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

• ChemBase ID: 2927
• Molecular Formular: C13H20N5O7P
• Molecular Mass: 389.300961
• Monoisotopic Mass: 389.11003464
• SMILES: CCCO[P@](=O)(O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1O)n1cnc2c1ncnc2N
• Canonical SMILES: CCCO[P@@](=O)(OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1cnc2c1ncnc2N)O
• InChI: InChI=1S/C13H20N5O7P/c1-2-3-23-26(21,22)24-4-7-9(19)10(20)13(25-7)18-6-17-8-11(14)15-5-16-12(8)18/h5-7,9-10,13,19-20H,2-4H2,1H3,(H,21,22)(H2,14,15,16)/t7-,9-,10+,13+/m0/s1
• InChIKey: XAMXMSZRQHPMRX-UFAOYGAJSA-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}(propoxy)phosphinic acid
• IUPAC Traditional name: @adenosine-5'-propylphosphate
• Synonyms: Adenosine-5'-Propylphosphate

Database IDs

• PubChem SID: 160966374; 46507162
• PubChem CID: 46936616

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8545512
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -3.3672853
• LogD (pH = 7.4): -3.3342192
• Log P: -3.436389
• Molar Refractivity: 87.8234 cm^3
• Polarizability: 34.73078 Å^3
• Polar Surface Area: 175.07 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.41
• LOG S: -2.12
• Solubility (Water): 2.98e+00 g/l

DETAILS

DrugBank - DB03230

Drug information: experimental