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Record Information
Version	2.0
Creation Date	2012-08-15 08:51:33 -0600
Update Date	2015-06-03 17:22:01 -0600
Secondary Accession Numbers	ECMDB21656
Identification
Name:	Phosphatidylglycerophosphate
Description	Phosphatidylglycerophosphate belongs to the class of Phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x89b14250> Close
Synonyms:	1,2-Diacyl-sn-glycero-3-phospho-sn-glycerol 3'-phosphate 1,2-Diacyl-sn-glycero-3-phospho-sn-glycerol 3'-phosphoric acid 3(3-Phosphatidyl-)L-glycerol 1-phosphate 3(3-Phosphatidyl-)L-glycerol 1-phosphoric acid 3(3-Sn-Phosphatidyl)-sn-glycerol 1-phosphate 3(3-sn-Phosphatidyl)-sn-glycerol 1-phosphoric acid Phosphatidylglycerol phosphates Phosphatidylglycerophosphate Phosphatidylglycerophosphoric acid
Chemical Formula:	C8H16O13P2
Weight:	Average: 382.1524 Monoisotopic: 382.006613622
InChI Key:	ZSPJCYNIVYENCI-JGVFFNPUSA-N
InChI:	InChI=1S/C8H16O13P2/c9-5-17-3-8(18-6-10)4-21-23(15,16)20-2-7(11)1-19-22(12,13)14/h5-8,11H,1-4H2,(H,15,16)(H2,12,13,14)/t7-,8+/m0/s1
CAS number:	Not Available
IUPAC Name:	[(2S)-3-({[(2R)-2,3-bis(formyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name:	(2S)-3-{[(2R)-2,3-bis(formyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
SMILES:	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC=O)OC=O
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 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 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 7.66 g/L ALOGPS logP -1.1 ALOGPS logP -2.2 ChemAxon logS -1.7 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 14 ChemAxon Refractivity 68.32 m³·mol⁻¹ ChemAxon Polarizability 29.35 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	CDP-diacylglycerol + Glycerol 3-phosphate <> Cytidine monophosphate + Phosphatidylglycerophosphate Phosphatidylglycerophosphate + Water <> Phosphatidylglycerol + Phosphate + PG(16:0/16:0) Phosphatidylglycerophosphate + Water > phosphatidylglycerol + Inorganic phosphate CDP-diacylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Phosphatidylglycerophosphate CDP-diacylglycerol + Glycerol 3-phosphate <> Cytidine monophosphate + Phosphatidylglycerophosphate Phosphatidylglycerophosphate + Water <> PG(16:0/16:0) + Phosphate CDP-diacylglycerol + Glycerol 3-phosphate <> Cytidine monophosphate + Phosphatidylglycerophosphate Phosphatidylglycerophosphate + Water <> PG(16:0/16:0) + Phosphate
SMPDB Pathways:	Not Available
KEGG Pathways:	Glycerophospholipid metabolism ec00564 Metabolic pathways eco01100
EcoCyc Pathways:	phospholipid biosynthesis I PHOSLIPSYN-PWY
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 splash10-0019-2449000000-4432684415598adfd898 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-053j-6962000000-9a805aadc83776f292db View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-052r-9710000000-d71253aac77bc3c982af View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-003r-9148000000-e1b34167e5f0ead87ade View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9010000000-9d16e501b9bf5a96a54f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-f6224db456271dac0375 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 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 17264 HMDB ID Not Available Pubchem Compound ID 46873832 Kegg ID C03892 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

Enzymes