CL(16:1(9Z)/19:0/16:0/16:0) (ECMDB24359) (M2MDB006476)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (1)
Record Information
Version2.0
Creation Date2015-09-08 19:03:42 -0600
Update Date2015-12-09 12:02:50 -0700
Secondary Accession Numbers
  • ECMDB24359
Identification
Name:CL(16:1(9Z)/19:0/16:0/16:0)
DescriptionCL(16:1(9Z)/19:0/16:0/16:0) 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)/19:0/16:0/16:0) contains one chain of (9Z-hexadecenoyl) at the C1 position, one chain of nonadecanoic acid at the C2 position, two chains of hexadecanoic acid 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms:Not Available
Chemical Formula:C76H146O17P2
Weight:Average: 1393.935
Monoisotopic: 1393.003527237
InChI Key:LEUWKDSQWUSECF-VPMLYHEASA-N
InChI:InChI=1S/C76H146O17P2/c1-5-9-13-17-21-25-29-33-34-35-39-43-47-51-55-59-63-76(81)93-72(67-87-74(79)61-57-53-49-45-41-37-31-27-23-19-15-11-7-3)69-91-95(84,85)89-65-70(77)64-88-94(82,83)90-68-71(92-75(80)62-58-54-50-46-42-38-32-28-24-20-16-12-8-4)66-86-73(78)60-56-52-48-44-40-36-30-26-22-18-14-10-6-2/h27,31,70-72,77H,5-26,28-30,32-69H2,1-4H3,(H,82,83)(H,84,85)/b31-27-/t70-,71-,72-/m1/s1
CAS number:Not Available
IUPAC Name:[(2R)-3-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-(nonadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name:(2R)-3-{[(2R)-2,3-bis(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-(nonadecanoyloxy)propoxy)phosphinic acid
SMILES:[H][C@@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCC
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerophosphoglycerols
Direct ParentCardiolipins
Alternative Parents
Substituents
  • Cardiolipin
  • Tetracarboxylic acid or derivatives
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility7.3e-05 g/LALOGPS
logP8.95ALOGPS
logP24.68ChemAxon
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 Count80ChemAxon
Refractivity385.02 m³·mol⁻¹ChemAxon
Polarizability169.33 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
PE(16:1(9Z)/19:0) + PG(16:0/16:0) > Ethanolamine + CL(16:1(9Z)/19:0/16:0/16:0)
SMPDB Pathways:
phospholipid biosynthesis (CL(16:1(9Z)/19:0/16:0/16:0))PW001961 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
0.04144± 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, Positivesplash10-002u-2987041350-f3c71cd32f8b764507f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002v-1593033240-04206e780959ce2f8e52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gvn-2198172320-481c55d9d123f47b5a89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052u-1391001010-60769f1307a1e1d4433eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kdr-5191001020-b5fc7ee99ddea7ac9318View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9070003000-1985c0f10cbcbba89c6fView 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

Protein Details
1. Cardiolipin synthase C
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