Record Information
Version2.0
Creation Date2012-07-30 14:55:10 -0600
Update Date2015-12-09 12:06:33 -0700
Secondary Accession Numbers
  • ECMDB21265
Identification
Name:PG(12:0/12:0)
Description:PG(12:0/12:0) 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(12:0/12:0), in particular, consists of two dodecanoyl chains at positions C-1 and C-2. In E. coli 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
Thumb
Synonyms:
  • 1,2-didodecanoyl-rac-glycero-3-phospho-(1'-glycerol)
  • 1,2-didodecanoyl-rac-glycero-3-phosphoglycerol
  • 1,2-didodecanoyl-rac-glycero-3-phosphoglycerol
  • 1,2-dilauroylphosphatidylglycerol
  • 3-2,3-dihydroxypropoxy(hydroxy)phosphoryloxy-2-dodecanoyloxypropyl dodecanoate
  • 3-2,3-Dihydroxypropoxy(hydroxy)phosphoryloxy-2-dodecanoyloxypropyl dodecanoic acid
  • 3-{(2,3-dihydroxypropoxy)(hydroxy)phosphoryloxy}-2-(dodecanoyloxy)propyl laate
  • 3-{(2,3-dihydroxypropoxy)(hydroxy)phosphoryloxy}-2-(dodecanoyloxy)propyl laic acid
  • 3-{(2,3-Dihydroxypropoxy)(hydroxy)phosphoryloxy}-2-(dodecanoyloxy)propyl laurate
  • 3-{(2,3-dihydroxypropoxy)(hydroxy)phosphoryloxy}-2-(dodecanoyloxy)propyl lauric acid
  • C12:0 PG
  • C12:0 phosphatidylglycerol
  • Didodecanoyl phosphatidylglycerol
  • Dilauroylphosphatidylglycerol
  • GPG(12:0/12:0)
  • GPG(24:0)
  • PG(24:0)
  • Phosphatidylglycerol(12:0/12:0)
  • Phosphatidylglycerol(24:0)
Chemical Formula:C30H59O10P
Weight:Average: 610.766
Monoisotopic: 610.384585098
InChI Key:LHCZDUCPSRJDJT-WUFINQPMSA-N
InChI:InChI=1S/C30H59O10P/c1-3-5-7-9-11-13-15-17-19-21-29(33)37-25-28(26-39-41(35,36)38-24-27(32)23-31)40-30(34)22-20-18-16-14-12-10-8-6-4-2/h27-28,31-32H,3-26H2,1-2H3,(H,35,36)/t27-,28+/m0/s1
CAS number:Not Available
IUPAC Name:[(2R)-2,3-bis(dodecanoyloxy)propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid
Traditional IUPAC Name:(2R)-2,3-bis(dodecanoyloxy)propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid
SMILES:[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCC
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerols
Direct ParentPhosphatidylglycerols
Alternative Parents
Substituents
  • 1,2-diacylglycerophosphoglycerol
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000774 mg/mLALOGPS
logP5.44ALOGPS
logP7.38ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area148.82 Å2ChemAxon
Rotatable Bond Count32ChemAxon
Refractivity158.5 m3·mol-1ChemAxon
Polarizability70.52 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Water + PGP(12:0/12:0) > PG(12:0/12:0) + Phosphate
2 PG(12:0/12:0) <> cardiolipin (tetradodecanoyl, n-C12:0) + Glycerol
Water + PGP(12:0/12:0) > PG(12:0/12:0) + Phosphate
Adenosine triphosphate + Water + PG(12:0/12:0) > ADP + Hydrogen ion + Phosphate + PG(12:0/12:0)
Adenosine triphosphate + Water + PG(12:0/12:0) > ADP + Hydrogen ion + Phosphate + PG(12:0/12:0)
2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + Adenosine triphosphate + Dodecanoate (N-C12:0) > Adenosine monophosphate + PG(12:0/12:0) + Pyrophosphate
Water + PG(12:0/12:0) > 1-Acyl-sn-glycero-3-phosphoglycerol (N-C12:0) + Dodecanoate (N-C12:0) + Hydrogen ion
Water + PG(12:0/12:0) > 2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + Dodecanoate (N-C12:0) + Hydrogen ion
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + PG(12:0/12:0) > Acyl phosphatidylglycerol (N-C12:0) + Glycerylphosphorylethanolamine
2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + PG(12:0/12:0) > Acyl phosphatidylglycerol (N-C12:0) + Glycerophosphoglycerol
2 PGP(12:0/12:0) + Water >2 PG(12:0/12:0) + Phosphate
PG(12:0/12:0) + PE(12:0(3-OH)/12:0(3-OH)) > Ethanolamine + CL(12:0(3-OH)/12:0(3-OH)/12:0/12:0)
PE(12:0(3-OH)/12:0) + PG(12:0/12:0) > Ethanolamine + CL(12:0(3-OH)/12:0/12:0/12:0)
PE(12:0(3-OH)/17:0cycw7c) + PG(12:0/12:0) > Ethanolamine + CL(12:0(3-OH)/17:0cycw7c/12:0/12:0)
PE(12:0/12:0(3-OH)) + PG(12:0/12:0) > Ethanolamine + CL(12:0/12:0(3-OH)/12:0/12:0)
PE(12:0/17:0cycw7c) + PG(12:0/12:0) Ethanolamine + CL(12:0/17:0cycw7c/12:0/12:0)
PG(12:0/12:0) + PE(16:0/12:0) > Ethanolamine + CL(16:0/12:0/12:0/12:0)
PE(16:1(9Z)/12:0) + PG(12:0/12:0) > CL(16:1(9Z)/12:0/12:0/12:0) + Ethanolamine
2 PG(12:0/12:0) > Glycerol + cardiolipin (tetradodecanoyl, n-C12:0)
PE(17:0cycw7c/12:0) + PG(12:0/12:0) > Ethanolamine + CL(17:0cycw7c/12:0/12:0/12:0)
PG(12:0/12:0) + PE(18:0/12:0) > Ethanolamine + CL(18:0/12:0/12:0/12:0)
PE(18:1(11Z)/12:0) + PG(12:0/12:0) > Ethanolamine + CL(18:1(11Z)/12:0/12:0/12:0)
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(3-OH)/12:0/12:0/12:0))PW001917 Pw001917Pw001917 greyscalePw001917 simple
phospholipid biosynthesis (CL(12:0(3-OH)/17:0cycw7c/12:0/12:0))PW001923 Pw001923Pw001923 greyscalePw001923 simple
phospholipid biosynthesis (CL(12:0/12:0(3-OH)/12:0/12:0))PW001929 Pw001929Pw001929 greyscalePw001929 simple
phospholipid biosynthesis (CL(12:0/12:0/12:0/12:0))PW001930 Pw001930Pw001930 greyscalePw001930 simple
phospholipid biosynthesis (CL(12:0/17:0cycw7c/12:0/12:0))PW001932 Pw001932Pw001932 greyscalePw001932 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(17:0cycw7c/12:0/12:0/12:0))PW001972 Pw001972Pw001972 greyscalePw001972 simple
phospholipid biosynthesis (CL(18:0/12:0/12:0/12:0))PW001975 Pw001975Pw001975 greyscalePw001975 simple
phospholipid biosynthesis (CL(18:1(11Z)/12:0/12:0/12:0))PW001977 Pw001977Pw001977 greyscalePw001977 simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:Not Available
References
References:
  • 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
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID24779549
Kegg IDNot Available
ChemSpider ID24823096
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Uniprot ID:
P07000
Molecular weight:
38978
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in phospholipase activity
Specific function:
Has broad substrate specificity including hydrolysis of phosphatidylcholine with phospholipase A2 (EC 3.1.1.4) and phospholipase A1 (EC 3.1.1.32) activities. Strong expression leads to outer membrane breakdown and cell death; is dormant in normal growing cells. Required for efficient secretion of bacteriocins
Gene Name:
pldA
Uniprot ID:
P0A921
Molecular weight:
33163
Reactions
Phosphatidylcholine + H(2)O = 2-acylglycerophosphocholine + a carboxylate.
Phosphatidylcholine + H(2)O = 1-acylglycerophosphocholine + a carboxylate.
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 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 transferase activity, transferring acyl groups
Specific function:
Plays a role in lysophospholipid acylation. Transfers fatty acids to the 1-position via an enzyme-bound acyl-ACP intermediate in the presence of ATP and magnesium. Its physiological function is to regenerate phosphatidylethanolamine from 2-acyl-glycero-3-phosphoethanolamine (2-acyl-GPE) formed by transacylation reactions or degradation by phospholipase A1
Gene Name:
aas
Uniprot ID:
P31119
Molecular weight:
80699
Reactions
Acyl-[acyl-carrier-protein] + O-(2-acyl-sn-glycero-3-phospho)ethanolamine = [acyl-carrier-protein] + O-(1-beta-acyl-2-acyl-sn-glycero-3-phospho)ethanolamine.
ATP + an acid + [acyl-carrier-protein] = AMP + diphosphate + acyl-[acyl-carrier-protein].
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
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
Uniprot ID:
P0A6H8
Molecular weight:
54822
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.
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
Uniprot ID:
P0AA84
Molecular weight:
47633
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.
General function:
cardiolipin biosynthetic process
Specific function:
Catalyzes the synthesis of cardiolipin (CL) (diphosphatidylglycerol) from phosphatidylglycerol (PG) and phosphatidylethanolamine (PE).
Gene Name:
clsC
Uniprot ID:
P75919
Molecular weight:
53665
Reactions
Phosphatidylglycerol + phosphatidylethanolamine = diphosphatidylglycerol + ethanolamine

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