(4aR,6R,7R,7aS)-6-(6-amino-8-azido-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-one

• ChemBase ID: 102954
• Molecular Formular: C10H11N8O6P
• Molecular Mass: 370.218101
• Monoisotopic Mass: 370.05391674
• SMILES: [N-]=[N+]=Nc1nc2c(ncnc2n1[C@@H]1O[C@@H]2COP(=O)(O[C@H]2[C@H]1O)O)N
• Canonical SMILES: [N-]=[N+]=Nc1nc2c(n1[C@@H]1O[C@H]3[C@H]([C@H]1O)OP(=O)(OC3)O)ncnc2N
• InChI: InChI=1S/C10H11N8O6P/c11-7-4-8(14-2-13-7)18(10(15-4)16-17-12)9-5(19)6-3(23-9)1-22-25(20,21)24-6/h2-3,5-6,9,19H,1H2,(H,20,21)(H2,11,13,14)/t3-,5-,6-,9-/m1/s1
• InChIKey: KTMLKBFMGWQTEK-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6R,7R,7aS)-6-(6-amino-8-azido-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-one
• IUPAC Traditional name: (4aR,6R,7R,7aS)-6-(6-amino-8-azidopurin-9-yl)-2,7-dihydroxy-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-one
• Synonyms: 8-AZIDOADENOSINE-3',5'-cyclic-MONOPHOSPHATE FREE ACID

Database IDs

• CAS Number: 31966-52-6
• PubChem SID: 162089376
• PubChem CID: 115296

CALCULATED PROPERTIES

• Acid pKa: 1.8319762
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): -2.7255533
• LogD (pH = 7.4): -2.7041204
• Log P: -2.3151975
• Molar Refractivity: 80.0504 cm^3
• Polarizability: 30.320751 Å^3
• Polar Surface Area: 184.27 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: 0°C, Desiccate, Protect from light

Product Information

• Purity: >95%

DETAILS

MP Biomedicals - 02150058

Free Acid
Purity: >95% by TLC
Supplied in anhydrous methanol
Useful as a photo-affinity probe

REFERENCES

• Haley, B.E. and Hoffman, J.F., Proc. Nat. Acad. Sci. USA , 71 : 3367, (1974).