Human Metabolome Database Version 3.5

Showing metabocard for PGP(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (HMDB13574)

Record Information
Version 3.5
Creation Date 2010-05-13 10:10:20 -0600
Update Date 2013-02-08 17:30:36 -0700
Secondary Accession Numbers None
Metabolite Identification
Common Name PGP(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))
Description PGP(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is a phosphatidylglycerolphosphate or glycerophospholipid (PGP or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PGP(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one chain of g-linolenic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The g-linolenic acid moiety is derived from animal fats, while the docosapentaenoic acid moiety is derived from animal fats and brain. Phosphatidylglycerolphosphate is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of Phosphatidylglycerolphosphate increases during fetal development. Phosphatidylglycerolphosphate may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGPs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PGP also serves as a precursor for the synthesis of cardiolipin. PGP is synthesized from CDP-diacylglycerol and glycerol-3-phosphate.
Structure Thumb
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Display: 2D Structure | 3D Structure
  1. 1-g-Linolenoyl-2-osbondoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
  2. 1-gamma-Linolenoyl-2-osbondoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
  3. 3-Sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid
  4. PGP(18:3/22:5)
  5. PGP(18:3n6/22:5n6)
  6. PGP(18:3w6/22:5w6)
  7. PGP(40:8)
Chemical Formula C46H76O13P2
Average Molecular Weight 899.0354
Monoisotopic Molecular Weight 898.476115542
IUPAC Name [(2S)-3-({[(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name (2S)-3-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
CAS Registry Number Not Available
InChI Identifier InChI=1S/C46H76O13P2/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-46(49)59-44(42-58-61(53,54)57-40-43(47)39-56-60(50,51)52)41-55-45(48)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h11-14,17-19,21-23,26-29,32,34,43-44,47H,3-10,15-16,20,24-25,30-31,33,35-42H2,1-2H3,(H,53,54)(H2,50,51,52)/b13-11-,14-12-,19-17-,22-21-,23-18-,28-26-,29-27-,34-32-/t43-,44+/m0/s1
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Glycerophospholipids
Sub Class Glycerophosphoglycerophosphates
Other Descriptors
  • Aliphatic Acyclic Compounds
  • 1,2 Diacylglycerophosphoradylglycerol
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Dicarboxylic Acid Derivative
  • Fatty Acid Ester
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Secondary Alcohol
Direct Parent Phosphatidylglycerophosphates
Status Expected and Not Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 7.950E-04 g/L ALOGPS
LogP 7.41 ALOGPS
LogP 11.47 ChemAxon
LogS -6.05 ALOGPS
pKa (strongest acidic) 1.35 ChemAxon
pKa (strongest basic) -3.4 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 195.35 A2 ChemAxon
Rotatable Bond Count 42 ChemAxon
Refractivity 251.92 ChemAxon
Polarizability 98.06 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -3 ChemAxon
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location
  • All Tissues
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029574
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB13574 Link_out
Metagene Link HMDB13574 Link_out
METLIN ID Not Available
PubChem Compound 53481892 Link_out
PDB ID Not Available
ChEBI ID Not Available
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available