{[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[hydroxy(sulfanyl)phosphoryl]oxy})phosphoryl]oxy})phosphinic acid

• ChemBase ID: 2640
• Molecular Formular: C10H16N5O12P3S
• Molecular Mass: 523.246623
• Monoisotopic Mass: 522.97290187
• SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@@H](CO[P@@](=O)(O)O[P@](=O)(O)O[P@](=O)(O)S)[C@H](O)[C@H]1O
• Canonical SMILES: O[C@H]1[C@H](CO[P@](=O)(O[P@@](=O)(O[P@@](=O)(S)O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C10H16N5O12P3S/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(25-10)1-24-28(18,19)26-29(20,21)27-30(22,23)31/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H,20,21)(H2,11,12,13)(H2,22,23,31)/t4-,6-,7+,10+/m0/s1
• InChIKey: NLTUCYMLOPLUHL-FCIPNVEPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[hydroxy(sulfanyl)phosphoryl]oxy})phosphoryl]oxy})phosphinic acid
• IUPAC Traditional name: [(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({hydroxy[hydroxy(sulfanyl)phosphoryl]oxyphosphoryl}oxy)phosphinic acid
• Synonyms: Phosphothiophosphoric Acid-Adenylate Ester

Database IDs

• PubChem SID: 46507118; 160966089
• PubChem CID: 46936529; 6324649

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.67440754
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -8.387442
• LogD (pH = 7.4): -8.647017
• Log P: -5.9579325
• Molar Refractivity: 99.8055 cm^3
• Polarizability: 41.1497 Å^3
• Polar Surface Area: 258.9 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.53
• LOG S: -2.09
• Solubility (Water): 4.28e+00 g/l

DETAILS

DrugBank - DB02930

Drug information: experimental