3-methyl-4-oxo-3H,4H-imidazo[4,3-d][1,2,3,5]tetrazine-8-carboxylic acid

• ChemBase ID: 178137
• Molecular Formular: C6H5N5O3
• Molecular Mass: 195.1356
• Monoisotopic Mass: 195.03923905
• SMILES: c12n(c(=O)n(nn1)C)cnc2C(=O)O
• Canonical SMILES: OC(=O)c1ncn2c1nnn(c2=O)C
• InChI: InChI=1S/C6H5N5O3/c1-10-6(14)11-2-7-3(5(12)13)4(11)8-9-10/h2H,1H3,(H,12,13)
• InChIKey: VVTMIOYTNALQAW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl-4-oxo-3H,4H-imidazo[4,3-d][1,2,3,5]tetrazine-8-carboxylic acid
• IUPAC Traditional name: 3-methyl-4-oxoimidazo[4,3-d][1,2,3,5]tetrazine-8-carboxylic acid
• Synonyms: 3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid; 3,4-Dihydro-3-methyl-4-oxo-imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic Acid; 3-Methyl-4-oxo-8-imidazolo[5,1-d][1,2,3,5]tetrazinecarboxylic Acid; Temozolomide-8-carboxylic Acid; Temozolomide Acid

Database IDs

• CAS Number: 113942-30-6
• MDL Number: MFCD12032160
• PubChem SID: 164234047
• PubChem CID: 11830328

CALCULATED PROPERTIES

• Acid pKa: 3.264134
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.6924331
• LogD (pH = 7.4): -2.9090495
• Log P: 0.52440447
• Molar Refractivity: 46.0387 cm^3
• Polarizability: 15.641977 Å^3
• Polar Surface Area: 100.15 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 166-168°C

Safety Information

• Storage Condition: Refrigerator

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - T017780

A metabolite of Temozolomide (T017775) as antitumor agent.

REFERENCES

• Schulman, M., et al.: J. Biol. Chem., 196, 513 (1952)
• Stevens, M., et al.: Cancer Res., 47, 5846 (1952)
• Baker, S., et al.: Clin. Cancer Res., 5, 309 (1952)