Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB004052
Identification
Name: PG(12:0(3-OH)/19:iso)
Description:PG(12:0(3-OH)/19:iso) 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(3-OH)/19:iso), in particular, consists of one 3-hydroxydodecanoyl chain to the C-1 atom, and one 17-methylocatdecanoyl to the C-2 atom. In Pseudomonas aeruginosa 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:
  • 1-3-hydroxydodecanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phospho-(1'-glycerol)
  • 1-3-hydroxydodecanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerol
  • 1-3-hydroxydodecanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerol
  • GPG(12:0/19:0)
  • GPG(31:0)
  • PG(12:0/19:0)
  • PG(31:0)
  • Phosphatidylglycerol(12:0/19:0)
  • Phosphatidylglycerol(31:0)
Chemical Formula: C37H73O11P
Average Molecular Weight: 724.9427
Monoisotopic Molecular Weight: 724.48904969
InChI Key: IEZZFFDVHDTWPL-UHFFFAOYSA-N
InChI:InChI=1S/C37H73O11P/c1-4-5-6-7-15-19-22-25-33(39)27-37(42)45-30-35(31-47-49(43,44)46-29-34(40)28-38)48-36(41)26-23-20-17-14-12-10-8-9-11-13-16-18-21-24-32(2)3/h32-35,38-40H,4-31H2,1-3H3,(H,43,44)
CAS number: Not Available
IUPAC Name:(2,3-dihydroxypropoxy)({3-[(3-hydroxydodecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propoxy})phosphinic acid
Traditional IUPAC Name: 2,3-dihydroxypropoxy(3-[(3-hydroxydodecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acid
SMILES:CCCCCCCCCC(O)CC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCC(C)C
Chemical Taxonomy
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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphoglycerols
Direct Parent Phosphatidylglycerols
Alternative Parents
Substituents
  • 1,2-diacylglycerophosphoglycerol
  • Beta-hydroxy acid
  • Dialkyl phosphate
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Alkyl phosphate
  • Hydroxy acid
  • Phosphoric acid ester
  • Organic phosphate
  • Organic phosphoric acid derivative
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000304 mg/mLALOGPS
logP6.43ALOGPS
logP9.1ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area169.05 Å2ChemAxon
Rotatable Bond Count38ChemAxon
Refractivity192.17 m3·mol-1ChemAxon
Polarizability86.55 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-4670542900-4b4fb2c7245ab13f34fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-057i-7970332200-62af7dff5a74797e6178View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9451010000-a0be2ea3b7b505de0d53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-4670542900-4b4fb2c7245ab13f34fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-057i-7970332200-62af7dff5a74797e6178View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9451010000-a0be2ea3b7b505de0d53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1970312400-f499eef67a96b75e445dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00tb-5950101000-674a7ff7bc12d9eee3c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9220000000-024632831d25563a89faView in MoNA
References
References:
  • Casadei MA, Ma?as P, Niven G, Needs E, Mackey BM. (2002) "Role of membrane fluidity in pressure resistance of Escherichia coli NCTC 8164." Appl Environ Microbiol. 68(12):5965-72. Pubmed: 12450817
  • 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
  • Taylor SS, Heath EC. (1969) "The incorporation of beta-hydroxy fatty acids into a phospholipid of Escherichia coli B." J Biol Chem. 244(24):6605-16. Pubmed: 4902888
  • 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:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Locus Tag:
PA5089
Molecular weight:
83.4 kDa
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in phosphatidylglycerophosphatase activity
Specific function:
One of the three phospholipid phosphatases, specifically hydrolyzes phosphatidylglycerophosphate
Gene Name:
pgpA
Locus Tag:
PA4050
Molecular weight:
19.6 kDa
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
Locus Tag:
PA4997
Molecular weight:
66.4 kDa
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
Locus Tag:
PA5394
Molecular weight:
54.6 kDa
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
Locus Tag:
PA2155
Molecular weight:
46.5 kDa
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.

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
Locus Tag:
PA4997
Molecular weight:
66.4 kDa
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaE
Locus Tag:
PA4455
Molecular weight:
28.4 kDa