7,8,10-trimethyl-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione

• ChemBase ID: 4277
• Molecular Formular: C13H12N4O2
• Molecular Mass: 256.25998
• Monoisotopic Mass: 256.09602564
• SMILES: Cn1c2nc(=O)[nH]c(=O)c2nc2c1cc(C)c(C)c2
• Canonical SMILES: Cc1cc2nc3c(=O)[nH]c(=O)nc3n(c2cc1C)C
• InChI: InChI=1S/C13H12N4O2/c1-6-4-8-9(5-7(6)2)17(3)11-10(14-8)12(18)16-13(19)15-11/h4-5H,1-3H3,(H,16,18,19)
• InChIKey: KPDQZGKJTJRBGU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7,8,10-trimethyl-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione
• IUPAC Traditional name: lumiflavin
• Synonyms: 4-hydroxy-7,8,10-trimethylbenzo[g]pteridin-2(10H)-one; Lumiflavine; 7,8,10-TRIMETHYLBENZO[G]PTERIDINE-2,4(3H,10H)-DIONE; Lumilactoflavin; Lumiflavin; 7,8,10-Trimethylbenzo[g]pteridine-2,4(3H,10H)-dione; 7,8,10-Trimethylisoalloxazine; Lumiflavine

Database IDs

• CAS Number: 1088-56-8
• EC Number: 214-125-5
• MDL Number: MFCD00042742
• Beilstein Number: 269756
• PubChem SID: 160967709; 24896379; 46508913
• PubChem CID: 66184
• CHEBI ID: 43661
• Chemspider ID: 59571
• DrugBank ID: DB04726
• Wikipedia Title: Lumiflavin

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.970145
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.6502671
• LogD (pH = 7.4): 1.1105909
• Log P: 1.6645666
• Molar Refractivity: 72.0886 cm^3
• Polarizability: 25.498087 Å^3
• Polar Surface Area: 74.13 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.52
• LOG S: -3.07
• Solubility (Water): 2.18e-01 g/l

PROPERTIES

Physical Property

• Apperance: powder

Safety Information

• RTECS: OK4800000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

DrugBank - DB04726

Drug information: experimental

Sigma Aldrich - L4879

Biochem/physiol Actions
Lumiflavine (Lumiflavin) is produced by the photolysis of vitamin B2 (Riboflavin). Lumiflavine, a riboflavin uptake inhibitor, is used to study riboflavin uptake in intestinal epithelial (Caco-2) and other epithelial cells.

Toronto Research Chemicals - L473900

Lumiflavin is a toxic photolysis product of vitamin B2 (R415000).

REFERENCES

• Zhao, X. et al.: Chemosphere, 63, 1116 (2006)
• Litke, S.V. et al.: Khim. Fiz., 10, 48 (2006)
• Ye, W. et al.: Guang. Yaox. Xueb., 12, 175 (2006)