Record Information
Version2.0
Creation Date2012-08-23 12:31:34 -0600
Update Date2015-12-09 10:13:15 -0700
Secondary Accession Numbers
  • ECMDB22320
Identification
Name:CL(16:1(9Z)/16:0/17:0cycw7c/16:1(9Z))
DescriptionCL(16:1(9Z)/16:0/17:0cycw7c/16:1(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(16:1(9Z)/16:0/17:0cycw7c/16:1(9Z)) contains two chains of (9Z-hexadecenoyl) at the C1 and C4 positions, one chain of hexadecanoic acid at the C2 position, one chain of (heptadec-9-10-cyclo-anoyl) at the C3 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 E. coli, 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 E. coli, 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. E. coli 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 E. coli and other rod-shaped bacteria. It is known that the polar positioning of the proline transporter ProP and the mechanosensitive ion channel MscS in E. coli 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
Synonyms:
  • 1'-[1-(9Z-hexadecenoyl)-2-hexadecanoyl-sn-glycero-3-phospho],3'-[1,2-diheptadec-9-10-cyclo-anoyl-rac-glycero-3-phospho]-glycerol
  • 1'-[1-palmitoleoyl-2-palmitoyl-sn-glycero-3-phospho],3'-[1,2-diheptadec-9-10-cyclo-anoyl-rac-glycero-3-phospho]-glycerol
  • Cardiolipin(16:1/16:0/17:0/17:0)
  • Cardiolipin(66:1)
  • CL(1'-[16:1(9Z)/16:0],3'-[17:0cycw7c/17:0cycw7c])
  • CL(16:1/16:0/17:0/17:0)
  • CL(66:1)
Chemical Formula:C74H138O17P2
Weight:Average: 1361.849
Monoisotopic: 1360.94092698
InChI Key:NUJFBAKDGKBLKS-ADIWMGJOSA-N
InChI:InChI=1S/C74H138O17P2/c1-5-9-13-17-20-23-26-29-32-35-38-43-49-55-71(76)84-62-69(90-73(78)57-51-44-39-36-33-30-27-24-21-18-14-10-6-2)64-88-92(80,81)86-60-68(75)61-87-93(82,83)89-65-70(91-74(79)58-52-45-40-37-34-31-28-25-22-19-15-11-7-3)63-85-72(77)56-50-46-41-42-48-54-67-59-66(67)53-47-16-12-8-4/h23,25-26,28,66-70,75H,5-22,24,27,29-65H2,1-4H3,(H,80,81)(H,82,83)/b26-23-,28-25-/t66?,67?,68-,69+,70+/m0/s1
CAS number:Not Available
IUPAC Name:[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-(hexadecanoyloxy)propoxy][(2S)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name:(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-(hexadecanoyloxy)propoxy((2S)-3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
SMILES:[H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerophosphoglycerols
Direct ParentCardiolipins
Alternative Parents
Substituents
  • Cardiolipin
  • Tetracarboxylic acid or derivatives
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.4e-05 g/LALOGPS
logP8.88ALOGPS
logP22.66ChemAxon
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 ŲChemAxon
Rotatable Bond Count75ChemAxon
Refractivity375.03 m³·mol⁻¹ChemAxon
Polarizability163.2 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
phospholipid biosynthesis CL(16:1(9Z)/16:0/17:0cycw7c/16:1(9Z))PW001496 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
0.03779± 0.0 uMK12Luria-Bertani (LB) mediaStationary phase cultures (overnight culture)Shake flask37 oCPMID: 22956318
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pbl-1986041330-daf2fd34b2de0e642f15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9l-0693032220-74c91af7e7ebf6f86f30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rb-1294073300-03c3248933b3924a0687View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-100a-0291000000-186e762c2cf2139048efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fvj-3091001000-46cbd7f1ffc096d3dc1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9080003000-7cf6a71d233aed1b873aView 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
  • 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

Enzymes

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
Uniprot ID:
P0A6H8
Molecular weight:
54822
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.
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
Uniprot ID:
P0AA84
Molecular weight:
47633
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.
General function:
cardiolipin biosynthetic process
Specific function:
Catalyzes the synthesis of cardiolipin (CL) (diphosphatidylglycerol) from phosphatidylglycerol (PG) and phosphatidylethanolamine (PE).
Gene Name:
clsC
Uniprot ID:
P75919
Molecular weight:
53665
Reactions
Phosphatidylglycerol + phosphatidylethanolamine = diphosphatidylglycerol + ethanolamine