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Record Information
Version	2.0
Creation Date	2015-09-08 18:59:45 -0600
Update Date	2015-12-09 12:08:04 -0700
Secondary Accession Numbers	ECMDB24273
Identification
Name:	PG(18:0/18:1(9Z))
Description	PG(18:0/18:1(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(18:0/18:1(9Z)), in particular, consists of one octadecanoyl 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:0xa7ba799c> Close
Synonyms:	Value Source 1-(9Z-Octadecenoyl)-2-octadecanoyl-sn-glycero-3-phospho-(1'-glycerol) HMDB 1-Oleoyl-2-stearoyl-sn-glycero-3-phosphoglycerol HMDB GPG(18:1/18:0) HMDB GPG(18:1N9/18:0) HMDB GPG(18:1W9/18:0) HMDB GPG(36:1) HMDB PG(18:1/18:0) HMDB PG(18:1N9/18:0) HMDB PG(18:1W9/18:0) HMDB PG(36:1) HMDB Phosphatidylglycerol(18:1/18:0) HMDB Phosphatidylglycerol(18:1n9/18:0) HMDB Phosphatidylglycerol(18:1W9/18:0) HMDB Phosphatidylglycerol(36:1) HMDB 1-(9Z-Octadecenoyl)-2-octadecanoyl-sn-glycero-3-phosphoglycerol HMDB PG(18:1(9Z)/18:0) Lipid Annotator
Chemical Formula:	C42H81O10P
Weight:	Average: 777.0603 Monoisotopic: 776.556735324
InChI Key:	URDBSUCIYKJPCG-INSSKLQOSA-N
InChI:	InChI=1S/C42H81O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17,19,39-40,43-44H,3-16,18,20-38H2,1-2H3,(H,47,48)/b19-17-/t39-,40+/m0/s1
CAS number:	Not Available
IUPAC Name:	[(2S)-2,3-dihydroxypropoxy][(2R)-3-[(9Z)-octadec-9-enoyloxy]-2-(octadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name:	(2S)-2,3-dihydroxypropoxy(2R)-3-[(9Z)-octadec-9-enoyloxy]-2-(octadecanoyloxy)propoxyphosphinic acid
SMILES:	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC
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 (LMGP04010961 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 8.4e-05 g/L ALOGPS logP 8.58 ALOGPS logP 12.35 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 43 ChemAxon Refractivity 214.83 m³·mol⁻¹ ChemAxon Polarizability 94.1 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:	2 PGP(18:0/18:1(9Z)) + Water >2 PG(18:0/18:1(9Z)) + Phosphate
SMPDB Pathways:	phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/18:1(9Z)) PW001085
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 (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 splash10-05r0-4181702900-77795b2d9393345834cb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0ar0-7293603300-a87d0e9a2f44e72a6429 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a70-9055311000-999a567446019e711bc7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-01si-0190210400-76e275ef14cd3a01b5b5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-01si-5290200100-fb14b81b92a5a5f048c3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0059-9020100000-e13e4f6790f5550966ab View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-0000000900-1a681c2a3ed3bb343905 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-003r-0090310400-9b147c90eeab5c860848 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-003r-0190310400-8f6a1bac7e3458bae88d 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 89397 HMDB ID HMDB0010632 Pubchem Compound ID 52927224 Kegg ID Not Available ChemSpider ID 24768131 Wikipedia ID Not Available BioCyc ID Not Available

Enzymes