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

• ChemBase ID: 3042
• Molecular Formular: C14H21N7O8S
• Molecular Mass: 447.42364
• Monoisotopic Mass: 447.11723167
• SMILES: C[C@@H](O)[C@@H](N)C(=O)NS(=O)(=O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1O)n1cnc2c1ncnc2N
• Canonical SMILES: C[C@H]([C@H](C(=O)NS(=O)(=O)OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1cnc2c1ncnc2N)N)O
• InChI: InChI=1S/C14H21N7O8S/c1-5(22)7(15)13(25)20-30(26,27)28-2-6-9(23)10(24)14(29-6)21-4-19-8-11(16)17-3-18-12(8)21/h3-7,9-10,14,22-24H,2,15H2,1H3,(H,20,25)(H2,16,17,18)/t5-,6+,7-,9+,10-,14-/m1/s1
• InChIKey: UPVAPSGKXAAHBG-UWYIUFELSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 160966489; 46506859
• PubChem CID: 46936651

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.4217896
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -4.6382256
• LogD (pH = 7.4): -4.5477734
• Log P: -4.5568914
• Molar Refractivity: 98.1048 cm^3
• Polarizability: 39.755466 Å^3
• Polar Surface Area: 238.03 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.49
• LOG S: -1.94
• Solubility (Water): 5.12e+00 g/l

DETAILS

DrugBank - DB03355

Drug information: experimental