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Record Information
Version	2.0
Creation Date	2015-09-08 19:32:58 -0600
Update Date	2016-09-13 16:36:03 -0600
Secondary Accession Numbers	ECMDB24446
Identification
Name:	PGP(12:0/19:iso)
Description	PGP(12:0/19:iso) 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(12:0/19:iso), in particular, consists of one dodecanoyl chain to the C-1 atom, and one 17-methylocatdecanoyl 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:0xa2d21c00> Close
Synonyms:	Not Available
Chemical Formula:	C37H74O13P2
Weight:	Average: 788.934 Monoisotopic: 788.460466439
InChI Key:	HXMDQPQFHAPSFV-OIDHKYIRSA-N
InChI:	InChI=1S/C37H74O13P2/c1-4-5-6-7-8-14-18-21-24-27-36(39)46-31-35(32-49-52(44,45)48-30-34(38)29-47-51(41,42)43)50-37(40)28-25-22-19-16-13-11-9-10-12-15-17-20-23-26-33(2)3/h33-35,38H,4-32H2,1-3H3,(H,44,45)(H2,41,42,43)/t34-,35+/m0/s1
CAS number:	Not Available
IUPAC Name:	[(2S)-3-({[(2R)-3-(dodecanoyloxy)-2-[(17-methyloctadecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name:	(2S)-3-{[(2R)-3-(dodecanoyloxy)-2-[(17-methyloctadecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
SMILES:	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCC(C)C
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 Dicarboxylic acids and derivatives Secondary alcohols Carboxylic acid esters Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Diacylglycerophosphoglycerophosphate Sn-glycerol-3-phosphate Dialkyl phosphate Monoalkyl phosphate Fatty acid ester Fatty acyl Alkyl phosphate Phosphoric acid ester Organic phosphoric acid derivative Dicarboxylic acid or derivatives Secondary alcohol Carboxylic acid ester Carboxylic acid derivative Organic oxygen compound Organic oxide Hydrocarbon derivative Organooxygen compound Carbonyl group Alcohol 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 0.0011 g/L ALOGPS logP 6.04 ALOGPS logP 10.21 ChemAxon logS -5.9 ALOGPS pKa (Strongest Acidic) 1.35 ChemAxon pKa (Strongest Basic) -3.4 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 195.35 Ų ChemAxon Rotatable Bond Count 40 ChemAxon Refractivity 201.53 m³·mol⁻¹ ChemAxon Polarizability 90.74 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 CDP-DG(12:0/19:iso) + Glycerol 3-phosphate >2 PGP(12:0/19:iso) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate 2 PGP(12:0/19:iso) + Water >2 PG(12:0/19:iso) + Phosphate
SMPDB Pathways:	phospholipid biosynthesis (CL(12:0/19:iso/12:0/19:iso)) PW001933
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 splash10-008l-0790342700-0d09aea801344d598eef View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-053r-2971122200-2bd1f96985b1da271c37 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4r-4961010000-a728e8fa3a3460dc95ee View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-003b-4950111300-209ab970fe71f37280c6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004j-9410000000-bbeda56658be25ebac55 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-ceb164a7db9a403da124 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