1.0 2016-10-03 18:02:46 UTC 2020-05-11 19:10:16 UTC BMDB0010265 BMDB10265 CL(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) CL(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)), also known as Cl(20:3(5z,8z,11z)/20:3(8z,11z,14z)/18:2(9z,12z)/18:2(9z,12z)) or Cl(20:3(5z,8z,11z)/20:3(8z,11z,14z)/18:2(9z,12z)/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(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). CL(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) and cytidine monophosphate can be biosynthesized from PG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) and CDP-DG(18:2(9Z,12Z)/18:2(9Z,12Z)) through the action of the enzyme cardiolipin synthase. In cattle, CL(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) pathway. 1'-[1-Meadoyl-2-homo-g-linolenoyl-sn-glycero-3-phospho],3'-[1,2-dilinoleoyl-rac-glycero-3-phospho]-glycerol 1'-[1-Meadoyl-2-homo-gamma-linolenoyl-sn-glycero-3-phospho],3'-[1,2-dilinoleoyl-rac-glycero-3-phospho]-glycerol Cardiolipin(20:3/20:3/18:2/18:2) Cardiolipin(20:3N9/20:3N6/18:2N6/18:2N6) Cardiolipin(20:3W9/20:3W6/18:2W6/18:2W6) Cardiolipin(76:10) Cardiolipins(20:3/20:3/18:2/18:2) Cardiolipins(20:3N9/20:3N6/18:2N6/18:2N6) Cardiolipins(20:3W9/20:3W6/18:2W6/18:2W6) Cardiolipins(76:10) CL(1'-[20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)],3'-[18:2(9Z,12Z)/18:2(9Z,12Z)]) CL(20:3/20:3/18:2/18:2) CL(20:3N9/20:3N6/18:2N6/18:2N6) CL(20:3W9/20:3W6/18:2W6/18:2W6) CL(76:10) 1'-[1-(5Z,8Z,11Z-Eicosatrienoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phospho],3'-[1,2-di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phospho]-glycerol CL(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) C85H146O17P2 1502.0061 1501.00352627 [3-({[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxy]phosphinic acid 3-{[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy(2R)-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]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)CCC\C=C/C\C=C/C\C=C/CCCCCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C85H146O17P2/c1-5-9-13-17-21-25-29-33-37-39-43-46-50-54-58-62-66-70-83(88)96-76-81(102-85(90)72-68-64-60-56-52-48-44-40-38-34-30-26-22-18-14-10-6-2)78-100-104(93,94)98-74-79(86)73-97-103(91,92)99-77-80(101-84(89)71-67-63-59-55-51-47-42-36-32-28-24-20-16-12-8-4)75-95-82(87)69-65-61-57-53-49-45-41-35-31-27-23-19-15-11-7-3/h22-24,26-28,33-38,41-44,46,48,54,58,79-81,86H,5-21,25,29-32,39-40,45,47,49-53,55-57,59-78H2,1-4H3,(H,91,92)(H,93,94)/b26-22-,27-23-,28-24-,37-33-,38-34-,41-35-,42-36-,46-43-,48-44-,58-54-/t79-,80-,81-/m1/s1 WPSFQIGQUMFHDO-ZVHCXAQUSA-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 9.27 ALOGPS logs -7.26 ALOGPS logp 25.43 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)-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxy]phosphinic acid ChemAxon average_mass 1502.0061 ChemAxon mono_mass 1501.00352627 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)CCC\C=C/C\C=C/C\C=C/CCCCCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC ChemAxon formula C85H146O17P2 ChemAxon inchi InChI=1S/C85H146O17P2/c1-5-9-13-17-21-25-29-33-37-39-43-46-50-54-58-62-66-70-83(88)96-76-81(102-85(90)72-68-64-60-56-52-48-44-40-38-34-30-26-22-18-14-10-6-2)78-100-104(93,94)98-74-79(86)73-97-103(91,92)99-77-80(101-84(89)71-67-63-59-55-51-47-42-36-32-28-24-20-16-12-8-4)75-95-82(87)69-65-61-57-53-49-45-41-35-31-27-23-19-15-11-7-3/h22-24,26-28,33-38,41-44,46,48,54,58,79-81,86H,5-21,25,29-32,39-40,45,47,49-53,55-57,59-78H2,1-4H3,(H,91,92)(H,93,94)/b26-22-,27-23-,28-24-,37-33-,38-34-,41-35-,42-36-,46-43-,48-44-,58-54-/t79-,80-,81-/m1/s1 ChemAxon inchikey WPSFQIGQUMFHDO-ZVHCXAQUSA-N ChemAxon polar_surface_area 236.95 ChemAxon refractivity 436.48 ChemAxon polarizability 178.44 ChemAxon rotatable_bond_count 80 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(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) SMP0079770 Specdb::MsMs 819415 Specdb::MsMs 819416 Specdb::MsMs 819417 Specdb::MsMs 894988 Specdb::MsMs 894989 Specdb::MsMs 894990 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 53480399 FDB027417