Record Information |
---|
Version | 2.0 |
---|
Creation Date | 2012-10-04 10:00:48 -0600 |
---|
Update Date | 2015-09-16 17:34:45 -0600 |
---|
Secondary Accession Numbers | |
---|
Identification |
---|
Name: | CL(14:0/16:1(9Z)/14:0/16:1(9Z)) |
---|
Description | CL(14:0/16:1(9Z)/14:0/16:1(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(14:0/16:1(9Z)/14:0/16:1(9Z)) contains two chains of tetradecanoic acid at the C1 and C3 positions, two chains of (9Z-hexadecenoyl) at the C2 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: | - 1'-[1-myristoyl-2-palmitoleoyl-sn-glycero-3-phospho],3'-[1,2-dimyristoyl-rac-glycero-3-phospho]-glycerol
- 1'-[1-tetradecanoyl,2-(9Z-hexadecenoyl)-sn-glycero-3-phospho],3'-[1-tetradecanoyl,2-(9Z-hexadecenoyl)-sn-glycero-3-phospho]-sn-glycerol
- 1'-[1-tetradecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho],3'-[1,2-ditetradecanoyl-rac-glycero-3-phospho]-glycerol
- Cardiolipin(14:0/16:1/14:0/14:0)
- Cardiolipin(58:1)
- CL(1'-[14:0/16:1(9Z)],3'-[14:0/14:0])
- CL(14:0/16:1/14:0/14:0)
- CL(58:1)
|
---|
Chemical Formula: | C69H130O17P2 |
---|
Weight: | Average: 1293.7078 Monoisotopic: 1292.878325758 |
---|
InChI Key: | DTXBWVGPEHJQBX-MKIXNFRGSA-N |
---|
InChI: | InChI=1S/C69H130O17P2/c1-5-9-13-17-21-25-29-31-35-39-43-47-51-55-68(73)85-64(59-79-66(71)53-49-45-41-37-33-27-23-19-15-11-7-3)61-83-87(75,76)81-57-63(70)58-82-88(77,78)84-62-65(60-80-67(72)54-50-46-42-38-34-28-24-20-16-12-8-4)86-69(74)56-52-48-44-40-36-32-30-26-22-18-14-10-6-2/h25-26,29-30,63-65,70H,5-24,27-28,31-62H2,1-4H3,(H,75,76)(H,77,78)/b29-25-,30-26-/t64-,65-/m1/s1 |
---|
CAS number: | Not Available |
---|
IUPAC Name: | [(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy][3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid |
---|
Traditional IUPAC Name: | (2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy(3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid |
---|
SMILES: | CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@H](COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC |
---|
Chemical Taxonomy |
---|
Classification | Not classified |
---|
Physical Properties |
---|
State: | Solid |
---|
Charge: | -2 |
---|
Melting point: | Not Available |
---|
Experimental Properties: | |
---|
Predicted Properties | |
---|
Biological Properties |
---|
Cellular Locations: | Membrane |
---|
Reactions: | |
---|
SMPDB Pathways: | phospholipid biosynthesis CL(14:0/16:1(9Z)/14:0/16:1(9Z)) | PW001039 | |
|
---|
KEGG Pathways: | - Glycerophospholipid metabolism ec00564
|
---|
EcoCyc Pathways: | Not Available |
---|
Concentrations |
---|
| Concentration | Strain | Media | Growth Status | Growth System | Temperature | Details |
---|
0.06441± 0.0 uM | K12 | Luria-Bertani (LB) media | Stationary phase cultures (overnight culture) | Shake flask | 37 oC | PMID: 22956318 |
|
---|
Spectra |
---|
Spectra: | |
---|
References |
---|
References: | - Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
|
---|
Synthesis Reference: | Not Available |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
Links |
---|
External Links: | Resource | Link |
---|
CHEBI ID | Not Available | HMDB ID | Not Available | Pubchem Compound ID | Not Available | Kegg ID | Not Available | ChemSpider ID | Not Available | Wikipedia ID | Not Available | BioCyc ID | Not Available |
|
---|