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Record Information
Version	2.0
Creation Date	2015-09-08 18:59:30 -0600
Update Date	2015-12-09 12:07:37 -0700
Secondary Accession Numbers	ECMDB24265
Identification
Name:	PG(16:0/22:5(7Z,10Z,13Z,16Z,19Z))
Description	PG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)) 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(16:0/22:5(7Z,10Z,13Z,16Z,19Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 7Z,10Z,13Z,16Z,19Z-docosapentaenoyl 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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa5d1f54c> Close
Synonyms:	Value Source 1-clupanodonoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-glycerol) SMPDB, HMDB 1-clupanodonoyl-2-palmitoyl-sn-glycero-3-phosphoglycerol SMPDB, HMDB PG(22:5/16:0) SMPDB, HMDB PG(22:5n3/16:0) SMPDB, HMDB PG(22:5w3/16:0) SMPDB, HMDB PG(38:5) SMPDB, HMDB Phosphatidylglycerol(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) SMPDB, HMDB Phosphatidylglycerol(22:5/16:0) SMPDB, HMDB Phosphatidylglycerol(22:5n3/16:0) SMPDB, HMDB Phosphatidylglycerol(22:5w3/16:0) SMPDB, HMDB Phosphatidylglycerol(38:5) SMPDB, HMDB PG(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) SMPDB PG(38:5) Lipid Annotator PG(22:5/16:0) Lipid Annotator 1-docosapentaenoyl-2-palmitoyl-sn-glycero-3-phosphoglycerol Lipid Annotator, HMDB GPG(38:5) Lipid Annotator, HMDB 1-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-2-hexadecanoyl-sn-glycero-3-phospho-(1'-glycerol) Lipid Annotator, HMDB GPG(22:5/16:0) Lipid Annotator, HMDB Phosphatidylglycerol(22:5/16:0) Lipid Annotator 1-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-2-hexadecanoyl-sn-glycero-3-phosphoglycerol Lipid Annotator, HMDB
Chemical Formula:	C44H77O10P
Weight:	Average: 797.064 Monoisotopic: 796.525435677
InChI Key:	IUTIUWYTMFXMMO-RUVFBLPJSA-N
InChI:	InChI=1S/C44H77O10P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-43(47)51-39-42(40-53-55(49,50)52-38-41(46)37-45)54-44(48)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2/h5,7,11,13,17-18,20-21,24-25,41-42,45-46H,3-4,6,8-10,12,14-16,19,22-23,26-40H2,1-2H3,(H,49,50)/b7-5-,13-11-,18-17-,21-20-,25-24-/t41-,42+/m0/s1
CAS number:	Not Available
IUPAC Name:	[(2S)-2,3-dihydroxypropoxy][(2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-(hexadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name:	(2S)-2,3-dihydroxypropoxy((2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-(hexadecanoyloxy)propoxy)phosphinic acid
SMILES:	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)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.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Glycerophospholipids
Sub Class	Glycerophosphoglycerols
Direct Parent	Phosphatidylglycerols
Alternative Parents	Fatty acid esters Dialkyl phosphates Dicarboxylic acids and derivatives Secondary alcohols Carboxylic acid esters 1,2-diols Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 7.9e-05 g/L ALOGPS logP 8.21 ALOGPS logP 11.79 ChemAxon logS -7 ALOGPS pKa (Strongest Acidic) 1.89 ChemAxon pKa (Strongest Basic) -3 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 148.82 Ų ChemAxon Rotatable Bond Count 41 ChemAxon Refractivity 228.5 m³·mol⁻¹ ChemAxon Polarizability 93.77 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Membrane
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004i-4175352900-544e48d51ad60f24d74a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0570-5294221400-e4d5880f24993ee3c6b8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0c2i-9265112000-411f8a8d3cbcfbcf09b1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-06vi-1149120500-b6417cd7a9e601fb7efa View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-6229100100-877a02530cdd2509ad26 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9011000000-aac0a3cb9c2fc22eb72f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0002-0000000900-9869f21529424c0a4adf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0a6s-0179320700-8908ba5b067a32ea58f0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a92-0279320700-bea8cb3cea623e00c933 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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 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
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID HMDB0116621 Pubchem Compound ID 131823258 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available