2.0 2012-05-31 14:56:57 -0600 2015-12-09 12:07:26 -0700 ECMDB21063 M2MDB001479 PG(16:0/14:0) PG(16:0/14:0) 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(16:0/14:0), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one tetradecanoyl 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-hexadecanoyl-2-tetradecanoyl-glycero-3-phospho-(1'-sn-glycerol) 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phospho-(1'-glycerol) 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphoglycerol 1-palmitoyl-2-myristoyl-sn-glycero-3-phosphoglycerol GPG(16:0/14:0) GPG(30:0) PG(30:0) Phosphatidylglycerol(16:0/14:0) Phosphatidylglycerol(30:0) C36H71O10P 694.9167 694.478485004 [(2S)-2,3-dihydroxypropoxy][(2R)-2-(hexadecanoyloxy)-3-(tetradecanoyloxy)propoxy]phosphinic acid (2S)-2,3-dihydroxypropoxy((2R)-2-(hexadecanoyloxy)-3-(tetradecanoyloxy)propoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C36H71O10P/c1-3-5-7-9-11-13-15-16-18-20-22-24-26-28-36(40)46-34(32-45-47(41,42)44-30-33(38)29-37)31-43-35(39)27-25-23-21-19-17-14-12-10-8-6-4-2/h33-34,37-38H,3-32H2,1-2H3,(H,41,42)/t33-,34+/m0/s1 ZAXBYLHGBBMAAY-SZAHLOSFSA-N Inner membrane Membrane Outer membrane logp 7.33 ALOGPS logs -6.60 ALOGPS solubility 1.74e-04 g/l ALOGPS logp 10.05 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2S)-2,3-dihydroxypropoxy][(2R)-2-(hexadecanoyloxy)-3-(tetradecanoyloxy)propoxy]phosphinic acid ChemAxon average_mass 694.9167 ChemAxon mono_mass 694.478485004 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC ChemAxon formula C36H71O10P ChemAxon inchi InChI=1S/C36H71O10P/c1-3-5-7-9-11-13-15-16-18-20-22-24-26-28-36(40)46-34(32-45-47(41,42)44-30-33(38)29-37)31-43-35(39)27-25-23-21-19-17-14-12-10-8-6-4-2/h33-34,37-38H,3-32H2,1-2H3,(H,41,42)/t33-,34+/m0/s1 ChemAxon inchikey ZAXBYLHGBBMAAY-SZAHLOSFSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 186.11 ChemAxon polarizability 83.3 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis CL(16:0/17:0cycw7c/14:0/17:0cycw7c) "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." PW001339 Metabolic phospholipid biosynthesis (CL(18:1(9Z)/16:0/16:0/14:0)) 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. PW002011 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::CMs 1085175 Specdb::NmrOneD 315381 Specdb::NmrOneD 315382 Specdb::NmrOneD 315383 Specdb::NmrOneD 315384 Specdb::NmrOneD 315385 Specdb::NmrOneD 315386 Specdb::NmrOneD 315387 Specdb::NmrOneD 315388 Specdb::NmrOneD 315389 Specdb::NmrOneD 315390 Specdb::NmrOneD 315391 Specdb::NmrOneD 315392 Specdb::NmrOneD 315393 Specdb::NmrOneD 315394 Specdb::NmrOneD 315395 Specdb::NmrOneD 315396 Specdb::NmrOneD 315397 Specdb::NmrOneD 315398 Specdb::NmrOneD 315399 Specdb::NmrOneD 315400 Specdb::MsMs 25793 Specdb::MsMs 25794 Specdb::MsMs 25795 Specdb::MsMs 32351 Specdb::MsMs 32352 Specdb::MsMs 32353 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 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 Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. 22102590 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 Phosphatidylglycerophosphatase B P0A924 PGPB_ECOLI pgpB http://ecmdb.ca/proteins/P0A924.xml Phosphatidylglycerophosphatase A P18200 PGPA_ECOLI pgpA http://ecmdb.ca/proteins/P18200.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 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 PGP(16:0/16:0) + Water + PGP(16:0/14:0) > PG(16:0/14:0) + Phosphate PW_R004109 PE(17:0cycw7c/17:0cycw7c) + PG(16:0/14:0) > Ethanolamine + CL(16:0/17:0cycw7c/14:0/17:0cycw7c) PW_R004249 PE(17:0/14:0) + PG(16:0/14:0) > Ethanolamine + CL(19:0cycv8c/18:1(9Z)/14:0/14:0) PW_R004326 PE(17:0/14:0) + PG(16:0/14:0) > Ethanolamine + CL(17:0cycw7c/17:0cycw7c/14:0/17:0cycw7c) PW_R004631 PE(17:0/14:0) + PG(16:0/14:0) > Ethanolamine + CL(17:0cycw7c/17:0cycw7c/17:0cycw7c/14:0) PW_R004634 2 PG(16:0/14:0) > Glycerol + CL(19:0cycv8c/14:0/14:0/19:0cycv8c) PW_R004180 2 PG(16:0/14:0) > CL(19:0cycv8c/14:0/19:0cycv8c/14:0) + Glycerol PW_R004183 2 PG(16:0/14:0) > Glycerol + CL(19:0cycv8c/15:0cyclo/15:0cyclo/17:0cycw7c) PW_R004198 2 PG(16:0/14:0) > Glycerol + CL(19:0cycv8c/15:0cyclo/17:0cycw7c/15:0cyclo) PW_R004205 2 PG(16:0/14:0) > Glycerol + CL(19:0cycv8c/19:0cycv8c/14:0/14:0) PW_R004343 2 PG(16:0/14:0) > Glycerol + CL(17:0cycw7c/18:1(9Z)/17:0cycw7c/14:0) PW_R004378 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/14:0/17:0cycw7c/17:0cycw7c) PW_R004416 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo) PW_R004448 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/16:0/14:0/18:1(9Z)) PW_R004504 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/16:0/18:1(9Z)/14:0) PW_R004509 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/16:1(9Z)/14:0/18:1(9Z)) PW_R004530 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/14:0) PW_R004543 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/17:0cycw7c/14:0/17:0cycw7c) PW_R004558 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/17:0cycw7c/17:0cycw7c/14:0) PW_R004561 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/18:1(9Z)/14:0/16:0) PW_R004587 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/18:1(9Z)/14:0/16:1(9Z)) PW_R004588 2 PG(16:0/14:0) > Glycerol + CL(17:0cycw7c/16:1(9Z)/17:0cycw7c/16:1(9Z)) PW_R004621 2 PG(16:0/14:0) > Glycerol + CL(17:0cycw7c/18:1(9Z)/14:0/17:0cycw7c) PW_R004637 PG(16:0/14:0) + PE(18:1(9Z)/16:0) > Ethanolamine + CL(18:1(9Z)/16:0/16:0/14:0) PW_R005668