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Record Information
Version	2.0
Creation Date	2015-09-08 17:49:34 -0600
Update Date	2015-12-09 12:07:45 -0700
Secondary Accession Numbers	ECMDB24133
Identification
Name:	PG(16:1(9Z)/18:1(9Z))
Description	PG(16:1(9Z)/18:1(9Z)) 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(16:1(9Z)/18:1(9Z)), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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:0xa6168568> Close
Synonyms:	Value Source 1-(9Z-Octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-(1'-glycerol) HMDB 1-Oleoyl-2-palmitoleoyl-sn-glycero-3-phosphoglycerol HMDB GPG(18:1/16:1) HMDB GPG(18:1N9/16:1N7) HMDB GPG(18:1W9/16:1W7) HMDB GPG(34:2) HMDB PG(18:1/16:1) HMDB PG(18:1N9/16:1N7) HMDB PG(18:1W9/16:1W7) HMDB PG(34:2) HMDB Phosphatidylglycerol(18:1/16:1) HMDB Phosphatidylglycerol(18:1n9/16:1n7) HMDB Phosphatidylglycerol(18:1W9/16:1W7) HMDB Phosphatidylglycerol(34:2) HMDB 1-(9Z-Octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoglycerol HMDB PG(18:1(9Z)/16:1(9Z)) Lipid Annotator
Chemical Formula:	C40H75O10P
Weight:	Average: 746.9913 Monoisotopic: 746.509785132
InChI Key:	QGIXWNRQEFVVRM-GDNUZSQHSA-N
InChI:	InChI=1S/C40H75O10P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-39(43)47-35-38(36-49-51(45,46)48-34-37(42)33-41)50-40(44)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h14,16-18,37-38,41-42H,3-13,15,19-36H2,1-2H3,(H,45,46)/b16-14-,18-17-/t37-,38+/m0/s1
CAS number:	Not Available
IUPAC Name:	[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name:	(2S)-2,3-dihydroxypropoxy((2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid
SMILES:	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\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. 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.
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	Diacylglycerophosphoglycerols (LMGP04010881 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.00011 g/L ALOGPS logP 8.02 ALOGPS logP 11.1 ChemAxon logS -6.8 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 40 ChemAxon Refractivity 206.74 m³·mol⁻¹ ChemAxon Polarizability 88.49 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(18:0/18:0) + Water > PG(16:1(9Z)/18:1(9Z)) + Phosphate PGP(16:1(9Z)/18:1(9Z)) + Water > PG(16:1(9Z)/18:1(9Z)) + Phosphate PE(15:0/15:0) + PG(16:1(9Z)/18:1(9Z)) > Ethanolamine + CL(16:1(9Z)/15:0cyclo/15:0cyclo/18:1(9Z)) PG(16:1(9Z)/18:1(9Z)) + PE(15:0/15:0) > CL(16:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo) + Ethanolamine PE(17:0cycw7c/17:0cycw7c) + PG(16:1(9Z)/18:1(9Z)) > Ethanolamine + CL(16:1(9Z)/17:0cycw7c/17:0cycw7c/18:1(9Z)) PE(17:0cycw7c/17:0cycw7c) + PG(16:1(9Z)/18:1(9Z)) > CL(16:1(9Z)/17:0cycw7c/18:1(9Z)/17:0cycw7c) + Ethanolamine PG(16:1(9Z)/18:1(9Z)) + PE(17:0cycw7c/17:0cycw7c) > Ethanolamine + CL(16:1(9Z)/18:1(9Z)/17:0cycw7c/17:0cycw7c) PE(19:iso/19:iso) + PG(16:1(9Z)/18:1(9Z)) > Ethanolamine + CL(16:1(9Z)/18:1(9Z)/19:0cycv8c/19:0cycv8c) PG(16:1(9Z)/18:1(9Z)) + PE(19:iso/19:iso) > CL(16:1(9Z)/19:0cycv8c/18:1(9Z)/19:0cycv8c) + Ethanolamine PE(19:iso/19:iso) + PG(16:1(9Z)/18:1(9Z)) > Ethanolamine + CL(16:1(9Z)/19:0cycv8c/19:0cycv8c/18:1(9Z)) PG(16:1(9Z)/18:1(9Z)) + PE(15:0/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/16:1(9Z)/18:1(9Z)) PE(19:0cycv8c/19:iso) + PG(16:1(9Z)/18:1(9Z)) > Ethanolamine + CL(19:0cycv8c/16:1(9Z)/18:1(9Z)/19:0cycv8c) PG(16:1(9Z)/18:1(9Z)) + PE(17:0cycw7c/17:0cycw7c) > Ethanolamine + CL(17:0cycw7c/16:1(9Z)/18:1(9Z)/17:0cycw7c) PG(16:1(9Z)/18:1(9Z)) + PE(17:0cycw7c/17:0cycw7c) > Ethanolamine + CL(17:0cycw7c/16:1(9Z)/17:0cycw7c/18:1(9Z)) PE(16:0/19:0cycw8c) + PG(16:1(9Z)/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/16:0/16:0/19:0cycv8c) PE(18:1(9Z)/16:0) + PG(16:1(9Z)/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/16:0/16:1(9Z)/18:1(9Z))
SMPDB Pathways:	phospholipid biosynthesis (CL(17:0cycw7c/16:1(9Z)/17:0cycw7c/18:1(9Z))) PW001698 phospholipid biosynthesis (CL(17:0cycw7c/16:1(9Z)/18:1(9Z)/17:0cycw7c)) PW001700 phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/16:1(9Z)/18:1(9Z))) PW001519 phospholipid biosynthesis (CL(18:1(9Z)/16:0/16:1(9Z)/18:1(9Z))) PW002013 phospholipid biosynthesis (CL(19:0cycv8c/16:1(9Z)/18:1(9Z)/19:0cycv8c)) PW001387 phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/15:0cyclo/18:1(9Z)) PW001441 phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo) PW001460 phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/17:0cycw7c/18:1(9Z)) PW001565 phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/18:1(9Z)/17:0cycw7c) PW001567 phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/17:0cycw7c/17:0cycw7c) PW001591 phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/19:0cycv8c/19:0cycv8c) PW001614 phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/18:1(9Z)/19:0cycv8c) PW001637 phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/19:0cycv8c/18:1(9Z)) PW001643
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 GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00or-3190520500-b9b2250a97ef42e753ae View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00or-4191311100-23d57e29501089b016eb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0ar9-9073240000-7bc9aa80b3261990bf4f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0gx1-0190200200-701c53e09b09bf048656 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-01z9-4290100000-e48b747ecad89965d61e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9030000000-a348c66bf164f3be2004 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0002-0000000900-6a6a3edc7613adf01568 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0uf1-0090300400-d377ddb6dd8dfe25475a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0uf1-0190300400-5254bc3d1dcb8621b286 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 89398 HMDB ID HMDB0010631 Pubchem Compound ID 52927146 Kegg ID Not Available ChemSpider ID 24768130 Wikipedia ID Not Available BioCyc ID Not Available

Enzymes