{[(2R,3S)-4-({[({[(2S,3R,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,3-dihydroxy-2-methylbutan-2-yl]oxy}phosphonic acid

• ChemBase ID: 1629
• Molecular Formular: C14H26N3O17P3
• Molecular Mass: 601.287423
• Monoisotopic Mass: 601.04750628
• SMILES: C[C@](CO)(OP(=O)(O)O)[C@@H](O)CO[P@@](=O)(O)O[P@](=O)(O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1O)n1ccc(N)nc1=O
• Canonical SMILES: OC[C@]([C@H](CO[P@](=O)(O[P@@](=O)(OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1ccc(nc1=O)N)O)O)O)(OP(=O)(O)O)C
• InChI: InChI=1S/C14H26N3O17P3/c1-14(6-18,33-35(23,24)25)8(19)5-31-37(28,29)34-36(26,27)30-4-7-10(20)11(21)12(32-7)17-3-2-9(15)16-13(17)22/h2-3,7-8,10-12,18-21H,4-6H2,1H3,(H,26,27)(H,28,29)(H2,15,16,22)(H2,23,24,25)/t7-,8-,10-,11+,12+,14+/m0/s1
• InChIKey: HTJXTKBIUVFUAR-GSNOWDBKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S)-4-({[({[(2S,3R,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,3-dihydroxy-2-methylbutan-2-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2R,3S)-4-[({[(2S,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-1,3-dihydroxy-2-methylbutan-2-yl]oxyphosphonic acid
• Synonyms: 4-Diphosphocytidyl-2-C-Methyl-D-Erythritol 2-Phosphate

Database IDs

• PubChem SID: 46506614; 160965086
• PubChem CID: 46936241

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2245817
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): -11.585956
• LogD (pH = 7.4): -13.099933
• Log P: -5.2437644
• Molar Refractivity: 114.5013 cm^3
• Polarizability: 46.820854 Å^3
• Polar Surface Area: 317.89 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.88
• LOG S: -1.6
• Solubility (Water): 1.51e+01 g/l

DETAILS

DrugBank - DB01859

Drug information: experimental