2.0 2012-08-23 12:32:00 -0600 2015-12-09 10:37:33 -0700 ECMDB22517 M2MDB002907 CL(18:1(9Z)/16:0/16:0/19:0cycv8c) CL(18:1(9Z)/16:0/16:0/19:0cycv8c) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(18:1(9Z)/16:0/16:0/19:0cycv8c) contains one chain of (9Z-octadecenoyl) at the C1 position, two chains of hexadecanoic acid at the C2 and C3 positions, one chain of (heptadec-11-12-cyclo-anoyl) at the C4 position. While the theoretical charge of cardiolipins is -2, under normal physiological conditions (pH near 7), the molecule may carry only one negative charge. In prokaryotes such as E. coli, the enzyme known as diphosphatidylglycerol synthase catalyses the transfer of the phosphatidyl moiety of one phosphatidylglycerol to the free 3'-hydroxyl group of another, with the elimination of one molecule of glycerol. In E. coli, which acylates its glycerophospholipids with acyl chains ranging in length from 12 to 19 carbons and possibly containing an unsaturation, or a cyclopropane group more than 100 possible CL molecular species are theoretically possible. E. coli membranes consist of ~5% cardiolipin (CL), 20-25% phosphatidylglycerol (PG), and 70-80% phosphatidylethanolamine (PE) as well as smaller amounts of phosphatidylserine (PS). CL is distributed between the two leaflets of the bilayers and is located preferentially at the poles and septa in E. coli and other rod-shaped bacteria. It is known that the polar positioning of the proline transporter ProP and the mechanosensitive ion channel MscS in E. coli is dependent on CL. It is believed that cell shape may influence the localization of CL and the localization of certain membrane proteins. 1'-[1-(9Z-octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phospho],3'-[1,2-dihexadecanoyl-rac-glycero-3-phospho]-glycerol 1'-[1-oleoyl-2-palmitoyl-sn-glycero-3-phospho],3'-[1,2-dipalmitoyl-rac-glycero-3-phospho]-glycerol Cardiolipin(18:1/16:0/16:0/16:0) Cardiolipin(66:1) CL(1'-[18:1(9Z)/16:0],3'-[16:0/16:0]) CL(18:1/16:0/16:0/16:0) CL(66:1) C78H148O17P2 1419.973 1419.019177302 [(2R)-3-(hexadecanoyloxy)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy][(2R)-3-({[(2R)-2-(hexadecanoyloxy)-3-[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid (2R)-3-(hexadecanoyloxy)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy((2R)-3-{[(2R)-2-(hexadecanoyloxy)-3-[(9Z)-octadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid [H][C@@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCC1CC1CCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C78H148O17P2/c1-5-9-13-17-20-23-26-29-30-33-35-38-43-48-54-60-76(81)88-66-73(94-77(82)61-55-49-44-39-36-32-28-25-22-19-15-11-7-3)68-92-96(84,85)90-64-72(79)65-91-97(86,87)93-69-74(67-89-75(80)59-53-47-42-37-34-31-27-24-21-18-14-10-6-2)95-78(83)62-56-50-45-40-41-46-52-58-71-63-70(71)57-51-16-12-8-4/h29-30,70-74,79H,5-28,31-69H2,1-4H3,(H,84,85)(H,86,87)/b30-29-/t70?,71?,72-,73+,74+/m0/s1 GKAPXIJDNZFYBJ-LPHXZXNFSA-N Solid Membrane logp 9.01 ALOGPS logs -7.44 ALOGPS solubility 5.21e-05 g/l ALOGPS logp 24.8 ChemAxon pka_strongest_acidic 1.59 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R)-3-(hexadecanoyloxy)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy][(2R)-3-({[(2R)-2-(hexadecanoyloxy)-3-[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid ChemAxon average_mass 1419.973 ChemAxon mono_mass 1419.019177302 ChemAxon smiles [H][C@@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCC1CC1CCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCCCCCCCCCC ChemAxon formula C78H148O17P2 ChemAxon inchi InChI=1S/C78H148O17P2/c1-5-9-13-17-20-23-26-29-30-33-35-38-43-48-54-60-76(81)88-66-73(94-77(82)61-55-49-44-39-36-32-28-25-22-19-15-11-7-3)68-92-96(84,85)90-64-72(79)65-91-97(86,87)93-69-74(67-89-75(80)59-53-47-42-37-34-31-27-24-21-18-14-10-6-2)95-78(83)62-56-50-45-40-41-46-52-58-71-63-70(71)57-51-16-12-8-4/h29-30,70-74,79H,5-28,31-69H2,1-4H3,(H,84,85)(H,86,87)/b30-29-/t70?,71?,72-,73+,74+/m0/s1 ChemAxon inchikey GKAPXIJDNZFYBJ-LPHXZXNFSA-N ChemAxon polar_surface_area 236.95 ChemAxon refractivity 392.32 ChemAxon polarizability 171.41 ChemAxon rotatable_bond_count 80 ChemAxon acceptor_count 9 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis (CL(18:1(9Z)/16:0/16:0/19:0cycv8c) 2) 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. PW001783 Metabolic phospholipid biosynthesis (CL(18:1(9Z)/16:0/16:0/19:0cycv8c)) 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. PW001583 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::MsMs 1302559 Specdb::MsMs 1302560 Specdb::MsMs 1302561 Specdb::MsMs 1417138 Specdb::MsMs 1417139 Specdb::MsMs 1417140 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 De Siervo, A. J. (1969). "Alterations in the phospholipid composition of Escherichia coli B during growth at different temperatures." J Bacteriol 100:1342-1349. 4902814 Garrett, T. A., O'Neill, A. C., Hopson, M. L. (2012). "Quantification of cardiolipin molecular species in Escherichia coli lipid extracts using liquid chromatography/electrospray ionization mass spectrometry." Rapid Commun Mass Spectrom 26:2267-2274. 22956318 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 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 PG(16:0/19:iso) + PE(18:1(9Z)/16:0) > CL(18:1(9Z)/16:0/16:0/19:0cycv8c) + Ethanolamine PW_R004769 PE(16:0/19:0cycw8c) + PG(16:1(9Z)/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/16:0/16:0/19:0cycv8c) PW_R005080 PG(18:1(9Z)/16:0) + PE(16:0/19:0cycw8c) > Ethanolamine + CL(18:1(9Z)/16:0/16:0/19:0cycv8c) PW_R005084 Luria-Bertani (LB) media Shake flask 0.04948 uM 0.0 37 oC K12 Stationary phase cultures (overnight culture) Garrett, T. A., O'Neill, A. C., Hopson, M. L. (2012). "Quantification of cardiolipin molecular species in Escherichia coli lipid extracts using liquid chromatography/electrospray ionization mass spectrometry." Rapid Commun Mass Spectrom 26:2267-2274. 22956318