2.0 2012-05-31 14:03:54 -0600 2015-06-03 15:54:41 -0600 ECMDB04060 M2MDB000590 3,4-Dihydroxy-2-butanone-4-P 3,4-dihydroxy-2-butanone-4-p is a member of the chemical class known as Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group. 3,4-dihydroxy-2-butanone-4-p is invovled in Fravin biosynthesis. r 15;80(8):2939-48.) 3,4-dihydroxy-2-butanone-4-P 3,4-Dihydroxy-2-butanone-4-phosphate 3,4-Dihydroxy-2-butanone-4-phosphoric acid 3,4D2B4P Dihydroxy-butanone-p L-3,4-Dihydroxybutan-2-one-4-phosphate L-3,4-Dihydroxybutan-2-one-4-phosphoric acid Tetrolose phosphate Tetrolose phosphoric acid C4H7O6P 182.0685 181.998024468 3-hydroxy-4-(phosphonatooxy)butan-2-one 2-hydroxy-3-oxobutyl phosphate CC(=O)C(O)COP([O-])([O-])=O InChI=1S/C4H9O6P/c1-3(5)4(6)2-10-11(7,8)9/h4,6H,2H2,1H3,(H2,7,8,9)/p-2 OKYHYXLCTGGOLM-UHFFFAOYSA-L Cytosol logp -1.20 ALOGPS logs -0.56 ALOGPS solubility 6.05e+01 g/l ALOGPS logp -1.3 ChemAxon pka_strongest_acidic 1.39 ChemAxon pka_strongest_basic -3.8 ChemAxon iupac 3-hydroxy-4-(phosphonatooxy)butan-2-one ChemAxon average_mass 182.0685 ChemAxon mono_mass 181.998024468 ChemAxon smiles CC(=O)C(O)COP([O-])([O-])=O ChemAxon formula C4H7O6P ChemAxon inchi InChI=1S/C4H9O6P/c1-3(5)4(6)2-10-11(7,8)9/h4,6H,2H2,1H3,(H2,7,8,9)/p-2 ChemAxon inchikey OKYHYXLCTGGOLM-UHFFFAOYSA-L ChemAxon polar_surface_area 109.72 ChemAxon refractivity 32.56 ChemAxon polarizability 14.04 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 1 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 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::NmrOneD 283309 Specdb::NmrOneD 283310 Specdb::NmrOneD 283311 Specdb::NmrOneD 283312 Specdb::NmrOneD 283313 Specdb::NmrOneD 283314 Specdb::NmrOneD 283315 Specdb::NmrOneD 283316 Specdb::NmrOneD 283317 Specdb::NmrOneD 283318 Specdb::NmrOneD 283319 Specdb::NmrOneD 283320 Specdb::NmrOneD 283321 Specdb::NmrOneD 283322 Specdb::NmrOneD 283323 Specdb::NmrOneD 283324 Specdb::NmrOneD 283325 Specdb::NmrOneD 283326 Specdb::NmrOneD 283327 Specdb::NmrOneD 283328 Specdb::MsMs 24944 Specdb::MsMs 24945 Specdb::MsMs 24946 Specdb::MsMs 31502 Specdb::MsMs 31503 Specdb::MsMs 31504 21983291 10739351 C15556 50606 DIHYDROXY-BUTANONE-P 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). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 3,4-dihydroxy-2-butanone 4-phosphate synthase P0A7J0 RIBB_ECOLI ribB http://ecmdb.ca/proteins/P0A7J0.xml Riboflavin synthase alpha chain P0AFU8 RISA_ECOLI ribE http://ecmdb.ca/proteins/P0AFU8.xml 6,7-dimethyl-8-ribityllumazine synthase P61714 RISB_ECOLI ribH http://ecmdb.ca/proteins/P61714.xml 5-Amino-6-ribitylamino uracil + 3,4-Dihydroxy-2-butanone-4-P > 6,7-Dimethyl-8-(1-D-ribityl)lumazine +2 Water + Phosphate R04457 D-Ribulose 5-phosphate <> 3,4-Dihydroxy-2-butanone-4-P + Formic acid + Hydrogen ion R07281 DIOHBUTANONEPSYN-RXN 5-Amino-6-ribitylamino uracil + 3,4-Dihydroxy-2-butanone-4-P <> 6,7-Dimethyl-8-(1-D-ribityl)lumazine +2 Water + Phosphate R04457 D-Ribulose 5-phosphate <> 3,4-Dihydroxy-2-butanone-4-P + Formic acid R07281 D-Ribulose 5-phosphate > Hydrogen ion + 3,4-Dihydroxy-2-butanone-4-P + Formic acid DIOHBUTANONEPSYN-RXN 5-amino-6-(D-ribitylamino)uracil + 3,4-Dihydroxy-2-butanone-4-P > Hydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine + Phosphate + Water LUMAZINESYN-RXN D-Ribulose 5-phosphate <>3 3,4-Dihydroxy-2-butanone-4-P + Formic acid + Hydrogen ion D-Ribulose 5-phosphate <>3 3,4-Dihydroxy-2-butanone-4-P + Formic acid D-Ribulose 5-phosphate <>3 3,4-Dihydroxy-2-butanone-4-P + Formic acid + Hydrogen ion