7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl](2-13C,1,3-15N2)-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione

• ChemBase ID: 177516
• Molecular Formular: C17H20N4O6
• Molecular Mass: 379.34337263
• Monoisotopic Mass: 379.135709
• SMILES: c1(c(cc2c(c1)nc1c(n2C[C@@H]([C@@H]([C@@H](CO)O)O)O)[15n][13c](=O)[15nH]c1=O)C)C
• Canonical SMILES: OC[C@H]([C@H]([C@H](Cn1c2cc(C)c(cc2nc2c1[15n][13c](=O)[15nH]c2=O)C)O)O)O
• InChI: InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1/i17+1,19+1,20+1
• InChIKey: AUNGANRZJHBGPY-LFHFTARISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl](2-^1^3C,1,3-^1^5N₂)-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione
• IUPAC Traditional name: 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl](2-^1^3C,1,3-^1^5N₂)-3H-benzo[g]pteridine-2,4-dione
• Synonyms: (-)-Riboflavin-13C,15N2; 6,7-Dimethyl-9-D-ribitylisoalloxazine-13C,15N2; Beflavin-13C,15N2; Beflavine-13C,15N2; Flavaxin-13C,15N2; Flavin BB-13C,15N2; Flaxain-13C,15N2; Hyre-13C,15N2; Lactobene-13C,15N2; Lactoflavin-13C,15N2; Lactoflavine-13C,15N2; NCI 0033298-13C,15N2; NSC 33298-13C,15N2; Vitaflavine-13C,15N2; Vitamin B2-13C,15N2; Vitamin G-13C,15N2; Vitasan B2-13C,15N2; Riboflavin-13C,15N2

Database IDs

• PubChem SID: 164233426
• PubChem CID: 71752069

CALCULATED PROPERTIES

• Acid pKa: 6.9699388
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.93084645
• LogD (pH = 7.4): -1.4706613
• Log P: -0.91654027
• Molar Refractivity: 96.2684 cm^3
• Polarizability: 35.49111 Å^3
• Polar Surface Area: 155.05 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Yellow Solid
• Melting Point: >185°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R415002

One of the bioactive forms of Riboflavin. Nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, leafy vegetables. Richest natural source is yeast. Minute amounts present in all plant and animal cells. Vitamin (enzyme cofactor).

REFERENCES

• Unna, K., et al.: J. Pharmacol. Exp. Ther., 76, 75 (1942)
• Rivlin, et al.: N. Engl. J. Med., 283, 463 (1942)
• Al-Shammary, F.J., et al.: Anal. Profiles Drug Subs., 19, 429 (1942)