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Record Information
Version	2.0
Creation Date	2015-09-08 20:23:45 -0600
Update Date	2015-09-16 17:35:12 -0600
Secondary Accession Numbers	ECMDB24876
Identification
Name:	CL(14:0/12:0(3-OH)/14:0/12:0(3-OH))
Description	CL(14:0/12:0(3-OH)/14:0/12:0(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(14:0/12:0(3-OH)/14:0/12:0(3-OH)) contains two chains of tetradecanoic 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 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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa668cbac> Close
Synonyms:	Not Available
Chemical Formula:	C61H118O19P2
Weight:	Average: 1217.544 Monoisotopic: 1216.774255576
InChI Key:	BAFZFUAOWYGMFG-IGRRIJAJSA-N
InChI:	InChI=1S/C61H118O19P2/c1-5-9-13-17-21-23-25-27-31-35-39-43-58(65)73-49-56(79-60(67)45-53(62)41-37-33-29-19-15-11-7-3)51-77-81(69,70)75-47-55(64)48-76-82(71,72)78-52-57(80-61(68)46-54(63)42-38-34-30-20-16-12-8-4)50-74-59(66)44-40-36-32-28-26-24-22-18-14-10-6-2/h53-57,62-64H,5-52H2,1-4H3,(H,69,70)(H,71,72)/t53?,54?,55?,56-,57-/m1/s1
CAS number:	Not Available
IUPAC Name:	[2-hydroxy-3-({hydroxy[(2R)-2-[(3-hydroxydodecanoyl)oxy]-3-(tetradecanoyloxy)propoxy]phosphoryl}oxy)propoxy][(2R)-2-[(3-hydroxydodecanoyl)oxy]-3-(tetradecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name:	2-hydroxy-3-{[hydroxy((2R)-2-[(3-hydroxydodecanoyl)oxy]-3-(tetradecanoyloxy)propoxy)phosphoryl]oxy}propoxy((2R)-2-[(3-hydroxydodecanoyl)oxy]-3-(tetradecanoyloxy)propoxy)phosphinic acid
SMILES:	CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@H](COC(=O)CCCCCCCCCCCCC)OC(=O)CC(O)CCCCCCCCC)OC(=O)CC(O)CCCCCCCCC
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.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Glycerophospholipids
Sub Class	Glycerophosphoglycerophosphoglycerols
Direct Parent	Cardiolipins
Alternative Parents	Tetracarboxylic acids and derivatives Fatty acid esters Dialkyl phosphates Beta hydroxy acids and derivatives Secondary alcohols Carboxylic acid esters Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Cardiolipin Tetracarboxylic acid or derivatives Dialkyl phosphate Fatty acid ester Beta-hydroxy acid Fatty acyl Alkyl phosphate Phosphoric acid ester Organic phosphoric acid derivative Hydroxy acid Secondary alcohol Carboxylic acid ester Carboxylic acid derivative Organic oxygen compound Organic oxide Hydrocarbon derivative Organooxygen compound Carbonyl group Alcohol 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:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.00039 g/L ALOGPS logP 7.05 ALOGPS logP 15.92 ChemAxon logS -6.5 ALOGPS pKa (Strongest Acidic) 1.59 ChemAxon pKa (Strongest Basic) -2.8 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 11 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 277.41 Ų ChemAxon Rotatable Bond Count 66 ChemAxon Refractivity 317.92 m³·mol⁻¹ ChemAxon Polarizability 140.5 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Membrane
Reactions:	2 PG(14:0/12:0(3-OH)) > Glycerol + CL(14:0/12:0(3-OH)/14:0/12:0(3-OH))
SMPDB Pathways:	phospholipid biosynthesis (CL(14:0/12:0(3-OH)/14:0/12:0(3-OH))) PW001943
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0002-2950101104-1ba093db343fddb7d588 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0gwb-3930122302-39ea9d94611865314dcc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0hh1-3960824100-97f96b4207370aeaac65 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0691-1290000102-fc4a8f82292e68333b4d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-4390030201-a17ae7a6aeb1ba9d0a20 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9180030000-5d2a22ba1faff7fca3dd View 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
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID Not Available Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

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