Record Information
Version2.0
Creation Date2012-08-13 14:57:53 -0600
Update Date2015-12-09 12:07:29 -0700
Secondary Accession Numbers
  • ECMDB21638
Identification
Name:PG(16:0/17:0cycw7c)
DescriptionPG(16:0/17:0cycw7c) 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(16:0/17:0cycw7c), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one heptadec-9-10-cyclo-anoyl 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-hexadecanoyl-2-heptadec-9-10-cyclo-anoyl-sn-glycero-3-phospho-(1'-glycerol)
  • 1-hexadecanoyl-2-heptadec-9-10-cyclo-anoyl-sn-glycero-3-phosphoglycerol
  • 1-hexadecanoyl-2-NULL-sn-glycero-3-phospho-(1'-glycerol)
  • 1-hexadecanoyl-2-NULL-sn-glycero-3-phosphoglycerol
  • 1-palmitoyl-2-heptadec-9-10-cyclo-anoyl-sn-glycero-3-phosphoglycerol
  • 1-palmitoyl-2-heptadec-cyclopropanol-sn-glycero-3-phosphoglycerol
  • GPG(16:0/17:0)
  • GPG(33:0)
  • PG(16:0/17:0)
  • PG(33:0)
  • Phosphatidylglycerol(16:0/17:0)
  • Phosphatidylglycerol(33:0)
Chemical Formula:C39H75O10P
Weight:Average: 734.993
Monoisotopic: 734.509785613
InChI Key:KSFYDWLGWRUFCG-IUMVPMKHSA-N
InChI:InChI=1S/C39H75O10P/c1-3-5-7-9-10-11-12-13-14-15-16-19-24-28-39(43)49-37(33-48-50(44,45)47-31-36(41)30-40)32-46-38(42)27-23-20-17-18-22-26-35-29-34(35)25-21-8-6-4-2/h34-37,40-41H,3-33H2,1-2H3,(H,44,45)/t34?,35?,36-,37+/m0/s1
CAS number:Not Available
IUPAC Name:[(2S)-2,3-dihydroxypropoxy][(2R)-2-(hexadecanoyloxy)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy]phosphinic acid
Traditional IUPAC Name:(2S)-2,3-dihydroxypropoxy((2R)-2-(hexadecanoyloxy)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy)phosphinic acid
SMILES:[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCCCCCCCCC
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerols
Direct ParentPhosphatidylglycerols
Alternative Parents
Substituents
  • 1,2-diacylglycerophosphoglycerol
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00013 g/LALOGPS
logP7.7ALOGPS
logP10.6ChemAxon
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 Count39ChemAxon
Refractivity198 m³·mol⁻¹ChemAxon
Polarizability88.06 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
phospholipid biosynthesis (CL(18:1(9Z)/16:0/16:0/17:0cycw7c))PW002012 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/17:0cycw7c/16:0))PW001445 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/17:0cycw7c/17:0cycw7c/17:0cycw7c)PW001351 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/17:0cycw7c/19:0cycv8c/19:0cycv8c)PW001354 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/19:0cycv8c/17:0cycw7c/19:0cycv8c)PW001401 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/19:0cycv8c/19:0cycv8c/17:0cycw7c)PW001412 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(17:0cycw7c/16:0/17:0cycw7c/17:0cycw7c)PW001683 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00n0-3090610500-366bb9bfa18a7e7e4075View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02dr-5291411100-f952b6d8e99b4ee21932View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvi-9383142000-5697fdb7df7e40665e6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-0190200200-6654774c12f9bd8e8f5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01dj-5290100000-0217d91bf2298dd2a86fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9020000000-d68938888c7f835e4fc6View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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
  • Oursel, D., Loutelier-Bourhis, C., Orange, N., Chevalier, S., Norris, V., Lange, C. M. (2007). "Lipid composition of membranes of Escherichia coli by liquid chromatography/tandem mass spectrometry using negative electrospray ionization." Rapid Commun Mass Spectrom 21:1721-1728. Pubmed: 17477452
  • 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:
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:
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:
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