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Record Information
Version	2.0
Creation Date	2015-09-08 17:49:37 -0600
Update Date	2015-12-09 12:08:21 -0700
Secondary Accession Numbers	ECMDB24137
Identification
Name:	PG(18:2(9Z,12Z)/18:2(9Z,12Z))
Description	PG(18:2(9Z,12Z)/18:2(9Z,12Z)) 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(18:2(9Z,12Z)/18:2(9Z,12Z)), in particular, consists of two 9Z,12Z-octadecadienoyl chains at positions C-1 and C-2. 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:0xa979b810> Close
Synonyms:	Not Available
Chemical Formula:	C44H79O10P
Weight:	Average: 799.08 Monoisotopic: 798.541085742
InChI Key:	DQZVAGRJTACCBC-NHPPMFAOSA-N
InChI:	InChI=1S/C44H79O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-43(47)51-39-42(40-53-55(49,50)52-38-41(46)37-45)54-44(48)36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,19-22,41-42,45-46H,3-12,17-18,23-40H2,1-2H3,(H,49,50)/b15-13-,16-14-,21-19-,22-20-/t41-,42+/m0/s1
CAS number:	Not Available
IUPAC Name:	[(2R)-2,3-bis[(9Z,12Z)-nonadeca-9,12-dienoyloxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid
Traditional IUPAC Name:	(2R)-2,3-bis[(9Z,12Z)-nonadeca-9,12-dienoyloxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid
SMILES:	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCCC
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 7.8e-05 g/L ALOGPS logP 8.36 ALOGPS logP 12.16 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 42 ChemAxon Refractivity 227.38 m³·mol⁻¹ ChemAxon Polarizability 94.54 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:	PGP(18:2(9Z,12Z)/18:2(9Z,12Z)) + Water > Phosphate + PG(18:2(9Z,12Z)/18:2(9Z,12Z)) PG(18:2(9Z,12Z)/18:2(9Z,12Z)) + PE(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) > CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) + Ethanolamine PG(18:2(9Z,12Z)/18:2(9Z,12Z)) > CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) + Glycerol
SMPDB Pathways:	phospholipid biosynthesis I (CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) ) PW001025
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 LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-057j-4151162900-68ca1ba18a85bf14193a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-056r-8294254700-40a2d0c458900e4f1f7d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a70-9046224200-8908cdb0a51ab6703260 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0fi4-1190040500-f276e9a520fe3ce812ed View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004l-5290110100-9b9d996125813835c8bc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9010100000-c3c6f0356806ef8821f6 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 Not Available Pubchem Compound ID Not Available Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

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