Record Information
Version2.0
Creation Date2012-07-30 14:55:10 -0600
Update Date2015-12-09 17:01:27 -0700
Secondary Accession Numbers
  • ECMDB21270
Identification
Name:PGP(14:1(7Z)/14:1(7Z))
Description:PGP(14:1(7Z)/14:1(7Z)) 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(14:1(7Z)/14:1(7Z)), in particular, consists of two 7Z,tetradecenoyl 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
Synonyms:
  • 1,2-di(7Z-tetradecenoyl)-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
  • 1,2-Di(7Z-tetradecenoyl)-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphoric acid)
  • 1,2-di7Z-tetradecenoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
  • 1,2-Di7Z-tetradecenoyl-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'-phosphoric acid
  • PGP(14:1/14:1)
  • PGP(28:2)
Chemical Formula:C34H64O13P2
Weight:Average: 742.821
Monoisotopic: 742.382216117
InChI Key:GDLXTQRUMWAYHJ-ORNOOMOASA-N
InChI:InChI=1S/C34H64O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-33(36)43-29-32(30-46-49(41,42)45-28-31(35)27-44-48(38,39)40)47-34(37)26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,31-32,35H,3-12,17-30H2,1-2H3,(H,41,42)(H2,38,39,40)/b15-13-,16-14-/t31-,32-/m1/s1
CAS number:Not Available
IUPAC Name:[(2R)-3-({[(2R)-2,3-bis[(7Z)-tetradec-7-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name:(2R)-3-{[(2R)-2,3-bis[(7Z)-tetradec-7-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
SMILES:[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCC\C=C/CCCCCC)OC(=O)CCCCC\C=C/CCCCCC
Chemical Taxonomy
ClassificationNot classified
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00369 mg/mLALOGPS
logP5.37ALOGPS
logP8.31ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)1.35ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area195.35 Å2ChemAxon
Rotatable Bond Count36ChemAxon
Refractivity190.01 m3·mol-1ChemAxon
Polarizability81.03 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
phospholipid biosynthesis CL(16:1(9Z)/14:0/17:0cycw7c/17:0cycw7c)PW001421 Pw001421Pw001421 greyscalePw001421 simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/19:0cycv8c/19:0cycv8c)PW001430 Pw001430Pw001430 greyscalePw001430 simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/14:0/15:0cyclo)PW001431 Pw001431Pw001431 greyscalePw001431 simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/15:0cyclo/14:0) )PW001724 Pw001724Pw001724 greyscalePw001724 simple
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/14:0/17:0cycw7c)PW001559 Pw001559Pw001559 greyscalePw001559 simple
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/17:0cycw7c/14:0)PW001562 Pw001562Pw001562 greyscalePw001562 simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/14:0/19:0cycv8c)PW001617 Pw001617Pw001617 greyscalePw001617 simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/19:0cycv8c/14:0)PW001639 Pw001639Pw001639 greyscalePw001639 simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:Not Available
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 IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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.
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.
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.
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

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