Record Information
Version2.0
Creation Date2015-09-08 19:03:52 -0600
Update Date2015-09-16 17:35:11 -0600
Secondary Accession Numbers
  • ECMDB24360
Identification
Name:CL(16:1(9Z)/19:0/16:1(9Z)/19:0)
DescriptionCL(16:1(9Z)/19:0/16:1(9Z)/19:0) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(16:1(9Z)/19:0/16:1(9Z)/19:0) contains two chains of (9Z-hexadecenoyl) at the C1 and C3 positions, two chains of nonadecanoic acid 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
Thumb
Synonyms:Not Available
Chemical Formula:C79H150O17P2
Weight:Average: 1434.0
Monoisotopic: 1433.034827366
InChI Key:AYUOFPQDYLBQHE-VOUAAHEJSA-N
InChI:InChI=1S/C79H150O17P2/c1-5-9-13-17-21-25-29-33-35-37-41-45-49-53-57-61-65-78(83)95-74(69-89-76(81)63-59-55-51-47-43-39-31-27-23-19-15-11-7-3)71-93-97(85,86)91-67-73(80)68-92-98(87,88)94-72-75(70-90-77(82)64-60-56-52-48-44-40-32-28-24-20-16-12-8-4)96-79(84)66-62-58-54-50-46-42-38-36-34-30-26-22-18-14-10-6-2/h27-28,31-32,73-75,80H,5-26,29-30,33-72H2,1-4H3,(H,85,86)(H,87,88)/b31-27-,32-28-/t74-,75-/m1/s1
CAS number:Not Available
IUPAC Name:[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-(nonadecanoyloxy)propoxy][3-({[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-(nonadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name:(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-(nonadecanoyloxy)propoxy(3-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-(nonadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
SMILES:[H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCC
Chemical Taxonomy
ClassificationNot classified
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility7.1e-05 g/LALOGPS
logP9.05ALOGPS
logP25.66ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)1.59ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area236.95 ŲChemAxon
Rotatable Bond Count82ChemAxon
Refractivity399.94 m³·mol⁻¹ChemAxon
Polarizability172.61 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
phospholipid biosynthesis (CL(16:1(9Z)/19:0/16:1(9Z)/19:0))PW001962 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
0.04962± 0.0 uMK12Luria-Bertani (LB) mediaStationary phase cultures (overnight culture)Shake flask37 oCPMID: 22956318
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00m0-0790621330-be63e2433f881408948eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fsu-0590212140-5e80352125fa0f958607View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w3d-0392251330-096b8f8f614393874c54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uei-0290200010-89d58f7e6ed79ac3fab8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ug0-2190101010-af62c4a33884df271172View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9080003000-58a2fc34ceb354e04975View in MoNA
References
References:
  • De Siervo, A. J. (1969). "Alterations in the phospholipid composition of Escherichia coli B during growth at different temperatures." J Bacteriol 100:1342-1349. Pubmed: 4902814
  • Garrett, T. A., O'Neill, A. C., Hopson, M. L. (2012). "Quantification of cardiolipin molecular species in Escherichia coli lipid extracts using liquid chromatography/electrospray ionization mass spectrometry." Rapid Commun Mass Spectrom 26:2267-2274. Pubmed: 22956318
  • 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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. Pubmed: 22102590
  • 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
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
cardiolipin biosynthetic process
Specific function:
Catalyzes the synthesis of cardiolipin (CL) (diphosphatidylglycerol) from phosphatidylglycerol (PG) and phosphatidylethanolamine (PE).
Gene Name:
clsC
Uniprot ID:
P75919
Molecular weight:
53665
Reactions
Phosphatidylglycerol + phosphatidylethanolamine = diphosphatidylglycerol + ethanolamine