(2S)-2-amino-1-[({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}sulfonyl)amino]-3-sulfanylpropan-1-one

• ChemBase ID: 2409
• Molecular Formular: C13H19N7O7S2
• Molecular Mass: 449.46266
• Monoisotopic Mass: 449.07873798
• SMILES: N[C@H](CS)C(=O)NS(=O)(=O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1O)n1cnc2c1ncnc2N
• Canonical SMILES: SC[C@H](C(=O)NS(=O)(=O)OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1cnc2c1ncnc2N)N
• InChI: InChI=1S/C13H19N7O7S2/c14-5(2-28)12(23)19-29(24,25)26-1-6-8(21)9(22)13(27-6)20-4-18-7-10(15)16-3-17-11(7)20/h3-6,8-9,13,21-22,28H,1-2,14H2,(H,19,23)(H2,15,16,17)/t5-,6+,8+,9-,13-/m1/s1
• InChIKey: FTSDEWPMACCNGN-FLNYCXGNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-1-[({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}sulfonyl)amino]-3-sulfanylpropan-1-one
• IUPAC Traditional name: (2S)-2-amino-1-({[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxysulfonyl}amino)-3-sulfanylpropan-1-one
• Synonyms: 5'-O-(N-(L-Cysteinyl)-Sulfamoyl)Adenosine

Database IDs

• PubChem SID: 160965860; 46504849
• PubChem CID: 46936454

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.4297006
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -3.9570732
• LogD (pH = 7.4): -3.86756
• Log P: -3.872936
• Molar Refractivity: 99.8686 cm^3
• Polarizability: 40.297165 Å^3
• Polar Surface Area: 217.8 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.34
• LOG S: -2.25
• Solubility (Water): 2.52e+00 g/l

DETAILS

DrugBank - DB02684

Drug information: experimental