2.0 2012-10-10 12:17:32 -0600 2015-06-03 17:25:58 -0600 ECMDB23122 M2MDB003512 1-Deoxy-L-glycero-tetrulose 4-phosphate 1-deoxy-L-glycero-tetrulose 4-phosphate is an intermediate in the synthesis of riboflavin. It is a substrate for the enzyme 6,7-dimethyl-8-ribityllumazine synthase (RibE) which catalyzes the formation of 6,7-dimethyl-8 ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 1-deoxy-L-glycero-tetrulose 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin. (2-hydroxy-3-oxobutyl) dihydrogen phosphate (2-Hydroxy-3-oxobutyl) dihydrogen phosphoric acid 1-Deoxy-L-glycero-tetrulose 4-phosphoric acid 2-Hydroxy-3-oxobutyl dihydrogen phosphate 2-Hydroxy-3-oxobutyl dihydrogen phosphoric acid 2-Hydroxy-3-oxobutyl phosphate 2-Hydroxy-3-oxobutyl phosphoric acid 3,4-Dihydroxy-2-butanone 4-phosphate 3,4-Dihydroxy-2-butanone 4-phosphoric acid L-3,4-Dihydroxybutan-2-one 4-phosphate L-3,4-Dihydroxybutan-2-one 4-phosphoric acid C4H9O6P 184.0844 184.013674532 (2-hydroxy-3-oxobutoxy)phosphonic acid 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) OKYHYXLCTGGOLM-UHFFFAOYSA-N logp -1.62 ALOGPS logs -0.87 ALOGPS solubility 2.49e+01 g/l ALOGPS logp -1.3 ChemAxon pka_strongest_acidic 1.39 ChemAxon pka_strongest_basic -3.8 ChemAxon iupac (2-hydroxy-3-oxobutoxy)phosphonic acid ChemAxon average_mass 184.0844 ChemAxon mono_mass 184.013674532 ChemAxon smiles CC(=O)C(O)COP(O)(O)=O ChemAxon formula C4H9O6P ChemAxon inchi InChI=1S/C4H9O6P/c1-3(5)4(6)2-10-11(7,8)9/h4,6H,2H2,1H3,(H2,7,8,9) ChemAxon inchikey OKYHYXLCTGGOLM-UHFFFAOYSA-N ChemAxon polar_surface_area 104.06 ChemAxon refractivity 34.81 ChemAxon polarizability 14.38 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon 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 Specdb::CMs 3053 Specdb::NmrOneD 290555 Specdb::NmrOneD 290556 Specdb::NmrOneD 290557 Specdb::NmrOneD 290558 Specdb::NmrOneD 290559 Specdb::NmrOneD 290560 Specdb::NmrOneD 290561 Specdb::NmrOneD 290562 Specdb::NmrOneD 290563 Specdb::NmrOneD 290564 Specdb::NmrOneD 290565 Specdb::NmrOneD 290566 Specdb::NmrOneD 290567 Specdb::NmrOneD 290568 Specdb::NmrOneD 290569 Specdb::NmrOneD 290570 Specdb::NmrOneD 290571 Specdb::NmrOneD 290572 Specdb::NmrOneD 290573 Specdb::NmrOneD 290574 Specdb::MsMs 25145 Specdb::MsMs 25146 Specdb::MsMs 25147 Specdb::MsMs 31703 Specdb::MsMs 31704 Specdb::MsMs 31705 Specdb::MsMs 3607813 Specdb::MsMs 3607814 Specdb::MsMs 3607815 Specdb::MsMs 3607816 Specdb::MsMs 3607817 Specdb::MsMs 3607818 669 C15556 50608 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 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase Q46893 ISPD_ECOLI ispD http://ecmdb.ca/proteins/Q46893.xml D-Ribulose 5-phosphate > Formic acid + 1-Deoxy-L-glycero-tetrulose 4-phosphate D-Ribulose 5-phosphate > 1-Deoxy-L-glycero-tetrulose 4-phosphate + Formic acid + Hydrogen ion PW_R003846 5-Amino-6-ribitylamino uracil + 1-Deoxy-L-glycero-tetrulose 4-phosphate > Water + Phosphate + Hydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine + 6,7-Dimethyl-8-(1-D-ribityl)lumazine PW_R005556