6,8-dimethyl-5H,6H,7H,8H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione

• ChemBase ID: 179752
• Molecular Formular: C7H7N5O2
• Molecular Mass: 193.16278
• Monoisotopic Mass: 193.05997449
• SMILES: n1(c(=O)n(c(=O)c2c1nncn2)C)C
• Canonical SMILES: Cn1c2nncnc2c(=O)n(c1=O)C
• InChI: InChI=1S/C7H7N5O2/c1-11-5-4(8-3-9-10-5)6(13)12(2)7(11)14/h3H,1-2H3
• InChIKey: RRTKVYSLIGQWCO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,8-dimethyl-5H,6H,7H,8H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione
• IUPAC Traditional name: 6,8-dimethyl-5H,6H,7H,8H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione
• Synonyms: Planomycin; Pulanomycin; Antibiotic 10204-BII; Fervenulin

Database IDs

• CAS Number: 483-57-8
• PubChem SID: 164235662
• PubChem CID: 249646

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -1.0882827
• LogD (pH = 7.4): -1.0882827
• Log P: -1.0882827
• Molar Refractivity: 48.2578 cm^3
• Polarizability: 16.70622 Å^3
• Polar Surface Area: 79.29 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Protein tyrosine phosphatase (PTP) inhibitor

Product Information

• Biological Source: Isol. from Streptomyces fervens and Streptomyces rubrireticuli
• Application(s): Antibiotic

REFERENCES

• Pfleiderer, W. et al., Annalen, 1958, 615, 42, (synth)
• Daves, G.D. et al., J.O.C., 1961, 26, 5256, (isol, struct, uv, ir)
• Yoneda, F. et al., J. Het. Chem., 1970, 7, 1443, (synth)
• Taylor, E.C. et al., J.O.C., 1975, 40, 2321, (synth, nmr)
• Senda, S. et al., J.A.C.S., 1977, 99, 7358, (synth)
• Ichiba, M. et al., J.O.C., 1978, 43, 469, (synth, ir, uv, ms, nmr)
• CRC Handb. of Antibiotic Compounds, (eds. Brdy, J. et al), CRC Press, Boca Raton, 1984, 5, 198, (props)
• Werner-Simon, S. et al., J. Het. Chem., 1996, 33, 949, (synth, derivs)
• Koshino, H. et al., Heterocycles, 2000, 52, 811-817, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, FBP300