Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information
Version	2.0
Creation Date	2015-09-08 19:00:37 -0600
Update Date	2015-09-16 17:34:58 -0600
Secondary Accession Numbers	ECMDB24296
Identification
Name:	PGP(16:1(9Z)/18:3(9Z,12Z,15Z))
Description	PGP(16:1(9Z)/18:3(9Z,12Z,15Z)) 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(16:1(9Z)/18:3(9Z,12Z,15Z)), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one 9Z,12Z,15Z-octadecatrienoyl 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:0xa8277010> Close
Synonyms:	Not Available
Chemical Formula:	C40H72O13P2
Weight:	Average: 822.951 Monoisotopic: 822.444816374
InChI Key:	BWXRBYQNARBPBA-NJXCWUJZSA-N
InChI:	InChI=1S/C40H72O13P2/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(43)53-38(36-52-55(47,48)51-34-37(41)33-50-54(44,45)46)35-49-39(42)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h5,7,11,13-14,16-18,37-38,41H,3-4,6,8-10,12,15,19-36H2,1-2H3,(H,47,48)(H2,44,45,46)/b7-5-,13-11-,16-14-,18-17-/t37-,38+/m0/s1
CAS number:	Not Available
IUPAC Name:	[(2S)-3-({[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name:	(2S)-3-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
SMILES:	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
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 6.77 ALOGPS logP 10.25 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 219.85 m³·mol⁻¹ ChemAxon Polarizability 91.82 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:
SMPDB Pathways:	Not Available
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 splash10-0ab9-0290050150-cd464c8214ba65946eff View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0bti-1491021010-6f98f25d1ed6d8121f40 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0btj-3692120100-85638b27893a3c1d1d03 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0fbi-2090020020-3717a4b046af4257f4f8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0fb9-9060000000-88e51944ef41b1748d23 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9010000000-0fab719f3ac37d0d4a21 View in MoNA
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