Record Information
Version2.0
Creation Date2012-07-30 14:55:10 -0600
Update Date2015-12-09 17:01:32 -0700
Secondary Accession Numbers
  • ECMDB21273
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 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-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
Weight:Average: 859.069
Monoisotopic: 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
ClassificationNot classified
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000488 mg/mLALOGPS
logP7.47ALOGPS
logP12.59ChemAxon
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 Å2ChemAxon
Rotatable Bond Count46ChemAxon
Refractivity224.59 m3·mol-1ChemAxon
Polarizability101.8 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)/15:0cyclo/15:0cyclo/18:1(9Z))PW001441 Pw001441Pw001441 greyscalePw001441 simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo)PW001460 Pw001460Pw001460 greyscalePw001460 simple
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/17:0cycw7c/19:0cycv8c)PW001566 Pw001566Pw001566 greyscalePw001566 simple
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/18:1(9Z)/17:0cycw7c)PW001567 Pw001567Pw001567 greyscalePw001567 simple
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/19:0cycv8c/17:0cycw7c)PW001569 Pw001569Pw001569 greyscalePw001569 simple
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/19:0cycv8c/19:0cycv8c)PW001570 Pw001570Pw001570 greyscalePw001570 simple
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/17:0cycw7c/17:0cycw7c)PW001591 Pw001591Pw001591 greyscalePw001591 simple
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/19:0cycv8c/19:0cycv8c)PW001614 Pw001614Pw001614 greyscalePw001614 simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/17:0cycw7c/17:0cycw7c)PW001628 Pw001628Pw001628 greyscalePw001628 simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/17:0cycw7c/19:0cycv8c)PW001631 Pw001631Pw001631 greyscalePw001631 simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/18:1(9Z)/19:0cycv8c)PW001637 Pw001637Pw001637 greyscalePw001637 simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/19:0cycv8c/17:0cycw7c)PW001642 Pw001642Pw001642 greyscalePw001642 simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/19:0cycv8c/18:1(9Z))PW001643 Pw001643Pw001643 greyscalePw001643 simple
phospholipid biosynthesis I (18:0, 18:0)PW001001 Pw001001Pw001001 greyscalePw001001 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 IDHMDB13504
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