2.0 2012-05-31 09:57:14 -0600 2015-09-13 12:56:06 -0600 ECMDB00097 M2MDB000036 Choline Choline is a trimethylammonium compound. Choine can be used as a substrate by bacteria to generate osmoprotectants. Choline dehydrogenase (CHD) catalyzes the first step in the biosynthesis of the osmoprotectant glycine betaine from choline. CHD is associated with the membrane, is electron transfer-linked and oxygen dependent. (2-Hydroxyethyl)trimethyl ammonium (2-Hydroxyethyl)trimethylammonium (b-Hydroxyethyl)trimethylammonium (beta-hydroxyethyl)trimethylammonium (β-Hydroxyethyl)trimethylammonium 2-Hydroxy-N,N,N-trimethyl-ethanaminium 2-Hydroxy-N,N,N-trimethylethanaminium Bilineurine Biocolina Biocoline Choline Choline cation Choline ion Cholinum Hepacholine Hormocline Lipotril N,N,N-Trimethylethanol-ammonium N,N,N-Trimethylethanolammonium Neocolina Paresan C5H14NO 104.1708 104.107539075 (2-hydroxyethyl)trimethylazanium choline 62-49-7 C[N+](C)(C)CCO InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1 OEYIOHPDSNJKLS-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -3.59 ALOGPS logs -1.59 ALOGPS solubility 3.61e+00 g/l ALOGPS melting_point 302-303 oC (Chloride salt) logp -4.7 ChemAxon pka_strongest_acidic 13.97 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (2-hydroxyethyl)trimethylazanium ChemAxon average_mass 104.1708 ChemAxon mono_mass 104.107539075 ChemAxon smiles C[N+](C)(C)CCO ChemAxon formula C5H14NO ChemAxon inchi InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1 ChemAxon inchikey OEYIOHPDSNJKLS-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 42.19 ChemAxon polarizability 12.57 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 1 ChemAxon Glycine, serine and threonine metabolism ec00260 Glycerophospholipid metabolism ec00564 ABC transporters ec02010 Metabolic pathways eco01100 glycine betaine biosynthesis I (Gram-negative bacteria) BETSYN-PWY Specdb::CMs 2793 Specdb::CMs 37292 Specdb::CMs 165427 Specdb::CMs 1049952 Specdb::NmrOneD 1082 Specdb::NmrOneD 1143 Specdb::NmrOneD 142150 Specdb::NmrOneD 142151 Specdb::NmrOneD 142152 Specdb::NmrOneD 142153 Specdb::NmrOneD 142154 Specdb::NmrOneD 142155 Specdb::NmrOneD 142156 Specdb::NmrOneD 142157 Specdb::NmrOneD 142158 Specdb::NmrOneD 142159 Specdb::NmrOneD 142160 Specdb::NmrOneD 142161 Specdb::NmrOneD 142162 Specdb::NmrOneD 142163 Specdb::NmrOneD 142164 Specdb::NmrOneD 142165 Specdb::NmrOneD 142166 Specdb::NmrOneD 142167 Specdb::NmrOneD 142168 Specdb::NmrOneD 142169 Specdb::NmrOneD 166459 Specdb::NmrOneD 166460 Specdb::MsMs 150 Specdb::MsMs 151 Specdb::MsMs 152 Specdb::MsMs 2860 Specdb::MsMs 2861 Specdb::MsMs 316963 Specdb::MsMs 316964 Specdb::MsMs 316965 Specdb::MsMs 445344 Specdb::MsMs 445345 Specdb::MsMs 447331 Specdb::MsMs 448183 Specdb::MsMs 448184 Specdb::MsMs 451952 Specdb::MsMs 2912294 Specdb::MsMs 2912295 Specdb::MsMs 2912296 Specdb::NmrTwoD 955 Specdb::NmrTwoD 1140 HMDB00097 305 299 C00114 15354 CHOLINE CHT Choline Keseler, I. 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Kokai Tokkyo Koho (1999), 9 pp. http://hmdb.ca/system/metabolites/msds/000/000/067/original/HMDB00097.pdf?1358462190 Glycerophosphoryl diester phosphodiesterase P09394 GLPQ_ECOLI glpQ http://ecmdb.ca/proteins/P09394.xml Glycerophosphoryl diester phosphodiesterase_ P10908 UGPQ_ECOLI ugpQ http://ecmdb.ca/proteins/P10908.xml Choline dehydrogenase P17444 BETA_ECOLI betA http://ecmdb.ca/proteins/P17444.xml Putative osmoprotectant uptake system permease protein yehW P33359 YEHW_ECOLI yehW http://ecmdb.ca/proteins/P33359.xml Putative osmoprotectant uptake system permease protein yehY P33361 YEHY_ECOLI yehY http://ecmdb.ca/proteins/P33361.xml Putative osmoprotectant uptake system ATP-binding protein yehX P33360 YEHX_ECOLI yehX http://ecmdb.ca/proteins/P33360.xml Putative osmoprotectant uptake system substrate-binding protein osmF P33362 OSMF_ECOLI osmF http://ecmdb.ca/proteins/P33362.xml Uncharacterized transporter YeaV P0ABD1 YEAV_ECOLI yeaV http://ecmdb.ca/proteins/P0ABD1.xml Putative osmoprotectant uptake system permease protein yehW P33359 YEHW_ECOLI yehW http://ecmdb.ca/proteins/P33359.xml Putative osmoprotectant uptake system permease protein yehY P33361 YEHY_ECOLI yehY http://ecmdb.ca/proteins/P33361.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml High-affinity choline transport protein P0ABC9 BETT_ECOLI betT http://ecmdb.ca/proteins/P0ABC9.xml Putative osmoprotectant uptake system ATP-binding protein yehX P33360 YEHX_ECOLI yehX http://ecmdb.ca/proteins/P33360.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 Putative osmoprotectant uptake system substrate-binding protein osmF P33362 OSMF_ECOLI osmF http://ecmdb.ca/proteins/P33362.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Adenosine triphosphate + Water + Choline > ADP + Choline + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Choline > ADP + Choline + Hydrogen ion + Phosphate Choline + NAD > Betaine aldehyde + Hydrogen ion + NADH Glycerophosphocholine + Water > Choline + Glycerol 3-phosphate + Hydrogen ion Choline + Acceptor + Acceptor <> Betaine aldehyde + Reduced acceptor + Reduced acceptor R01025 Glycerophosphocholine + Water <> Choline + Glycerol 3-phosphate R01030 Choline + an oxidized electron acceptor > Betaine aldehyde + a reduced electron acceptor CHD-RXN Choline + acceptor > Betaine aldehyde + reduced acceptor Glycerophosphocholine + Water > Choline + Glycerol 3-phosphate + Hydrogen ion Choline + Acceptor <> Betaine aldehyde + Reduced acceptor Glycerophosphocholine + Water > Choline + Glycerol 3-phosphate + Hydrogen ion Choline + Acceptor <> Betaine aldehyde + Reduced acceptor