2.0 2012-10-24 09:54:58 -0600 2015-12-09 12:06:46 -0700 ECMDB23674 M2MDB004064 PG(14:0(3-OH)/15:0cyclo) PG(14:0(3-OH)/15:0cyclo) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(14:0(3-OH)/15:0cyclo), in particular, consists of one 3-hydroxytetradecanoyl chain to the C-1 atom, and one cis-9,10-Methylenetetradecanoic acid to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes. 1-3-hydroxytetradecanoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phospho-(1'-glycerol) 1-3-hydroxytetradecanoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phosphoglycerol 1-3-hydroxytetradecanoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phosphoglycerol GPG(14:0/15:0) GPG(29:0) PG(14:0/15:0) PG(29:0) Phosphatidylglycerol(14:0/15:0) Phosphatidylglycerol(29:0) C35H67O11P 694.884 694.442099975 [(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxytetradecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid (2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxytetradecanoyl)oxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CC(O)CCCCCCCCCCC InChI=1S/C35H67O11P/c1-3-5-7-8-9-10-11-14-17-21-31(37)24-35(40)46-33(28-45-47(41,42)44-26-32(38)25-36)27-43-34(39)22-18-15-12-13-16-20-30-23-29(30)19-6-4-2/h29-33,36-38H,3-28H2,1-2H3,(H,41,42)/t29?,30?,31?,32-,33+/m0/s1 XQTQEVJEAVMUMB-QOGUGHGESA-N Solid Membrane logp 5.64 ALOGPS logs -6.10 ALOGPS solubility 5.54e-04 g/l ALOGPS logp 7.59 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxytetradecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid ChemAxon average_mass 694.884 ChemAxon mono_mass 694.442099975 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CC(O)CCCCCCCCCCC ChemAxon formula C35H67O11P ChemAxon inchi InChI=1S/C35H67O11P/c1-3-5-7-8-9-10-11-14-17-21-31(37)24-35(40)46-33(28-45-47(41,42)44-26-32(38)25-36)27-43-34(39)22-18-15-12-13-16-20-30-23-29(30)19-6-4-2/h29-33,36-38H,3-28H2,1-2H3,(H,41,42)/t29?,30?,31?,32-,33+/m0/s1 ChemAxon inchikey XQTQEVJEAVMUMB-QOGUGHGESA-N ChemAxon polar_surface_area 169.05 ChemAxon refractivity 181.11 ChemAxon polarizability 80.15 ChemAxon rotatable_bond_count 35 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis (CL(17:0cycw7c/17:0cycw7c/14:0/15:0cyclo)) Phospholipids are membrane components in E. coli. The major phospholipids of E. coli are phosphatidylethanolamine, phosphatidylglycerol and cardiolipin. All phospholipids contain sn-glycerol-3-phosphate esterified with fatty acids at the sn-1 and sn-2 positions. The reaction starts from a glycerone phosphate (dihydroxyacetone phosphate) produced in glycolysis. The glycerone phosphate is transformed to a sn-glycerol 3-phosphate (glycerol 3 phosphate) by NADPH driven glycerol-3-phosphate dehydrogenase. Sn-glycerol 3-phosphate is transformed to a 1-acyl-sn-glycerol 3-phosphate(1-oleyl-2-lyso-phosphatidate , 1-palmitoylglycerol 3-phosphate , 1-stearoyl-sn-glycerol 3-phosphate). This can be achieve by a sn-glycerol-3-phosphate 1-0-acyltransferase that interacts either with a long-chain acyl-CoA or with an acyl-[acp]. The 1-acyl-sn-glycerol 3-phosphate is transformed into a 1,2-diacyl-sn-glycerol 3-phosphate through a 1-acylglycerol-3-phosphate O-acyltransferase. This compound is then converted into a CPD-diacylglycerol through a CTP (phosphatidate cytididyltransferase. CPD-diacylglycerol can be transformed either to a L-1-phosphatidylserine or a L-1-phosphatidylglycerol-phosphate through a phosphatidylserine synthase or a phosphatidylglycerophosphate synthase respectively. The L-1-phosphatidylserine transforms into L-1-phosphatidylethanolamine through a phosphatidylserine decarboxylase, o the other hand L-1-phosphatidylglycerol-phosphate gets transformed into a L-1-phosphatidyl-glycerol through a phosphatidylglycerophosphatase. These 2 products combines produce a cardiolipin and a ethanolamine. The L-1 phosphatidyl-glycerol can also interact with cardiolipin synthase resulting in a glycerol and a cardiolipin. PW001702 Metabolic phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/14:0/15:0cyclo)) Phospholipids are membrane components in E. coli. The major phospholipids of E. coli are phosphatidylethanolamine, phosphatidylglycerol and cardiolipin. All phospholipids contain sn-glycerol-3-phosphate esterified with fatty acids at the sn-1 and sn-2 positions. The reaction starts from a glycerone phosphate (dihydroxyacetone phosphate) produced in glycolysis. The glycerone phosphate is transformed to a sn-glycerol 3-phosphate (glycerol 3 phosphate) by NADPH driven glycerol-3-phosphate dehydrogenase. Sn-glycerol 3-phosphate is transformed to a 1-acyl-sn-glycerol 3-phosphate(1-oleyl-2-lyso-phosphatidate , 1-palmitoylglycerol 3-phosphate , 1-stearoyl-sn-glycerol 3-phosphate). This can be achieve by a sn-glycerol-3-phosphate 1-0-acyltransferase that interacts either with a long-chain acyl-CoA or with an acyl-[acp]. The 1-acyl-sn-glycerol 3-phosphate is transformed into a 1,2-diacyl-sn-glycerol 3-phosphate through a 1-acylglycerol-3-phosphate O-acyltransferase. This compound is then converted into a CPD-diacylglycerol through a CTP (phosphatidate cytididyltransferase. CPD-diacylglycerol can be transformed either to a L-1-phosphatidylserine or a L-1-phosphatidylglycerol-phosphate through a phosphatidylserine synthase or a phosphatidylglycerophosphate synthase respectively. The L-1-phosphatidylserine transforms into L-1-phosphatidylethanolamine through a phosphatidylserine decarboxylase, o the other hand L-1-phosphatidylglycerol-phosphate gets transformed into a L-1-phosphatidyl-glycerol through a phosphatidylglycerophosphatase. These 2 products combines produce a cardiolipin and a ethanolamine. The L-1 phosphatidyl-glycerol can also interact with cardiolipin synthase resulting in a glycerol and a cardiolipin. PW001276 Metabolic Specdb::CMs 1085874 Specdb::MsMs 1257787 Specdb::MsMs 1257788 Specdb::MsMs 1257789 Specdb::MsMs 1372945 Specdb::MsMs 1372946 Specdb::MsMs 1372947 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 Yuan Y, Leeds JA, Meredith TC (2012). "Pseudomonas aeruginosa Directly Shunts β-Oxidation Degradation Intermediates into De Novo Fatty Acid Biosynthesis." J Bacteriol. 194(19):5185-96 22753057 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Lysophospholipase L2 P07000 PLDB_ECOLI pldB http://ecmdb.ca/proteins/P07000.xml Phosphatidylglycerophosphatase B P0A924 PGPB_ECOLI pgpB http://ecmdb.ca/proteins/P0A924.xml Phosphatidylglycerophosphatase A P18200 PGPA_ECOLI pgpA http://ecmdb.ca/proteins/P18200.xml Lipid A export ATP-binding/permease protein msbA P60752 MSBA_ECOLI msbA http://ecmdb.ca/proteins/P60752.xml Protein crcA P37001 CRCA_ECOLI crcA http://ecmdb.ca/proteins/P37001.xml Cardiolipin synthase P0A6H8 CLS_ECOLI cls http://ecmdb.ca/proteins/P0A6H8.xml Putative cardiolipin synthase ybhO P0AA84 YBHO_ECOLI ybhO http://ecmdb.ca/proteins/P0AA84.xml Cardiolipin synthase C P75919 CLSC_ECOLI clsC http://ecmdb.ca/proteins/P75919.xml Probable phospholipid ABC transporter-binding protein mlaB P64602 MLAB_ECOLI mlaB http://ecmdb.ca/proteins/P64602.xml Lipid A export ATP-binding/permease protein msbA P60752 MSBA_ECOLI msbA http://ecmdb.ca/proteins/P60752.xml Probable phospholipid ABC transporter-binding protein mlaD P64604 MLAD_ECOLI mlaD http://ecmdb.ca/proteins/P64604.xml Probable phospholipid ABC transporter permease protein mlaE P64606 MLAE_ECOLI mlaE http://ecmdb.ca/proteins/P64606.xml PG(14:0(3-OH)/15:0cyclo) + PE(19:iso/15:0cyclo) > Ethanolamine + CL(19:0cycv8c/15:0cyclo/14:0/15:0cyclo) PW_R005050 PG(14:0(3-OH)/15:0cyclo) + PE(17:0cycw7c/17:0cycw7c) > Ethanolamine + CL(17:0cycw7c/17:0cycw7c/14:0/15:0cyclo) PW_R005069 2 PGP(14:0(3-OH)/15:0cyclo) + Water >2 Phosphate + PG(14:0(3-OH)/15:0cyclo) PW_R005726 2 PGP(14:0(3-OH)/15:0cyclo) + Water >2 PG(14:0(3-OH)/15:0cyclo) + Phosphate PW_R005728