8-hydroxy-3-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methyl-3H,5H,6H,7H,8H,10H-pyrimido[1,2-a]purin-10-one

• ChemBase ID: 173817
• Molecular Formular: C14H19N5O5
• Molecular Mass: 337.33116
• Monoisotopic Mass: 337.13861873
• SMILES: C1C([C@H](O[C@H]1n1c2c(nc1)c(=O)n1c(n2)NC(CC1O)C)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](CC1O)n1cnc2c1nc1NC(C)CC(n1c2=O)O
• InChI: InChI=1S/C14H19N5O5/c1-6-2-9(22)19-13(23)11-12(17-14(19)16-6)18(5-15-11)10-3-7(21)8(4-20)24-10/h5-10,20-22H,2-4H2,1H3,(H,16,17)/t6?,7?,8-,9?,10-/m1/s1
• InChIKey: DKBDYPZFCQIHPX-DRAUJQIPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-hydroxy-3-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methyl-3H,5H,6H,7H,8H,10H-pyrimido[1,2-a]purin-10-one
• IUPAC Traditional name: 8-hydroxy-3-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methyl-5H,6H,7H,8H-pyrimido[1,2-a]purin-10-one
• Synonyms: 3-(2-Deoxy-β-D-erythro-pentofuranosyl)-4,6,7,8-tetrahydro-8-hydroxy-6-methylpyrimido[1,2-a]purin-10(3H)-one; α-Me-γ-OH-PdG; Cr-PdG; α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine(Mixture of Diastereomers)

Database IDs

• CAS Number: 132014-87-0
• PubChem SID: 164229727
• PubChem CID: 71750391

CALCULATED PROPERTIES

• Acid pKa: 13.230736
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.153203
• LogD (pH = 7.4): -1.1531665
• Log P: -1.1531655
• Molar Refractivity: 80.7132 cm^3
• Polarizability: 30.867731 Å^3
• Polar Surface Area: 132.44 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid
• Melting Point: 135-137°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M312890

A genotoxic cyclic adduct of 2'-deoxyguanosine with crotonaldehyde. Histones accelerate the cyclic 1,N2-propanoguanine adduct-formation of DNA by the primary metabolite of alcohol and carcinogenic crotonaldehyde.

REFERENCES

• Fang, J., et al.: Carcinogenesis, 18, 627 (1997)
• Wang, M., et al.: Chem. Res. Toxicol., 14, 1025 (1997)
• Kurtz, A., et al.: J. Biol. Chem., 278, 5970 (1997)