Record Information
Version2.0
Creation Date2012-10-24 09:55:01 -0600
Update Date2015-09-16 17:34:54 -0600
Secondary Accession Numbers
  • ECMDB23688
Identification
Name:PG(15:0/19:iso)
DescriptionPG(15:0/19: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(15:0/19:iso), in particular, consists of one pentadecanoyl chain to the C-1 atom, and one 17-methylocatdecanoyl to the C-2 atom. 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-pentadecanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phospho-(1'-glycerol)
  • 1-pentadecanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerol
  • 1-pentadecanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerol
  • GPG(15:0/19:0)
  • GPG(34:0)
  • PG(15:0/19:0)
  • PG(34:0)
  • Phosphatidylglycerol(15:0/19:0)
  • Phosphatidylglycerol(34:0)
Chemical Formula:C40H79O10P
Weight:Average: 751.023
Monoisotopic: 750.54108526
InChI Key:VAZQYSNUEMMQKX-UHFFFAOYSA-N
InChI:InChI=1S/C40H79O10P/c1-4-5-6-7-8-9-10-15-18-21-24-27-30-39(43)47-34-38(35-49-51(45,46)48-33-37(42)32-41)50-40(44)31-28-25-22-19-16-13-11-12-14-17-20-23-26-29-36(2)3/h36-38,41-42H,4-35H2,1-3H3,(H,45,46)
CAS number:Not Available
IUPAC Name:(2,3-dihydroxypropoxy)({2-[(17-methyloctadecanoyl)oxy]-3-(pentadecanoyloxy)propoxy})phosphinic acid
Traditional IUPAC Name:2,3-dihydroxypropoxy(2-[(17-methyloctadecanoyl)oxy]-3-(pentadecanoyloxy)propoxy)phosphinic acid
SMILES:CCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCC(C)C
Chemical Taxonomy
Description 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. 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerols
Direct ParentPhosphatidylglycerols
Alternative Parents
Substituents
  • 1,2-diacylglycerophosphoglycerol
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00011 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity204.46 m³·mol⁻¹ChemAxon
Polarizability92.35 ųChemAxon
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(9Z)) > Phosphate + PG(15:0/19:iso)
PE(15:0/15:0) + PG(15:0/19:iso) > Ethanolamine + CL(15:0cyclo/15:0cyclo/15:0cyclo/19:0cycv8c)
PE(15:0/15:0) + PG(15:0/19:iso) > Ethanolamine + CL(15:0cyclo/15:0cyclo/18:1(9Z)/15:0cyclo)
PG(15:0/19:iso) + PE(15:0/18:1(9Z)) > Ethanolamine + CL(15:0cyclo/15:0cyclo/18:1(9Z)/19:0cycv8c)
PE(15:0/18:1(9Z)) + PG(15:0/19:iso) > Ethanolamine + CL(15:0cyclo/15:0cyclo/19:0cycv8c/18:1(9Z))
PE(15:0/19:iso) + PG(15:0/19:iso) > CL(15:0cyclo/15:0cyclo/19:0cycv8c/19:0cycv8c) + Ethanolamine
PE(15:0/18:1(9Z)) + PG(15:0/19:iso) > Ethanolamine + CL(15:0cyclo/18:1(9Z)/15:0cyclo/19:0cycv8c)
PG(15:0/19:iso) + PE(15:0/18:1(9Z)) > Ethanolamine + CL(15:0cyclo/18:1(9Z)/19:0cycv8c/15:0cyclo)
PE(15:0/19:iso) + PG(15:0/19:iso) > Ethanolamine + CL(15:0cyclo/19:0cycv8c/15:0cyclo/19:0cycv8c)
PE(15:0/17:0cycw7c) + PG(15:0/19:iso) > Ethanolamine + CL(15:0cyclo/19:0cycv8c/17:0cycw7c/15:0cyclo)
PE(15:0/19:iso) + PG(15:0/19:iso) > Ethanolamine + CL(15:0cyclo/19:0cycv8c/19:0cycv8c/15:0cyclo)
PG(15:0/19:iso) + PE(18:1(9Z)/19:iso) > Ethanolamine + CL(15:0cyclo/19:0cycv8c/19:0cycv8c/18:1(9Z))
PE(19:iso/19:iso) + PG(15:0/19:iso) > Ethanolamine + CL(15:0cyclo/19:0cycv8c/19:0cycv8c/19:0cycv8c)
PE(16:1(9Z)/19:iso) + PG(15:0/19:iso) > CL(19:0cycv8c/15:0cyclo/16:0/19:0cycv8c) + Ethanolamine
PG(15:0/19:iso) + PE(16:0/19:0cycw8c) > CL(19:0cycv8c/15:0cyclo/16:0/19:0cycv8c) + Ethanolamine
PE(16:1(9Z)/19:iso) + PG(15:0/19:iso) > CL(19:0cycv8c/15:0cyclo/16:1(9Z)/19:0cycv8c) + Ethanolamine
PE(18:1(9Z)/19:iso) + PG(15:0/19:iso) > CL(19:0cycv8c/15:0cyclo/18:1(9Z)/19:0cycv8c) + Ethanolamine
PE(19:iso/19:iso) + PG(15:0/19:iso) > Ethanolamine + CL(19:0cycv8c/15:0cyclo/19:0cycv8c/19:0cycv8c)
PE(15:0/19:iso) + PG(15:0/19:iso) > CL(19:0cycv8c/15:0cyclo/19:0cycv8c/15:0cyclo) + Ethanolamine
PG(15:0/19:iso) + PE(18:1(9Z)/19:iso) > Ethanolamine + CL(19:0cycv8c/15:0cyclo/19:0cycv8c/18:1(9Z))
PE(15:0/17:0cycw7c) + PG(15:0/19:iso) > CL(19:0cycv8c/15:0cyclo/17:0cycw7c/15:0cyclo) + Ethanolamine
2 PGP(15:0/19:iso) + Water >2 PG(15:0/19:iso) + Phosphate
SMPDB Pathways:
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/15:0cyclo/19:0cycv8c)PW001065 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/15:0cyclo)PW001082 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/16:0/19:0cycv8c))PW001299 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/16:1(9Z)/19:0cycv8c))PW001300 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/17:0cycw7c/15:0cyclo))PW001301 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/18:1(9Z)/19:0cycv8c))PW001304 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/19:0cycv8c/15:0cyclo))PW001310 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/19:0cycv8c/18:1(9Z)))PW001318 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/19:0cycv8c/19:0cycv8c))PW001319 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/19:0cycv8c)PW001086 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/19:0cycv8c/18:1(9Z))PW001092 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/19:0cycv8c/19:0cycv8c)PW001093 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/15:0cyclo/19:0cycv8c)PW001164 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/19:0cycv8c/15:0cyclo)PW001179 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/15:0cyclo/19:0cycv8c)PW001188 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/19:0cycv8c/15:0cyclo)PW001199 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/19:0cycv8c/18:1(9Z))PW001202 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/19:0cycv8c/19:0cycv8c)PW001203 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fc0-3190330500-b8d486dbd6055e83c86bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-5390121100-e79a2e827a47c39b4570View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7j-9382020000-66f94b3f3dcf9564ad79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fdn-0190200200-1fa476e272b9308f134eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00bc-4390101000-6050d596f4d722727223View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9130000000-6e9b285587a12dde8e0eView in MoNA
References
References:
  • Casadei MA, Mañas 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
Uniprot ID:
P07000
Molecular weight:
38978
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + 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 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:
Not Available
Specific function:
Not known; overproduction leads to camphor resistance and chromosome condensation
Gene Name:
crcA
Uniprot ID:
P37001
Molecular weight:
21770
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 phospholipid transporter activity
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:
mlaB
Uniprot ID:
P64602
Molecular weight:
10680
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:
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:
mlaD
Uniprot ID:
P64604
Molecular weight:
19576
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
Uniprot ID:
P64606
Molecular weight:
27863