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Record Information
Version	2.0
Creation Date	2015-09-08 19:03:02 -0600
Update Date	2015-09-16 17:35:11 -0600
Secondary Accession Numbers	ECMDB24354
Identification
Name:	CL(12:0/12:0/12:0/12:0)
Description	CL(12:0/12:0/12:0/12:0) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(12:0/12:0/12:0/12:0) contains four chains of dodecanoic acid 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 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:0xa75cc900> Close
Synonyms:	Not Available
Chemical Formula:	C57H110O17P2
Weight:	Average: 1129.4206 Monoisotopic: 1128.721825118
InChI Key:	LNSKUBQTAKEJOP-TVALRIBFSA-N
InChI:	InChI=1S/C57H110O17P2/c1-5-9-13-17-21-25-29-33-37-41-54(59)67-47-52(73-56(61)43-39-35-31-27-23-19-15-11-7-3)49-71-75(63,64)69-45-51(58)46-70-76(65,66)72-50-53(74-57(62)44-40-36-32-28-24-20-16-12-8-4)48-68-55(60)42-38-34-30-26-22-18-14-10-6-2/h51-53,58H,5-50H2,1-4H3,(H,63,64)(H,65,66)/t52-,53-/m1/s1
CAS number:	Not Available
IUPAC Name:	[(2R)-2,3-bis(dodecanoyloxy)propoxy][3-({[(2R)-2,3-bis(dodecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name:	(2R)-2,3-bis(dodecanoyloxy)propoxy(3-{[(2R)-2,3-bis(dodecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
SMILES:	CCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@H](COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCC
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 Secondary alcohols Carboxylic acid esters Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 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 0.00051 g/L ALOGPS logP 7.85 ALOGPS logP 16.6 ChemAxon logS -6.3 ALOGPS pKa (Strongest Acidic) 1.59 ChemAxon pKa (Strongest Basic) -3.4 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 9 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 236.95 Ų ChemAxon Rotatable Bond Count 62 ChemAxon Refractivity 296.49 m³·mol⁻¹ ChemAxon Polarizability 129.46 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:
SMPDB Pathways:	Not Available
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, Negative splash10-0032-0900010003-b5be646abe30232d1a80 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-002k-3901021001-b3513bc6365c44536451 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004j-9421040000-10a87b30dc451f885d70 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-0100090000-916be6566025354815cf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-03di-0101190000-7b85a170f367e917ce83 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-000b-0907110000-e7660ce077e91b82b24a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0059-0910231106-0b3e757d9501f3151988 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-01s6-0920463105-5a10fb6cd08495625bdb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000f-2670971000-83dc5513b375ce3ef1cb 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 HMDB0201179 Pubchem Compound ID 102383108 Kegg ID Not Available ChemSpider ID 59695819 Wikipedia ID Not Available BioCyc ID Not Available