2-amino-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one hydrate

• ChemBase ID: 165967
• Molecular Formular: C10H15N5O5
• Molecular Mass: 285.2566
• Monoisotopic Mass: 285.10731861
• SMILES: O.[nH]1c(nc2c(c1=O)ncn2[C@H]1C[C@H]([C@H](O1)CO)O)N
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cnc2c1nc(N)[nH]c2=O.O
• InChI: InChI=1S/C10H13N5O4.H2O/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6;/h3-6,16-17H,1-2H2,(H3,11,13,14,18);1H2/t4-,5-,6-;/m1./s1
• InChIKey: LZSCQUCOIRGCEJ-RWOHWRPJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one hydrate
• IUPAC Traditional name: 2-amino-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one hydrate
• Synonyms: 9-(2-Deoxy-β-D-erythro-pentofuranosyl)guanine Monohydrate; Deoxyguanosine Monohydrate; Guanine Deoxyriboside Monohydrate; NSC 22837; 2'-Deoxyguanosine Monohydrate

Database IDs

• CAS Number: 312693-72-4
• PubChem SID: 162260100
• PubChem CID: 46780628

CALCULATED PROPERTIES

• Acid pKa: 10.158529
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.8056743
• LogD (pH = 7.4): -1.8062477
• Log P: -1.8055801
• Molar Refractivity: 63.1104 cm^3
• Polarizability: 23.620188 Å^3
• Polar Surface Area: 134.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: >255°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D239550

Nucleoside analog.

REFERENCES

• Krenitsky, T.A., et al.: Biochemistry, 20, 3615 (1981)
• Chapeau, M.-C., et al.: Chem. Res. Toxicol., 4, 636 (1981)