1.0 2016-10-03 18:02:23 UTC 2020-05-11 19:10:04 UTC BMDB0010251 BMDB10251 CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), also known as Cl(18:2(9z,12z)/18:2(9z,12z)/20:4(8z,11z,14z,17z)/22:6(4z,7z,10z,13z,16z,19z)) or Cl(18:2(9z,12z)/18:2(9z,12z)/20:4(8z,11z,14z,17z)/22:6(4z,7z,10z,13z,16z,19z)), 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)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) and cytidine monophosphate can be biosynthesized from PG(18:2(9Z,12Z)/18:2(9Z,12Z)) and CDP-DG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme cardiolipin synthase. In cattle, CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway. 1'-[1,2-Dilinoleoyl-rac-glycero-3-phospho],3'-[1,2-dieicsoate 1'-[1,2-Dilinoleoyl-rac-glycero-3-phospho],3'-[1,2-dieicsoatetraenoyl-rac-glycero-3-phospho]-glycerol 1'-[1,2-Dilinoleoyl-rac-glycero-3-phospho],3'-[1,2-dieicsoic acid Cardiolipin(18:2/18:2/20:4/20:4) Cardiolipin(18:2N6/18:2N6/20:4N3/20:4N3) Cardiolipin(18:2W6/18:2W6/20:4W3/20:4W3) Cardiolipin(76:12) Cardiolipins(18:2/18:2/20:4/20:4) Cardiolipins(18:2N6/18:2N6/20:4N3/20:4N3) Cardiolipins(18:2W6/18:2W6/20:4W3/20:4W3) Cardiolipins(76:12) CL(1'-[18:2(9Z,12Z)/18:2(9Z,12Z)],3'-[20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)]) CL(18:2/18:2/20:4/20:4) CL(18:2N6/18:2N6/20:4N3/20:4N3) CL(18:2W6/18:2W6/20:4W3/20:4W3) CL(76:12) 1'-[1,2-Di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phospho],3'-[1,2-di(8Z,11Z,14Z,17Z-eicosapentaenoyl)-rac-glycero-3-phospho]-glycerol CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) C87H142O17P2 1521.9957 1520.972226142 [3-({[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxy]phosphinic acid 3-{[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxyphosphinic acid [H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C87H142O17P2/c1-5-9-13-17-21-25-29-33-37-39-40-42-46-50-54-58-62-66-70-74-87(92)104-83(78-98-85(90)72-68-64-60-56-52-48-45-41-38-34-30-26-22-18-14-10-6-2)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/h9-10,13-14,21-28,33-38,40,42-45,48,50,54,62,66,81-83,88H,5-8,11-12,15-20,29-32,39,41,46-47,49,51-53,55-61,63-65,67-80H2,1-4H3,(H,93,94)(H,95,96)/b13-9-,14-10-,25-21-,26-22-,27-23-,28-24-,37-33-,38-34-,42-40-,43-35-,44-36-,48-45-,54-50-,66-62-/t81-,82+,83+/m0/s1 VWMKQZASGVFYFJ-VUYKTCCVSA-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 8.89 ALOGPS logs -7.21 ALOGPS logp 24.87 ChemAxon pka_strongest_acidic 1.59 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [3-({[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]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)CCCCCCC\C=C/C\C=C/CCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC ChemAxon formula C87H142O17P2 ChemAxon inchi InChI=1S/C87H142O17P2/c1-5-9-13-17-21-25-29-33-37-39-40-42-46-50-54-58-62-66-70-74-87(92)104-83(78-98-85(90)72-68-64-60-56-52-48-45-41-38-34-30-26-22-18-14-10-6-2)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/h9-10,13-14,21-28,33-38,40,42-45,48,50,54,62,66,81-83,88H,5-8,11-12,15-20,29-32,39,41,46-47,49,51-53,55-61,63-65,67-80H2,1-4H3,(H,93,94)(H,95,96)/b13-9-,14-10-,25-21-,26-22-,27-23-,28-24-,37-33-,38-34-,42-40-,43-35-,44-36-,48-45-,54-50-,66-62-/t81-,82+,83+/m0/s1 ChemAxon inchikey VWMKQZASGVFYFJ-VUYKTCCVSA-N ChemAxon polar_surface_area 236.95 ChemAxon refractivity 450.15 ChemAxon polarizability 176.23 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)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) SMP0079619 Specdb::MsMs 809836 Specdb::MsMs 809837 Specdb::MsMs 809838 Specdb::MsMs 890920 Specdb::MsMs 890921 Specdb::MsMs 890922 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 53480385 FDB027403