2.0 2012-10-24 09:54:59 -0600 2015-12-09 12:06:51 -0700 ECMDB23678 M2MDB004068 PG(14:0(3-OH)/18:1(9Z)) PG(14:0(3-OH)/18:1(9Z)) 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)/18:1(9Z)), in particular, consists of one 3-hydroxytetradecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-glycerol) 1-3-hydroxytetradecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoglycerol 1-3-hydroxytetradecanoyl-2-oleoyl-sn-glycero-3-phosphoglycerol GPG(14:0/18:1) GPG(32:1) PG(14:0/18:1) PG(32:1) Phosphatidylglycerol(14:0/18:1) Phosphatidylglycerol(32:1) C38H73O11P 736.965 736.489050169 [(2S)-2,3-dihydroxypropoxy][(2R)-2-[(3-hydroxytetradecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid (2S)-2,3-dihydroxypropoxy((2R)-2-[(3-hydroxytetradecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CC(O)CCCCCCCCCCC InChI=1S/C38H73O11P/c1-3-5-7-9-11-13-14-15-16-17-18-20-22-24-26-28-37(42)46-32-36(33-48-50(44,45)47-31-35(41)30-39)49-38(43)29-34(40)27-25-23-21-19-12-10-8-6-4-2/h15-16,34-36,39-41H,3-14,17-33H2,1-2H3,(H,44,45)/b16-15-/t34?,35-,36+/m0/s1 YZWXTZVNFIEAJY-TXMSSCOLSA-N Solid Membrane logp 6.75 ALOGPS logs -6.45 ALOGPS solubility 2.63e-04 g/l ALOGPS logp 9.34 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2S)-2,3-dihydroxypropoxy][(2R)-2-[(3-hydroxytetradecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid ChemAxon average_mass 736.965 ChemAxon mono_mass 736.489050169 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CC(O)CCCCCCCCCCC ChemAxon formula C38H73O11P ChemAxon inchi InChI=1S/C38H73O11P/c1-3-5-7-9-11-13-14-15-16-17-18-20-22-24-26-28-37(42)46-32-36(33-48-50(44,45)47-31-35(41)30-39)49-38(43)29-34(40)27-25-23-21-19-12-10-8-6-4-2/h15-16,34-36,39-41H,3-14,17-33H2,1-2H3,(H,44,45)/b16-15-/t34?,35-,36+/m0/s1 ChemAxon inchikey YZWXTZVNFIEAJY-TXMSSCOLSA-N ChemAxon polar_surface_area 169.05 ChemAxon refractivity 197.94 ChemAxon polarizability 87.27 ChemAxon rotatable_bond_count 39 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/14:0/18:1(9Z))) 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. PW001706 Metabolic phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/14:0/18:1(9Z))) 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. PW001514 Metabolic Specdb::CMs 1083717 Specdb::NmrOneD 259588 Specdb::NmrOneD 259589 Specdb::NmrOneD 259590 Specdb::NmrOneD 259591 Specdb::NmrOneD 259592 Specdb::NmrOneD 259593 Specdb::NmrOneD 259594 Specdb::NmrOneD 259595 Specdb::NmrOneD 259596 Specdb::NmrOneD 259597 Specdb::NmrOneD 259598 Specdb::NmrOneD 259599 Specdb::NmrOneD 259600 Specdb::NmrOneD 259601 Specdb::NmrOneD 259602 Specdb::NmrOneD 259603 Specdb::NmrOneD 259604 Specdb::NmrOneD 259605 Specdb::NmrOneD 259606 Specdb::NmrOneD 259607 Specdb::MsMs 1249315 Specdb::MsMs 1249316 Specdb::MsMs 1249317 Specdb::MsMs 1364617 Specdb::MsMs 1364618 Specdb::MsMs 1364619 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 PE(15:0/18:1(9Z)) + PG(14:0(3-OH)/18:1(9Z)) + PE(18:1(9Z)/15:0cyclo) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/14:0/18:1(9Z)) PW_R004844 PG(14:0(3-OH)/18:1(9Z)) + PE(17:0cycw7c/17:0cycw7c) > Ethanolamine + CL(17:0cycw7c/17:0cycw7c/14:0/18:1(9Z)) PW_R005075 2 PGP(14:0(3-OH)/18:1(9Z)) + Water >2 PG(14:0(3-OH)/18:1(9Z)) + Phosphate PW_R005732