Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 00:17:14 UTC
Update Date2024-04-30 19:47:43 UTC
Metabolite IDMMDBc0030663
Metabolite Identification
Common NameCL(16:0/16:1(9Z)/18:1(9Z)/18:1(9Z))
DescriptionCL(16:0/16:1(9Z)/18:1(9Z)/18:1(9Z)) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(16:0/16:1(9Z)/18:1(9Z)/18:1(9Z)) contains one chain of hexadecanoic acid at the C1 position, one chain of (9Z-hexadecenoyl) at the C2 position, two chains of (9Z-octadecenoyl) at the C3 and C4 positions. While the theoretical charge of cardiolipins is -2, under normal physiological conditions (pH near 7), the molecule may carry only one negative charge. In prokaryotes such as E. coli, the enzyme known as diphosphatidylglycerol synthase catalyses the transfer of the phosphatidyl moiety of one phosphatidylglycerol to the free 3'-hydroxyl group of another, with the elimination of one molecule of glycerol. In E. coli, which acylates its glycerophospholipids with acyl chains ranging in length from 12 to 19 carbons and possibly containing an unsaturation, or a cyclopropane group more than 100 possible CL molecular species are theoretically possible. E. coli membranes consist of ~5% cardiolipin (CL), 20-25% phosphatidylglycerol (PG), and 70-80% phosphatidylethanolamine (PE) as well as smaller amounts of phosphatidylserine (PS). CL is distributed between the two leaflets of the bilayers and is located preferentially at the poles and septa in E. coli and other rod-shaped bacteria. It is known that the polar positioning of the proline transporter ProP and the mechanosensitive ion channel MscS in E. coli is dependent on CL. It is believed that cell shape may influence the localization of CL and the localization of certain membrane proteins.
Structure
Synonyms
ValueSource
Cardiolipin(16:0/16:1/18:1/18:1)HMDB
1'-[1-Palmitoyl-2-palmitoleoyl-sn-glycero-3-phospho],3'-[1,2-dioleoyl-rac-glycero-3-phospho]-glycerolHMDB
CL(1'-[16:0/16:1(9Z)],3'-[18:1(9Z)/18:1(9Z)])HMDB
CL(16:0/16:1/18:1/18:1)HMDB
Cardiolipin(68:3)HMDB
CL(68:3)HMDB
1'-[1-Hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho],3'-[1,2-di(9Z-octadecenoyl)-rac-glycero-3-phospho]-glycerolHMDB
CL(16:0/16:1(9Z)/18:1(9Z)/18:1(9Z))Lipid Annotator
Molecular FormulaC77H144O17P2
Average Mass1403.93
Monoisotopic Mass1402.987877173
IUPAC Name[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy][(2S)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional Name(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy((2S)-3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C77H144O17P2/c1-5-9-13-17-21-25-29-33-35-39-42-46-50-54-58-62-75(80)88-68-73(94-77(82)64-60-56-52-48-44-40-36-34-30-26-22-18-14-10-6-2)70-92-96(85,86)90-66-71(78)65-89-95(83,84)91-69-72(93-76(81)63-59-55-51-47-43-38-32-28-24-20-16-12-8-4)67-87-74(79)61-57-53-49-45-41-37-31-27-23-19-15-11-7-3/h28,32-36,71-73,78H,5-27,29-31,37-70H2,1-4H3,(H,83,84)(H,85,86)/b32-28-,35-33-,36-34-/t71-,72+,73+/m0/s1
InChI KeyRINNQSJWQUKHOK-PFZQSILNSA-N