2-{7,8,10-trimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-3-yl}acetic acid

• ChemBase ID: 172424
• Molecular Formular: C15H14N4O4
• Molecular Mass: 314.29606
• Monoisotopic Mass: 314.10150495
• SMILES: n1(c(=O)nc2c(c1=O)nc1c(n2C)cc(c(c1)C)C)CC(=O)O
• Canonical SMILES: OC(=O)Cn1c(=O)nc2c(c1=O)nc1c(n2C)cc(c(c1)C)C
• InChI: InChI=1S/C15H14N4O4/c1-7-4-9-10(5-8(7)2)18(3)13-12(16-9)14(22)19(6-11(20)21)15(23)17-13/h4-5H,6H2,1-3H3,(H,20,21)
• InChIKey: GJSCQGXLPDWOMG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{7,8,10-trimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-3-yl}acetic acid
• IUPAC Traditional name: {7,8,10-trimethyl-2,4-dioxobenzo[g]pteridin-3-yl}acetic acid
• Synonyms: 4,10-Dihydro-7,8,10-trimethyl-2,4-dioxobenzo[g]pteridine-3(2H)-acetic Acid; 3-(Carboxymethyl)lumiflavin; Flavin I; N3-Carboxymethyl Lumiflavin; Lumiflavin-3-acetic Acid

Database IDs

• CAS Number: 20227-26-3
• PubChem SID: 164228334
• PubChem CID: 688508

CALCULATED PROPERTIES

• Acid pKa: 3.2245898
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -0.88794065
• LogD (pH = 7.4): -2.0747905
• Log P: 1.366226
• Molar Refractivity: 83.0699 cm^3
• Polarizability: 29.779884 Å^3
• Polar Surface Area: 102.64 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Brown Solid
• Melting Point: >270°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - L473910

The acetic acid derivative of Lumiflavin (L473900) used in photochemical induced dynamic nuclear polarization (photo-CIDNP) study of flavoproteins. Lumiflavin-3-acetic Acid is also used in the study riboflavin-binding protein interaction.

REFERENCES

• Van Schagen, C.G. et al.: Biochemistry, 21, 402 (1982)
• Mifflin, T.E. et al.: Arch. Biochem. Biophys., 224, 319 (1982)