1.02011-09-21 01:23:34 UTC2015-07-21 06:59:06 UTCFDB027380CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:0)CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:0) is a cardiolipin (CL). Cardiolipins (bisphosphatidyl glycerol) are an important component of the inner mitochondrial membrane, where they constitute about 20% of the total lipid. Cardiolipins are a "double" phospholipid because they have four fatty acid tails, instead of the usual two. While most lipids are made in the endoplasmic reticulum, cardiolipin is synthesized on the matrix side of the inner mitochondrial membrane. They are highly abundant in metabolically active cells (heart, muscle) and play an important role in the blood clotting process. [HMDB]1'-[1-Linoleoyl-2-vaccenoyl-sn-glycero-3-O],3'-[1,2-divaccenoyl-rac-glycero-3-O]-glycerolCardiolipin(18:2/18:1/18:1/18:1)Cardiolipin(18:2N6/18:1N7/18:1N7/18:1N7)Cardiolipin(18:2W6/18:1W7/18:1W7/18:1W7)Cardiolipin(72:5)Cardiolipins(18:2/18:1/18:1/18:1)Cardiolipins(18:2N6/18:1N7/18:1N7/18:1N7)Cardiolipins(18:2W6/18:1W7/18:1W7/18:1W7)Cardiolipins(72:5)CL(1'-[18:2(9Z,12Z)/18:1(11Z)],3'-[18:1(11Z)/18:1(11Z)])CL(18:2/18:1/18:1/18:1)CL(18:2N6/18:1N7/18:1N7/18:1N7)CL(18:2W6/18:1W7/18:1W7/18:1W7)CL(72:5)C79H146O17P21429.94191429.00352627[3-({[(2R)-2-(hexadecanoyloxy)-3-(octadec-11-enoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-(octadec-11-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxy]phosphinic acid3-{[(2R)-2-(hexadecanoyloxy)-3-(octadec-11-enoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy(2R)-2-(octadec-11-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxyphosphinic acid[H][C@@](COC(=O)CCCCCCCCCC=CCCCCCC)(COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC=CCC=CCCCCC)OC(=O)CCCCCCCCCC=CCCCCCC)OC(=O)CCCCCCCCCCCCCCCInChI=1S/C79H146O17P2/c1-5-9-13-17-21-25-29-33-36-40-43-47-51-55-59-63-76(81)89-69-74(95-78(83)65-61-57-53-49-45-39-32-28-24-20-16-12-8-4)71-93-97(85,86)91-67-73(80)68-92-98(87,88)94-72-75(96-79(84)66-62-58-54-50-46-42-38-35-31-27-23-19-15-11-7-3)70-90-77(82)64-60-56-52-48-44-41-37-34-30-26-22-18-14-10-6-2/h22,25-27,29,31,34,37,73-75,80H,5-21,23-24,28,30,32-33,35-36,38-72H2,1-4H3,(H,85,86)(H,87,88)/t73?,74-,75-/m1/s1LMDGUPJGMSPFQP-LAPMJKMRSA-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.CardiolipinsOrganic compoundsLipids and lipid-like moleculesGlycerophospholipidsGlycerophosphoglycerophosphoglycerolsAliphatic acyclic compoundsCarbonyl compoundsCarboxylic acid estersDialkyl phosphatesFatty acid estersHydrocarbon derivativesOrganic oxidesSecondary alcoholsTetracarboxylic acids and derivativesAlcoholAliphatic acyclic compoundAlkyl phosphateCarbonyl groupCarboxylic acid derivativeCarboxylic acid esterCardiolipinDialkyl phosphateFatty acid esterFatty acylHydrocarbon derivativeOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganooxygen compoundPhosphoric acid esterSecondary alcoholTetracarboxylic acid or derivativesSolidlogp9.07logs-7.30solubility7.25e-05 g/llogp24.93pka_strongest_acidic1.59pka_strongest_basic-3.4iupac[3-({[(2R)-2-(hexadecanoyloxy)-3-(octadec-11-enoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-(octadec-11-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxy]phosphinic acidaverage_mass1429.9419mono_mass1429.00352627smiles[H][C@@](COC(=O)CCCCCCCCCC=CCCCCCC)(COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC=CCC=CCCCCC)OC(=O)CCCCCCCCCC=CCCCCCC)OC(=O)CCCCCCCCCCCCCCCformulaC79H146O17P2inchiInChI=1S/C79H146O17P2/c1-5-9-13-17-21-25-29-33-36-40-43-47-51-55-59-63-76(81)89-69-74(95-78(83)65-61-57-53-49-45-39-32-28-24-20-16-12-8-4)71-93-97(85,86)91-67-73(80)68-92-98(87,88)94-72-75(96-79(84)66-62-58-54-50-46-42-38-35-31-27-23-19-15-11-7-3)70-90-77(82)64-60-56-52-48-44-41-37-34-30-26-22-18-14-10-6-2/h22,25-27,29,31,34,37,73-75,80H,5-21,23-24,28,30,32-33,35-36,38-72H2,1-4H3,(H,85,86)(H,87,88)/t73?,74-,75-/m1/s1inchikeyLMDGUPJGMSPFQP-LAPMJKMRSA-Npolar_surface_area236.95refractivity402.17polarizability173.81rotatable_bond_count80acceptor_count9donor_count3physiological_charge-2formal_charge0HMDB10228Beta-2-glycoprotein 1P02749APOHCardiolipin synthaseQ9UJA2CRLS1Lysocardiolipin acyltransferase 1Q6UWP7LCLAT1