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130-40-5(anhydrous) molecular structure
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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 and InChIs

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

Cite this record

CBID:130811 http://www.chembase.cn/molecule-130811.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 23679076 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 1.5655322  H Acceptors 11 
H Donor LogD (pH = 5.5) -3.4562092 
LogD (pH = 7.4) -4.8923903  Log P -1.1982645 
Molar Refractivity 106.0196 cm3 Polarizability 39.881233 Å3
Polar Surface Area 204.41 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble0.1 g/mL, clear, orange-yellow to very deep orange-red expand Show data source
Apperance
powder expand Show data source
Optical Rotation
[α]20/D +37 to +42°, c = 1.5 in 5 M HCl(lit.) expand Show data source
Absorption Wavelength
ε1mM/445 nm 12.5 expand Show data source
pH
5.5-7.0 (0.1 g/mL in H2O) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Purity
~85% (HPLC) expand Show data source
≥70% expand Show data source
≥70% (HPLC) expand Show data source
73-79% (fluorimetric) expand Show data source
Grade
for electrophoresis expand Show data source
Suitability
meets USP testing specifications expand Show data source
suitable for acrylamide photopolymerization expand Show data source
Impurities
≤0.3% Riboflavin expand Show data source
≤1.5% free phosphate expand Show data source
≤7% free riboflavin (HPLC) expand Show data source
≤7% riboflavin 5′-adenosine diphosphate (HPLC) expand Show data source
Foreign Activity
Protease, none detected expand Show data source
Biological Source
synthetic expand Show data source
Loss on Drying
≤7% loss on drying expand Show data source
Empirical Formula (Hill Notation)
C17H20N4NaO9P · xH2O expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - F6750 external link
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 external link
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 external link
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 external link
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

REFERENCES

REFERENCES

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PATENTS

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