2-amino-8-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-methyl-3,4,7,8-tetrahydropteridine-4,7-dione

• ChemBase ID: 173526
• Molecular Formular: C12H15N5O5
• Molecular Mass: 309.278
• Monoisotopic Mass: 309.10731861
• SMILES: C1C([C@H](O[C@H]1n1c2c(ncc1=O)c(=O)n(c(n2)N)C)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](CC1O)n1c(=O)cnc2c1nc(N)n(c2=O)C
• InChI: InChI=1S/C12H15N5O5/c1-16-11(21)9-10(15-12(16)13)17(7(20)3-14-9)8-2-5(19)6(4-18)22-8/h3,5-6,8,18-19H,2,4H2,1H3,(H2,13,15)/t5?,6-,8-/m1/s1
• InChIKey: RJCSBEHKYSZPAX-KYVYOHOSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-8-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-methyl-3,4,7,8-tetrahydropteridine-4,7-dione
• IUPAC Traditional name: 2-amino-8-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-methylpteridine-4,7-dione
• Synonyms: 2-Amino-8-(2-deoxy-β-D-erythro-pentofuranosyl)-3-methyl-4,7(3H,8H)-pteridinedione; 3-MI; 3-Methyl-8-(2'-deoxy-β-D-ribofuranosyl)isoxanthopterin

Database IDs

• CAS Number: 170379-51-8
• PubChem SID: 164229436
• PubChem CID: 71750284

CALCULATED PROPERTIES

• Acid pKa: 13.894877
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -1.8372421
• LogD (pH = 7.4): -1.8360066
• Log P: -1.8359907
• Molar Refractivity: 82.0268 cm^3
• Polarizability: 27.623919 Å^3
• Polar Surface Area: 141.05 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colourless Cyrstalline Solid
• Melting Point: >250°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M298205

A highly fluorescent guanosine analogue, which in a dimethoxytrityl, phosphoramidite protected form, can be site-specifically inserted into oligonucleotides through a 3’,5’-phosphodiester linkage using an automated DNA synthesizer.

REFERENCES

• Hawkins, M.E., et al.: Nucleic Acids Research, 23, 15 (1995)