1.0 2011-09-21 01:24:29 UTC 2015-07-21 06:59:07 UTC FDB027444 CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)) CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)) 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] C85H146O17P2 1502.0061 1501.00352627 [3-({[(2R)-2,3-bis(octadec-11-enoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-(docosa-4,7,10,13,16,19-hexaenoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxy]phosphinic acid 3-{[(2R)-2,3-bis(octadec-11-enoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy(2R)-3-(docosa-4,7,10,13,16,19-hexaenoyloxy)-2-(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)CCC=CCC=CCC=CCC=CCC=CCC=CCC)OC(=O)CCCCCCCC=CCC=CCCCCC)OC(=O)CCCCCCCCCC=CCCCCCC InChI=1S/C85H146O17P2/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/h9,13,21,24-28,30-31,33,36-37,39-40,43,46,50,58,62,79-81,86H,5-8,10-12,14-20,22-23,29,32,34-35,38,41-42,44-45,47-49,51-57,59-61,63-78H2,1-4H3,(H,91,92)(H,93,94)/t79?,80-,81-/m1/s1 OFXMWINBKIDVBY-NYTMHASESA-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. Cardiolipins Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphoglycerophosphoglycerols Aliphatic acyclic compounds Carbonyl compounds Carboxylic acid esters Dialkyl phosphates Fatty acid esters Hydrocarbon derivatives Organic oxides Secondary alcohols Tetracarboxylic acids and derivatives Alcohol Aliphatic acyclic compound Alkyl phosphate Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cardiolipin Dialkyl phosphate Fatty acid ester Fatty acyl Hydrocarbon derivative Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organooxygen compound Phosphoric acid ester Secondary alcohol Tetracarboxylic acid or derivatives Solid logp 9.28 ALOGPS logs -7.28 ALOGPS solubility 7.91e-05 g/l ALOGPS logp 25.43 ChemAxon pka_strongest_acidic 1.59 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [3-({[(2R)-2,3-bis(octadec-11-enoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-(docosa-4,7,10,13,16,19-hexaenoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxy]phosphinic acid ChemAxon average_mass 1502.0061 ChemAxon mono_mass 1501.00352627 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCC=CCCCCCC)(COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC=CCC=CCC=CCC=CCC=CCC=CCC)OC(=O)CCCCCCCC=CCC=CCCCCC)OC(=O)CCCCCCCCCC=CCCCCCC ChemAxon formula C85H146O17P2 ChemAxon inchi InChI=1S/C85H146O17P2/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/h9,13,21,24-28,30-31,33,36-37,39-40,43,46,50,58,62,79-81,86H,5-8,10-12,14-20,22-23,29,32,34-35,38,41-42,44-45,47-49,51-57,59-61,63-78H2,1-4H3,(H,91,92)(H,93,94)/t79?,80-,81-/m1/s1 ChemAxon inchikey OFXMWINBKIDVBY-NYTMHASESA-N ChemAxon polar_surface_area 236.95 ChemAxon refractivity 436.48 ChemAxon polarizability 181.04 ChemAxon rotatable_bond_count 80 ChemAxon acceptor_count 9 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon HMDB10292 Beta-2-glycoprotein 1 P02749 APOH Cardiolipin synthase Q9UJA2 CRLS1 Lysocardiolipin acyltransferase 1 Q6UWP7 LCLAT1