1.0 2016-10-03 18:02:36 UTC 2020-05-11 19:10:11 UTC BMDB0010259 BMDB10259 CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)), also known as Cl(20:1(11z)/18:2(9z,12z)/18:2(9z,12z)/18:1(9z)) or Cl(20:1(11z)/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(20:1(11Z)/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(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) and cytidine monophosphate can be biosynthesized from PG(20:1(11Z)/18:2(9Z,12Z)) and CDP-DG(18:2(9Z,12Z)/18:1(9Z)) through the action of the enzyme cardiolipin synthase. In cattle, CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) pathway. 1'-[1-Eicosenoyl-2-linoleoyl-sn-glycero-3-phospho],3'-[1,2-dilinoleoyl-rac-glycero-3-phospho]-glycerol Cardiolipin(20:1/18:2/18:2/18:2) Cardiolipin(20:1N9/18:2N6/18:2N6/18:2N6) Cardiolipin(20:1W9/18:2W6/18:2W6/18:2W6) Cardiolipin(74:7) Cardiolipins(20:1/18:2/18:2/18:2) Cardiolipins(20:1N9/18:2N6/18:2N6/18:2N6) Cardiolipins(20:1W9/18:2W6/18:2W6/18:2W6) Cardiolipins(74:7) CL(1'-[20:1(11Z)/18:2(9Z,12Z)],3'-[18:2(9Z,12Z)/18:2(9Z,12Z)]) CL(20:1/18:2/18:2/18:2) CL(20:1N9/18:2N6/18:2N6/18:2N6) CL(20:1W9/18:2W6/18:2W6/18:2W6) CL(74:7) 1'-[1-(11-Eicosenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho],3'-[1,2-di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phospho]-glycerol CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) C83H150O17P2 1482.0164 1481.034826398 [2-hydroxy-3-({hydroxy[(2R)-3-[(11Z)-icos-11-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)propoxy][(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid 2-hydroxy-3-{[hydroxy(2R)-3-[(11Z)-icos-11-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphoryl]oxy}propoxy(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphinic acid [H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C83H150O17P2/c1-5-9-13-17-21-25-29-33-37-38-42-44-48-52-56-60-64-68-81(86)94-74-79(100-83(88)70-66-62-58-54-50-46-41-36-32-28-24-20-16-12-8-4)76-98-102(91,92)96-72-77(84)71-95-101(89,90)97-75-78(99-82(87)69-65-61-57-53-49-45-40-35-31-27-23-19-15-11-7-3)73-93-80(85)67-63-59-55-51-47-43-39-34-30-26-22-18-14-10-6-2/h22,24,26,28,33-37,39-41,77-79,84H,5-21,23,25,27,29-32,38,42-76H2,1-4H3,(H,89,90)(H,91,92)/b26-22-,28-24-,37-33-,39-34-,40-35-,41-36-/t77-,78-,79-/m1/s1 QLPIJRMQCFAGOH-YDDLFNMJSA-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 9.20 ALOGPS logs -7.30 ALOGPS logp 25.99 ChemAxon pka_strongest_acidic 1.59 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [2-hydroxy-3-({hydroxy[(2R)-3-[(11Z)-icos-11-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)propoxy][(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid ChemAxon average_mass 1482.0164 ChemAxon mono_mass 1481.034826398 ChemAxon smiles [H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC ChemAxon formula C83H150O17P2 ChemAxon inchi InChI=1S/C83H150O17P2/c1-5-9-13-17-21-25-29-33-37-38-42-44-48-52-56-60-64-68-81(86)94-74-79(100-83(88)70-66-62-58-54-50-46-41-36-32-28-24-20-16-12-8-4)76-98-102(91,92)96-72-77(84)71-95-101(89,90)97-75-78(99-82(87)69-65-61-57-53-49-45-40-35-31-27-23-19-15-11-7-3)73-93-80(85)67-63-59-55-51-47-43-39-34-30-26-22-18-14-10-6-2/h22,24,26,28,33-37,39-41,77-79,84H,5-21,23,25,27,29-32,38,42-76H2,1-4H3,(H,89,90)(H,91,92)/b26-22-,28-24-,37-33-,39-34-,40-35-,41-36-/t77-,78-,79-/m1/s1 ChemAxon inchikey QLPIJRMQCFAGOH-YDDLFNMJSA-N ChemAxon polar_surface_area 236.95 ChemAxon refractivity 422.81 ChemAxon polarizability 177.61 ChemAxon rotatable_bond_count 82 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(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) SMP0079764 Specdb::MsMs 868735 Specdb::MsMs 868736 Specdb::MsMs 868737 Specdb::MsMs 916051 Specdb::MsMs 916052 Specdb::MsMs 916053 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 35031997 FDB027411 53480393