{[hydroxy({[(2R,3S,5S)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}({[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid

• ChemBase ID: 3375
• Molecular Formular: C16H26N2O15P2
• Molecular Mass: 548.329562
• Monoisotopic Mass: 548.0808414
• SMILES: C[C@@H]1O[C@H](O[P@@](=O)(O)O[P@](=O)(O)OC[C@H]2O[C@@H](C[C@@H]2O)n2cc(C)c(=O)[nH]c2=O)[C@@H](O)[C@H](O)[C@H]1O
• Canonical SMILES: O[C@H]1C[C@H](O[C@@H]1CO[P@](=O)(O[P@@](=O)(O[C@H]1O[C@@H](C)[C@@H]([C@H]([C@@H]1O)O)O)O)O)n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C16H26N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-13,15,19-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/t7-,8-,9+,10-,11-,12+,13-,15+/m0/s1
• InChIKey: ZOSQFDVXNQFKBY-UTCAIGHUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[hydroxy({[(2R,3S,5S)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}({[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid
• IUPAC Traditional name: {hydroxy[(2R,3S,5S)-3-hydroxy-5-(5-methyl-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methoxyphosphoryl}oxy[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphinic acid
• Synonyms: 2'-Deoxy-Thymidine-Beta-L-Rhamnose

Database IDs

• PubChem SID: 160966816; 46505764
• PubChem CID: 46936769

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.712614
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -7.0819197
• LogD (pH = 7.4): -7.40166
• Log P: -2.6535096
• Molar Refractivity: 107.7585 cm^3
• Polarizability: 44.5805 Å^3
• Polar Surface Area: 251.08 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.09
• LOG S: -1.68
• Solubility (Water): 1.16e+01 g/l

DETAILS

DrugBank - DB03723

Drug information: experimental