8-(dimethylamino)-7-methyl-10-(2,3,4,5-tetrahydroxypentyl)-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione

• ChemBase ID: 177603
• Molecular Formular: C18H23N5O6
• Molecular Mass: 405.40512
• Monoisotopic Mass: 405.16483348
• SMILES: c1(c(cc2c(c1)n(c1c(n2)c(=O)[nH]c(=O)n1)CC(C(C(CO)O)O)O)C)N(C)C
• Canonical SMILES: OCC(C(C(Cn1c2cc(N(C)C)c(cc2nc2c1nc(=O)[nH]c2=O)C)O)O)O
• InChI: InChI=1S/C18H23N5O6/c1-8-4-9-11(5-10(8)22(2)3)23(6-12(25)15(27)13(26)7-24)16-14(19-9)17(28)21-18(29)20-16/h4-5,12-13,15,24-27H,6-7H2,1-3H3,(H,21,28,29)
• InChIKey: IGQLDUYTWDABFK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-(dimethylamino)-7-methyl-10-(2,3,4,5-tetrahydroxypentyl)-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione
• IUPAC Traditional name: 8-(dimethylamino)-7-methyl-10-(2,3,4,5-tetrahydroxypentyl)-3H-benzo[g]pteridine-2,4-dione
• Synonyms: 8-Demethyl-8-(dimethylamino)riboflavin; 8-Dimethylaminoriboflavin; Roseoflavine; Roseoflavin

Database IDs

• CAS Number: 51093-55-1
• PubChem SID: 164233513
• PubChem CID: 170973

CALCULATED PROPERTIES

• Acid pKa: 6.970511
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -1.3525953
• LogD (pH = 7.4): -1.8762378
• Log P: -1.3219178
• Molar Refractivity: 105.6558 cm^3
• Polarizability: 38.550694 Å^3
• Polar Surface Area: 158.29 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Dark Reddish/Brown Crystalline Solid
• Melting Point: 276-278°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer

DETAILS

Toronto Research Chemicals - R685000

An analog known to compete with Riboflavin in Lactobacillus casei. Riboflavin kinase substrate and inhibitor.

REFERENCES

• Miroux, B., et al.: J. Mol. Biol., 260, 289 (1996)
• Gauden, M., et al.: Biochemistry, 44, 3653 (1996)
• Meissner, B., et al.: J. Biol. Chem., 282, 33142 (1996)
• Grill, S., et al.: J. Bacteriol., 190, 1546 (1996)