Riboflavin (ECMDB00244) (M2MDB000103)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 10:24:45 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:07 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Riboflavin | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Riboflavin, also known as vitamin B2, is the central component of the cofactors FAD and FMN, and is therefore required by all flavoproteins. As such, vitamin B2 is required for a wide variety of cellular processes. Like the other B vitamins, it plays a key role in energy metabolism, and is required for the metabolism of fats, ketone bodies, carbohydrates, and proteins. (Wikipedia) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C17H20N4O6 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 376.3639 Monoisotopic: 376.138284392 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | AUNGANRZJHBGPY-SCRDCRAPSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 83-88-5 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | riboflavin | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organoheterocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Pteridines and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Alloxazines and isoalloxazines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Flavins | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 290 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Hydrogen ion + NADPH + Riboflavin > NADP + Reduced riboflavin Adenosine triphosphate + Riboflavin <> ADP + Flavin Mononucleotide + Hydrogen ion 2 6,7-Dimethyl-8-(1-D-ribityl)lumazine > 5-Amino-6-ribitylamino uracil + Riboflavin Hydrogen ion + NADH + Riboflavin > NAD + Reduced riboflavin 2 Ferroxamine + Reduced riboflavin >2 Iron +2 ferroxamine minus Fe(3) +2 Hydrogen ion + Riboflavin 2 6,7-Dimethyl-8-(1-D-ribityl)lumazine <> Riboflavin + 5-Amino-6-ribitylamino uracil Flavin Mononucleotide + Water <> Riboflavin + Phosphate Adenosine triphosphate + Riboflavin <> ADP + Flavin Mononucleotide Reduced riboflavin + NADP < Hydrogen ion + Riboflavin + NADPH Hydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine > 5-amino-6-(D-ribitylamino)uracil + Riboflavin Riboflavin + Adenosine triphosphate > Hydrogen ion + Flavin Mononucleotide + ADP Reduced riboflavin + NAD(P)<sup>+</sup> Riboflavin + NAD(P)H + Hydrogen ion Flavin Mononucleotide + Water > Riboflavin + Phosphate Reduced riboflavin + NAD(P)(+) > Riboflavin + NAD(P)H Adenosine triphosphate + Riboflavin > ADP + Flavin Mononucleotide 2 6,7-dimethyl-8-(D-ribityl)lumazine > Riboflavin + 5-amino-6-ribitylamino-2,4(1h,3h)-pyrimidinedione 6,7-Dimethyl-8-(1-D-ribityl)lumazine + Hydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine > Riboflavin + 5-Amino-6-ribitylamino uracil + Riboflavin Riboflavin + Adenosine triphosphate + Riboflavin > Adenosine diphosphate + Hydrogen ion + Flavin Mononucleotide + ADP Riboflavin + NADPH + 2 Hydrogen ion > Riboflavin reduced + NADP 2 6,7-Dimethyl-8-(1-D-ribityl)lumazine >5 5-Amino-6-ribitylamino uracil + Riboflavin Adenosine triphosphate + Riboflavin <> ADP + Flavin Mononucleotide + Hydrogen ion | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Tishler, Max; Pfister, Karl, III; Babson, R. D.; Ladenburg, Kurt; Fleming, Ann J. Reaction between o-aminoazo compounds and barbituric acid. A new synthesis of riboflavin. Journal of the American Chemical Society (1947), 69 1487-92. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in acid phosphatase activity
- Specific function:
- A phosphate monoester + H(2)O = an alcohol + phosphate
- Gene Name:
- appA
- Uniprot ID:
- P07102
- Molecular weight:
- 47056
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate. |
Myo-inositol hexakisphosphate + H(2)O = 1D-myo-inositol 1,2,3,5,6-pentakisphosphate + phosphate. |
- General function:
- Involved in acid phosphatase activity
- Specific function:
- Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
- Gene Name:
- aphA
- Uniprot ID:
- P0AE22
- Molecular weight:
- 26103
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Catalyzes the reduction of soluble flavins by reduced pyridine nucleotides. Seems to reduces the complexed Fe(3+) iron of siderophores to Fe(2+), thus releasing it from the chelator
- Gene Name:
- fre
- Uniprot ID:
- P0AEN1
- Molecular weight:
- 26242
Reactions
Reduced riboflavin + NAD(P)(+) = riboflavin + NAD(P)H. |
2 cob(II)alamin + NAD(+) = 2 aquacob(III)alamin + NADH. |
- General function:
- Involved in riboflavin synthase activity
- Specific function:
- Riboflavin synthase is a bifunctional enzyme complex catalyzing the formation of riboflavin from 5-amino-6-(1'-D)- ribityl-amino-2,4(1H,3H)-pyrimidinedione and L-3,4-dihydrohy-2- butanone-4-phosphate via 6,7-dimethyl-8-lumazine. The alpha subunit catalyzes the dismutation of 6,7-dimethyl-8-lumazine to riboflavin and 5-amino-6-(1'-D)-ribityl-amino-2,4(1H,3H)- pyrimidinedione
- Gene Name:
- ribE
- Uniprot ID:
- P0AFU8
- Molecular weight:
- 23445
Reactions
2 6,7-dimethyl-8-(1-D-ribityl)lumazine = riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine. |
- General function:
- Involved in FMN adenylyltransferase activity
- Specific function:
- ATP + riboflavin = ADP + FMN
- Gene Name:
- ribF
- Uniprot ID:
- P0AG40
- Molecular weight:
- 34734
Reactions
ATP + riboflavin = ADP + FMN. |
ATP + FMN = diphosphate + FAD. |
- General function:
- Involved in sulfite reductase (NADPH) activity
- Specific function:
- Component of the sulfite reductase complex that catalyzes the 6-electron reduction of sulfite to sulfide. This is one of several activities required for the biosynthesis of L- cysteine from sulfate
- Gene Name:
- cysI
- Uniprot ID:
- P17846
- Molecular weight:
- 63998
Reactions
H(2)S + 3 NADP(+) + 3 H(2)O = sulfite + 3 NADPH. |
- General function:
- Involved in sulfite reductase (NADPH) activity
- Specific function:
- Component of the sulfite reductase complex that catalyzes the 6-electron reduction of sulfite to sulfide. This is one of several activities required for the biosynthesis of L- cysteine from sulfate. The flavoprotein component catalyzes the electron flow from NADPH -> FAD -> FMN to the hemoprotein component
- Gene Name:
- cysJ
- Uniprot ID:
- P38038
- Molecular weight:
- 66269
Reactions
H(2)S + 3 NADP(+) + 3 H(2)O = sulfite + 3 NADPH. |
- General function:
- Involved in 2 iron, 2 sulfur cluster binding
- Specific function:
- Involved in the reduction of ferric iron in cytoplasmic ferrioxamine B
- Gene Name:
- fhuF
- Uniprot ID:
- P39405
- Molecular weight:
- 30113
- General function:
- Involved in riboflavin biosynthetic process
- Specific function:
- Riboflavin synthase is a bifunctional enzyme complex catalyzing the formation of riboflavin from 5-amino-6-(1'-D)- ribityl-amino-2,4(1H,3H)-pyrimidinedione and L-3,4-dihydrohy-2- butanone-4-phosphate via 6,7-dimethyl-8-lumazine. The beta subunit catalyzes the condensation of 5-amino-6-(1'-D)-ribityl-amino- 2,4(1H,3H)-pyrimidinedione with L-3,4-dihydrohy-2-butanone-4- phosphate yielding 6,7-dimethyl-8-lumazine
- Gene Name:
- ribH
- Uniprot ID:
- P61714
- Molecular weight:
- 16156
Reactions
2 6,7-dimethyl-8-(1-D-ribityl)lumazine = riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the dephosphorylation of the artificial chromogenic substrate p-nitrophenyl phosphate (pNPP) and of the natural substrates FMN and beta-glucose 1-phosphate
- Gene Name:
- ybjI
- Uniprot ID:
- P75809
- Molecular weight:
- 30196