1.0 2016-10-03 18:04:07 UTC 2020-05-11 19:10:54 UTC BMDB0010311 BMDB10311 CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z)), also known as Cl(22:6(4z,7z,10z,13z,16z,19z)/20:4(8z,11z,14z,17z)/18:3(9z,12z,15z)/18:2(9z,12z)) or Cl(22:6(4z,7z,10z,13z,16z,19z)/20:4(8z,11z,14z,17z)/18:3(9z,12z,15z)/18:2(9z,12z)), 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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) and cytidine monophosphate can be biosynthesized from PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)) and CDP-DG(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)); which is mediated by the enzyme cardiolipin synthase. In cattle, CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) pathway. 1'-[1-Docosahexaenoyl-2-eicsoate 1'-[1-Docosahexaenoyl-2-eicsoatetraenoyl-sn-glycero-3-phospho],3'-[1,2-dia-linolenoyl-rac-glycero-3-phospho]-glycerol 1'-[1-Docosahexaenoyl-2-eicsoic acid Cardiolipin(22:6/20:4/18:3/18:3) Cardiolipin(22:6N3/20:4N3/18:3N3/18:3N3) Cardiolipin(22:6W3/20:4W3/18:3W3/18:3W3) Cardiolipin(78:16) Cardiolipins(22:6/20:4/18:3/18:3) Cardiolipins(22:6N3/20:4N3/18:3N3/18:3N3) Cardiolipins(22:6W3/20:4W3/18:3W3/18:3W3) Cardiolipins(78:16) CL(1'-[22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)],3'-[18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)]) CL(22:6/20:4/18:3/18:3) CL(22:6N3/20:4N3/18:3N3/18:3N3) CL(22:6W3/20:4W3/18:3W3/18:3W3) CL(78:16) 1'-[1-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phospho],3'-[1,2-di(9Z,12Z,15Z-octadeatrienoyl)-rac-glycero-3-phospho]-glycerol CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) C87H140O17P2 1519.9798 1518.956576078 [(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxy][2-hydroxy-3-({hydroxy[(2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphinic acid (2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxy(2-hydroxy-3-{[hydroxy(2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-[(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/C\C=C/CC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CC\C=C/C\C=C/C\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/C87H140O17P2/c1-5-9-13-17-21-25-29-33-37-39-40-42-45-48-52-56-60-64-68-72-85(90)98-78-83(104-87(92)74-70-66-62-58-54-50-46-41-38-34-30-26-22-18-14-10-6-2)80-102-106(95,96)100-76-81(88)75-99-105(93,94)101-79-82(103-86(91)73-69-65-61-57-53-49-44-36-32-28-24-20-16-12-8-4)77-97-84(89)71-67-63-59-55-51-47-43-35-31-27-23-19-15-11-7-3/h9-11,13-15,21-28,33-38,40,42-44,46,48,50,52,60,64,81-83,88H,5-8,12,16-20,29-32,39,41,45,47,49,51,53-59,61-63,65-80H2,1-4H3,(H,93,94)(H,95,96)/b13-9-,14-10-,15-11-,25-21-,26-22-,27-23-,28-24-,37-33-,38-34-,42-40-,43-35-,44-36-,50-46-,52-48-,64-60-/t81-,82-,83-/m1/s1 LOZMAZMZCODBRM-PUFACCRPSA-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 8.78 ALOGPS logs -7.16 ALOGPS logp 24.51 ChemAxon pka_strongest_acidic 1.59 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxy][2-hydroxy-3-({hydroxy[(2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphinic acid ChemAxon average_mass 1519.9798 ChemAxon mono_mass 1518.956576078 ChemAxon smiles [H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CC\C=C/C\C=C/C\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 C87H140O17P2 ChemAxon inchi InChI=1S/C87H140O17P2/c1-5-9-13-17-21-25-29-33-37-39-40-42-45-48-52-56-60-64-68-72-85(90)98-78-83(104-87(92)74-70-66-62-58-54-50-46-41-38-34-30-26-22-18-14-10-6-2)80-102-106(95,96)100-76-81(88)75-99-105(93,94)101-79-82(103-86(91)73-69-65-61-57-53-49-44-36-32-28-24-20-16-12-8-4)77-97-84(89)71-67-63-59-55-51-47-43-35-31-27-23-19-15-11-7-3/h9-11,13-15,21-28,33-38,40,42-44,46,48,50,52,60,64,81-83,88H,5-8,12,16-20,29-32,39,41,45,47,49,51,53-59,61-63,65-80H2,1-4H3,(H,93,94)(H,95,96)/b13-9-,14-10-,15-11-,25-21-,26-22-,27-23-,28-24-,37-33-,38-34-,42-40-,43-35-,44-36-,50-46-,52-48-,64-60-/t81-,82-,83-/m1/s1 ChemAxon inchikey LOZMAZMZCODBRM-PUFACCRPSA-N ChemAxon polar_surface_area 236.95 ChemAxon refractivity 451.26 ChemAxon polarizability 173.59 ChemAxon rotatable_bond_count 77 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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) SMP0080422 Specdb::MsMs 815653 Specdb::MsMs 815654 Specdb::MsMs 815655 Specdb::MsMs 893380 Specdb::MsMs 893381 Specdb::MsMs 893382 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 FDB027463 53480445