1.0 2016-10-03 18:03:46 UTC 2020-05-11 19:10:44 UTC BMDB0010299 BMDB10299 CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)), also known as Cl(22:6(4z,7z,10z,13z,16z,19z)/18:2(9z,12z)/18:2(9z,12z)/18:1(9z)) or Cl(22:6(4z,7z,10z,13z,16z,19z)/18:2(9z,12z)/18:2(9z,12z)/18:1(9z)), 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)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) 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)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) and cytidine monophosphate can be biosynthesized from PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) and CDP-DG(18:2(9Z,12Z)/18:1(9Z)); which is catalyzed by the enzyme cardiolipin synthase. In cattle, CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) pathway. 1'-[1-Docosahexaenoyl-2-linoleoyl-sn-glycero-3-phospho],3'-[1,2-dilinoleoyl-rac-glycero-3-phospho]-glycerol Cardiolipin(22:6/18:2/18:2/18:2) Cardiolipin(22:6N3/18:2N6/18:2N6/18:2N6) Cardiolipin(22:6W3/18:2W6/18:2W6/18:2W6) Cardiolipin(76:12) Cardiolipins(22:6/18:2/18:2/18:2) Cardiolipins(22:6N3/18:2N6/18:2N6/18:2N6) Cardiolipins(22:6W3/18:2W6/18:2W6/18:2W6) Cardiolipins(76:12) CL(1'-[22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)],3'-[18:2(9Z,12Z)/18:2(9Z,12Z)]) CL(22:6/18:2/18:2/18:2) CL(22:6N3/18:2N6/18:2N6/18:2N6) CL(22:6W3/18:2W6/18:2W6/18:2W6) CL(76:12) 1'-[1-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho],3'-[1,2-di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phospho]-glycerol CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) C85H144O17P2 1499.9902 1498.987876206 [(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy][2-hydroxy-3-({hydroxy[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(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-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy(2-hydroxy-3-{[hydroxy((2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy)phosphoryl]oxy}propoxy)phosphinic acid [H][C@@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC)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)CCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C85H144O17P2/c1-5-9-13-17-21-25-29-33-37-38-39-40-44-46-50-54-58-62-66-70-83(88)96-76-81(102-85(90)72-68-64-60-56-52-48-43-36-32-28-24-20-16-12-8-4)78-100-104(93,94)98-74-79(86)73-97-103(91,92)99-77-80(101-84(89)71-67-63-59-55-51-47-42-35-31-27-23-19-15-11-7-3)75-95-82(87)69-65-61-57-53-49-45-41-34-30-26-22-18-14-10-6-2/h9,13,21-22,24-26,28,33-37,39-43,46,50,58,62,79-81,86H,5-8,10-12,14-20,23,27,29-32,38,44-45,47-49,51-57,59-61,63-78H2,1-4H3,(H,91,92)(H,93,94)/b13-9-,25-21-,26-22-,28-24-,37-33-,40-39-,41-34-,42-35-,43-36-,50-46-,62-58-/t79-,80-,81-/m1/s1 WMLJFTSYUGZRGY-KFCNVDEMSA-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 9.19 ALOGPS logs -7.25 ALOGPS logp 25.07 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-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy][2-hydroxy-3-({hydroxy[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphinic acid ChemAxon average_mass 1499.9902 ChemAxon mono_mass 1498.987876206 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/CCCCCCCC)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)CCCCCCC\C=C/C\C=C/CCCCC ChemAxon formula C85H144O17P2 ChemAxon inchi InChI=1S/C85H144O17P2/c1-5-9-13-17-21-25-29-33-37-38-39-40-44-46-50-54-58-62-66-70-83(88)96-76-81(102-85(90)72-68-64-60-56-52-48-43-36-32-28-24-20-16-12-8-4)78-100-104(93,94)98-74-79(86)73-97-103(91,92)99-77-80(101-84(89)71-67-63-59-55-51-47-42-35-31-27-23-19-15-11-7-3)75-95-82(87)69-65-61-57-53-49-45-41-34-30-26-22-18-14-10-6-2/h9,13,21-22,24-26,28,33-37,39-43,46,50,58,62,79-81,86H,5-8,10-12,14-20,23,27,29-32,38,44-45,47-49,51-57,59-61,63-78H2,1-4H3,(H,91,92)(H,93,94)/b13-9-,25-21-,26-22-,28-24-,37-33-,40-39-,41-34-,42-35-,43-36-,50-46-,62-58-/t79-,80-,81-/m1/s1 ChemAxon inchikey WMLJFTSYUGZRGY-KFCNVDEMSA-N ChemAxon polar_surface_area 236.95 ChemAxon refractivity 437.6 ChemAxon polarizability 174.84 ChemAxon rotatable_bond_count 79 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)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) SMP0080401 Specdb::MsMs 840328 Specdb::MsMs 840329 Specdb::MsMs 840330 Specdb::MsMs 903862 Specdb::MsMs 903863 Specdb::MsMs 903864 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 53480433 FDB027451