(2R,4R,5S,6R)-2-[({[(2S,3R,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-6-[(1S)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylic acid

• ChemBase ID: 4058
• Molecular Formular: C17H26N3O15P
• Molecular Mass: 543.373201
• Monoisotopic Mass: 543.11015378
• SMILES: Nc1nc(=O)n(cc1)[C@@H]1O[C@@H](CO[P@@](=O)(O)O[C@]2(C[C@@H](O)[C@H](O)[C@H](O2)[C@@H](O)CO)C(=O)O)[C@H](O)[C@H]1O
• Canonical SMILES: OC[C@@H]([C@H]1O[C@](C[C@H]([C@@H]1O)O)(O[P@@](=O)(OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1ccc(nc1=O)N)O)C(=O)O)O
• InChI: InChI=1S/C17H26N3O15P/c18-9-1-2-20(16(29)19-9)14-12(26)11(25)8(33-14)5-32-36(30,31)35-17(15(27)28)3-6(22)10(24)13(34-17)7(23)4-21/h1-2,6-8,10-14,21-26H,3-5H2,(H,27,28)(H,30,31)(H2,18,19,29)/t6-,7+,8+,10+,11+,12-,13-,14-,17-/m1/s1
• InChIKey: YWWJKULNWGRYAS-QBDUXVKASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5S,6R)-2-[({[(2S,3R,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-6-[(1S)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,4R,5S,6R)-2-({[(2S,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-6-[(1S)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylic acid
• Synonyms: Cmp-2-Keto-3-Deoxy-Octulosonic Acid

Database IDs

• PubChem SID: 160967492; 46506999
• PubChem CID: 46936984

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.5281283
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): -9.609999
• LogD (pH = 7.4): -10.53392
• Log P: -4.945771
• Molar Refractivity: 108.3563 cm^3
• Polarizability: 44.3933 Å^3
• Polar Surface Area: 291.59 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.75
• LOG S: -1.04
• Solubility (Water): 4.96e+01 g/l

DETAILS

DrugBank - DB04482

Drug information: experimental