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PGP(18:1(11Z)/18:1(11Z)) (M2MDB001681)

Record Information
Version2.0
Creation Date2012-07-30 14:55:10 -0600
Update Date2015-12-09 17:01:33 -0700
Secondary Accession Numbers
  • ECMDB21274
Identification
Name:PGP(18:1(11Z)/18:1(11Z))
DescriptionPGP(18:1(11Z)/18:1(11Z)) 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(18:1(11Z)/18:1(11Z)), in particular, consists of two 11Z-octadecenoyl chains at positions C-1 and C-2. In E. coli, 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 1,2-di(11Z-octadecenoyl)-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
  • 1,2-Di(11Z-octadecenoyl)-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphoric acid)
  • 1,2-divaccenoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
  • 1,2-Divaccenoyl-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(18:1/18:1)
  • PGP(18:1n7/18:1n7)
  • PGP(18:1w7/18:1w7)
  • PGP(36:2)
Chemical Formula:C42H80O13P2
Weight:Average: 855.037
Monoisotopic: 854.507416632
InChI Key:JUWFWNRVCXDDFB-ZAQZKMIBSA-N
InChI:InChI=1S/C42H80O13P2/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/h13-16,39-40,43H,3-12,17-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b15-13-,16-14-/t39-,40-/m1/s1
CAS number:Not Available
IUPAC Name:[(2R)-3-({[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name:(2R)-3-{[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
SMILES:[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerophosphates
Direct ParentPhosphatidylglycerophosphates
Alternative Parents
Substituents
  • Diacylglycerophosphoglycerophosphate
  • Sn-glycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0006 g/LALOGPS
logP7.47ALOGPS
logP11.87ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)1.35ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area195.35 ŲChemAxon
Rotatable Bond Count44ChemAxon
Refractivity226.82 m³·mol⁻¹ChemAxon
Polarizability98.22 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Water + PGP(18:1(11Z)/18:1(11Z)) > PG(18:1(11Z)/18:1(11Z)) + Phosphate
Adenosine triphosphate + Water + PGP(18:1(11Z)/18:1(11Z)) > ADP + Hydrogen ion + Phosphate + PGP(18:1(11Z)/18:1(11Z))
Adenosine triphosphate + Water + PGP(18:1(11Z)/18:1(11Z)) > ADP + Hydrogen ion + Phosphate + PGP(18:1(11Z)/18:1(11Z))
CDP-1,2-dioctadec-11-enoylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(18:1(11Z)/18:1(11Z))
2 CDP-DG(18:1(9Z)/18:1(11Z)) + Glycerol 3-phosphate >2 PGP(18:1(11Z)/18:1(11Z)) + Cytidine monophosphate + Hydrogen ion
2 PGP(18:1(11Z)/18:1(11Z)) + Water >2 PG(18:1(11Z)/18:1(11Z)) + Phosphate
2 PGP(18:1(11Z)/18:1(11Z)) + Water >2 PG(18:1(11Z)/18:1(9Z)) + Phosphate
2 PGP(18:1(11Z)/18:1(11Z)) + Water >2 PG(18:1(9Z)/18:1(11Z)) + Phosphate
SMPDB Pathways:
phospholipid biosynthesis (CL(18:1(11Z)/19:0/18:1(11Z)/19:0))PW001980 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0/18:1(11Z)/19:0/18:1(11Z)))PW001987 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0abi-1472282390-c6b21d8421d15baf4a57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0610-4594045230-5b383ac7aa3a5a5714f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9447233300-4265f5413fb36da3cd22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gz9-4090030030-f0bdc02fd63c67df60e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-8243ad8b758af20843e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8029f3a5e270c36c66c4View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB13520
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Phosphatidylglycerophosphatase B
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes phosphatidylglycerophosphate, phosphatidic acid, and lysophosphatidic acid; the pattern of activities varies according to subcellular location
Gene Name:
pgpB
Uniprot ID:
P0A924
Molecular weight:
29021
Reactions
Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate.
Protein Details
2. 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
Uniprot ID:
P0ABF8
Molecular weight:
20700
Reactions
CDP-diacylglycerol + sn-glycerol 3-phosphate = CMP + 3(3-sn-phosphatidyl)-sn-glycerol 1-phosphate.
Protein Details
3. Phosphatidylglycerophosphatase A
General function:
Involved in phosphatidylglycerophosphatase activity
Specific function:
One of the three phospholipid phosphatases, specifically hydrolyzes phosphatidylglycerophosphate
Gene Name:
pgpA
Uniprot ID:
P18200
Molecular weight:
19418
Reactions
Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate.
Protein Details
4. 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
Uniprot ID:
P60752
Molecular weight:
64460

Transporters

Protein Details
1. 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
Uniprot ID:
P60752
Molecular weight:
64460