P. aeruginosa Metabolome Database: PGP(18:0/18:0) (PAMDB001680)

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

PAMDB001680

Identification

Name:

PGP(18:0/18:0)

Description:

PGP(18:0/18:0) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(18:0/18:0), in particular, consists of two octadecanoyl chains at positions C-1 and C-2. In Pseudomonas aeruginosa, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

1,2-dioctadecanoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
1,2-Dioctadecanoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphoric acid)
1,2-distearoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
1,2-Distearoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphoric acid)
3-sn-Phosphatidyl-1'-sn-glycerol 3'-phosphate
3-Sn-phosphatidyl-1'-sn-glycerol 3'-phosphorate
3-Sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid
PGP(36:0)

Chemical Formula:

C₄₂H₈₄O₁₃P₂

Average Molecular Weight:

859.069

Monoisotopic Molecular Weight:

858.538716761

InChI Key:

UZNYMWWMHBZMLI-XRSDMRJBSA-N

InChI:

InChI=1S/C42H84O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(44)51-37-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)55-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h39-40,43H,3-38H2,1-2H3,(H,49,50)(H2,46,47,48)/t39-,40-/m1/s1

CAS number:

Not Available

IUPAC Name:

[(2R)-3-({[(2R)-2,3-bis(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

Traditional IUPAC Name:

(2R)-3-{[(2R)-2,3-bis(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

SMILES:

[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC

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:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.000488 mg/mL	ALOGPS
logP	7.47	ALOGPS
logP	12.59	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	1.35	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	195.35 Å²	ChemAxon
Rotatable Bond Count	46	ChemAxon
Refractivity	224.59 m³·mol^-1	ChemAxon
Polarizability	101.8 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:

Water + PGP(18:0/18:0) > PG(18:0/18:0) + Phosphate
Adenosine triphosphate + Water + PGP(18:0/18:0) > ADP + Hydrogen ion + Phosphate + PGP(18:0/18:0)
Adenosine triphosphate + Water + PGP(18:0/18:0) > ADP + Hydrogen ion + Phosphate + PGP(18:0/18:0)
CDP-1,2-Dioctadecanoylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(18:0/18:0)
Glycerol 3-phosphate + CDP-1,2-Dioctadecanoylglycerol > Hydrogen ion + Cytidine monophosphate + PGP(18:0/18:0) + Cytidine monophosphate
PGP(18:0/18:0) + Water > Phosphate + PG(18:0/18:0) + PG(18:0/18:0)
PGP(18:0/18:0) + Water > PG(16:1(9Z)/18:1(9Z)) + Phosphate
PGP(18:0/18:0) + Water > PG(16:1(9Z)/19:iso) + Phosphate
PGP(18:0/18:0) + Water > PE(16:1(9Z)/18:1(9Z)) + Phosphate

Pathways:

Not Available

Spectra

Spectra:

References

References:

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	HMDB13504
Pubchem Compound ID	Not Available
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

• CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase

General function:: Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:: This protein catalyzes the committed step to the synthesis of the acidic phospholipids
Gene Name:: pgsA
Locus Tag:: PA2584
Molecular weight:: 20.5 kDa

Reactions

CDP-diacylglycerol + sn-glycerol 3-phosphate = CMP + 3(3-sn-phosphatidyl)-sn-glycerol 1-phosphate.

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

• Lipid A export ATP-binding/permease protein msbA

General function:: Involved in nucleotide binding
Specific function:: Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
Gene Name:: msbA
Locus Tag:: PA4997
Molecular weight:: 66.4 kDa

Transporters

Protein Details

• Lipid A export ATP-binding/permease protein msbA

General function:: Involved in nucleotide binding
Specific function:: Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
Gene Name:: msbA
Locus Tag:: PA4997
Molecular weight:: 66.4 kDa

PGP(18:0/18:0) (PAMDB001680)

Structure for PGP(18:0/18:0) (PAMDB001680)

Enzymes

Reactions

Reactions

Transporters