1-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione

• ChemBase ID: 133349
• Molecular Formular: C6H6N4O3
• Molecular Mass: 182.13684
• Monoisotopic Mass: 182.04399007
• SMILES: Cn1c(=O)c2c([nH]c(=O)[nH]2)[nH]c1=O
• Canonical SMILES: O=c1[nH]c2c([nH]1)c(=O)n(c(=O)[nH]2)C
• InChI: InChI=1S/C6H6N4O3/c1-10-4(11)2-3(9-6(10)13)8-5(12)7-2/h1H3,(H,9,13)(H2,7,8,12)
• InChIKey: QFDRTQONISXGJA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
• IUPAC Traditional name: 1-methyluric acid
• Synonyms: 1-U; 1MUA; 1-Methyluric acid; 1-Methyl-2,6,8-trihydroxypurine; 7,9-Dihydro-1-methyl-1H-purine-2,6,8(3H)-trione; 1-Methyl-uric Acid; 1-Methyluric Acid; 1-甲基-2,6,8-三羟基嘌呤; 1-甲基尿酸

Database IDs

• CAS Number: 708-79-2
• EC Number: 211-905-7
• MDL Number: MFCD00042987
• Beilstein Number: 195190
• PubChem SID: 162227626; 24897125
• PubChem CID: 69726

CALCULATED PROPERTIES

• Acid pKa: 7.671819
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -1.3232439
• LogD (pH = 7.4): -1.4924389
• Log P: -1.3205168
• Molar Refractivity: 50.5253 cm^3
• Polarizability: 15.11369 Å^3
• Polar Surface Area: 90.54 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: aqueous Base
• Apperance: White to Off-White Solid
• Melting Point: >325°C

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC); 99%
• Empirical Formula (Hill Notation): C6H6N4O3

DETAILS

Sigma Aldrich - M6885

包装
50, 100 mg in glass bottle
Biochem/physiol Actions
1-Methyluric acid (1-U) is a major metabolite of caffeine and theophylline with antioxidant activity that protects molecules such as low density lipoproteins (LDL) from oxidative modifications. 1-Methyluric acid may be used in studies aimed at differentiating the activities of caffeine and theophylline metabolites.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M6885.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - M338180

A metabolite of Theophylline.

REFERENCES

• Chen, Y., et al.: Clin. Exper. Pharmacol. Physiol., 36, 828 (2009)
• Yu, C., et al.: J. Bacteriol., 191, 4624 (2009)
• Jetter, A., et al.: Eur. J. Clin. Pharmacol., 65, 411 (2009)