(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-methyloxolan-3-ol

• ChemBase ID: 105141
• Molecular Formular: C10H13N5O2
• Molecular Mass: 235.24252
• Monoisotopic Mass: 235.10692468
• SMILES: n1c2c(ncnc2n(c1)[C@@H]1O[C@@H]([C@@H](O)C1)C)N
• Canonical SMILES: O[C@H]1C[C@@H](O[C@@H]1C)n1cnc2c1ncnc2N
• InChI: InChI=1S/C10H13N5O2/c1-5-6(16)2-7(17-5)15-4-14-8-9(11)12-3-13-10(8)15/h3-7,16H,2H2,1H3,(H2,11,12,13)/t5-,6+,7-/m1/s1
• InChIKey: FFHPXOJTVQDVMO-DSYKOEDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-methyloxolan-3-ol
• IUPAC Traditional name: (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-methyloxolan-3-ol
• Synonyms: 2′,5′-Dideoxyadenosine; 2',5'-DIDEOXYADENOSINE

Database IDs

• CAS Number: 6698-26-6
• MDL Number: MFCD00210904
• PubChem SID: 24894132; 162091976
• PubChem CID: 65166

CALCULATED PROPERTIES

• Acid pKa: 14.065469
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.26156873
• LogD (pH = 7.4): -0.14512758
• Log P: -0.14341584
• Molar Refractivity: 60.1412 cm^3
• Polarizability: 23.187206 Å^3
• Polar Surface Area: 99.08 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble
• Apperance: white solid

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: rat ... Adcy2(81636)

Product Information

• Purity: ≥95% (HPLC); 98%
• Empirical Formula (Hill Notation): C10H13N5O2

DETAILS

MP Biomedicals - 02158910

Purity: 98%
Inhibitor of adenylate cyclase.

Sigma Aldrich - D7408

Biochem/physiol Actions
Cell-permeable adenylyl cyclase inhibitor. IC50 = 2.7 μM in detergent-dispersed rat brain preparations.
Reconstitution
Store at -20 °C after reconstitution.

REFERENCES

• Holgate, S.T., et al., Proc. Natl. Acad. Sci. USA, 77 : 6800 (1980).