5-amino-[1,2,3]triazolo[4,5-d]pyrimidin-7-ol

• ChemBase ID: 1442
• Molecular Formular: C4H4N6O
• Molecular Mass: 152.11416
• Monoisotopic Mass: 152.04465878
• SMILES: Nc1nc(O)c2[nH]nnc2n1
• Canonical SMILES: Nc1nc(O)c2c(n1)nn[nH]2
• InChI: InChI=1S/C4H4N6O/c5-4-6-2-1(3(11)7-4)8-10-9-2/h(H4,5,6,7,8,9,10,11)
• InChIKey: LPXQRXLUHJKZIE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-[1,2,3]triazolo[4,5-d]pyrimidin-7-ol
• IUPAC Traditional name: @8-azaguanine
• Synonyms: 8-Azaguanine

Database IDs

• CAS Number: 134-58-7
• PubChem SID: 160964901
• PubChem CID: 8646

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.769922
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.9364859
• LogD (pH = 7.4): -0.93666565
• Log P: -0.9364836
• Molar Refractivity: 40.1688 cm^3
• Polarizability: 12.935373 Å^3
• Polar Surface Area: 110.7 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.87
• LOG S: -1.43
• Solubility (Water): 5.67e+00 g/l

PROPERTIES

Physical Property

• Solubility: Insoluble
• Hydrophobicity(logP): -0.71 [HANSCH,C ET AL. (1995)]

DETAILS

DrugBank - DB01667

• Drug Groups: experimental
• Description: One of the early purine analogs showing antineoplastic activity. It functions as an antimetabolite and is easily incorporated into ribonucleic acids. [PubChem]
• References: Tong, George L.; Lee, William W.; Goodman, Leon; Frederiksen, Sune (1965). "Synthesis of some 2′-deoxyribosides of 8-azaadenine". Archives of Biochemistry and Biophysics (University of California: Elsevier) 112 (1): 76. "http://dx.doi.org/10.1016/0003-9861(65)90012-3":http://dx.doi.org/10.1016/0003-9861(65)90012-3; Michels AW, Ostrov DA, Zhang L, Nakayama M, Fuse M, McDaniel K, Roep BO, Gottlieb PA, Atkinson MA, Eisenbarth GS: Structure-based selection of small molecules to alter allele-specific MHC class II antigen presentation. J Immunol. 2011 Dec 1;187(11):5921-30. Epub 2011 Oct 31. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Tong, George L.; Lee, William W.; Goodman, Leon; Frederiksen, Sune (1965). "Synthesis of some 2′-deoxyribosides of 8-azaadenine". Archives of Biochemistry and Biophysics (University of California: Elsevier) 112 (1): 76. "http://dx.doi.org/10.1016/0003-9861(65)90012-3":http://dx.doi.org/10.1016/0003-9861(65)90012-3
• Michels AW, Ostrov DA, Zhang L, Nakayama M, Fuse M, McDaniel K, Roep BO, Gottlieb PA, Atkinson MA, Eisenbarth GS: Structure-based selection of small molecules to alter allele-specific MHC class II antigen presentation. J Immunol. 2011 Dec 1;187(11):5921-30. Epub 2011 Oct 31. Pubmed