(2R,3R,4R,5S,6R)-6-({[({[(2S,3R,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

• ChemBase ID: 2745
• Molecular Formular: C15H22N2O18P2
• Molecular Mass: 580.285302
• Monoisotopic Mass: 580.03428513
• SMILES: O[C@H]1[C@H](CO[P@](=O)(O)O[P@](=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)n1ccc(=O)[nH]c1=O
• Canonical SMILES: O[C@H]1[C@H](CO[P@@](=O)(O[P@@](=O)(O[C@H]2O[C@@H](C(=O)O)[C@@H]([C@H]([C@@H]2O)O)O)O)O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O
• 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+/m0/s1
• InChIKey: HDYANYHVCAPMJV-USQUEEHTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-({[({[(2S,3R,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
• IUPAC Traditional name: @udp-glucuronic acid
• Synonyms: Udp-Glucuronic Acid

Database IDs

• PubChem SID: 160966193; 46504863
• PubChem CID: 46936562

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.6971143
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): -11.300467
• LogD (pH = 7.4): -12.853949
• Log P: -4.6763334
• Molar Refractivity: 106.3232 cm^3
• Polarizability: 44.32593 Å^3
• Polar Surface Area: 308.61 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.21
• LOG S: -1.51
• Solubility (Water): 1.81e+01 g/l

DETAILS

DrugBank - DB03041

• Drug Groups: experimental
• Description: 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]