CL(17:0cycw7c/16:0/17:0cycw7c/18:1(9Z)) (PAMDB003366)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB003366
Identification
Name: CL(17:0cycw7c/16:0/17:0cycw7c/18:1(9Z))
Description:CL(17:0cycw7c/16:0/17:0cycw7c/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(17:0cycw7c/16:0/17:0cycw7c/18:1(9Z)) contains two chains of (heptadec-9-10-cyclo-anoyl) at the C1 and C3 positions, one chain of hexadecanoic acid at the C2 position, one chain of (9Z-octadecenoyl) at the C4 position. 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
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🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1'-[1-(heptadec-9-10-cyclo-anoyl),2-hexadecanoyl-sn-glycero-3-phospho],3'-[1-(heptadec-9-10-cyclo-anoyl),2-(9Z-octadecenoyl)-sn-glycero-3-phospho]-sn-glycerol
  • 1'-[1-heptadec-9-10-cyclo-anoyl-2-hexadecanoyl-sn-glycero-3-phospho],3'-[1,2-diheptadec-9-10-cyclo-anoyl-rac-glycero-3-phospho]-glycerol
  • 1'-[1-heptadec-9-10-cyclo-anoyl-2-palmitoyl-sn-glycero-3-phospho],3'-[1,2-diheptadec-9-10-cyclo-anoyl-rac-glycero-3-phospho]-glycerol
  • Cardiolipin(17:0/16:0/17:0/17:0)
  • Cardiolipin(67:0)
  • CL(1'-[17:0cycw7c/16:0],3'-[17:0cycw7c/17:0cycw7c])
  • CL(17:0/16:0/17:0/17:0)
  • CL(67:0)
Chemical Formula: C77H144O17P2
Average Molecular Weight: 1403.93
Monoisotopic Molecular Weight: 1402.987877173
InChI Key: LWGSZJVVTUZQHG-LDEMJFSTSA-N
InChI:InChI=1S/C77H144O17P2/c1-5-9-13-17-19-21-23-25-26-28-30-32-34-40-50-58-77(82)94-73(64-88-75(80)56-48-42-36-38-46-54-70-60-68(70)52-44-16-12-8-4)66-92-96(85,86)90-62-71(78)61-89-95(83,84)91-65-72(93-76(81)57-49-39-33-31-29-27-24-22-20-18-14-10-6-2)63-87-74(79)55-47-41-35-37-45-53-69-59-67(69)51-43-15-11-7-3/h25-26,67-73,78H,5-24,27-66H2,1-4H3,(H,83,84)(H,85,86)/b26-25-/t67?,68?,69?,70?,71-,72+,73+/m0/s1
CAS number: Not Available
IUPAC Name:[(2R)-2-(hexadecanoyloxy)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy][(2S)-3-({[(2R)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-2-[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name: (2R)-2-(hexadecanoyloxy)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy((2S)-3-{[(2R)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-2-[(9Z)-octadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
SMILES:[H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
Chemical Taxonomy
Taxonomy DescriptionNot Available
Kingdom Not Available
Super ClassNot Available
Class Not Available
Sub ClassNot Available
Direct Parent Not Available
Alternative Parents Not Available
Substituents Not Available
Molecular Framework Not Available
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.31e-05 mg/mLALOGPS
logP8.95ALOGPS
logP23.57ChemAxon
logS-7.5ALOGPS
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 Count77ChemAxon
Refractivity385.81 m3·mol-1ChemAxon
Polarizability167.21 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
PE(17:0cycw7c/17:0cycw7c) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(17:0cycw7c/16:0/17:0cycw7c/18:1(9Z))
Pathways:
Spectra
Spectra:
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