{[(2R,3S,4R,5R)-5-(6-amino-8-azido-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 106071
• Molecular Formular: C10H14N8O10P2
• Molecular Mass: 468.213282
• Monoisotopic Mass: 468.03081195
• SMILES: Nc1ncnc2c1nc(N=[N+]=[N-])n2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@H]1O
• Canonical SMILES: [N-]=[N+]=Nc1nc2c(n1[C@@H]1O[C@@H]([C@H]([C@H]1O)OP(=O)(O)O)COP(=O)(O)O)ncnc2N
• InChI: InChI=1S/C10H14N8O10P2/c11-7-4-8(14-2-13-7)18(10(15-4)16-17-12)9-5(19)6(28-30(23,24)25)3(27-9)1-26-29(20,21)22/h2-3,5-6,9,19H,1H2,(H2,11,13,14)(H2,20,21,22)(H2,23,24,25)/t3-,5-,6-,9-/m1/s1
• InChIKey: WKDATDVMHNDLJY-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4R,5R)-5-(6-amino-8-azido-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,3S,4R,5R)-5-(6-amino-8-azidopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxyphosphonic acid
• Synonyms: 8-N₃ pAp; 8-AZIDOADENOSINE 3,5'-BIPHOSPHATE TRIETHYLAMMONIUM SALT

Database IDs

• PubChem SID: 162105364
• PubChem CID: 54435034

CALCULATED PROPERTIES

• Acid pKa: 0.7043348
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): -6.352251
• LogD (pH = 7.4): -8.717028
• Log P: -3.4049609
• Molar Refractivity: 94.7023 cm^3
• Polarizability: 36.128136 Å^3
• Polar Surface Area: 262.03 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 0°C

DETAILS

MP Biomedicals - 02198909

Triethylammonium salt solution in absolute methanol. Contains 2', 5' isomer.
λ_max =281 at pH 7.0, ε13300