PG(17:0/17:0) (PAMDB001438)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001438
Identification
Name: PG(17:0/17:0)
Description:PG(17:0/17:0) 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(17:0/17:0), in particular, consists of two heptadecanoyl chains at positions C-1 and C-2. 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:
  • 1,2-diheptadecanoyl-rac-glycero-3-phosphoglycerol
  • 1,2-dimargaroyl-rac-glycero-3-phospho-(1'-glycerol)
  • 1,2-dimargaroyl-rac-glycero-3-phosphoglycerol
  • GPG(17:0/17:0)
  • GPG(34:0)
  • Heptadecanoate
  • Heptadecanoate, 1-[[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester
  • Heptadecanoic acid
  • Heptadecanoic acid, 1-[[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester
  • Margarate
  • Margaric acid
  • PG(34:0)
  • Phosphatidylglycerol(17:0/17:0)
  • Phosphatidylglycerol(34:0)
Chemical Formula: C40H79O10P
Average Molecular Weight: 751.023
Monoisotopic Molecular Weight: 750.54108526
InChI Key: ZBVHXVKEMAIWQQ-QPPIDDCLSA-N
InChI:InChI=1S/C40H79O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-39(43)47-35-38(36-49-51(45,46)48-34-37(42)33-41)50-40(44)32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h37-38,41-42H,3-36H2,1-2H3,(H,45,46)/t37-,38+/m0/s1
CAS number: Not Available
IUPAC Name:[(2R)-2,3-bis(heptadecanoyloxy)propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid
Traditional IUPAC Name: (2R)-2,3-bis(heptadecanoyloxy)propoxy(2S)-2,3-dihydroxypropoxyphosphinic acid
SMILES:[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCC
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
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000109 mg/mLALOGPS
logP8.27ALOGPS
logP11.83ChemAxon
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 Count42ChemAxon
Refractivity204.51 m3·mol-1ChemAxon
Polarizability93.11 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Water + PGP(16:1(9Z)/18:1(11Z)) > Phosphate + PG(17:0/17:0)
PG(17:0/17:0) + PE(18:1(9Z)/15:0) > Ethanolamine + CL(15:0cyclo/17:0cycw7c/17:0cycw7c/18:1(9Z))
PG(17:0/17:0) + PE(18:1(9Z)/15:0) > Ethanolamine + CL(15:0cyclo/17:0cycw7c/18:1(9Z)/17:0cycw7c)
PG(17:0/17:0) + PE(18:1(9Z)/15:0) > Ethanolamine + CL(15:0cyclo/18:1(9Z)/17:0cycw7c/17:0cycw7c)
PG(17:0/17:0) + PE(18:1(9Z)/15:0) > Ethanolamine + CL(17:0cycw7c/15:0cyclo/17:0cycw7c/18:1(9Z))
PG(17:0/17:0) + PE(18:1(9Z)/15:0) > Ethanolamine + CL(17:0cycw7c/15:0cyclo/18:1(9Z)/17:0cycw7c)
PG(17:0/17:0) + PE(15:0/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/17:0cycw7c/17:0cycw7c)
PG(17:0/17:0) + PE(19:iso/19:iso) > CL(19:0cycv8c/17:0cycw7c/17:0cycw7c/19:0cycv8c) + Ethanolamine
PE(14:0/19:iso) + PG(17:0/17:0) > CL(19:0cycv8c/17:0cycw7c/17:0cycw7c/14:0) + Ethanolamine
PG(17:0/17:0) + PE(17:0cycw7c/17:0cycw7c) > CL(17:0cycw7c/17:0cycw7c/17:0cycw7c/17:0cycw7c) + Ethanolamine
PG(17:0/17:0) + PE(19:iso/19:iso) > CL(17:0cycw7c/19:0cycv8c/17:0cycw7c/19:0cycv8c) + Ethanolamine
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fai-4151921700-4d3d360a320bebdd6f00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m1i-8295822300-69e0f805500660b429bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vi-9045420000-c158ef15f6e2fd81a3dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0v01-0190401400-b34b8c1de5582af533e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fvi-5290301000-2469df711f3e7cde2ca3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9020100000-b9fe8383dcbbca94115cView in MoNA
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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. Pubmed: 22102590
  • 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 ID9547115
Kegg IDNot Available
ChemSpider ID7826065
Wikipedia IDNot Available
BioCyc IDCPD-7830
EcoCyc IDCPD-7830

Enzymes

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
• 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
• 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