1.0 2016-10-03 18:03:07 UTC 2020-05-11 19:10:26 UTC BMDB0010278 BMDB10278 CL(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) CL(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/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(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) and cytidine monophosphate can be biosynthesized from PG(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)) and CDP-DG(18:2(9Z,12Z)/18:2(9Z,12Z)); which is mediated by the enzyme cardiolipin synthase. In cattle, CL(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) pathway. 1'-[1-Eicsoate 1'-[1-Eicsoatetraenoyl-2-linoleoyl-sn-glycero-3-phospho],3'-[1,2-dilinoleoyl-rac-glycero-3-phospho]-glycerol 1'-[1-Eicsoic acid Cardiolipin(20:4/18:2/18:2/18:2) Cardiolipin(20:4N3/18:2N6/18:2N6/18:2N6) Cardiolipin(20:4W3/18:2W6/18:2W6/18:2W6) Cardiolipin(74:10) Cardiolipins(20:4/18:2/18:2/18:2) Cardiolipins(20:4N3/18:2N6/18:2N6/18:2N6) Cardiolipins(20:4W3/18:2W6/18:2W6/18:2W6) Cardiolipins(74:10) CL(1'-[20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)],3'-[18:2(9Z,12Z)/18:2(9Z,12Z)]) CL(20:4/18:2/18:2/18:2) CL(20:4N3/18:2N6/18:2N6/18:2N6) CL(20:4W3/18:2W6/18:2W6/18:2W6) CL(74:10) 1'-[1-(8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho],3'-[1,2-di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phospho]-glycerol CL(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) C83H142O17P2 1473.9529 1472.972226142 [3-({[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid 3-{[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy(2R)-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]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)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C83H142O17P2/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/h9,13,21-28,33-37,39-42,44,77-79,84H,5-8,10-12,14-20,29-32,38,43,45-76H2,1-4H3,(H,89,90)(H,91,92)/b13-9-,25-21-,26-22-,27-23-,28-24-,37-33-,39-34-,40-35-,41-36-,44-42-/t77-,78-,79-/m1/s1 OWMMDKMOIBQBBL-FXMCMXGRSA-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 24.54 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-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid ChemAxon average_mass 1473.9529 ChemAxon mono_mass 1472.972226142 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)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC ChemAxon formula C83H142O17P2 ChemAxon inchi InChI=1S/C83H142O17P2/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/h9,13,21-28,33-37,39-42,44,77-79,84H,5-8,10-12,14-20,29-32,38,43,45-76H2,1-4H3,(H,89,90)(H,91,92)/b13-9-,25-21-,26-22-,27-23-,28-24-,37-33-,39-34-,40-35-,41-36-,44-42-/t77-,78-,79-/m1/s1 ChemAxon inchikey OWMMDKMOIBQBBL-FXMCMXGRSA-N ChemAxon polar_surface_area 236.95 ChemAxon refractivity 427.28 ChemAxon polarizability 171.61 ChemAxon rotatable_bond_count 78 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(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) SMP0080008 Specdb::MsMs 826885 Specdb::MsMs 826886 Specdb::MsMs 826887 Specdb::MsMs 898246 Specdb::MsMs 898247 Specdb::MsMs 898248 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 53480412 FDB027430