CL(14:0(3-OH)/12:0(3-OH)/14:0(3-OH)/12:0(3-OH)) (PAMDB006984)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB006984
Identification
Name: CL(14:0(3-OH)/12:0(3-OH)/14:0(3-OH)/12:0(3-OH))
Description:CL(14:0(3-OH)/12:0(3-OH)/14:0(3-OH)/12:0(3-OH)) 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(3-OH)/12:0(3-OH)/14:0(3-OH)/12:0(3-OH)) contains two chains of 3-hydroxytetradecanoic acid at the C1 and C3 positions, two chains of 3-hydroxydodecanoic 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:Not Available
Chemical Formula: C61H118O21P2
Average Molecular Weight: 1249.542
Monoisotopic Molecular Weight: 1248.764084816
InChI Key: BSPIXAHNIJSALC-LPRALUPZSA-N
InChI:InChI=1S/C61H118O21P2/c1-5-9-13-17-21-23-27-31-33-37-51(62)41-58(67)75-47-56(81-60(69)43-53(64)39-35-29-25-19-15-11-7-3)49-79-83(71,72)77-45-55(66)46-78-84(73,74)80-50-57(82-61(70)44-54(65)40-36-30-26-20-16-12-8-4)48-76-59(68)42-52(63)38-34-32-28-24-22-18-14-10-6-2/h51-57,62-66H,5-50H2,1-4H3,(H,71,72)(H,73,74)/t51?,52?,53?,54?,55?,56-,57-/m1/s1
CAS number: Not Available
IUPAC Name:[2-hydroxy-3-({hydroxy[(2R)-2-[(3-hydroxydodecanoyl)oxy]-3-[(3-hydroxytetradecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy][(2R)-2-[(3-hydroxydodecanoyl)oxy]-3-[(3-hydroxytetradecanoyl)oxy]propoxy]phosphinic acid
Traditional IUPAC Name: 2-hydroxy-3-{[hydroxy((2R)-2-[(3-hydroxydodecanoyl)oxy]-3-[(3-hydroxytetradecanoyl)oxy]propoxy)phosphoryl]oxy}propoxy((2R)-2-[(3-hydroxydodecanoyl)oxy]-3-[(3-hydroxytetradecanoyl)oxy]propoxy)phosphinic acid
SMILES:CCCCCCCCCCCC(O)CC(=O)OC[C@H](COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@H](COC(=O)CC(O)CCCCCCCCCCC)OC(=O)CC(O)CCCCCCCCC)OC(=O)CC(O)CCCCCCCCC
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-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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphoglycerophosphoglycerols
Direct Parent Cardiolipins
Alternative Parents
Substituents
  • Cardiolipin
  • Tetracarboxylic acid or derivatives
  • Beta-hydroxy acid
  • Fatty acid ester
  • Dialkyl phosphate
  • Fatty acyl
  • Hydroxy acid
  • Organic phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00142 mg/mLALOGPS
logP6.02ALOGPS
logP13.46ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)1.59ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area317.87 Å2ChemAxon
Rotatable Bond Count66ChemAxon
Refractivity320.95 m3·mol-1ChemAxon
Polarizability143.93 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
2 PG(14:0(3-OH)/12:0(3-OH)) > CL(14:0(3-OH)/12:0(3-OH)/14:0(3-OH)/12:0(3-OH)) + Glycerol
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-3290101000-9ef80cbdd89a52c0a113View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-5490223301-1218e74f36f6bfb10130View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7k-3651915100-c44e6637fcbea9331394View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004j-3190000000-5147b0ef8357cbda06e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-6390030200-ff52dfee11cdcfc10418View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9280040000-6ed41f6c10a43a87d498View 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