sodium 10-[(2S,3S,4R)-5-(hydrogen phosphonatooxy)-2,3,4-trihydroxypentyl]-7,8-dimethyl-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione hydrate

• ChemBase ID: 130811
• Molecular Formular: C17H22N4NaO10P
• Molecular Mass: 496.340911
• Monoisotopic Mass: 496.09712384
• SMILES: Cc1cc2c(cc1C)n(c1nc(=O)[nH]c(=O)c1n2)C[C@@H]([C@@H]([C@@H](COP(=O)(O)[O-])O)O)O.O.[Na+]
• Canonical SMILES: O=c1[nH]c(=O)c2c(n1)n(C[C@@H]([C@@H]([C@@H](COP(=O)(O)[O-])O)O)O)c1c(n2)cc(c(c1)C)C.O.[Na+]
• InChI: InChI=1S/C17H21N4O9P.Na.H2O/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29;;/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29);;1H2/q;+1;/p-1/t11-,12+,14-;;/m0../s1
• InChIKey: BHRVCJBIICJWTH-APQIITSESA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 10-[(2S,3S,4R)-5-(hydrogen phosphonatooxy)-2,3,4-trihydroxypentyl]-7,8-dimethyl-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione hydrate
• IUPAC Traditional name: sodium 10-[(2S,3S,4R)-5-(hydrogen phosphonatooxy)-2,3,4-trihydroxypentyl]-7,8-dimethyl-3H-benzo[g]pteridine-2,4-dione hydrate
• Synonyms: FMN-Na; Riboflavin 5′-monophosphate sodium salt hydrate; Riboflavin 5′-phosphate sodium salt hydrate; Flavin mononucleotide; Riboflavin 5′-phosphate sodium salt; 核黄素-5′-磷酸钠 钠盐; 黄素单核苷酸; 核黄素磷酸钠 钠盐 水合物; 核黄素5′-磷酸盐 钠盐 水合物

Database IDs

• CAS Number: 130-40-5(anhydrous)
• EC Number: 204-988-6
• MDL Number: MFCD00150992
• Beilstein Number: 4106529
• PubChem SID: 162225089; 24894910; 24894817; 24894764
• PubChem CID: 23679076

CALCULATED PROPERTIES

• Acid pKa: 1.5655322
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -3.4562092
• LogD (pH = 7.4): -4.8923903
• Log P: -1.1982645
• Molar Refractivity: 106.0196 cm^3
• Polarizability: 39.881233 Å^3
• Polar Surface Area: 204.41 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, orange-yellow to very deep orange-red
• Apperance: powder
• Optical Rotation: [α]20/D +37 to +42°, c = 1.5 in 5 M HCl(lit.)
• Absorption Wavelength: ε1mM/445 nm 12.5
• pH: 5.5-7.0 (0.1 g/mL in H2O)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ~85% (HPLC); ≥70%; ≥70% (HPLC); 73-79% (fluorimetric)
• Grade: for electrophoresis
• Suitability: meets USP testing specifications; suitable for acrylamide photopolymerization
• Impurities: ≤0.3% Riboflavin; ≤1.5% free phosphate; ≤7% free riboflavin (HPLC); ≤7% riboflavin 5′-adenosine diphosphate (HPLC)
• Foreign Activity: Protease, none detected
• Biological Source: synthetic
• Loss on Drying: ≤7% loss on drying
• Empirical Formula (Hill Notation): C17H20N4NaO9P · xH2O

DETAILS

Sigma Aldrich - F6750

Quality
Free Riboflavin: ≤6.0%Riboflavin diphosphates: ≤6.0% (as riboflavin)
Application
Riboflavin 5′-monophosphate (FMN) is used as a prosthetic group by oxidoreductase (one and two electron transfer) enzymes such as NADH dehydrogenases, nitric oxide synthases, and nitrilotriacetate monooxygenases. Riboflavin 5′-monophosphate is used as a substrate to study the specificity and kinetics of FMN phosphohydrolases. FMN is used to study molecular sensing based gene regulation by riboswitches.

Sigma Aldrich - F2253

Biochem/physiol Actions
在益生菌（ATCC 菌株 7469）的生长中具有生物学活性。
Application
Riboflavin 5′-monophosphate (FMN) is used as a prosthetic group by oxidoreductase (one and two electron transfer) enzymes such as NADH dehydrogenase, nitric oxide synthase, and nitrilotriacetate monooxygenase. Riboflavin 5′-monophosphate is used as a substrate to study the specificity and kinetics of FMN phosphohydrolases and to study molecular sensing based gene regulation by riboswitches.

Sigma Aldrich - F1392

Application
FMN is suitable as a photopolymerization reagent in PAGE by forming free radicals in aqueous solution in the presence of light. FMN photodecomposes to leucoflavin. No free radicals are formed in the absence of oxygen, but traces of oxygen allow for leucoflavin to reoxidize with free-radical generation. The catalysts, TEMED or DMAPN, are commonly added to speed up the free radical formation. Free radicals will cause acrylamide and bis-acrylamide to polymerize to form a gel matrix which can be used for sieving macromolecules. FMN is commonly used in the stacking gel for non-denaturing PAGE because native proteins can be sensitive to persulfate ions from ammonium persulfate. Another advantage of FMN over ammonium persulfate is that it will not start polymerizing until the gel is illuminated.

Sigma Aldrich - 83810

Other Notes
Chemical and enzymatic properties of FMN1; Review: Flavin Coenzymes: At the crossroads of biological redox chemistry2; Riboflavin-mediated photopolymerization of acrylamide investigated by capillary zone electrophoresis3,4