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Record Information
Version	2.0
Creation Date	2015-09-08 19:34:29 -0600
Update Date	2015-12-09 17:19:47 -0700
Secondary Accession Numbers	ECMDB24477
Identification
Name:	PGP(15:0cyclo/15:0cyclo)
Description	PGP(15:0cyclo/15:0cyclo) 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(15:0cyclo/15:0cyclo), in particular, consists of two cis-9,10-Methylenetetradecanoic acid chains at positions C-1 and C-2. 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:0xab1db018> Close
Synonyms:	Not Available
Chemical Formula:	C36H68O13P2
Weight:	Average: 770.875 Monoisotopic: 770.413516246
InChI Key:	YJXCEDKRKBCXCB-AZABDCPSSA-N
InChI:	InChI=1S/C36H68O13P2/c1-3-5-17-29-23-31(29)19-13-9-7-11-15-21-35(38)45-27-34(28-48-51(43,44)47-26-33(37)25-46-50(40,41)42)49-36(39)22-16-12-8-10-14-20-32-24-30(32)18-6-4-2/h29-34,37H,3-28H2,1-2H3,(H,43,44)(H2,40,41,42)/t29?,30?,31?,32?,33-,34-/m1/s1
CAS number:	Not Available
IUPAC Name:	[(2R)-3-({[(2R)-2,3-bis({[8-(2-butylcyclopropyl)octanoyl]oxy})propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name:	(2R)-3-{[(2R)-2,3-bis({[8-(2-butylcyclopropyl)octanoyl]oxy})propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
SMILES:	[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CCCCCCCC1CC1CCCC
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 Fatty acid ester Monoalkyl phosphate Dialkyl phosphate Dicarboxylic acid or derivatives Organic phosphoric acid derivative Phosphoric acid ester Alkyl phosphate Fatty acyl Secondary alcohol Carboxylic acid ester Carboxylic acid derivative Organooxygen compound Organic oxide Organic oxygen compound Alcohol Carbonyl group Hydrocarbon derivative Aliphatic homomonocyclic compound
Molecular Framework	Aliphatic homomonocyclic 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 0.0013 g/L ALOGPS logP 5.46 ALOGPS logP 8.37 ChemAxon logS -5.8 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 36 ChemAxon Refractivity 193.17 m³·mol⁻¹ ChemAxon Polarizability 86.02 ų ChemAxon Number of Rings 2 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(15:0cyclo/15:0cyclo) + Water >2 PG(15:0cyclo/15:0cyclo) + Phosphate
SMPDB Pathways:	phospholipid biosynthesis (CL(15:0cyclo/15:0cyclo/18:1(9Z)/16:0)) 1442599180 PW002016
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 splash10-0fl0-1370194700-c69788d1aec786a5ddad View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-001j-4690176500-655e7a7b44bbe227da85 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9681252200-e07d12ca6c904643a480 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00bi-4090030300-8934ed657b176013ee2b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9050000000-a6dea7e51e667c22bd3a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-033ffe55d77774c95540 View in MoNA MS Mass Spectrum (Electron Ionization) 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 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