1,3-diazinane-2,4,5-trione

• ChemBase ID: 130771
• Molecular Formular: C4H4N2O3
• Molecular Mass: 128.08616
• Monoisotopic Mass: 128.022192
• SMILES: C1C(=O)C(=O)NC(=O)N1
• Canonical SMILES: O=C1NCC(=O)C(=O)N1
• InChI: InChI=1S/C4H4N2O3/c7-2-1-5-4(9)6-3(2)8/h1H2,(H2,5,6,8,9)
• InChIKey: FQXOOGHQVPKHPG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-diazinane-2,4,5-trione
• IUPAC Traditional name: 1,3-diazinane-2,4,5-trione
• Synonyms: Isobarbituric acid; 2,4,5-Trihydroxypyrimidine; 5-Hydroxyuracil; Dihydro-2,4,5(3H)-pyrimidinetrione; NSC 95958; Isobarbituric Acid; 2,4,5-三羟基嘧啶; 5-羟基尿嘧啶; 异巴比妥酸

Database IDs

• CAS Number: 496-76-4
• EC Number: 207-829-9
• MDL Number: MFCD00082987
• Beilstein Number: 127205
• PubChem SID: 24895907; 162225049
• PubChem CID: 96994

CALCULATED PROPERTIES

• Acid pKa: 6.005861
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.2788285
• LogD (pH = 7.4): -2.586724
• Log P: -1.1610008
• Molar Refractivity: 26.3921 cm^3
• Polarizability: 10.119884 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: light yellow crystalline
• Melting Point: >300 °C (dec.)(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ~98%; ≥95.0% (HPLC)
• Grade: analytical standard, for drug analysis; purum
• Ignition Residue: ~1%
• Empirical Formula (Hill Notation): C4H4N2O3

DETAILS

Toronto Research Chemicals - I780030

A 5-hydroxy derivative of the nucleobase Uracil (U801000) and an isomer of Barbituric Acid (B118650). Studies show that it can form stable base pairs with all four bases in a DNA duplex. It has been used as oxidative DNA damage biomarker in tissue enginee

REFERENCES

• Varatharasa T. et al.: Chem. Comm., 3, 400 (2005)
• Jaruga, P. et al.: Nucleic Acid Res., 24, 1389 (2005)
• Rodriguez, H. et al.: Adv. Exp. Med. Biol., 534, 129 (2005)