2.0 2015-09-08 19:36:26 -0600 2015-12-09 17:21:16 -0700 ECMDB24511 M2MDB006628 PGP(18:1(9Z)/17:0cycw7c) PGP(18:1(9Z)/17:0cycw7c) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(18:1(9Z)/17:0cycw7c), in particular, consists of one 9Z-octadecenoyl chain to the C-1 atom, and one heptadec-9-10-cyclo-anoyl to the C-2 atom. In E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase. C41H78O13P2 841.01 840.491766568 [(2R)-3-({[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2R)-3-{[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(9Z)-octadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCCC1CC1CCCCCC InChI=1S/C41H78O13P2/c1-3-5-7-9-10-11-12-13-14-15-16-17-18-21-25-29-40(43)50-34-39(35-53-56(48,49)52-33-38(42)32-51-55(45,46)47)54-41(44)30-26-22-19-20-24-28-37-31-36(37)27-23-8-6-4-2/h13-14,36-39,42H,3-12,15-35H2,1-2H3,(H,48,49)(H2,45,46,47)/b14-13-/t36?,37?,38-,39-/m1/s1 FPHSANILJGHQEE-GVCJYHPFSA-N logp 7.08 ALOGPS logs -6.14 ALOGPS solubility 6.15e-04 g/l ALOGPS logp 11.01 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R)-3-({[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 841.01 ChemAxon mono_mass 840.491766568 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCCC1CC1CCCCCC ChemAxon formula C41H78O13P2 ChemAxon inchi InChI=1S/C41H78O13P2/c1-3-5-7-9-10-11-12-13-14-15-16-17-18-21-25-29-40(43)50-34-39(35-53-56(48,49)52-33-38(42)32-51-55(45,46)47)54-41(44)30-26-22-19-20-24-28-37-31-36(37)27-23-8-6-4-2/h13-14,36-39,42H,3-12,15-35H2,1-2H3,(H,48,49)(H2,45,46,47)/b14-13-/t36?,37?,38-,39-/m1/s1 ChemAxon inchikey FPHSANILJGHQEE-GVCJYHPFSA-N ChemAxon polar_surface_area 195.35 ChemAxon refractivity 219.19 ChemAxon polarizability 95.68 ChemAxon rotatable_bond_count 42 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/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." PW001370 Metabolic Specdb::NmrOneD 288795 Specdb::NmrOneD 288796 Specdb::NmrOneD 288797 Specdb::NmrOneD 288798 Specdb::NmrOneD 288799 Specdb::NmrOneD 288800 Specdb::NmrOneD 288801 Specdb::NmrOneD 288802 Specdb::NmrOneD 288803 Specdb::NmrOneD 288804 Specdb::NmrOneD 288805 Specdb::NmrOneD 288806 Specdb::NmrOneD 288807 Specdb::NmrOneD 288808 Specdb::NmrOneD 288809 Specdb::NmrOneD 288810 Specdb::NmrOneD 288811 Specdb::NmrOneD 288812 Specdb::NmrOneD 288813 Specdb::NmrOneD 288814 Specdb::MsMs 1294699 Specdb::MsMs 1294700 Specdb::MsMs 1294701 Specdb::MsMs 1409359 Specdb::MsMs 1409360 Specdb::MsMs 1409361 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 2 PGP(18:1(9Z)/17:0cycw7c) + Water >2 PG(18:1(9Z)/17:0cycw7c) + Phosphate PW_R005791