PG(19:iso/15:0) (PAMDB004109)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB004109
Identification
Name: PG(19:iso/15:0)
Description:PG(19:iso/15:0) 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(19:iso/15:0), in particular, consists of one 17-methylocatdecanoyl chain to the C-1 atom, and one pentadecanoyl 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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1-17-methylocatdecanoyl-2-pentadecanoyl-sn-glycero-3-phospho-(1'-glycerol)
  • 1-17-methylocatdecanoyl-2-pentadecanoyl-sn-glycero-3-phosphoglycerol
  • 1-17-methylocatdecanoyl-2-pentadecanoyl-sn-glycero-3-phosphoglycerol
  • GPG(19:0/15:0)
  • GPG(34:0)
  • PG(19:0/15:0)
  • PG(34:0)
  • Phosphatidylglycerol(19:0/15:0)
  • Phosphatidylglycerol(34:0)
Chemical Formula: C40H79O10P
Average Molecular Weight: 751.023
Monoisotopic Molecular Weight: 750.54108526
InChI Key: OXHYXPPQIBTPHV-UHFFFAOYSA-N
InChI:InChI=1S/C40H79O10P/c1-4-5-6-7-8-9-10-15-19-22-25-28-31-40(44)50-38(35-49-51(45,46)48-33-37(42)32-41)34-47-39(43)30-27-24-21-18-16-13-11-12-14-17-20-23-26-29-36(2)3/h36-38,41-42H,4-35H2,1-3H3,(H,45,46)
CAS number: Not Available
IUPAC Name:(2,3-dihydroxypropoxy)({3-[(17-methyloctadecanoyl)oxy]-2-(pentadecanoyloxy)propoxy})phosphinic acid
Traditional IUPAC Name: 2,3-dihydroxypropoxy(3-[(17-methyloctadecanoyl)oxy]-2-(pentadecanoyloxy)propoxy)phosphinic acid
SMILES:CCCCCCCCCCCCCCC(=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 glycerophosphoserines. These are lipids containing a glycerol moiety carrying a phosphoserine at the 3-position.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphoserines
Direct Parent Glycerophosphoserines
Alternative Parents
Substituents
  • Glycerophosphoserine
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphate
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • 1,2-diol
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid salt
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic anion
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Amine
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Primary alcohol
  • 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 Solubility0.00011 mg/mLALOGPS
logP7.99ALOGPS
logP11.67ChemAxon
logS-6.8ALOGPS
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 Count41ChemAxon
Refractivity204.46 m3·mol-1ChemAxon
Polarizability92.32 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
PE(19:iso/15:0) + PG(19:iso/15:0) > Ethanolamine + CL(15:0cyclo/15:0cyclo/19:0cycv8c/19:0cycv8c)
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fc0-3190250600-e654755f94dddd7875f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-5391031100-45b3ca7457c044e42798View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9532120000-f1ec7bc20698991b1876View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-0190020300-2864a293c40481f736a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-4290000000-8bcb2e15b464f9e09d91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9130000000-842309d5d6d65788b9c1View 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

Protein Details
• Lysophospholipase L2
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.
Protein Details
• Phosphatidylglycerophosphatase A
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.
Protein Details
• Lipid A export ATP-binding/permease protein msbA
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
Protein Details
• Cardiolipin synthase
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.
Protein Details
• Putative cardiolipin synthase ybhO
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

Protein Details
• Lipid A export ATP-binding/permease protein msbA
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
Protein Details
• Probable phospholipid ABC transporter permease protein mlaE
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