1.0 2016-10-03 18:02:25 UTC 2020-05-11 19:10:05 UTC BMDB0010252 BMDB10252 CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)), also known as Cl(18:2(9z,12z)/20:4(5z,8z,11z,14z)/20:4(5z,8z,11z,14z)/20:4(5z,8z,11z,14z)) or Cl(18:2(9z,12z)/20:4(5z,8z,11z,14z)/20:4(5z,8z,11z,14z)/20:4(5z,8z,11z,14z)), 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. Thus, CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) is considered to be a glycerophosphoglycerophosphoglycerol lipid molecule. CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) and cytidine monophosphate can be biosynthesized from PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) and CDP-DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)); which is mediated by the enzyme cardiolipin synthase. In cattle, CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) pathway. 1'-[1-Linoleoyl-2-arachidonoyl-sn-glycero-3-phospho],3'-[1,2-diarachidonoyl-rac-glycero-3-phospho]-glycerol Cardiolipin(18:2/20:4/20:4/20:4) Cardiolipin(78:14) CL(1'-[18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)],3'-[20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)]) CL(18:2/20:4/20:4/20:4) CL(78:14) 1'-[1-(9Z,12Z-Octadecadienoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho],3'-[1,2-di(5Z,8Z,11Z,14Z-eicosatetraenoyl)-rac-glycero-3-phospho]-glycerol CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) C87H142O17P2 1521.9957 1520.972226142 [(2R)-2,3-bis[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy][2-hydroxy-3-({hydroxy[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphinic acid (2R)-2,3-bis[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy(2-hydroxy-3-{[hydroxy(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-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)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC 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/h21-28,33-39,43-46,48-50,56-58,60-62,81-83,88H,5-20,29-32,40-42,47,51-55,59,63-80H2,1-4H3,(H,93,94)(H,95,96)/b25-21-,26-22-,27-23-,28-24-,37-33-,38-34-,39-35-,43-36-,48-44-,49-45-,50-46-,60-56-,61-57-,62-58-/t81-,82+,83+/m0/s1 MEFSWTNMBRIQIW-BQNLJZDPSA-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 Carbonyl compounds Carboxylic acid esters Dialkyl phosphates Fatty acid esters Hydrocarbon derivatives Organic oxides Secondary alcohols Tetracarboxylic acids and derivatives Alcohol Aliphatic acyclic compound Alkyl phosphate Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cardiolipin Dialkyl phosphate Fatty acid ester Fatty acyl Hydrocarbon derivative Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organooxygen compound Phosphoric acid ester Secondary alcohol Tetracarboxylic acid or derivatives Aliphatic acyclic compounds Solid logp 8.95 ALOGPS logs -7.22 ALOGPS logp 24.87 ChemAxon pka_strongest_acidic 1.59 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R)-2,3-bis[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy][2-hydroxy-3-({hydroxy[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-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)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC 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/h21-28,33-39,43-46,48-50,56-58,60-62,81-83,88H,5-20,29-32,40-42,47,51-55,59,63-80H2,1-4H3,(H,93,94)(H,95,96)/b25-21-,26-22-,27-23-,28-24-,37-33-,38-34-,39-35-,43-36-,48-44-,49-45-,50-46-,60-56-,61-57-,62-58-/t81-,82+,83+/m0/s1 ChemAxon inchikey MEFSWTNMBRIQIW-BQNLJZDPSA-N ChemAxon polar_surface_area 236.95 ChemAxon refractivity 450.15 ChemAxon polarizability 176.57 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(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) SMP0079660 Specdb::MsMs 793288 Specdb::MsMs 793289 Specdb::MsMs 793290 Specdb::MsMs 883978 Specdb::MsMs 883979 Specdb::MsMs 883980 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 53480386 FDB027404