5 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7607 Ames test Non AMES toxic 0.7638 Carcinogenicity Non-carcinogens 0.8879 Biodegradation Not ready biodegradable 0.5412 Rat acute toxicity 2.4144 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9574 hERG inhibition (predictor II) Non-inhibitor 0.5158
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative LC-MS/MS splash10-0100-9428070000-ad4101fafd847dad3677 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available 1H NMR Spectrum 1D NMR Not Applicable [1H,13C] 2D NMR Spectrum 2D NMR Not Applicable
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Regulator
- General Function
- Dual specificity receptor for uracil nucleotides and cysteinyl leukotrienes (CysLTs). Signals through G(i) and inhibition of adenylyl cyclase. May mediate brain damage by nucleotides and CysLTs following ischemia.
- Specific Function
- Chemokine receptor activity
- Gene Name
- GPR17
- Uniprot ID
- Q13304
- Uniprot Name
- Uracil nucleotide/cysteinyl leukotriene receptor
- Molecular Weight
- 40988.99 Da
References
- Marucci G, Dal Ben D, Lambertucci C, Santinelli C, Spinaci A, Thomas A, Volpini R, Buccioni M: The G Protein-Coupled Receptor GPR17: Overview and Update. ChemMedChem. 2016 Dec 6;11(23):2567-2574. doi: 10.1002/cmdc.201600453. Epub 2016 Nov 14. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52