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Record Information
Version	2.0
Creation Date	2015-09-08 17:49:34 -0600
Update Date	2015-12-09 12:07:30 -0700
Secondary Accession Numbers	ECMDB24132
Identification
Name:	PG(16:0/18:1(9Z))
Description	PG(16:0/18:1(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(16:0/18:1(9Z)), in particular, consists of one hexadecanoyl 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:0xaa70aa6c> Close
Synonyms:	Value Source 1-Oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-sn-glycerol) ChEBI 18:1/16:0 PG ChEBI 2-Hexadecanoyl-1-[(9Z)-octadec-9-enoyl]-sn-glycero-3-phospho-(1'-sn-glycerol) ChEBI C18:1/16:0 PG ChEBI GPG(18:1/16:0) ChEBI GPG(18:1OMEGA9/16:0) ChEBI GPG(34:1) ChEBI PG(18:1/16:0) ChEBI PG(18:1OMEGA9/16:0) ChEBI PG(34:1) ChEBI Phosphatidylglycerol(18:1/16:0) ChEBI Phosphatidylglycerol(18:1omega9/16:0) ChEBI Phosphatidylglycerol(34:1) ChEBI 1-(9Z-Octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phospho-(1'-glycerol) HMDB 1-Oleoyl-2-palmitoyl-sn-glycero-3-phosphoglycerol HMDB GPG(18:1N9/16:0) HMDB GPG(18:1W9/16:0) HMDB PG(18:1N9/16:0) HMDB PG(18:1W9/16:0) HMDB Phosphatidylglycerol(18:1n9/16:0) HMDB Phosphatidylglycerol(18:1W9/16:0) HMDB 1-(9Z-Octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphoglycerol HMDB 1-Oleoyl-2-palmitoyl-GPG HMDB 1-Oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-glycerol) HMDB 1-Oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1’-glycerol) HMDB GPG(18:1(9Z)/16:0) HMDB Phosphatidylglycerol(18:1(9Z)/16:0) HMDB PG(18:1(9Z)/16:0) Lipid Annotator
Chemical Formula:	C40H77O10P
Weight:	Average: 749.0071 Monoisotopic: 748.525435196
InChI Key:	GTCKEWVHTGGUSN-HGWHEPCSSA-N
InChI:	InChI=1S/C40H77O10P/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/h17-18,37-38,41-42H,3-16,19-36H2,1-2H3,(H,45,46)/b18-17-/t37-,38+/m0/s1
CAS number:	Not Available
IUPAC Name:	[(2S)-2,3-dihydroxypropoxy][(2R)-2-(hexadecanoyloxy)-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name:	(2S)-2,3-dihydroxypropoxy((2R)-2-(hexadecanoyloxy)-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)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. 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	1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) (CHEBI:73206 ) Diacylglycerophosphoglycerols (LMGP04010962 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.0001 g/L ALOGPS logP 8.17 ALOGPS logP 11.46 ChemAxon logS -6.9 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 205.63 m³·mol⁻¹ ChemAxon Polarizability 91.38 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(16:0/18:1(9Z)) + Water > PG(16:0/18:1(9Z)) + Phosphate PE(17:0cycw7c/17:0cycw7c) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(16:0/17:0cycw7c/17:0cycw7c/18:1(9Z)) PE(17:0cycw7c/17:0cycw7c) + PG(16:0/18:1(9Z)) > CL(16:0/17:0cycw7c/18:1(9Z)/17:0cycw7c) + Ethanolamine PE(17:0cycw7c/17:0cycw7c) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(16:0/18:1(9Z)/17:0cycw7c/17:0cycw7c) PE(19:iso/19:0cycv8c) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(16:0/18:1(9Z)/19:0cycv8c/19:0cycv8c) PG(16:0/18:1(9Z)) + PE(19:iso/19:iso) > Ethanolamine + CL(16:0/19:0cycv8c/18:1(9Z)/19:0cycv8c) PE(19:iso/19:iso) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(16:0/19:0cycv8c/19:0cycv8c/18:1(9Z)) PE(17:0cycw7c/17:0cycw7c) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(17:0cycw7c/16:0/17:0cycw7c/18:1(9Z)) PE(17:0cycw7c/17:0cycw7c) + PG(16:0/18:1(9Z)) > CL(17:0cycw7c/16:0/18:1(9Z)/17:0cycw7c) + Ethanolamine PE(15:0/18:1(9Z)) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/16:0/18:1(9Z)) PE(19:0cycv8c/19:iso) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(19:0cycv8c/16:0/18:1(9Z)/19:0cycv8c)
SMPDB Pathways:	phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/16:0/18:1(9Z))) PW001518 phospholipid biosynthesis (CL(19:0cycv8c/16:0/18:1(9Z)/19:0cycv8c)) PW001334 phospholipid biosynthesis CL(16:0/17:0cycw7c/17:0cycw7c/18:1(9Z)) PW001348 phospholipid biosynthesis CL(16:0/17:0cycw7c/18:1(9Z)/17:0cycw7c) PW001350 phospholipid biosynthesis CL(16:0/18:1(9Z)/17:0cycw7c/17:0cycw7c) PW001365 phospholipid biosynthesis CL(16:0/18:1(9Z)/19:0cycv8c/19:0cycv8c) PW001381 phospholipid biosynthesis CL(16:0/19:0cycv8c/18:1(9Z)/19:0cycv8c) PW001409 phospholipid biosynthesis CL(16:0/19:0cycv8c/19:0cycv8c/18:1(9Z)) PW001413 phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/17:0cycw7c/18:1(9Z)) PW001565 phospholipid biosynthesis CL(17:0cycw7c/16:0/17:0cycw7c/18:1(9Z)) PW001684 phospholipid biosynthesis CL(17:0cycw7c/16:0/18:1(9Z)/17:0cycw7c) PW001690
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 splash10-017v-3190520500-9e49914c88c80e67b390 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00p0-4291311100-32f3d951cc40e9104fc2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-05br-9083221000-0f34b30ee5894adf3ac9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-06sj-0190200200-42a24e8e202dfd4937f4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-01si-4290100000-7d8c4a95374ecdeff64a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9030000000-fa08da539f300400a5ca View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0002-0000000900-2b6e33dc3e3568f4d2fd View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0a61-0090300400-f3f2ad392aa2f94f83cd View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-053s-0190300400-41a2c1de2632833af2ef 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 73206 HMDB ID HMDB0010630 Pubchem Compound ID 52927225 Kegg ID Not Available ChemSpider ID 24768129 Wikipedia ID Not Available BioCyc ID Not Available

Enzymes