P. aeruginosa Metabolome Database: PG(19:0/17:0) (PAMDB001449)

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

PAMDB001449

Identification

Name:

PG(19:0/17:0)

Description:

PG(19:0/17:0) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(19:0/17:0), in particular, consists of one nonadecanoyl chain to the C-1 atom, and one heptadecanoyl to the C-2 atom. In Pseudomonas aeruginosa glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

1--2-heptadecanoyl-sn-glycero-3-phosphoglycerol
1-nonadecanoyl-2-heptadecanoyl-glycero-3-phospho-(1'-sn-glycerol)
1-nonadecanoyl-2-heptadecanoyl-sn-glycero-3-phosphoglycerol
1-nonadecanoyl-2-margaroyl-sn-glycero-3-phospho-(1'-glycerol)
1-nonadecanoyl-2-margaroyl-sn-glycero-3-phosphoglycerol
GPG(19:0/17:0)
GPG(36:0)
PG(36:0)
Phosphatidylglycerol(19:0/17:0)
Phosphatidylglycerol(36:0)

Chemical Formula:

C₄₂H₈₃O₁₀P

Average Molecular Weight:

779.09

Monoisotopic Molecular Weight:

778.572385871

InChI Key:

VRXBINAFDUHENA-XRSDMRJBSA-N

InChI:

InChI=1S/C42H83O10P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-42(46)52-40(38-51-53(47,48)50-36-39(44)35-43)37-49-41(45)33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h39-40,43-44H,3-38H2,1-2H3,(H,47,48)/t39-,40-/m1/s1

CAS number:

Not Available

IUPAC Name:

[(2R)-2,3-dihydroxypropoxy][(2R)-3-(heptadecanoyloxy)-2-(nonadecanoyloxy)propoxy]phosphinic acid

Traditional IUPAC Name:

(2R)-2,3-dihydroxypropoxy((2R)-3-(heptadecanoyloxy)-2-(nonadecanoyloxy)propoxy)phosphinic acid

SMILES:

[H][C@@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCC

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:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	7.31e-05 mg/mL	ALOGPS
logP	8.6	ALOGPS
logP	12.72	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	44	ChemAxon
Refractivity	213.71 m³·mol^-1	ChemAxon
Polarizability	95.85 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:

Pathways:

Glycerophospholipid metabolism pae00564

Spectra

Spectra:

References

References:

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

Enzymes

Protein Details

• Phosphatidylglycerophosphatase A

General function:: Involved in phosphatidylglycerophosphatase activity
Specific function:: One of the three phospholipid phosphatases, specifically hydrolyzes phosphatidylglycerophosphate
Gene Name:: pgpA
Locus Tag:: PA4050
Molecular weight:: 19.6 kDa

Reactions

Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate.

Protein Details

• Cardiolipin synthase

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
Locus Tag:: PA5394
Molecular weight:: 54.6 kDa

Reactions

2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.

Protein Details

• Putative cardiolipin synthase ybhO

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
Locus Tag:: PA2155
Molecular weight:: 46.5 kDa

Reactions

2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.

Transporters

Protein Details

• Probable phospholipid ABC transporter permease protein mlaE

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:: mlaE
Locus Tag:: PA4455
Molecular weight:: 28.4 kDa

PG(19:0/17:0) (PAMDB001449)

Structure for PG(19:0/17:0) (PAMDB001449)

Enzymes

Reactions

Reactions

Reactions

Transporters