Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB004114
Identification
Name: PG(19:iso/18:1(9Z))
Description:PG(19:iso/18:1(9Z)) 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(19:iso/18:1(9Z)), in particular, consists of one 17-methylocatdecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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:
  • 1-17-methylocatdecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)
  • 1-17-methylocatdecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoglycerol
  • 1-17-methylocatdecanoyl-2-oleoyl-sn-glycero-3-phosphoglycerol
  • GPG(19:0/18:1)
  • GPG(37:1)
  • PG(19:0/18:1)
  • PG(37:1)
  • Phosphatidylglycerol(19:0/18:1)
  • Phosphatidylglycerol(37:1)
Chemical Formula: C43H83O10P
Average Molecular Weight: 791.0869
Monoisotopic Molecular Weight: 790.572385388
InChI Key: CLLLSMNIWXUXFQ-QXMHVHEDSA-N
InChI:InChI=1S/C43H83O10P/c1-4-5-6-7-8-9-10-11-12-15-19-22-25-28-31-34-43(47)53-41(38-52-54(48,49)51-36-40(45)35-44)37-50-42(46)33-30-27-24-21-18-16-13-14-17-20-23-26-29-32-39(2)3/h11-12,39-41,44-45H,4-10,13-38H2,1-3H3,(H,48,49)/b12-11-
CAS number: Not Available
IUPAC Name:(2,3-dihydroxypropoxy)({3-[(17-methyloctadecanoyl)oxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy})phosphinic acid
Traditional IUPAC Name: 2,3-dihydroxypropoxy(3-[(17-methyloctadecanoyl)oxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid
SMILES:CCCCCCCC\C=C/CCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)CO
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
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Alkyl phosphate
  • Organic phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • 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 Solubility8.48e-05 mg/mLALOGPS
logP8.59ALOGPS
logP12.64ChemAxon
logS-7ALOGPS
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 Count43ChemAxon
Refractivity219.38 m3·mol-1ChemAxon
Polarizability97.33 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, Positivesplash10-01ec-3090221600-17392f747bb84f06ac62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01e9-5191012200-e2ff6b85e0e82bc70105View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9084102000-8287eaf2b1d6b1c2b9aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ec-3090221600-17392f747bb84f06ac62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01e9-5191012200-e2ff6b85e0e82bc70105View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9084102000-8287eaf2b1d6b1c2b9aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002k-0190020300-67335d99aa132d6b6d22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-4290100000-d533f5221e71189a7f3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9030100000-89b1b55ce251846c2435View 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
  • 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