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Record Information
Version	2.0
Creation Date	2015-09-08 19:34:46 -0600
Update Date	2015-12-09 17:20:03 -0700
Secondary Accession Numbers	ECMDB24483
Identification
Name:	PGP(16:0/12:0(3-OH))
Description	PGP(16:0/12:0(3-OH)) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(16:0/12:0(3-OH)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 3-hydroxydodecanoyl to the C-2 atom. In E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa680f8d0> Close
Synonyms:	Not Available
Chemical Formula:	C34H68O14P2
Weight:	Average: 762.852 Monoisotopic: 762.408430866
InChI Key:	DTDFJFRDLTUANE-YPHBKRNWSA-N
InChI:	InChI=1S/C34H68O14P2/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-33(37)44-28-32(29-47-50(42,43)46-27-31(36)26-45-49(39,40)41)48-34(38)25-30(35)23-21-19-17-10-8-6-4-2/h30-32,35-36H,3-29H2,1-2H3,(H,42,43)(H2,39,40,41)/t30?,31-,32-/m1/s1
CAS number:	Not Available
IUPAC Name:	[(2R)-3-({[(2R)-3-(hexadecanoyloxy)-2-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name:	(2R)-3-{[(2R)-3-(hexadecanoyloxy)-2-[(3-hydroxydodecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
SMILES:	[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CC(O)CCCCCCCCC
Chemical Taxonomy
Description	belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates 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	Glycerophosphoglycerophosphates
Direct Parent	Phosphatidylglycerophosphates
Alternative Parents	Glycerophosphates Monoalkyl phosphates Fatty acid esters Dialkyl phosphates Beta hydroxy acids and derivatives Dicarboxylic acids and derivatives Secondary alcohols Carboxylic acid esters Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Diacylglycerophosphoglycerophosphate Sn-glycerol-3-phosphate Beta-hydroxy acid Fatty acid ester Dialkyl phosphate Monoalkyl phosphate Dicarboxylic acid or derivatives Fatty acyl Alkyl phosphate Phosphoric acid ester Hydroxy acid Organic phosphoric acid derivative Carboxylic acid ester Secondary alcohol Carboxylic acid derivative Hydrocarbon derivative Organic oxide Alcohol Carbonyl group Organic oxygen compound Organooxygen compound Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.0042 g/L ALOGPS logP 4.77 ALOGPS logP 7.8 ChemAxon logS -5.3 ALOGPS pKa (Strongest Acidic) 1.35 ChemAxon pKa (Strongest Basic) -2.8 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 9 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 215.58 Ų ChemAxon Rotatable Bond Count 38 ChemAxon Refractivity 189.29 m³·mol⁻¹ ChemAxon Polarizability 85.56 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(16:0/12:0(3-OH)) + Water >2 PG(16:0/12:0(3-OH)) + Phosphate
SMPDB Pathways:	phospholipid biosynthesis (CL(16:0/12:0/12:0/12:0)) 2 PW001952
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_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0002-1860162900-1bc16b095586b1f602dc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0002-3960151300-29eda2040386c509c3ef View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0bta-8942133100-48cabeee9c1a0591001c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0bvs-3190030200-295c6a11dffb86dffc8b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9050000000-c21a12179b3cc0027c6d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9010000000-315c664fb98dd57f1f8e 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:	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

Enzymes