2.0 2012-08-23 12:31:00 -0600 2015-12-09 09:37:15 -0700 ECMDB22067 M2MDB002457 CL(16:0/16:0/14:0/18:1(9Z)) CL(16:0/16:0/14:0/18:1(9Z)) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(16:0/16:0/14:0/18:1(9Z)) contains two chains of hexadecanoic acid at the C1 and C2 positions, one chain of tetradecanoic acid at the C3 position, one chain of (9Z-octadecenoyl) 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'-[1,2-dihexadecanoyl-rac-glycero-3-phospho],3'-[1,2-ditetradecanoyl-rac-glycero-3-phospho]-glycerol 1'-[1,2-dipalmitoyl-rac-glycero-3-phospho],3'-[1,2-dimyristoyl-rac-glycero-3-phospho]-glycerol Cardiolipin(16:0/16:0/14:0/14:0) Cardiolipin(60:0) CL(1'-[16:0/16:0],3'-[14:0/14:0]) CL(16:0/16:0/14:0/14:0) CL(60:0) C73H140O17P2 1351.854 1350.956577044 [(2S)-3-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy]phosphinic acid (2S)-3-{[(2R)-2,3-bis(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy)phosphinic acid [H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C73H140O17P2/c1-5-9-13-17-21-25-29-32-33-36-40-44-48-52-56-60-73(78)90-68(63-83-70(75)57-53-49-45-41-37-28-24-20-16-12-8-4)65-87-91(79,80)85-61-67(74)62-86-92(81,82)88-66-69(89-72(77)59-55-51-47-43-39-35-31-27-23-19-15-11-7-3)64-84-71(76)58-54-50-46-42-38-34-30-26-22-18-14-10-6-2/h32-33,67-69,74H,5-31,34-66H2,1-4H3,(H,79,80)(H,81,82)/b33-32-/t67-,68-,69-/m1/s1 MIIOTHCXFOKORP-DYEQFORBSA-N Solid Membrane logp 8.88 ALOGPS logs -7.23 ALOGPS solubility 7.99e-05 g/l ALOGPS logp 23.35 ChemAxon pka_strongest_acidic 1.59 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2S)-3-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy]phosphinic acid ChemAxon average_mass 1351.854 ChemAxon mono_mass 1350.956577044 ChemAxon smiles [H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC ChemAxon formula C73H140O17P2 ChemAxon inchi InChI=1S/C73H140O17P2/c1-5-9-13-17-21-25-29-32-33-36-40-44-48-52-56-60-73(78)90-68(63-83-70(75)57-53-49-45-41-37-28-24-20-16-12-8-4)65-87-91(79,80)85-61-67(74)62-86-92(81,82)88-66-69(89-72(77)59-55-51-47-43-39-35-31-27-23-19-15-11-7-3)64-84-71(76)58-54-50-46-42-38-34-30-26-22-18-14-10-6-2/h32-33,67-69,74H,5-31,34-66H2,1-4H3,(H,79,80)(H,81,82)/b33-32-/t67-,68-,69-/m1/s1 ChemAxon inchikey MIIOTHCXFOKORP-DYEQFORBSA-N ChemAxon polar_surface_area 236.95 ChemAxon refractivity 371.22 ChemAxon polarizability 162.32 ChemAxon rotatable_bond_count 77 ChemAxon acceptor_count 9 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis CL(16:0/16:0/14:0/18:1(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." PW001255 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::MsMs 1233268 Specdb::MsMs 1233269 Specdb::MsMs 1233270 Specdb::MsMs 1348780 Specdb::MsMs 1348781 Specdb::MsMs 1348782 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(16:0/16:0) + PE(14:0/18:1(9Z)) > Ethanolamine + CL(16:0/16:0/14:0/18:1(9Z)) PW_R004149 Luria-Bertani (LB) media Shake flask 0.03696 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