(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-{[(R)-[2-(aminooxy)ethyl](methyl)sulfaniumyl]methyl}oxolane-3,4-diol

• ChemBase ID: 2255
• Molecular Formular: C13H21N6O4S+
• Molecular Mass: 357.40864
• Monoisotopic Mass: 357.13449918
• SMILES: C[S@+](CCON)C[C@@H]1O[C@H]([C@H](O)[C@H]1O)n1cnc2c1ncnc2N
• Canonical SMILES: NOCC[S@+](C[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1cnc2c1ncnc2N)C
• InChI: InChI=1S/C13H21N6O4S/c1-24(3-2-22-15)4-7-9(20)10(21)13(23-7)19-6-18-8-11(14)16-5-17-12(8)19/h5-7,9-10,13,20-21H,2-4,15H2,1H3,(H2,14,16,17)/q+1/t7-,9-,10+,13+,24+/m0/s1
• InChIKey: RMAOLICYOBWFLA-ZTXHCXIGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-{[(R)-[2-(aminooxy)ethyl](methyl)sulfaniumyl]methyl}oxolane-3,4-diol
• IUPAC Traditional name: AAD
• Synonyms: [2-(AMINO-OXY)ETHYL](5'-DEOXYADENOSIN-5'-YL)(METHYL)SULFONIUM; (2-AMINOOXY-ETHYL)-[5-(6-AMINO-PURIN-9-YL)-3,4-DIHYDROXY-TETRAHYDRO-FURAN-2-YLMETHYL]-METHYL-SULFONIUM; AAD; 5'-[[2-(Aminooxy)Ethyl]Methylsulfonio]-5'-Deoxy-Adenosine

Database IDs

• PubChem SID: 160965708; 46509003
• PubChem CID: 46936415

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.443856
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -2.6191325
• LogD (pH = 7.4): -2.7011948
• Log P: -2.703049
• Molar Refractivity: 88.1058 cm^3
• Polarizability: 35.02261 Å^3
• Polar Surface Area: 154.56 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.43
• LOG S: -2.3
• Solubility (Water): 1.96e+00 g/l

DETAILS

DrugBank - DB02523

Drug information: experimental