CL(19:0cycv8c/15:0cyclo/19:0cycv8c/15:0cyclo) (PAMDB003342)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB003342
Identification
Name: CL(19:0cycv8c/15:0cyclo/19:0cycv8c/15:0cyclo)
Description:CL(19:0cycv8c/15:0cyclo/19:0cycv8c/15:0cyclo) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(19:0cycv8c/15:0cyclo/19:0cycv8c/15:0cyclo) contains two chains of (heptadec-11-12-cyclo-anoyl) at the C1 and C3 positions, two chains of cis-9,10-Methylenetetradecanoic 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-(Heptadec-11-12-cyclo-anoyl),2-cis-9,10-methylenetetradecanoate-sn-glycero-3-phospho],3'-[1-(heptadec-11-12-cyclo-anoyl),2-cis-9,10-methylenetetradecanoate-sn-glycero-3-phospho]-sn-glycerol
  • 1'-[1-(heptadec-11-12-cyclo-anoyl),2-cis-9,10-Methylenetetradecanoic acid-sn-glycero-3-phospho],3'-[1-(heptadec-11-12-cyclo-anoyl),2-cis-9,10-Methylenetetradecanoic acid-sn-glycero-3-phospho]-sn-glycerol
  • 1'-[1-(heptadec-11-12-cyclo-anoyl)-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phospho],3'-[1,2-di(heptadec-11-12-cyclo-anoyl)-rac-glycero-3-phospho]-glycerol
  • 1'-[1-(heptadec-11-12-cyclo-anoyl)-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phospho],3'-[1,2-di(heptadec-11-12-cyclo-anoyl)-rac-glycero-3-phospho]-glycerol
  • 1'-[1-heptadec-11-12-cyclo-anoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phospho],3'-[1,2-diheptadec-11-12-cyclo-anoyl-rac-glycero-3-phospho]-glycerol
  • Cardiolipin(19:0/15:0/19:0/19:0)
  • Cardiolipin(72:0)
  • CL(1'-[19:0cycv8c/15:0cyclo],3'-[19:0cycv8c/19:0cycv8c])
  • CL(19:0/15:0/19:0/19:0)
  • CL(72:0)
Chemical Formula: C77H142O17P2
Average Molecular Weight: 1401.8887
Monoisotopic Molecular Weight: 1400.972226142
InChI Key: GZWKGZHTKWOUPQ-PZOLKUBDSA-N
InChI:InChI=1S/C77H142O17P2/c1-5-9-13-31-43-67-55-69(67)47-33-23-17-15-19-27-37-49-74(79)87-59-72(93-76(81)51-39-29-21-25-35-45-65-53-63(65)41-11-7-3)61-91-95(83,84)89-57-71(78)58-90-96(85,86)92-62-73(94-77(82)52-40-30-22-26-36-46-66-54-64(66)42-12-8-4)60-88-75(80)50-38-28-20-16-18-24-34-48-70-56-68(70)44-32-14-10-6-2/h63-73,78H,5-62H2,1-4H3,(H,83,84)(H,85,86)/t63?,64?,65?,66?,67?,68?,69?,70?,71?,72-,73-/m1/s1
CAS number: Not Available
IUPAC Name:[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy][3-({[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name: (2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy(3-{[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
SMILES:CCCCCCC1CC1CCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@H](COC(=O)CCCCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCC1CC1CCCC)OC(=O)CCCCCCCC1CC1CCCC
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 homomonocyclic compound
Molecular Framework Aliphatic homomonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.74e-05 mg/mLALOGPS
logP8.55ALOGPS
logP22.38ChemAxon
logS-7.7ALOGPS
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
Refractivity380.88 m3·mol-1ChemAxon
Polarizability166.96 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
PE(15:0/19:iso) + PG(15:0/19:iso) > CL(19:0cycv8c/15:0cyclo/19:0cycv8c/15:0cyclo) + Ethanolamine
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0794321220-81874bfa728a93622ab9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00b9-0895013150-44ea9542594d7cb849c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1786093330-37b9658c503edceff3a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-0292000000-7893986016b00f6f3167View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-2191001010-098c38d502bd5ae5b22bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-8090003000-658b272ace60c3e50202View in MoNA
References
References:
  • 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
  • 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