1.0 2016-10-03 18:02:27 UTC 2020-05-11 19:10:06 UTC BMDB0010253 BMDB10253 CL(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) CL(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)), also known as Cl(18:2(9z,12z)/20:4(8z,11z,14z,17z)/20:4(8z,11z,14z,17z)/20:4(8z,11z,14z,17z)) or Cl(18:2(9z,12z)/20:4(8z,11z,14z,17z)/20:4(8z,11z,14z,17z)/20:4(8z,11z,14z,17z)), belongs to the class of organic compounds known as cardiolipins. These are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,2-diacylglycerol chain. Their general formula is OC(COP(O)(=O)OC[C@@H](CO[R1])O[R2])COP(O)(=O)OC[C@@H](CO[R3])O[R4], where R1-R4 are four fatty acyl chains. CL(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). CL(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) and cytidine monophosphate can be biosynthesized from PG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)) and CDP-DG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)); which is mediated by the enzyme cardiolipin synthase. In cattle, CL(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) pathway. 1'-[1-Linoleoyl-2-eicsoate 1'-[1-Linoleoyl-2-eicsoatetraenoyl-sn-glycero-3-phospho],3'-[1,2-dieicsoate 1'-[1-Linoleoyl-2-eicsoatetraenoyl-sn-glycero-3-phospho],3'-[1,2-dieicsoatetraenoyl-rac-glycero-3-phospho]-glycerol 1'-[1-Linoleoyl-2-eicsoatetraenoyl-sn-glycero-3-phospho],3'-[1,2-dieicsoic acid 1'-[1-Linoleoyl-2-eicsoic acid Cardiolipin(18:2/20:4/20:4/20:4) Cardiolipin(18:2N6/20:4N3/20:4N3/20:4N3) Cardiolipin(18:2W6/20:4W3/20:4W3/20:4W3) Cardiolipin(78:14) Cardiolipins(18:2/20:4/20:4/20:4) Cardiolipins(18:2N6/20:4N3/20:4N3/20:4N3) Cardiolipins(18:2W6/20:4W3/20:4W3/20:4W3) Cardiolipins(78:14) CL(1'-[18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)],3'-[20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)]) CL(18:2/20:4/20:4/20:4) CL(18:2N6/20:4N3/20:4N3/20:4N3) CL(18:2W6/20:4W3/20:4W3/20:4W3) CL(78:14) 1'-[1-(9Z,12Z-Octadecadienoyl)-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phospho],3'-[1,2-di(8Z,11Z,14Z,17Z-eicosapentaenoyl)-rac-glycero-3-phospho]-glycerol CL(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) C87H142O17P2 1521.9957 1520.972226142 [(2R)-2,3-bis[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxy][2-hydroxy-3-({hydroxy[(2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphinic acid (2R)-2,3-bis[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxy(2-hydroxy-3-{[hydroxy(2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphoryl]oxy}propoxy)phosphinic acid [H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C87H142O17P2/c1-5-9-13-17-21-25-29-33-37-40-44-48-52-56-60-64-68-72-85(90)98-78-83(104-87(92)74-70-66-62-58-54-50-46-42-39-35-31-27-23-19-15-11-7-3)80-102-106(95,96)100-76-81(88)75-99-105(93,94)101-79-82(77-97-84(89)71-67-63-59-55-51-47-43-36-32-28-24-20-16-12-8-4)103-86(91)73-69-65-61-57-53-49-45-41-38-34-30-26-22-18-14-10-6-2/h9-11,13-15,21-28,33-39,43-46,48-50,81-83,88H,5-8,12,16-20,29-32,40-42,47,51-80H2,1-4H3,(H,93,94)(H,95,96)/b13-9-,14-10-,15-11-,25-21-,26-22-,27-23-,28-24-,37-33-,38-34-,39-35-,43-36-,48-44-,49-45-,50-46-/t81-,82+,83+/m0/s1 OWQJOQOHTKOXGF-CHQWNPPXSA-N belongs to the class of organic compounds known as cardiolipins. These are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,2-diacylglycerol chain. Their general formula is OC(COP(O)(=O)OC[C@@H](CO[R1])O[R2])COP(O)(=O)OC[C@@H](CO[R3])O[R4], where R1-R4 are four fatty acyl chains. Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphoglycerophosphoglycerols Cardiolipins Solid logp 8.83 ALOGPS logs -7.20 ALOGPS logp 24.87 ChemAxon pka_strongest_acidic 1.59 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R)-2,3-bis[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxy][2-hydroxy-3-({hydroxy[(2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphinic acid ChemAxon average_mass 1521.9957 ChemAxon mono_mass 1520.972226142 ChemAxon smiles [H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC ChemAxon formula C87H142O17P2 ChemAxon inchi InChI=1S/C87H142O17P2/c1-5-9-13-17-21-25-29-33-37-40-44-48-52-56-60-64-68-72-85(90)98-78-83(104-87(92)74-70-66-62-58-54-50-46-42-39-35-31-27-23-19-15-11-7-3)80-102-106(95,96)100-76-81(88)75-99-105(93,94)101-79-82(77-97-84(89)71-67-63-59-55-51-47-43-36-32-28-24-20-16-12-8-4)103-86(91)73-69-65-61-57-53-49-45-41-38-34-30-26-22-18-14-10-6-2/h9-11,13-15,21-28,33-39,43-46,48-50,81-83,88H,5-8,12,16-20,29-32,40-42,47,51-80H2,1-4H3,(H,93,94)(H,95,96)/b13-9-,14-10-,15-11-,25-21-,26-22-,27-23-,28-24-,37-33-,38-34-,39-35-,43-36-,48-44-,49-45-,50-46-/t81-,82+,83+/m0/s1 ChemAxon inchikey OWQJOQOHTKOXGF-CHQWNPPXSA-N ChemAxon polar_surface_area 236.95 ChemAxon refractivity 450.15 ChemAxon polarizability 175.62 ChemAxon rotatable_bond_count 78 ChemAxon acceptor_count 9 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) SMP0079675 Specdb::MsMs 848044 Specdb::MsMs 848045 Specdb::MsMs 848046 Specdb::MsMs 907156 Specdb::MsMs 907157 Specdb::MsMs 907158 All Tissues Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 53480387 FDB027405