P. aeruginosa Metabolome Database: PG(12:0/19:iso) (PAMDB004056)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB004056

Identification

Name:

PG(12:0/19:iso)

Description:

PG(12:0/19:iso) 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(12:0/19:iso), in particular, consists of one dodecanoyl chain to the C-1 atom, and one 17-methylocatdecanoyl 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-dodecanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phospho-(1'-glycerol)
1-dodecanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerol
1-dodecanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerol
GPG(12:0/19:0)
GPG(31:0)
PG(12:0/19:0)
PG(31:0)
Phosphatidylglycerol(12:0/19:0)
Phosphatidylglycerol(31:0)

Chemical Formula:

C₃₇H₇₃O₁₀P

Average Molecular Weight:

708.9433

Monoisotopic Molecular Weight:

708.494135068

InChI Key:

YXTUZYZYVPKQMY-UHFFFAOYSA-N

InChI:

InChI=1S/C37H73O10P/c1-4-5-6-7-8-14-18-21-24-27-36(40)44-31-35(32-46-48(42,43)45-30-34(39)29-38)47-37(41)28-25-22-19-16-13-11-9-10-12-15-17-20-23-26-33(2)3/h33-35,38-39H,4-32H2,1-3H3,(H,42,43)

CAS number:

Not Available

IUPAC Name:

(2,3-dihydroxypropoxy)[3-(dodecanoyloxy)-2-[(17-methyloctadecanoyl)oxy]propoxy]phosphinic acid

Traditional IUPAC Name:

2,3-dihydroxypropoxy(3-(dodecanoyloxy)-2-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acid

SMILES:

CCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCC(C)C

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerols

Direct Parent

Phosphatidylglycerols

Alternative Parents

Substituents

1,2-diacylglycerophosphoglycerol
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Fatty acyl
Alkyl phosphate
Organic phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Primary alcohol
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.000169 mg/mL	ALOGPS
logP	7.35	ALOGPS
logP	10.33	ChemAxon
logS	-6.6	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	38	ChemAxon
Refractivity	190.66 m³·mol^-1	ChemAxon
Polarizability	85.9 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 PGP(12:0/19:iso) + Water >2 PG(12:0/19:iso) + Phosphate
2 PG(12:0/19:iso) > Glycerol + CL(12:0/19:iso/12:0/19:iso)

Pathways:

Glycerophospholipid metabolism pae00564

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-053u-5690445300-55b48fb97d902e111a90	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0043-8891333000-b2a0232c89ddadaec903	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9451010000-98178348ddd7670dc795	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0532-0930202200-edbc74e38205335be2ec	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0032-4910101000-663f5c8fabf26c69fbde	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9210000000-dd1f7248cef3f612d1a3	View in MoNA

References

References:

Casadei MA, Ma?as P, Niven G, Needs E, Mackey BM. (2002) "Role of membrane fluidity in pressure resistance of Escherichia coli NCTC 8164." Appl Environ Microbiol. 68(12):5965-72. Pubmed: 12450817
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
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

• Lysophospholipase L2

General function:: Lipid transport and metabolism
Specific function:: 2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:: pldB
Locus Tag:: PA5089
Molecular weight:: 83.4 kDa

Reactions

2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.

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

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

• 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

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(12:0/19:iso) (PAMDB004056)

Structure for PG(12:0/19:iso) (PAMDB004056)

Enzymes

Reactions

Reactions

Reactions

Reactions

Transporters