P. aeruginosa Metabolome Database: CL(12:0(3-OH)/10:0(3-OH)/12:0(3-OH)/10:0(3-OH)) (PAMDB006966)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB006966

Identification

Name:

CL(12:0(3-OH)/10:0(3-OH)/12:0(3-OH)/10:0(3-OH))

Description:

CL(12:0(3-OH)/10:0(3-OH)/12:0(3-OH)/10:0(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(12:0(3-OH)/10:0(3-OH)/12:0(3-OH)/10:0(3-OH)) contains two chains of 3-hydroxydodecanoic acid at the C1 and C3 positions, two chains of 3-hydroxydecanoic 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

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

Not Available

Chemical Formula:

C₅₃H₁₀₂O₂₁P₂

Average Molecular Weight:

1137.326

Monoisotopic Molecular Weight:

1136.6388843

InChI Key:

YVBKEXYNWWYDAM-UKFWLGQFSA-N

InChI:

InChI=1S/C53H102O21P2/c1-5-9-13-17-19-23-27-29-43(54)33-50(59)67-39-48(73-52(61)35-45(56)31-25-21-15-11-7-3)41-71-75(63,64)69-37-47(58)38-70-76(65,66)72-42-49(74-53(62)36-46(57)32-26-22-16-12-8-4)40-68-51(60)34-44(55)30-28-24-20-18-14-10-6-2/h43-49,54-58H,5-42H2,1-4H3,(H,63,64)(H,65,66)/t43?,44?,45?,46?,47?,48-,49-/m1/s1

CAS number:

Not Available

IUPAC Name:

[2-hydroxy-3-({hydroxy[(2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy][(2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphinic acid

Traditional IUPAC Name:

2-hydroxy-3-{[hydroxy((2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy)phosphoryl]oxy}propoxy((2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy)phosphinic acid

SMILES:

CCCCCCCCCC(O)CC(=O)OC[C@H](COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@H](COC(=O)CC(O)CCCCCCCCC)OC(=O)CC(O)CCCCCCC)OC(=O)CC(O)CCCCCCC

Chemical Taxonomy

Taxonomy Description

This 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-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

Substituents

Cardiolipin
Tetracarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Dialkyl phosphate
Fatty acyl
Hydroxy acid
Organic phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
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	0.00539 mg/mL	ALOGPS
logP	4.85	ALOGPS
logP	9.9	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	1.59	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	317.87 Å²	ChemAxon
Rotatable Bond Count	58	ChemAxon
Refractivity	284.14 m³·mol^-1	ChemAxon
Polarizability	125.74 Å³	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(12:0(3-OH)/10:0(3-OH)) > Glycerol + CL(12:0(3-OH)/10:0(3-OH)/12:0(3-OH)/10:0(3-OH))

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gba-0900010003-4a377c3104c0587825da	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0v4j-0900132005-0677a1539a5ef0c69f38	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-1930751003-7685ab1dfa0ff063e443	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014s-0910010003-57c08c69a42c31ef470b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00mk-3930032003-b339b9465bc1c67eea5b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9450030000-b50ce605a42065e2312a	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

CL(12:0(3-OH)/10:0(3-OH)/12:0(3-OH)/10:0(3-OH)) (PAMDB006966)

Structure for CL(12:0(3-OH)/10:0(3-OH)/12:0(3-OH)/10:0(3-OH)) (PAMDB006966)