2.0 2012-08-09 09:16:14 -0600 2015-06-03 17:21:29 -0600 ECMDB21434 M2MDB001829 Mannitol 1-phosphate Mannitol-1-phosphate is a sugar alcohol. Mannitol-1-phosphate dehydrogenase (EC 1.1.1.17) reduces fructose 6-phosphate into mannitol 1-phosphate, in the mannitol cycle of organisms such as Lactobacillus plantarum, a lactic acid bacterium found in many fermented food products and in the gastrointestinal tract of mammals. (HMDB) This redox reaction also occurs in E. coli, catalyzed by mannitol-1-phosphate 5-dehydrogenase which is encoded by gene mtlD. (EcoCyc) In E. coli, the transport of mannitol into the cell is done through a phosphotransferase system which attaches a phosphate to mannitol, producing mannitol 1-phosphate. (KEGG) D-Mannitol-1-phosphate D-Mannitol-1-phosphoric acid D-Mannitol-6-phosphate D-Mannitol-6-phosphoric acid Mannitol 1-phosphoric acid Mannitol-1-P Mannitol-1-phosphate Mannitol-1-phosphoric acid Mannitol-6-P Mant1P C6H15O9P 262.1517 262.04536859 {[(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]oxy}phosphonic acid mannitol-1-phosphate 15806-48-1 OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O InChI=1S/C6H15O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3-11H,1-2H2,(H2,12,13,14)/t3-,4-,5-,6-/m1/s1 GACTWZZMVMUKNG-KVTDHHQDSA-N Solid logp -2.32 ALOGPS logs -0.99 ALOGPS solubility 2.66e+01 g/l ALOGPS logp -3.9 ChemAxon pka_strongest_acidic 1.49 ChemAxon pka_strongest_basic -3 ChemAxon iupac {[(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]oxy}phosphonic acid ChemAxon average_mass 262.1517 ChemAxon mono_mass 262.04536859 ChemAxon smiles OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O ChemAxon formula C6H15O9P ChemAxon inchi InChI=1S/C6H15O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3-11H,1-2H2,(H2,12,13,14)/t3-,4-,5-,6-/m1/s1 ChemAxon inchikey GACTWZZMVMUKNG-KVTDHHQDSA-N ChemAxon polar_surface_area 167.91 ChemAxon refractivity 49.28 ChemAxon polarizability 21.53 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 8 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Fructose and mannose metabolism ec00051 glycolysis and pyruvate dehydrogenase Fructose metabolism begins with the transport of Beta-D-glucose 6-phosphate through a glucose PTS permease, resulting in a Beta-D-glucose 6-phosphate. This compound is isomerized by a glucose-6-phosphate isomerase resulting in a fructose 6-phosphate. This compound can be phosphorylated by two different enzymes, a pyridoxal phosphatase/fructose 1,6-bisphosphatase or a ATP driven-6-phosphofructokinase-1 resulting in a fructose 1,6-biphosphate. This compound can either react with a fructose bisphosphate aldolase class 1 resulting in D-glyceraldehyde 3-phosphate and a dihydroxyacetone phosphate or through a fructose biphosphate aldolase class 2 resulting in a D-glyceraldehyde 3-phosphate. This compound can then either react in a reversible triosephosphate isomerase resulting in a dihydroxyacetone phosphate or react with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000785 Metabolic Specdb::CMs 11955 Specdb::CMs 38108 Specdb::CMs 156723 Specdb::NmrOneD 148060 Specdb::NmrOneD 148061 Specdb::NmrOneD 148062 Specdb::NmrOneD 148063 Specdb::NmrOneD 148064 Specdb::NmrOneD 148065 Specdb::NmrOneD 148066 Specdb::NmrOneD 148067 Specdb::NmrOneD 148068 Specdb::NmrOneD 148069 Specdb::NmrOneD 148070 Specdb::NmrOneD 148071 Specdb::NmrOneD 148072 Specdb::NmrOneD 148073 Specdb::NmrOneD 148074 Specdb::NmrOneD 148075 Specdb::NmrOneD 148076 Specdb::NmrOneD 148077 Specdb::NmrOneD 148078 Specdb::NmrOneD 148079 Specdb::MsMs 27740 Specdb::MsMs 27741 Specdb::MsMs 27742 Specdb::MsMs 34298 Specdb::MsMs 34299 Specdb::MsMs 34300 Specdb::MsMs 446460 Specdb::MsMs 446461 Specdb::MsMs 446462 Specdb::MsMs 446463 Specdb::MsMs 446464 Specdb::MsMs 1472513 Specdb::MsMs 1472514 Specdb::MsMs 1472515 Specdb::MsMs 1472516 Specdb::MsMs 1472517 Specdb::MsMs 1472518 Specdb::MsMs 1472519 Specdb::MsMs 1472520 Specdb::MsMs 1472521 Specdb::MsMs 1472522 Specdb::MsMs 1472523 Specdb::MsMs 1472524 Specdb::MsMs 1472525 Specdb::MsMs 1472526 HMDB01530 130418 115387 C00644 16298 MANNITOL-1P 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 PTS system mannitol-specific EIICBA component P00550 PTM3C_ECOLI mtlA http://ecmdb.ca/proteins/P00550.xml Mannitol-1-phosphate 5-dehydrogenase P09424 MTLD_ECOLI mtlD http://ecmdb.ca/proteins/P09424.xml Mannitol-specific cryptic phosphotransferase enzyme IIA component P69824 PTMA_ECOLI cmtB http://ecmdb.ca/proteins/P69824.xml PTS system mannitol-specific cryptic EIICB component P69826 PTMCB_ECOLI cmtA http://ecmdb.ca/proteins/P69826.xml PTS system mannitol-specific EIICBA component P00550 PTM3C_ECOLI mtlA http://ecmdb.ca/proteins/P00550.xml PTS system mannitol-specific cryptic EIICB component P69826 PTMCB_ECOLI cmtA http://ecmdb.ca/proteins/P69826.xml Mannitol 1-phosphate + NAD > Fructose 6-phosphate + NADH Mannitol 1-phosphate + NAD <> Fructose 6-phosphate + NADH + Hydrogen ion R00758 Fructose 6-phosphate + NADH + Hydrogen ion + Fructose 6-phosphate <> NAD + Mannitol 1-phosphate PW_R005148 Mannitol + HPr - phosphorylated > Mannitol 1-phosphate + HPr PW_RCT000171