2.0 2012-05-31 10:24:45 -0600 2015-09-13 12:56:07 -0600 ECMDB00244 M2MDB000103 Riboflavin 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) (-)-Riboflavin 1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol 6,7-Dimethyl-9-D-ribitylisoalloxazine 6,7-Dimethyl-9-ribitylisoalloxazine 7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-Benzo[g]pteridine-2,4(3H,10H)-dione Beflavin Beflavine Benzo[g]pteridine riboflavin deriv. E 101 Flavaxin Flavin BB Flaxain Food Yellow 15 Hyre Lactobene Lactoflavin Lactoflavine Ribipca Ribocrisina Riboderm Riboflavine Ribosyn Ribotone Ribovel Russupteridine yellow I Russupteridine yellow III San Yellow B Vitaflavine Vitamin B2 Vitamin B₂ Vitamin G Vitasan B2 C17H20N4O6 376.3639 376.138284392 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione riboflavin 83-88-5 CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1 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 AUNGANRZJHBGPY-SCRDCRAPSA-N Solid Cytosol logp -1.05 ALOGPS logs -2.76 ALOGPS solubility 6.57e-01 g/l ALOGPS melting_point 290 oC logp -0.92 ChemAxon pka_strongest_acidic 5.97 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione ChemAxon average_mass 376.3639 ChemAxon mono_mass 376.138284392 ChemAxon 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 ChemAxon formula C17H20N4O6 ChemAxon 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 ChemAxon inchikey AUNGANRZJHBGPY-SCRDCRAPSA-N ChemAxon polar_surface_area 155.05 ChemAxon refractivity 96.27 ChemAxon polarizability 37.51 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Riboflavin metabolism ec00740 Metabolic pathways eco01100 Flavin biosynthesis The process of flavin biosynthesis starts with GTP being metabolized by interacting with 3 molecules of water through a GTP cyclohydrolase resulting in a release of formic acid, a pyrophosphate, two hydrog ions and 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one or 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine. Either of these compounds interacts with a water molecule and a hydrogen ion through a fused diaminohydroxyphosphoribosylaminopyrimidine deaminase / 5-amino-6-(5-phosphoribosylamino)uracil reductase resulting in an ammonium and 5-amino-6-(5-phospho-D-ribosylamino)uracil. This compound then interacts with a hydrogen ion through a NADPH dependent fused diaminohydroxyphosphoribosylaminopyrimidine deaminase / 5-amino-6-(5-phosphoribosylamino)uracil reductase resulting in the release of a NADP and a 5-amino-6-(5-phospho-D-ribitylamino)uracil. This compound then interacts with a water molecule through a 5-amino-6-(5-phospho-D-ribitylamino)uracil phosphatase resulting in a release of a phosphate, and a 5-amino-6-(D-ribitylamino)uracil. D-ribulose 5-phosphate interacts with a3,4-dihydroxy-2-butanone 4-phosphate synthase resulting in the release of formic acid, a hydrogen ion and 1-deoxy-L-glycero-tetrulose 4-phosphate. A 5-amino-6-(D-ribitylamino)uracil and 1-deoxy-L-glycero-tetrulose 4-phosphate interact through a 6,7-dimethyl-8-ribityllumazine synthase resulting in the release of 2 water molecules, a phosphate, a hydrogen ion and a 6,7-dimethyl-8-(1-D-ribityl)lumazine. The latter compound then interacts with a hydrogen ion through a riboflavin synthase resulting in the release of a riboflavin and a 5-amino-6-(d-ribitylamino)uracil. The riboflavin is then phosphorylated through an ATP dependent riboflavin kinase resulting in the release of a ADP, a hydrogen ion and a FLAVIN MONONUCLEOTIDE. The flavin mononucleotide interad with a hydrogen ion and an ATP through the riboflavin kinase resulting in the release of a pyrophosphate and Flavin Adenine dinucleotide. This compound is then exported into the periplasm through a FMN/FAD exporter. PW001971 Metabolic flavin biosynthesis I (bacteria and plants) RIBOSYN2-PWY Specdb::CMs 10276 Specdb::CMs 29895 Specdb::CMs 37383 Specdb::CMs 99553 Specdb::CMs 148319 Specdb::CMs 1055182 Specdb::CMs 1055183 Specdb::CMs 1055185 Specdb::CMs 1055187 Specdb::CMs 1055189 Specdb::CMs 1055191 Specdb::CMs 1055193 Specdb::CMs 1055195 Specdb::CMs 1055197 Specdb::CMs 1055199 Specdb::CMs 1055201 Specdb::CMs 1055203 Specdb::CMs 1055205 Specdb::CMs 1055206 Specdb::CMs 1055208 Specdb::CMs 1055210 Specdb::CMs 1055212 Specdb::CMs 1055214 Specdb::CMs 1055216 Specdb::CMs 1055218 Specdb::NmrOneD 1268 Specdb::NmrOneD 143170 Specdb::NmrOneD 143171 Specdb::NmrOneD 143172 Specdb::NmrOneD 143173 Specdb::NmrOneD 143174 Specdb::NmrOneD 143175 Specdb::NmrOneD 143176 Specdb::NmrOneD 143177 Specdb::NmrOneD 143178 Specdb::NmrOneD 143179 Specdb::NmrOneD 143180 Specdb::NmrOneD 143181 Specdb::NmrOneD 143182 Specdb::NmrOneD 143183 Specdb::NmrOneD 143184 Specdb::NmrOneD 143185 Specdb::NmrOneD 143186 Specdb::NmrOneD 143187 Specdb::NmrOneD 143188 Specdb::NmrOneD 143189 Specdb::MsMs 3737 Specdb::MsMs 439241 Specdb::MsMs 439535 Specdb::MsMs 439536 Specdb::MsMs 439733 Specdb::MsMs 2226570 Specdb::MsMs 2231229 Specdb::MsMs 2231301 Specdb::MsMs 2232918 Specdb::MsMs 2232951 Specdb::MsMs 2233613 Specdb::MsMs 2233669 Specdb::MsMs 2235291 Specdb::MsMs 2235304 Specdb::MsMs 2252521 Specdb::MsMs 2253947 Specdb::MsMs 412 Specdb::MsMs 413 Specdb::MsMs 414 Specdb::MsMs 3736 Specdb::MsMs 374336 Specdb::MsMs 448178 Specdb::MsMs 449588 Specdb::MsMs 449589 Specdb::MsMs 449590 Specdb::NmrTwoD 1234 HMDB00244 6759 431981 C00255 17015 RIBOFLAVIN RBF Riboflavin Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). 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Reaction between o-aminoazo compounds and barbituric acid. A new synthesis of riboflavin. Journal of the American Chemical Society (1947), 69 1487-92. http://hmdb.ca/system/metabolites/msds/000/000/178/original/HMDB00244.pdf?1358895546 Periplasmic AppA protein P07102 PPA_ECOLI appA http://ecmdb.ca/proteins/P07102.xml Class B acid phosphatase P0AE22 APHA_ECOLI aphA http://ecmdb.ca/proteins/P0AE22.xml NAD(P)H-flavin reductase P0AEN1 FRE_ECOLI fre http://ecmdb.ca/proteins/P0AEN1.xml Riboflavin synthase alpha chain P0AFU8 RISA_ECOLI ribE http://ecmdb.ca/proteins/P0AFU8.xml Riboflavin biosynthesis protein ribF P0AG40 RIBF_ECOLI ribF http://ecmdb.ca/proteins/P0AG40.xml Sulfite reductase [NADPH] hemoprotein beta-component P17846 CYSI_ECOLI cysI http://ecmdb.ca/proteins/P17846.xml Sulfite reductase [NADPH] flavoprotein alpha-component P38038 CYSJ_ECOLI cysJ http://ecmdb.ca/proteins/P38038.xml Ferric iron reductase protein fhuF P39405 FHUF_ECOLI fhuF http://ecmdb.ca/proteins/P39405.xml 6,7-dimethyl-8-ribityllumazine synthase P61714 RISB_ECOLI ribH http://ecmdb.ca/proteins/P61714.xml Phosphatase ybjI P75809 YBJI_ECOLI ybjI http://ecmdb.ca/proteins/P75809.xml Hydrogen ion + NADPH + Riboflavin > NADP + Reduced riboflavin NADPH-DEHYDROGENASE-FLAVIN-RXN Adenosine triphosphate + Riboflavin <> ADP + Flavin Mononucleotide + Hydrogen ion R00549 RIBOFLAVINKIN-RXN 2 6,7-Dimethyl-8-(1-D-ribityl)lumazine > 5-Amino-6-ribitylamino uracil + Riboflavin R00066 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 R00066 Flavin Mononucleotide + Water <> Riboflavin + Phosphate R00548 RXN0-5187 Adenosine triphosphate + Riboflavin <> ADP + Flavin Mononucleotide R00549 Reduced riboflavin + NADP < Hydrogen ion + Riboflavin + NADPH NADPH-DEHYDROGENASE-FLAVIN-RXN Hydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine > 5-amino-6-(D-ribitylamino)uracil + Riboflavin RIBOFLAVIN-SYN-RXN Riboflavin + Adenosine triphosphate > Hydrogen ion + Flavin Mononucleotide + ADP RIBOFLAVINKIN-RXN Reduced riboflavin + NAD(P)⁺ Riboflavin + NAD(P)H + Hydrogen ion RXN-12445 Flavin Mononucleotide + Water > Riboflavin + Phosphate RXN0-5187 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 PW_R005563 Riboflavin + Adenosine triphosphate + Riboflavin > Adenosine diphosphate + Hydrogen ion + Flavin Mononucleotide + ADP PW_R005564 Riboflavin + NADPH + 2 Hydrogen ion > Riboflavin reduced + NADP PW_R005914 2 6,7-Dimethyl-8-(1-D-ribityl)lumazine >5 5-Amino-6-ribitylamino uracil + Riboflavin Adenosine triphosphate + Riboflavin <> ADP + Flavin Mononucleotide + Hydrogen ion Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 19.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 76000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Shake flask and filter culture 22.1 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 88400 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Shake flask and filter culture 18.8 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 75200 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621