1.0 2016-10-03 18:02:30 UTC 2020-05-11 19:10:07 UTC BMDB0010255 BMDB10255 CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)) CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)), also known as Cl(20:1(11z)/18:2(9z,12z)/18:1(11z)/18:1(9z)) or Cl(20:1(11z)/18:2(9z,12z)/18:1(11z)/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)/18:1(11Z)/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)/18:1(11Z)/18:1(9Z)) and cytidine monophosphate can be biosynthesized from PG(20:1(11Z)/18:2(9Z,12Z)) and CDP-DG(18:1(11Z)/18:1(9Z)); which is catalyzed by the enzyme cardiolipin synthase. In cattle, CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)) pathway. 1'-[1-Eicosenoyl-2-linoleoyl-sn-glycero-3-phospho],3'-[1,2-divaccenoyl-rac-glycero-3-phospho]-glycerol Cardiolipin(20:1/18:2/18:1/18:1) Cardiolipin(20:1N9/18:2N6/18:1N7/18:1N7) Cardiolipin(20:1W9/18:2W6/18:1W7/18:1W7) Cardiolipin(74:5) Cardiolipins(20:1/18:2/18:1/18:1) Cardiolipins(20:1N9/18:2N6/18:1N7/18:1N7) Cardiolipins(20:1W9/18:2W6/18:1W7/18:1W7) Cardiolipins(74:5) CL(1'-[20:1(11Z)/18:2(9Z,12Z)],3'-[18:1(11Z)/18:1(11Z)]) CL(20:1/18:2/18:1/18:1) CL(20:1N9/18:2N6/18:1N7/18:1N7) CL(20:1W9/18:2W6/18:1W7/18:1W7) CL(74:5) 1'-[1-(11-Eicosenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho],3'-[1,2-di(11Z-octadecenoyl)-rac-glycero-3-phospho]-glycerol CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)) C83H152O17P2 1484.0323 1483.050476462 [2-hydroxy-3-({hydroxy[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy][(2R)-3-[(11Z)-icos-11-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid 2-hydroxy-3-{[hydroxy(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxyphosphoryl]oxy}propoxy(2R)-3-[(11Z)-icos-11-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphinic acid [H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C83H152O17P2/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/h24,26,28,30,33,35-37,40-41,77-79,84H,5-23,25,27,29,31-32,34,38-39,42-76H2,1-4H3,(H,89,90)(H,91,92)/b28-24-,30-26-,37-33-,40-35-,41-36-/t77-,78-,79-/m1/s1 UJNOBFXXRICQCY-OEKNKJGFSA-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 9.16 ALOGPS logs -7.28 ALOGPS logp 26.35 ChemAxon pka_strongest_acidic 1.59 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [2-hydroxy-3-({hydroxy[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy][(2R)-3-[(11Z)-icos-11-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid ChemAxon average_mass 1484.0323 ChemAxon mono_mass 1483.050476462 ChemAxon smiles [H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC ChemAxon formula C83H152O17P2 ChemAxon inchi InChI=1S/C83H152O17P2/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/h24,26,28,30,33,35-37,40-41,77-79,84H,5-23,25,27,29,31-32,34,38-39,42-76H2,1-4H3,(H,89,90)(H,91,92)/b28-24-,30-26-,37-33-,40-35-,41-36-/t77-,78-,79-/m1/s1 ChemAxon inchikey UJNOBFXXRICQCY-OEKNKJGFSA-N ChemAxon polar_surface_area 236.95 ChemAxon refractivity 421.69 ChemAxon polarizability 178.15 ChemAxon rotatable_bond_count 83 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)/18:1(11Z)/18:1(9Z)) SMP0079760 Specdb::MsMs 822418 Specdb::MsMs 822419 Specdb::MsMs 822420 Specdb::MsMs 896335 Specdb::MsMs 896336 Specdb::MsMs 896337 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 53480389 FDB027407