Record Information
Version2.0
Creation Date2012-07-30 14:55:10 -0600
Update Date2015-12-09 17:01:24 -0700
Secondary Accession Numbers
  • ECMDB21268
Identification
Name:PGP(12:0/12:0)
Description:PGP(12:0/12:0) 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(12:0/12:0), in particular, consists of two dodecanoyl 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-didodecanoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
  • 1,2-didodecanoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
  • 1,2-Didodecanoyl-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(24:0)
Chemical Formula:C30H60O13P2
Weight:Average: 690.745
Monoisotopic: 690.350915988
InChI Key:LNEADDPQSRWQGI-VSGBNLITSA-N
InChI:InChI=1S/C30H60O13P2/c1-3-5-7-9-11-13-15-17-19-21-29(32)39-25-28(43-30(33)22-20-18-16-14-12-10-8-6-4-2)26-42-45(37,38)41-24-27(31)23-40-44(34,35)36/h27-28,31H,3-26H2,1-2H3,(H,37,38)(H2,34,35,36)/t27-,28-/m1/s1
CAS number:Not Available
IUPAC Name:[(2R)-3-({[(2R)-2,3-bis(dodecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name:(2R)-3-{[(2R)-2,3-bis(dodecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
SMILES:[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCC
Chemical Taxonomy
ClassificationNot classified
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00645 mg/mLALOGPS
logP4.06ALOGPS
logP7.26ChemAxon
logS-5ALOGPS
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 Count34ChemAxon
Refractivity169.37 m3·mol-1ChemAxon
Polarizability76.26 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(12:0(3-OH)/12:0(3-OH)/12:0/12:0))PW001915 Pw001915Pw001915 greyscalePw001915 simple
phospholipid biosynthesis (CL(12:0/12:0/12:0/12:0))PW001930 Pw001930Pw001930 greyscalePw001930 simple
phospholipid biosynthesis (CL(16:0/12:0/12:0/12:0)) 2PW001952 Pw001952Pw001952 greyscalePw001952 simple
phospholipid biosynthesis (CL(16:1(9Z)/12:0/12:0/12:0))PW001955 Pw001955Pw001955 greyscalePw001955 simple
phospholipid biosynthesis (CL(18:0/12:0/12:0/12:0))PW001975 Pw001975Pw001975 greyscalePw001975 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