P. aeruginosa Metabolome Database: CL(15:0cyclo/19:0cycv8c/16:1(9Z)/16:1(9Z)) (PAMDB002259)

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

PAMDB002259

Identification

Name:

CL(15:0cyclo/19:0cycv8c/16:1(9Z)/16:1(9Z))

Description:

CL(15:0cyclo/19:0cycv8c/16:1(9Z)/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(15:0cyclo/19:0cycv8c/16:1(9Z)/16:1(9Z)) contains one chain of cis-9,10-Methylenetetradecanoic acid at the C1 position, one chain of (heptadec-11-12-cyclo-anoyl) at the C2 position, two chains of (9Z-hexadecenoyl) at the 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 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:

1'-[1-(cis-9,10-Methylenetetradecanoyl)-2-(heptadec-11-12-cyclo-anoyl)-sn-glycero-3-phospho],3'-[1,2-di(9Z-hexadecenoyl)-rac-glycero-3-phospho]-glycerol
1'-[1-(cis-9,10-Methylenetetradecanoyl)-2-(heptadec-11-12-cyclo-anoyl)-sn-glycero-3-phospho],3'-[1,2-dipalmitoleoyl-rac-glycero-3-phospho]-glycerol
1'-[1-(cis-9,10-Methylenetetradecanoyl)-2-heptadec-11-12-cyclo-anoyl-sn-glycero-3-phospho],3'-[1,2-di(9Z-hexadecenoyl)-rac-glycero-3-phospho]-glycerol
1'-[1-(cis-9,10-Methylenetetradecanoyl)-2-heptadec-11-12-cyclo-anoyl-sn-glycero-3-phospho],3'-[1,2-dipalmitoleoyl-rac-glycero-3-phospho]-glycerol
Cardiolipin(15:0/19:0/16:1/16:1)
Cardiolipin(66:2)
CL(1'-[15:0cyclo/19:0cycv8c],3'-[16:1(9Z)/16:1(9Z)])
CL(15:0/19:0/16:1/16:1)
CL(66:2)

Chemical Formula:

C₇₅H₁₃₈O₁₇P₂

Average Molecular Weight:

1373.86

Monoisotopic Molecular Weight:

1372.94092698

InChI Key:

SVUHUZJYTSAKCJ-DIRSQVBQSA-N

InChI:

InChI=1S/C75H138O17P2/c1-5-9-13-16-18-20-22-24-26-28-32-38-45-53-72(77)85-61-70(91-74(79)55-47-39-33-29-27-25-23-21-19-17-14-10-6-2)63-89-93(81,82)87-59-69(76)60-88-94(83,84)90-64-71(62-86-73(78)54-46-41-35-37-44-51-66-57-65(66)49-12-8-4)92-75(80)56-48-40-34-30-31-36-43-52-68-58-67(68)50-42-15-11-7-3/h20-23,65-71,76H,5-19,24-64H2,1-4H3,(H,81,82)(H,83,84)/b22-20-,23-21-/t65?,66?,67?,68?,69-,70-,71-/m1/s1

CAS number:

Not Available

IUPAC Name:

[(2S)-3-({[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy]phosphinic acid

Traditional IUPAC Name:

(2S)-3-{[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy)phosphinic acid

SMILES:

[H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CCCCCCCCCC1CC1CCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC

Chemical Taxonomy

Taxonomy Description

Not Available

Kingdom

Not Available

Super Class

Not Available

Class

Not Available

Sub Class

Not 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:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	4.96e-05 mg/mL	ALOGPS
logP	8.91	ALOGPS
logP	22.32	ChemAxon
logS	-7.4	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 Å²	ChemAxon
Rotatable Bond Count	74	ChemAxon
Refractivity	377.72 m³·mol^-1	ChemAxon
Polarizability	162.31 Å³	ChemAxon
Number of Rings	2	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:

PG(16:1(9Z)/16:1(9Z)) + PE(15:0/19:iso) > Ethanolamine + CL(15:0cyclo/19:0cycv8c/16:1(9Z)/16:1(9Z))

Pathways:

Glycerophospholipid metabolism pae00564

Spectra

Spectra:

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

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(15:0cyclo/19:0cycv8c/16:1(9Z)/16:1(9Z)) (PAMDB002259)

Structure for CL(15:0cyclo/19:0cycv8c/16:1(9Z)/16:1(9Z)) (PAMDB002259)