[({[(2S,3R,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy})phosphinic acid

• ChemBase ID: 1487
• Molecular Formular: C14H22N2O16P2
• Molecular Mass: 536.275802
• Monoisotopic Mass: 536.04445589
• SMILES: O[C@H]1CO[C@@H](O[P@@](=O)(O)O[P@](=O)(O)OC[C@@H]2O[C@H]([C@H](O)[C@H]2O)n2ccc(=O)[nH]c2=O)[C@H](O)[C@H]1O
• Canonical SMILES: O[C@H]1[C@H](CO[P@](=O)(O[P@@](=O)(O[C@@H]2OC[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/C14H22N2O16P2/c17-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)16-2-1-7(18)15-14(16)23/h1-2,5-6,8-13,17,19-22H,3-4H2,(H,24,25)(H,26,27)(H,15,18,23)/t5-,6-,8-,9-,10+,11+,12+,13-/m0/s1
• InChIKey: DQQDLYVHOTZLOR-NNFAFSNNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[(2S,3R,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy})phosphinic acid
• IUPAC Traditional name: {[(2S,3R,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyphosphinic acid
• Synonyms: Udp-Alpha-D-Xylopyranose

Database IDs

• PubChem SID: 46508749; 160964946
• PubChem CID: 46936197

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7126523
• H Acceptors: 13
• H Donor: 8
• LogD (pH = 5.5): -8.794685
• LogD (pH = 7.4): -9.115385
• Log P: -4.366273
• Molar Refractivity: 100.4933 cm^3
• Polarizability: 41.74576 Å^3
• Polar Surface Area: 271.31 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.3
• LOG S: -1.6
• Solubility (Water): 1.36e+01 g/l

DETAILS

DrugBank - DB01713

• Drug Groups: experimental
• Description: The decarboxylation product of UDPglucuronic acid, which is used for formation of the xylosides of seryl hydroxyl groups in mucoprotein synthesis. Also forms plant xylans. [PubChem]