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

• ChemBase ID: 3509
• Molecular Formular: C13H19N7O8S
• Molecular Mass: 433.39706
• Monoisotopic Mass: 433.1015816
• SMILES: N[C@H](CO)C(=O)NS(=O)(=O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1O)n1cnc2c1ncnc2N
• Canonical SMILES: OC[C@H](C(=O)NS(=O)(=O)OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1cnc2c1ncnc2N)N
• InChI: InChI=1S/C13H19N7O8S/c14-5(1-21)12(24)19-29(25,26)27-2-6-8(22)9(23)13(28-6)20-4-18-7-10(15)16-3-17-11(7)20/h3-6,8-9,13,21-23H,1-2,14H2,(H,19,24)(H2,15,16,17)/t5-,6+,8+,9-,13-/m1/s1
• InChIKey: HQXFJGONGJPTLZ-FLNYCXGNSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 46508279; 160966948
• PubChem CID: 46936812

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.4243417
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -5.0560255
• LogD (pH = 7.4): -4.9651203
• Log P: -4.9759417
• Molar Refractivity: 93.686 cm^3
• Polarizability: 37.947083 Å^3
• Polar Surface Area: 238.03 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.63
• LOG S: -1.84
• Solubility (Water): 6.31e+00 g/l

DETAILS

DrugBank - DB03869

Drug information: experimental