UDP-alpha-D-glucuronic acid
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Identification
- Generic Name
- UDP-alpha-D-glucuronic acid
- DrugBank Accession Number
- DB03041
- Background
A nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP iduronic acid, which donates iduronic acid to polysaccharides. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones. [PubChem]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 580.2853
Monoisotopic: 580.034284934 - Chemical Formula
- C15H22N2O18P2
- Synonyms
- UDP-alpha-D-glucuronate
- UDP-D-glucuronate
- UDP-glucuronate
- UDP-Glucuronic Acid
- UDPglucuronate
- uridine diphosphate glucuronic acid
- Uridine-5'-diphosphate-glucuronic acid
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UUDP-glucose 4-epimerase substrateHumans UGalactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 3 Not Available Humans UUDP-glucose 6-dehydrogenase Not Available Streptococcus 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
- 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 / Glucuronic acid derivatives / Glycosylamines / Monosaccharide phosphates / Organic pyrophosphates / Beta hydroxy acids and derivatives / Monoalkyl phosphates / Pyrimidones / Hydropyrimidines show 18 more
- Substituents
- Alcohol / Alkyl phosphate / Aromatic heteromonocyclic compound / Azacycle / Beta-hydroxy acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Glucuronic acid or derivatives / Glycosyl compound show 34 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- UDP-sugar (CHEBI:17200)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 04SZC4MEFQ
- CAS number
- 2616-64-0
- InChI Key
- HDYANYHVCAPMJV-LXQIFKJMSA-N
- InChI
- InChI=1S/C15H22N2O18P2/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26)/t4-,6-,7+,8+,9-,10-,11+,12-,14-/m1/s1
- IUPAC Name
- (2S,3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
- SMILES
- O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000935
- KEGG Compound
- C00167
- PubChem Compound
- 17473
- PubChem Substance
- 46504863
- ChemSpider
- 16522
- BindingDB
- 50209665
- ChEBI
- 17200
- ChEMBL
- CHEMBL228057
- ZINC
- ZINC000008215691
- PDBe Ligand
- UGA
- Wikipedia
- Uridine_diphosphate_glucuronic_acid
- PDB Entries
- 1dlj / 1kws / 1z7e / 2qg4 / 2y0c / 2y0d / 2y0e / 2z86 / 3gg2 / 3pjg … show 8 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 18.1 mg/mL ALOGPS logP -1.2 ALOGPS logP -4.7 Chemaxon logS -1.5 ALOGPS pKa (Strongest Acidic) 1.72 Chemaxon pKa (Strongest Basic) -3.7 Chemaxon Physiological Charge -3 Chemaxon Hydrogen Acceptor Count 15 Chemaxon Hydrogen Donor Count 9 Chemaxon Polar Surface Area 308.61 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 106.32 m3·mol-1 Chemaxon Polarizability 45.33 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 - 0.9675 Blood Brain Barrier + 0.522 Caco-2 permeable - 0.8251 P-glycoprotein substrate Non-substrate 0.7638 P-glycoprotein inhibitor I Non-inhibitor 0.8023 P-glycoprotein inhibitor II Non-inhibitor 0.9441 Renal organic cation transporter Non-inhibitor 0.9396 CYP450 2C9 substrate Non-substrate 0.6646 CYP450 2D6 substrate Non-substrate 0.8589 CYP450 3A4 substrate Non-substrate 0.5312 CYP450 1A2 substrate Non-inhibitor 0.867 CYP450 2C9 inhibitor Non-inhibitor 0.8764 CYP450 2D6 inhibitor Non-inhibitor 0.8742 CYP450 2C19 inhibitor Non-inhibitor 0.8316 CYP450 3A4 inhibitor Non-inhibitor 0.7204 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8237 Ames test Non AMES toxic 0.8575 Carcinogenicity Non-carcinogens 0.9131 Biodegradation Not ready biodegradable 0.5835 Rat acute toxicity 2.3361 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9732 hERG inhibition (predictor II) Non-inhibitor 0.6161
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0w29-3322930000-0ce18416678ea80bec67 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0gx0-0000390000-c05a292a06352df88e51 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0000190000-57922756e57a6d5f8d25 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0ik9-0211950000-67e4e0740d4bbd5805ea Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00n0-2001390000-4f2d9df8d00701a731d5 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-2933810000-30ef4bf5d4d99f61b39b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a59-7615960000-04f5eab22664749ad4b0 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 233.6016812 predictedDarkChem Lite v0.1.0 [M-H]- 238.3393812 predictedDarkChem Lite v0.1.0 [M-H]- 236.1036812 predictedDarkChem Lite v0.1.0 [M-H]- 214.6184 predictedDeepCCS 1.0 (2019) [M+H]+ 235.8395812 predictedDarkChem Lite v0.1.0 [M+H]+ 242.3083812 predictedDarkChem Lite v0.1.0 [M+H]+ 239.3626812 predictedDarkChem Lite v0.1.0 [M+H]+ 216.3421 predictedDeepCCS 1.0 (2019) [M+Na]+ 234.6653812 predictedDarkChem Lite v0.1.0 [M+Na]+ 239.3127812 predictedDarkChem Lite v0.1.0 [M+Na]+ 235.5726812 predictedDarkChem Lite v0.1.0 [M+Na]+ 222.67105 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsUDP-glucose 4-epimerase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Bhatia C, Oerum S, Bray J, Kavanagh KL, Shafqat N, Yue W, Oppermann U: Towards a systematic analysis of human short-chain dehydrogenases/reductases (SDR): Ligand identification and structure-activity relationships. Chem Biol Interact. 2015 Jun 5;234:114-25. doi: 10.1016/j.cbi.2014.12.013. Epub 2014 Dec 16. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein phosphatase activator activity
- Specific Function
- Glycosaminoglycans biosynthesis. Involved in forming the linkage tetrasaccharide present in heparan sulfate and chondroitin sulfate. Transfers a glucuronic acid moiety from the uridine diphosphate-...
- Gene Name
- B3GAT3
- Uniprot ID
- O94766
- Uniprot Name
- Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 3
- Molecular Weight
- 37121.52 Da
References
3. DetailsUDP-glucose 6-dehydrogenase
- 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
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52