(2S,4aR,6S,7S,7aR)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2$l^{5}-furo[3,2-d][1,3,2$l^{5}]dioxaphosphinine-2-thione

• ChemBase ID: 1561
• Molecular Formular: C10H12N5O5PS
• Molecular Mass: 345.271541
• Monoisotopic Mass: 345.02967614
• SMILES: Nc1ncnc2c1ncn2[C@H]1O[C@@H]2CO[P@@](=S)(O)O[C@@H]2[C@@H]1O
• Canonical SMILES: O[C@H]1[C@H]2O[P@](=S)(O)OC[C@H]2O[C@@H]1n1cnc2c1ncnc2N
• InChI: InChI=1S/C10H12N5O5PS/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(19-10)1-18-21(17,22)20-7/h2-4,6-7,10,16H,1H2,(H,17,22)(H2,11,12,13)/t4-,6+,7+,10+,21+/m1/s1
• InChIKey: SMPNJFHAPJOHPP-BTQOAJACSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4aR,6S,7S,7aR)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2$l^{5}-furo[3,2-d][1,3,2$l^{5}]dioxaphosphinine-2-thione
• IUPAC Traditional name: (2S,4aR,6S,7S,7aR)-6-(6-aminopurin-9-yl)-2,7-dihydroxy-tetrahydro-4H-1,3,5,2$l^{5}-furo[3,2-d][1,3,2$l^{5}]dioxaphosphinine-2-thione
• Synonyms: Sp-Adenosine-3',5'-Cyclic-Monophosphorothioate

Database IDs

• PubChem SID: 160965018; 46504971
• PubChem CID: 46936216

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8330745
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.8393102
• LogD (pH = 7.4): -2.8051202
• Log P: -2.913026
• Molar Refractivity: 78.2804 cm^3
• Polarizability: 31.14115 Å^3
• Polar Surface Area: 137.77 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.93
• LOG S: -2.27
• Solubility (Water): 1.84e+00 g/l

DETAILS

DrugBank - DB01790

Drug information: experimental