(2R,3S)-3-(6-amino-9H-purin-9-yl)nonan-2-ol hydrochloride

• ChemBase ID: 170232
• Molecular Formular: C14H24ClN5O
• Molecular Mass: 313.82626
• Monoisotopic Mass: 313.16693809
• SMILES: n1cnc2c(c1N)ncn2[C@@H](CCCCCC)[C@H](O)C.Cl
• Canonical SMILES: CCCCCC[C@H](n1cnc2c1ncnc2N)[C@H](O)C.Cl
• InChI: InChI=1S/C14H23N5O.ClH/c1-3-4-5-6-7-11(10(2)20)19-9-18-12-13(15)16-8-17-14(12)19;/h8-11,20H,3-7H2,1-2H3,(H2,15,16,17);1H/t10-,11+;/m1./s1
• InChIKey: VVDXNJRUNJMYOZ-DHXVBOOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-3-(6-amino-9H-purin-9-yl)nonan-2-ol hydrochloride
• IUPAC Traditional name: (2R,3S)-3-(6-aminopurin-9-yl)nonan-2-ol hydrochloride
• Synonyms: EHNA; rac erythro-9-(2-Hydroxy-3-nonyl)adenine, Hydrochloride

Database IDs

• CAS Number: 81408-49-3
• PubChem SID: 164226142
• PubChem CID: 11957547

CALCULATED PROPERTIES

• Acid pKa: 14.809135
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.9902704
• LogD (pH = 7.4): 2.134316
• Log P: 2.1365085
• Molar Refractivity: 79.5539 cm^3
• Polarizability: 30.452444 Å^3
• Polar Surface Area: 89.85 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White to Off-White Solid
• Melting Point: 163-170°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H825550

A potent inhibitor of phosphodiesterase II (PDE II) (IC50=800nM). Does ot inhibit other PDE isozymes (IC50>100uM). Inhibits the retrograde transport motor, dynein. Also inhibits adenosine deaminase (Ki=4nM).

REFERENCES

• Lorbar, M., et al.: J. Mol. Cell. Cardiol., 31, 401 (1999)
• Verde, I., et al.: Br. J. Pharmacol., 127, 65 (1999)