4-amino-8-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dimethyl-7,8-dihydropteridin-7-one

• ChemBase ID: 160033
• Molecular Formular: C13H17N5O4
• Molecular Mass: 307.30518
• Monoisotopic Mass: 307.12805405
• SMILES: [C@H]1(C[C@@H](O[C@@H]1CO)n1c2c(nc(c1=O)C)c(nc(n2)C)N)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1c(=O)c(C)nc2c1nc(C)nc2N
• InChI: InChI=1S/C13H17N5O4/c1-5-13(21)18(9-3-7(20)8(4-19)22-9)12-10(15-5)11(14)16-6(2)17-12/h7-9,19-20H,3-4H2,1-2H3,(H2,14,16,17)/t7-,8-,9-/m1/s1
• InChIKey: MJVDCGSSLDHUHZ-IWSPIJDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-8-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dimethyl-7,8-dihydropteridin-7-one
• IUPAC Traditional name: 4-amino-8-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dimethylpteridin-7-one
• Synonyms: 4-Amino-8-(2-deoxy-β-D-erythro-pentofuranosyl)-2,6-dimethyl-7(8H)pteridinone; DMAP; 4-Amino-2,6-dimethyl-8-(2'-deoxy-β-D-ribofuranosyl)-7(8H)-pteridone

Database IDs

• CAS Number: 195442-56-9
• PubChem SID: 162254168
• PubChem CID: 29971546

CALCULATED PROPERTIES

• Acid pKa: 13.894852
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -1.2298157
• LogD (pH = 7.4): -1.2284846
• Log P: -1.2284676
• Molar Refractivity: 78.8755 cm^3
• Polarizability: 28.735989 Å^3
• Polar Surface Area: 134.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Cyrstalline Solid
• Melting Point: >190°C dec.

DETAILS

Toronto Research Chemicals - A605170

A highly fluorescent adenosine 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.: Analytical Biochem., 298, 231 (2001)