{[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2,4-dihydroxy-3,3-dimethylbutanoyl]oxy})phosphinic acid

• ChemBase ID: 2418
• Molecular Formular: C16H24N5O10P
• Molecular Mass: 477.363021
• Monoisotopic Mass: 477.12607862
• SMILES: CC(C)(CO)[C@@H](O)C(=O)O[P@](=O)(O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1O)n1cnc2c1ncnc2N
• Canonical SMILES: OCC([C@H](C(=O)O[P@@](=O)(OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1cnc2c1ncnc2N)O)O)(C)C
• InChI: InChI=1S/C16H24N5O10P/c1-16(2,4-22)11(25)15(26)31-32(27,28)29-3-7-9(23)10(24)14(30-7)21-6-20-8-12(17)18-5-19-13(8)21/h5-7,9-11,14,22-25H,3-4H2,1-2H3,(H,27,28)(H2,17,18,19)/t7-,9-,10+,11-,14+/m0/s1
• InChIKey: GDPVENOGSVMRJL-NPPWWWSGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2,4-dihydroxy-3,3-dimethylbutanoyl]oxy})phosphinic acid
• IUPAC Traditional name: @pantoyl adenylate
• Synonyms: Pantoyl Adenylate

Database IDs

• PubChem SID: 46507479; 160965869
• PubChem CID: 46936457

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.760317
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -4.7650986
• LogD (pH = 7.4): -4.7126956
• Log P: -4.92437
• Molar Refractivity: 104.5845 cm^3
• Polarizability: 41.737602 Å^3
• Polar Surface Area: 232.6 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.84
• LOG S: -2.21
• Solubility (Water): 2.93e+00 g/l

DETAILS

DrugBank - DB02694

Drug information: experimental