CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z)) (PAMDB000801)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000801
Identification
Name: CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))
Description:CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(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(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z)) contains four chains of (9Z-octadecenoyl) at the C1, C2, 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 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'-[1,2-di(9Z-octadecenoyl)-rac-glycero-3-phospho],3'-[1,2-di(9Z-octadecenoyl)-rac-glycero-3-phospho]-glycerol
  • 1'-[1,2-Dioleoyl-rac-glycero-3-phospho],3'-[1,2-dioleoyl-rac-glycero-3-phospho]-glycerol
  • Cardiolipin(18:1/18:1/18:1/18:1)
  • Cardiolipin(18:1n9/18:1n9/18:1n9/18:1n9)
  • Cardiolipin(18:1w9/18:1w9/18:1w9/18:1w9)
  • Cardiolipin(72:4)
  • Cardiolipins(18:1/18:1/18:1/18:1)
  • Cardiolipins(18:1n9/18:1n9/18:1n9/18:1n9)
  • Cardiolipins(18:1w9/18:1w9/18:1w9/18:1w9)
  • Cardiolipins(72:4)
  • CL(1'-[18:1(9Z)/18:1(9Z)],3'-[18:1(9Z)/18:1(9Z)])
  • CL(18:1/18:1/18:1/18:1)
  • CL(18:1n9/18:1n9/18:1n9/18:1n9)
  • CL(18:1w9/18:1w9/18:1w9/18:1w9)
  • CL(72:4)
  • Diphosphatidylglycerol
Chemical Formula: C81H150O17P2
Average Molecular Weight: 1457.995
Monoisotopic Molecular Weight: 1457.034826398
InChI Key: TWHQNHQPSCPQNY-WVRHUKEESA-N
InChI:InChI=1S/C81H150O17P2/c1-5-9-13-17-21-25-29-33-37-41-45-49-53-57-61-65-78(83)91-71-76(97-80(85)67-63-59-55-51-47-43-39-35-31-27-23-19-15-11-7-3)73-95-99(87,88)93-69-75(82)70-94-100(89,90)96-74-77(98-81(86)68-64-60-56-52-48-44-40-36-32-28-24-20-16-12-8-4)72-92-79(84)66-62-58-54-50-46-42-38-34-30-26-22-18-14-10-6-2/h33-40,75-77,82H,5-32,41-74H2,1-4H3,(H,87,88)(H,89,90)/b37-33-,38-34-,39-35-,40-36-/t76-,77-/m1/s1
CAS number: Not Available
IUPAC Name:[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy][3-({[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name: tetraoleoyl cardiolipin
SMILES:CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)OCC(O)([H])COP(=O)(O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
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
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility7.26e-05 mg/mLALOGPS
logP9.1ALOGPS
logP25.82ChemAxon
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 Å2ChemAxon
Rotatable Bond Count82ChemAxon
Refractivity411.38 m3·mol-1ChemAxon
Polarizability176.84 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
2 PG(18:1(9Z)/18:1(9Z)) > Glycerol + CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-054o-0941803430-f4ae1ac6a0ec1fd9c7c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0953505460-2590532b3ee63b0ead8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9f-0469628750-7c0b320a41fc76fac139View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06si-0490301010-24fc34d91f0a6362aa53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3190101010-be8e3afad2cd40720696View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005a-9060003010-7e73197f4a25d2f6b554View 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 ID60356
HMDB IDHMDB10691
Pubchem Compound ID46931152
Kegg IDC05980
ChemSpider ID21403061
Wikipedia IDNot Available
BioCyc IDCARDIOLIPIN
EcoCyc IDCARDIOLIPIN

Enzymes

Protein Details
• Cardiolipin synthase
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes the reversible phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Affects resistance to the gyrase inhibitor novobiocin
Gene Name:
cls
Locus Tag:
PA5394
Molecular weight:
54.6 kDa
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.
Protein Details
• Putative cardiolipin synthase ybhO
General function:
Involved in catalytic activity
Specific function:
Catalyzes, in vitro, the phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Can also catalyze phosphatidyl group transfer to water to form phosphatidate. Catalyzes little, if any, cardiolipin synthesis in vivo, even when the expression level is very high
Gene Name:
ybhO
Locus Tag:
PA2155
Molecular weight:
46.5 kDa
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.

Transporters

Protein Details
• Probable phospholipid ABC transporter permease protein mlaE
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaE
Locus Tag:
PA4455
Molecular weight:
28.4 kDa