[({[(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,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

• ChemBase ID: 130100
• Molecular Formular: C15H24N2O17P2
• Molecular Mass: 566.301782
• Monoisotopic Mass: 566.05502058
• SMILES: O=P(O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(=O)[nH]c2=O)[C@H](O)[C@@H]1O
• Canonical SMILES: OC[C@H]1O[C@H](OP(=O)(OP(=O)(OC[C@H]2O[C@H]([C@@H]([C@@H]2O)O)n2ccc(=O)[nH]c2=O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
• 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
• InChIKey: HSCJRCZFDFQWRP-JZMIEXBBSA-N

NAMES AND DATABASE IDS

Names

• 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,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
• IUPAC Traditional name: udp-α-D-glucose
• Synonyms: UDP-glucose; Uridine diphosphate glucose

Database IDs

• CAS Number: 133-89-1
• PubChem SID: 162224385
• PubChem CID: 8629
• CHEBI ID: 52249
• CHEMBL: 375951
• Chemspider ID: 8308
• IUPHAR ligand ID: 1783
• MeSH Name: Uridine+Diphosphate+Glucose
• Wikipedia Title: Uridine_diphosphate_glucose

CALCULATED PROPERTIES

• Acid pKa: 1.7326003
• H Acceptors: 14
• H Donor: 9
• LogD (pH = 5.5): -9.414037
• LogD (pH = 7.4): -9.745448
• Log P: -4.9966083
• Molar Refractivity: 106.4558 cm^3
• Polarizability: 44.259937 Å^3
• Polar Surface Area: 291.54 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false