CL(16:0/14:0/16:0/14:0) (PAMDB002624)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB002624
Identification
Name: CL(16:0/14:0/16:0/14:0)
Description:CL(16:0/14:0/16:0/14:0) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(16:0/14:0/16:0/14:0) contains two chains of hexadecanoic acid at the C1 and C3 positions, two chains of tetradecanoic 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 Pseudomonas aeruginosa, 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 Pseudomonas aeruginosa, 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. Pseudomonas aeruginosa 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 Pseudomonas aeruginosa and other rod-shaped bacteria. It is known that the polar positioning of the proline transporter ProP and the mechanosensitive ion channel MscS in Pseudomonas aeruginosa 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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1'-[1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phospho],3'-[1,2-dihexadecanoyl-rac-glycero-3-phospho]-glycerol
  • 1'-[1-palmitoyl-2-myristoyl-sn-glycero-3-phospho],3'-[1,2-dipalmitoyl-rac-glycero-3-phospho]-glycerol
  • Cardiolipin(16:0/14:0/16:0/16:0)
  • Cardiolipin(62:0)
  • CL(1'-[16:0/14:0],3'-[16:0/16:0])
  • CL(16:0/14:0/16:0/16:0)
  • CL(62:0)
Chemical Formula: C69H134O17P2
Average Molecular Weight: 1297.7396
Monoisotopic Molecular Weight: 1296.909625886
InChI Key: UFLDMQPZLYVSTB-WXQUPVAFSA-N
InChI:InChI=1S/C69H134O17P2/c1-5-9-13-17-21-25-29-31-35-37-41-45-49-53-66(71)79-59-64(85-68(73)55-51-47-43-39-33-27-23-19-15-11-7-3)61-83-87(75,76)81-57-63(70)58-82-88(77,78)84-62-65(86-69(74)56-52-48-44-40-34-28-24-20-16-12-8-4)60-80-67(72)54-50-46-42-38-36-32-30-26-22-18-14-10-6-2/h63-65,70H,5-62H2,1-4H3,(H,75,76)(H,77,78)/t64-,65-/m1/s1
CAS number: Not Available
IUPAC Name:[(2R)-3-(hexadecanoyloxy)-2-(tetradecanoyloxy)propoxy][3-({[(2R)-3-(hexadecanoyloxy)-2-(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name: (2R)-3-(hexadecanoyloxy)-2-(tetradecanoyloxy)propoxy(3-{[(2R)-3-(hexadecanoyloxy)-2-(tetradecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
SMILES:CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC
Chemical Taxonomy
Taxonomy DescriptionThis compound 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-diacylglyerol 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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphoglycerophosphoglycerols
Direct Parent Cardiolipins
Alternative Parents
Substituents
  • Cardiolipin
  • Tetracarboxylic acid or derivatives
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00011 mg/mLALOGPS
logP8.7ALOGPS
logP21.93ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)1.59ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area236.95 Å2ChemAxon
Rotatable Bond Count74ChemAxon
Refractivity351.7 m3·mol-1ChemAxon
Polarizability154.83 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
PE(14:0/16:0) + PG(14:0/16:0) > Ethanolamine + CL(16:0/14:0/16:0/14:0)
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02dj-4090012010-894170bee2de0f2cd082View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-4190024200-f653905933939ba11850View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2491156100-92df2859e6052b380f85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a70-2090000000-faa3f99e1f822e9ad647View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-3090001100-724ea41420dab0cb8e56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-8090003000-35a35a01034ea9fc0889View 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
  • 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