2.0 2012-07-30 14:54:38 -0600 2015-06-03 17:20:38 -0600 ECMDB21100 M2MDB001509 (R)-Propane-1,2-diol Propylene glycol, also called 1,2-propanediol or propane-1,2-diol, is an organic compound, specifically, a diol or double alcohol. It is a colorless, nearly odorless, clear, viscous liquid, hygroscopic and miscible with water, acetone, and chloroform. Propylene glycol contains an asymmetrical carbon atom, so it exists in two stereoisomers. (Wikipedia) (2R)-propane-1,2-diol (R)-(-)-PROPANE-1,2-DIOL (R)-1,2-propanediol (R)-Propane-1,2-diol (R)-propylene glycol (S)-propane-1,2-diol 1,2-Dihydroxypropane 1,2-Propane-diol 1,2-Propanediol D-1,2-Propanediol Propanediol Propylene glycol R-1,2-PROPANEDIOL C3H8O2 76.0944 76.0524295 (2R)-propane-1,2-diol R-1,2-propanediol 4254-14-2 C[C@@H](O)CO InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m1/s1 DNIAPMSPPWPWGF-GSVOUGTGSA-N Cytosol Extra-organism Periplasm logp -1.10 ALOGPS logs 1.10 ALOGPS solubility 9.52e+02 g/l ALOGPS logp -0.79 ChemAxon pka_strongest_acidic 14.47 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac (2R)-propane-1,2-diol ChemAxon average_mass 76.0944 ChemAxon mono_mass 76.0524295 ChemAxon smiles C[C@@H](O)CO ChemAxon formula C3H8O2 ChemAxon inchi InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m1/s1 ChemAxon inchikey DNIAPMSPPWPWGF-GSVOUGTGSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 18.97 ChemAxon polarizability 8.01 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Pyruvate metabolism ec00620 Glyoxylate and dicarboxylate metabolism ec00630 Propanoate metabolism Starting from L-threonine, this compound is deaminated through a threonine deaminase resulting in a hydrogen ion, a water molecule and a (2z)-2-aminobut-2-enoate. The latter compound then isomerizes to a 2-iminobutanoate, This compound then reacts spontaneously with hydrogen ion and a water molecule resulting in a ammonium and a 2-Ketobutyric acid. The latter compound interacts with CoA through a pyruvate formate-lyase / 2-ketobutyrate formate-lyase resulting in a formic acid and a propionyl-CoA. Propionyl-CoA can then be processed either into a 2-methylcitric acid or into a propanoyl phosphate. Propionyl-CoA interacts with oxalacetic acid and a water molecule through a 2-methylcitrate synthase resulting in a hydrogen ion, a CoA and a 2-Methylcitric acid.The latter compound is dehydrated through a 2-methylcitrate dehydratase resulting in a water molecule and cis-2-methylaconitate. The latter compound is then dehydrated by a bifunctional aconitate hydratase 2 and 2-methylisocitrate dehydratase resulting in a water molecule and methylisocitric acid. The latter compound is then processed by 2-methylisocitrate lyase resulting in a release of succinic acid and pyruvic acid. Succinic acid can then interact with a propionyl-CoA through a propionyl-CoA:succinate CoA transferase resulting in a propionic acid and a succinyl CoA. Succinyl-CoA is then isomerized through a methylmalonyl-CoA mutase resulting in a methylmalonyl-CoA. This compound is then decarboxylated through a methylmalonyl-CoA decarboxylase resulting in a release of Carbon dioxide and Propionyl-CoA. ropionyl-CoA interacts with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. Propionyl-CoA can react with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. The latter compound is then dephosphorylated through a ADP driven acetate kinase/propionate kinase protein complex resulting in an ATP and Propionic acid. Propionic acid can be processed by a reaction with CoA through a ATP-driven propionyl-CoA synthetase resulting in a pyrophosphate, an AMP and a propionyl-CoA. PW000940 ec00640 Metabolic Microbial metabolism in diverse environments ec01120 Specdb::CMs 102837 Specdb::CMs 102838 Specdb::CMs 102839 Specdb::CMs 102840 Specdb::CMs 102841 Specdb::CMs 102842 Specdb::CMs 159349 Specdb::EiMs 2011 Specdb::NmrOneD 5264 Specdb::NmrOneD 5265 Specdb::NmrOneD 5266 Specdb::NmrOneD 5267 Specdb::NmrOneD 5268 Specdb::NmrOneD 9822 Specdb::NmrOneD 9823 Specdb::NmrOneD 9824 Specdb::NmrOneD 9825 Specdb::NmrOneD 9826 Specdb::NmrOneD 9827 Specdb::NmrOneD 9828 Specdb::NmrOneD 9829 Specdb::NmrOneD 9830 Specdb::NmrOneD 9831 Specdb::NmrOneD 9832 Specdb::NmrOneD 9833 Specdb::NmrOneD 9834 Specdb::NmrOneD 9835 Specdb::NmrOneD 9836 Specdb::NmrOneD 9837 Specdb::NmrOneD 9838 Specdb::NmrOneD 9839 Specdb::NmrOneD 9840 Specdb::NmrOneD 9841 Specdb::MsMs 23816 Specdb::MsMs 23817 Specdb::MsMs 23818 Specdb::MsMs 30614 Specdb::MsMs 30615 Specdb::MsMs 30616 Specdb::MsMs 1448608 Specdb::MsMs 1448609 Specdb::MsMs 1448610 Specdb::MsMs 1448611 Specdb::MsMs 1448612 Specdb::MsMs 2822372 Specdb::MsMs 2822373 Specdb::MsMs 2822374 Specdb::MsMs 2859781 Specdb::MsMs 2859782 Specdb::MsMs 2859783 Specdb::NmrTwoD 2076 259994 228188 C02912 28972 CPD-8891 PGR (R)-propane-1,2-diol Lactaldehyde reductase P0A9S1 FUCO_ECOLI fucO http://ecmdb.ca/proteins/P0A9S1.xml Glycerol dehydrogenase P0A9S5 GLDA_ECOLI gldA http://ecmdb.ca/proteins/P0A9S5.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Acetol + Hydrogen ion + NADH > (R)-Propane-1,2-diol + NAD (R)-Propane-1,2-diol + NAD > D-Lactaldehyde + NADH (R)-Propane-1,2-diol + (S)-Propane-1,2-diol + NAD <> D-Lactaldehyde + (S)-Lactaldehyde + NADH + Hydrogen ion R02258 R03080